DE3131047C2 - - Google Patents
Info
- Publication number
- DE3131047C2 DE3131047C2 DE3131047A DE3131047A DE3131047C2 DE 3131047 C2 DE3131047 C2 DE 3131047C2 DE 3131047 A DE3131047 A DE 3131047A DE 3131047 A DE3131047 A DE 3131047A DE 3131047 C2 DE3131047 C2 DE 3131047C2
- Authority
- DE
- Germany
- Prior art keywords
- isomerization
- reaction
- nickel
- phosphite
- catalyst
- 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.)
- Expired - Lifetime
Links
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 25
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000006317 isomerization reaction Methods 0.000 claims description 21
- 229910052759 nickel Inorganic materials 0.000 claims description 19
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 claims 1
- 239000003446 ligand Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 10
- -1 3-pentenenitrile Chemical compound 0.000 description 8
- IHXNSHZBFXGOJM-HWKANZROSA-N (e)-2-methylbut-2-enenitrile Chemical compound C\C=C(/C)C#N IHXNSHZBFXGOJM-HWKANZROSA-N 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 150000002816 nickel compounds Chemical class 0.000 description 4
- 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 4
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 3
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002815 nickel Chemical class 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- QXKPLZDCTKREIA-UHFFFAOYSA-N diphenoxy(phenyl)phosphane Chemical compound C=1C=CC=CC=1OP(C=1C=CC=CC=1)OC1=CC=CC=C1 QXKPLZDCTKREIA-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 1
- UPDNYUVJHQABBS-UHFFFAOYSA-N phenoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1OP(C=1C=CC=CC=1)C1=CC=CC=C1 UPDNYUVJHQABBS-UHFFFAOYSA-N 0.000 description 1
- 125000005538 phosphinite group Chemical group 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- HABWCPIKWOZMSN-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphite Chemical compound CC1=CC(C)=CC=C1OP(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C HABWCPIKWOZMSN-UHFFFAOYSA-N 0.000 description 1
- AYGODXBPXMHVBL-UHFFFAOYSA-N tris(2,5-dimethylphenyl) phosphite Chemical compound CC1=CC=C(C)C(OP(OC=2C(=CC=C(C)C=2)C)OC=2C(=CC=C(C)C=2)C)=C1 AYGODXBPXMHVBL-UHFFFAOYSA-N 0.000 description 1
- BKHZQJRTFNFCTG-UHFFFAOYSA-N tris(2-methylphenyl) phosphite Chemical compound CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C BKHZQJRTFNFCTG-UHFFFAOYSA-N 0.000 description 1
- DAZUWKNHFLGZSN-UHFFFAOYSA-N tris(2-phenylphenyl) phosphite Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1OP(OC=1C(=CC=CC=1)C=1C=CC=CC=1)OC1=CC=CC=C1C1=CC=CC=C1 DAZUWKNHFLGZSN-UHFFFAOYSA-N 0.000 description 1
- AZLGDNBTDKZORI-UHFFFAOYSA-N tris(3-methylphenyl) phosphite Chemical compound CC1=CC=CC(OP(OC=2C=C(C)C=CC=2)OC=2C=C(C)C=CC=2)=C1 AZLGDNBTDKZORI-UHFFFAOYSA-N 0.000 description 1
- AMGMFFUMIJRDGW-UHFFFAOYSA-N tris(4-chlorophenyl) phosphite Chemical compound C1=CC(Cl)=CC=C1OP(OC=1C=CC(Cl)=CC=1)OC1=CC=C(Cl)C=C1 AMGMFFUMIJRDGW-UHFFFAOYSA-N 0.000 description 1
- VDAQOERDAAOXQV-UHFFFAOYSA-N tris(4-methoxyphenyl) phosphite Chemical compound C1=CC(OC)=CC=C1OP(OC=1C=CC(OC)=CC=1)OC1=CC=C(OC)C=C1 VDAQOERDAAOXQV-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000010457 zeolite Substances 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 |
|---|---|---|---|
| US06/175,398 US4298546A (en) | 1980-08-05 | 1980-08-05 | Isomerization of 2-methyl-3-butenenitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3131047A1 DE3131047A1 (de) | 1982-03-18 |
| DE3131047C2 true DE3131047C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-07-26 |
Family
ID=22640086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813131047 Granted DE3131047A1 (de) | 1980-08-05 | 1981-08-05 | Verfahren zur isomerisierung von 2-methyl-3-butennitril |
Country Status (9)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2710909B1 (fr) * | 1993-10-08 | 1995-12-15 | Rhone Poulenc Chimie | Procédé d'isomérisation du méthyl-2 butène-3 nitrile. |
| CN1082946C (zh) * | 1993-11-23 | 2002-04-17 | 纳幕尔杜邦公司 | 用于单烯烃氢氰化的方法和催化剂组合物 |
| BR9507460A (pt) | 1994-04-14 | 1997-09-02 | Du Pont | Processo para hidrocianação e composição de precursor de catalisador |
| TW315370B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1994-10-07 | 1997-09-11 | Du Pont | |
| US5512696A (en) * | 1995-07-21 | 1996-04-30 | E. I. Du Pont De Nemours And Company | Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor |
| US5440067A (en) * | 1994-11-18 | 1995-08-08 | E. I. Dupont De Nemours And Company | Catalyzed gas phase isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles |
| IN187044B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1995-01-27 | 2002-01-05 | Du Pont | |
| US5821378A (en) * | 1995-01-27 | 1998-10-13 | E. I. Du Pont De Nemours And Company | Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles |
| MY133839A (en) * | 2000-03-14 | 2007-11-30 | Shell Int Research | Process for the carbonylation of pentenenitrile |
| US6706912B2 (en) | 2000-03-14 | 2004-03-16 | Shell Oil Company | Process for the carbonylation of ethylenically unsaturated compounds |
| US6726127B2 (en) † | 2001-11-14 | 2004-04-27 | Spraying Systems Co. | Air assisted liquid spray nozzle assembly |
| FR2850966B1 (fr) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| DE10311119A1 (de) * | 2003-03-12 | 2004-09-23 | Basf Ag | Verfahren zur Isomerisierung von 2-Methyl-3-butennitril zu linearem Pentennitril |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| FR2854892B1 (fr) | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| CA2644961A1 (en) | 2006-03-17 | 2007-09-27 | Invista Technologies S.A.R.L. | Method for the purification of triorganophosphites by treatment with a basic additive |
| US7709673B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7709674B2 (en) | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
| US7880028B2 (en) | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536748A (en) * | 1965-11-23 | 1970-10-27 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles |
| US3853948A (en) * | 1965-11-23 | 1974-12-10 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to linear pentene-nitriles |
| US3542847A (en) * | 1969-09-15 | 1970-11-24 | Du Pont | Process for isomerizing 3-pentenenitrile to 4-pentenenitrile |
| US3676481A (en) * | 1970-06-29 | 1972-07-11 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles in the presence of certain metal salt and/or tri(hydrocarbyl)boron promoters |
| US3852328A (en) * | 1973-09-26 | 1974-12-03 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to a linear pentenenitrile |
| US3852329A (en) * | 1973-10-02 | 1974-12-03 | Du Pont | Process for isomerization of 2-methyl-3-butene-nitrile to a linear pentenenitrile |
-
1980
- 1980-08-05 US US06/175,398 patent/US4298546A/en not_active Expired - Lifetime
-
1981
- 1981-08-04 JP JP56121496A patent/JPH0139417B2/ja not_active Expired
- 1981-08-04 NL NL8103666A patent/NL8103666A/nl not_active Application Discontinuation
- 1981-08-04 CA CA000383166A patent/CA1166268A/en not_active Expired
- 1981-08-04 FR FR8115114A patent/FR2488254A1/fr active Granted
- 1981-08-04 BE BE0/205570A patent/BE889845A/fr not_active IP Right Cessation
- 1981-08-04 GB GB8123760A patent/GB2081268B/en not_active Expired
- 1981-08-04 IT IT23364/81A patent/IT1138138B/it active
- 1981-08-05 DE DE19813131047 patent/DE3131047A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2488254A1 (fr) | 1982-02-12 |
| NL8103666A (nl) | 1982-03-01 |
| FR2488254B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-01-06 |
| US4298546A (en) | 1981-11-03 |
| IT1138138B (it) | 1986-09-17 |
| JPS5754155A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-03-31 |
| JPH0139417B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-08-21 |
| GB2081268A (en) | 1982-02-17 |
| IT8123364A0 (it) | 1981-08-04 |
| DE3131047A1 (de) | 1982-03-18 |
| CA1166268A (en) | 1984-04-24 |
| GB2081268B (en) | 1984-03-07 |
| BE889845A (fr) | 1982-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |