DE1768439C3 - Verfahren zur fortlaufenden Herstellung organischer Isocyanate - Google Patents
Verfahren zur fortlaufenden Herstellung organischer IsocyanateInfo
- Publication number
- DE1768439C3 DE1768439C3 DE1768439A DE1768439A DE1768439C3 DE 1768439 C3 DE1768439 C3 DE 1768439C3 DE 1768439 A DE1768439 A DE 1768439A DE 1768439 A DE1768439 A DE 1768439A DE 1768439 C3 DE1768439 C3 DE 1768439C3
- Authority
- DE
- Germany
- Prior art keywords
- phosgene
- reactor
- reaction
- temperature
- preheated
- 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.)
- Expired
Links
- 239000012948 isocyanate Substances 0.000 title claims description 15
- 150000002513 isocyanates Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 7
- 238000010924 continuous production Methods 0.000 title claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- -1 hydrochloric acid amines Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 235000013877 carbamide Nutrition 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 150000003672 ureas Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical class NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims 1
- 230000009615 deamination Effects 0.000 claims 1
- 238000006481 deamination reaction Methods 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 238000007086 side reaction Methods 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 29
- 238000010438 heat treatment Methods 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-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
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZWUBBMDHSZDNTA-UHFFFAOYSA-N 4-Chloro-meta-phenylenediamine Chemical compound NC1=CC=C(Cl)C(N)=C1 ZWUBBMDHSZDNTA-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
- WBHYNFYDSXSSBU-UHFFFAOYSA-N Cl[ClH]C(Cl)=O Chemical compound Cl[ClH]C(Cl)=O WBHYNFYDSXSSBU-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- VKIRRGRTJUUZHS-IZLXSQMJSA-N N[C@H]1CC[C@H](N)CC1 Chemical compound N[C@H]1CC[C@H](N)CC1 VKIRRGRTJUUZHS-IZLXSQMJSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-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
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- VWPHTOATEPXMCB-UHFFFAOYSA-N carbamoyl chloride;hydrochloride Chemical group Cl.NC(Cl)=O VWPHTOATEPXMCB-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 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 1
- 230000007704 transition Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE711392D BE711392A (cg-RX-API-DMAC7.html) | 1968-02-28 | 1968-02-28 | |
| GB01391/68A GB1173890A (en) | 1968-02-28 | 1968-03-08 | Process for the Production of Organic Isocyanates |
| FR142916A FR1578808A (fr) | 1968-02-28 | 1968-03-08 | Procede de preparation d'isocyanates organiques |
| DD13151368A DD68502A (de) | 1968-02-28 | 1968-04-15 | Verfahren zur kontinuierlichen Herstellung organischer Isozyanate |
| DE1768439A DE1768439C3 (de) | 1968-02-28 | 1968-05-14 | Verfahren zur fortlaufenden Herstellung organischer Isocyanate |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE711392 | 1968-02-28 | ||
| GB01391/68A GB1173890A (en) | 1968-02-28 | 1968-03-08 | Process for the Production of Organic Isocyanates |
| FR142916A FR1578808A (fr) | 1968-02-28 | 1968-03-08 | Procede de preparation d'isocyanates organiques |
| DD13151368A DD68502A (de) | 1968-02-28 | 1968-04-15 | Verfahren zur kontinuierlichen Herstellung organischer Isozyanate |
| DE1768439A DE1768439C3 (de) | 1968-02-28 | 1968-05-14 | Verfahren zur fortlaufenden Herstellung organischer Isocyanate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1768439A1 DE1768439A1 (de) | 1971-11-18 |
| DE1768439B2 DE1768439B2 (cg-RX-API-DMAC7.html) | 1974-04-25 |
| DE1768439C3 true DE1768439C3 (de) | 1975-01-02 |
Family
ID=3852454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1768439A Expired DE1768439C3 (de) | 1968-02-28 | 1968-05-14 | Verfahren zur fortlaufenden Herstellung organischer Isocyanate |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE711392A (cg-RX-API-DMAC7.html) |
| DD (1) | DD68502A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1768439C3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR1578808A (cg-RX-API-DMAC7.html) |
| GB (1) | GB1173890A (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4419295A (en) | 1981-05-27 | 1983-12-06 | Bayer Aktiengesellschaft | Continuous process for the production of organic isocyanates |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2560596B1 (fr) * | 1984-03-02 | 1986-09-26 | Atochem | Diisocyanates-1,10 decane et leur procedes de fabrication |
| DE4412327A1 (de) * | 1994-04-11 | 1995-10-12 | Bayer Ag | Verfahren zur Herstellung von Diisocyanaten |
| DE19651041A1 (de) * | 1996-12-09 | 1998-06-10 | Bayer Ag | Verfahren zur Herstellung von Isocyanaten aus schwerlöslichen primären Aminen |
| DE10222968A1 (de) | 2002-05-23 | 2003-12-04 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| EP1371633A1 (en) * | 2002-06-14 | 2003-12-17 | Bayer Ag | Process for the purification of mixtures of toluenediisocyanate incorporating a dividing-wall distillation column |
| DE10260082A1 (de) | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Isocyanaten |
| DE10261187A1 (de) * | 2002-12-20 | 2004-07-08 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| RU2258724C2 (ru) * | 2003-10-08 | 2005-08-20 | Зао "Нтц-Камтэкс" | Способ получения 4,4`,4"-трифенилметантриизоционата из лейкопарафуксина, полученного восстановлением парафуксина |
| US20070232827A1 (en) * | 2004-05-25 | 2007-10-04 | Basf Aktiengesellschaft | Isocyanate Production Method |
| DE102004032871A1 (de) | 2004-07-07 | 2006-02-09 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyisocyanaten durch adiabate Phosgenierung von primären Aminen |
| US7547801B2 (en) | 2006-06-26 | 2009-06-16 | Bayer Materialscience Llc | Process for the continuous preparation of isocyanates |
| CN101528678B (zh) * | 2006-10-26 | 2014-03-19 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| FR2940283B1 (fr) | 2008-12-18 | 2011-03-11 | Perstorp Tolonates France | Utilisation d'un reacteur de type piston pour la mise en oeuvre d'un procede de phosgenation. |
| CN101429139B (zh) * | 2008-12-18 | 2012-11-14 | 宁波万华聚氨酯有限公司 | 二环己基甲烷二异氰酸酯及其中间体的制备方法 |
| CN101735109B (zh) * | 2009-12-04 | 2013-02-27 | 赛鼎工程有限公司 | 有机异氰酸酯的连续生产方法 |
| HUE045911T2 (hu) | 2015-06-29 | 2020-01-28 | Covestro Deutschland Ag | Eljárás poliizocianátok elõállítására |
| JP6743068B2 (ja) | 2015-06-29 | 2020-08-19 | 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 | 化学反応用塩化水素製造方法 |
| CN106946741B (zh) * | 2017-04-26 | 2018-12-07 | 万华化学集团股份有限公司 | 一种二环己基甲烷二异氰酸酯的制备方法 |
| 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 |
| US10875827B2 (en) | 2018-11-13 | 2020-12-29 | Covestro Deutschland Ag | Process for preparing an isocyanate by partly adiabatic phosgenation of the corresponding amine |
| CN111138320A (zh) * | 2019-12-19 | 2020-05-12 | 常州市恒邦化工有限公司 | 一种三苯甲烷-4.4’.4’’-三异氰酸酯胶粘剂的制备方法 |
| CN110981754A (zh) * | 2019-12-19 | 2020-04-10 | 山东华阳农药化工集团有限公司 | 一种二苯基乙烷二异氰酸酯及其制备方法 |
| WO2021228977A1 (de) | 2020-05-15 | 2021-11-18 | Covestro Deutschland Ag | Verfahren zum betreiben einer anlage zur kontinuierlichen herstellung eines isocyanats |
| CN115043758B (zh) * | 2022-07-06 | 2023-10-27 | 摩珈(上海)生物科技有限公司 | 超临界光气化法结合管道化法制备异氰酸酯的方法 |
| CN115108942B (zh) * | 2022-07-06 | 2023-10-27 | 摩珈(上海)生物科技有限公司 | 超临界光气化反应制备异氰酸酯的方法 |
-
1968
- 1968-02-28 BE BE711392D patent/BE711392A/fr not_active IP Right Cessation
- 1968-03-08 GB GB01391/68A patent/GB1173890A/en not_active Expired
- 1968-03-08 FR FR142916A patent/FR1578808A/fr not_active Expired
- 1968-04-15 DD DD13151368A patent/DD68502A/xx unknown
- 1968-05-14 DE DE1768439A patent/DE1768439C3/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4419295A (en) | 1981-05-27 | 1983-12-06 | Bayer Aktiengesellschaft | Continuous process for the production of organic isocyanates |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1578808A (fr) | 1969-08-22 |
| DE1768439B2 (cg-RX-API-DMAC7.html) | 1974-04-25 |
| GB1173890A (en) | 1969-12-10 |
| BE711392A (cg-RX-API-DMAC7.html) | 1968-07-01 |
| DD68502A (de) | 1969-08-20 |
| DE1768439A1 (de) | 1971-11-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |