ZA200104125B - Process for preparations of aminocarboxylic acids. - Google Patents
Process for preparations of aminocarboxylic acids. Download PDFInfo
- Publication number
- ZA200104125B ZA200104125B ZA200104125A ZA200104125A ZA200104125B ZA 200104125 B ZA200104125 B ZA 200104125B ZA 200104125 A ZA200104125 A ZA 200104125A ZA 200104125 A ZA200104125 A ZA 200104125A ZA 200104125 B ZA200104125 B ZA 200104125B
- Authority
- ZA
- South Africa
- Prior art keywords
- raney copper
- group
- catalyst
- formula
- amine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 230000008569 process Effects 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims description 43
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 29
- -1 alkali metal salts Chemical class 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 150000003138 primary alcohols Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 239000004327 boric acid Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 150000001734 carboxylic acid salts Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 239000002019 doping agent Substances 0.000 claims 3
- 150000002222 fluorine compounds Chemical class 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 17
- 230000000694 effects Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 230000001737 promoting effect Effects 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 229940031098 ethanolamine Drugs 0.000 description 5
- 150000004673 fluoride salts Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000005470 impregnation Methods 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- FUXALCGRSSRCQE-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-7-yl)ethanamine Chemical compound NCCC1=CC=CC2=C1OCC2 FUXALCGRSSRCQE-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 3
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical class [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000010414 supernatant solution Substances 0.000 description 3
- BCLSJHWBDUYDTR-UHFFFAOYSA-N 2-(propylamino)ethanol Chemical compound CCCNCCO BCLSJHWBDUYDTR-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
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- GKNXYQUXBIFTBT-UHFFFAOYSA-N (3-amino-2-hydroxy-1-phosphonopropyl)phosphonic acid Chemical compound NCC(O)C(P(O)(O)=O)P(O)(O)=O GKNXYQUXBIFTBT-UHFFFAOYSA-N 0.000 description 1
- OWOIXRFDMCACSM-UHFFFAOYSA-N (3-azaniumyl-2-hydroxypropyl)-hydroxyphosphinate Chemical compound NCC(O)CP(O)(O)=O OWOIXRFDMCACSM-UHFFFAOYSA-N 0.000 description 1
- XTVCPVQACKFBDZ-UHFFFAOYSA-N 12-(12-hydroxydodecylamino)dodecan-1-ol Chemical compound OCCCCCCCCCCCCNCCCCCCCCCCCCO XTVCPVQACKFBDZ-UHFFFAOYSA-N 0.000 description 1
- SMBWIEVCKQIHEC-UHFFFAOYSA-N 12-[bis(12-hydroxydodecyl)amino]dodecan-1-ol Chemical compound OCCCCCCCCCCCCN(CCCCCCCCCCCCO)CCCCCCCCCCCCO SMBWIEVCKQIHEC-UHFFFAOYSA-N 0.000 description 1
- AOFLVNRYYFHDPU-UHFFFAOYSA-N 18-aminooctadecan-1-ol Chemical compound NCCCCCCCCCCCCCCCCCCO AOFLVNRYYFHDPU-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- PJNIZPXBKOEEGD-UHFFFAOYSA-N 2-(decylamino)ethanol Chemical compound CCCCCCCCCCNCCO PJNIZPXBKOEEGD-UHFFFAOYSA-N 0.000 description 1
- HCYSJBICYOIBLS-UHFFFAOYSA-N 2-(dodecylamino)ethanol Chemical compound CCCCCCCCCCCCNCCO HCYSJBICYOIBLS-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- MCIKGVLBLIZYRY-UHFFFAOYSA-N 2-(hexylamino)ethanol Chemical compound CCCCCCNCCO MCIKGVLBLIZYRY-UHFFFAOYSA-N 0.000 description 1
- YGCMLNDQGHTAPC-UHFFFAOYSA-N 2-(octadecylamino)ethanol Chemical compound CCCCCCCCCCCCCCCCCCNCCO YGCMLNDQGHTAPC-UHFFFAOYSA-N 0.000 description 1
- UVYBWDBLVDZIOX-UHFFFAOYSA-N 2-(octylamino)ethanol Chemical compound CCCCCCCCNCCO UVYBWDBLVDZIOX-UHFFFAOYSA-N 0.000 description 1
- SALYKAIZVOFAEJ-UHFFFAOYSA-N 2-(pentylamino)ethanol Chemical compound CCCCCNCCO SALYKAIZVOFAEJ-UHFFFAOYSA-N 0.000 description 1
- WUXYGKZSOBYDPP-UHFFFAOYSA-N 2-[bis(2-aminoethyl)amino]ethanol Chemical compound NCCN(CCN)CCO WUXYGKZSOBYDPP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- CXMYWOCYTPKBPP-UHFFFAOYSA-N 3-(3-hydroxypropylamino)propan-1-ol Chemical compound OCCCNCCCO CXMYWOCYTPKBPP-UHFFFAOYSA-N 0.000 description 1
- KRGXWTOLFOPIKV-UHFFFAOYSA-N 3-(methylamino)propan-1-ol Chemical compound CNCCCO KRGXWTOLFOPIKV-UHFFFAOYSA-N 0.000 description 1
- NHIRIMBKJDSLBY-UHFFFAOYSA-N 3-[bis(3-hydroxypropyl)amino]propan-1-ol Chemical compound OCCCN(CCCO)CCCO NHIRIMBKJDSLBY-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FTGIHCSSXPBYMX-UHFFFAOYSA-N 4-(4-hydroxybutylamino)butan-1-ol Chemical compound OCCCCNCCCCO FTGIHCSSXPBYMX-UHFFFAOYSA-N 0.000 description 1
- DBKSSENEKWOVKL-UHFFFAOYSA-N 4-(methylamino)butan-1-ol Chemical compound CNCCCCO DBKSSENEKWOVKL-UHFFFAOYSA-N 0.000 description 1
- WJOZIICADCDCCS-UHFFFAOYSA-N 4-[bis(4-hydroxybutyl)amino]butan-1-ol Chemical compound OCCCCN(CCCCO)CCCCO WJOZIICADCDCCS-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- YELBDMQEYQPIDK-UHFFFAOYSA-N 5-(5-hydroxypentylamino)pentan-1-ol Chemical compound OCCCCCNCCCCCO YELBDMQEYQPIDK-UHFFFAOYSA-N 0.000 description 1
- ZIOGOTUVVZEFMC-UHFFFAOYSA-N 5-[bis(5-hydroxypentyl)amino]pentan-1-ol Chemical compound OCCCCCN(CCCCCO)CCCCCO ZIOGOTUVVZEFMC-UHFFFAOYSA-N 0.000 description 1
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 1
- NGDBBKWQCDEKEA-UHFFFAOYSA-N 6-(6-hydroxyhexylamino)hexan-1-ol Chemical compound OCCCCCCNCCCCCCO NGDBBKWQCDEKEA-UHFFFAOYSA-N 0.000 description 1
- RURWAYHDLRPVAE-UHFFFAOYSA-N 6-(methylamino)hexan-1-ol Chemical compound CNCCCCCCO RURWAYHDLRPVAE-UHFFFAOYSA-N 0.000 description 1
- FOZRYMBTBNNEMP-UHFFFAOYSA-N 6-[bis(6-hydroxyhexyl)amino]hexan-1-ol Chemical compound OCCCCCCN(CCCCCCO)CCCCCCO FOZRYMBTBNNEMP-UHFFFAOYSA-N 0.000 description 1
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 1
- JJHALACYYLLQTC-UHFFFAOYSA-N 8-(8-hydroxyoctylamino)octan-1-ol Chemical compound OCCCCCCCCNCCCCCCCCO JJHALACYYLLQTC-UHFFFAOYSA-N 0.000 description 1
- UVTRSPSKWNCRBY-UHFFFAOYSA-N 8-[bis(8-hydroxyoctyl)amino]octan-1-ol Chemical compound OCCCCCCCCN(CCCCCCCCO)CCCCCCCCO UVTRSPSKWNCRBY-UHFFFAOYSA-N 0.000 description 1
- WDCOJSGXSPGNFK-UHFFFAOYSA-N 8-aminooctan-1-ol Chemical compound NCCCCCCCCO WDCOJSGXSPGNFK-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical class CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-O N-dimethylethanolamine Chemical compound C[NH+](C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-O 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- ZUEIVCHBEQAIAL-UHFFFAOYSA-N N-{2-hydroxyethyl}tetradecan-1-amine Chemical compound CCCCCCCCCCCCCCNCCO ZUEIVCHBEQAIAL-UHFFFAOYSA-N 0.000 description 1
- 229910020808 NaBF Inorganic materials 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 101000870345 Vasconcellea cundinamarcensis Cysteine proteinase 1 Proteins 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 125000001204 arachidyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 125000002704 decyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- 125000003438 dodecyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003187 heptyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000001421 myristyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- XMAXUBOLEVIRGX-UHFFFAOYSA-N phosphanium;fluoride Chemical class [F-].[PH4+] XMAXUBOLEVIRGX-UHFFFAOYSA-N 0.000 description 1
- 229920000447 polyanionic polymer Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J25/00—Catalysts of the Raney type
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH238798 | 1998-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200104125B true ZA200104125B (en) | 2002-01-14 |
Family
ID=4232602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200104125A ZA200104125B (en) | 1998-12-01 | 2001-05-21 | Process for preparations of aminocarboxylic acids. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6541663B2 (pt) |
| EP (1) | EP1140356A1 (pt) |
| JP (1) | JP2002531239A (pt) |
| KR (1) | KR20010080643A (pt) |
| CN (1) | CN1329519A (pt) |
| AU (1) | AU756195B2 (pt) |
| BR (1) | BR9915858A (pt) |
| CA (1) | CA2350750A1 (pt) |
| HU (1) | HUP0104480A3 (pt) |
| ID (1) | ID30119A (pt) |
| IL (1) | IL143139A0 (pt) |
| PL (1) | PL347972A1 (pt) |
| WO (1) | WO2000032310A1 (pt) |
| ZA (1) | ZA200104125B (pt) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6376708B1 (en) | 2000-04-11 | 2002-04-23 | Monsanto Technology Llc | Process and catalyst for dehydrogenating primary alcohols to make carboxylic acid salts |
| EP1436080A2 (en) | 2001-10-18 | 2004-07-14 | Monsanto Technology LLC | Process and catalyst for dehydrogenating primary alcohols to make carboxylic acid salts |
| JP4763455B2 (ja) | 2002-10-18 | 2011-08-31 | モンサント テクノロジー エルエルシー | アルコール改質のための金属支持銅触媒の使用 |
| MX2008016147A (es) | 2006-06-13 | 2009-01-15 | Monsanto Technology Llc | Sistemas de potencia alimentados por alcohol reformado. |
| MX2012010036A (es) | 2010-03-18 | 2012-09-21 | Basf Se | Procedimiento para preparar aminocarboxilatos con bajo contenido de subproductos. |
| JP2011231103A (ja) * | 2010-04-06 | 2011-11-17 | Sumitomo Chemical Co Ltd | 含硫アミノ酸の製造方法 |
| US8865950B2 (en) | 2011-08-10 | 2014-10-21 | Saudi Arabian Oil Company | Olefin hydration process with an integrated membrane reactor |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US529936A (en) * | 1894-11-27 | Ecraseur | ||
| GB642861A (en) * | 1948-08-13 | 1950-09-13 | Peter William Reynolds | Improvements in and relating to the preparation of foraminate catalysts |
| US3928441A (en) * | 1974-08-08 | 1975-12-23 | Nalco Chemical Co | Raney copper catalyst production and use |
| KR950006892B1 (ko) * | 1990-10-23 | 1995-06-26 | 가부시끼가이샤 닛뽕 쇼꾸바이 | 아미노카르복실산 염의 제조방법 |
| US5292936A (en) * | 1993-04-12 | 1994-03-08 | Monsanto Company | Process to prepare amino carboxylic acid salts |
| ATE163403T1 (de) * | 1993-04-12 | 1998-03-15 | Monsanto Co | Verfahren zur herstellung von aminosäuresalzen |
-
1999
- 1999-11-29 KR KR1020017006810A patent/KR20010080643A/ko not_active Application Discontinuation
- 1999-11-29 CA CA002350750A patent/CA2350750A1/en not_active Abandoned
- 1999-11-29 CN CN99814000A patent/CN1329519A/zh active Pending
- 1999-11-29 BR BR9915858-2A patent/BR9915858A/pt not_active Application Discontinuation
- 1999-11-29 ID IDW00200101091A patent/ID30119A/id unknown
- 1999-11-29 HU HU0104480A patent/HUP0104480A3/hu unknown
- 1999-11-29 AU AU17781/00A patent/AU756195B2/en not_active Ceased
- 1999-11-29 WO PCT/EP1999/009267 patent/WO2000032310A1/en not_active Application Discontinuation
- 1999-11-29 PL PL99347972A patent/PL347972A1/xx unknown
- 1999-11-29 EP EP99961024A patent/EP1140356A1/en not_active Withdrawn
- 1999-11-29 JP JP2000584991A patent/JP2002531239A/ja active Pending
- 1999-11-29 IL IL14313999A patent/IL143139A0/xx unknown
-
2001
- 2001-05-21 ZA ZA200104125A patent/ZA200104125B/en unknown
- 2001-06-01 US US09/872,653 patent/US6541663B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000032310A1 (en) | 2000-06-08 |
| EP1140356A1 (en) | 2001-10-10 |
| CN1329519A (zh) | 2002-01-02 |
| BR9915858A (pt) | 2001-08-21 |
| AU756195B2 (en) | 2003-01-09 |
| US6541663B2 (en) | 2003-04-01 |
| HUP0104480A3 (en) | 2003-06-30 |
| AU1778100A (en) | 2000-06-19 |
| JP2002531239A (ja) | 2002-09-24 |
| IL143139A0 (en) | 2002-04-21 |
| ID30119A (id) | 2001-11-08 |
| PL347972A1 (en) | 2002-05-06 |
| CA2350750A1 (en) | 2000-06-08 |
| KR20010080643A (ko) | 2001-08-22 |
| US20020099246A1 (en) | 2002-07-25 |
| HUP0104480A2 (hu) | 2002-03-28 |
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