KR20120120945A - 카르바메이트의 열적 분열에 의한 이소시아네이트의 제조 방법 - Google Patents
카르바메이트의 열적 분열에 의한 이소시아네이트의 제조 방법 Download PDFInfo
- Publication number
- KR20120120945A KR20120120945A KR1020127021646A KR20127021646A KR20120120945A KR 20120120945 A KR20120120945 A KR 20120120945A KR 1020127021646 A KR1020127021646 A KR 1020127021646A KR 20127021646 A KR20127021646 A KR 20127021646A KR 20120120945 A KR20120120945 A KR 20120120945A
- Authority
- KR
- South Korea
- Prior art keywords
- carbamate
- column
- section
- cleavage
- stream
- 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- Withdrawn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
- 239000012948 isocyanate Substances 0.000 title claims abstract description 27
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 150000004657 carbamic acid derivatives Chemical class 0.000 title description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 32
- 238000003776 cleavage reaction Methods 0.000 claims abstract description 29
- 230000007017 scission Effects 0.000 claims abstract description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000009835 boiling Methods 0.000 claims abstract description 26
- 239000012442 inert solvent Substances 0.000 claims abstract description 17
- 238000005878 carbamate elimination reaction Methods 0.000 claims abstract description 13
- 150000001298 alcohols Chemical class 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- 239000000470 constituent Substances 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 18
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000011552 falling film Substances 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- 238000010494 dissociation reaction Methods 0.000 claims description 3
- 230000005593 dissociations Effects 0.000 claims description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 7
- 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 7
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- -1 aliphatic isocyanates Chemical class 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 125000005628 tolylene group Chemical group 0.000 description 4
- 238000011109 contamination Methods 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 150000003673 urethanes Chemical class 0.000 description 3
- 239000006200 vaporizer Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 2
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 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 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PBWHJRFXUPLZDS-UHFFFAOYSA-N (1-Ethylpropyl)benzene Chemical compound CCC(CC)C1=CC=CC=C1 PBWHJRFXUPLZDS-UHFFFAOYSA-N 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- VPHBYBUYWBZLEX-UHFFFAOYSA-N 1,2-dipropylbenzene Chemical compound CCCC1=CC=CC=C1CCC VPHBYBUYWBZLEX-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- KEIQPMUPONZJJH-UHFFFAOYSA-N dicyclohexylmethanediamine Chemical compound C1CCCCC1C(N)(N)C1CCCCC1 KEIQPMUPONZJJH-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Images
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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10151089 | 2010-01-19 | ||
| EP10151089.9 | 2010-01-19 | ||
| PCT/EP2011/050557 WO2011089098A1 (de) | 2010-01-19 | 2011-01-18 | Verfahren zur herstellung von isocyanaten durch thermische spaltung von carbamaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20120120945A true KR20120120945A (ko) | 2012-11-02 |
Family
ID=43769079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127021646A Withdrawn KR20120120945A (ko) | 2010-01-19 | 2011-01-18 | 카르바메이트의 열적 분열에 의한 이소시아네이트의 제조 방법 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP2526085B1 (enExample) |
| JP (1) | JP5823982B2 (enExample) |
| KR (1) | KR20120120945A (enExample) |
| CN (1) | CN102712580B (enExample) |
| BR (1) | BR112012017877A2 (enExample) |
| ES (1) | ES2552837T3 (enExample) |
| HU (1) | HUE028076T2 (enExample) |
| PL (1) | PL2526085T3 (enExample) |
| PT (1) | PT2526085E (enExample) |
| WO (1) | WO2011089098A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI430978B (zh) * | 2010-10-04 | 2014-03-21 | Asahi Kasei Chemicals Corp | 分離方法及異氰酸酯之製造方法 |
| US8933262B2 (en) | 2011-05-24 | 2015-01-13 | Basf Se | Process for preparing polyisocyanates from biomass |
| CN103848758A (zh) * | 2012-12-06 | 2014-06-11 | 中国科学院成都有机化学有限公司 | 一种催化热分解制备异氰酸酯的方法 |
| EP3797744A1 (en) | 2014-05-09 | 2021-03-31 | 3M Innovative Properties Company | Dressing with contracting layer for linear tissue sites |
| US10898217B2 (en) | 2014-05-09 | 2021-01-26 | Kci Licensing, Inc. | Dressing providing apertures with multiple orifice sizes for negative-pressure therapy |
| AU2015255726B2 (en) | 2014-05-09 | 2020-03-05 | Solventum Intellectual Properties Company | Disruptive dressing for use with negative pressure and fluid instillation |
| EP3527180B1 (en) | 2014-05-09 | 2021-01-06 | 3M Innovative Properties Company | Debriding dressing for use with negative pressure and fluid instillation |
| CN107207422B (zh) * | 2015-01-30 | 2020-12-11 | 巴斯夫欧洲公司 | 低副产物的多亚苯基多亚甲基多异氰酸酯 |
| CN110546135B (zh) * | 2017-05-15 | 2021-12-14 | 旭化成株式会社 | 异氰酸酯的制造方法 |
| EP3450424A1 (de) * | 2017-09-04 | 2019-03-06 | Covestro Deutschland AG | Verfahren zur herstellung von isocyanaten |
| EP3876885B1 (en) | 2018-11-08 | 2023-11-29 | 3M Innovative Properties Company | Wound dressing with semi-rigid support to increase disruption using perforated dressing and negative pressure wound therapy |
| WO2021111412A1 (en) | 2019-12-05 | 2021-06-10 | Kci Licensing, Inc. | Multi-layer negative pressure incisional wound therapy dressing |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3215591A1 (de) * | 1982-04-27 | 1983-10-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureestern |
| JPS60231640A (ja) * | 1984-05-02 | 1985-11-18 | Asahi Chem Ind Co Ltd | イソシアナ−トの連続的製法 |
| JPH02250857A (ja) * | 1989-03-23 | 1990-10-08 | Sumitomo Metal Ind Ltd | ポリイソシアネートの製造方法 |
| US5326903A (en) | 1992-01-10 | 1994-07-05 | Nippon Shokubai Co., Ltd. | Process for preparing isocyanates using sintered oxides |
| JPH05194351A (ja) * | 1992-01-22 | 1993-08-03 | Nkk Corp | イソシアネート化合物の連続的製造装置及び方法 |
| EP0795544B1 (de) * | 1996-03-15 | 2001-10-31 | Bayer Ag | Verfahren zur thermischen Spaltung von Carbamidsäureestern |
| DE19907648A1 (de) | 1999-02-23 | 2000-08-24 | Basf Ag | Verfahren zur Herstellung von Isocyanaten durch Spaltung von Urethanen |
| DE10329491A1 (de) * | 2003-07-01 | 2005-01-27 | Basf Ag | Reaktor für gas/flüssig oder gas/flüssig/fest Reaktionen |
| CN101200436A (zh) * | 2006-12-31 | 2008-06-18 | 中国科学院成都有机化学有限公司 | 连续制备1,6-六亚甲基二异氰酸酯的方法 |
| EP2265571B1 (de) | 2008-03-18 | 2015-03-04 | Basf Se | Verfahren zur herstellung von urethanen aus mono- und difunktionalen aromatischen aminen |
-
2011
- 2011-01-18 BR BR112012017877A patent/BR112012017877A2/pt not_active IP Right Cessation
- 2011-01-18 EP EP11700347.5A patent/EP2526085B1/de not_active Not-in-force
- 2011-01-18 ES ES11700347.5T patent/ES2552837T3/es active Active
- 2011-01-18 CN CN201180006310.9A patent/CN102712580B/zh not_active Expired - Fee Related
- 2011-01-18 KR KR1020127021646A patent/KR20120120945A/ko not_active Withdrawn
- 2011-01-18 PL PL11700347T patent/PL2526085T3/pl unknown
- 2011-01-18 JP JP2012549324A patent/JP5823982B2/ja not_active Expired - Fee Related
- 2011-01-18 WO PCT/EP2011/050557 patent/WO2011089098A1/de not_active Ceased
- 2011-01-18 HU HUE11700347A patent/HUE028076T2/en unknown
- 2011-01-18 PT PT117003475T patent/PT2526085E/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112012017877A2 (pt) | 2016-05-03 |
| PT2526085E (pt) | 2015-11-24 |
| CN102712580B (zh) | 2014-11-26 |
| EP2526085B1 (de) | 2015-08-12 |
| HUE028076T2 (en) | 2016-11-28 |
| JP5823982B2 (ja) | 2015-11-25 |
| PL2526085T3 (pl) | 2016-01-29 |
| ES2552837T3 (es) | 2015-12-02 |
| CN102712580A (zh) | 2012-10-03 |
| WO2011089098A1 (de) | 2011-07-28 |
| JP2013517312A (ja) | 2013-05-16 |
| EP2526085A1 (de) | 2012-11-28 |
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