CA1075259A - Nuclear hydrogenation of n-aryl carbamates - Google Patents
Nuclear hydrogenation of n-aryl carbamatesInfo
- Publication number
- CA1075259A CA1075259A CA259,244A CA259244A CA1075259A CA 1075259 A CA1075259 A CA 1075259A CA 259244 A CA259244 A CA 259244A CA 1075259 A CA1075259 A CA 1075259A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- carbamate
- methyl
- dimethyl
- acid
- Prior art date
- 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
Links
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 80
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 9
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 8
- IDMPEWXHBJHVIQ-UHFFFAOYSA-N methyl n-[4-[[4-(methoxycarbonylamino)phenyl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1CC1=CC=C(NC(=O)OC)C=C1 IDMPEWXHBJHVIQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000010948 rhodium Substances 0.000 claims description 32
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 30
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- -1 ethylphenyl Chemical group 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 229910052703 rhodium Inorganic materials 0.000 claims description 18
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 17
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical group COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 claims description 7
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- QHGZFCAIXRVHID-UHFFFAOYSA-N ethyl n-methyl-n-phenylcarbamate Chemical group CCOC(=O)N(C)C1=CC=CC=C1 QHGZFCAIXRVHID-UHFFFAOYSA-N 0.000 claims description 4
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical class CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000010306 acid treatment Methods 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- CEUNIYVZFAQQSI-UHFFFAOYSA-N cyclohexyl n-phenylcarbamate Chemical group C1CCCCC1OC(=O)NC1=CC=CC=C1 CEUNIYVZFAQQSI-UHFFFAOYSA-N 0.000 claims description 3
- BUIPKGZDEMXJLW-UHFFFAOYSA-N methyl n-cyclohexylcarbamate Chemical group COC(=O)NC1CCCCC1 BUIPKGZDEMXJLW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- JEAXEFPTKIJYRO-UHFFFAOYSA-N cyclohexyl n-cyclohexylcarbamate Chemical group C1CCCCC1OC(=O)NC1CCCCC1 JEAXEFPTKIJYRO-UHFFFAOYSA-N 0.000 claims description 2
- OREOMTZWBFHCAH-UHFFFAOYSA-N ethyl n-[4-[[4-[ethoxycarbonyl(methyl)amino]cyclohexyl]methyl]cyclohexyl]-n-methylcarbamate Chemical class C1CC(N(C)C(=O)OCC)CCC1CC1CCC(N(C)C(=O)OCC)CC1 OREOMTZWBFHCAH-UHFFFAOYSA-N 0.000 claims description 2
- CRNKWGWDUOCHTA-UHFFFAOYSA-N ethyl n-cyclohexyl-n-methylcarbamate Chemical group CCOC(=O)N(C)C1CCCCC1 CRNKWGWDUOCHTA-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- DIDUBGFFSUEEGU-UHFFFAOYSA-N methyl n-[5-(methoxycarbonylamino)naphthalen-1-yl]carbamate Chemical group C1=CC=C2C(NC(=O)OC)=CC=CC2=C1NC(=O)OC DIDUBGFFSUEEGU-UHFFFAOYSA-N 0.000 claims description 2
- IZPAJCSXPWFEPU-UHFFFAOYSA-N methyl n-naphthalen-1-ylcarbamate Chemical group C1=CC=C2C(NC(=O)OC)=CC=CC2=C1 IZPAJCSXPWFEPU-UHFFFAOYSA-N 0.000 claims description 2
- ULCFANPHZAXCFJ-UHFFFAOYSA-N propan-2-yl n-[4-[[4-(propan-2-yloxycarbonylamino)phenyl]methyl]phenyl]carbamate Chemical group C1=CC(NC(=O)OC(C)C)=CC=C1CC1=CC=C(NC(=O)OC(C)C)C=C1 ULCFANPHZAXCFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- DFVZZGGYMLDFAU-UHFFFAOYSA-N methyl n-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl)carbamate Chemical class C1CCCC2C(NC(=O)OC)CCCC21 DFVZZGGYMLDFAU-UHFFFAOYSA-N 0.000 claims 1
- POKSHXOHFKADFP-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-phenylmethyl]carbamate Chemical group COC(=O)NC(NC(=O)OC)C1=CC=CC=C1 POKSHXOHFKADFP-UHFFFAOYSA-N 0.000 claims 1
- 125000004957 naphthylene group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract description 59
- 239000004814 polyurethane Substances 0.000 abstract description 4
- 229910052723 transition metal Inorganic materials 0.000 abstract description 2
- 150000003624 transition metals Chemical class 0.000 abstract description 2
- 230000004913 activation Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 229960004592 isopropanol Drugs 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- HGHYGRYUGKKTPL-UHFFFAOYSA-N 4-aminobenzenesulfonic acid;2-aminoethanol Chemical compound NCCO.NC1=CC=C(S(O)(=O)=O)C=C1 HGHYGRYUGKKTPL-UHFFFAOYSA-N 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 208000005374 Poisoning Diseases 0.000 description 5
- 231100000572 poisoning Toxicity 0.000 description 5
- 230000000607 poisoning effect Effects 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 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
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000982822 Ficus obtusifolia Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- GAUSUDNBBOZKSB-UHFFFAOYSA-N methyl(phenyl)carbamic acid Chemical compound OC(=O)N(C)C1=CC=CC=C1 GAUSUDNBBOZKSB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229940022663 acetate Drugs 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CLEDVMVKFGVPHR-UHFFFAOYSA-N (3,4-diethoxyphenyl)carbamic acid Chemical compound CCOC1=CC=C(NC(O)=O)C=C1OCC CLEDVMVKFGVPHR-UHFFFAOYSA-N 0.000 description 1
- HNAXBZUMENBWSX-UHFFFAOYSA-N (3-methylphenyl)carbamic acid Chemical compound CC1=CC=CC(NC(O)=O)=C1 HNAXBZUMENBWSX-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
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
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- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
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- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 101100242191 Tetraodon nigroviridis rho gene Proteins 0.000 description 1
- CCWFPXHGWPJNHP-UHFFFAOYSA-N [2-(carboxyamino)phenyl]carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1NC(O)=O CCWFPXHGWPJNHP-UHFFFAOYSA-N 0.000 description 1
- MFPKKXXZTIGKQZ-UHFFFAOYSA-N [3-(carboxyamino)naphthalen-2-yl]carbamic acid Chemical compound C1=CC=C2C=C(NC(O)=O)C(NC(=O)O)=CC2=C1 MFPKKXXZTIGKQZ-UHFFFAOYSA-N 0.000 description 1
- VVZCCVYHBGFSNH-UHFFFAOYSA-N [4-(carboxyamino)phenyl]carbamic acid Chemical compound OC(=O)NC1=CC=C(NC(O)=O)C=C1 VVZCCVYHBGFSNH-UHFFFAOYSA-N 0.000 description 1
- FMCPCXAFYCEPQL-UHFFFAOYSA-N [4-[[4-(carboxyamino)phenyl]methyl]phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1CC1=CC=C(NC(O)=O)C=C1 FMCPCXAFYCEPQL-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000006227 byproduct Substances 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- NFVCLSROJROZEQ-UHFFFAOYSA-N ethyl 3-(ethoxycarbonylamino)benzoate Chemical compound CCOC(=O)NC1=CC=CC(C(=O)OCC)=C1 NFVCLSROJROZEQ-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- HPMBJEHEKMHVHF-UHFFFAOYSA-N ethyl n-(2-ethoxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC=C1OCC HPMBJEHEKMHVHF-UHFFFAOYSA-N 0.000 description 1
- AXHTZVWDOXONQF-UHFFFAOYSA-N ethyl n-[4-[[4-(ethoxycarbonylamino)phenyl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CC1=CC=C(NC(=O)OCC)C=C1 AXHTZVWDOXONQF-UHFFFAOYSA-N 0.000 description 1
- XEFYPTRGVWLMHB-UHFFFAOYSA-N ethyl n-ethyl-n-phenylcarbamate Chemical compound CCOC(=O)N(CC)C1=CC=CC=C1 XEFYPTRGVWLMHB-UHFFFAOYSA-N 0.000 description 1
- GJAJDMJVIYHOBG-UHFFFAOYSA-N ethyl n-fluoranthen-3-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=CC=C3NC(=O)OCC GJAJDMJVIYHOBG-UHFFFAOYSA-N 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- RTDMTAYLVSRWIO-UHFFFAOYSA-N methyl 2-(methoxycarbonylamino)benzoate Chemical compound COC(=O)NC1=CC=CC=C1C(=O)OC RTDMTAYLVSRWIO-UHFFFAOYSA-N 0.000 description 1
- FMHMUWBJHWFZEC-UHFFFAOYSA-N methyl N-(2-methyl-3-propan-2-ylphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(C(C)C)=C1C FMHMUWBJHWFZEC-UHFFFAOYSA-N 0.000 description 1
- FJBYKALZQYDXDA-UHFFFAOYSA-N methyl n-(2,4,6-trimethylphenyl)carbamate Chemical compound COC(=O)NC1=C(C)C=C(C)C=C1C FJBYKALZQYDXDA-UHFFFAOYSA-N 0.000 description 1
- GDRBZLZLABLCCG-UHFFFAOYSA-N methyl n-(2,4-dimethoxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=C(OC)C=C1OC GDRBZLZLABLCCG-UHFFFAOYSA-N 0.000 description 1
- UYAHMJMKOKLRSI-UHFFFAOYSA-N methyl n-(2-ethylphenyl)carbamate Chemical compound CCC1=CC=CC=C1NC(=O)OC UYAHMJMKOKLRSI-UHFFFAOYSA-N 0.000 description 1
- UWJYJIINQUGOPP-UHFFFAOYSA-N methyl n-(2-methoxy-5-methylphenyl)carbamate Chemical compound COC(=O)NC1=CC(C)=CC=C1OC UWJYJIINQUGOPP-UHFFFAOYSA-N 0.000 description 1
- LXZYLGUNAYNUGX-UHFFFAOYSA-N methyl n-(2-phenylphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC=C1C1=CC=CC=C1 LXZYLGUNAYNUGX-UHFFFAOYSA-N 0.000 description 1
- IEUWSWKKHKIVMA-UHFFFAOYSA-N methyl n-(3,4-diethylphenyl)carbamate Chemical compound CCC1=CC=C(NC(=O)OC)C=C1CC IEUWSWKKHKIVMA-UHFFFAOYSA-N 0.000 description 1
- ZBMRIHHQSDTWFN-UHFFFAOYSA-N methyl n-(3,5-diethylphenyl)carbamate Chemical compound CCC1=CC(CC)=CC(NC(=O)OC)=C1 ZBMRIHHQSDTWFN-UHFFFAOYSA-N 0.000 description 1
- CPQUYZPVLZKDPI-UHFFFAOYSA-N methyl n-(3,5-dimethoxyphenyl)carbamate Chemical compound COC(=O)NC1=CC(OC)=CC(OC)=C1 CPQUYZPVLZKDPI-UHFFFAOYSA-N 0.000 description 1
- PAUQHJVSLMTANL-UHFFFAOYSA-N methyl n-(4-ethoxyphenyl)carbamate Chemical compound CCOC1=CC=C(NC(=O)OC)C=C1 PAUQHJVSLMTANL-UHFFFAOYSA-N 0.000 description 1
- WSQKRXOGNWTUKT-UHFFFAOYSA-N methyl n-(4-methoxy-2-methylphenyl)carbamate Chemical compound COC(=O)NC1=CC=C(OC)C=C1C WSQKRXOGNWTUKT-UHFFFAOYSA-N 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
- YQGLXHXYFGGBQS-UHFFFAOYSA-N methyl n-(4-phenoxyphenyl)carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1OC1=CC=CC=C1 YQGLXHXYFGGBQS-UHFFFAOYSA-N 0.000 description 1
- OCOOTFAEDYPEAQ-UHFFFAOYSA-N methyl n-(4-phenylphenyl)carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C1=CC=CC=C1 OCOOTFAEDYPEAQ-UHFFFAOYSA-N 0.000 description 1
- YUHKTXULCGYWTC-UHFFFAOYSA-N methyl n-(4-propoxyphenyl)carbamate Chemical compound CCCOC1=CC=C(NC(=O)OC)C=C1 YUHKTXULCGYWTC-UHFFFAOYSA-N 0.000 description 1
- ZMDRBGBDXMTPFV-UHFFFAOYSA-N methyl n-(4-propylphenyl)carbamate Chemical compound CCCC1=CC=C(NC(=O)OC)C=C1 ZMDRBGBDXMTPFV-UHFFFAOYSA-N 0.000 description 1
- UTTJRIWRFQLQDV-UHFFFAOYSA-N methyl n-[2,4-bis(methoxycarbonylamino)phenyl]carbamate Chemical compound COC(=O)NC1=CC=C(NC(=O)OC)C(NC(=O)OC)=C1 UTTJRIWRFQLQDV-UHFFFAOYSA-N 0.000 description 1
- JLXTZXSQSXGVTK-UHFFFAOYSA-N methyl n-[2-(methoxycarbonylamino)-4-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=C(C)C=C1NC(=O)OC JLXTZXSQSXGVTK-UHFFFAOYSA-N 0.000 description 1
- ORSWEPBMUWVPIJ-UHFFFAOYSA-N methyl n-[2-(methoxycarbonylamino)-9h-fluoren-3-yl]carbamate Chemical compound C1C2=CC=CC=C2C2=C1C=C(NC(=O)OC)C(NC(=O)OC)=C2 ORSWEPBMUWVPIJ-UHFFFAOYSA-N 0.000 description 1
- YQMCGGFKVSTCKH-UHFFFAOYSA-N methyl n-[3,5-bis(methoxycarbonylamino)-2,4-dimethylphenyl]carbamate Chemical compound COC(=O)NC1=CC(NC(=O)OC)=C(C)C(NC(=O)OC)=C1C YQMCGGFKVSTCKH-UHFFFAOYSA-N 0.000 description 1
- JNNLWOJZIPJIQG-UHFFFAOYSA-N methyl n-[3-(methoxycarbonylamino)-2-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(NC(=O)OC)=C1C JNNLWOJZIPJIQG-UHFFFAOYSA-N 0.000 description 1
- SAXMDHWQDTVWOS-UHFFFAOYSA-N methyl n-[3-[3-(methoxycarbonylamino)phenyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C=2C=C(NC(=O)OC)C=CC=2)=C1 SAXMDHWQDTVWOS-UHFFFAOYSA-N 0.000 description 1
- RZSSZPGALXGUQS-UHFFFAOYSA-N methyl n-[4-(methoxycarbonylamino)-2-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=C(NC(=O)OC)C(C)=C1 RZSSZPGALXGUQS-UHFFFAOYSA-N 0.000 description 1
- VLPBGAPTYGNIII-UHFFFAOYSA-N methyl n-[4-[4-(methoxycarbonylamino)phenyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C1=CC=C(NC(=O)OC)C=C1 VLPBGAPTYGNIII-UHFFFAOYSA-N 0.000 description 1
- YLGBNQBURVBZMA-UHFFFAOYSA-N methyl n-[7-(methoxycarbonylamino)-9h-fluoren-2-yl]carbamate Chemical compound COC(=O)NC1=CC=C2C3=CC=C(NC(=O)OC)C=C3CC2=C1 YLGBNQBURVBZMA-UHFFFAOYSA-N 0.000 description 1
- FGXCSEYMZMCFKZ-UHFFFAOYSA-N methyl n-[8-(methoxycarbonylamino)naphthalen-1-yl]carbamate Chemical compound C1=CC(NC(=O)OC)=C2C(NC(=O)OC)=CC=CC2=C1 FGXCSEYMZMCFKZ-UHFFFAOYSA-N 0.000 description 1
- IWEQFZPJLRBFDY-UHFFFAOYSA-N methyl n-phenanthren-9-ylcarbamate Chemical compound C1=CC=C2C(NC(=O)OC)=CC3=CC=CC=C3C2=C1 IWEQFZPJLRBFDY-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- ZMVMYBGDGJLCHV-UHFFFAOYSA-N n-methyl-4-[[4-(methylamino)phenyl]methyl]aniline Chemical compound C1=CC(NC)=CC=C1CC1=CC=C(NC)C=C1 ZMVMYBGDGJLCHV-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QFMYUDONCYNYOI-UHFFFAOYSA-N octadecyl n-[4-[[4-(octadecoxycarbonylamino)phenyl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCCCCCCCCCCCCCCCCC)=CC=C1CC1=CC=C(NC(=O)OCCCCCCCCCCCCCCCCCC)C=C1 QFMYUDONCYNYOI-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- UBDYYTBUXAZGBN-UHFFFAOYSA-N phenyl 4-(methoxycarbonylamino)benzoate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(=O)OC1=CC=CC=C1 UBDYYTBUXAZGBN-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HTSBDSBMTJWHBS-UHFFFAOYSA-N propan-2-yl n-anthracen-2-ylcarbamate Chemical compound C1=CC=CC2=CC3=CC(NC(=O)OC(C)C)=CC=C3C=C21 HTSBDSBMTJWHBS-UHFFFAOYSA-N 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 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
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/610,359 US4069240A (en) | 1975-09-04 | 1975-09-04 | Nuclear hydrogenation of n-aryl carbamates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1075259A true CA1075259A (en) | 1980-04-08 |
Family
ID=24444700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA259,244A Expired CA1075259A (en) | 1975-09-04 | 1976-08-17 | Nuclear hydrogenation of n-aryl carbamates |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4069240A (Direct) |
| JP (1) | JPS5233653A (Direct) |
| CA (1) | CA1075259A (Direct) |
| DE (1) | DE2639842A1 (Direct) |
| FR (1) | FR2322859A1 (Direct) |
| GB (1) | GB1551832A (Direct) |
| IT (1) | IT1070301B (Direct) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5182296A (en) * | 1989-10-26 | 1993-01-26 | Tanabe Seiyaky Co., Ltd. | Naphthyloxazolidone derivatives |
| DE19529412A1 (de) * | 1995-08-10 | 1997-02-13 | Bayer Ag | Verfahren zur Herstellung emissionsarmer Polyurethan-Form und Verbundkörper sowie deren Verwendung |
| DE10253803A1 (de) * | 2002-11-18 | 2004-05-27 | Degussa Ag | Verfahren zur Herstellung von aliphatischen Isocyanaten aus aromatischen Isocyanaten |
| DE10253802A1 (de) * | 2002-11-18 | 2004-06-03 | Degussa Ag | Verfahren zur Hydrierung von aromatischen Urethanen in Gegenwart eines geträgerten Rutheniumkatalysators |
| CN116768763A (zh) * | 2022-03-07 | 2023-09-19 | 中国科学院过程工程研究所 | 一种脂环族氨基甲酸酯的制备方法及其应用 |
| CN114644576A (zh) * | 2022-04-21 | 2022-06-21 | 中国科学院过程工程研究所 | 一种1,3-环己烷二亚甲基二氨基甲酸酯及其制备方法与应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3511875A (en) * | 1968-04-12 | 1970-05-12 | Du Pont | Herbicidal alkylcarbamoyloxy semicarbazides |
| US3567764A (en) * | 1968-04-12 | 1971-03-02 | Du Pont | Herbicidal alkylcarbamoyloxyphenyl biurets |
| US3600426A (en) * | 1968-09-30 | 1971-08-17 | American Home Prod | 1-aminocyclopentanecarboxylic acid esters |
| CA929942A (en) * | 1968-10-14 | 1973-07-10 | Okano Atsuji | Esters and their production |
| DE1931386A1 (de) * | 1969-06-20 | 1970-12-23 | Basf Ag | N-acylierte Cycloalkylhydroxylamine |
| BE795668A (fr) * | 1972-02-22 | 1973-08-20 | Uniroyal Inc | Hydrogenation nucleaire des n-arylpolyamides |
-
1975
- 1975-09-04 US US05/610,359 patent/US4069240A/en not_active Expired - Lifetime
-
1976
- 1976-08-17 CA CA259,244A patent/CA1075259A/en not_active Expired
- 1976-09-03 IT IT69159/76A patent/IT1070301B/it active
- 1976-09-03 GB GB36565/76A patent/GB1551832A/en not_active Expired
- 1976-09-03 JP JP51105077A patent/JPS5233653A/ja active Pending
- 1976-09-03 FR FR7626711A patent/FR2322859A1/fr active Granted
- 1976-09-03 DE DE19762639842 patent/DE2639842A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| GB1551832A (en) | 1979-09-05 |
| FR2322859A1 (fr) | 1977-04-01 |
| FR2322859B1 (Direct) | 1982-02-19 |
| US4069240A (en) | 1978-01-17 |
| IT1070301B (it) | 1985-03-29 |
| DE2639842A1 (de) | 1977-03-17 |
| JPS5233653A (en) | 1977-03-14 |
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