CN104326905B - 一种芳基烷基羧酸聚氧乙烯酯及其制备方法和应用 - Google Patents
一种芳基烷基羧酸聚氧乙烯酯及其制备方法和应用 Download PDFInfo
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- CN104326905B CN104326905B CN201410466390.1A CN201410466390A CN104326905B CN 104326905 B CN104326905 B CN 104326905B CN 201410466390 A CN201410466390 A CN 201410466390A CN 104326905 B CN104326905 B CN 104326905B
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- Prior art keywords
- carboxylic acid
- acid
- aryl alkyl
- alkyl carboxylic
- preparation
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- -1 aryl alkyl carboxylic acid Chemical class 0.000 title claims abstract description 97
- 229920003171 Poly (ethylene oxide) Polymers 0.000 title claims abstract description 31
- 150000002148 esters Chemical class 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 238000007046 ethoxylation reaction Methods 0.000 claims abstract description 5
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 8
- 239000011973 solid acid Substances 0.000 claims description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005642 Oleic acid Substances 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
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- 238000002485 combustion reaction Methods 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
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- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 3
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 239000012974 tin catalyst Substances 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 239000002608 ionic liquid Substances 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
- 238000007171 acid catalysis Methods 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000010687 lubricating oil Substances 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 239000001119 stannous chloride Substances 0.000 claims 1
- 235000011150 stannous chloride Nutrition 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 230000032050 esterification Effects 0.000 abstract description 5
- 238000005886 esterification reaction Methods 0.000 abstract description 5
- 239000011248 coating agent Substances 0.000 abstract description 2
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- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
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- 239000004094 surface-active agent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001272567 Hominoidea Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- UAUDZVJPLUQNMU-KTKRTIGZSA-N erucamide Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-KTKRTIGZSA-N 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- VPGSXIKVUASQIY-UHFFFAOYSA-N 1,2-dibutylnaphthalene Chemical compound C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 VPGSXIKVUASQIY-UHFFFAOYSA-N 0.000 description 1
- ZMXIYERNXPIYFR-UHFFFAOYSA-N 1-ethylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=CC2=C1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- SNEYJZBZIICCIN-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)S(=O)(=O)O.C(CCCCCCCCCCC)[Na] Chemical compound C1(=CC=CC2=CC=CC=C12)S(=O)(=O)O.C(CCCCCCCCCCC)[Na] SNEYJZBZIICCIN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000012356 Product development Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- RJTJVVYSTUQWNI-UHFFFAOYSA-N beta-ethyl naphthalene Natural products C1=CC=CC2=CC(CC)=CC=C21 RJTJVVYSTUQWNI-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-UHFFFAOYSA-J 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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Abstract
本发明公开了一种芳基烷基羧酸聚氧乙烯酯，具有通式Ⅰ结构，制备方法为芳基烷基羧酸聚氧乙烯酯的制备是将烯基羧酸与芳香烃烷基化，得到芳基烷基羧酸，再将芳基烷基羧酸与环氧乙烷进行乙氧基化反应，得到芳基烷基羧酸聚氧乙烯酯；也可以将芳基烷基羧酸与聚乙二醇进行酯化反应，得到芳基烷基羧酸聚氧乙烯酯。芳基烷基羧酸聚氧乙烯酯可用于纺织、涂料、洗涤剂、金属加工等多个领域。
Description
技术领域
本发明涉及一种芳基烷基羧酸聚氧乙烯酯及其制备方法和应用。
背景技术
脂肪酸聚氧乙烯酯是一类用途非常广泛的非离子表面活性剂，可用作纺织、涂料、洗涤剂、金属加工、石油加工等多个领域。制备脂肪酸聚氧乙烯酯所用的羧酸主要来源于动植物油脂，是以C12到C18的脂肪酸为主。
烷基酚聚氧乙烯醚(OP和NP)是一种常用的非离子表面活性剂，在原油乳化、稠油降黏、乳化渣油燃料等方面应用广泛。
欧洲诸国已规定自2005年1月17日起全面禁止使用含有APEO(包含烷基苯酚、乙氧基烷基苯酚醚)的产品，脂肪醇聚氧乙烯醚和支链醇聚氧乙烯醚成为了烷基苯酚聚氧乙烯醚的替代品。
通常原油的化学组分为烷烃、芳香烃、胶质和沥青质。下面列出大庆原油及中国一些原油的馏分组成，见表1和表2。
表1大庆油田原油组成
表2中国一些油田原油馏分组成
具有类似于原油结构的乙氧基非离子表面活性剂，在乳化剂、重油助燃剂、润滑油添加剂、稠油降粘剂等领域应用前景广阔，具有极大的产品开发价值。
发明内容
本发明的目的是提供一种芳基烷基羧酸聚氧乙烯酯，具有通式Ⅰ结构：
其中：m+n为0、1、2……28、29、30的正整数，
p为1、2……9998、9999、10000的正整数，
R为苯基，甲苯基，间二甲苯基，对二甲苯基，邻二甲苯基，乙苯基，正丙基苯基，异丙基苯基，正丁基苯基，异丁基苯基，叔丁基苯基，萘基，甲基萘基，二甲基萘基，乙基萘基，丙基萘基，丁基萘基，联苯基，苯酚基中的一种。
进一步地，在上述技术方案中，m+n优选为8、15、19，更优选为15。
进一步地，在上述技术方案中，p优选为10、11……998、999、1000的正整数，更优选为10、11......29、30的正整数。
进一步地，在上述技术方案中，R优选为间二甲苯基。
本发明的再一目的是提供上述芳基烷基羧酸聚氧乙烯酯的制备方法，技术方案是在酸性催化剂作用下，芳香烃与烯基羧酸的双键发生傅-克烷基化反应，合成出芳基烷基羧酸，芳基烷基羧酸再与环氧乙烷在催化剂作用下进行开环反应，得到芳基烷基羧酸聚氧乙烯酯。
进一步地，在上述技术方案中，芳基烷基羧酸还可与聚乙二醇进行酯化反应，得到芳基烷基羧酸聚氧乙烯酯。
进一步地，在上述技术方案中，本发明的制备芳基烷基羧酸所用的酸性催化剂，为硫酸、氢氟酸、甲基磺酸、三氟甲磺酸、三氟甲磺酸金属盐或负载的三氟甲磺酸根、杂多酸、固体超强酸、酸性沸石、全氟代树脂、离子液体中的任意一种或几种混合物，优选甲基磺酸、三氟甲磺酸金属盐或负载的三氟甲磺酸根，更优选甲基磺酸。
进一步地，在上述技术方案中，芳基烷基羧酸与环氧乙烷进行的乙氧基化反应所用的催化剂为常规的环氧乙烷开环催化剂，所述催化剂选自BF3、SbCI5、SnCI4、固体酸、杂多酸、负载型分子筛催化剂中的任意一种；或选自氢氧化钾、氢氧化钠、甲醇钠、乙醇钠、Mg/AI复合氧化物(MAO)、钡的氧化物与氢氧化物、烷氧基铝磺酸盐、稀有金属烷氧硫酸盐、碱土金属氧化物与磷酸的复合物中的任意一种，优选氢氧化钾、甲醇钠、Mg/AI复合氧化物(MAO)。
进一步地，在上述技术方案中，芳基烷基羧酸与聚乙二醇进行的酯化反应为固体酸催化剂或金属锡类催化剂。固体酸催化剂为选自阳离子交换树脂、分子筛固载化液体酸或金属盐中的任意一种或几种混合物，优选D001-CC树脂、HZSM-5型分子筛、固体磷酸、羰基固体酸、硫酸锆、D061树脂、HY、USY、ReY、H-Beta、丝光沸石、磷鉬酸、硅钨酸中的任意一种或几种混合物；金属锡类催化剂为氧化亚锡、氯化亚锡或草酸亚锡中的任意一种或几种混合物，优选氧化亚锡。
进一步地，在上述技术方案中，本发明所述的烯基羧酸，为十一烯酸：
CH2＝CH(CH2)8COOH、油酸：CH3(CH2)7CH＝CH(CH2)7COOH、芥酸：顺式-13-二十二碳烯酸，优选油酸。
进一步地，在上述技术方案中，所述为芳香烃选自苯，甲苯，间二甲苯，对二甲苯，邻二甲苯，乙苯，正丙基苯，异丙基苯，正丁基苯，异丁基苯，叔丁基苯，萘，甲基萘，二甲基萘，乙基萘，丙基萘，丁基萘，联苯，苯酚中的一种。
进一步地，在上述技术方案中，液体酸甲基磺酸作为催化剂，烯基羧酸与芳香烃的摩尔比为1:1.5-3.5，烯基羧酸与甲基磺酸的摩尔比为1:1.15-2.0；反应温度100-135℃，滴加烯基羧酸，然后反应5小时，水洗至PH值中性，短程蒸馏脱除未反应的原料和其中的饱和酸，得芳基烷基羧酸。
进一步地，在上述技术方案中，本发明所述的芳基烷基羧酸与环氧乙烷进行的开环反应，优选芳基烷基羧酸与环氧乙烷摩尔比为1:10～30。
进一步地，在上述技术方案中，芳基烷基羧酸与聚乙二醇的摩尔比为1:1.05，固体酸做催化剂，所述固体酸催化剂的加入量为原料总质量的0.5-1.0％，抽真空115-135℃脱水反应6小时，过滤除去固体酸催化剂，得产品。
进一步地本发明所述的芳基烷基羧酸与聚乙二醇进行的酯化反应，优选聚乙二醇的分子量为100～8000。
本发明的有益结果是：
1.本发明的芳基烷基羧酸聚氧乙烯酯，可以替代烷基酚聚氧乙烯醚在重油助燃剂、稠油降粘剂等原来使用烷基酚聚氧乙烯醚的领域中的应用；
2.芳基烷基羧酸聚氧乙烯酯相比于脂肪醇聚氧乙烯醚和支链醇聚氧乙烯醚，对原油具有更好的乳化效果，更适合于在原油乳化等领域的应用；
3.芳基烷基羧酸聚氧乙烯酯由于分子量较大，在一定浓度下具有增粘作用，可用于三次采油领域；
4.本发明的芳基烷基羧酸聚氧乙烯酯制备方法转化率高，适合产业化生产。
附图说明
本发明附图2幅，
图1为实施例1制备得到的间二甲苯基十八烷羧酸的红外光谱图；
图2为实施例1制备得到的间二甲苯基十八烷羧酸聚氧乙烯(20)酯飞行时间质谱图。
具体实施方式
下面结合实施例来进一步说明本发明，但并不作为对本发明的限定。
实施例1：
傅-克烷基化反应：
在装有搅拌器、温度计、恒压滴管、冷凝器的1000ml反应瓶中，投入248克间二甲苯(AR)、112克甲基磺酸(AR)，升温至125～130℃，滴加高纯油酸(油酸含量≥75％)220克，滴加时间为5小时，继续反应2小时。降温，水洗至PH值中性，旋转蒸发仪脱除过量的间二甲苯，分子蒸馏脱色，得间二甲苯基十八烷羧酸。液相色谱分析油酸转化率≥90％。
间二甲苯基十八烷羧酸红外光谱图见图1。
在图1中1412cm-1(羧酸O-H弯曲振动)，1710cm-1(羧酸C＝O伸缩振动)；725cm-1(间二取代基C-H面外弯曲振动)，1047cm-1(芳烃C-H面内弯曲振动)，1459cm-1(芳烃C＝C伸缩振动)；2853cm-1(CH2烷烃对称伸缩振动)，2925cm-1(CH2烷烃反对称伸缩振动)。
开环反应：
称取116克间二甲苯基十八烷羧酸和1.5克Mg/AI复合氧化物(MAO)投入1升合成釜中，将合成釜密封，用氮气置换3次。启动搅拌，升温至140℃，启动真空泵抽真空，升温至170℃时停止抽真空。打开进料阀，用氮气将储罐内264克环氧乙烷逐渐压入反应釜中，控制反应温度在140℃～180℃，压力≤0.15MPa，反应4小时。降温，出料，过滤，除去催化剂，得间二甲苯基十八烷羧酸聚氧乙烯(20)酯。
间二甲苯基十八烷羧酸聚氧乙烯(20)酯飞行时间质谱图见图2。
在图2中1mol间二甲苯基十八烷羧酸与20mol环氧乙烷进行加成反应，得到的是呈近似正态分布状态的间二甲苯十八烷羧酸聚氧乙烯酯结构。
实施例2：
傅-克烷基化反应：
同实施例1中。
酯化反应：
在1000ml的反应釜中依次加入380gPEG(聚乙二醇)、350克间二甲苯基十八烷羧酸、5克氧化亚锡，抽真空，开动搅拌后缓缓升温至115℃～135℃，真空度≥-0.098MPa，并在此温度及真空条件下，馏出反应生产的水，反应6小时后已无水馏出，降温出料，过滤除去氧化亚锡得产品间二甲苯基十八烷羧酸聚氧乙烯(400)单酯，间二甲苯基十八烷羧酸转化率达98％。
应用例1
渣油乳化实验：
渣油作为一种重要的燃料应用十分广泛。在渣油体系中加入5％-30％的水、适量的乳化剂得到的油包水型的乳化渣油，在燃烧时，由于“微爆”的作用，燃料雾化程度好，使燃烧速度加快，燃烧效率增加。乳化渣油应用中最关键的问题是乳液的稳定性。
乳化渣油配方1：两性表面活性剂芥酸酰胺基丙基羧基甜菜碱(由芥酸酰胺基丙基叔胺与氯乙酸钠按1:1.1摩尔比投入反应釜，甲醇做溶剂，110℃反应8小时，脱甲醇得产品)0.05％(w/w)，非离子表面活性剂间二甲苯基十八烷羧酸聚氧乙烯(20)脂0.5％(w/w)，燕山石化生产的渣油，油水比为70:30(w/w)，在80℃水浴中采用电动搅拌器充分搅拌30min。将乳状液置于80℃的恒温箱中放置5天，析出水为0。
乳化渣油配方2：阴离子表面活性剂十二烷基萘磺酸钠(由江西斯莫生物化学有限公司提供)0.08％(w/w)，非离子表面活性剂间二甲苯基十八烷羧酸聚氧乙烯(20)脂0.5％(w/w)，燕山石化生产的渣油，油水比为70:30(w/w)，在80℃水浴中采用电动搅拌器充分搅拌30min。将乳状液置于80℃的恒温箱中放置4天，析出水为0。
应用例2
稠油乳化降黏实验：
配方组成：非离子表面活性剂间二甲苯基十八烷羧酸聚氧乙烯(20)脂0.5％，聚合物表面活性剂0.05％，芥酸酰胺基丙基羧基甜菜碱0.08％，河南油田稠油黏度1500mPa.s。
按设定的油水比50:50(w/w)混合均匀，用布氏粘度计测定25℃下的黏度，并测定维持该黏度的稳定时间，降黏率为98％，稳定时间75小时。
Claims (10)
1.一种芳基烷基羧酸聚氧乙烯酯，其特征在于具有通式Ⅰ结构：
其中：m+n为0-30的正整数，
p为1-10000的正整数，
R为苯基，甲苯基，间二甲苯基，对二甲苯基，邻二甲苯基，乙苯基，正丙基苯基，异丙基苯基，正丁基苯基，异丁基苯基，叔丁基苯基，苯酚基中的一种。
2.如权利要求1所述一种芳基烷基羧酸聚氧乙烯酯的制备方法，其特征在于：包括以下步骤：
①烯基羧酸与芳香烃在酸性催化剂作用下进行的烷基化反应，得到芳基烷基羧酸；
②再将芳基烷基羧酸与聚乙二醇在固体酸催化剂或金属锡类催化剂作用下进行的脱水缩合反应，得到芳基烷基羧酸聚氧乙烯酯；或将芳基烷基羧酸与环氧乙烷在催化剂作用下进行乙氧基化反应，得到芳基烷基羧酸聚氧乙烯酯。
3.根据权利要求2所述的制备方法，其特征在于：所述的固体酸催化剂选自阳离子交换树脂、分子筛固载化液体酸或金属盐中的任意一种或几种；所述的金属锡类催化剂选自氧化亚锡、氯化亚锡或草酸亚锡中的任意一种。
4.根据权利要求2所述的制备方法，其特征在于：所述步骤②中，聚乙二醇的分子量为100～8000。
5.根据权利要求2所述的制备方法，其特征在于：所述步骤②乙氧基化反应中芳基烷基羧酸与环氧乙烷的摩尔比为1:5～100。
6.根据权利要求2所述的制备方法，其特征在于，所述步骤②乙氧基化反应中所述催化剂选自BF3、SbCI5、SnCI4、固体酸、杂多酸、负载型分子筛催化剂中的一种；或选自氢氧化钾、氢氧化钠、甲醇钠、乙醇钠、Mg/Al复合氧化物、钡的氧化物与氢氧化物、烷氧基铝磺酸盐、稀有金属烷氧硫酸盐、碱土金属氧化物与磷酸的复合物中的一种。
7.根据权利要求2所述的制备方法，其特征在于：所述步骤①中酸性催化剂选自硫酸、氢氟酸、甲基磺酸、三氟甲磺酸、三氟甲磺酸金属盐或负载的三氟甲磺酸根、杂多酸、固体超强酸、酸性沸石、全氟代树脂、离子液体中的任意一种或几种。
8.根据权利要求2所述的制备方法，其特征在于：所述步骤①中烯基羧酸为十一烯酸、油酸、芥酸中的一种或多种。
9.根据权利要求2所述的制备方法，其特征在于：所述步骤①为油酸与间二甲苯在甲基磺酸催化下进行的烷基化反应。
10.如权利要求1所述的芳基烷基羧酸聚氧乙烯酯在制备乳化剂、重油助燃剂、润滑油添加剂、稠油降粘剂中的应用。
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103641750A (zh) * | 2013-11-28 | 2014-03-19 | 中国石油天然气股份有限公司 | 一种含有芳烷基疏水链和酰胺键连接基团的表面活性剂 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN103320110A (zh) * | 2013-06-26 | 2013-09-25 | 工合聚能(天津)石油精化科技发展有限公司 | 一种稠油和超稠油开采用纳米复合型耐高温助采剂及其制备方法 |
| CN103641750A (zh) * | 2013-11-28 | 2014-03-19 | 中国石油天然气股份有限公司 | 一种含有芳烷基疏水链和酰胺键连接基团的表面活性剂 |
Non-Patent Citations (2)
| Title |
|---|
| Phenolation of vegetable oils;MIHAIL IONESCU等;《J. Serb. Chem. Soc.》;20111231;第76卷(第4期);第591–606页 * |
| 芳基油酸酰胺羟丙基磺基甜菜碱的合成及性能;于涛等;《应用化学》;20121130;第29卷(第11期);第1302-1308页 * |
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