JPH0361658B2 - - Google Patents
Info
- Publication number
- JPH0361658B2 JPH0361658B2 JP59091191A JP9119184A JPH0361658B2 JP H0361658 B2 JPH0361658 B2 JP H0361658B2 JP 59091191 A JP59091191 A JP 59091191A JP 9119184 A JP9119184 A JP 9119184A JP H0361658 B2 JPH0361658 B2 JP H0361658B2
- Authority
- JP
- Japan
- Prior art keywords
- ester
- pentenoic
- pentenoic acid
- acidic
- 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
- -1 pentenoic acid ester Chemical class 0.000 claims description 25
- 230000002378 acidificating effect Effects 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims description 10
- 239000010457 zeolite Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910021536 Zeolite Inorganic materials 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 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
- 229910000510 noble metal Inorganic materials 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 239000010948 rhodium Substances 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000006317 isomerization reaction Methods 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 4
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- MBAHGFJTIVZLFB-SNAWJCMRSA-N methyl (e)-pent-2-enoate Chemical compound CC\C=C\C(=O)OC MBAHGFJTIVZLFB-SNAWJCMRSA-N 0.000 description 3
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical class OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical class C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 3
- PNPPVRALIYXJBW-UHFFFAOYSA-N 6-oxohexanoic acid Chemical class OC(=O)CCCCC=O PNPPVRALIYXJBW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SHCSFZHSNSGTOP-UHFFFAOYSA-N Methyl 4-pentenoate Chemical compound COC(=O)CCC=C SHCSFZHSNSGTOP-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- OBCIYFQTMFZLEJ-HWKANZROSA-N butyl (e)-pent-3-enoate Chemical compound CCCCOC(=O)C\C=C\C OBCIYFQTMFZLEJ-HWKANZROSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- AGMKVZDPATUSMS-AATRIKPKSA-N ethyl (e)-pent-2-enoate Chemical compound CCOC(=O)\C=C\CC AGMKVZDPATUSMS-AATRIKPKSA-N 0.000 description 1
- UMLQAWUDAFCGGS-HWKANZROSA-N ethyl (e)-pent-3-enoate Chemical compound CCOC(=O)C\C=C\C UMLQAWUDAFCGGS-HWKANZROSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- KJALUUCEMMPKAC-ONEGZZNKSA-N methyl (e)-pent-3-enoate Chemical compound COC(=O)C\C=C\C KJALUUCEMMPKAC-ONEGZZNKSA-N 0.000 description 1
- MBAHGFJTIVZLFB-PLNGDYQASA-N methyl (z)-pent-2-enoate Chemical compound CC\C=C/C(=O)OC MBAHGFJTIVZLFB-PLNGDYQASA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- QXSSGYRBUZRDNL-HWKANZROSA-N propyl (e)-pent-3-enoate Chemical compound CCCOC(=O)C\C=C\C QXSSGYRBUZRDNL-HWKANZROSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
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)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833317163 DE3317163A1 (de) | 1983-05-11 | 1983-05-11 | Verfahren zur herstellung von 4-pentensaeureestern |
| DE3317163.7 | 1983-05-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59212446A JPS59212446A (ja) | 1984-12-01 |
| JPH0361658B2 true JPH0361658B2 (en:Method) | 1991-09-20 |
Family
ID=6198708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59091191A Granted JPS59212446A (ja) | 1983-05-11 | 1984-05-09 | ４−ペンテン酸エステルの製法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4529815A (en:Method) |
| EP (1) | EP0126349B1 (en:Method) |
| JP (1) | JPS59212446A (en:Method) |
| DE (2) | DE3317163A1 (en:Method) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3412295A1 (de) * | 1984-04-03 | 1985-10-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur abtrennung von 4- pentensaeuremethylester aus solchen und 3- pentensaeuremethylester enthaltenden gemischen |
| DE3413448A1 (de) * | 1984-04-10 | 1985-10-17 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von pentensaeure c(pfeil abwaerts)1(pfeil abwaerts)- bis c(pfeil abwaerts)4(pfeil abwaerts)- alkylestern |
| DE3521380A1 (de) * | 1985-06-14 | 1986-12-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 4-pentensaeureestern |
| DE3521381A1 (de) * | 1985-06-14 | 1986-12-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 4-pentensaeureestern |
| DE3609139A1 (de) * | 1986-03-19 | 1987-09-24 | Basf Ag | Verfahren zur herstellung von 4-pentensaeureestern |
| DE3638011A1 (de) * | 1986-11-07 | 1988-05-11 | Basf Ag | Verfahren zur herstellung von 4-pentensaeureestern |
| DE3640596A1 (de) * | 1986-11-27 | 1988-06-01 | Basf Ag | Verfahren zur herstellung von 3-pentensaeureestern aus 2-pentensaeureestern |
| DE3640598A1 (de) * | 1986-11-27 | 1988-06-01 | Basf Ag | Verfahren zur isomerisierung von 2-cis-pentensaeureestern zu 2-trans-pentensaeureestern |
| DE3640597A1 (de) * | 1986-11-27 | 1988-06-01 | Basf Ag | Verfahren zur isomerisierung von 2-pentensaeureestern zu 3-pentensaeureestern |
| US5001257A (en) * | 1987-05-11 | 1991-03-19 | E. I. Du Pont De Nemours And Company | Preparation of 4-pentenoic acid, amide or esters by isomerization |
| US4783546A (en) * | 1987-06-02 | 1988-11-08 | E. I. Du Pont De Nemours And Company | Preparation of 4-pentenenitrile by isomerization |
| US4943397A (en) * | 1988-09-22 | 1990-07-24 | Shell Oil Company | Metathesis of functional olefins |
| TW272979B (en:Method) * | 1992-10-02 | 1996-03-21 | Rhone Poulenc Chimic | |
| FR2696450B1 (fr) * | 1992-10-02 | 1994-12-02 | Rhone Poulenc Chimie | Procédé d'isomérisation de l'acide pentène-2-oïque en acides pentène-3-oïque et pentène-4-oïque par catalyse acide. |
| TW524801B (en) * | 1999-03-22 | 2003-03-21 | Shell Int Research | Process for the carbonylation of conjugated dienes |
| WO2014163506A1 (en) | 2013-04-05 | 2014-10-09 | Universiteit Leiden | Process to prepare epsilon-caprolactam |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3013066A (en) * | 1961-03-23 | 1961-12-12 | Du Pont | Dimerization of alpha olefins with a group viii noble metal salt |
| US3161672A (en) * | 1961-11-06 | 1964-12-15 | Exxon Research Engineering Co | Production of unsaturated monoesters by the rhodium catalyzed carbonylation of conjugated diolefins |
| US3403108A (en) * | 1964-06-24 | 1968-09-24 | Pullman Inc | Aluminosilicate catalyst containing a group viii metal compound and a metal halide |
| US3450730A (en) * | 1967-07-14 | 1969-06-17 | Nat Distillers Chem Corp | Novel organometallic complexes |
| US3966799A (en) * | 1974-07-22 | 1976-06-29 | International Flavors & Fragrances Inc. | Alkyl esters of 2-methyl-4-pentenoic acid |
| JPS5842860B2 (ja) * | 1979-10-12 | 1983-09-22 | 三菱瓦斯化学株式会社 | ２−ペンテン酸エステルの製造方法 |
| US4332966A (en) * | 1979-12-17 | 1982-06-01 | Mitsubishi Gas Chemical Company, Inc. | Process for producing 3-pentenoic esters |
-
1983
- 1983-05-11 DE DE19833317163 patent/DE3317163A1/de not_active Withdrawn
-
1984
- 1984-05-03 EP EP84104989A patent/EP0126349B1/de not_active Expired
- 1984-05-03 DE DE8484104989T patent/DE3460504D1/de not_active Expired
- 1984-05-09 US US06/608,459 patent/US4529815A/en not_active Expired - Lifetime
- 1984-05-09 JP JP59091191A patent/JPS59212446A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3460504D1 (en) | 1986-09-25 |
| DE3317163A1 (de) | 1984-11-15 |
| EP0126349B1 (de) | 1986-08-20 |
| JPS59212446A (ja) | 1984-12-01 |
| US4529815A (en) | 1985-07-16 |
| EP0126349A1 (de) | 1984-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |