JP4031550B2 - カルバミン酸エステルを熱分解する方法 - Google Patents
カルバミン酸エステルを熱分解する方法 Download PDFInfo
- Publication number
- JP4031550B2 JP4031550B2 JP07671497A JP7671497A JP4031550B2 JP 4031550 B2 JP4031550 B2 JP 4031550B2 JP 07671497 A JP07671497 A JP 07671497A JP 7671497 A JP7671497 A JP 7671497A JP 4031550 B2 JP4031550 B2 JP 4031550B2
- Authority
- JP
- Japan
- Prior art keywords
- zone
- reaction
- column
- evaporator
- carbamate
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 40
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 14
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 238000000354 decomposition reaction Methods 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 26
- 238000009835 boiling Methods 0.000 claims description 24
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 19
- 239000012948 isocyanate Substances 0.000 claims description 16
- 150000002513 isocyanates Chemical class 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 14
- 238000005336 cracking Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- -1 hydroxyl compound Chemical class 0.000 claims description 9
- 239000012535 impurity Substances 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 5
- UHJWZORSTYATLW-UHFFFAOYSA-N o-biphenylyl phenyl ether Natural products C=1C=CC=C(C=2C=CC=CC=2)C=1OC1=CC=CC=C1 UHJWZORSTYATLW-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000007791 liquid phase Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- CNPWIVIIZHULCN-UHFFFAOYSA-N 1-methyl-2,4-bis-(methoxycarbonylamino)-benzene Natural products COC(=O)NC1=CC=C(C)C(NC(=O)OC)=C1 CNPWIVIIZHULCN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000004808 supercritical fluid chromatography Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- IQMVYVPCFBUNTN-UHFFFAOYSA-N 2-methoxy-n-[6-[(2-methoxyacetyl)amino]hexyl]acetamide Chemical compound COCC(=O)NCCCCCCNC(=O)COC IQMVYVPCFBUNTN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
- OCBKYYBAGVCBDE-UHFFFAOYSA-N butyl 2-amino-2-[5-(butoxycarbonylamino)-1,3,3-trimethylcyclohexyl]acetate Chemical compound CCCCOC(=O)NC1CC(C)(C)CC(C)(C(N)C(=O)OCCCC)C1 OCBKYYBAGVCBDE-UHFFFAOYSA-N 0.000 description 1
- AGIKINZLPGZPSN-UHFFFAOYSA-N butyl n-[3-(butoxycarbonylamino)-2-methylphenyl]carbamate Chemical compound CCCCOC(=O)NC1=CC=CC(NC(=O)OCCCC)=C1C AGIKINZLPGZPSN-UHFFFAOYSA-N 0.000 description 1
- KOBZWUMLQLKNMP-UHFFFAOYSA-N butyl n-[3-(butoxycarbonylamino)-4-methylphenyl]carbamate Chemical compound CCCCOC(=O)NC1=CC=C(C)C(NC(=O)OCCCC)=C1 KOBZWUMLQLKNMP-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
- 239000004202 carbamide Substances 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 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 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 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
- FGDQQNQDAXHGBY-UHFFFAOYSA-N ethyl n-[8-(ethoxycarbonylamino)octyl]carbamate Chemical compound CCOC(=O)NCCCCCCCCNC(=O)OCC FGDQQNQDAXHGBY-UHFFFAOYSA-N 0.000 description 1
- LXDAZOICOOCGCB-UHFFFAOYSA-N ethyl n-[[3-[(2-ethoxycarbonylhydrazinyl)methyl]phenyl]methylamino]carbamate Chemical compound CCOC(=O)NNCC1=CC=CC(CNNC(=O)OCC)=C1 LXDAZOICOOCGCB-UHFFFAOYSA-N 0.000 description 1
- BQBKYSPXQYHTIP-UHFFFAOYSA-N ethyl n-butylcarbamate Chemical compound CCCCNC(=O)OCC BQBKYSPXQYHTIP-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ONDKZBMQUACRQG-UHFFFAOYSA-N methyl n-[1,6-bis(methoxycarbonylamino)hexan-3-yl]carbamate Chemical compound COC(=O)NCCCC(NC(=O)OC)CCNC(=O)OC ONDKZBMQUACRQG-UHFFFAOYSA-N 0.000 description 1
- RUDDKVKIAVQINV-UHFFFAOYSA-N methyl n-[10-(methoxycarbonylamino)decyl]carbamate Chemical compound COC(=O)NCCCCCCCCCCNC(=O)OC RUDDKVKIAVQINV-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
- BTUCYFNDGOMWQG-UHFFFAOYSA-N methyl n-[3-(methoxycarbonylamino)cyclohexyl]carbamate Chemical compound COC(=O)NC1CCCC(NC(=O)OC)C1 BTUCYFNDGOMWQG-UHFFFAOYSA-N 0.000 description 1
- BQFREXSKWBUSAP-UHFFFAOYSA-N methyl n-[3-(methoxycarbonylamino)phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(NC(=O)OC)=C1 BQFREXSKWBUSAP-UHFFFAOYSA-N 0.000 description 1
- BAMOLHXSXMKLAA-UHFFFAOYSA-N methyl n-[3-[(methoxycarbonylamino)methyl]-3,5,5-trimethylcyclohexyl]carbamate Chemical compound COC(=O)NCC1(C)CC(NC(=O)OC)CC(C)(C)C1 BAMOLHXSXMKLAA-UHFFFAOYSA-N 0.000 description 1
- VLPBGAPTYGNIII-UHFFFAOYSA-N methyl n-[4-[4-(methoxycarbonylamino)phenyl]phenyl]carbamate Chemical group C1=CC(NC(=O)OC)=CC=C1C1=CC=C(NC(=O)OC)C=C1 VLPBGAPTYGNIII-UHFFFAOYSA-N 0.000 description 1
- GLRSKDCBNNEWJE-UHFFFAOYSA-N methyl n-[5-(methoxycarbonylamino)pentyl]carbamate Chemical compound COC(=O)NCCCCCNC(=O)OC GLRSKDCBNNEWJE-UHFFFAOYSA-N 0.000 description 1
- JEMNNWYZZZUVQI-UHFFFAOYSA-N methyl n-[[3-[(methoxycarbonylamino)methyl]phenyl]methyl]carbamate Chemical compound COC(=O)NCC1=CC=CC(CNC(=O)OC)=C1 JEMNNWYZZZUVQI-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- VOQWIAQVTYSSPY-UHFFFAOYSA-N phenyl n-[1,6-bis(phenoxycarbonylamino)hexan-3-yl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NCCCC(NC(=O)OC=1C=CC=CC=1)CCNC(=O)OC1=CC=CC=C1 VOQWIAQVTYSSPY-UHFFFAOYSA-N 0.000 description 1
- PVYDCVJTVNXZRB-UHFFFAOYSA-N phenyl n-[12-(phenoxycarbonylamino)dodecyl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NCCCCCCCCCCCCNC(=O)OC1=CC=CC=C1 PVYDCVJTVNXZRB-UHFFFAOYSA-N 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
- 229920000642 polymer Polymers 0.000 description 1
- KKVSYFFZJJRQPA-UHFFFAOYSA-N propyl n-(4-propylphenyl)carbamate Chemical compound CCCOC(=O)NC1=CC=C(CCC)C=C1 KKVSYFFZJJRQPA-UHFFFAOYSA-N 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 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 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000006839 xylylene group Chemical group 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19610261 | 1996-03-15 | ||
| DE19610261.8 | 1996-03-15 | ||
| DE19618828A DE19618828A1 (de) | 1996-05-10 | 1996-05-10 | Verwendung von hochsiedenden Lösemitteln bzw. -gemischen als Wärmetauschmedium für die thermische Spaltung von Carbamidsäureestern |
| DE19618828.8 | 1996-05-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH09249632A JPH09249632A (ja) | 1997-09-22 |
| JPH09249632A5 JPH09249632A5 (enExample) | 2005-02-10 |
| JP4031550B2 true JP4031550B2 (ja) | 2008-01-09 |
Family
ID=26023837
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP07671597A Expired - Fee Related JP4031551B2 (ja) | 1996-03-15 | 1997-03-13 | カルバミド酸エステルを熱分解するための熱交換媒体 |
| JP07671497A Expired - Fee Related JP4031550B2 (ja) | 1996-03-15 | 1997-03-13 | カルバミン酸エステルを熱分解する方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP07671597A Expired - Fee Related JP4031551B2 (ja) | 1996-03-15 | 1997-03-13 | カルバミド酸エステルを熱分解するための熱交換媒体 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US5731458A (enExample) |
| EP (2) | EP0795543B1 (enExample) |
| JP (2) | JP4031551B2 (enExample) |
| CA (2) | CA2199913C (enExample) |
| DE (2) | DE59705127D1 (enExample) |
| ES (2) | ES2166922T3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11192853B2 (en) * | 2010-10-04 | 2021-12-07 | Asahi Kasei Chemicals Corporation | Separation method and method for producing isocyanate |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6008396A (en) * | 1997-04-11 | 1999-12-28 | Osi Specialties, Inc. | Hot oil process for producing isocyanato organosilanes |
| US6350927B2 (en) | 1997-05-09 | 2002-02-26 | The Dow Chemical Company | Thermal fluid blends containing 1,2,3,4-tetrahydro (1-phenylethyl)naphthalene |
| EP0980410B1 (en) * | 1997-05-09 | 2002-03-27 | The Dow Chemical Company | Thermal fluid blends containing 1,2,3,4-tetrahydro(1-phenylethyl)naphthalene |
| DE19813107A1 (de) | 1998-03-25 | 1999-09-30 | Basf Ag | Verfahren zur Herstellung von Polyurethanschaumstoffen |
| CN1186317C (zh) * | 2000-02-29 | 2005-01-26 | 亨茨曼国际有限公司 | 制备有机多异氰酸酯的方法 |
| SG115512A1 (en) | 2001-12-28 | 2005-10-28 | Mitsui Takeda Chemicals Inc | Method for producing carbamates and method for producing isocyanates |
| JP4859255B2 (ja) * | 2006-11-17 | 2012-01-25 | 旭化成ケミカルズ株式会社 | イソシアネートの製造方法 |
| 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 |
| WO2009139062A1 (ja) * | 2008-05-15 | 2009-11-19 | 旭化成ケミカルズ株式会社 | イソシアネートの製造方法 |
| EP2275405B1 (en) * | 2008-05-15 | 2019-04-24 | Asahi Kasei Kabushiki Kaisha | Process for producing isocyanate using diaryl carbonate |
| WO2011067242A1 (de) | 2009-12-01 | 2011-06-09 | Basf Se | Verfahren zur herstellung von isocyanaten durch thermische spaltung von carbamaten |
| PT2507206E (pt) | 2009-12-04 | 2014-12-26 | Basf Se | Método para a produção de isocianatos |
| JP5823982B2 (ja) * | 2010-01-19 | 2015-11-25 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | カルバメートの熱的分離によるイソシアネートの調製方法 |
| US8680323B2 (en) | 2010-01-19 | 2014-03-25 | Basf Se | Process for preparing isocyanates by thermal dissociation of carbamates |
| JP2013540101A (ja) | 2010-06-22 | 2013-10-31 | ビーエーエスエフ ソシエタス・ヨーロピア | イソシアネートの合成のための固体ルイス酸上での不均一系触媒によるカルバメートの解離 |
| CN102653517A (zh) * | 2011-03-02 | 2012-09-05 | 中国科学院过程工程研究所 | 一种由氨基甲酸酯制备异氰酸酯的方法 |
| JP5700595B2 (ja) | 2012-01-25 | 2015-04-15 | 旭化成ケミカルズ株式会社 | 分離方法 |
| JP5650777B2 (ja) * | 2013-03-11 | 2015-01-07 | 旭化成ケミカルズ株式会社 | 炭酸ジアリールを用いるイソシアネートの製造方法 |
| WO2016010900A1 (en) | 2014-07-14 | 2016-01-21 | Momentive Performance Materials Inc. | Process for producing low-color and color-stable isocyanatoorganosilanes and products derived therefrom |
| WO2016156188A1 (de) | 2015-03-31 | 2016-10-06 | Basf Se | Verfahren zur herstellung von isocyanaten durch carbamatspaltung |
| US10968168B2 (en) | 2017-05-15 | 2021-04-06 | Asahi Kasei Kabushiki Kaisha | Isocyanate production method |
| US11655263B2 (en) | 2018-07-13 | 2023-05-23 | Momentive Performance Materials Inc | Preparation of isocyanatosilanes |
| CN111303373B (zh) * | 2020-02-25 | 2022-07-12 | 万华化学集团股份有限公司 | 一种低色度脲基甲酸酯组合物及其制备方法和应用 |
| CN116177484A (zh) * | 2023-03-04 | 2023-05-30 | 福州大学 | 一种液体有机氢载体全氢苄基甲苯的反应精馏脱氢工艺 |
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| 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 |
| US3919278A (en) * | 1974-06-13 | 1975-11-11 | Atlantic Richfield Co | Production of isocyanates from lower alkyl esters of mononuclear aromatic carbamic acids |
| DE2942543A1 (de) * | 1979-10-20 | 1981-05-07 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von arylisocyanaten durch thermische spaltung von arylurethanen |
| 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 |
| DE3108990A1 (de) * | 1981-03-10 | 1982-09-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyisocyanaten |
| DE3142627A1 (de) * | 1981-10-28 | 1983-05-05 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von isocyanaten durch thermische spaltung von urethanen |
| DE3215591A1 (de) * | 1982-04-27 | 1983-10-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureestern |
| EP0100047B1 (de) * | 1982-07-24 | 1986-02-12 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Hexamethylen-diisocyanat-1,6 und/oder isomeren Diisocyanaten mit 6 Kohlenstoffatomen im Alkylenrest |
| DE3314790A1 (de) * | 1983-04-23 | 1984-10-25 | Basf Ag, 6700 Ludwigshafen | Mehrstufenverfahren zur herstellung von 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanat |
| DE3314788A1 (de) * | 1983-04-23 | 1984-10-25 | Basf Ag, 6700 Ludwigshafen | Mehrstufenverfahren zur herstellung von hexamethylendiisocyanat-1,6 und/oder isomeren aliphatischen diisocyanaten mit 6 kohlenstoffatomen im alkylenrest |
| US4599401A (en) * | 1983-10-27 | 1986-07-08 | Union Carbide Corporation | Low viscosity adducts of poly(active hydrogen) organic compounds and a polyepoxide |
| DE3339300A1 (de) * | 1983-10-29 | 1985-05-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von isocyanaten durch thermische spaltung von urethanen |
| DE3632010A1 (de) * | 1986-09-20 | 1988-04-07 | Basf Ag | Neue 2-(alkoxymethyl)-pentan-1,5-diisocyanate, -diurethane und -dicarbamidsaeurechloride, verfahren zu ihrer herstellung und deren verwendung |
| DE3850647T2 (de) * | 1987-01-13 | 1994-11-17 | Daicel Chem | Verfahren zur herstellung von isocyanat-verbindungen. |
| DE3828033A1 (de) * | 1988-08-18 | 1990-03-08 | Huels Chemische Werke Ag | Kreislaufverfahren zur herstellung von (cyclo)aliphatischen diisocyanaten |
| DE3915181A1 (de) * | 1989-05-10 | 1990-11-15 | Bayer Ag | Verfahren zur herstellung von polyisocyanaten |
| DE4010226A1 (de) * | 1990-03-30 | 1991-10-02 | Basf Ag | Neue 2,2-dialkylpentan-1,5-diisocyanate, -diurethane und -dicarbamidsaeurechloride, verfahren zu ihrer herstellung und ihre verwendung |
| DE4124671A1 (de) * | 1991-07-25 | 1993-01-28 | Basf Ag | Reaktor und verfahren zur thermischen spaltung von carbamidsaeureestern |
| DE4137428A1 (de) * | 1991-11-14 | 1993-05-19 | Bayer Ag | Verfahren zur herstellung von polyisocyanaten |
| 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 |
| DE4413580A1 (de) * | 1994-04-19 | 1995-10-26 | Bayer Ag | Verfahren zur Herstellung von 1,4-Diisocyanatobutan (BDI) |
-
1997
- 1997-03-03 ES ES97103444T patent/ES2166922T3/es not_active Expired - Lifetime
- 1997-03-03 EP EP97103444A patent/EP0795543B1/de not_active Expired - Lifetime
- 1997-03-03 DE DE59705127T patent/DE59705127D1/de not_active Expired - Lifetime
- 1997-03-03 ES ES97103445T patent/ES2166923T3/es not_active Expired - Lifetime
- 1997-03-03 DE DE59705128T patent/DE59705128D1/de not_active Expired - Lifetime
- 1997-03-03 EP EP97103445A patent/EP0795544B1/de not_active Expired - Lifetime
- 1997-03-06 US US08/811,801 patent/US5731458A/en not_active Expired - Lifetime
- 1997-03-06 US US08/812,610 patent/US5883291A/en not_active Expired - Lifetime
- 1997-03-13 CA CA002199913A patent/CA2199913C/en not_active Expired - Fee Related
- 1997-03-13 JP JP07671597A patent/JP4031551B2/ja not_active Expired - Fee Related
- 1997-03-13 JP JP07671497A patent/JP4031550B2/ja not_active Expired - Fee Related
- 1997-03-13 CA CA002199919A patent/CA2199919A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11192853B2 (en) * | 2010-10-04 | 2021-12-07 | Asahi Kasei Chemicals Corporation | Separation method and method for producing isocyanate |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4031551B2 (ja) | 2008-01-09 |
| US5731458A (en) | 1998-03-24 |
| JPH09249633A (ja) | 1997-09-22 |
| DE59705127D1 (de) | 2001-12-06 |
| EP0795544A1 (de) | 1997-09-17 |
| CA2199913A1 (en) | 1997-09-15 |
| US5883291A (en) | 1999-03-16 |
| EP0795544B1 (de) | 2001-10-31 |
| EP0795543B1 (de) | 2001-10-31 |
| JPH09249632A (ja) | 1997-09-22 |
| ES2166922T3 (es) | 2002-05-01 |
| ES2166923T3 (es) | 2002-05-01 |
| CA2199913C (en) | 2006-05-16 |
| EP0795543A1 (de) | 1997-09-17 |
| DE59705128D1 (de) | 2001-12-06 |
| CA2199919A1 (en) | 1997-09-15 |
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