DE3215591A1 - Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureestern - Google Patents
Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureesternInfo
- Publication number
- DE3215591A1 DE3215591A1 DE19823215591 DE3215591A DE3215591A1 DE 3215591 A1 DE3215591 A1 DE 3215591A1 DE 19823215591 DE19823215591 DE 19823215591 DE 3215591 A DE3215591 A DE 3215591A DE 3215591 A1 DE3215591 A1 DE 3215591A1
- Authority
- DE
- Germany
- Prior art keywords
- cleavage
- carbamic acid
- reactor
- acid esters
- products
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 70
- 150000002148 esters Chemical class 0.000 title description 6
- 239000002253 acid Substances 0.000 title description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 128
- 230000007017 scission Effects 0.000 claims description 127
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 85
- 239000000047 product Substances 0.000 claims description 69
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 49
- 239000012948 isocyanate Substances 0.000 claims description 47
- 150000002513 isocyanates Chemical class 0.000 claims description 47
- 238000009835 boiling Methods 0.000 claims description 36
- 239000007788 liquid Substances 0.000 claims description 26
- 239000010409 thin film Substances 0.000 claims description 25
- 239000006227 byproduct Substances 0.000 claims description 23
- 230000004992 fission Effects 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 238000000926 separation method Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 210000002196 fr. b Anatomy 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 210000003918 fraction a Anatomy 0.000 claims description 5
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 4
- 239000012159 carrier gas Substances 0.000 claims description 3
- 239000011552 falling film Substances 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- 238000004227 thermal cracking Methods 0.000 claims description 3
- 235000021190 leftovers Nutrition 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 23
- -1 biurets Chemical class 0.000 description 20
- 150000002440 hydroxy compounds Chemical class 0.000 description 18
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- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 16
- 239000007858 starting material Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000007789 gas Substances 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- FJSKBPJWQNFYKM-UHFFFAOYSA-N octadecyl n-methylcarbamate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)NC FJSKBPJWQNFYKM-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
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- 239000010408 film Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- PHYURWGMBQTCSY-UHFFFAOYSA-N ethyl n-[3-(ethoxycarbonylamino)-4-methylphenyl]carbamate Chemical compound CCOC(=O)NC1=CC=C(C)C(NC(=O)OCC)=C1 PHYURWGMBQTCSY-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 3
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-Methoxynaphthalene Natural products C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- UGOUHVOPAACNLX-UHFFFAOYSA-N ethyl n-benzhydrylcarbamate Chemical compound C=1C=CC=CC=1C(NC(=O)OCC)C1=CC=CC=C1 UGOUHVOPAACNLX-UHFFFAOYSA-N 0.000 description 2
- ROEBHPYGKGTXKM-UHFFFAOYSA-N ethyl n-isocyanatocarbamate Chemical class CCOC(=O)NN=C=O ROEBHPYGKGTXKM-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 238000001149 thermolysis Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- BDTKKFKBPMKUEO-UHFFFAOYSA-N (2,4-dimethylphenyl) N-ethylcarbamate Chemical compound CCNC(=O)OC1=CC=C(C)C=C1C BDTKKFKBPMKUEO-UHFFFAOYSA-N 0.000 description 1
- AJKHRGMQGRFMAQ-UHFFFAOYSA-N (2-nonylphenyl) N-butylcarbamate Chemical compound C(CCCCCCCC)C1=C(C=CC=C1)OC(NCCCC)=O AJKHRGMQGRFMAQ-UHFFFAOYSA-N 0.000 description 1
- IRDYVYXLTFZDBL-UHFFFAOYSA-N (4-chlorophenyl)methyl n-methylcarbamate Chemical compound CNC(=O)OCC1=CC=C(Cl)C=C1 IRDYVYXLTFZDBL-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-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
- DTCBAFFIVLPZJC-UHFFFAOYSA-N 1-benzyl-2,3-dichloronaphthalene Chemical compound ClC=1C(Cl)=CC2=CC=CC=C2C=1CC1=CC=CC=C1 DTCBAFFIVLPZJC-UHFFFAOYSA-N 0.000 description 1
- KTHUKEZOIFYPEH-UHFFFAOYSA-N 1-benzylnaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 KTHUKEZOIFYPEH-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- FYLPTUZLJAZQDR-UHFFFAOYSA-N 1-pentoxynaphthalene Chemical compound C1=CC=C2C(OCCCCC)=CC=CC2=C1 FYLPTUZLJAZQDR-UHFFFAOYSA-N 0.000 description 1
- PUNPBZOTYNFMSU-UHFFFAOYSA-N 10-(methylcarbamoyloxy)decyl n-methylcarbamate Chemical compound CNC(=O)OCCCCCCCCCCOC(=O)NC PUNPBZOTYNFMSU-UHFFFAOYSA-N 0.000 description 1
- MYXAEQOILSSYKG-UHFFFAOYSA-N 12-(benzylcarbamoyloxy)octadecyl n-benzylcarbamate Chemical compound C=1C=CC=CC=1CNC(=O)OC(CCCCCC)CCCCCCCCCCCOC(=O)NCC1=CC=CC=C1 MYXAEQOILSSYKG-UHFFFAOYSA-N 0.000 description 1
- PPAXTRUEIXSJIG-UHFFFAOYSA-N 12-(butylcarbamoyloxy)dodecyl n-butylcarbamate Chemical compound CCCCNC(=O)OCCCCCCCCCCCCOC(=O)NCCCC PPAXTRUEIXSJIG-UHFFFAOYSA-N 0.000 description 1
- NDFDMFUPIJVFQM-UHFFFAOYSA-N 12-(methylcarbamoyloxy)dodecyl n-methylcarbamate Chemical compound CNC(=O)OCCCCCCCCCCCCOC(=O)NC NDFDMFUPIJVFQM-UHFFFAOYSA-N 0.000 description 1
- DNCOWQMQNMELRK-UHFFFAOYSA-N 12-(phenylcarbamoyloxy)dodecyl n-phenylcarbamate Chemical compound C=1C=CC=CC=1NC(=O)OCCCCCCCCCCCCOC(=O)NC1=CC=CC=C1 DNCOWQMQNMELRK-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- WSXZZSOCWHLSAC-UHFFFAOYSA-N 2-benzyl-1-chloronaphthalene Chemical compound C1=CC2=CC=CC=C2C(Cl)=C1CC1=CC=CC=C1 WSXZZSOCWHLSAC-UHFFFAOYSA-N 0.000 description 1
- FXPSNOVRPHPNFC-UHFFFAOYSA-N 2-methyl-5-(4-methyl-3-nitrophenyl)-1,3,4-oxadiazole Chemical compound O1C(C)=NN=C1C1=CC=C(C)C([N+]([O-])=O)=C1 FXPSNOVRPHPNFC-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- XWYAEJCEJFWSNX-UHFFFAOYSA-N 2-phenoxyethyl n-methylcarbamate Chemical compound CNC(=O)OCCOC1=CC=CC=C1 XWYAEJCEJFWSNX-UHFFFAOYSA-N 0.000 description 1
- CYQZQOJTZOFPFT-UHFFFAOYSA-N 4,6-bis(methylcarbamoyloxy)hexyl n-methylcarbamate Chemical compound CNC(=O)OCCCC(OC(=O)NC)CCOC(=O)NC CYQZQOJTZOFPFT-UHFFFAOYSA-N 0.000 description 1
- WUFUXMGNTYCDTQ-UHFFFAOYSA-N 6-(ethylcarbamoyloxy)hexyl n-ethylcarbamate Chemical compound CCNC(=O)OCCCCCCOC(=O)NCC WUFUXMGNTYCDTQ-UHFFFAOYSA-N 0.000 description 1
- HFIQSRRUOREJMX-UHFFFAOYSA-N 6-(methoxymethylcarbamoyloxy)hexyl n-(methoxymethyl)carbamate Chemical compound COCNC(=O)OCCCCCCOC(=O)NCOC HFIQSRRUOREJMX-UHFFFAOYSA-N 0.000 description 1
- PZIJBXUWDCJCHG-UHFFFAOYSA-N 6-(methylcarbamoyloxy)hexyl n-methylcarbamate Chemical compound CNC(=O)OCCCCCCOC(=O)NC PZIJBXUWDCJCHG-UHFFFAOYSA-N 0.000 description 1
- PLMFCYXLBGFZCO-UHFFFAOYSA-N 8-(propylcarbamoyloxy)octyl n-propylcarbamate Chemical compound CCCNC(=O)OCCCCCCCCOC(=O)NCCC PLMFCYXLBGFZCO-UHFFFAOYSA-N 0.000 description 1
- QESOAYJZURVXLG-UHFFFAOYSA-N CC(CC)OCCNC(=O)OCCCCCCCCCCCCCCCCCCOC(NCCOC(C)CC)=O Chemical compound CC(CC)OCCNC(=O)OCCCCCCCCCCCCCCCCCCOC(NCCOC(C)CC)=O QESOAYJZURVXLG-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
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- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- QFXMTBBPSHXHTM-UHFFFAOYSA-N [3-(methylcarbamoyloxy)phenyl] n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC(OC(=O)NC)=C1 QFXMTBBPSHXHTM-UHFFFAOYSA-N 0.000 description 1
- POTKYRMKSWIKQM-UHFFFAOYSA-N [4-(methylcarbamoyloxy)cyclohexyl] n-methylcarbamate Chemical compound CNC(=O)OC1CCC(OC(=O)NC)CC1 POTKYRMKSWIKQM-UHFFFAOYSA-N 0.000 description 1
- OEPQPNJDIZBKOG-UHFFFAOYSA-N [4-[2-[4-(butylcarbamoyloxy)cyclohexyl]propan-2-yl]cyclohexyl] n-butylcarbamate Chemical compound C1CC(OC(=O)NCCCC)CCC1C(C)(C)C1CCC(OC(=O)NCCCC)CC1 OEPQPNJDIZBKOG-UHFFFAOYSA-N 0.000 description 1
- JREYJFYXRYZXBQ-UHFFFAOYSA-N [4-[2-[4-(methylcarbamoyloxy)cyclohexyl]propan-2-yl]cyclohexyl] n-methylcarbamate Chemical compound C1CC(OC(=O)NC)CCC1C(C)(C)C1CCC(OC(=O)NC)CC1 JREYJFYXRYZXBQ-UHFFFAOYSA-N 0.000 description 1
- CCIJOEYMAYCMSA-UHFFFAOYSA-N [4-[4-(ethylcarbamoyloxy)phenyl]phenyl] n-ethylcarbamate Chemical group C1=CC(OC(=O)NCC)=CC=C1C1=CC=C(OC(=O)NCC)C=C1 CCIJOEYMAYCMSA-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- QMDPEBMTDBSGAE-UHFFFAOYSA-N benzyl n-methylcarbamate Chemical compound CNC(=O)OCC1=CC=CC=C1 QMDPEBMTDBSGAE-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
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- 239000001273 butane Substances 0.000 description 1
- SYAGECNPOQGRIW-UHFFFAOYSA-N butyl n-(3,4-dichlorophenyl)carbamate Chemical compound CCCCOC(=O)NC1=CC=C(Cl)C(Cl)=C1 SYAGECNPOQGRIW-UHFFFAOYSA-N 0.000 description 1
- DUAXEFJRDGQLLU-UHFFFAOYSA-N butyl n-[3-[(butoxycarbonylamino)methyl]-3,5,5-trimethylcyclohexyl]carbamate Chemical compound CCCCOC(=O)NCC1(C)CC(NC(=O)OCCCC)CC(C)(C)C1 DUAXEFJRDGQLLU-UHFFFAOYSA-N 0.000 description 1
- KQNRUVYUHYRKGR-UHFFFAOYSA-N butyl n-[5-(butoxycarbonylamino)naphthalen-1-yl]carbamate Chemical compound C1=CC=C2C(NC(=O)OCCCC)=CC=CC2=C1NC(=O)OCCCC KQNRUVYUHYRKGR-UHFFFAOYSA-N 0.000 description 1
- KYXRWOMOJKXLCB-UHFFFAOYSA-N butyl n-octadecylcarbamate Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)OCCCC KYXRWOMOJKXLCB-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- BJZJDEOGMBZSLE-UHFFFAOYSA-N cyclohexane;hydrate Chemical compound O.C1CCCCC1 BJZJDEOGMBZSLE-UHFFFAOYSA-N 0.000 description 1
- BLRPNQVHNBMFSB-UHFFFAOYSA-N cyclohexyl n-[2-(cyclohexyloxycarbonylamino)ethyl]carbamate Chemical compound C1CCCCC1OC(=O)NCCNC(=O)OC1CCCCC1 BLRPNQVHNBMFSB-UHFFFAOYSA-N 0.000 description 1
- OQQXGCLLMDQESN-UHFFFAOYSA-N cyclohexylcarbamic acid Chemical compound OC(=O)NC1CCCCC1 OQQXGCLLMDQESN-UHFFFAOYSA-N 0.000 description 1
- BGILCZPKYGSHNZ-UHFFFAOYSA-N decyl n-methylcarbamate Chemical compound CCCCCCCCCCOC(=O)NC BGILCZPKYGSHNZ-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- 125000006840 diphenylmethane group Chemical class 0.000 description 1
- CCBWNJSNJXVPRT-UHFFFAOYSA-N dodecyl N-(methoxymethyl)carbamate Chemical compound C(CCCCCCCCCCC)OC(NCOC)=O CCBWNJSNJXVPRT-UHFFFAOYSA-N 0.000 description 1
- NFGVFPZQHKGFIM-UHFFFAOYSA-N dodecyl n-(2-methoxyethyl)carbamate Chemical compound CCCCCCCCCCCCOC(=O)NCCOC NFGVFPZQHKGFIM-UHFFFAOYSA-N 0.000 description 1
- KAMQYCQIVWNZRB-UHFFFAOYSA-N dodecyl n-methylcarbamate Chemical compound CCCCCCCCCCCCOC(=O)NC KAMQYCQIVWNZRB-UHFFFAOYSA-N 0.000 description 1
- UATVIVWPWXCCFM-UHFFFAOYSA-N dodecyl n-phenylcarbamate Chemical compound CCCCCCCCCCCCOC(=O)NC1=CC=CC=C1 UATVIVWPWXCCFM-UHFFFAOYSA-N 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002031 ethanolic fraction Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- PIWMEDXPFQNSPH-UHFFFAOYSA-N ethyl N-(2-methylhex-1-enyl)carbamate Chemical compound C(C)OC(NC=C(CCCC)C)=O PIWMEDXPFQNSPH-UHFFFAOYSA-N 0.000 description 1
- WXDDBYFBIIAYSM-UHFFFAOYSA-N ethyl n-(2-phenylethyl)carbamate Chemical compound CCOC(=O)NCCC1=CC=CC=C1 WXDDBYFBIIAYSM-UHFFFAOYSA-N 0.000 description 1
- YOBPHLMTNCMNPN-UHFFFAOYSA-N ethyl n-(3-isocyanato-2-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(N=C=O)=C1C YOBPHLMTNCMNPN-UHFFFAOYSA-N 0.000 description 1
- XYSNXNHHBUFLLV-UHFFFAOYSA-N ethyl n-(3-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(C)=C1 XYSNXNHHBUFLLV-UHFFFAOYSA-N 0.000 description 1
- WSKXXIMERYQVGJ-UHFFFAOYSA-N ethyl n-(4-chlorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Cl)C=C1 WSKXXIMERYQVGJ-UHFFFAOYSA-N 0.000 description 1
- FCEQQAOTQZQRTE-UHFFFAOYSA-N ethyl n-(4-cyclohexylphenyl)carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C1CCCCC1 FCEQQAOTQZQRTE-UHFFFAOYSA-N 0.000 description 1
- ITRLUMWQVMULBJ-UHFFFAOYSA-N ethyl n-(5-isocyanato-2-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC(N=C=O)=CC=C1C ITRLUMWQVMULBJ-UHFFFAOYSA-N 0.000 description 1
- QNJPOHYCQROUCT-UHFFFAOYSA-N ethyl n-[3-(ethoxycarbonylamino)-2-methylphenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(NC(=O)OCC)=C1C QNJPOHYCQROUCT-UHFFFAOYSA-N 0.000 description 1
- FNCONBBYGBPHQA-UHFFFAOYSA-N ethyl n-[3-(ethoxycarbonylamino)phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(NC(=O)OCC)=C1 FNCONBBYGBPHQA-UHFFFAOYSA-N 0.000 description 1
- BHIJTTOVTIAITI-UHFFFAOYSA-N ethyl n-[4-(ethoxycarbonylamino)butyl]carbamate Chemical compound CCOC(=O)NCCCCNC(=O)OCC BHIJTTOVTIAITI-UHFFFAOYSA-N 0.000 description 1
- OLKNJKCNIMETAL-UHFFFAOYSA-N ethyl n-[4-(ethoxycarbonylamino)cyclohexyl]carbamate Chemical compound CCOC(=O)NC1CCC(NC(=O)OCC)CC1 OLKNJKCNIMETAL-UHFFFAOYSA-N 0.000 description 1
- FWKGEANWQNXYRM-UHFFFAOYSA-N ethyl n-[6-(ethoxycarbonylamino)hexyl]carbamate Chemical compound CCOC(=O)NCCCCCCNC(=O)OCC FWKGEANWQNXYRM-UHFFFAOYSA-N 0.000 description 1
- RHQYEKYNOVFDQZ-UHFFFAOYSA-N ethyl n-[[3-[(ethoxycarbonylamino)methyl]phenyl]methyl]carbamate Chemical compound CCOC(=O)NCC1=CC=CC(CNC(=O)OCC)=C1 RHQYEKYNOVFDQZ-UHFFFAOYSA-N 0.000 description 1
- XSXLCQLOFRENHC-UHFFFAOYSA-N ethyl n-benzylcarbamate Chemical compound CCOC(=O)NCC1=CC=CC=C1 XSXLCQLOFRENHC-UHFFFAOYSA-N 0.000 description 1
- ZAVUHLXZFYNAMG-UHFFFAOYSA-N ethyl n-cyclohexylcarbamate Chemical compound CCOC(=O)NC1CCCCC1 ZAVUHLXZFYNAMG-UHFFFAOYSA-N 0.000 description 1
- VGEWEGHHYWGXGG-UHFFFAOYSA-N ethyl n-hydroxycarbamate Chemical class CCOC(=O)NO VGEWEGHHYWGXGG-UHFFFAOYSA-N 0.000 description 1
- LVSUICGYPNGBJM-UHFFFAOYSA-N ethyl n-octylcarbamate Chemical compound CCCCCCCCNC(=O)OCC LVSUICGYPNGBJM-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- ATSBYHRDASJHSQ-UHFFFAOYSA-N methyl 4-(ethoxycarbonylamino)benzoate Chemical compound CCOC(=O)NC1=CC=C(C(=O)OC)C=C1 ATSBYHRDASJHSQ-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- OXNAJPQXTZANJL-UHFFFAOYSA-N methyl n-hexylcarbamate Chemical compound CCCCCCNC(=O)OC OXNAJPQXTZANJL-UHFFFAOYSA-N 0.000 description 1
- IZPAJCSXPWFEPU-UHFFFAOYSA-N methyl n-naphthalen-1-ylcarbamate Chemical compound C1=CC=C2C(NC(=O)OC)=CC=CC2=C1 IZPAJCSXPWFEPU-UHFFFAOYSA-N 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- UIUZMXMCPTYPPC-UHFFFAOYSA-N octadecyl n-butylcarbamate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)NCCCC UIUZMXMCPTYPPC-UHFFFAOYSA-N 0.000 description 1
- TWHAUMDDDFZKHN-UHFFFAOYSA-N octadecyl n-cyclohexylcarbamate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)NC1CCCCC1 TWHAUMDDDFZKHN-UHFFFAOYSA-N 0.000 description 1
- JTVZZMAFUOSLQC-UHFFFAOYSA-N octadecyl n-ethylcarbamate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)NCC JTVZZMAFUOSLQC-UHFFFAOYSA-N 0.000 description 1
- BAQUTPOTCQVDHK-UHFFFAOYSA-N octadecyl n-phenylcarbamate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)NC1=CC=CC=C1 BAQUTPOTCQVDHK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- BIHIRIAQHWRDJF-UHFFFAOYSA-N octyl n-ethylcarbamate Chemical compound CCCCCCCCOC(=O)NCC BIHIRIAQHWRDJF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QMGJOSCGLLVTDH-UHFFFAOYSA-N phenyl n-[8-(phenoxycarbonylamino)-4-[(phenoxycarbonylamino)methyl]octyl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NCCCCC(CNC(=O)OC=1C=CC=CC=1)CCCNC(=O)OC1=CC=CC=C1 QMGJOSCGLLVTDH-UHFFFAOYSA-N 0.000 description 1
- SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical class CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 1
- XXSHSIWRWDZAKE-UHFFFAOYSA-N phenyl n-octadecylcarbamate Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)OC1=CC=CC=C1 XXSHSIWRWDZAKE-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- PWEDNSXDQDXPFT-UHFFFAOYSA-N prop-2-enylcarbamic acid Chemical compound OC(=O)NCC=C PWEDNSXDQDXPFT-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QDZXCXBFZLLQFT-UHFFFAOYSA-N propyl n-phenylcarbamate Chemical compound CCCOC(=O)NC1=CC=CC=C1 QDZXCXBFZLLQFT-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/04—Preparation of derivatives of isocyanic acid from or via carbamates or carbamoyl halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823215591 DE3215591A1 (de) | 1982-04-27 | 1982-04-27 | Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureestern |
| CA000425476A CA1216588A (en) | 1982-04-27 | 1983-04-08 | Continuous process for thermal splitting of carbamic acid esters |
| EP83103587A EP0092738B1 (de) | 1982-04-27 | 1983-04-14 | Verfahren zur kontinuierlichen thermischen Spaltung von Carbamidsäureestern |
| DE8383103587T DE3360430D1 (en) | 1982-04-27 | 1983-04-14 | Process for the continuous thermal decomposition of carbamic-acid esters |
| US06/485,347 US4692550A (en) | 1982-04-27 | 1983-04-15 | Continuous process for thermal splitting of carbamic acid esters |
| JP58071569A JPS58194849A (ja) | 1982-04-27 | 1983-04-25 | カルバミン酸エステルの連続的熱分解法 |
| BR8302136A BR8302136A (pt) | 1982-04-27 | 1983-04-26 | Processo para a dissociacao termica continua de esteres de acido carbamico |
| ES521887A ES8402260A1 (es) | 1982-04-27 | 1983-04-27 | Procedimiento continuo para la disociacion de esteres de acido carbamico. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823215591 DE3215591A1 (de) | 1982-04-27 | 1982-04-27 | Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3215591A1 true DE3215591A1 (de) | 1983-10-27 |
Family
ID=6162030
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823215591 Withdrawn DE3215591A1 (de) | 1982-04-27 | 1982-04-27 | Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureestern |
| DE8383103587T Expired DE3360430D1 (en) | 1982-04-27 | 1983-04-14 | Process for the continuous thermal decomposition of carbamic-acid esters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383103587T Expired DE3360430D1 (en) | 1982-04-27 | 1983-04-14 | Process for the continuous thermal decomposition of carbamic-acid esters |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4692550A (forum.php) |
| EP (1) | EP0092738B1 (forum.php) |
| JP (1) | JPS58194849A (forum.php) |
| BR (1) | BR8302136A (forum.php) |
| CA (1) | CA1216588A (forum.php) |
| DE (2) | DE3215591A1 (forum.php) |
| ES (1) | ES8402260A1 (forum.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009045849A1 (de) * | 2009-10-20 | 2011-04-21 | Technische Universität Bergakademie Freiberg | Verfahren zur Herstellung von Oligo- und Polysiloxanen |
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|---|---|---|---|---|
| IT1183332B (it) * | 1985-02-08 | 1987-10-22 | Enichem Sintesi | Procedimento per la produzione di n-metilcarbammati |
| US4873365A (en) * | 1986-04-04 | 1989-10-10 | American Cyanamid Company | Process for the preparation of isophorone diisocyanate from isophorone dicarbamyl esters using highly selective SnO2 or CuO catalysts |
| EP0271679A3 (en) * | 1986-11-03 | 1988-11-23 | American Cyanamid Company | Isocyanates derived from dienes and process and their preparation |
| JP2538222B2 (ja) * | 1986-12-26 | 1996-09-25 | ダイセル化学工業株式会社 | イソホロンジイソシアネ−トの製造方法 |
| DE3915181A1 (de) * | 1989-05-10 | 1990-11-15 | Bayer Ag | Verfahren zur herstellung von polyisocyanaten |
| IT1244476B (it) * | 1990-12-21 | 1994-07-15 | Enichem Sintesi | Procedimento continuo per la preparazione di isociamati |
| DE4124671A1 (de) * | 1991-07-25 | 1993-01-28 | Basf Ag | Reaktor und verfahren zur thermischen spaltung von carbamidsaeureestern |
| DE4141402A1 (de) * | 1991-12-16 | 1993-06-17 | Bayer Ag | Verfahren zur herstellung von hochreinen aromatischen di- und/oder polyurethanen |
| DE4213099A1 (de) * | 1992-04-21 | 1993-10-28 | Basf Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von organischen Polyisocyanaten |
| DE4231417A1 (de) * | 1992-05-05 | 1993-11-11 | Huels Chemische Werke Ag | Kontinuierliches mehrstufiges Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten |
| US5491256A (en) * | 1992-11-16 | 1996-02-13 | Texaco Inc. | Composition of matter for aliphatic-aromatic ureas, biurets, and allophanates as nitric oxide reducing agents in diesel emissions |
| DK169700B1 (da) * | 1993-02-12 | 1995-01-16 | Topsoe Haldor As | Fremgangsmåde til fremstilling af organiske isocyanater |
| DE4342426A1 (de) * | 1993-12-13 | 1995-06-14 | Bayer Ag | Verfahren zur Herstellung von Diurethanen und ihre Verwendung zur Herstellung von Diisocyanaten |
| DE59705127D1 (de) * | 1996-03-15 | 2001-12-06 | Bayer Ag | Verwendung von hochsiedenden Lösemitteln bzw. -gemischen als Wärmetauschmedium für die thermische Spaltung von Carbamidsäureestern |
| US6160143A (en) * | 2000-02-18 | 2000-12-12 | Artisan Industries Inc. | Method for the concentration and separation of sterols |
| KR100670885B1 (ko) * | 2000-02-29 | 2007-01-18 | 헌트스만 인터내셔날, 엘엘씨 | 유기 폴리이소시아네이트의 제조 방법 |
| DE10209095A1 (de) | 2002-03-01 | 2003-09-11 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| DE10215778A1 (de) | 2002-04-10 | 2003-12-18 | Basf Ag | Reaktor zur thermischen Spaltung von mono- und polyfunktionellen Carbamidsäureestern |
| DE10338509A1 (de) * | 2003-08-22 | 2005-03-17 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE10338511A1 (de) * | 2003-08-22 | 2005-03-17 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE10338508A1 (de) | 2003-08-22 | 2005-03-17 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE102004022626A1 (de) | 2004-05-07 | 2005-12-15 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE102004026451A1 (de) * | 2004-05-29 | 2005-12-15 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| DE102004036499A1 (de) * | 2004-07-28 | 2006-03-23 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
| ATE495149T1 (de) * | 2006-11-17 | 2011-01-15 | Asahi Kasei Chemicals Corp | Verfahren zur herstellung von isocyanaten |
| DE102006057118A1 (de) * | 2006-12-04 | 2008-06-05 | Wacker Chemie Ag | Verfahren zur Herstellung von Isocyanatoorganosilanen |
| TW200844080A (en) | 2007-01-11 | 2008-11-16 | Asahi Kasei Chemicals Corp | Process for producing isocyanate |
| EP2147909B1 (en) * | 2007-03-30 | 2016-12-14 | Asahi Kasei Kabushiki Kaisha | Method for production of isocyanate using composition comprising carbamic acid ester and aromatic hydroxy compound, and composition for transport or storage of carbamic acid ester |
| JP5313164B2 (ja) | 2007-11-19 | 2013-10-09 | 旭化成ケミカルズ株式会社 | イソシアネートおよび芳香族ヒドロキシ化合物の製造方法 |
| RU2483058C2 (ru) | 2008-05-15 | 2013-05-27 | Асахи Касеи Кемикалз Корпорейшн | Способ получения изоцианата |
| BRPI0822695B1 (pt) | 2008-05-15 | 2017-05-02 | Asahi Kasei Chemicals Corp | processo para produzir um isocianato |
| ES2623463T3 (es) | 2009-08-21 | 2017-07-11 | Asahi Kasei Kabushiki Kaisha | Procedimiento para producir un éster del ácido carbámico N sustituido, procedimiento para producir isocianato utilizando éster del ácido carbámico N sustituido y composición para transferir y almacenar éster del ácido carbámico N sustituido que contiene un éster del ácido carbámico N sustituido y compuesto hidroxilado aromático |
| BR112012013061A2 (pt) | 2009-12-01 | 2016-11-22 | Basf Se | processo para preparar isocianatos. |
| BR112012013069B1 (pt) | 2009-12-04 | 2018-05-22 | Basf Se | Processo para preparar isocianatos aromáticos. |
| US8680323B2 (en) | 2010-01-19 | 2014-03-25 | Basf Se | Process for preparing isocyanates by thermal dissociation of carbamates |
| EP2526085B1 (de) * | 2010-01-19 | 2015-08-12 | Basf Se | Verfahren zur herstellung von isocyanaten durch thermische spaltung von carbamaten |
| EP2585433A1 (de) | 2010-06-22 | 2013-05-01 | Basf Se | Heterogen katalysierte carbamatspaltung zur synthese von isocyanaten an festen lewis-säuren |
| KR101489100B1 (ko) | 2010-10-04 | 2015-02-02 | 아사히 가세이 케미칼즈 가부시키가이샤 | 분리 방법 및 이소시아네이트의 제조 방법 |
| ES2726527T3 (es) | 2011-02-21 | 2019-10-07 | Asahi Chemical Ind | Procedimiento para producir compuestos carbonilo |
| WO2016156188A1 (de) | 2015-03-31 | 2016-10-06 | Basf Se | Verfahren zur herstellung von isocyanaten durch carbamatspaltung |
| CN109503648B (zh) * | 2017-09-15 | 2024-05-28 | 张家港市国泰华荣化工新材料有限公司 | 制备3-异氰酸酯基丙基三甲氧基硅烷的装置 |
| JP2019199427A (ja) * | 2018-05-15 | 2019-11-21 | 旭化成株式会社 | イソシアネートの製造方法 |
| JP2019199428A (ja) * | 2018-05-15 | 2019-11-21 | 旭化成株式会社 | イソシアネートの製造方法 |
| JP2019199430A (ja) * | 2018-05-15 | 2019-11-21 | 旭化成株式会社 | イソシアネートの製造方法 |
| JP2019199429A (ja) * | 2018-05-15 | 2019-11-21 | 旭化成株式会社 | イソシアネートの製造方法 |
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| US2713591A (en) * | 1955-07-19 | boc boctanaib | ||
| US2409712A (en) * | 1944-02-03 | 1946-10-22 | Du Pont | Chemical process and products |
| US2692275A (en) * | 1953-01-23 | 1954-10-19 | Rohm & Haas | Preparation of 1, 8-diisocyanato-p-menthane |
| GB763635A (forum.php) * | 1953-04-10 | |||
| US3734941A (en) * | 1968-09-06 | 1973-05-22 | American Cyanamid Co | Process for converting urethanes to isocyanates |
| US3870739A (en) * | 1973-03-05 | 1975-03-11 | Air Prod & Chem | Isocyanates from urethanes |
| US3962302A (en) * | 1974-03-08 | 1976-06-08 | Atlantic Richfield Company | Production of isocyanates from esters of carbamic acids (urethanes) |
| US3919278A (en) * | 1974-06-13 | 1975-11-11 | Atlantic Richfield Co | Production of isocyanates from lower alkyl esters of mononuclear aromatic carbamic acids |
| US3919279A (en) * | 1974-06-26 | 1975-11-11 | Atlantic Richfield Co | Catalytic production of isocyanates from esters of carbamic acids |
| US3919280A (en) * | 1974-07-05 | 1975-11-11 | Atlantic Richfield Co | Recovery of solvents employed in the production of isocyanates from esters of carbamic acids |
| JPS5219624A (en) * | 1975-08-07 | 1977-02-15 | Mitsui Toatsu Chem Inc | Process for preparation of isocyanates |
| JPS5439002A (en) * | 1977-08-30 | 1979-03-24 | Mitsubishi Chem Ind Ltd | Preparation of isocyanates |
| JPS5488222A (en) * | 1977-12-20 | 1979-07-13 | Mitsubishi Chem Ind Ltd | Preparation of isocyanate from carbamate |
| JPS6052693B2 (ja) * | 1977-12-22 | 1985-11-20 | 三菱化学株式会社 | カルバミン酸エステルからのイソシアネ−トの製造法 |
| US4294774A (en) * | 1980-11-14 | 1981-10-13 | The Dow Chemical Company | Preparation of organic isocyanates |
| DE3047898A1 (de) * | 1980-12-19 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureestern und die verwendung von hierbei anfallenden isocyanate und carbamidsaeureester aufweisenden gemischen zur herstellung von isocyanaten |
-
1982
- 1982-04-27 DE DE19823215591 patent/DE3215591A1/de not_active Withdrawn
-
1983
- 1983-04-08 CA CA000425476A patent/CA1216588A/en not_active Expired
- 1983-04-14 EP EP83103587A patent/EP0092738B1/de not_active Expired
- 1983-04-14 DE DE8383103587T patent/DE3360430D1/de not_active Expired
- 1983-04-15 US US06/485,347 patent/US4692550A/en not_active Expired - Fee Related
- 1983-04-25 JP JP58071569A patent/JPS58194849A/ja active Granted
- 1983-04-26 BR BR8302136A patent/BR8302136A/pt not_active IP Right Cessation
- 1983-04-27 ES ES521887A patent/ES8402260A1/es not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009045849A1 (de) * | 2009-10-20 | 2011-04-21 | Technische Universität Bergakademie Freiberg | Verfahren zur Herstellung von Oligo- und Polysiloxanen |
| DE102009045849B4 (de) | 2009-10-20 | 2018-03-08 | Technische Universität Bergakademie Freiberg | Verfahren zur Herstellung von Oligo- und Polysiloxanen |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1216588A (en) | 1987-01-13 |
| BR8302136A (pt) | 1983-12-27 |
| JPS58194849A (ja) | 1983-11-12 |
| ES521887A0 (es) | 1984-01-16 |
| EP0092738A1 (de) | 1983-11-02 |
| EP0092738B1 (de) | 1985-07-24 |
| JPH0211581B2 (forum.php) | 1990-03-14 |
| ES8402260A1 (es) | 1984-01-16 |
| DE3360430D1 (en) | 1985-08-29 |
| US4692550A (en) | 1987-09-08 |
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