CA2199913C - Heat exchange media for the thermal cracking of carbamidic acid esters - Google Patents
Heat exchange media for the thermal cracking of carbamidic acid esters Download PDFInfo
- Publication number
- CA2199913C CA2199913C CA002199913A CA2199913A CA2199913C CA 2199913 C CA2199913 C CA 2199913C CA 002199913 A CA002199913 A CA 002199913A CA 2199913 A CA2199913 A CA 2199913A CA 2199913 C CA2199913 C CA 2199913C
- Authority
- CA
- Canada
- Prior art keywords
- cracking
- column
- boiling
- solvent
- acid esters
- 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
- 239000002253 acid Substances 0.000 title claims abstract description 33
- 150000002148 esters Chemical class 0.000 title claims abstract description 33
- 238000004227 thermal cracking Methods 0.000 title abstract description 8
- 238000005336 cracking Methods 0.000 claims abstract description 65
- 238000009835 boiling Methods 0.000 claims abstract description 42
- 239000002904 solvent Substances 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims description 30
- 238000012546 transfer Methods 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 11
- 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 9
- 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 4
- 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 3
- JQCVPZXMGXKNOD-UHFFFAOYSA-N 1,2-dibenzylbenzene Chemical compound C=1C=CC=C(CC=2C=CC=CC=2)C=1CC1=CC=CC=C1 JQCVPZXMGXKNOD-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000006227 byproduct Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- -1 aliphatic hydrocarbon radical Chemical class 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 238000012856 packing Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012442 inert solvent Substances 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 229910052751 metal Inorganic materials 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
- 239000003921 oil Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000004808 supercritical fluid chromatography Methods 0.000 description 2
- 150000001911 terphenyls Chemical class 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical class C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 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
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines 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
- RNQSDMQMQXQMPP-UHFFFAOYSA-N butyl n-[12-(butoxycarbonylamino)dodecyl]carbamate Chemical compound CCCCOC(=O)NCCCCCCCCCCCCNC(=O)OCCCC RNQSDMQMQXQMPP-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
- 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
- 239000004202 carbamide Substances 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 238000005516 engineering process Methods 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 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
- 239000011552 falling film Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 238000010438 heat treatment Methods 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
- 230000002045 lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 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
- 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
- CSIDQAACVLDAJD-UHFFFAOYSA-N methyl n-[12-(methoxycarbonylamino)dodecyl]carbamate Chemical compound COC(=O)NCCCCCCCCCCCCNC(=O)OC CSIDQAACVLDAJD-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
- 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
- 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
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000007787 solid Substances 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
- 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
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure 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)
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 (2)
| Publication Number | Publication Date |
|---|---|
| CA2199913A1 CA2199913A1 (en) | 1997-09-15 |
| CA2199913C true CA2199913C (en) | 2006-05-16 |
Family
ID=26023837
Family Applications (2)
| 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 |
| CA002199919A Abandoned CA2199919A1 (en) | 1996-03-15 | 1997-03-13 | Process for thermally cracking carbamic acid esters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002199919A Abandoned CA2199919A1 (en) | 1996-03-15 | 1997-03-13 | Process for thermally cracking carbamic acid esters |
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) |
Families Citing this family (26)
| 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 |
| EA201390504A1 (ru) * | 2010-10-04 | 2013-08-30 | Асахи Касеи Кемикалз Корпорейшн | Способ разделения и способ получения изоцианата |
| 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 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
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 |
| EP0795543A1 (de) | 1997-09-17 |
| DE59705128D1 (de) | 2001-12-06 |
| CA2199919A1 (en) | 1997-09-15 |
| JP4031550B2 (ja) | 2008-01-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |