CA1152523A - Preparation de carbamates a partir d'amines aromatiques et de carbonates organiques - Google Patents

Preparation de carbamates a partir d'amines aromatiques et de carbonates organiques

Info

Publication number: CA1152523A
Authority: CA; Canada
Prior art keywords: zinc; carbonate; divalent tin; catalyst; pka
Prior art date: 1981-05-15
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

Application number

CA000377718A

Other languages

English (en)

Inventor

Arthur E. Gurgiolo

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.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

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.)

1981-05-15

Filing date

1981-05-15

Publication date

1983-08-23

1981-05-15 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1981-05-15 Priority to CA000377718A priority Critical patent/CA1152523A/fr

1983-08-23 Application granted granted Critical

1983-08-23 Publication of CA1152523A publication Critical patent/CA1152523A/fr

Status Expired legal-status Critical Current

Links

150000004982 aromatic amines Chemical class 0.000 title claims abstract description 9
150000005677 organic carbonates Chemical class 0.000 title claims description 8
150000004657 carbamic acid derivatives Chemical class 0.000 title description 3
238000002360 preparation method Methods 0.000 title description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 19
239000011701 zinc Substances 0.000 claims abstract description 19
229910052725 zinc Inorganic materials 0.000 claims abstract description 19
238000006243 chemical reaction Methods 0.000 claims abstract description 14
-1 tin halide Chemical class 0.000 claims abstract description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 10
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 9
229910021626 Tin(II) chloride Inorganic materials 0.000 claims abstract description 9
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 8
150000002894 organic compounds Chemical class 0.000 claims abstract description 6
239000011968 lewis acid catalyst Substances 0.000 claims abstract description 5
239000011541 reaction mixture Substances 0.000 claims abstract description 4
230000003197 catalytic effect Effects 0.000 claims abstract description 3
238000004519 manufacturing process Methods 0.000 claims abstract description 3
239000003054 catalyst Substances 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 8
WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical group [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 claims description 5
239000004246 zinc acetate Substances 0.000 claims description 5
CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims description 5
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 4
238000000034 method Methods 0.000 claims description 3
XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 6
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 6
239000000376 reactant Substances 0.000 description 6
150000001412 amines Chemical class 0.000 description 5
HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 2
GWXQNFKETHVQIZ-UHFFFAOYSA-N 2-methylbenzene-1,3-diamine;4-methylbenzene-1,3-diamine Chemical compound CC1=CC=C(N)C=C1N.CC1=C(N)C=CC=C1N GWXQNFKETHVQIZ-UHFFFAOYSA-N 0.000 description 2
DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical group CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
229940058401 polytetrafluoroethylene Drugs 0.000 description 2
239000004810 polytetrafluoroethylene Substances 0.000 description 2
235000011150 stannous chloride Nutrition 0.000 description 2
239000001119 stannous chloride Substances 0.000 description 2
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
JCMLRUNDSXARRW-UHFFFAOYSA-N trioxouranium Chemical compound O=[U](=O)=O JCMLRUNDSXARRW-UHFFFAOYSA-N 0.000 description 2
YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 2
150000003751 zinc Chemical class 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 2
HQBBDVUXOOMFQN-UHFFFAOYSA-L zinc;2,2-dimethylpropanoate Chemical compound [Zn+2].CC(C)(C)C([O-])=O.CC(C)(C)C([O-])=O HQBBDVUXOOMFQN-UHFFFAOYSA-L 0.000 description 2
YEOOSEARUBCNSL-UHFFFAOYSA-L zinc;2-chloroacetate Chemical compound [Zn+2].[O-]C(=O)CCl.[O-]C(=O)CCl YEOOSEARUBCNSL-UHFFFAOYSA-L 0.000 description 2
JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 2
YMTQMTSQMKJKPX-UHFFFAOYSA-L zinc;diphenoxide Chemical compound [Zn+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 YMTQMTSQMKJKPX-UHFFFAOYSA-L 0.000 description 2
NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 2
XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 2
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 description 1
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 1
RPXFDOOFVNTCQA-UHFFFAOYSA-N 2-cyclohexylbutanoic acid Chemical compound CCC(C(O)=O)C1CCCCC1 RPXFDOOFVNTCQA-UHFFFAOYSA-N 0.000 description 1
QKRLPMFIDBFKJJ-UHFFFAOYSA-N 2-methylidenebutanedioic acid;zinc Chemical compound [Zn].OC(=O)CC(=C)C(O)=O QKRLPMFIDBFKJJ-UHFFFAOYSA-N 0.000 description 1
SROVXQAFQQWQEO-UHFFFAOYSA-N 3-(2-carboxyethylsulfanyl)propanoic acid;zinc Chemical compound [Zn].OC(=O)CCSCCC(O)=O SROVXQAFQQWQEO-UHFFFAOYSA-N 0.000 description 1
IPWGAPCYYMTTLT-UHFFFAOYSA-N 3-propylaniline Chemical compound CCCC1=CC=CC(N)=C1 IPWGAPCYYMTTLT-UHFFFAOYSA-N 0.000 description 1
ZKOGUIGAVNCCKH-UHFFFAOYSA-N 4-phenyl-1,3-dioxolan-2-one Chemical compound O1C(=O)OCC1C1=CC=CC=C1 ZKOGUIGAVNCCKH-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
241001074085 Scophthalmus aquosus Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
FWBMVXOCTXTBAD-UHFFFAOYSA-N butyl methyl carbonate Chemical compound CCCCOC(=O)OC FWBMVXOCTXTBAD-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical compound OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
OKQDSOXFNBWWJL-UHFFFAOYSA-N dihexyl carbonate Chemical compound CCCCCCOC(=O)OCCCCCC OKQDSOXFNBWWJL-UHFFFAOYSA-N 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 description 1
JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 description 1
XTBFPVLHGVYOQH-UHFFFAOYSA-N methyl phenyl carbonate Chemical compound COC(=O)OC1=CC=CC=C1 XTBFPVLHGVYOQH-UHFFFAOYSA-N 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 1
OOAWCECZEHPMBX-UHFFFAOYSA-N oxygen(2-);uranium(4+) Chemical compound [O-2].[O-2].[U+4] OOAWCECZEHPMBX-UHFFFAOYSA-N 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920001343 polytetrafluoroethylene Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000004576 sand Substances 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
FCTBKIHDJGHPPO-UHFFFAOYSA-N uranium dioxide Inorganic materials O=[U]=O FCTBKIHDJGHPPO-UHFFFAOYSA-N 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
VCQWRGCXUWPSGY-UHFFFAOYSA-L zinc;2,2,2-trifluoroacetate Chemical compound [Zn+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F VCQWRGCXUWPSGY-UHFFFAOYSA-L 0.000 description 1
DQFGQDPDTGTFFJ-UHFFFAOYSA-L zinc;4-chlorobenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=C(Cl)C=C1.[O-]C(=O)C1=CC=C(Cl)C=C1 DQFGQDPDTGTFFJ-UHFFFAOYSA-L 0.000 description 1
JXNCWJJAQLTWKR-UHFFFAOYSA-N zinc;methanolate Chemical compound [Zn+2].[O-]C.[O-]C JXNCWJJAQLTWKR-UHFFFAOYSA-N 0.000 description 1
ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1

Landscapes

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

CA000377718A 1981-05-15 1981-05-15 Preparation de carbamates a partir d'amines aromatiques et de carbonates organiques Expired CA1152523A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000377718A CA1152523A (fr)	1981-05-15	1981-05-15	Preparation de carbamates a partir d'amines aromatiques et de carbonates organiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000377718A CA1152523A (fr)	1981-05-15	1981-05-15	Preparation de carbamates a partir d'amines aromatiques et de carbonates organiques

Publications (1)

Publication Number	Publication Date
CA1152523A true CA1152523A (fr)	1983-08-23

Family

ID=4119968

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000377718A Expired CA1152523A (fr)	1981-05-15	1981-05-15	Preparation de carbamates a partir d'amines aromatiques et de carbonates organiques

Country Status (1)

Country	Link
CA (1)	CA1152523A (fr)

1981
- 1981-05-15 CA CA000377718A patent/CA1152523A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-08-23	MKEX	Expiry

Publication	Publication Date	Title
US4268683A (en)	1981-05-19	Preparation of carbamates from aromatic amines and organic carbonates
US4268684A (en)	1981-05-19	Preparation of carbamates from aromatic amines and organic carbonates
US4410464A (en)	1983-10-18	Diaryl carbonate process
EP0065026A1 (fr)	1982-11-24	Préparation de carbamates à partir d'amines aromatiques et de carbonates organiques
US4659865A (en)	1987-04-21	Process for producing ethylidenediacetate
US4552704A (en)	1985-11-12	Process for the production of aromatic carbonates
EP0583937B1 (fr)	1997-01-22	Méthode de fabrication de carbonates aromatiques organiques
Calderazzo	1965	The Manganese-Catalyzed Carbonylation of Amines
EP0071286B1 (fr)	1985-08-28	Procédé de préparation des esters de l'acide carbonique
US5698731A (en)	1997-12-16	Process for the production of aromatic carbamates
US4550188A (en)	1985-10-29	Preparation of carbamates
US4322530A (en)	1982-03-30	Alkylation of polyamines
US5252771A (en)	1993-10-12	Aluminum trifluoride catalyst for production of diaryl carbonates
KR20010013407A (fr)	2001-02-26	Procede de preparation de carbamates
US4258200A (en)	1981-03-24	Production of carboxylic acid amides and carbamates using cobalt catalysts
US4604242A (en)	1986-08-05	Preparation of dialiphatic, dialicyclic, or di(aryl-substituted aliphatic) carbonates
US4670598A (en)	1987-06-02	Process for preparing (hydrocarbylthio)aromatic amines
FI67872C (fi)	1985-06-10	Foerfarande foer framstaellning av polymer polyamin/amid
EP0065025A1 (fr)	1982-11-24	Préparation de carbamates à partir d'amines aromatiques et de carbonates organiques
JPH107593A (ja)	1998-01-13	１−ヘキセンの製造方法
US4539427A (en)	1985-09-03	Process for the preparation of formamides
CA1258870A (fr)	1989-08-29	Carbonylation d'hydrocarbures halogenes a haut rendement
JPH01265063A (ja)	1989-10-23	芳香族カーボネート化合物を製造する方法
CA1152524A (fr)	1983-08-23	Preparation de carbamates a partir d'amines aromatiques et de carbonates organiques
JP3396911B2 (ja)	2003-04-14	α−オレフィンの低重合方法