DE1909957A1 - Verfahren zur Reinigung von rohem Adipinsaeurenitril - Google Patents

Verfahren zur Reinigung von rohem Adipinsaeurenitril

Info

Publication number: DE1909957A1
Authority: DE; Germany
Prior art keywords: oxide; potassium; sodium; manganese; ppm
Prior art date: 1968-02-29
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.): Pending

Application number

DE19691909957

Other languages

German (de)

English (en)

Inventor

Takeaki Iwamoto

Maomi Seko

Shikazo Seno

Yasunobu Takahashi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Asahi Chemical Industry Co Ltd

Original Assignee

Asahi Chemical Industry Co Ltd

Priority date (The priority date 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 date listed.)

1968-02-29

Filing date

1969-02-27

Publication date

1969-09-04

1969-02-27 Application filed by Asahi Chemical Industry Co Ltd filed Critical Asahi Chemical Industry Co Ltd

1969-09-04 Publication of DE1909957A1 publication Critical patent/DE1909957A1/de

Status Pending legal-status Critical Current

Links

BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 title claims description 30
238000000034 method Methods 0.000 title claims description 18
238000000746 purification Methods 0.000 title description 2
239000011734 sodium Substances 0.000 claims description 29
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 19
229910052708 sodium Inorganic materials 0.000 claims description 19
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 18
229910052700 potassium Inorganic materials 0.000 claims description 18
239000011591 potassium Substances 0.000 claims description 18
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 10
239000012286 potassium permanganate Substances 0.000 claims description 8
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 8
GEYXPJBPASPPLI-UHFFFAOYSA-N manganese(iii) oxide Chemical compound O=[Mn]O[Mn]=O GEYXPJBPASPPLI-UHFFFAOYSA-N 0.000 claims description 6
HYERJXDYFLQTGF-UHFFFAOYSA-N rhenium Chemical compound [Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re] HYERJXDYFLQTGF-UHFFFAOYSA-N 0.000 claims description 6
PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims description 6
-1 anions chromate Chemical class 0.000 claims description 5
239000011651 chromium Substances 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
239000012535 impurity Substances 0.000 claims description 5
LBSANEJBGMCTBH-UHFFFAOYSA-N manganate Chemical compound [O-][Mn]([O-])(=O)=O LBSANEJBGMCTBH-UHFFFAOYSA-N 0.000 claims description 5
AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 claims description 5
235000015393 sodium molybdate Nutrition 0.000 claims description 5
239000011684 sodium molybdate Substances 0.000 claims description 5
TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 claims description 5
PMJNEQWWZRSFCE-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-(thiophen-2-ylmethyl)propanoic acid Chemical compound CCOC(=O)C(C(O)=O)CC1=CC=CS1 PMJNEQWWZRSFCE-UHFFFAOYSA-N 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
229940037003 alum Drugs 0.000 claims description 3
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 3
229910052804 chromium Inorganic materials 0.000 claims description 3
238000004140 cleaning Methods 0.000 claims description 3
235000007079 manganese sulphate Nutrition 0.000 claims description 3
239000011702 manganese sulphate Substances 0.000 claims description 3
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
229910052750 molybdenum Inorganic materials 0.000 claims description 3
239000011733 molybdenum Substances 0.000 claims description 3
229910052702 rhenium Inorganic materials 0.000 claims description 3
229910052721 tungsten Inorganic materials 0.000 claims description 3
239000010937 tungsten Substances 0.000 claims description 3
JYLNVJYYQQXNEK-UHFFFAOYSA-N 3-amino-2-(4-chlorophenyl)-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(CN)C1=CC=C(Cl)C=C1 JYLNVJYYQQXNEK-UHFFFAOYSA-N 0.000 claims description 2
HVCXHPPDIVVWOJ-UHFFFAOYSA-N [K].[Mn] Chemical compound [K].[Mn] HVCXHPPDIVVWOJ-UHFFFAOYSA-N 0.000 claims description 2
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims description 2
BNBLBRISEAQIHU-UHFFFAOYSA-N disodium dioxido(dioxo)manganese Chemical compound [Na+].[Na+].[O-][Mn]([O-])(=O)=O BNBLBRISEAQIHU-UHFFFAOYSA-N 0.000 claims description 2
229940099596 manganese sulfate Drugs 0.000 claims description 2
KVGMATYUUPJFQL-UHFFFAOYSA-N manganese(2+) oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[Mn++].[Mn++].[Mn++] KVGMATYUUPJFQL-UHFFFAOYSA-N 0.000 claims description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
150000002739 metals Chemical class 0.000 claims description 2
AQRDGTBNWBTFKJ-UHFFFAOYSA-N molybdenum;dihydrate Chemical compound O.O.[Mo] AQRDGTBNWBTFKJ-UHFFFAOYSA-N 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
HRLYFPKUYKFYJE-UHFFFAOYSA-N tetraoxorhenate(2-) Chemical compound [O-][Re]([O-])(=O)=O HRLYFPKUYKFYJE-UHFFFAOYSA-N 0.000 claims description 2
150000002736 metal compounds Chemical class 0.000 claims 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims 2
GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 claims 2
QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims 2
241001279686 Allium moly Species 0.000 claims 1
150000001339 alkali metal compounds Chemical class 0.000 claims 1
150000001450 anions Chemical class 0.000 claims 1
OVHDZBAFUMEXCX-UHFFFAOYSA-N benzyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1 OVHDZBAFUMEXCX-UHFFFAOYSA-N 0.000 claims 1
UAJMEYCHOVZMRB-UHFFFAOYSA-N magnesium dioxido(dioxo)manganese Chemical compound [Mg+2].[O-][Mn]([O-])(=O)=O UAJMEYCHOVZMRB-UHFFFAOYSA-N 0.000 claims 1
229910044991 metal oxide Inorganic materials 0.000 claims 1
150000004706 metal oxides Chemical class 0.000 claims 1
ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten(VI) oxide Inorganic materials O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 description 38
229910052783 alkali metal Inorganic materials 0.000 description 19
150000001340 alkali metals Chemical class 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 15
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000000243 solution Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 10
229910052784 alkaline earth metal Inorganic materials 0.000 description 9
150000001342 alkaline earth metals Chemical class 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 6
239000011572 manganese Substances 0.000 description 6
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 5
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
FRMJZJUVLPFLAB-UHFFFAOYSA-N 2-iminocyclopentane-1-carbonitrile Chemical compound N=C1CCCC1C#N FRMJZJUVLPFLAB-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000006471 dimerization reaction Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 3
NTFJXDRAVMOYBG-UHFFFAOYSA-N 2-(2,2-dicyanoethoxymethyl)propanedinitrile Chemical compound N#CC(C#N)COCC(C#N)C#N NTFJXDRAVMOYBG-UHFFFAOYSA-N 0.000 description 2
UNANDJIJRBQOOF-UHFFFAOYSA-N 5-(dimethoxymethyl)-1,3-benzodioxole Chemical compound COC(OC)C1=CC=C2OCOC2=C1 UNANDJIJRBQOOF-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
QXYJCZRRLLQGCR-UHFFFAOYSA-N dioxomolybdenum Chemical compound O=[Mo]=O QXYJCZRRLLQGCR-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052748 manganese Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052701 rubidium Inorganic materials 0.000 description 2
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000011949 solid catalyst Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
DZKDPOPGYFUOGI-UHFFFAOYSA-N tungsten(iv) oxide Chemical compound O=[W]=O DZKDPOPGYFUOGI-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SIWNEELMSUHJGO-UHFFFAOYSA-N 2-(4-bromophenyl)-4,5,6,7-tetrahydro-[1,3]oxazolo[4,5-c]pyridine Chemical compound C1=CC(Br)=CC=C1C(O1)=NC2=C1CCNC2 SIWNEELMSUHJGO-UHFFFAOYSA-N 0.000 description 1
FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 1
101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000065675 Cyclops Species 0.000 description 1
241001026509 Kata Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
241001460678 Napo <wasp> Species 0.000 description 1
YLWSLXWWQRXXMX-UHFFFAOYSA-N [Mo](=O)(=O)=O.[Na] Chemical compound [Mo](=O)(=O)=O.[Na] YLWSLXWWQRXXMX-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
239000003513 alkali Substances 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
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
OIDPCXKPHYRNKH-UHFFFAOYSA-J chrome alum Chemical compound [K]OS(=O)(=O)O[Cr]1OS(=O)(=O)O1 OIDPCXKPHYRNKH-UHFFFAOYSA-J 0.000 description 1
BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
IAQWMWUKBQPOIY-UHFFFAOYSA-N chromium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Cr+4] IAQWMWUKBQPOIY-UHFFFAOYSA-N 0.000 description 1
AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium(IV) oxide Inorganic materials O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005868 electrolysis reaction Methods 0.000 description 1
239000003792 electrolyte Substances 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
150000002466 imines Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical class [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 1
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
VVRQVWSVLMGPRN-UHFFFAOYSA-N oxotungsten Chemical class [W]=O VVRQVWSVLMGPRN-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
WXBOMIKEWRRKBB-UHFFFAOYSA-N rhenium(iv) oxide Chemical compound O=[Re]=O WXBOMIKEWRRKBB-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DE19691909957 1968-02-29 1969-02-27 Verfahren zur Reinigung von rohem Adipinsaeurenitril Pending DE1909957A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP1307968		1968-02-29
JP6219668		1968-08-31

Publications (1)

Publication Number	Publication Date
DE1909957A1 true DE1909957A1 (de)	1969-09-04

Family

ID=26348801

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19691909957 Pending DE1909957A1 (de)	1968-02-29	1969-02-27	Verfahren zur Reinigung von rohem Adipinsaeurenitril

Country Status (8)

Country	Link
BE (1)	BE728688A (fi)
CH (1)	CH525192A (fi)
DE (1)	DE1909957A1 (fi)
FR (1)	FR2002928A1 (fi)
GB (1)	GB1200872A (fi)
LU (1)	LU58105A1 (fi)
NL (1)	NL6902992A (fi)
SU (1)	SU368744A3 (fi)

1969
- 1969-02-20 BE BE728688D patent/BE728688A/xx unknown
- 1969-02-26 NL NL6902992A patent/NL6902992A/xx unknown
- 1969-02-27 DE DE19691909957 patent/DE1909957A1/de active Pending
- 1969-02-27 LU LU58105D patent/LU58105A1/xx unknown
- 1969-02-27 GB GB10594/69A patent/GB1200872A/en not_active Expired
- 1969-02-28 FR FR6905385A patent/FR2002928A1/fr not_active Withdrawn
- 1969-02-28 CH CH303869A patent/CH525192A/de not_active IP Right Cessation
- 1969-02-28 SU SU1307648A patent/SU368744A3/ru active

Also Published As

Publication number	Publication date
GB1200872A (en)	1970-08-05
BE728688A (fi)	1969-08-01
NL6902992A (fi)	1969-09-02
SU368744A3 (fi)	1973-01-26
FR2002928A1 (fi)	1969-10-31
LU58105A1 (fi)	1969-06-03
CH525192A (de)	1972-07-15

Publication	Publication Date	Title
DE1302398B (fi)	1970-10-15
US2087691A (en)	1937-07-20	Process of catalytically hydeogen
CH436326A (de)	1967-05-31	Verfahren zur Herstellung von Aminen
DE2926641C2 (de)	1983-11-17	Molybdän enthaltender Raney-Nickel-Katalysator und seine Verwendung zur katalytischen Hydrierung von Butindiol
DE2722741A1 (de)	1977-12-08	Verfahren zur stereoselektiven hydrierung von alpha-pinen
DE1909957A1 (de)	1969-09-04	Verfahren zur Reinigung von rohem Adipinsaeurenitril
DE1952895A1 (de)	1970-09-10	Verfahren zur Herstellung heterocyclischer Verbindungen
DE3003730C2 (fi)	1989-03-16
DE2307541A1 (de)	1973-09-06	Verfahren zur hydroxymethylierung von in 6-stellung substituierten 3-hydroxypyridinen in 2-stellung
DE1914112A1 (de)	1969-10-02	Verfahren zur Herstellung von Aldehyden
DE659927C (de)	1938-05-13	Verfahren zur Herstellung von Alkyl- oder Aralkylhalogeniden
DE896196C (de)	1953-11-09	Verfahren zur Herstellung von Melamin
EP0497796B1 (de)	1994-06-22	Verfahren zur herstellung von fluorbenzolen
DE966055C (de)	1957-07-04	Verfahren zur Herstellung von Oximen aliphatischer und cycloaliphatischer Ketone
DE962255C (de)	1957-04-18	Verfahren zur Herstellung von aromatischen Aminen
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