GB1580533A - Cyanoacetic acid esters - Google Patents
Cyanoacetic acid esters Download PDFInfo
- Publication number
- GB1580533A GB1580533A GB2826176A GB2826176A GB1580533A GB 1580533 A GB1580533 A GB 1580533A GB 2826176 A GB2826176 A GB 2826176A GB 2826176 A GB2826176 A GB 2826176A GB 1580533 A GB1580533 A GB 1580533A
- Authority
- GB
- United Kingdom
- Prior art keywords
- process according
- general formula
- group
- methyl
- transfer 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
Links
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- -1 alkali metal salt Chemical class 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 7
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 7
- LZLSUHMFFPVWGU-UHFFFAOYSA-N 3-methylbut-2-enyl 2-cyanoacetate Chemical compound CC(C)=CCOC(=O)CC#N LZLSUHMFFPVWGU-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 150000008282 halocarbons Chemical group 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052785 arsenic Chemical group 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Chemical group 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims 1
- 230000009102 absorption Effects 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 abstract description 8
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000000575 pesticide Substances 0.000 abstract description 3
- 235000013350 formula milk Nutrition 0.000 description 23
- 239000000203 mixture Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- JKXQKGNGJVZKFA-UHFFFAOYSA-N 1-chloro-3-methylbut-2-ene Chemical compound CC(C)=CCCl JKXQKGNGJVZKFA-UHFFFAOYSA-N 0.000 description 3
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical group C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004996 alkyl benzenes Chemical class 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- CUPOLFAOTCIXBB-UHFFFAOYSA-N 3-methylbut-2-enyl 2-cyano-5-methylhex-4-enoate Chemical compound CC(C)=CCOC(=O)C(C#N)CC=C(C)C CUPOLFAOTCIXBB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- KYVISUNMHKSREJ-UHFFFAOYSA-M potassium;2-cyanoacetate Chemical compound [K+].[O-]C(=O)CC#N KYVISUNMHKSREJ-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UHSQYBCECUMBRE-UHFFFAOYSA-N 1,2,3,4,5,8,9-heptaoxacyclotricos-6-ene Chemical compound C1CCCCCCCOOC=COOOOOCCCCCC1 UHSQYBCECUMBRE-UHFFFAOYSA-N 0.000 description 1
- YUACDUKFVCTPKB-UHFFFAOYSA-N 2-(2,2-dichloroethenyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C=C(Cl)Cl YUACDUKFVCTPKB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical group [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 239000011363 dried mixture Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MBKRVLHRAHLOEC-UHFFFAOYSA-M ethyl-(2-methylpentadecyl)-(2-methylundecyl)sulfanium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCCCCCCCCCCCCC(C)C[S+](CC)CC(C)CCCCCCCCC MBKRVLHRAHLOEC-UHFFFAOYSA-M 0.000 description 1
- WUTHHSVDMNYUKB-UHFFFAOYSA-M ethyl-(2-methylpentyl)-(2-methylundecyl)sulfanium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCCCCCCCCC(C)C[S+](CC)CC(C)CCC WUTHHSVDMNYUKB-UHFFFAOYSA-M 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- KTRVRLMHICTFHP-UHFFFAOYSA-M hexadecyl(dimethyl)sulfanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCC[S+](C)C KTRVRLMHICTFHP-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- GHLKOMSNOFJXDT-UHFFFAOYSA-M methyl(triphenyl)arsanium;iodide Chemical compound [I-].C=1C=CC=CC=1[As+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 GHLKOMSNOFJXDT-UHFFFAOYSA-M 0.000 description 1
- IRRWVJRKCPFQIB-UHFFFAOYSA-M methyl-di(nonyl)sulfanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCCCCCC[S+](C)CCCCCCCCC IRRWVJRKCPFQIB-UHFFFAOYSA-M 0.000 description 1
- VPGLEBSOGIEMPX-UHFFFAOYSA-M methyl-tris(2-methylheptyl)azanium;chloride Chemical compound [Cl-].CCCCCC(C)C[N+](C)(CC(C)CCCCC)CC(C)CCCCC VPGLEBSOGIEMPX-UHFFFAOYSA-M 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- TVVPMLFGPYQGTG-UHFFFAOYSA-M tetramethylphosphanium;iodide Chemical compound [I-].C[P+](C)(C)C TVVPMLFGPYQGTG-UHFFFAOYSA-M 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 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 (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2826176A GB1580533A (en) | 1976-07-07 | 1976-07-07 | Cyanoacetic acid esters |
| CA279,044A CA1123007A (en) | 1976-07-07 | 1977-05-24 | Preparation of esters |
| JP7957677A JPS537621A (en) | 1976-07-07 | 1977-07-05 | Method of manufacturing esters |
| IT2540977A IT1143740B (it) | 1976-07-07 | 1977-07-05 | Processo per la preparazione di esteri dell'acido cianacetico |
| BE179091A BE856489A (fr) | 1976-07-07 | 1977-07-05 | Preparation d'un ester d'acide cyanoacetique et composes obtenus |
| FR7720604A FR2357533A1 (fr) | 1976-07-07 | 1977-07-05 | Preparation d'un ester d'acide cyanoacetique et composes obtenus |
| NL7707417A NL188638C (nl) | 1976-07-07 | 1977-07-05 | Werkwijze ter bereiding van esters van cyaanazijnzuur. |
| BR7704405A BR7704405A (pt) | 1976-07-07 | 1977-07-05 | Processo para a preparacao de um ester do acido cianoacetico |
| CH825177A CH628879A5 (en) | 1976-07-07 | 1977-07-05 | Process for the preparation of cyanoacetic esters |
| DK302677A DK156954C (da) | 1976-07-07 | 1977-07-05 | Fremgangsmaade til fremstilling af cyanoeddikesyreestere |
| DE19772730332 DE2730332A1 (de) | 1976-07-07 | 1977-07-05 | Ester der cyanoessigsaeure und verfahren zu ihrer herstellung |
| MX587577U MX4913E (es) | 1976-07-07 | 1977-07-05 | Procedimiento para preparar un ester del acido cianoacetico |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2826176A GB1580533A (en) | 1976-07-07 | 1976-07-07 | Cyanoacetic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1580533A true GB1580533A (en) | 1980-12-03 |
Family
ID=10272858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2826176A Expired GB1580533A (en) | 1976-07-07 | 1976-07-07 | Cyanoacetic acid esters |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS537621A (enExample) |
| BE (1) | BE856489A (enExample) |
| BR (1) | BR7704405A (enExample) |
| CA (1) | CA1123007A (enExample) |
| CH (1) | CH628879A5 (enExample) |
| DE (1) | DE2730332A1 (enExample) |
| DK (1) | DK156954C (enExample) |
| FR (1) | FR2357533A1 (enExample) |
| GB (1) | GB1580533A (enExample) |
| IT (1) | IT1143740B (enExample) |
| MX (1) | MX4913E (enExample) |
| NL (1) | NL188638C (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2471973A1 (fr) * | 1979-12-20 | 1981-06-26 | Rhone Poulenc Ind | Procede de preparation de cyanoacetates d'alkyle |
| JPS5954767U (ja) * | 1982-10-01 | 1984-04-10 | トヨタ自動車株式会社 | 自動車エンジン用イグナイタ |
-
1976
- 1976-07-07 GB GB2826176A patent/GB1580533A/en not_active Expired
-
1977
- 1977-05-24 CA CA279,044A patent/CA1123007A/en not_active Expired
- 1977-07-05 JP JP7957677A patent/JPS537621A/ja active Granted
- 1977-07-05 BE BE179091A patent/BE856489A/xx not_active IP Right Cessation
- 1977-07-05 MX MX587577U patent/MX4913E/es unknown
- 1977-07-05 IT IT2540977A patent/IT1143740B/it active
- 1977-07-05 DK DK302677A patent/DK156954C/da not_active IP Right Cessation
- 1977-07-05 NL NL7707417A patent/NL188638C/xx not_active IP Right Cessation
- 1977-07-05 FR FR7720604A patent/FR2357533A1/fr active Granted
- 1977-07-05 CH CH825177A patent/CH628879A5/de not_active IP Right Cessation
- 1977-07-05 BR BR7704405A patent/BR7704405A/pt unknown
- 1977-07-05 DE DE19772730332 patent/DE2730332A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE2730332A1 (de) | 1978-01-12 |
| JPS618823B2 (enExample) | 1986-03-18 |
| CH628879A5 (en) | 1982-03-31 |
| DK156954B (da) | 1989-10-23 |
| NL188638B (nl) | 1992-03-16 |
| JPS537621A (en) | 1978-01-24 |
| BE856489A (fr) | 1978-01-05 |
| FR2357533B1 (enExample) | 1981-01-09 |
| NL188638C (nl) | 1992-08-17 |
| BR7704405A (pt) | 1978-05-02 |
| MX4913E (es) | 1983-01-03 |
| NL7707417A (nl) | 1978-01-10 |
| DK302677A (da) | 1978-01-08 |
| FR2357533A1 (fr) | 1978-02-03 |
| IT1143740B (it) | 1986-10-22 |
| CA1123007A (en) | 1982-05-04 |
| DK156954C (da) | 1990-02-26 |
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| Date | Code | Title | Description |
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| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940705 |