CA1257607A - Methode de preparation d'urethanes - Google Patents

Methode de preparation d'urethanes

Info

Publication number: CA1257607A
Authority: CA; Canada
Prior art keywords: nitrogen; bis; compound; ruthenium; containing organic
Prior art date: 1983-09-16
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

CA000575485A

Other languages

English (en)

Inventor

John H. Grate

David R. Hamm

Donald H. Valentine

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.)

Topsoe AS

Catalytica Inc

Original Assignee

Haldor Topsoe AS

Catalytica Inc

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.)

1983-09-16

Filing date

1988-08-23

Publication date

1989-07-18

1983-09-16 Priority claimed from US06/532,784 external-priority patent/US4600793A/en

1983-09-16 Priority claimed from US06/532,785 external-priority patent/US4603216A/en

1984-09-14 Priority claimed from CA000463144A external-priority patent/CA1244466A/fr

1988-08-23 Application filed by Haldor Topsoe AS, Catalytica Inc filed Critical Haldor Topsoe AS

1988-08-23 Priority to CA000575485A priority Critical patent/CA1257607A/fr

1989-07-18 Application granted granted Critical

1989-07-18 Publication of CA1257607A publication Critical patent/CA1257607A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 48
230000008569 process Effects 0.000 title claims abstract description 28
150000003673 urethanes Chemical class 0.000 title description 9
238000002360 preparation method Methods 0.000 title description 5
-1 nitrogen-containing organic compound Chemical class 0.000 claims abstract description 105
239000003054 catalyst Substances 0.000 claims abstract description 59
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 47
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 46
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 32
239000003446 ligand Substances 0.000 claims abstract description 32
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 26
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
150000002894 organic compounds Chemical class 0.000 claims abstract description 14
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 12
125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims abstract description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 108
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 77
238000006243 chemical reaction Methods 0.000 claims description 76
150000003141 primary amines Chemical class 0.000 claims description 42
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
150000002828 nitro derivatives Chemical class 0.000 claims description 16
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 10
239000007789 gas Substances 0.000 claims description 9
238000011065 in-situ storage Methods 0.000 claims description 8
239000004202 carbamide Substances 0.000 claims description 7
230000009467 reduction Effects 0.000 claims description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 3
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 description 2
GLBZQZXDUTUCGK-UHFFFAOYSA-N 1-nitro-4-[(4-nitrophenyl)methyl]benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 GLBZQZXDUTUCGK-UHFFFAOYSA-N 0.000 claims description 2
DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 claims description 2
150000004982 aromatic amines Chemical class 0.000 claims description 2
SCEKDQTVGHRSNS-UHFFFAOYSA-N 1,3,5-trimethyl-2-nitrobenzene Chemical group CC1=CC(C)=C([N+]([O-])=O)C(C)=C1 SCEKDQTVGHRSNS-UHFFFAOYSA-N 0.000 claims 1
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 1
VDCZKCIEXGXCDJ-UHFFFAOYSA-N 3-methyl-2-nitroaniline Chemical compound CC1=CC=CC(N)=C1[N+]([O-])=O VDCZKCIEXGXCDJ-UHFFFAOYSA-N 0.000 claims 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims 1
BNUHAJGCKIQFGE-UHFFFAOYSA-N Nitroanisol Chemical compound COC1=CC=C([N+]([O-])=O)C=C1 BNUHAJGCKIQFGE-UHFFFAOYSA-N 0.000 claims 1
239000013522 chelant Substances 0.000 claims 1
OCAAQQIPYFCKIK-UHFFFAOYSA-N nitro(phenyl)methanamine Chemical compound [O-][N+](=O)C(N)C1=CC=CC=C1 OCAAQQIPYFCKIK-UHFFFAOYSA-N 0.000 claims 1
RFASNSQFGZUUBB-UHFFFAOYSA-N phenyl-(2-phenylphosphanylphenyl)phosphane Chemical compound C=1C=CC=C(PC=2C=CC=CC=2)C=1PC1=CC=CC=C1 RFASNSQFGZUUBB-UHFFFAOYSA-N 0.000 claims 1
DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 claims 1
229960005088 urethane Drugs 0.000 abstract description 29
150000003304 ruthenium compounds Chemical class 0.000 description 24
150000001875 compounds Chemical class 0.000 description 23
239000000243 solution Substances 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 9
239000012948 isocyanate Substances 0.000 description 9
239000000203 mixture Substances 0.000 description 9
FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 9
GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 7
235000013877 carbamide Nutrition 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
150000002513 isocyanates Chemical class 0.000 description 7
230000007306 turnover Effects 0.000 description 7
239000002841 Lewis acid Substances 0.000 description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical class [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 description 6
238000005810 carbonylation reaction Methods 0.000 description 6
150000007517 lewis acids Chemical class 0.000 description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
239000002904 solvent Substances 0.000 description 6
230000006315 carbonylation Effects 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
238000006722 reduction reaction Methods 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
150000001450 anions Chemical class 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
150000002832 nitroso derivatives Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
JBMHZDKOFRNROK-UHFFFAOYSA-N P[Ru]P Chemical compound P[Ru]P JBMHZDKOFRNROK-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007983 Tris buffer Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
150000001555 benzenes Chemical class 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000007423 decrease Effects 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
150000002440 hydroxy compounds Chemical class 0.000 description 3
IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 description 3
VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 3
238000005832 oxidative carbonylation reaction Methods 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
125000004437 phosphorous atom Chemical group 0.000 description 3
239000000047 product Substances 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
150000003303 ruthenium Chemical class 0.000 description 3
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical class CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 description 2
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical group C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000012018 catalyst precursor Substances 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
ZMLAGADERARBEF-UHFFFAOYSA-N dinitromethylcyclohexane Chemical compound [O-][N+](=O)C([N+]([O-])=O)C1CCCCC1 ZMLAGADERARBEF-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
230000006698 induction Effects 0.000 description 2
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical class Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
FJCCWUVWFDOSAU-UHFFFAOYSA-N n-benzylnitramide Chemical compound [O-][N+](=O)NCC1=CC=CC=C1 FJCCWUVWFDOSAU-UHFFFAOYSA-N 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
VOWZNBNDMFLQGM-UHFFFAOYSA-N o-amino-p-xylene Natural products CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical group [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 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
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
DBRIJAFRMPUNTG-UHFFFAOYSA-N (2-chlorophenyl)-phenyldiazene Chemical group ClC1=CC=CC=C1N=NC1=CC=CC=C1 DBRIJAFRMPUNTG-UHFFFAOYSA-N 0.000 description 1
BGTRPWQPOVFGFO-UHFFFAOYSA-N (2-chlorophenyl)imino-oxido-phenylazanium Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1Cl BGTRPWQPOVFGFO-UHFFFAOYSA-N 0.000 description 1
KUXIQKVLTGHSAN-UHFFFAOYSA-N (2-chlorophenyl)phosphane Chemical compound PC1=CC=CC=C1Cl KUXIQKVLTGHSAN-UHFFFAOYSA-N 0.000 description 1
MPBIEBDMFDFWOI-UHFFFAOYSA-N (2-hydroxyphenyl)imino-oxido-phenylazanium Chemical class OC1=CC=CC=C1N=[N+]([O-])C1=CC=CC=C1 MPBIEBDMFDFWOI-UHFFFAOYSA-N 0.000 description 1
RHNSSYGTJAAVCR-UHFFFAOYSA-N (4-methylphenyl)carbamic acid Chemical compound CC1=CC=C(NC(O)=O)C=C1 RHNSSYGTJAAVCR-UHFFFAOYSA-N 0.000 description 1
IYWJIYWFPADQAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;ruthenium Chemical compound [Ru].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O IYWJIYWFPADQAN-LNTINUHCSA-N 0.000 description 1
OWJVEZJJRYZWNI-UHFFFAOYSA-N 1,1-dinitrocyclohexane Chemical compound [O-][N+](=O)C1([N+]([O-])=O)CCCCC1 OWJVEZJJRYZWNI-UHFFFAOYSA-N 0.000 description 1
LKKHEZBRRGJBGH-UHFFFAOYSA-N 1,1-dinitroethane Chemical compound [O-][N+](=O)C(C)[N+]([O-])=O LKKHEZBRRGJBGH-UHFFFAOYSA-N 0.000 description 1
HLUAPIYZVLAARK-UHFFFAOYSA-N 1,1-dinitrohexane Chemical compound CCCCCC([N+]([O-])=O)[N+]([O-])=O HLUAPIYZVLAARK-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-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
XELWURJCOUZILE-UHFFFAOYSA-N 1-bromo-4-(nitromethyl)benzene Chemical compound [O-][N+](=O)CC1=CC=C(Br)C=C1 XELWURJCOUZILE-UHFFFAOYSA-N 0.000 description 1
SRYLRVUJDQTFDL-UHFFFAOYSA-N 1-chloro-2,3,4-trinitrobenzene Chemical class [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1[N+]([O-])=O SRYLRVUJDQTFDL-UHFFFAOYSA-N 0.000 description 1
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
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238000005984 hydrogenation reaction Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
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RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
150000002527 isonitriles Chemical class 0.000 description 1
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239000006193 liquid solution Substances 0.000 description 1
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230000007246 mechanism Effects 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
OKBJVCWRESLMMD-UHFFFAOYSA-N methyl n-(4-methylphenyl)carbamate Chemical compound COC(=O)NC1=CC=C(C)C=C1 OKBJVCWRESLMMD-UHFFFAOYSA-N 0.000 description 1
UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
FZZMDWLROBNSRG-UHFFFAOYSA-N n-phenyliminonitramide Chemical group [O-][N+](=O)N=NC1=CC=CC=C1 FZZMDWLROBNSRG-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000005181 nitrobenzenes Chemical class 0.000 description 1
NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 description 1
CJSZWOGCKKDSJG-UHFFFAOYSA-N nitrocyclopentane Chemical compound [O-][N+](=O)C1CCCC1 CJSZWOGCKKDSJG-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 1
AFLQDEOAJRGCOW-UHFFFAOYSA-N nitrosocyclohexane Chemical compound O=NC1CCCCC1 AFLQDEOAJRGCOW-UHFFFAOYSA-N 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical class COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
125000000913 palmityl group Chemical group [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
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
150000002987 phenanthrenes Chemical class 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000005070 sampling Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
239000000015 trinitrotoluene Substances 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000008096 xylene Substances 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Landscapes

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

CA000575485A 1983-09-16 1988-08-23 Methode de preparation d'urethanes Expired CA1257607A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000575485A CA1257607A (fr)	1983-09-16	1988-08-23	Methode de preparation d'urethanes

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US532,785		1983-09-16
US06/532,784 US4600793A (en)	1983-09-16	1983-09-16	Process for the preparation of urethanes
US532,784		1983-09-16
US06/532,785 US4603216A (en)	1983-09-16	1983-09-16	Process for the preparation of urethanes
CA000463144A CA1244466A (fr)	1983-09-16	1984-09-14	Procede de preparation d'urethannes
CA000575485A CA1257607A (fr)	1983-09-16	1988-08-23	Methode de preparation d'urethanes

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000463144A Division CA1244466A (fr)	1983-09-16	1984-09-14	Procede de preparation d'urethannes

Publications (1)

Publication Number	Publication Date
CA1257607A true CA1257607A (fr)	1989-07-18

Family

ID=27167466

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000575485A Expired CA1257607A (fr)	1983-09-16	1988-08-23	Methode de preparation d'urethanes

Country Status (1)

Country	Link
CA (1)	CA1257607A (fr)

1988
- 1988-08-23 CA CA000575485A patent/CA1257607A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-07-18	MKEX	Expiry

Publication	Publication Date	Title
EP0086281B1 (fr)	1985-05-15	Préparation de carbamates en utilisant un catalysateur qui contient un palladium
CA1153386A (fr)	1983-09-06	Methode de preparation d'urethanes
US3993685A (en)	1976-11-23	Process for the production of urethanes
US4178455A (en)	1979-12-11	Process for preparing aromatic urethanes
US4603216A (en)	1986-07-29	Process for the preparation of urethanes
US4600793A (en)	1986-07-15	Process for the preparation of urethanes
US4705883A (en)	1987-11-10	Carbonylation process
US4629804A (en)	1986-12-16	Process for preparation of urethanes
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