JPH0450298B2 - - Google Patents
Info
- Publication number
- JPH0450298B2 JPH0450298B2 JP58003615A JP361583A JPH0450298B2 JP H0450298 B2 JPH0450298 B2 JP H0450298B2 JP 58003615 A JP58003615 A JP 58003615A JP 361583 A JP361583 A JP 361583A JP H0450298 B2 JPH0450298 B2 JP H0450298B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- polymer resin
- group
- general formula
- matrix
- 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
- 239000002952 polymeric resin Substances 0.000 claims description 68
- 229920003002 synthetic resin Polymers 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 54
- 229920000642 polymer Polymers 0.000 claims description 44
- 229920005989 resin Polymers 0.000 claims description 43
- 239000011347 resin Substances 0.000 claims description 43
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 239000011159 matrix material Substances 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 25
- -1 hydroxide ions Chemical class 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 230000003197 catalytic effect Effects 0.000 claims description 12
- 150000003997 cyclic ketones Chemical class 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 8
- 239000004793 Polystyrene Substances 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 5
- 239000012431 aqueous reaction media Substances 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 4
- 125000005219 aminonitrile group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 150000003512 tertiary amines Chemical group 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Chemical class 0.000 claims description 2
- 239000000908 ammonium hydroxide Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003857 carboxamides Chemical group 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229920005990 polystyrene resin Polymers 0.000 claims 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 150000003141 primary amines Chemical group 0.000 claims 2
- 150000003335 secondary amines Chemical group 0.000 claims 2
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 150000002576 ketones Chemical group 0.000 description 19
- 239000012153 distilled water Substances 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000000468 ketone group Chemical group 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
- WJGQCCPNVRCAQI-UHFFFAOYSA-N 1-cyanoethylazanium;chloride Chemical compound Cl.CC(N)C#N WJGQCCPNVRCAQI-UHFFFAOYSA-N 0.000 description 6
- HQMLIDZJXVVKCW-UHFFFAOYSA-N 2-aminopropanamide Chemical compound CC(N)C(N)=O HQMLIDZJXVVKCW-UHFFFAOYSA-N 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- UAMZETBJZRERCQ-UHFFFAOYSA-N alpha-aminopropionitrile Chemical compound CC(N)C#N UAMZETBJZRERCQ-UHFFFAOYSA-N 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 230000006315 carbonylation Effects 0.000 description 4
- 238000005810 carbonylation reaction Methods 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- GZGPRZYZKBQPBQ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decane Chemical compound O1CCOC11CCCCC1 GZGPRZYZKBQPBQ-UHFFFAOYSA-N 0.000 description 3
- UDCTUXCXMQODNP-UHFFFAOYSA-N 1-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)prop-2-en-1-one Chemical compound C1CN(C(=O)C=C)CCC21OCCO2 UDCTUXCXMQODNP-UHFFFAOYSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 235000004279 alanine Nutrition 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical compound C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 description 3
- YERHJBPPDGHCRJ-UHFFFAOYSA-N 1-[4-(1-oxoprop-2-enyl)-1-piperazinyl]-2-propen-1-one Chemical compound C=CC(=O)N1CCN(C(=O)C=C)CC1 YERHJBPPDGHCRJ-UHFFFAOYSA-N 0.000 description 2
- XOWUYFUCZLKVEJ-UHFFFAOYSA-N 2-(aminomethylsulfanyl)butanenitrile Chemical compound CCC(C#N)SCN XOWUYFUCZLKVEJ-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001371 alpha-amino acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KPKNTUUIEVXMOH-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1CCOC11CCNCC1 KPKNTUUIEVXMOH-UHFFFAOYSA-N 0.000 description 1
- KZMOKRZFRDUFHC-UHFFFAOYSA-N 2-(aminomethylsulfanyl)butanamide Chemical compound CCC(C(N)=O)SCN KZMOKRZFRDUFHC-UHFFFAOYSA-N 0.000 description 1
- TYDSIOSLHQWFOU-UHFFFAOYSA-N 2-cyclohexylidenecyclohexan-1-one Chemical compound O=C1CCCCC1=C1CCCCC1 TYDSIOSLHQWFOU-UHFFFAOYSA-N 0.000 description 1
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000005844 autocatalytic reaction Methods 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004980 dosimetry Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/38—Amides
- C08F222/385—Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8200600A FR2519973A1 (fr) | 1982-01-15 | 1982-01-15 | Procede d'hydrolyse catalytique d'un alpha-amino-nitrile en phase heterogene, ainsi que les resines polymeres a activite catalytique pour la mise en oeuvre du procede |
| FR8200600 | 1982-01-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58170738A JPS58170738A (ja) | 1983-10-07 |
| JPH0450298B2 true JPH0450298B2 (en, 2012) | 1992-08-13 |
Family
ID=9270024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58003615A Granted JPS58170738A (ja) | 1982-01-15 | 1983-01-14 | 不均一相に於けるα−アミノ・ニトリルの接触加水分解法及びこの方法を実施するための触媒活性ポリマ−樹脂 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4851576A (en, 2012) |
| EP (1) | EP0084470B1 (en, 2012) |
| JP (1) | JPS58170738A (en, 2012) |
| KR (1) | KR870000184B1 (en, 2012) |
| BR (1) | BR8300179A (en, 2012) |
| CA (1) | CA1186331A (en, 2012) |
| CS (1) | CS235978B2 (en, 2012) |
| DD (1) | DD208349A5 (en, 2012) |
| DE (1) | DE3367087D1 (en, 2012) |
| ES (1) | ES8308527A1 (en, 2012) |
| FR (1) | FR2519973A1 (en, 2012) |
| HU (1) | HU199107B (en, 2012) |
| IE (1) | IE54389B1 (en, 2012) |
| MX (1) | MX162837B (en, 2012) |
| PL (1) | PL138342B1 (en, 2012) |
| SU (1) | SU1316554A3 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2565225B1 (fr) * | 1984-06-05 | 1986-10-17 | Centre Nat Rech Scient | Procede de synthese en continu d'un a-amino-acide par hydrolyse catalytique chimique et dispositif pour la mise en oeuvre du procede |
| JPS63179877A (ja) * | 1987-01-19 | 1988-07-23 | Agency Of Ind Science & Technol | 新規なビニル化合物 |
| DE4235295A1 (de) * | 1992-10-20 | 1994-04-21 | Degussa | Kontinuierlich durchführbares Verfahren zur Herstellung von Methionin oder Methioninderivaten |
| FR2785609B1 (fr) * | 1998-11-06 | 2000-12-15 | Rhone Poulenc Nutrition Animal | Procede de preparation de la methionine |
| EP3632894A1 (de) | 2018-10-01 | 2020-04-08 | Evonik Operations GmbH | Nebenproduktarme herstellung von methionin aus methioninnitril |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3041375A (en) * | 1959-07-06 | 1962-06-26 | Dow Chemical Co | Preparation of acrylamide |
| US3062883A (en) * | 1960-07-13 | 1962-11-06 | Allied Chem | Preparation of alkanoic acid amides through hydrolysis of alkyl cyanides |
| US3190917A (en) * | 1961-06-08 | 1965-06-22 | Union Carbide Corp | Synthesis of alpha-amino acid amide hydrohalides |
| ES360165A1 (es) * | 1966-09-22 | 1970-07-01 | Lubrizol Corp | Un metodo para eliminar impurezas disueltas del agua. |
| US3674848A (en) * | 1970-08-19 | 1972-07-04 | American Cyanamid Co | Hydration of nitriles using metal salts of cation exchange resins |
| US4036879A (en) * | 1970-11-19 | 1977-07-19 | The Dow Chemical Company | Catalysts for the hydration of nitriles of amides |
| FR2372797A1 (fr) * | 1976-12-03 | 1978-06-30 | Anvar | Procede d'hydrolyse catalytique chimique d'a-amino-nitriles ou de leurs sels |
| US4202694A (en) * | 1977-04-21 | 1980-05-13 | Polaroid Corporation | Pendant oxime polymers and photographic use thereof |
| FR2405924A1 (fr) * | 1977-10-12 | 1979-05-11 | Anvar | Procede de preparation d'a-amino-acides |
-
1982
- 1982-01-15 FR FR8200600A patent/FR2519973A1/fr active Granted
- 1982-12-28 US US06/454,003 patent/US4851576A/en not_active Expired - Fee Related
- 1982-12-30 ES ES518688A patent/ES8308527A1/es not_active Expired
- 1982-12-31 CA CA000418818A patent/CA1186331A/en not_active Expired
-
1983
- 1983-01-04 IE IE9/83A patent/IE54389B1/en not_active IP Right Cessation
- 1983-01-05 DE DE8383400024T patent/DE3367087D1/de not_active Expired
- 1983-01-05 EP EP83400024A patent/EP0084470B1/fr not_active Expired
- 1983-01-11 SU SU833534108A patent/SU1316554A3/ru active
- 1983-01-12 CS CS83223A patent/CS235978B2/cs unknown
- 1983-01-13 MX MX195905A patent/MX162837B/es unknown
- 1983-01-14 JP JP58003615A patent/JPS58170738A/ja active Granted
- 1983-01-14 KR KR1019830000109A patent/KR870000184B1/ko not_active Expired
- 1983-01-14 PL PL1983240171A patent/PL138342B1/pl unknown
- 1983-01-14 BR BR8300179A patent/BR8300179A/pt not_active IP Right Cessation
- 1983-01-14 DD DD83247257A patent/DD208349A5/de not_active IP Right Cessation
- 1983-01-14 HU HU83131A patent/HU199107B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL138342B1 (en) | 1986-09-30 |
| FR2519973B1 (en, 2012) | 1985-04-26 |
| CA1186331A (en) | 1985-04-30 |
| FR2519973A1 (fr) | 1983-07-22 |
| DE3367087D1 (en) | 1986-11-27 |
| IE54389B1 (en) | 1989-09-13 |
| IE830009L (en) | 1983-07-15 |
| HU199107B (en) | 1990-01-29 |
| PL240171A1 (en) | 1983-09-26 |
| EP0084470B1 (fr) | 1986-10-22 |
| ES518688A0 (es) | 1983-10-01 |
| CS235978B2 (en) | 1985-05-15 |
| KR840003233A (ko) | 1984-08-20 |
| BR8300179A (pt) | 1983-10-11 |
| US4851576A (en) | 1989-07-25 |
| KR870000184B1 (ko) | 1987-02-14 |
| SU1316554A3 (ru) | 1987-06-07 |
| ES8308527A1 (es) | 1983-10-01 |
| EP0084470A1 (fr) | 1983-07-27 |
| JPS58170738A (ja) | 1983-10-07 |
| DD208349A5 (de) | 1984-05-02 |
| HUT34374A (en) | 1985-03-28 |
| MX162837B (es) | 1991-06-28 |
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