DE2633364A1 - Verfahren zum herstellen von ungesaettigten dinitrilen - Google Patents
Verfahren zum herstellen von ungesaettigten dinitrilenInfo
- Publication number
- DE2633364A1 DE2633364A1 DE19762633364 DE2633364A DE2633364A1 DE 2633364 A1 DE2633364 A1 DE 2633364A1 DE 19762633364 DE19762633364 DE 19762633364 DE 2633364 A DE2633364 A DE 2633364A DE 2633364 A1 DE2633364 A1 DE 2633364A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- bonded
- monoadduct
- diluent
- water
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 229930195733 hydrocarbon Natural products 0.000 claims description 26
- 150000002430 hydrocarbons Chemical class 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000003085 diluting agent Substances 0.000 claims description 21
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 5
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 description 26
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- -1 hydrocarbon radical Chemical class 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 10
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 7
- NETAIQQWYLQFTM-UHFFFAOYSA-N 5-methylhex-5-enenitrile Chemical compound CC(=C)CCCC#N NETAIQQWYLQFTM-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 3
- MXVRFPSJYIKHQF-UHFFFAOYSA-N 2,4-dimethylpent-4-enenitrile Chemical compound N#CC(C)CC(C)=C MXVRFPSJYIKHQF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005580 one pot reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 2
- HWGNERYJKMWNBQ-UHFFFAOYSA-N 5-methylnon-4-enedinitrile Chemical compound N#CCCCC(C)=CCCC#N HWGNERYJKMWNBQ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- ICYKAAVNVLYJCI-UHFFFAOYSA-N (4-ethylphenyl)-diphenylphosphane Chemical compound C1=CC(CC)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ICYKAAVNVLYJCI-UHFFFAOYSA-N 0.000 description 1
- GOZCYJUTCBNJCS-UHFFFAOYSA-N (4-methylphenoxy)-diphenylphosphane Chemical compound C1=CC(C)=CC=C1OP(C=1C=CC=CC=1)C1=CC=CC=C1 GOZCYJUTCBNJCS-UHFFFAOYSA-N 0.000 description 1
- FZQMZRXKWHQJAG-VOTSOKGWSA-N (e)-3,4,4-trimethylpent-2-ene Chemical compound C\C=C(/C)C(C)(C)C FZQMZRXKWHQJAG-VOTSOKGWSA-N 0.000 description 1
- RJTHVQJBBSFMAH-SNAWJCMRSA-N (e)-4-phenylbut-2-enenitrile Chemical compound N#C\C=C\CC1=CC=CC=C1 RJTHVQJBBSFMAH-SNAWJCMRSA-N 0.000 description 1
- ILRJSGCEAPKUQT-HJWRWDBZSA-N (z)-dec-2-enenitrile Chemical compound CCCCCCC\C=C/C#N ILRJSGCEAPKUQT-HJWRWDBZSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
- GTUOTYSUNDPMPS-UHFFFAOYSA-N 1-prop-2-enylcyclohexene Chemical compound C=CCC1=CCCCC1 GTUOTYSUNDPMPS-UHFFFAOYSA-N 0.000 description 1
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 1
- OIWUZXBBESWTHG-UHFFFAOYSA-N 2,4,6-trimethylhept-3-enedinitrile Chemical compound N#CC(C)CC(C)=CC(C)C#N OIWUZXBBESWTHG-UHFFFAOYSA-N 0.000 description 1
- YVLNGQFWHIEHIK-UHFFFAOYSA-N 2,4-dimethyloct-3-enedinitrile Chemical compound N#CC(C)C=C(C)CCCC#N YVLNGQFWHIEHIK-UHFFFAOYSA-N 0.000 description 1
- PZNDEYCHUBUQOA-UHFFFAOYSA-N 2,4-dimethyloct-4-enedinitrile Chemical compound N#CC(C)CC(C)=CCCC#N PZNDEYCHUBUQOA-UHFFFAOYSA-N 0.000 description 1
- DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical group CC(=C)CCC(C)=C DSAYAFZWRDYBQY-UHFFFAOYSA-N 0.000 description 1
- JFGVTUJBHHZRAB-UHFFFAOYSA-N 2,6-Di-tert-butyl-1,4-benzenediol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1O JFGVTUJBHHZRAB-UHFFFAOYSA-N 0.000 description 1
- MNZHYRRSAWBQBC-UHFFFAOYSA-N 2-(3-phenylprop-2-enyl)hexanenitrile Chemical compound CCCCC(C#N)CC=CC1=CC=CC=C1 MNZHYRRSAWBQBC-UHFFFAOYSA-N 0.000 description 1
- QMXFDIOJRYFMRN-UHFFFAOYSA-N 2-(4-methylphenyl)prop-2-enenitrile Chemical compound CC1=CC=C(C(=C)C#N)C=C1 QMXFDIOJRYFMRN-UHFFFAOYSA-N 0.000 description 1
- HVEYZMRCFHKSOG-UHFFFAOYSA-N 2-ethyl-4-methylpent-4-enenitrile Chemical compound CCC(C#N)CC(C)=C HVEYZMRCFHKSOG-UHFFFAOYSA-N 0.000 description 1
- TYHFRIJIMIEVMH-UHFFFAOYSA-N 2-methyl-4-methylideneoctanedinitrile Chemical compound N#CC(C)CC(=C)CCCC#N TYHFRIJIMIEVMH-UHFFFAOYSA-N 0.000 description 1
- SDSLOASSKRFQHW-UHFFFAOYSA-N 2-methylpent-4-enenitrile Chemical compound N#CC(C)CC=C SDSLOASSKRFQHW-UHFFFAOYSA-N 0.000 description 1
- MXTNFIYGTWARIN-UHFFFAOYSA-N 2-methylprop-2-enylbenzene Chemical compound CC(=C)CC1=CC=CC=C1 MXTNFIYGTWARIN-UHFFFAOYSA-N 0.000 description 1
- IGPZPJUWSPSBSN-UHFFFAOYSA-N 2-prop-2-enylhexanenitrile Chemical compound CCCCC(C#N)CC=C IGPZPJUWSPSBSN-UHFFFAOYSA-N 0.000 description 1
- DNSJZPQOFGSRMK-UHFFFAOYSA-N 2-propylhex-5-enenitrile Chemical compound CCCC(C#N)CCC=C DNSJZPQOFGSRMK-UHFFFAOYSA-N 0.000 description 1
- WOYJULKCSUHDAS-UHFFFAOYSA-N 3,5-dimethylhex-5-enenitrile Chemical compound N#CCC(C)CC(C)=C WOYJULKCSUHDAS-UHFFFAOYSA-N 0.000 description 1
- RGURBRHZWFDJBM-UHFFFAOYSA-N 3-Allylcyclohexene Chemical compound C=CCC1CCCC=C1 RGURBRHZWFDJBM-UHFFFAOYSA-N 0.000 description 1
- VEBCSALPNMISTC-UHFFFAOYSA-N 3-cyclohexylprop-2-enenitrile Chemical compound N#CC=CC1CCCCC1 VEBCSALPNMISTC-UHFFFAOYSA-N 0.000 description 1
- JTTMYKSFKOOQLP-UHFFFAOYSA-N 4-hydroxydiphenylamine Chemical compound C1=CC(O)=CC=C1NC1=CC=CC=C1 JTTMYKSFKOOQLP-UHFFFAOYSA-N 0.000 description 1
- MHGQCSFMAYEPPE-UHFFFAOYSA-N 4-methylhept-2-enenitrile Chemical compound CCCC(C)C=CC#N MHGQCSFMAYEPPE-UHFFFAOYSA-N 0.000 description 1
- YCZXQOAWIFXSAK-UHFFFAOYSA-N 4-tert-butyl-5-methylhex-5-enenitrile Chemical compound CC(=C)C(C(C)(C)C)CCC#N YCZXQOAWIFXSAK-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- NUBPLSKFJSAWFF-UHFFFAOYSA-N 5,7,7-trimethyloct-5-enenitrile Chemical compound CC(C)(C)C=C(C)CCCC#N NUBPLSKFJSAWFF-UHFFFAOYSA-N 0.000 description 1
- IRLJIXQXUAWVQS-UHFFFAOYSA-N 5-(4-methylphenyl)non-2-enenitrile Chemical compound N#CC=CCC(CCCC)C1=CC=C(C)C=C1 IRLJIXQXUAWVQS-UHFFFAOYSA-N 0.000 description 1
- QEQVVLMSLWIQRV-UHFFFAOYSA-N 5-methylhex-2-enenitrile Chemical compound CC(C)CC=CC#N QEQVVLMSLWIQRV-UHFFFAOYSA-N 0.000 description 1
- WOKRQPAGFRZCQI-UHFFFAOYSA-N 5-methylidenenon-2-enedinitrile Chemical compound N#CCCCC(=C)CC=CC#N WOKRQPAGFRZCQI-UHFFFAOYSA-N 0.000 description 1
- GKDHCZVJRWHPED-UHFFFAOYSA-N 6,6,8,8-tetramethylnon-2-enenitrile Chemical compound CC(C)(C)CC(C)(C)CCC=CC#N GKDHCZVJRWHPED-UHFFFAOYSA-N 0.000 description 1
- JQYHFFQMWMIWGC-UHFFFAOYSA-N 6,7,8-trimethyl-9-phenylnon-2-enenitrile Chemical compound N#CC=CCCC(C)C(C)C(C)CC1=CC=CC=C1 JQYHFFQMWMIWGC-UHFFFAOYSA-N 0.000 description 1
- DPHKZAJNBVBKHP-UHFFFAOYSA-N 6-cyclohexyloct-2-enenitrile Chemical compound N#CC=CCCC(CC)C1CCCCC1 DPHKZAJNBVBKHP-UHFFFAOYSA-N 0.000 description 1
- AEACDLQIFVKSPM-UHFFFAOYSA-N 6-phenyldec-2-enenitrile Chemical compound N#CC=CCCC(CCCC)C1=CC=CC=C1 AEACDLQIFVKSPM-UHFFFAOYSA-N 0.000 description 1
- AEYGMBDHSNNGDY-UHFFFAOYSA-N 7,7-dimethyl-5-methylideneoctanenitrile Chemical compound CC(C)(C)CC(=C)CCCC#N AEYGMBDHSNNGDY-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- QROGIFZRVHSFLM-QHHAFSJGSA-N [(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=CC=C1 QROGIFZRVHSFLM-QHHAFSJGSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229910000074 antimony hydride Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
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- SEBDYZTUVULEBJ-UHFFFAOYSA-N diphenylarsenic Chemical compound C=1C=CC=CC=1[As]C1=CC=CC=C1 SEBDYZTUVULEBJ-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- CSAZMTWHVNCILA-UHFFFAOYSA-N hex-2-enenitrile Chemical compound CCCC=CC#N CSAZMTWHVNCILA-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 description 1
- UDLKTTGEFCQAKB-UHFFFAOYSA-N tris(2-cyclohexylphenyl)phosphane Chemical compound C1CCCCC1C1=CC=CC=C1P(C=1C(=CC=CC=1)C1CCCCC1)C1=CC=CC=C1C1CCCCC1 UDLKTTGEFCQAKB-UHFFFAOYSA-N 0.000 description 1
- IAZVKSPSDDMXJN-UHFFFAOYSA-N tris(2-hexylphenyl)phosphane Chemical compound CCCCCCC1=CC=CC=C1P(C=1C(=CC=CC=1)CCCCCC)C1=CC=CC=C1CCCCCC IAZVKSPSDDMXJN-UHFFFAOYSA-N 0.000 description 1
- HLHSWHSBJYSPNQ-UHFFFAOYSA-N tris(3,5-dimethylphenyl)bismuthane Chemical compound CC1=CC(C)=CC([Bi](C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 HLHSWHSBJYSPNQ-UHFFFAOYSA-N 0.000 description 1
- RYXYUARTMQUYKV-UHFFFAOYSA-N tris(4-butylphenyl)phosphane Chemical compound C1=CC(CCCC)=CC=C1P(C=1C=CC(CCCC)=CC=1)C1=CC=C(CCCC)C=C1 RYXYUARTMQUYKV-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/599,735 US3985786A (en) | 1975-07-28 | 1975-07-28 | Preparation of unsaturated nitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2633364A1 true DE2633364A1 (de) | 1977-02-17 |
Family
ID=24400855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762633364 Pending DE2633364A1 (de) | 1975-07-28 | 1976-07-24 | Verfahren zum herstellen von ungesaettigten dinitrilen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3985786A (enExample) |
| JP (1) | JPS5225721A (enExample) |
| BE (1) | BE844575A (enExample) |
| CA (1) | CA1055049A (enExample) |
| DE (1) | DE2633364A1 (enExample) |
| FR (1) | FR2319626A1 (enExample) |
| GB (1) | GB1538136A (enExample) |
| IT (1) | IT1062549B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4217299A (en) * | 1973-11-28 | 1980-08-12 | Japan Synthetic Rubber Co., Ltd. | Method for converting unsaturated compound having functional group |
| JPS5156211A (ja) * | 1974-11-12 | 1976-05-17 | Fujitsu Ltd | Jikikirokuhoshiki |
| US4117001A (en) * | 1977-07-05 | 1978-09-26 | Phillips Petroleum Company | Pyrolysis of heavies formed in production of unsaturated dinitriles |
| US4117002A (en) * | 1977-07-05 | 1978-09-26 | Phillips Petroleum Company | Pyrolysis of heavies formed in production of unsaturated dinitriles |
| US4136077A (en) * | 1977-12-16 | 1979-01-23 | Phillips Petroleum Company | Reaction product of olefinically-unsaturated nitrile and a monoolefinic hydrocarbon as plasticizer for conjugated diene-unsaturated nitrile rubber |
| US4200586A (en) * | 1978-01-10 | 1980-04-29 | Phillips Petroleum Company | Inhibiting the carbon-carbon double bond isomerization of substituted or unsubstituted hydrocarbon compounds |
| US4195155A (en) * | 1978-05-02 | 1980-03-25 | Phillips Petroleum Company | Hydrogenated polynitrile mixture and use as epoxy hardener |
| US4275237A (en) * | 1978-05-02 | 1981-06-23 | Philips Petroleum Company | Hydrogenated polynitrile mixture useful as an epoxy hardener |
| US4279621A (en) * | 1978-09-14 | 1981-07-21 | Phillips Petroleum Company | Polyamines mixture for stabilizing certain hydrocarbons against oxidation |
| US4217303A (en) * | 1979-04-24 | 1980-08-12 | Phillips Petroleum Company | Preparation of unsaturated nitriles |
| US4255352A (en) * | 1979-04-24 | 1981-03-10 | Phillips Petroleum Company | Preparation of unsaturated nitriles |
| US4218394A (en) * | 1979-04-24 | 1980-08-19 | Phillips Petroleum Company | Preparation of unsaturated nitriles |
| US4472319A (en) * | 1980-07-01 | 1984-09-18 | Phillips Petroleum Company | Preparation of unsaturated nitriles using a surfactant |
| JPS581802A (ja) * | 1981-06-27 | 1983-01-07 | Victor Co Of Japan Ltd | 磁気記録再生方式及び磁気ヘツド |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2280058A (en) * | 1942-04-21 | Cyanoethylation of carbocycijc | ||
| US2394962A (en) * | 1943-03-02 | 1946-02-12 | Resinous Prod & Chemical Co | Cyanoethylated products and preparation thereof |
| US2460536A (en) * | 1946-07-18 | 1949-02-01 | Du Pont | Reaction between vinyl cyanide and reactive methylene compounds |
| US2641607A (en) * | 1950-06-15 | 1953-06-09 | Du Pont | Method for preparing unsaturated nitriles |
| US3539615A (en) * | 1968-09-27 | 1970-11-10 | Du Pont | Preparation of cyanocyclobutane by the cycloaddition of ethylene and acrylonitrile |
| US3840583A (en) * | 1972-05-03 | 1974-10-08 | Phillips Petroleum Co | Method of preparing unsaturated dinitriles |
-
1975
- 1975-07-28 US US05/599,735 patent/US3985786A/en not_active Expired - Lifetime
-
1976
- 1976-06-08 CA CA254,355A patent/CA1055049A/en not_active Expired
- 1976-07-22 JP JP51087713A patent/JPS5225721A/ja active Pending
- 1976-07-24 DE DE19762633364 patent/DE2633364A1/de active Pending
- 1976-07-27 IT IT25765/76A patent/IT1062549B/it active
- 1976-07-27 GB GB31258/76A patent/GB1538136A/en not_active Expired
- 1976-07-28 BE BE169287A patent/BE844575A/xx unknown
- 1976-07-28 FR FR7623068A patent/FR2319626A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1055049A (en) | 1979-05-22 |
| GB1538136A (en) | 1979-01-10 |
| JPS5225721A (en) | 1977-02-25 |
| FR2319626A1 (fr) | 1977-02-25 |
| BE844575A (fr) | 1977-01-28 |
| IT1062549B (it) | 1984-10-20 |
| US3985786A (en) | 1976-10-12 |
| FR2319626B1 (enExample) | 1978-05-05 |
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| OHN | Withdrawal |