DE2655715C2 - Verfahren zur Herstellung von Vinylmilchsäurenitril - Google Patents
Verfahren zur Herstellung von VinylmilchsäurenitrilInfo
- Publication number
- DE2655715C2 DE2655715C2 DE2655715A DE2655715A DE2655715C2 DE 2655715 C2 DE2655715 C2 DE 2655715C2 DE 2655715 A DE2655715 A DE 2655715A DE 2655715 A DE2655715 A DE 2655715A DE 2655715 C2 DE2655715 C2 DE 2655715C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- solvent
- methyl vinyl
- vinyl ketone
- yield
- 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
Links
- 238000000034 method Methods 0.000 title claims description 20
- -1 vinyl lactic acid nitrile Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 49
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 16
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- CWVZGJORVTZXFW-UHFFFAOYSA-N [benzyl(dimethyl)silyl]methyl carbamate Chemical compound NC(=O)OC[Si](C)(C)CC1=CC=CC=C1 CWVZGJORVTZXFW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- JFVBCXHSPKJLRP-UHFFFAOYSA-N 4-oxopentanenitrile Chemical compound CC(=O)CCC#N JFVBCXHSPKJLRP-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000458557 Liposcelis corrodens Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- HWXBTNAVRSUOJR-UHFFFAOYSA-N alpha-hydroxyglutaric acid Natural products OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver nitrate Substances [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000006561 solvent free reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2655715A DE2655715C2 (de) | 1976-12-09 | 1976-12-09 | Verfahren zur Herstellung von Vinylmilchsäurenitril |
| NL7712965A NL7712965A (nl) | 1976-12-09 | 1977-11-24 | Werkwijze voor het bereiden van vinylmelkzuur- nitrile. |
| CA000291831A CA1119191A (en) | 1976-12-09 | 1977-11-28 | Manufacture of vinyl-lactonitrile |
| US05/855,877 US4218393A (en) | 1976-12-09 | 1977-11-30 | Manufacture of vinyl-lactonitrile |
| JP14409077A JPS5373518A (en) | 1976-12-09 | 1977-12-02 | Process for preparing vinyllcatonate nitrile |
| FR7736501A FR2373518A1 (fr) | 1976-12-09 | 1977-12-05 | Procede de preparation du nitrile vinyllactique |
| BE183241A BE861591A (fr) | 1976-12-09 | 1977-12-07 | Procede de preparation du nitrile vinyllactique |
| GB51101/77A GB1590994A (en) | 1976-12-09 | 1977-12-08 | Manufacture of vinyl-lactonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2655715A DE2655715C2 (de) | 1976-12-09 | 1976-12-09 | Verfahren zur Herstellung von Vinylmilchsäurenitril |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2655715A1 DE2655715A1 (de) | 1978-06-15 |
| DE2655715C2 true DE2655715C2 (de) | 1985-10-10 |
Family
ID=5995034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2655715A Expired DE2655715C2 (de) | 1976-12-09 | 1976-12-09 | Verfahren zur Herstellung von Vinylmilchsäurenitril |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4218393A (OSRAM) |
| JP (1) | JPS5373518A (OSRAM) |
| BE (1) | BE861591A (OSRAM) |
| CA (1) | CA1119191A (OSRAM) |
| DE (1) | DE2655715C2 (OSRAM) |
| FR (1) | FR2373518A1 (OSRAM) |
| GB (1) | GB1590994A (OSRAM) |
| NL (1) | NL7712965A (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4611076A (en) * | 1985-06-26 | 1986-09-09 | Shell Oil Company | Chiral cyanohydrination process |
| EP3392237B1 (de) * | 2017-04-21 | 2019-10-02 | Evonik Degussa GmbH | Verfahren zur herstellung von acroleincyanhydrinen |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2166600A (en) * | 1939-07-18 | Oxygen containing nitriles of the | ||
| DE694942C (de) | 1935-03-28 | 1940-08-12 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Cyanhydrinen |
| GB482300A (en) * | 1935-09-28 | 1938-03-28 | Ig Farbenindustrie Ag | Manufacture of nitriles of the c-series containing oxygen |
| DE691621C (de) * | 1935-09-29 | 1940-06-01 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Nitrilen mit 5 Kohlenstoffatomen |
| US2188340A (en) * | 1936-03-18 | 1940-01-30 | Du Pont | Process of reacting methyl vinyl ketone with hydrogen cyanide and products thereby obtained |
| US2537814A (en) * | 1946-06-14 | 1951-01-09 | American Cyanamid Co | Preparation of acetone cyanohydrin |
| US2815385A (en) * | 1955-01-06 | 1957-12-03 | Union Carbide Corp | Process for the production of 2-chloroacrolein and derivatives thereof |
| DE1087122B (de) * | 1958-12-05 | 1960-08-18 | Knapsack Ag | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Cyanhydrinen |
| GB892781A (en) * | 1959-12-29 | 1962-03-28 | Knapsack Ag | Process and apparatus for the continuous production of cyanohydrins |
| GB958896A (en) * | 1960-04-23 | 1964-05-27 | Knapsack Ag | Process and apparatus for the continuous production of cyanohydrins |
| GB1055060A (en) * | 1963-09-23 | 1967-01-11 | Asahi Kasei Dogyo Kabushiki Ka | Process for producing alpha hydroxy-glutaronitrile and its alkyl-substitute derivatives |
| JPS5021450B2 (OSRAM) * | 1972-05-15 | 1975-07-23 |
-
1976
- 1976-12-09 DE DE2655715A patent/DE2655715C2/de not_active Expired
-
1977
- 1977-11-24 NL NL7712965A patent/NL7712965A/xx not_active Application Discontinuation
- 1977-11-28 CA CA000291831A patent/CA1119191A/en not_active Expired
- 1977-11-30 US US05/855,877 patent/US4218393A/en not_active Expired - Lifetime
- 1977-12-02 JP JP14409077A patent/JPS5373518A/ja active Pending
- 1977-12-05 FR FR7736501A patent/FR2373518A1/fr active Granted
- 1977-12-07 BE BE183241A patent/BE861591A/xx not_active IP Right Cessation
- 1977-12-08 GB GB51101/77A patent/GB1590994A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE861591A (fr) | 1978-06-07 |
| JPS5373518A (en) | 1978-06-30 |
| GB1590994A (en) | 1981-06-10 |
| FR2373518A1 (fr) | 1978-07-07 |
| DE2655715A1 (de) | 1978-06-15 |
| US4218393A (en) | 1980-08-19 |
| FR2373518B1 (OSRAM) | 1983-09-23 |
| NL7712965A (nl) | 1978-06-13 |
| CA1119191A (en) | 1982-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |