DE4424712A1 - Use of benzaldehydes to mark hydrocarbons - Google Patents
Use of benzaldehydes to mark hydrocarbonsInfo
- Publication number
- DE4424712A1 DE4424712A1 DE4424712A DE4424712A DE4424712A1 DE 4424712 A1 DE4424712 A1 DE 4424712A1 DE 4424712 A DE4424712 A DE 4424712A DE 4424712 A DE4424712 A DE 4424712A DE 4424712 A1 DE4424712 A1 DE 4424712A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- alkyl
- benzaldehydes
- radical
- hydrocarbons
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000003935 benzaldehydes Chemical class 0.000 title claims abstract description 27
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 25
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 25
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 239000003550 marker Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- -1 1,4-butylene Chemical group 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 7
- 125000001033 ether group Chemical group 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- UNQLRWBLUDHEDR-UHFFFAOYSA-N morpholin-4-yl-piperidin-1-yl-pyrrolidin-1-yl-lambda3-chlorane Chemical compound N1(CCCC1)Cl(N1CCOCC1)N1CCCCC1 UNQLRWBLUDHEDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002283 diesel fuel Substances 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 229960004756 ethanol Drugs 0.000 description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229960005335 propanol Drugs 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- SUSCOLVXUKHTET-UHFFFAOYSA-N 2,3-dimethylchromenylium Chemical compound C1=CC=C2[O+]=C(C)C(C)=CC2=C1 SUSCOLVXUKHTET-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- PWGVOCGNHYMDLS-UHFFFAOYSA-N 3-(2-methoxyethoxy)propan-1-amine Chemical compound COCCOCCCN PWGVOCGNHYMDLS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- FNJSWIPFHMKRAT-UHFFFAOYSA-N Monomethyl phthalate Chemical class COC(=O)C1=CC=CC=C1C(O)=O FNJSWIPFHMKRAT-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 235000005505 Ziziphus oenoplia Nutrition 0.000 description 1
- 244000104547 Ziziphus oenoplia Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- DJDSLBVSSOQSLW-UHFFFAOYSA-N mono(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O DJDSLBVSSOQSLW-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
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- C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
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- C10L1/2286—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen triple bonds, e.g. nitriles
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- C10M171/007—Coloured or dyes-containing lubricant compositions
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- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/26—Oils; Viscous liquids; Paints; Inks
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Abstract
Description
Die vorliegende Erfindung betrifft die Verwendung von Benz aldehyden der Formel IThe present invention relates to the use of benz aldehydes of the formula I.
in der
der Ring A benzoanelliert sein kann,
R¹, R² und R³ unabhängig voneinander jeweils Wasserstoff, Hydroxy,
C₁-C₁₅-Alkyl, C₁-C₁₅-Alkoxy, Cyano, Nitro oder einen Rest der
Formel NR⁴R⁵ oder COOR⁶ bedeuten, worin
R⁴ für Wasserstoff oder C₁-C₁₅-Alkyl, das durch 1 bis
4 Sauerstoffatome in Etherfunktion unterbrochen sein kann
und gegebenenfalls durch Phenyl substituiert ist,
R⁵ für C₁-C₁₅-Alkyl, das durch 1 bis 4 Sauerstoffatome in
Etherfunktion unterbrochen sein kann und gegebenenfalls
durch Phenyl substituiert ist, oder einen Rest der Formel
L-NX¹X², worin L die Bedeutung von C₂-C₈-Alkylen und X¹
und X² unabhängig voneinander jeweils die Bedeutung von
C₁-C₆-Alkyl oder zusammen mit dem sie verbindenden Stick
stoffatom die Bedeutung eines 5- oder 6-gliedrigen ge
sättigten heterocyclischen Rests, der noch ein Sauer
stoffatom im Ring enthalten kann, besitzen, und
R⁶ für Wasserstoff, C₁-C₁₅-Alkyl, das durch 1 bis 4 Sauer
stoffatome in Etherfunktion unterbrochen sein kann, oder
für einen Rest der Formel L-NX¹X², worin L, X¹ und X² je
weils die obengenannte Bedeutung besitzen, stehen,
als Markierungsmittel für Kohlenwasserstoffe, ein Verfahren zum
Nachweis dieser Benzaldehyde in Kohlenwasserstoffen sowie Kohlen
wasserstoffe, enthaltend die obengenannten Benzaldehyde.in the
ring A can be fused to benzo
R¹, R² and R³ each independently represent hydrogen, hydroxy, C₁-C₁₅ alkyl, C₁-C₁₅ alkoxy, cyano, nitro or a radical of the formula NR⁴R⁵ or COOR⁶, in which
R⁴ represents hydrogen or C₁-C₁₅ alkyl, which can be interrupted by 1 to 4 oxygen atoms in ether function and is optionally substituted by phenyl,
R⁵ for C₁-C₁₅-alkyl, which can be interrupted by 1 to 4 oxygen atoms in ether function and optionally substituted by phenyl, or a radical of the formula L-NX¹X², where L is independently the meaning of C₂-C₈-alkylene and X¹ and X² each have the meaning of C₁-C₆-alkyl or together with the nitrogen atom connecting them the meaning of a 5- or 6-membered ge saturated heterocyclic radical, which may still contain an oxygen atom in the ring, and
R⁶ represents hydrogen, C₁-C₁₅ alkyl, which can be interrupted by 1 to 4 oxygen atoms in ether function, or a radical of the formula L-NX¹X², in which L, X¹ and X² each have the abovementioned meaning,
as a marking agent for hydrocarbons, a method for the detection of these benzaldehydes in hydrocarbons and hydrocarbons, containing the above-mentioned benzaldehydes.
Aus der US-A-5 145 573, US-A-5 182 372 sowie der EP-A-499 845 sind bereits Azofarbstoffe bekannt, die als Markierungsmittel für Mineralöle dienen. In der US-A-4 009 008 wird weiterhin ein Ver fahren zum Markieren von Mineralölen mittels Disazofarbstoffen beschrieben, bei dem man den dem Mineralöl zugesetzten Farbstoff sichtbar macht, indem man ein Adsorptionsmittel dem markierten Mineralöl zusetzt, das andere farbige Bestandteile des Mineralöls bindet.From US-A-5 145 573, US-A-5 182 372 and EP-A-499 845 Azo dyes are already known as markers for Mineral oils. In US-A-4 009 008 a Ver drive to mark mineral oils using disazo dyes described in which one added the dye to the mineral oil visualized by placing an adsorbent on the marked Mineral oil adds, the other colored components of the mineral oil binds.
In der DE-A-36 08 215 und der DE-A-37 24 757 sind Benzopyranderi vate sowie deren Verwendung in Aufzeichnungssystemen beschrieben.In DE-A-36 08 215 and DE-A-37 24 757 are Benzopyranderi vate and their use in recording systems.
Im Beispiel 1 der DE-A-36 08 215 ist die Umsetzung von 2,3-Di methylbenzopyrylium-trichlorozinkat mit 4-Dimethylaminobenzal dehyd in Methanol unter Bildung des Farbsalzes der FormelIn example 1 of DE-A-36 08 215 is the implementation of 2,3-di methylbenzopyrylium trichlorozincate with 4-dimethylaminobenzal dehyd in methanol to form the color salt of the formula
beschrieben.described.
In der WO-A-11 466/1994 ist die Verwendung von substituierten Anilinen zum Markieren von Mineralölen beschrieben.WO-A-11 466/1994 describes the use of substituted Anilines described for marking mineral oils.
Aufgabe der vorliegenden Erfindung war es, neue Mittel zum Mar kieren von Kohlenwasserstoffen bereitzustellen. Die neuen Mittel sollten leicht zugänglich und gut in Kohlenwasserstoffen löslich sein. Außerdem sollten sie in einfacher Weise nachgewiesen werden können. Dabei sollten selbst noch sehr kleine Mengen an Markier stoff durch eine starke Farbreaktion sichtbar gemacht werden können.The object of the present invention was to develop new means of mar to provide hydrocarbons. The new means should be easily accessible and readily soluble in hydrocarbons his. They should also be demonstrated in a simple manner can. Even very small amounts of marking should be used be made visible through a strong color reaction can.
Demgemäß wurde gefunden, daß sich die eingangs näher bezeichneten Benzaldehyde der Formel I vorteilhaft als Markierungsmittel für Kohlenwasserstoffe eignen.Accordingly, it was found that the above described themselves Benzaldehydes of formula I advantageous as a marker for Hydrocarbons are suitable.
Alle in der obengenannten Formel I auftretenden Alkyl- und Alkylenreste können sowohl geradkettig als auch verzweigt sein. All alkyl and in the formula I mentioned above Alkylene radicals can be both straight-chain and branched.
Wenn X¹ und X² zusammen mit dem sie verbindenden Stickstoffatom einen 5- oder 6-gliedrigen gesättigten heterocyclischen Rest, der noch ein Sauerstoffatom im Ring enthalten kann, bedeuten, so kön nen dafür z. B. Pyrrolidinyl, Piperidinyl oder Morpholinyl in Be tracht kommen.When X¹ and X² together with the nitrogen atom connecting them a 5- or 6-membered saturated heterocyclic radical which can still contain an oxygen atom in the ring, so can NEN z. B. pyrrolidinyl, piperidinyl or morpholinyl in Be come.
Reste R¹, R², R³, R⁴, R⁵, R⁶, X¹ und X² sind z. B. Methyl, Ethyl, Propyl, Isopropyl, Butyl, Isobutyl, sec-Butyl, Pentyl, Isopen tyl, Neopentyl, tert-Pentyl, Hexyl oder 2-Methylpentyl.R¹, R², R³, R⁴, R⁵, R⁶, X¹ and X² are z. B. methyl, ethyl, Propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopen tyl, neopentyl, tert-pentyl, hexyl or 2-methylpentyl.
Reste R¹, R², R³, R⁴, R⁵ und R⁶ sind weiterhin z. B. Heptyl, Octyl, 2-Ethylhexyl, Isooctyl, Nonyl, Isononyl, Decyl, Isodecyl, Undecyl, Dodecyl, Tridecyl, 3,5,5,7-Tetramethylnonyl, Isotride cyl, Tetradecyl oder Pentadecyl (die obigen Bezeichnungen Iso octyl, Isononyl, Isodecyl und Isotridecyl sind Trivialbezeichnun gen und stammen von den nach der Oxosynthese erhaltenen Alkoholen - vgl. dazu Ullmann′s Encyclopedia of Industrial Chemistry, 5th Edition, Vol. Al, Seiten 290 bis 293, sowie Vol. A 10, Seiten 284 und 285).R¹, R², R³, R⁴, R⁵ and R⁶ are still z. B. heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, Undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotrides cyl, tetradecyl or pentadecyl (the above designations Iso octyl, isononyl, isodecyl and isotridecyl are trivial names genes and come from the alcohols obtained after oxosynthesis - see. also Ullmann’s Encyclopedia of Industrial Chemistry, 5th Edition, Vol. Al, pages 290 to 293, and Vol. A 10, pages 284 and 285).
Reste R¹, R² und R³ sind weiterhin z. B. Methoxy, Ethoxy, Propoxy, Isopropoxy, Butoxy, Isobutoxy, sec-Butoxy, Pentyloxy, Isopentyl oxy, Neopentyloxy, tert-Pentyloxy, Hexyloxy, 2-Methylpentyloxy, Heptyloxy, Octyloxy, 2-Ethylhexyloxy, Isooctyloxy, Nonyloxy, Iso nonyloxy, Decyloxy, Isodecyloxy, Undecyloxy, Dodecyloxy, Tride cyloxy, 3,5,5,7-Tetramethylnonyloxy, Isotridecyloxy, Tetradecyl oxy oder Pentadecyloxy.Residues R¹, R² and R³ are still z. B. methoxy, ethoxy, propoxy, Isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyl oxy, neopentyloxy, tert-pentyloxy, hexyloxy, 2-methylpentyloxy, Heptyloxy, octyloxy, 2-ethylhexyloxy, isooctyloxy, nonyloxy, iso nonyloxy, decyloxy, isodecyloxy, undecyloxy, dodecyloxy, tride cyloxy, 3,5,5,7-tetramethylnonyloxy, isotridecyloxy, tetradecyl oxy or pentadecyloxy.
Reste R⁴ und R⁵ sind weiterhin z. B. 2-Methoxyethyl, 2-Ethoxyethyl, 2-Propoxyethyl, 2-Isopropoxyethyl, 2-Butoxyethyl, 2- oder 3-Meth oxypropyl, 2- oder 3-Ethoxypropyl, 2- oder 3-Propoxypropyl, 2- oder 3-Butoxypropyl, 2- oder 4-Methoxybutyl, 2- oder 4-Ethoxy butyl, 2- oder 4-Propoxybutyl, 2- oder 4-Butoxybutyl, 3,6-Dioxa heptyl, 3,6-Dioxaoctyl, 4,8-Dioxanonyl, 3,7-Dioxaoctyl, 3,7-Dioxanonyl, 4,7-Dioxaoctyl, 4,7-Dioxanonyl, 4,8-Dioxadecyl, 3,6,8-Trioxadecyl, 3,6,9-Trioxaundecyl, 3,6,9,12-Tetraoxatri decyl, Benzyl oder 1- oder 2-Phenylethyl.R⁴ and R⁵ are still z. B. 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-meth oxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxy butyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxa heptyl, 3,6-dioxaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3,6,8-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatri decyl, benzyl or 1- or 2-phenylethyl.
Reste L sind z. B. (CH₂)₂, (CH₂)₃, (CH₂)₄, (CH₂)₅, (CH₂)₆, (CH₂)₇, (CH₂)₈, CH(CH₃)CH₂ oder CH(CH₃)CH(CH₃).L are z. B. (CH₂) ₂, (CH₂) ₃, (CH₂) ₄, (CH₂) ₅, (CH₂) ₆, (CH₂) ₇, (CH₂) ₈, CH (CH₃) CH₂ or CH (CH₃) CH (CH₃).
Erfindungsgemäß bevorzugt werden Benzaldehyde der Formel I verwendet, bei denen mindestens einer der Reste R¹ bis R³ einen Rest der Formel NR⁴R⁵ bedeutet, worin R⁴ und R⁵ jeweils die oben genannte Bedeutung besitzen. Benzaldehydes of the formula I are preferred according to the invention used, in which at least one of the radicals R¹ to R³ one The remainder of the formula NR⁴R⁵ means, wherein R⁴ and R⁵ each have the above have the meaning given.
Besonders bevorzugt werden Benzaldehyde der Formel IaBenzaldehydes of the formula Ia are particularly preferred
in der R¹, R², R⁴ und R⁵ jeweils die obengenannte Bedeutung besit zen, zum Markieren von Kohlenwasserstoffen verwendet.in which R¹, R², R⁴ and R⁵ each have the abovementioned meaning zen, used for marking hydrocarbons.
Besonders geeignet sind Benzaldehyde der Formel Ia, in der R¹ und R² unabhängig voneinander jeweils Wasserstoff, Hydroxy, C₁-C₁₅-Alkyl, C₁-C₁₅-Alkoxy oder einen Rest der Formel COOR⁶, worin R⁶ die obengenannte Bedeutung besitzt, R⁴ Wasserstoff oder C₁-C₁₅-Alkyl und R⁵ C₁-C₁₅-Alkyl bedeuten.Benzaldehydes of the formula Ia in which R 1 and R² independently of one another are each hydrogen, hydroxy, C₁-C₁₅ alkyl, C₁-C₁₅ alkoxy or a radical of the formula COOR⁶, wherein R⁶ has the meaning given above, R⁴ is hydrogen or C₁-C₁₅ alkyl and R⁵ are C₁-C₁₅ alkyl.
Besonders bevorzugt werden Benzaldehyde der Formel Ia, in der R⁴ und R⁵ unabhängig voneinander jeweils C₁-C₁₃-Alkyl, sowie R¹ und R² jeweils Wasserstoff bedeuten, zum Markieren von Kohlenwasserstof fen verwendet.Benzaldehydes of the formula Ia in which R in are particularly preferred and R⁵ are each independently C₁-C₁₃ alkyl, and R¹ and R² each represent hydrogen, for marking hydrocarbons fen used.
Gegenstand der Erfindung ist außerdem ein Verfahren zum Nachweis der Anwesenheit von Benzaldehyden der Formel I in Kohlenwasser stoffen, wobei man den Kohlenwasserstoff mit einem wäßrig-alkoho lischen oder alkoholischen Medium behandelt, das eine Proton säure, mindestens eine Verbindung aus der Gruppe der Verbindun gen, bestehend aus substituierten Benzopyryliumsalzen der For mel IIThe invention also relates to a method for detection the presence of benzaldehydes of formula I in hydrocarbon substances, the hydrocarbon with an aqueous alcohol tical or alcoholic medium that contains a proton acid, at least one compound from the group of compounds gene consisting of substituted benzopyrylium salts of For mel II
in der R⁷ für C₁-C₈-Alkyl, Phenyl, C₁-C₅-Alkoxy oder Halogen und R⁸ für Methyl oder R⁷ und R⁸ zusammen für 1,4-Butylen stehen und der Ring B durch einen Benzolring anelliert sein kann und gegebenen falls durch C₁-C₄-Alkyl, Pyrrolidino, Piperidino, Morpholino, Chlor oder Brom oder in Ringposition 7 gegebenenfalls auch durch Hydroxy, C₁-C₄-Alkoxy, C₁-C₅-Mono- oder Dialkylamino, das jeweils wiederum durch Chlor oder Phenyl substituiert sein kann, substi tuiert ist und X⊖ ein beliebiges Anion bedeutet, und Indolen der Formel III in the R⁷ for C₁-C₈ alkyl, phenyl, C₁-C₅ alkoxy or halogen and R und represent methyl or R⁷ and R⁸ together for 1,4-butylene and the Ring B can be fused by a benzene ring and given if by C₁-C₄-alkyl, pyrrolidino, piperidino, morpholino, Chlorine or bromine or in ring position 7 if necessary also Hydroxy, C₁-C₄ alkoxy, C₁-C₅ mono- or dialkylamino, each can in turn be substituted by chlorine or phenyl, substi is tuiert and X⊖ means any anion, and indoles the Formula III
in der R⁹ und R¹⁰ unabhängig voneinander jeweils für Wasserstoff,
Hydroxy, einen Rest der Formel NR⁴R⁵, worin R⁴ und R⁵ jeweils die
obengenannte Bedeutung besitzen, C₁-C₈-Alkyl, Phenyl, C₁-C₅-Alkoxy
oder Halogen stehen,
und gegebenenfalls ein Halogenid der Metalle Zink, Aluminium oder
Zinn enthält.in which R⁹ and R¹⁰ each independently represent hydrogen, hydroxy, a radical of the formula NR⁴R⁵, in which R⁴ and R⁵ each have the abovementioned meaning, are C₁-C--alkyl, phenyl, C₁-C₅-alkoxy or halogen,
and optionally containing a halide of the metals zinc, aluminum or tin.
Bevorzugt werden erfindungsgemäß Indole der Formel III, ins besondere 2-Phenylindol, verwendet.According to the invention, preference is given to indoles of the formula III, ins special 2-phenylindole used.
Beispiele für geeignete Anionen X⊖ sind Tetrachlorozinkat, Halo genid, Sulfat, Tetrafluoroborat oder Phosphat.Examples of suitable anions X⊖ are tetrachlorozincate, halo genide, sulfate, tetrafluoroborate or phosphate.
Die Benzaldehyde I, die Benzopyryliumsalze II sowie die In dole III sind in der Regel an sich bekannt.The Benzaldehyde I, the Benzopyryliumsalze II and the In dole III are usually known per se.
Unter Markierung im erfindungsgemäßen Sinn ist ein Zusatz der Benzaldehyde der Formel I in solcher Konzentration zu Kohlenwas serstoffen zu verstehen, daß die Kohlenwasserstoffe dadurch für das menschliche Auge entweder überhaupt nicht oder nur wenig sichtbar angefärbt sind, wobei jedoch die Benzaldehyde der For mel I durch die hier näher beschriebenen Nachweismethoden leicht und deutlich sichtbar detektierbar sind.Under marking in the sense of the invention is an addition of Benzaldehydes of formula I in such a concentration to coal water to understand that the hydrocarbons thereby for the human eye either not at all or only a little are visibly stained, but the benzaldehydes of For mel I easily by the detection methods described here and are clearly visible.
Ein weiterer Gegenstand der vorliegenden Erfindung sind Kohlen wasserstoffe, enthaltend einen oder mehrere der Benzaldehyde der Formel I.Another object of the present invention are coals Hydrogen containing one or more of the benzaldehydes Formula I.
Unter Kohlenwasserstoffen im erfindungsgemäßen Sinn sind alipha tische oder aromatische Kohlenwasserstoffe zu verstehen, die unter Normalbedingungen in flüssigem Aggregatzustand vorliegen.Among hydrocarbons in the sense of the invention are alipha to understand table or aromatic hydrocarbons that be in a liquid state under normal conditions.
Dies sind insbesondere Mineralöle, beispielsweise Treibstoffe, wie Benzin, Kerosin oder Dieselöl, oder Öle, wie Heizöl oder Mo torenöl.These are in particular mineral oils, for example fuels, such as gasoline, kerosene or diesel oil, or oils such as heating oil or Mo. gate oil.
Die Benzaldehyde der Formel I eignen sich insbesondere zum Mar kieren von Mineralölen, bei denen eine Kennzeichnung gefordert wird, z. B. aus steuerlichen Gründen. Um die Kosten der Kennzeich nung gering zu halten, strebt man dabei an, für die Markierung möglichst geringe Mengen an Markierungsmittel anzuwenden.The benzaldehydes of formula I are particularly suitable for mar mineral oils for which labeling is required will, e.g. B. for tax reasons. To the cost of the label The aim is to keep the voltage low, for the marking use the smallest possible amount of marker.
Zum Markieren von Kohlenwasserstoffen werden die Benzaldehyde der Formel I entweder in Substanz oder in Form von Lösungen ange wandt. Als Lösungsmittel eignen sich organische Lösungsmittel. Vorzugsweise kommen aromatische Kohlenwasserstoffe, wie Toluol, Xylol, Dodecylbenzol, Diisopropylnaphthalin oder ein Gemisch hö herer Aromaten, das unter dem Namen Shellsol® AB (Fa. Shell) han delsüblich ist, zur Anwendung. Um eine hohe Viskosität der resul tierenden Lösungen zu vermeiden, wählt man im allgemeinen eine Konzentration an Benzaldehyden I von 5 bis 80 Gew.-%, bezogen auf die Lösung.To mark hydrocarbons, the benzaldehydes Formula I either in substance or in the form of solutions turns. Organic solvents are suitable as solvents. Aromatic hydrocarbons, such as toluene, Xylene, dodecylbenzene, diisopropylnaphthalene or a mixture of herer aromatics, which is sold under the name Shellsol® AB (Shell) is customary to use. To ensure a high viscosity of the resul avoiding solutions, one generally chooses one Concentration of benzaldehydes I from 5 to 80% by weight, based on the solution.
Zur Verbesserung der Löslichkeit können auch noch weitere Cosol ventien, z. B. Alkohole, wie Methanol, Ethanol, Propanol, Iso propanol, Butanol, Isobutanol, Pentanol, Hexanol, Heptanol, Octanol, 2-Ethylhexanol oder Cyclohexanol, Glykole, wie Butyl ethylenglykol oder Methylpropylenglykol, Amine, wie Triethylamin, Diisooctylamin, Dicyclohexylamin, Anilin, N-Methylanilin, N,N-Di methylanilin, Toluidin oder Xylidin, Alkanolamine, wie 3-(2-Meth oxyethoxy)propylamin, o-Kresol, m-Kresol oder p-Kresol, Ketone, wie Diethylketon oder Cyclohexanon, Lactame, wie γ-Butyrolacton, Carbonate, wie Ethylencarbonat oder Propylencarbonat, Phenole, wie t-Butylphenol oder Nonylphenol, Ester, wie Phthalsäuremethyl ester, Phthalsäureethylester, Phthalsäure-(2-ethylhexyl)ester, Essigsäureethylester, Essigsäurebutylester oder Essigsäurecyclo hexylester, Amide, wie N,N-Dimethylformamid, N,N-Diethylacetamid oder N-Methylpyrrolidinon, oder deren Mischungen verwendet wer den.To improve the solubility, other Cosol valves, e.g. B. alcohols, such as methanol, ethanol, propanol, iso propanol, butanol, isobutanol, pentanol, hexanol, heptanol, Octanol, 2-ethylhexanol or cyclohexanol, glycols, such as butyl ethylene glycol or methyl propylene glycol, amines, such as triethylamine, Diisooctylamine, dicyclohexylamine, aniline, N-methylaniline, N, N-di methylaniline, toluidine or xylidine, alkanolamines, such as 3- (2-meth oxyethoxy) propylamine, o-cresol, m-cresol or p-cresol, ketones, such as diethyl ketone or cyclohexanone, lactams such as γ-butyrolactone, Carbonates, such as ethylene carbonate or propylene carbonate, phenols, such as t-butylphenol or nonylphenol, esters such as methyl phthalate esters, ethyl phthalate, (2-ethylhexyl) phthalate, Ethyl acetate, butyl acetate or cycloacetic acid hexyl esters, amides such as N, N-dimethylformamide, N, N-diethylacetamide or N-methylpyrrolidinone, or mixtures thereof who used the.
Mittels den erfindungsgemäß anzuwendenden Benzaldehyden der For mel I gelingt es sehr einfach, markierte Kohlenwasserstoffe nach zuweisen, selbst wenn die Markierungssubstanzen nur in einer Kon zentration von ungefähr 10 ppm oder darunter vorliegen.By means of the benzaldehydes of For mel I is very easy to replenish labeled hydrocarbons assign, even if the labeling substances only in one con concentration of about 10 ppm or less.
Der Nachweis der Anwesenheit der als Markierungsstoffe angewand ten Verbindungen der Formel I in Kohlenwasserstoffen gelingt vor teilhaft, wenn man den Kohlenwasserstoff mit einem wäßrig-alkoho lischen oder alkoholischem Medium behandelt, das ein Pyryliumsalz der Formel II und/oder ein Indol der Formel III, eine Protonsäure und gegebenenfalls ein Halogenid der Metalle Zink, Aluminium oder Zinn enthält. Bei der Verwendung von wäßrig-alkoholischen Medien beträgt das Gewichtsverhältnis Wasser : Alkohol 0,5 : 1 bis 4 : 1, vorzugsweise ca. 1 : 1. Es resultiert eine deutlich sicht bare Farbänderung der wäßrig-alkoholischen Phase. Evidence of the presence of applied as marking substances Compounds of formula I succeed in hydrocarbons partial if you mix the hydrocarbon with an aqueous alcohol tical or alcoholic medium treated with a pyrylium salt of formula II and / or an indole of formula III, a protonic acid and optionally a halide of the metals zinc, aluminum or Contains tin. When using aqueous-alcoholic media the weight ratio water: alcohol is 0.5: 1 to 4: 1, preferably approx. 1: 1. A clear view results bare color change of the aqueous-alcoholic phase.
Geeignete Alkohole sind z. B. Ethanol, Propanol, Isopropanol, 1-Methoxypropan-2-ol, Ethylenglykol oder 1,2- oder 1,3-Propylen glykol. Die Verwendung von Ethanol ist bevorzugt.Suitable alcohols are e.g. B. ethanol, propanol, isopropanol, 1-methoxypropan-2-ol, ethylene glycol or 1,2- or 1,3-propylene glycol. The use of ethanol is preferred.
Geeignete Protonsäuren für die erfindungsgemäßen Verfahren sind insbesondere sogenannte starke Säuren, d. h. Protonsäuren deren pKa-Wert 3,5 ist. Als solche Säuren kommen beispielsweise anor ganische oder organische Säuren, wie Perchlorsäure, Iodwasser stoffsäure, Chlorwasserstoffsäure, Bromwasserstoffsäure, Fluß säure, Schwefelsäure, Salpetersäure, Phosphorsäure, Benzolsulfon säure, Toluolsulfonsäure, Naphthalinsulfonsäure, Methansulfon säure, Oxalsäure, Maleinsäure, Chloressigsäure, Dichloressigsäure oder Bromessigsäure in Betracht. In manchen Fällen kann es von Vorteil sein, diese Säuren, z. B. durch Zugabe von Essigsäure, ab zupuffern.Suitable protonic acids for the processes according to the invention are in particular so-called strong acids, d. H. Protonic acids thereof pKa is 3.5. Examples of such acids are anor ganic or organic acids, such as perchloric acid, iodine water Substance acid, hydrochloric acid, hydrobromic acid, river acid, sulfuric acid, nitric acid, phosphoric acid, benzenesulfone acid, toluenesulfonic acid, naphthalenesulfonic acid, methanesulfone acid, oxalic acid, maleic acid, chloroacetic acid, dichloroacetic acid or bromoacetic acid. In some cases it can be from Be an advantage of these acids, e.g. B. by adding acetic acid buffer.
Neben o- oder p-Toluolsulfonsäure sind besonders anorganische Säuren hervorzuheben, wobei Salzsäure oder Schwefelsäure beson dere Bedeutung zukommt.In addition to o- or p-toluenesulfonic acid, particularly inorganic ones To emphasize acids, with hydrochloric acid or sulfuric acid in particular their meaning is important.
Geeignete Halogenide der Metalle Zink, Aluminium oder Zinn sind z. B. Zinkchlorid, Zinkbromid, Aluminiumchlorid, Aluminiumbromid oder Zinntetrachlorid. Besonders hervorzuheben ist Zinkchlorid.Suitable halides of the metals zinc, aluminum or tin are e.g. B. zinc chloride, zinc bromide, aluminum chloride, aluminum bromide or tin tetrachloride. Zinc chloride is particularly noteworthy.
Es genügt in der Regel, eine Menge von ungefähr 10 bis 50 ml des erfindungsgemäß markierten Kohlenwasserstoffs mit 1 bis 50 ml einer wäßrig-alkoholischen oder alkoholischen Lösung eines Pyry liumsalzes der Formel II und/oder eines Indols der Formel III, einer Protonsäure, gegebenenfalls unter Zusatz des Metallhaloge nids, auszuschütteln, um eine Farbänderung zu erhalten. Es ist auch möglich, anstelle der Lösung der Protonsäure eine wäßrig-al koholische Lösung des Metallhalogenids alleine zu benutzen, da diese ebenfalls sauer reagiert.It is usually sufficient to use an amount of approximately 10 to 50 ml of the Hydrocarbon labeled according to the invention with 1 to 50 ml an aqueous-alcoholic or alcoholic solution of a pyry lium salt of the formula II and / or an indole of the formula III, a protonic acid, optionally with the addition of the metal halogen nids, shake to get a color change. It is also possible, instead of the solution of the protonic acid, an aqueous al to use alcoholic solution of the metal halide alone because this also reacts sourly.
Die Konzentration der Protonsäure in der wäßrig-alkoholischen oder alkoholischen Lösung beträgt dabei in der Regel 5 bis 50 Gew.-%, vorzugsweise 10 bis 30 Gew.-%. Die Konzentration an Metallhalogenid liegt im allgemeinen bei 0 bis 50 Gew.-%, vor zugsweise bei 5 bis 20 Gew.-%, jeweils bezogen auf das Gewicht der Lösung.The concentration of the protonic acid in the aqueous-alcoholic or alcoholic solution is usually 5 to 50% by weight, preferably 10 to 30% by weight. The concentration on Metal halide is generally 0 to 50% by weight preferably at 5 to 20 wt .-%, each based on the weight the solution.
Ein großer Vorteil der Erfindung besteht darin, daß zwei ver schiedene Methoden zum Nachweis der Benzaldehyde der Formel I be nutzt werden können. Der Nachweis kann daher auch bei möglichen Störeinflüssen (z. B. Zusätze in Dieselkraftstoff) sehr zuverläs sig durchgeführt werden.A great advantage of the invention is that two ver different methods for the detection of benzaldehydes of the formula I be can be used. Evidence can therefore also be provided for possible Very reliable interference (e.g. additives in diesel fuel) be carried out.
Die folgenden Beispiele sollen die Erfindung näher erläutern.The following examples are intended to explain the invention in more detail.
Handelsüblicher Dieselkraftstoff wurde mit jeweils 10 ppm eines Benzaldehyds versetzt. Hierzu wurde der Aldehyd 0,1 gew.-%ig in Toluol vorgelöst und diese Lösung zum Dieselkraftstoff gegeben.Commercial diesel fuel was one with 10 ppm each Benzaldehyde added. For this purpose, the aldehyde was 0.1% by weight in Pre-dissolved toluene and added this solution to the diesel fuel.
In den folgenden Beispielen 1 bis 12 wurden jeweils 10 ml so mar kierten Dieselkraftstoffes mit 2 ml Reagenzlösung versetzt und 5 Minuten geschüttelt. Anschließend wurde 1 ml Wasser zugegeben und weitere 5 Minuten geschüttelt. Die wäßrige Phase zeigte die in der folgenden Tabelle Nr. 1 angegebenen Farben.In the following Examples 1 to 12, 10 ml each were so mar kiert diesel fuel with 2 ml of reagent solution and Shaken for 5 minutes. Then 1 ml of water was added and shaken for another 5 minutes. The aqueous phase showed the colors indicated in the following table No. 1.
Reagenzlösung 1:Reagent solution 1:
5 ml 1-gew.-%ig Indol in Ethanol
5 ml Salzsäure konz.
5 g Zinkchlorid
95 ml Essigsäure5 ml of 1% by weight indole in ethanol
5 ml hydrochloric acid conc.
5 g zinc chloride
95 ml acetic acid
Reagenzlösung 2:Reagent solution 2:
5 ml 1-gew.-%ig 2-Methylindol in Ethanol
5 ml Salzsäure konz.
5 g Zinkchlorid
95 ml Essigsäure5 ml of 1% by weight 2-methylindole in ethanol
5 ml hydrochloric acid conc.
5 g zinc chloride
95 ml acetic acid
Reagenzlösung 3:Reagent solution 3:
5 ml 1-gew.-%ig 2-Phenylindol in Ethanol
5 ml Salzsäure konz.
5 g Zinkchlorid
95 ml Essigsäure5 ml of 1% by weight 2-phenylindole in ethanol
5 ml hydrochloric acid conc.
5 g zinc chloride
95 ml acetic acid
Besonders vorteilhafte Ergebnisse werden erhalten, wenn der Die selkraftstoff zuerst über Kieselgel filtriert wird. Particularly advantageous results are obtained if the die fuel is first filtered through silica gel.
Ähnlich günstige Ergebnisse werden erzielt, wenn man die in der folgenden Tabelle Nr. 2 aufgeführten Benzaldehyde als Markie rungsmittel anwendet.Similar favorable results can be achieved if you look at the following Table No. 2 listed benzaldehydes as Markie applies.
Handelsüblicher Dieselkraftstoff wurde mit jeweils 10 ppm Benzal dehyd versetzt. Hierzu wurde der Benzaldehyd 0,1-gew.-%ig in Toluol vorgelöst und diese Lösung zum Dieselkraftstoff gegeben.Commercial diesel fuel was with 10 ppm benzal dehydrated. For this purpose, the benzaldehyde was 0.1% by weight in Pre-dissolved toluene and added this solution to the diesel fuel.
In den Beispielen 21 bis 30 wurden jeweils 10 ml des markierten Dieselkraftstoffes mit 2 ml Reagenzlösung 4 versetzt und 5 Minu ten unter Rückfluß erhitzt. Anschließend wurde 1 ml Wasser/Etha nol (1 : 1 v/v) zugegeben und weitere 5 Minuten geschüttelt. Die wäßrige Phase zeigte die in der folgenden Tabelle Nr. 3 angege bene Farbe.In Examples 21 to 30 10 ml each of the labeled Diesel fuel mixed with 2 ml of reagent solution 4 and 5 minutes heated under reflux. Then 1 ml of water / Etha nol (1: 1 v / v) added and shaken for a further 5 minutes. The aqueous phase showed that indicated in the following Table No. 3 level color.
Reagenzlösung 4:Reagent solution 4:
5 ml Benzopyryliumsalz der Formel5 ml of benzopyrylium salt of the formula
1-gew.-%ig in Wasser
25 ml Salzsäure konz.
225 ml Essigsäure1% by weight in water
25 ml hydrochloric acid conc.
225 ml acetic acid
Ähnlich günstige Ergebnisse werden erzielt, wenn man das in Reagenzlösung 5 enthaltene Benzopyryliumsalz durch das der FormelSimilar favorable results are achieved if you do this in Reagent solution 5 contained benzopyrylium salt by that of the formula
ersetzt.replaced.
Claims (5)
der Ring A benzoanelliert sein kann und
R¹, R² und R³ unabhängig voneinander jeweils Wasserstoff, Hydroxy, C₁-C₁₅-Alkyl, C₁-C₁₅-Alkoxy, Cyano, Nitro oder einen Rest der Formel NR⁴R⁵ oder COOR⁶ bedeuten, worin
R⁴ für Wasserstoff oder C₁-C₁₅-Alkyl, das durch 1 bis 4 Sauerstoffatome in Etherfunktion unterbrochen sein kann und gegebenenfalls durch Phenyl substituiert ist,
R⁵ für C₁-C₁₅-Alkyl, das durch 1 bis 4 Sauerstoffatome in Etherfunktion unterbrochen sein kann und gegebe nenfalls durch Phenyl substituiert ist, oder-einen Rest der Formel L-NX¹X², worin L die Bedeutung von C₂-C₈-Alkylen und X¹ und X² unabhängig voneinander jeweils die Bedeutung von C₁-C₆-Alkyl oder zusammen mit dem sie verbindenden Stickstoffatom die Bedeutung eines 5- oder 6-gliedrigen gesättigten heterocycli schen Rests, der noch ein Sauerstoffatom im Ring ent halten kann, besitzen, und
R⁶ für Wasserstoff, C₁-C₁₅-Alkyl, das durch 1 bis 4 Sauerstoffatome in Etherfunktion unterbrochen sein kann, oder für einen Rest der Formel L-NX¹X², worin L, X¹ und X² jeweils die obengenannte Bedeutung be sitzen, stehen,
als Markierungsmittel für Kohlenwasserstoffe. 1. Use of benzyldehydes of the formula I in the
the ring A can be fused to benzo and
R¹, R² and R³ each independently represent hydrogen, hydroxy, C₁-C₁₅ alkyl, C₁-C₁₅ alkoxy, cyano, nitro or a radical of the formula NR⁴R⁵ or COOR⁶, in which
R⁴ represents hydrogen or C₁-C₁₅ alkyl, which can be interrupted by 1 to 4 oxygen atoms in ether function and is optionally substituted by phenyl,
R⁵ for C₁-C₁₅-alkyl, which can be interrupted by 1 to 4 oxygen atoms in ether function and optionally substituted by phenyl, or -a radical of the formula L-NX¹X², where L is C₂-C₈-alkylene and X¹ and X² independently of one another each have the meaning of C₁-C₆-alkyl or, together with the nitrogen atom connecting them, have the meaning of a 5- or 6-membered saturated heterocyclic radical which may still contain an oxygen atom in the ring, and
R⁶ represents hydrogen, C₁-C₁₅-alkyl, which can be interrupted by 1 to 4 oxygen atoms in ether function, or a radical of the formula L-NX¹X², in which L, X¹ and X² each have the abovementioned meaning,
as a marking agent for hydrocarbons.
und gegebenenfalls ein Halogenid der Metalle Zink, Aluminium oder Zinn enthält.4. A method for detecting the presence of benzaldehydes of the formula I according to claim 1 in hydrocarbons, characterized in that the hydrocarbon is treated with an aqueous alcoholic or alcoholic medium which is a protonic acid, at least one compound from the group of compounds consisting of substituted pyrylium salts of formula II in the R⁷ for C₁-C₈ alkyl, phenyl, C₁-C₅ alkoxy or halogen and R⁸ for methyl or R⁷ and R⁸ stand together for 1,4-butylene and the ring B can be fused by a benzene ring and optionally by C₁ -C₄-alkyl, pyrrolidino, piperidino, morpholino, chlorine or bromine or in ring position 7 if appropriate also by hydroxy, C₁-C₄-alkoxy, C₁-C₅-mono- or dialkylamino, which in turn can each be substituted by chlorine or phenyl, is substituted and X⊖ denotes an anion, and indoles of the formula III in which R⁹ and R¹⁰ each independently represent hydrogen, a radical of the formula NR⁴R⁵, where R⁴ and R⁵ each have the meaning given in Claim 1, are C₁-C₈-alkyl, phenyl, C₁-C₅-alkoxy or halogen,
and optionally containing a halide of the metals zinc, aluminum or tin.
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4424712A DE4424712A1 (en) | 1994-07-13 | 1994-07-13 | Use of benzaldehydes to mark hydrocarbons |
| CA002195019A CA2195019A1 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
| JP8504633A JPH10502693A (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehyde to mark hydrocarbons |
| HU9700062A HUT76687A (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
| BR9508401A BR9508401A (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes benzaldehyde and hydrocarbon detection process with a marker |
| MX9700365A MX9700365A (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons. |
| CZ9795A CZ9597A3 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehyde derivative for labelling hydrocarbons, method of detecting presence of the benzaldehyde derivative in hydrocarbons and hydrocarbons in which the benzaldehyde derivative is comprised |
| AU29263/95A AU686838B2 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
| PL95318378A PL318378A1 (en) | 1994-07-13 | 1995-07-03 | Application of benzaldehydes for labelling hydrocarbons |
| KR1019970700194A KR970704860A (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehyde for hydrocarbon labeling |
| PCT/EP1995/002558 WO1996002613A1 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
| EP95924960A EP0770119A1 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehydes to mark hydrocarbons |
| SK51-97A SK5197A3 (en) | 1994-07-13 | 1995-07-03 | Use of benzaldehyde derivative to mark hydrocarbons, proofing method for the benzaldehyde derivative presence in hydrocarbons and hydrocarbons containing the benzaldehyde derivative |
| IL11444295A IL114442A0 (en) | 1994-07-13 | 1995-07-04 | Use of benzaldehydes for marking hydrocarbons |
| TR95/00823A TR199500823A2 (en) | 1994-07-13 | 1995-07-06 | Using benzaldehydes to mark hydrocarbons. |
| CO95030617A CO4600746A1 (en) | 1994-07-13 | 1995-07-12 | USE OF BENZALDEHYDE FOR THE MARKING OF HYDROCARBONS |
| NO970126A NO970126L (en) | 1994-07-13 | 1997-01-10 | Use of benzal hydrocarbons for marking hydrocarbons |
| FI970108A FI970108A (en) | 1994-07-13 | 1997-01-10 | Use of benzaldehydes for the labeling of hydrocarbons |
| BG101156A BG101156A (en) | 1994-07-13 | 1997-01-21 | Use of benzaldehydes to mark hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4424712A DE4424712A1 (en) | 1994-07-13 | 1994-07-13 | Use of benzaldehydes to mark hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4424712A1 true DE4424712A1 (en) | 1996-01-18 |
Family
ID=6523046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4424712A Withdrawn DE4424712A1 (en) | 1994-07-13 | 1994-07-13 | Use of benzaldehydes to mark hydrocarbons |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0770119A1 (en) |
| JP (1) | JPH10502693A (en) |
| KR (1) | KR970704860A (en) |
| AU (1) | AU686838B2 (en) |
| BG (1) | BG101156A (en) |
| BR (1) | BR9508401A (en) |
| CA (1) | CA2195019A1 (en) |
| CO (1) | CO4600746A1 (en) |
| CZ (1) | CZ9597A3 (en) |
| DE (1) | DE4424712A1 (en) |
| FI (1) | FI970108A (en) |
| HU (1) | HUT76687A (en) |
| IL (1) | IL114442A0 (en) |
| MX (1) | MX9700365A (en) |
| NO (1) | NO970126L (en) |
| PL (1) | PL318378A1 (en) |
| SK (1) | SK5197A3 (en) |
| TR (1) | TR199500823A2 (en) |
| WO (1) | WO1996002613A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19538121C1 (en) * | 1995-10-13 | 1997-02-27 | Dornier Gmbh Lindauer | Warp tensioner useful for loom esp. for tension sensitive yarns |
| WO2002020500A2 (en) * | 2000-09-01 | 2002-03-14 | Icos Corporation | Materials and methods to potentiate cancer treatment |
| WO2003091361A2 (en) * | 2002-04-26 | 2003-11-06 | Bp Oil International Limited | Method and apparatus for improving the oxidative thermal stability of distillate fuel |
| US8404681B2 (en) | 2003-03-24 | 2013-03-26 | Luitpold Pharmaceuticals, Inc. | Xanthones, thioxanthones and acridinones as DNA-PK inhibitors |
| US20150323515A1 (en) * | 2013-11-05 | 2015-11-12 | Spectrum Tracer Services, Llc | Method and composition for hydraulic fracturing and for tracing petroleum production |
| US10017684B2 (en) | 2016-04-20 | 2018-07-10 | Spectrum Tracer Services, Llc | Method and compositions for hydraulic fracturing and for tracing formation water |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2738154A1 (en) * | 2012-11-30 | 2014-06-04 | Inter-Euro Technology Limited | Improved fuel markers |
| WO2022161960A1 (en) | 2021-01-29 | 2022-08-04 | Basf Se | A method of marking fuels |
| EP4327073A1 (en) | 2021-04-20 | 2024-02-28 | Basf Se | A method of detecting one or more markers in a petroleum fuel using a photoacoustic detector |
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| FR1450273A (en) * | 1965-10-18 | 1966-05-06 | Warner Lambert Pharmaceutical | Preparation usable for the detection of indole produced by microorganisms |
| US3930108A (en) * | 1974-11-21 | 1975-12-30 | Moore Business Forms Inc | 9-(4-Aminophenyl polymethine)-9-xanthenol compounds and pressure sensitive system therewith |
| US5079127A (en) * | 1982-04-06 | 1992-01-07 | Canon Kabushiki Kaisha | Optical recording medium and process for recording thereupon |
| DE3608215A1 (en) * | 1986-03-12 | 1987-09-17 | Basf Ag | NEW BENZOPYRANS AND THEIR USE IN RECORDING SYSTEMS |
| JPH0630626B2 (en) * | 1987-07-24 | 1994-04-27 | テルモ株式会社 | Indole productivity test reagent |
| DE3724757A1 (en) * | 1987-07-25 | 1989-02-09 | Basf Ag | BENZOPYRAN DERIVATIVES |
| GB8802237D0 (en) * | 1988-02-02 | 1988-03-02 | Shell Int Research | Detection of chemicals by immunoassay |
| FR2650606B1 (en) * | 1989-08-07 | 1992-04-30 | Aussedat Rey | INFALSIFIABLE SECURITY PAPER AND AQUEOUS OR ORGANIC COMPOSITION USEFUL, IN PARTICULAR FOR MAKING PAPER INFALSIFIABLE |
| DE4238994A1 (en) * | 1992-11-19 | 1994-05-26 | Basf Ag | Aniline as a marking agent for mineral oils |
-
1994
- 1994-07-13 DE DE4424712A patent/DE4424712A1/en not_active Withdrawn
-
1995
- 1995-07-03 PL PL95318378A patent/PL318378A1/en unknown
- 1995-07-03 CA CA002195019A patent/CA2195019A1/en not_active Abandoned
- 1995-07-03 SK SK51-97A patent/SK5197A3/en unknown
- 1995-07-03 AU AU29263/95A patent/AU686838B2/en not_active Expired - Fee Related
- 1995-07-03 JP JP8504633A patent/JPH10502693A/en active Pending
- 1995-07-03 HU HU9700062A patent/HUT76687A/en unknown
- 1995-07-03 KR KR1019970700194A patent/KR970704860A/en not_active Application Discontinuation
- 1995-07-03 BR BR9508401A patent/BR9508401A/en not_active Application Discontinuation
- 1995-07-03 EP EP95924960A patent/EP0770119A1/en not_active Withdrawn
- 1995-07-03 CZ CZ9795A patent/CZ9597A3/en unknown
- 1995-07-03 MX MX9700365A patent/MX9700365A/en unknown
- 1995-07-03 WO PCT/EP1995/002558 patent/WO1996002613A1/en not_active Application Discontinuation
- 1995-07-04 IL IL11444295A patent/IL114442A0/en unknown
- 1995-07-06 TR TR95/00823A patent/TR199500823A2/en unknown
- 1995-07-12 CO CO95030617A patent/CO4600746A1/en unknown
-
1997
- 1997-01-10 FI FI970108A patent/FI970108A/en unknown
- 1997-01-10 NO NO970126A patent/NO970126L/en unknown
- 1997-01-21 BG BG101156A patent/BG101156A/en unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19538121C1 (en) * | 1995-10-13 | 1997-02-27 | Dornier Gmbh Lindauer | Warp tensioner useful for loom esp. for tension sensitive yarns |
| WO2002020500A2 (en) * | 2000-09-01 | 2002-03-14 | Icos Corporation | Materials and methods to potentiate cancer treatment |
| WO2002020500A3 (en) * | 2000-09-01 | 2003-07-31 | Icos Corp | Materials and methods to potentiate cancer treatment |
| US7179912B2 (en) | 2000-09-01 | 2007-02-20 | Icos Corporation | Materials and methods to potentiate cancer treatment |
| US8242115B2 (en) | 2000-09-01 | 2012-08-14 | Luitpold Pharmaceuticals, Inc. | Materials and methods to potentiate cancer treatment |
| WO2003091361A2 (en) * | 2002-04-26 | 2003-11-06 | Bp Oil International Limited | Method and apparatus for improving the oxidative thermal stability of distillate fuel |
| WO2003091361A3 (en) * | 2002-04-26 | 2004-03-04 | Bp Oil Int | Method and apparatus for improving the oxidative thermal stability of distillate fuel |
| US8404681B2 (en) | 2003-03-24 | 2013-03-26 | Luitpold Pharmaceuticals, Inc. | Xanthones, thioxanthones and acridinones as DNA-PK inhibitors |
| US20150323515A1 (en) * | 2013-11-05 | 2015-11-12 | Spectrum Tracer Services, Llc | Method and composition for hydraulic fracturing and for tracing petroleum production |
| US9594070B2 (en) * | 2013-11-05 | 2017-03-14 | Spectrum Tracer Services, Llc | Method using halogenated benzoic acid esters and aldehydes for hydraulic fracturing and for tracing petroleum production |
| US10017684B2 (en) | 2016-04-20 | 2018-07-10 | Spectrum Tracer Services, Llc | Method and compositions for hydraulic fracturing and for tracing formation water |
Also Published As
| Publication number | Publication date |
|---|---|
| PL318378A1 (en) | 1997-06-09 |
| HUT76687A (en) | 1997-10-28 |
| JPH10502693A (en) | 1998-03-10 |
| CO4600746A1 (en) | 1998-05-08 |
| CA2195019A1 (en) | 1996-02-01 |
| AU2926395A (en) | 1996-02-16 |
| BR9508401A (en) | 1998-05-19 |
| IL114442A0 (en) | 1995-11-27 |
| TR199500823A2 (en) | 1996-06-21 |
| FI970108A (en) | 1997-03-12 |
| NO970126D0 (en) | 1997-01-10 |
| CZ9597A3 (en) | 1997-06-11 |
| KR970704860A (en) | 1997-09-06 |
| WO1996002613A1 (en) | 1996-02-01 |
| NO970126L (en) | 1997-03-10 |
| SK5197A3 (en) | 1997-08-06 |
| MX9700365A (en) | 1997-04-30 |
| FI970108A0 (en) | 1997-01-10 |
| BG101156A (en) | 1997-08-29 |
| EP0770119A1 (en) | 1997-05-02 |
| AU686838B2 (en) | 1998-02-12 |
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