IE54389B1 - Process for catalytic hydrolysis of an alpha-amino-nitrile in hererogeneous phase, and polymeric resins having catalytic activity for effecting the process - Google Patents
Process for catalytic hydrolysis of an alpha-amino-nitrile in hererogeneous phase, and polymeric resins having catalytic activity for effecting the processInfo
- Publication number
- IE54389B1 IE54389B1 IE9/83A IE983A IE54389B1 IE 54389 B1 IE54389 B1 IE 54389B1 IE 9/83 A IE9/83 A IE 9/83A IE 983 A IE983 A IE 983A IE 54389 B1 IE54389 B1 IE 54389B1
- Authority
- IE
- Ireland
- Prior art keywords
- process according
- polymeric resin
- aminonitrile
- group
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 61
- 230000008569 process Effects 0.000 title claims abstract description 58
- 239000002952 polymeric resin Substances 0.000 title claims abstract description 52
- 229920003002 synthetic resin Polymers 0.000 title claims abstract description 52
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 20
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 13
- 230000007062 hydrolysis Effects 0.000 title claims abstract description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 40
- -1 hydroxide ions Chemical class 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000002609 medium Substances 0.000 claims abstract description 7
- 239000012736 aqueous medium Substances 0.000 claims abstract description 3
- 229920005989 resin Polymers 0.000 claims description 46
- 239000011347 resin Substances 0.000 claims description 46
- 229920000642 polymer Polymers 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- 239000011159 matrix material Substances 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 16
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- 239000012429 reaction media Substances 0.000 claims description 9
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000012431 aqueous reaction media Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004925 Acrylic resin Substances 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000009471 action Effects 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [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
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000005842 heteroatom 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
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 230000007073 chemical hydrolysis Effects 0.000 claims 1
- 229920005990 polystyrene resin Polymers 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 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000012153 distilled water Substances 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 238000001914 filtration Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 235000008206 alpha-amino acids Nutrition 0.000 description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- HQMLIDZJXVVKCW-UHFFFAOYSA-N 2-aminopropanamide Chemical compound CC(N)C(N)=O HQMLIDZJXVVKCW-UHFFFAOYSA-N 0.000 description 5
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 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 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 150000001371 alpha-amino acids Chemical class 0.000 description 3
- UAMZETBJZRERCQ-UHFFFAOYSA-N alpha-aminopropionitrile Chemical compound CC(N)C#N UAMZETBJZRERCQ-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- WJGQCCPNVRCAQI-UHFFFAOYSA-N 1-cyanoethylazanium;chloride Chemical compound Cl.CC(N)C#N WJGQCCPNVRCAQI-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
- 239000004160 Ammonium persulphate Substances 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 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
- 230000004913 activation Effects 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 235000019395 ammonium persulphate Nutrition 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 150000003997 cyclic ketones Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- XOWUYFUCZLKVEJ-UHFFFAOYSA-N 2-(aminomethylsulfanyl)butanenitrile Chemical compound CCC(C#N)SCN XOWUYFUCZLKVEJ-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
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 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
- 239000004159 Potassium persulphate Substances 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
- 238000007059 Strecker synthesis reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000005844 autocatalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation 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
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 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
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical compound C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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 (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE830009L IE830009L (en) | 1983-07-15 |
| IE54389B1 true IE54389B1 (en) | 1989-09-13 |
Family
ID=9270024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE9/83A IE54389B1 (en) | 1982-01-15 | 1983-01-04 | Process for catalytic hydrolysis of an alpha-amino-nitrile in hererogeneous phase, and polymeric resins having catalytic activity for effecting the process |
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 |
| 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 |
| JPH0450298B2 (en, 2012) | 1992-08-13 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |