RU2543381C2 - Способ получения изоцианатов в газовой фазе - Google Patents
Способ получения изоцианатов в газовой фазе Download PDFInfo
- Publication number
- RU2543381C2 RU2543381C2 RU2012104325/04A RU2012104325A RU2543381C2 RU 2543381 C2 RU2543381 C2 RU 2543381C2 RU 2012104325/04 A RU2012104325/04 A RU 2012104325/04A RU 2012104325 A RU2012104325 A RU 2012104325A RU 2543381 C2 RU2543381 C2 RU 2543381C2
- Authority
- RU
- Russia
- Prior art keywords
- inert substance
- reaction
- reactor
- inert
- amine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 64
- 239000012948 isocyanate Substances 0.000 title description 24
- 150000002513 isocyanates Chemical class 0.000 title description 24
- 239000000126 substance Substances 0.000 claims abstract description 119
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 45
- 125000003277 amino group Chemical group 0.000 claims abstract description 10
- 150000004985 diamines Chemical class 0.000 claims abstract description 9
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 4
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims abstract 7
- 238000006243 chemical reaction Methods 0.000 claims description 87
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- 239000007789 gas Substances 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 21
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000007138 Deacon process reaction Methods 0.000 claims description 11
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 10
- 229940117389 dichlorobenzene Drugs 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052756 noble gas Inorganic materials 0.000 claims description 4
- 150000002835 noble gases Chemical class 0.000 claims description 4
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 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 claims description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
- PYVNHBWAEAENNL-UHFFFAOYSA-N azane;hexane Chemical compound N.N.CCCCCC PYVNHBWAEAENNL-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 27
- 230000015572 biosynthetic process Effects 0.000 abstract description 18
- 230000003993 interaction Effects 0.000 abstract description 15
- 239000006227 byproduct Substances 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 6
- 239000007787 solid Substances 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 description 78
- 238000001704 evaporation Methods 0.000 description 33
- 230000008020 evaporation Effects 0.000 description 33
- 238000002156 mixing Methods 0.000 description 29
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 27
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000012071 phase Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 18
- 238000001816 cooling Methods 0.000 description 16
- 238000010791 quenching Methods 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 230000000171 quenching effect Effects 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 238000009833 condensation Methods 0.000 description 13
- 230000005494 condensation Effects 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000003085 diluting agent Substances 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 230000004907 flux Effects 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- -1 aromatic primary amines Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000010574 gas phase reaction Methods 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 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 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000007792 gaseous phase Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NKSIIRSBNOHZRI-UHFFFAOYSA-N (3,3,4-trimethylcyclohexyl)methanamine Chemical compound CC1CCC(CN)CC1(C)C NKSIIRSBNOHZRI-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000009827 uniform distribution 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
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
- C07C263/20—Separation; Purification
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 |
|---|---|---|---|
| DE102009032414A DE102009032414A1 (de) | 2009-07-09 | 2009-07-09 | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| DE102009032414.3 | 2009-07-09 | ||
| PCT/EP2010/003915 WO2011003531A1 (de) | 2009-07-09 | 2010-06-26 | Verfahren zur herstellung von isocyanaten in der gasphase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012104325A RU2012104325A (ru) | 2013-08-20 |
| RU2543381C2 true RU2543381C2 (ru) | 2015-02-27 |
Family
ID=42599688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012104325/04A RU2543381C2 (ru) | 2009-07-09 | 2010-06-26 | Способ получения изоцианатов в газовой фазе |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8563767B2 (OSRAM) |
| EP (1) | EP2451774B1 (OSRAM) |
| JP (1) | JP5717735B2 (OSRAM) |
| KR (1) | KR20120038436A (OSRAM) |
| CN (1) | CN102498092B (OSRAM) |
| DE (1) | DE102009032414A1 (OSRAM) |
| HU (1) | HUE025762T2 (OSRAM) |
| IN (1) | IN2012DN00244A (OSRAM) |
| RU (1) | RU2543381C2 (OSRAM) |
| TW (1) | TWI457315B (OSRAM) |
| WO (1) | WO2011003531A1 (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2559658A1 (en) * | 2011-08-19 | 2013-02-20 | Huntsman International LLC | A process to separate phosgene and hydrogen chloride from a fluid stream comprising phosgene and hydrogen chloride |
| US8816126B2 (en) | 2011-09-02 | 2014-08-26 | Basf Se | Process for preparing isocyanates |
| CN110511164A (zh) * | 2011-09-02 | 2019-11-29 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| CN105214568B (zh) | 2014-06-10 | 2018-04-20 | 万华化学集团股份有限公司 | 一种加热器、该加热器的用途和应用该加热器制备异氰酸酯的方法 |
| US10851048B2 (en) * | 2018-11-13 | 2020-12-01 | Covestro Deutschland Ag | Process for preparing an isocyanate by partly adiabatically operated phosgenation of the corresponding amine |
| CN114044745A (zh) * | 2021-12-06 | 2022-02-15 | 甘肃银光聚银化工有限公司 | 一种气相光气化法合成1，5-戊二异氰酸酯的方法 |
| CN114195683B (zh) * | 2021-12-14 | 2023-03-17 | 山东新和成维生素有限公司 | 一种采用气相反应器制备异氰酸酯的方法及气相反应器 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2060560A1 (en) * | 2007-11-14 | 2009-05-20 | Bayer MaterialScience AG | Preparation of light-colored isocyanates |
| RU2007145914A (ru) * | 2006-12-13 | 2009-06-20 | Байер МатириальСайенс АГ (DE) | Способ получения изоцианатов |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3714439A1 (de) | 1987-04-30 | 1988-11-10 | Bayer Ag | Verfahren zur herstellung von (cyclo)aliphatischen diisocyanaten |
| DE4217019A1 (de) | 1992-05-22 | 1993-11-25 | Bayer Ag | Verfahren zur Herstellung von aromatischen Diisocyanaten |
| FR2723585B1 (fr) | 1994-08-12 | 1996-09-27 | Rhone Poulenc Chimie | Procede de preparation de composes du type polyisocyanates aromatiques en phase gazeuse. |
| DE19523385A1 (de) | 1995-06-23 | 1997-01-09 | Bayer Ag | Verfahren zur Herstellung von Triisocyanaten |
| DE10222023A1 (de) | 2002-05-17 | 2003-11-27 | Bayer Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| DE10235476A1 (de) | 2002-08-02 | 2004-02-12 | Basf Ag | Integriertes Verfahren zur Herstellung von Isocyanaten |
| DE10245704A1 (de) | 2002-09-30 | 2004-04-01 | Bayer Ag | Verfahren zum Quenchen eines gasförmigen Reaktionsgemisches bei der Gasphasenphosgenierung von Diaminen |
| DE10307141A1 (de) * | 2003-02-20 | 2004-09-02 | Bayer Ag | Verfahren zur Herstellung von (Poly)isocyanaten in der Gasphase |
| DE102005036870A1 (de) | 2005-08-02 | 2007-02-08 | Bayer Materialscience Ag | Verfahren zur Gasphasenphosgenierung |
| DE102005037328A1 (de) * | 2005-08-04 | 2007-02-08 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| US20070049482A1 (en) | 2005-08-11 | 2007-03-01 | Shin-Etsu Chemical Co., Ltd. | Synthetic quartz glass substrate for excimer lasers and making method |
| DE102005042392A1 (de) * | 2005-09-06 | 2007-03-08 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| CN101583594B (zh) | 2006-11-07 | 2013-06-19 | 巴斯夫欧洲公司 | 生产异氰酸酯的方法 |
| DE102006058634A1 (de) | 2006-12-13 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| ES2556964T3 (es) * | 2007-01-17 | 2016-01-21 | Basf Se | Procedimiento para la preparación de isocianatos |
| JP5595271B2 (ja) * | 2007-08-21 | 2014-09-24 | 萬華化学（寧波）有限公司 | フローダクトを備えるジェット式反応装置、及びフローダクトを備えるジェット式反応装置を用いたイソシアネート類製造方法 |
| US8558026B2 (en) * | 2007-08-30 | 2013-10-15 | Basf Se | Method for producing isocyanates |
| BRPI0816892A2 (pt) * | 2007-09-19 | 2015-03-24 | Basf Se | Processo para preparar diisocianatos |
-
2009
- 2009-07-09 DE DE102009032414A patent/DE102009032414A1/de not_active Withdrawn
-
2010
- 2010-06-26 US US13/382,609 patent/US8563767B2/en active Active
- 2010-06-26 KR KR1020127000445A patent/KR20120038436A/ko not_active Abandoned
- 2010-06-26 RU RU2012104325/04A patent/RU2543381C2/ru not_active IP Right Cessation
- 2010-06-26 WO PCT/EP2010/003915 patent/WO2011003531A1/de not_active Ceased
- 2010-06-26 IN IN244DEN2012 patent/IN2012DN00244A/en unknown
- 2010-06-26 HU HUE10729809A patent/HUE025762T2/en unknown
- 2010-06-26 CN CN201080031231.9A patent/CN102498092B/zh active Active
- 2010-06-26 EP EP10729809.3A patent/EP2451774B1/de active Active
- 2010-06-26 JP JP2012518791A patent/JP5717735B2/ja not_active Expired - Fee Related
- 2010-07-08 TW TW099122408A patent/TWI457315B/zh not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2007145914A (ru) * | 2006-12-13 | 2009-06-20 | Байер МатириальСайенс АГ (DE) | Способ получения изоцианатов |
| EP2060560A1 (en) * | 2007-11-14 | 2009-05-20 | Bayer MaterialScience AG | Preparation of light-colored isocyanates |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011003531A1 (de) | 2011-01-13 |
| EP2451774B1 (de) | 2015-07-22 |
| IN2012DN00244A (OSRAM) | 2015-08-21 |
| TWI457315B (zh) | 2014-10-21 |
| US8563767B2 (en) | 2013-10-22 |
| US20120302785A1 (en) | 2012-11-29 |
| HUE025762T2 (en) | 2016-05-30 |
| JP2012532159A (ja) | 2012-12-13 |
| CN102498092B (zh) | 2015-01-14 |
| DE102009032414A1 (de) | 2011-01-13 |
| CN102498092A (zh) | 2012-06-13 |
| KR20120038436A (ko) | 2012-04-23 |
| TW201116506A (en) | 2011-05-16 |
| JP5717735B2 (ja) | 2015-05-13 |
| EP2451774A1 (de) | 2012-05-16 |
| RU2012104325A (ru) | 2013-08-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20170627 |