TWI471295B - 製備異氰酸酯之方法 - Google Patents
製備異氰酸酯之方法 Download PDFInfo
- Publication number
- TWI471295B TWI471295B TW99122407A TW99122407A TWI471295B TW I471295 B TWI471295 B TW I471295B TW 99122407 A TW99122407 A TW 99122407A TW 99122407 A TW99122407 A TW 99122407A TW I471295 B TWI471295 B TW I471295B
- Authority
- TW
- Taiwan
- Prior art keywords
- phosgene
- gas
- hcl
- weight
- pressure
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 153
- 230000008569 process Effects 0.000 title claims description 56
- 239000012948 isocyanate Substances 0.000 title claims description 42
- 150000002513 isocyanates Chemical class 0.000 title claims description 42
- 238000002360 preparation method Methods 0.000 title claims description 12
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 444
- 239000007788 liquid Substances 0.000 claims description 127
- 238000006243 chemical reaction Methods 0.000 claims description 81
- 150000001412 amines Chemical class 0.000 claims description 26
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 239000007789 gas Substances 0.000 description 317
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 159
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 159
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 159
- 238000010521 absorption reaction Methods 0.000 description 72
- 238000004519 manufacturing process Methods 0.000 description 62
- 239000000203 mixture Substances 0.000 description 60
- 239000002904 solvent Substances 0.000 description 56
- 239000011261 inert gas Substances 0.000 description 42
- 239000012071 phase Substances 0.000 description 35
- 238000004821 distillation Methods 0.000 description 33
- 238000000926 separation method Methods 0.000 description 32
- 238000009833 condensation Methods 0.000 description 30
- 230000005494 condensation Effects 0.000 description 30
- 238000002156 mixing Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- 239000006227 byproduct Substances 0.000 description 19
- 238000001816 cooling Methods 0.000 description 19
- 238000005406 washing Methods 0.000 description 18
- 238000011084 recovery Methods 0.000 description 17
- 239000000945 filler Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 230000008719 thickening Effects 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 238000010791 quenching Methods 0.000 description 12
- 230000000171 quenching effect Effects 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000002706 hydrostatic effect Effects 0.000 description 5
- 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 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000003795 desorption Methods 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 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 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 amine hydrochloride Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-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
- UBDZFAGVPPMTIT-UHFFFAOYSA-N 2-aminoguanidine;hydron;chloride Chemical compound [Cl-].NC(N)=N[NH3+] UBDZFAGVPPMTIT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NHYCGSASNAIGLD-UHFFFAOYSA-N chlorine monoxide Inorganic materials Cl[O] NHYCGSASNAIGLD-UHFFFAOYSA-N 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- LADVLFVCTCHOAI-UHFFFAOYSA-N isocyanic acid;toluene Chemical compound N=C=O.CC1=CC=CC=C1 LADVLFVCTCHOAI-UHFFFAOYSA-N 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000002244 precipitate Substances 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
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000004998 toluenediamines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/80—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009032413A DE102009032413A1 (de) | 2009-07-09 | 2009-07-09 | Verfahren zur Herstellung von Isocyanaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201125839A TW201125839A (en) | 2011-08-01 |
| TWI471295B true TWI471295B (zh) | 2015-02-01 |
Family
ID=42342647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW99122407A TWI471295B (zh) | 2009-07-09 | 2010-07-08 | 製備異氰酸酯之方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8563768B2 (enExample) |
| EP (1) | EP2451775B1 (enExample) |
| JP (1) | JP5815517B2 (enExample) |
| KR (1) | KR20120038435A (enExample) |
| CN (1) | CN102498093B (enExample) |
| DE (1) | DE102009032413A1 (enExample) |
| HU (1) | HUE037835T2 (enExample) |
| RU (1) | RU2546125C9 (enExample) |
| TW (1) | TWI471295B (enExample) |
| WO (1) | WO2011003532A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8969615B2 (en) | 2011-03-31 | 2015-03-03 | Basf Se | Process for preparing isocyanates |
| 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 |
| US9932299B2 (en) | 2013-02-08 | 2018-04-03 | Covestro Deutschland Ag | Process for separating an isocyanate prepared by phosgenation of a primary amine in the gas phase from the gaseous crude product of the phosgenation |
| EP2829533A1 (de) | 2013-07-26 | 2015-01-28 | Bayer MaterialScience AG | Verfahren zur herstellung von isocyanaten |
| WO2015144681A1 (de) | 2014-03-27 | 2015-10-01 | Bayer Material Science Ag | Verfahren zum betreiben einer gasphasenphosgenierungsanlage |
| CN106458864B (zh) * | 2014-03-27 | 2020-08-11 | 科思创德国股份有限公司 | 运行气相光气化装置的方法 |
| EP3160630B1 (de) * | 2014-06-24 | 2022-08-31 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung von chemischen produkten mit betriebsunterbrechungen |
| PT3313815T (pt) | 2015-06-29 | 2019-10-17 | Covestro Deutschland Ag | Método de preparação de cloreto de hidrogénio para reações químicas |
| WO2017009311A1 (de) | 2015-07-16 | 2017-01-19 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
| CN108348889B (zh) * | 2015-09-24 | 2020-09-15 | 科思创德国股份有限公司 | 制备异氰酸酯的方法 |
| JP6913083B2 (ja) | 2015-09-30 | 2021-08-04 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | イソシアネートの製造方法 |
| JP6952026B2 (ja) * | 2015-10-16 | 2021-10-20 | ハンツマン・インターナショナル・エルエルシー | イソシアネート製造プロセスの制御方法 |
| WO2018184980A1 (de) | 2017-04-03 | 2018-10-11 | Covestro Deutschland Ag | Reinigungsvorrichtung für gasströme aus der isocyanatherstellung |
| WO2018224530A1 (de) | 2017-06-08 | 2018-12-13 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
| EP3634947B1 (de) | 2017-06-08 | 2022-09-07 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung von isocyanaten in der gasphase |
| CN109748822B (zh) * | 2017-11-08 | 2022-01-07 | 万华化学集团股份有限公司 | 一种制备异氰酸酯单体的方法和系统 |
| EP3524591A1 (en) | 2018-02-13 | 2019-08-14 | Covestro Deutschland AG | Process for the preparation of isocyanates |
| KR102437607B1 (ko) * | 2018-06-18 | 2022-08-26 | 한화솔루션 주식회사 | 지방족 이소시아네이트의 제조방법 |
| US10626084B2 (en) * | 2018-08-03 | 2020-04-21 | Covestro Llc | Method for producing two isocyanates |
| CN109761855B (zh) * | 2018-12-20 | 2020-07-28 | 万华化学集团股份有限公司 | 一种制备异佛尔酮二异氰酸酯的方法 |
| WO2020132936A1 (zh) | 2018-12-26 | 2020-07-02 | 万华化学集团股份有限公司 | 一种在气相中制备异氰酸酯的方法 |
| CN109704993A (zh) * | 2018-12-26 | 2019-05-03 | 万华化学集团股份有限公司 | 一种在气相中制备异氰酸酯的方法 |
| KR102839457B1 (ko) * | 2020-12-30 | 2025-07-25 | 한화솔루션 주식회사 | 이소시아네이트 화합물의 제조 방법 |
| KR102839456B1 (ko) * | 2020-12-30 | 2025-07-25 | 한화솔루션 주식회사 | 이소시아네이트 화합물의 제조 방법 |
| CN112724045B (zh) * | 2021-01-05 | 2022-01-28 | 安徽东至广信农化有限公司 | 一种制备二异氰酸酯的方法及其装置 |
| JP2025505400A (ja) * | 2022-01-26 | 2025-02-26 | ハンワ ソリューションズ コーポレイション | 回分式反応装置および脂肪族イソシアネートの製造方法 |
| WO2025036923A1 (de) | 2023-08-15 | 2025-02-20 | Covestro Deutschland Ag | Herstellung eines isocyanats im wege einer gasphasenreaktion in mehreren parallel betriebenen gasphasenreaktionsanordnungen |
| EP4653418A1 (de) | 2024-05-22 | 2025-11-26 | Covestro Deutschland AG | Verfahren zur herstellung von organischem isocyanat mit verbesserter nachhaltigkeit |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7504533B2 (en) * | 2006-04-24 | 2009-03-17 | Bayer Materialscience Llc | Process for the production of isocyanates |
| WO2009037179A1 (de) * | 2007-09-19 | 2009-03-26 | Basf Se | Verfahren zur herstellung von isocyanaten |
| US20090149672A1 (en) * | 2007-11-22 | 2009-06-11 | Fritz Pohl | Process for the production of aromatic discocyanates in the gas |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2764607A (en) | 1952-07-26 | 1956-09-25 | Celanese Corp | Recovery of phosgene in the production of chloroformates |
| GB737442A (en) | 1952-12-19 | 1955-09-28 | Bayer Ag | Recovery of phosgene |
| US3381025A (en) * | 1964-06-29 | 1968-04-30 | Hodogaya Chemical Co Ltd | Process for preparing isocyanates |
| GB1165831A (en) | 1967-01-26 | 1969-10-01 | Ici Ltd | Process for the Production of Isocyanates and Carbamyl Chlorides |
| 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 |
| 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 |
| DE10245704A1 (de) | 2002-09-30 | 2004-04-01 | Bayer Ag | Verfahren zum Quenchen eines gasförmigen Reaktionsgemisches bei der Gasphasenphosgenierung von Diaminen |
| DE10260084A1 (de) | 2002-12-19 | 2004-07-01 | Basf Ag | Auftrennung eines Stoffgemisches aus Clorwasserstoff und Phosgen |
| DE10349504A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| DE10359627A1 (de) | 2003-12-18 | 2005-07-21 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diisocyanaten |
| 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 |
| DE102006058634A1 (de) | 2006-12-13 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| CN101622226B (zh) | 2007-01-17 | 2013-07-10 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| EP2028178A1 (de) | 2007-08-22 | 2009-02-25 | Bayer MaterialScience AG | Herstellung von Isocyanaten mit niedrigen Chlorgehalten |
| CN101348252A (zh) * | 2008-04-25 | 2009-01-21 | 甘肃银光化学工业集团有限公司 | 甲苯二异氰酸酯生产工艺中光气的回收方法 |
-
2009
- 2009-07-09 DE DE102009032413A patent/DE102009032413A1/de not_active Withdrawn
-
2010
- 2010-06-26 RU RU2012104324/04A patent/RU2546125C9/ru not_active IP Right Cessation
- 2010-06-26 EP EP10730368.7A patent/EP2451775B1/de active Active
- 2010-06-26 US US13/382,615 patent/US8563768B2/en active Active
- 2010-06-26 CN CN201080031232.3A patent/CN102498093B/zh active Active
- 2010-06-26 WO PCT/EP2010/003916 patent/WO2011003532A1/de not_active Ceased
- 2010-06-26 KR KR1020127000444A patent/KR20120038435A/ko not_active Abandoned
- 2010-06-26 HU HUE10730368A patent/HUE037835T2/hu unknown
- 2010-06-26 JP JP2012518792A patent/JP5815517B2/ja not_active Expired - Fee Related
- 2010-07-08 TW TW99122407A patent/TWI471295B/zh not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7504533B2 (en) * | 2006-04-24 | 2009-03-17 | Bayer Materialscience Llc | Process for the production of isocyanates |
| WO2009037179A1 (de) * | 2007-09-19 | 2009-03-26 | Basf Se | Verfahren zur herstellung von isocyanaten |
| US20090149672A1 (en) * | 2007-11-22 | 2009-06-11 | Fritz Pohl | Process for the production of aromatic discocyanates in the gas |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2546125C9 (ru) | 2015-12-20 |
| KR20120038435A (ko) | 2012-04-23 |
| TW201125839A (en) | 2011-08-01 |
| RU2546125C2 (ru) | 2015-04-10 |
| JP2012532160A (ja) | 2012-12-13 |
| JP5815517B2 (ja) | 2015-11-17 |
| US20120123152A1 (en) | 2012-05-17 |
| RU2012104324A (ru) | 2013-08-20 |
| CN102498093B (zh) | 2015-03-04 |
| HUE037835T2 (hu) | 2018-09-28 |
| US8563768B2 (en) | 2013-10-22 |
| EP2451775B1 (de) | 2018-05-30 |
| WO2011003532A1 (de) | 2011-01-13 |
| DE102009032413A1 (de) | 2011-01-13 |
| CN102498093A (zh) | 2012-06-13 |
| EP2451775A1 (de) | 2012-05-16 |
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| Date | Code | Title | Description |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |