HUE027460T2 - Process for the preparation of isocyanates by gas phase phosgenesis of the corresponding amines - Google Patents
Process for the preparation of isocyanates by gas phase phosgenesis of the corresponding amines Download PDFInfo
- Publication number
- HUE027460T2 HUE027460T2 HUE12794938A HUE12794938A HUE027460T2 HU E027460 T2 HUE027460 T2 HU E027460T2 HU E12794938 A HUE12794938 A HU E12794938A HU E12794938 A HUE12794938 A HU E12794938A HU E027460 T2 HUE027460 T2 HU E027460T2
- Authority
- HU
- Hungary
- Prior art keywords
- amine
- phosgene
- stream
- gas
- bed reactor
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 title claims description 45
- 238000000034 method Methods 0.000 title claims description 28
- 239000012948 isocyanate Substances 0.000 title claims description 13
- 150000002513 isocyanates Chemical class 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000007792 gaseous phase Substances 0.000 title description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 32
- 239000007789 gas Substances 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000007787 solid Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 18
- 239000012530 fluid Substances 0.000 claims description 11
- 239000012495 reaction gas Substances 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 229910010272 inorganic material Inorganic materials 0.000 claims description 2
- 239000011147 inorganic material Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000011343 solid material Substances 0.000 claims 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 230000004907 flux Effects 0.000 claims 2
- 238000007711 solidification Methods 0.000 claims 2
- 230000008023 solidification Effects 0.000 claims 2
- BTQLWKNIJDKIAB-UHFFFAOYSA-N 6-methylidene-n-phenylcyclohexa-2,4-dien-1-amine Chemical compound C=C1C=CC=CC1NC1=CC=CC=C1 BTQLWKNIJDKIAB-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-AKLPVKDBSA-N Ammonia-N17 Chemical compound [17NH3] QGZKDVFQNNGYKY-AKLPVKDBSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000209504 Poaceae Species 0.000 claims 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000008929 regeneration Effects 0.000 claims 1
- 238000011069 regeneration method Methods 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 239000012071 phase Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 7
- 238000009834 vaporization Methods 0.000 description 7
- 230000008016 vaporization Effects 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 6
- -1 amine hydrochlorides Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 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
- 238000010327 methods by industry Methods 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000010099 solid forming Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003672 ureas Chemical class 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
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11191097 | 2011-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE027460T2 true HUE027460T2 (en) | 2016-09-28 |
Family
ID=47278810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE12794938A HUE027460T2 (en) | 2011-11-29 | 2012-11-28 | Process for the preparation of isocyanates by gas phase phosgenesis of the corresponding amines |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2785684B1 (enExample) |
| JP (1) | JP6072061B2 (enExample) |
| KR (1) | KR102081402B1 (enExample) |
| CN (1) | CN103958462B (enExample) |
| BR (1) | BR112014012679A8 (enExample) |
| ES (1) | ES2560408T3 (enExample) |
| HU (1) | HUE027460T2 (enExample) |
| IN (1) | IN2014CN04741A (enExample) |
| PL (1) | PL2785684T3 (enExample) |
| PT (1) | PT2785684E (enExample) |
| WO (1) | WO2013079517A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6810919B2 (ja) | 2014-04-11 | 2021-01-13 | 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 | 透明なポリチオウレタン体の製造のための芳香族ニトリルを含む組成物 |
| CN111825572B (zh) * | 2019-04-15 | 2023-01-13 | 万华化学集团股份有限公司 | 一种成盐-雾化光气化法制备异氰酸酯的方法 |
| HUE070927T2 (hu) | 2020-11-23 | 2025-07-28 | Basf Se | Eljárás izocianátok elõállítására |
| EP4347556A1 (en) | 2021-05-25 | 2024-04-10 | Basf Se | Process for preparing at least one polyisocyanate |
| CN117986159A (zh) * | 2022-11-01 | 2024-05-07 | 万华化学集团股份有限公司 | 一种气相光气化反应制备异氰酸酯的方法 |
| WO2025016900A1 (en) | 2023-07-14 | 2025-01-23 | Basf Se | Process for recycling polyurethane waste through remonomerization by hydro ammonolysis |
| WO2025016920A1 (en) | 2023-07-14 | 2025-01-23 | Basf Se | Process for autocatalytic hydroglycolytic or hydrolytic cleavage of waste streams containing polyurethane |
| WO2025016934A1 (en) | 2023-07-14 | 2025-01-23 | Basf Se | Recycling of pu-softfoams with graft polyol content |
| WO2025016903A1 (en) | 2023-07-14 | 2025-01-23 | Basf Se | Recovery of polyesterols from polyesterol-based polyurethanes via hydrolysis and re-condensation |
| WO2025016860A1 (en) | 2023-07-14 | 2025-01-23 | Basf Se | Process for recycling polyurethane foams |
| WO2025190721A1 (en) | 2024-03-13 | 2025-09-18 | Basf Se | Method for recycling a polymer material from a vehicle scrap material |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2915830A1 (de) * | 1979-04-19 | 1980-10-23 | Basf Ag | Gewinnung von toluylendiisocyanat und/oder hoehersiedenden loesungsmitteln im wirbelbett aus destillationsrueckstaenden der toluylendiisocanat-herstellung |
| DE3413174A1 (de) * | 1984-04-07 | 1985-10-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyisocyanaten |
| DE10026142A1 (de) * | 2000-05-26 | 2001-12-13 | Basf Ag | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von organischen Mono- oder Polyisocyanaten |
| AU2001227152A1 (en) * | 2000-11-14 | 2002-05-27 | Dsm N.V. | Fluidised bed reactor |
| DE10349504A1 (de) * | 2003-10-23 | 2005-05-25 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| JP5692964B2 (ja) * | 2006-01-13 | 2015-04-01 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | イソシアネートの製造法 |
| HUE025811T2 (en) * | 2006-07-13 | 2016-04-28 | Basf Se | Process for the preparation of isocyanates |
| KR20100075863A (ko) * | 2007-08-30 | 2010-07-05 | 바스프 에스이 | 이소시아네이트의 제조 방법 |
-
2012
- 2012-11-28 IN IN4741CHN2014 patent/IN2014CN04741A/en unknown
- 2012-11-28 BR BR112014012679A patent/BR112014012679A8/pt not_active Application Discontinuation
- 2012-11-28 ES ES12794938.6T patent/ES2560408T3/es active Active
- 2012-11-28 CN CN201280058840.2A patent/CN103958462B/zh active Active
- 2012-11-28 KR KR1020147017617A patent/KR102081402B1/ko active Active
- 2012-11-28 PT PT127949386T patent/PT2785684E/pt unknown
- 2012-11-28 EP EP12794938.6A patent/EP2785684B1/de active Active
- 2012-11-28 WO PCT/EP2012/073809 patent/WO2013079517A1/de not_active Ceased
- 2012-11-28 PL PL12794938T patent/PL2785684T3/pl unknown
- 2012-11-28 JP JP2014542889A patent/JP6072061B2/ja not_active Expired - Fee Related
- 2012-11-28 HU HUE12794938A patent/HUE027460T2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2785684B1 (de) | 2015-11-18 |
| EP2785684A1 (de) | 2014-10-08 |
| BR112014012679A8 (pt) | 2017-06-20 |
| PL2785684T3 (pl) | 2016-05-31 |
| KR20140103997A (ko) | 2014-08-27 |
| CN103958462A (zh) | 2014-07-30 |
| KR102081402B1 (ko) | 2020-02-25 |
| IN2014CN04741A (enExample) | 2015-09-18 |
| BR112014012679A2 (pt) | 2017-06-13 |
| JP2015501806A (ja) | 2015-01-19 |
| WO2013079517A1 (de) | 2013-06-06 |
| PT2785684E (pt) | 2016-03-23 |
| ES2560408T3 (es) | 2016-02-18 |
| CN103958462B (zh) | 2016-10-19 |
| JP6072061B2 (ja) | 2017-02-01 |
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