KR102081402B1 - 기상 중 상응하는 아민의 포스겐화에 의한 이소시아네이트의 제조 방법 - Google Patents
기상 중 상응하는 아민의 포스겐화에 의한 이소시아네이트의 제조 방법 Download PDFInfo
- Publication number
- KR102081402B1 KR102081402B1 KR1020147017617A KR20147017617A KR102081402B1 KR 102081402 B1 KR102081402 B1 KR 102081402B1 KR 1020147017617 A KR1020147017617 A KR 1020147017617A KR 20147017617 A KR20147017617 A KR 20147017617A KR 102081402 B1 KR102081402 B1 KR 102081402B1
- Authority
- KR
- South Korea
- Prior art keywords
- fluidized bed
- amine
- phosgene
- bed reactor
- 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.)
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- 150000001412 amines Chemical class 0.000 title claims abstract description 51
- 239000012948 isocyanate Substances 0.000 title claims abstract description 16
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 27
- 239000007792 gaseous phase Substances 0.000 title 1
- 239000007789 gas Substances 0.000 claims abstract description 43
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000007787 solid Substances 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 20
- 239000012495 reaction gas Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 230000008016 vaporization Effects 0.000 claims description 12
- 239000012530 fluid Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000009834 vaporization Methods 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 15
- 239000012071 phase Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 8
- -1 amine hydrochloride Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 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
- 238000005243 fluidization Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-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
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-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
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-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
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 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
- 230000007423 decrease Effects 0.000 description 1
- 238000002474 experimental method Methods 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
- 230000002779 inactivation Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate 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
- 238000005507 spraying Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 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
- C07C263/10—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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11191097.2 | 2011-11-29 | ||
| EP11191097 | 2011-11-29 | ||
| PCT/EP2012/073809 WO2013079517A1 (de) | 2011-11-29 | 2012-11-28 | Verfahren zur herstellung von isocyanaten durch phosgenierung der entsprechenden amine in der gasphase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20140103997A KR20140103997A (ko) | 2014-08-27 |
| KR102081402B1 true KR102081402B1 (ko) | 2020-02-25 |
Family
ID=47278810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147017617A Active KR102081402B1 (ko) | 2011-11-29 | 2012-11-28 | 기상 중 상응하는 아민의 포스겐화에 의한 이소시아네이트의 제조 방법 |
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 |
| HUE027460T2 (en) | 2016-09-28 |
| PL2785684T3 (pl) | 2016-05-31 |
| KR20140103997A (ko) | 2014-08-27 |
| CN103958462A (zh) | 2014-07-30 |
| 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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