DE2639327C2 - Verfahren zur Herstellung von α-substituierten Cyancarbonsäurealkylestern - Google Patents
Verfahren zur Herstellung von α-substituierten CyancarbonsäurealkylesternInfo
- Publication number
- DE2639327C2 DE2639327C2 DE2639327A DE2639327A DE2639327C2 DE 2639327 C2 DE2639327 C2 DE 2639327C2 DE 2639327 A DE2639327 A DE 2639327A DE 2639327 A DE2639327 A DE 2639327A DE 2639327 C2 DE2639327 C2 DE 2639327C2
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- substituted
- acid
- methyl
- pyridine
- 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
- 238000002360 preparation method Methods 0.000 title claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 150000002825 nitriles Chemical class 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- -1 nitriles compounds Chemical class 0.000 claims description 12
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 125000004494 ethyl ester group Chemical group 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000003222 pyridines Chemical class 0.000 description 12
- YXFVFGQBKHJCRO-UHFFFAOYSA-N 2,4-dicyano-2-methylbutanoic acid Chemical compound C(#N)C(C(=O)O)(CCC#N)C YXFVFGQBKHJCRO-UHFFFAOYSA-N 0.000 description 11
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 10
- MIHRVXYXORIINI-UHFFFAOYSA-N ethyl 2-cyanopropionate Chemical compound CCOC(=O)C(C)C#N MIHRVXYXORIINI-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 8
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 6
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 2
- JDEFPFLTCXIVDH-UHFFFAOYSA-N 2-cyanopropanoic acid Chemical class N#CC(C)C(O)=O JDEFPFLTCXIVDH-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- ACRWYXSKEHUQDB-UHFFFAOYSA-N 3-phenylpropionitrile Chemical compound N#CCCC1=CC=CC=C1 ACRWYXSKEHUQDB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- GWHHQWUYMDWMAY-UHFFFAOYSA-N methyl 2-cyanopropanoate Chemical compound COC(=O)C(C)C#N GWHHQWUYMDWMAY-UHFFFAOYSA-N 0.000 description 2
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- PVWGZXZMYBHKKP-UHFFFAOYSA-N propan-2-yl 2-cyanopropanoate Chemical compound CC(C)OC(=O)C(C)C#N PVWGZXZMYBHKKP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- OIALIKXMLIAOSN-UHFFFAOYSA-N 2-Propylpyridine Chemical compound CCCC1=CC=CC=N1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 description 1
- PCFUWBOSXMKGIP-UHFFFAOYSA-N 2-benzylpyridine Chemical compound C=1C=CC=NC=1CC1=CC=CC=C1 PCFUWBOSXMKGIP-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-CDYZYAPPSA-N 2-bromopyridine Chemical group BrC1=CC=CC=[15N]1 IMRWILPUOVGIMU-CDYZYAPPSA-N 0.000 description 1
- CCNROCGUORFKEK-UHFFFAOYSA-N 2-ethoxycarbonylbutanedioic acid Chemical compound CCOC(=O)C(C(O)=O)CC(O)=O CCNROCGUORFKEK-UHFFFAOYSA-N 0.000 description 1
- RPXSANFOODTUSQ-UHFFFAOYSA-N 2-ethylhexyl 2-cyanopropanoate Chemical compound CCCCC(CC)COC(=O)C(C)C#N RPXSANFOODTUSQ-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- CCZWSTFVHJPCEM-UHFFFAOYSA-N 2-iodopyridine Chemical compound IC1=CC=CC=N1 CCZWSTFVHJPCEM-UHFFFAOYSA-N 0.000 description 1
- SMTDFMMXJHYDDE-UHFFFAOYSA-N 2-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC=N1 SMTDFMMXJHYDDE-UHFFFAOYSA-N 0.000 description 1
- UUIMDJFBHNDZOW-UHFFFAOYSA-N 2-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC=N1 UUIMDJFBHNDZOW-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- BXYQHDXDCJQOFD-UHFFFAOYSA-N 3-cyanopropanoic acid Chemical compound OC(=O)CCC#N BXYQHDXDCJQOFD-UHFFFAOYSA-N 0.000 description 1
- XJHNCGVHPLDMRK-UHFFFAOYSA-N 4,4-dimethoxybutanenitrile Chemical compound COC(OC)CCC#N XJHNCGVHPLDMRK-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- FYGRPGOHQCPZCV-UHFFFAOYSA-N ethyl 2-cyano-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)C#N FYGRPGOHQCPZCV-UHFFFAOYSA-N 0.000 description 1
- SYKQOFCBFHMCJV-UHFFFAOYSA-N ethyl 2-cyano-3-phenylpropanoate Chemical compound CCOC(=O)C(C#N)CC1=CC=CC=C1 SYKQOFCBFHMCJV-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- FCISHUHNFYJJDU-UHFFFAOYSA-N ethyl 2-cyanobutanoate Chemical compound CCOC(=O)C(CC)C#N FCISHUHNFYJJDU-UHFFFAOYSA-N 0.000 description 1
- BFSBTNGKMMFQNL-UHFFFAOYSA-N ethyl 3-cyanopropanoate Chemical compound CCOC(=O)CCC#N BFSBTNGKMMFQNL-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000010805 inorganic waste Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002699 waste material 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)
- Pyridine Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2639327A DE2639327C2 (de) | 1976-09-01 | 1976-09-01 | Verfahren zur Herstellung von α-substituierten Cyancarbonsäurealkylestern |
| BE180493A BE858185A (fr) | 1976-09-01 | 1977-08-29 | Procede pour l'obtention d'esters alkyliques de l'acide cyanoacetique alpha-substitue |
| IT50823/77A IT1112061B (it) | 1976-09-01 | 1977-08-30 | Procedimento per la produzione di cianacetati alchilici alfa-sostituiti |
| US05/829,177 US4141915A (en) | 1976-09-01 | 1977-08-30 | Method of preparing α-substituted cyanoacetic acid alkyl esters |
| GB7736259A GB1542349A (en) | 1976-09-01 | 1977-08-30 | Process for producing alpha-substituted cyanoacetic acid alkyl esters |
| JP10470477A JPS5331622A (en) | 1976-09-01 | 1977-08-31 | Method of manufacturing alkyl ester of alphaasubstituted cyanoacetic acid |
| NLAANVRAGE7709587,A NL187351C (nl) | 1976-09-01 | 1977-08-31 | Werkwijze voor het bereiden van alfa-gesubstitueerde cyaanazijnzuuralkylesters. |
| FR7726499A FR2363544A1 (fr) | 1976-09-01 | 1977-08-31 | Procede pour l'obtention d'esters alkyliques de l'acide cyanoacetique a substitue |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2639327A DE2639327C2 (de) | 1976-09-01 | 1976-09-01 | Verfahren zur Herstellung von α-substituierten Cyancarbonsäurealkylestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2639327A1 DE2639327A1 (de) | 1978-03-02 |
| DE2639327C2 true DE2639327C2 (de) | 1986-01-16 |
Family
ID=5986892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2639327A Expired DE2639327C2 (de) | 1976-09-01 | 1976-09-01 | Verfahren zur Herstellung von α-substituierten Cyancarbonsäurealkylestern |
Country Status (8)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2751243C1 (ru) * | 2020-12-16 | 2021-07-12 | Общество с ограниченной ответственностью "Интер Групп" | Способ получения 2-этилгексилового эфира 2,4-дихлорфеноксиуксусной кислоты |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4301090A (en) * | 1978-10-30 | 1981-11-17 | Standard Oil Company | Carbonylation of olefinically unsaturated compounds |
| US4331612A (en) * | 1978-12-26 | 1982-05-25 | Standard Oil Company | Carbonylation of olefinically unsaturated compounds |
| US4238357A (en) * | 1979-10-31 | 1980-12-09 | Standard Oil Company | Carbonylation of olefinically unsaturated compounds |
| US4451407A (en) * | 1980-07-16 | 1984-05-29 | The Standard Oil Company | Carbonylation of olefinically unsaturated compounds |
| US4312781A (en) * | 1980-08-06 | 1982-01-26 | Standard Oil Company | Process for the separation of catalyst from products obtained in the hydrocarboxylation of unsaturated nitriles |
| JPS57177168U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1981-05-01 | 1982-11-09 | ||
| JPS57203053A (en) * | 1981-06-09 | 1982-12-13 | Ube Ind Ltd | Preparation of cyanoacetic acid ester |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2506571A (en) * | 1948-08-10 | 1950-05-09 | Du Pont | Acetals from acrylonitrile, carbon monoxide, hydrogen, and alcohols |
| US3146257A (en) * | 1957-11-14 | 1964-08-25 | Montedison Spa | Process for preparing the seminitrile of beta-hydromuconic acid, its chloride and its lower esters, and products thereof |
| NL108510C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1958-12-31 | |||
| US3337603A (en) * | 1958-12-31 | 1967-08-22 | Continuous frocess of preparing formyl carboxylates and cyano aldehydes by the 0x0 reaction | |
| NL272335A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-12-08 | |||
| US3210400A (en) * | 1961-05-18 | 1965-10-05 | Allied Chem | Acetamido-aminocapronitrile, method of making and intermediates therefor |
| DE2403483A1 (de) * | 1974-01-25 | 1975-08-07 | Dynamit Nobel Ag | Verfahren zur herstellung von cyanessigsaeurealkylestern |
-
1976
- 1976-09-01 DE DE2639327A patent/DE2639327C2/de not_active Expired
-
1977
- 1977-08-29 BE BE180493A patent/BE858185A/xx not_active IP Right Cessation
- 1977-08-30 GB GB7736259A patent/GB1542349A/en not_active Expired
- 1977-08-30 IT IT50823/77A patent/IT1112061B/it active
- 1977-08-30 US US05/829,177 patent/US4141915A/en not_active Expired - Lifetime
- 1977-08-31 NL NLAANVRAGE7709587,A patent/NL187351C/xx not_active IP Right Cessation
- 1977-08-31 JP JP10470477A patent/JPS5331622A/ja active Granted
- 1977-08-31 FR FR7726499A patent/FR2363544A1/fr active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2751243C1 (ru) * | 2020-12-16 | 2021-07-12 | Общество с ограниченной ответственностью "Интер Групп" | Способ получения 2-этилгексилового эфира 2,4-дихлорфеноксиуксусной кислоты |
Also Published As
| Publication number | Publication date |
|---|---|
| NL187351B (nl) | 1991-04-02 |
| BE858185A (fr) | 1977-12-16 |
| NL7709587A (nl) | 1978-03-03 |
| US4141915A (en) | 1979-02-27 |
| FR2363544A1 (fr) | 1978-03-31 |
| DE2639327A1 (de) | 1978-03-02 |
| IT1112061B (it) | 1986-01-13 |
| FR2363544B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-09-09 |
| JPS619942B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-03-27 |
| NL187351C (nl) | 1991-09-02 |
| JPS5331622A (en) | 1978-03-25 |
| GB1542349A (en) | 1979-03-14 |
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