CA2199919A1 - Process for thermally cracking carbamic acid esters - Google Patents

Process for thermally cracking carbamic acid esters

Info

Publication number: CA2199919A1
Authority: CA; Canada
Prior art keywords: zone; carbamic acid; reaction; column; cracking
Prior art date: 1996-03-15
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002199919A

Other languages

English (en)

French (fr)

Inventor

Jurgen Dahmer

Dieter Schleenstein

Heinrich Steude

Oswald Wilmes

Christian Rasp

Georg Ronge

Klaus Nachtkamp

Wilfried Litz

Stephan Kabelac

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-03-15

Filing date

1997-03-13

Publication date

1997-09-15

1996-05-10 Priority claimed from DE19618828A external-priority patent/DE19618828A1/de

1997-03-13 Application filed by Individual filed Critical Individual

1997-09-15 Publication of CA2199919A1 publication Critical patent/CA2199919A1/en

Status Abandoned legal-status Critical Current

Links

238000005336 cracking Methods 0.000 title claims abstract description 54
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 44
238000000034 method Methods 0.000 title claims abstract description 37
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims abstract description 24
238000006243 chemical reaction Methods 0.000 claims abstract description 39
239000002904 solvent Substances 0.000 claims abstract description 26
238000009835 boiling Methods 0.000 claims abstract description 23
239000012948 isocyanate Substances 0.000 claims abstract description 16
150000002513 isocyanates Chemical class 0.000 claims abstract description 15
-1 hydroxyl compound Chemical class 0.000 claims description 20
239000007788 liquid Substances 0.000 claims description 14
239000003054 catalyst Substances 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
238000000354 decomposition reaction Methods 0.000 claims description 7
238000012546 transfer Methods 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 5
239000012535 impurity Substances 0.000 claims description 5
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
GDPISEKNRFFKMM-UHFFFAOYSA-N 1,3-diphenylpropan-2-ylbenzene Chemical class C=1C=CC=CC=1CC(C=1C=CC=CC=1)CC1=CC=CC=C1 GDPISEKNRFFKMM-UHFFFAOYSA-N 0.000 claims description 2
150000001911 terphenyls Chemical class 0.000 claims description 2
238000004064 recycling Methods 0.000 claims 2
239000007791 liquid phase Substances 0.000 abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
239000000047 product Substances 0.000 description 22
239000006227 byproduct Substances 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 11
238000010992 reflux Methods 0.000 description 10
238000004821 distillation Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
238000012856 packing Methods 0.000 description 7
238000000926 separation method Methods 0.000 description 6
239000004215 Carbon black (E152) Substances 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
239000007789 gas Substances 0.000 description 5
229930195733 hydrocarbon Natural products 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
238000010438 heat treatment Methods 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
238000011068 loading method Methods 0.000 description 3
238000010517 secondary reaction Methods 0.000 description 3
239000007858 starting material Substances 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
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000004744 fabric Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000004808 supercritical fluid chromatography Methods 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
238000010626 work up procedure Methods 0.000 description 2
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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
230000018199 S phase Effects 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 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
230000003466 anti-cipated effect Effects 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
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
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
ILPOVPZIWGHRLX-UHFFFAOYSA-N butyl n-[6-(butoxycarbonylamino)hexyl]carbamate Chemical compound CCCCOC(=O)NCCCCCCNC(=O)OCCCC ILPOVPZIWGHRLX-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 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
238000011109 contamination Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000001419 dependent effect 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
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 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
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
239000011552 falling film Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 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
230000002045 lasting effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002736 metal compounds Chemical class 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
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
DXZCANUBKZARPR-UHFFFAOYSA-N methyl n-[6-(methoxycarbonylamino)hexyl]carbamate Chemical compound COC(=O)NCCCCCCNC(=O)OC DXZCANUBKZARPR-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
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
239000001294 propane Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000010409 thin film Substances 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
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
238000005292 vacuum distillation Methods 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)

CA002199919A 1996-03-15 1997-03-13 Process for thermally cracking carbamic acid esters Abandoned CA2199919A1 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19610261		1996-03-15
DE19610261.8		1996-05-10
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 (1)

Publication Number	Publication Date
CA2199919A1 true CA2199919A1 (en)	1997-09-15

Family

ID=26023837

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA002199919A Abandoned CA2199919A1 (en)	1996-03-15	1997-03-13	Process for thermally cracking carbamic acid esters
CA002199913A Expired - Fee Related CA2199913C (en)	1996-03-15	1997-03-13	Heat exchange media for the thermal cracking of carbamidic acid esters

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA002199913A Expired - Fee Related CA2199913C (en)	1996-03-15	1997-03-13	Heat exchange media for the thermal cracking of carbamidic acid esters

Country Status (6)

Country	Link
US (2)	US5731458A (2)
EP (2)	EP0795543B1 (2)
JP (2)	JP4031551B2 (2)
CA (2)	CA2199919A1 (2)
DE (2)	DE59705128D1 (2)
ES (2)	ES2166923T3 (2)

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US6350927B2 (en)	1997-05-09	2002-02-26	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
JP2003525267A (ja)	2000-02-29	2003-08-26	ハンツマン・インターナショナル・エルエルシー	有機ポリイソシアネートの製造法
SG115512A1 (en)	2001-12-28	2005-10-28	Mitsui Takeda Chemicals Inc	Method for producing carbamates and method for producing isocyanates
ATE495149T1 (de) *	2006-11-17	2011-01-15	Asahi Kasei Chemicals Corp	Verfahren zur herstellung von isocyanaten
TW200844080A (en) *	2007-01-11	2008-11-16	Asahi Kasei Chemicals Corp	Process for producing isocyanate
WO2008120645A1 (ja)	2007-03-30	2008-10-09	Asahi Kasei Chemicals Corporation	カルバミン酸エステルおよび芳香族ヒドロキシ化合物を含む組成物を用いるイソシアネートの製造方法、ならびにカルバミン酸エステル移送用および貯蔵用組成物
JP5592786B2 (ja) *	2008-05-15	2014-09-17	旭化成ケミカルズ株式会社	イソシアネートの製造方法
RU2523201C2 (ru) *	2008-05-15	2014-07-20	Асахи Касеи Кемикалз Корпорейшн	Способ получения изоцианатов с использованием диарилкарбоната
PL2507205T3 (pl)	2009-12-01	2014-12-31	Basf Se	Sposób wytwarzania izocyjanianów przez termiczne rozszczepianie karbaminianów
KR20120091428A (ko)	2009-12-04	2012-08-17	바스프 에스이	이소시아네이트의 제조 방법
US8680323B2 (en)	2010-01-19	2014-03-25	Basf Se	Process for preparing isocyanates by thermal dissociation of carbamates
WO2011089098A1 (de) *	2010-01-19	2011-07-28	Basf Se	Verfahren zur herstellung von isocyanaten durch thermische spaltung von carbamaten
CN102947267A (zh)	2010-06-22	2013-02-27	巴斯夫欧洲公司	在固体路易斯酸上非均相催化氨基甲酸酯离解以合成异氰酸酯
JP5612115B2 (ja)	2010-10-04	2014-10-22	旭化成ケミカルズ株式会社	分離方法及びイソシアネートの製造方法
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
SG2013017017A (en)	2012-01-25	2014-09-26	Asahi Kasei Chemicals Corp	A method of separation
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
CN106488922B (zh)	2014-07-14	2019-10-11	莫门蒂夫性能材料股份有限公司	低色度和颜色稳定的异氰酸基有机硅烷的制造方法和由其衍生的产品
WO2016156188A1 (de)	2015-03-31	2016-10-06	Basf Se	Verfahren zur herstellung von isocyanaten durch carbamatspaltung
JP6757468B2 (ja)	2017-05-15	2020-09-16	旭化成株式会社	イソシアネートの製造方法
WO2020014040A1 (en) *	2018-07-13	2020-01-16	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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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
DE3362121D1 (en) *	1982-07-24	1986-03-27	Basf Ag	Process for the preparation of hexamethylene diisocyanate-1,6 and/or of the isomeric diisocyanates with 6 carbon atoms in the alkyl group
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
WO1988005430A1 (fr) *	1987-01-13	1988-07-28	Daicel Chemical Industries, Ltd.	Procede de preparation de composes d'isocyanate
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 DE DE59705128T patent/DE59705128D1/de not_active Expired - Lifetime
- 1997-03-03 ES ES97103445T patent/ES2166923T3/es not_active Expired - Lifetime
- 1997-03-03 DE DE59705127T patent/DE59705127D1/de not_active Expired - Lifetime
- 1997-03-03 EP EP97103444A patent/EP0795543B1/de not_active Expired - Lifetime
- 1997-03-03 ES ES97103444T patent/ES2166922T3/es 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 CA002199919A patent/CA2199919A1/en not_active Abandoned
- 1997-03-13 JP JP07671597A patent/JP4031551B2/ja not_active Expired - Fee Related
- 1997-03-13 CA CA002199913A patent/CA2199913C/en not_active Expired - Fee Related
- 1997-03-13 JP JP07671497A patent/JP4031550B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0795543B1 (de)	2001-10-31
ES2166922T3 (es)	2002-05-01
JP4031551B2 (ja)	2008-01-09
US5883291A (en)	1999-03-16
ES2166923T3 (es)	2002-05-01
CA2199913C (en)	2006-05-16
CA2199913A1 (en)	1997-09-15
DE59705128D1 (de)	2001-12-06
JPH09249633A (ja)	1997-09-22
DE59705127D1 (de)	2001-12-06
EP0795544B1 (de)	2001-10-31
US5731458A (en)	1998-03-24
JPH09249632A (ja)	1997-09-22
JP4031550B2 (ja)	2008-01-09
EP0795544A1 (de)	1997-09-17
EP0795543A1 (de)	1997-09-17

Legal Events

Date	Code	Title	Description
2002-03-08	EEER	Examination request
2008-02-04	FZDE	Discontinued

Publication	Publication Date	Title
US5731458A (en)	1998-03-24	Process for thermally cracking carbamic acid esters
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CA1318683C (en)	1993-06-01	Circulation process for the production of aliphatic and cycloaliphatic diisocyanates
JPH09249632A5 (2)	2005-02-10
US5616784A (en)	1997-04-01	Thermal cleavage of carbamic esters
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US5284969A (en)	1994-02-08	Process for the production of polyisocyanates
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