CA1316934C - Procede de synthese d'acide glutamique a partir d'acrylates, d'amides et d'un gaz de synthese - Google Patents

Procede de synthese d'acide glutamique a partir d'acrylates, d'amides et d'un gaz de synthese

Info

Publication number: CA1316934C
Authority: CA; Canada
Prior art keywords: cobalt; bis; compound; acrylate; amide
Prior art date: 1987-08-14
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 - Fee Related

Application number

CA000544550A

Other languages

English (en)

Inventor

Jiang-Jen Lin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Texaco Development Corp

Original Assignee

Texaco Development Corp

Priority date (The priority date 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 date listed.)

1987-08-14

Filing date

1987-08-14

Publication date

1993-04-27

1987-08-14 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1987-08-14 Priority to CA000544550A priority Critical patent/CA1316934C/fr

1993-04-27 Application granted granted Critical

1993-04-27 Publication of CA1316934C publication Critical patent/CA1316934C/fr

2010-04-27 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 45
230000008569 process Effects 0.000 title claims abstract description 38
230000015572 biosynthetic process Effects 0.000 title claims abstract description 22
238000003786 synthesis reaction Methods 0.000 title claims abstract description 22
150000001408 amides Chemical class 0.000 title claims abstract description 21
235000013922 glutamic acid Nutrition 0.000 title claims abstract description 20
239000004220 glutamic acid Substances 0.000 title claims abstract description 20
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 title claims abstract description 19
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 16
239000003054 catalyst Substances 0.000 claims abstract description 30
229910017052 cobalt Inorganic materials 0.000 claims abstract description 30
239000010941 cobalt Substances 0.000 claims abstract description 30
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 24
239000003446 ligand Substances 0.000 claims abstract description 15
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 15
239000002904 solvent Substances 0.000 claims abstract description 10
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 27
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
-1 acrylate amide Chemical class 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
RFMMMVDNIPUKGG-YFKPBYRVSA-N N-acetyl-L-glutamic acid Chemical compound CC(=O)N[C@H](C(O)=O)CCC(O)=O RFMMMVDNIPUKGG-YFKPBYRVSA-N 0.000 claims description 9
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000000543 intermediate Substances 0.000 claims description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
GPORFKPYXATYNX-UHFFFAOYSA-N 6-diphenylphosphanylhexyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 GPORFKPYXATYNX-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims description 2
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 2
BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims 4
QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
229910021580 Cobalt(II) chloride Inorganic materials 0.000 claims 1
150000001491 aromatic compounds Chemical class 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 38
239000000047 product Substances 0.000 description 22
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 20
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 16
229910002091 carbon monoxide Inorganic materials 0.000 description 14
229940105305 carbon monoxide Drugs 0.000 description 14
239000000243 solution Substances 0.000 description 11
239000001294 propane Substances 0.000 description 10
150000001299 aldehydes Chemical class 0.000 description 9
239000001257 hydrogen Substances 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
230000000052 comparative effect Effects 0.000 description 8
239000007789 gas Substances 0.000 description 8
238000007037 hydroformylation reaction Methods 0.000 description 8
238000000605 extraction Methods 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
229910021012 Co2(CO)8 Inorganic materials 0.000 description 5
150000001252 acrylic acid derivatives Chemical class 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000010948 rhodium Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000000758 substrate Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000006845 Michael addition reaction Methods 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
230000006315 carbonylation Effects 0.000 description 3
238000005810 carbonylation reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
241000894007 species Species 0.000 description 3
PSKMOUJLASTLRK-YFKPBYRVSA-N (2s)-2-acetamido-5,5,5-trifluoropentanoic acid Chemical compound CC(=O)N[C@H](C(O)=O)CCC(F)(F)F PSKMOUJLASTLRK-YFKPBYRVSA-N 0.000 description 2
FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000004808 allyl alcohols Chemical class 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
150000002310 glutaric acid derivatives Chemical class 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
239000012263 liquid product Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
ZDUVNGAOYJMBKY-SSDOTTSWSA-N (2s)-2-[acetyl(fluoro)amino]-2,3-difluoro-3-methylbutanoic acid Chemical compound CC(=O)N(F)[C@](F)(C(O)=O)C(C)(C)F ZDUVNGAOYJMBKY-SSDOTTSWSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
ZZYSOUTXXFZJBK-UHFFFAOYSA-L butanoate;cobalt(2+) Chemical compound [Co+2].CCCC([O-])=O.CCCC([O-])=O ZZYSOUTXXFZJBK-UHFFFAOYSA-L 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
YMFAWOSEDSLYSZ-UHFFFAOYSA-N carbon monoxide;cobalt Chemical group [Co].[Co].[Co].[Co].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] YMFAWOSEDSLYSZ-UHFFFAOYSA-N 0.000 description 1
239000012018 catalyst precursor Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
229940011182 cobalt acetate Drugs 0.000 description 1
AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 1
PFQLIVQUKOIJJD-UHFFFAOYSA-L cobalt(ii) formate Chemical compound [Co+2].[O-]C=O.[O-]C=O PFQLIVQUKOIJJD-UHFFFAOYSA-L 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000000186 gas chromatography-infrared spectroscopy Methods 0.000 description 1
150000002307 glutamic acids Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229940116335 lauramide Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
MWKMOUILPCFGER-UHFFFAOYSA-N methyl 4,4-diacetamidobutanoate Chemical compound COC(=O)CCC(NC(C)=O)NC(C)=O MWKMOUILPCFGER-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000544550A 1987-08-14 1987-08-14 Procede de synthese d'acide glutamique a partir d'acrylates, d'amides et d'un gaz de synthese Expired - Fee Related CA1316934C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000544550A CA1316934C (fr)	1987-08-14	1987-08-14	Procede de synthese d'acide glutamique a partir d'acrylates, d'amides et d'un gaz de synthese

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000544550A CA1316934C (fr)	1987-08-14	1987-08-14	Procede de synthese d'acide glutamique a partir d'acrylates, d'amides et d'un gaz de synthese

Publications (1)

Publication Number	Publication Date
CA1316934C true CA1316934C (fr)	1993-04-27

Family

ID=4136272

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000544550A Expired - Fee Related CA1316934C (fr)	1987-08-14	1987-08-14	Procede de synthese d'acide glutamique a partir d'acrylates, d'amides et d'un gaz de synthese

Country Status (1)

Country	Link
CA (1)	CA1316934C (fr)

1987
- 1987-08-14 CA CA000544550A patent/CA1316934C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1995-10-29	MKLA	Lapsed

Publication	Publication Date	Title
US4264515A (en)	1981-04-28	Process for manufacturing a N-acyl α-amino acid
EP0207580B1 (fr)	1989-07-26	Procédé pour la préparation de N-acétylaminoacides à partir d'oléfines, d'acétamide et de gaz synthétique
EP0283586A2 (fr)	1988-09-28	Procédé d'homologation
US4620949A (en)	1986-11-04	Process for amidocarbonylation of cyclic amides
CA1296356C (fr)	1992-02-25	PROCEDE POUR LA SYNTHESE DE LA .beta.-PHENYLALAMINE
CA1316934C (fr)	1993-04-27	Procede de synthese d'acide glutamique a partir d'acrylates, d'amides et d'un gaz de synthese
EP0170830B1 (fr)	1989-03-22	Procédé d'amido carbonylation d'aldéhyde en N-acétyl-alpha amino-acides
EP0263624B1 (fr)	1992-12-09	Procédé pour la synthèse d'amino-acides utilisant un catalyseur de cobalt et un ligand phosphine bidentate
US4720573A (en)	1988-01-19	Process for synthesis of glutamic acid from acrylate, amide and synthesis gas
JPH04226946A (ja)	1992-08-17	第二アミンの製造方法
US3947458A (en)	1976-03-30	Preparation of amines
EP0197659B1 (fr)	1989-05-31	Procédé de préparation de la N-acétylglycine employant des promoteurs
US4543411A (en)	1985-09-24	Process for selective preparation of secondary and tertiary amines
US4794199A (en)	1988-12-27	Process for synthesis of primary amines from olefins, syngas and ammonia
US4918222A (en)	1990-04-17	Process for synthesis of N-acetylglycine
EP0313692B1 (fr)	1992-03-25	Procédé de synthèse de l'acide glutamique à partir d'acrylate amide et gaz de synthèse
US4301090A (en)	1981-11-17	Carbonylation of olefinically unsaturated compounds
CA1319702C (fr)	1993-06-29	Procede d'hydroformylation de certains derives d'acide acrylique
US5856590A (en)	1999-01-05	Process for producing cis-4-t-butylcyclohexanol
US5097065A (en)	1992-03-17	Process for synthesis of a novel amino acid from styrene, acetamide and syngas
US4344896A (en)	1982-08-17	Preparation of 2-cyanoaldehydes by rhodium-catalyzed hydroformylation
US4590311A (en)	1986-05-20	Process for the preparation of 1,4-butanediol
CA1267156A (fr)	1990-03-27	Synthese de n-acetylamino-acides a partir d'olefines, d'acetamide et de gaz de synthese
US4866177A (en)	1989-09-12	Process for one-step synthesis of amides
EP0151515B1 (fr)	1991-04-03	Hydroformylation d'alcool allylique