DE3212510A1 - Verfahren zur kontinuierlichen herstellung von organischen isocyanaten - Google Patents
Verfahren zur kontinuierlichen herstellung von organischen isocyanatenInfo
- Publication number
- DE3212510A1 DE3212510A1 DE3212510A DE3212510A DE3212510A1 DE 3212510 A1 DE3212510 A1 DE 3212510A1 DE 3212510 A DE3212510 A DE 3212510A DE 3212510 A DE3212510 A DE 3212510A DE 3212510 A1 DE3212510 A1 DE 3212510A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- phosgene
- amine
- organic
- pressure
- 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.)
- Granted
Links
- 239000012948 isocyanate Substances 0.000 title claims description 77
- 150000002513 isocyanates Chemical class 0.000 title claims description 77
- 238000000034 method Methods 0.000 title claims description 69
- 238000010924 continuous production Methods 0.000 title description 7
- 238000006243 chemical reaction Methods 0.000 claims description 185
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 92
- 150000001412 amines Chemical class 0.000 claims description 68
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
- 239000011541 reaction mixture Substances 0.000 claims description 22
- 239000006227 byproduct Substances 0.000 claims description 20
- 239000006185 dispersion Substances 0.000 claims description 18
- 238000000354 decomposition reaction Methods 0.000 claims description 17
- 150000003141 primary amines Chemical class 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000003134 recirculating effect Effects 0.000 claims description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 3
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 1
- 239000012295 chemical reaction liquid Substances 0.000 description 39
- 239000000243 solution Substances 0.000 description 32
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 30
- -1 amine hydrochloride Chemical class 0.000 description 18
- 238000004821 distillation Methods 0.000 description 17
- 239000007789 gas Substances 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 10
- 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 9
- 239000000126 substance Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000005086 pumping Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000000470 constituent Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000005001 aminoaryl group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-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
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 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
- 150000004992 toluidines Chemical class 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5121681A JPS57165358A (en) | 1981-04-07 | 1981-04-07 | Continuous preparaion of organic isocyanate |
| JP18373481A JPS59122451A (ja) | 1981-11-18 | 1981-11-18 | 有機イソシアナ−トの連続的製造法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE3212510A1 true DE3212510A1 (de) | 1982-11-11 |
| DE3212510C2 DE3212510C2 (US20100223739A1-20100909-C00025.png) | 1987-07-23 |
| DE3212510C3 DE3212510C3 (US20100223739A1-20100909-C00025.png) | 1990-03-08 |
Family
ID=26391751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3212510A Granted DE3212510A1 (de) | 1981-04-07 | 1982-04-03 | Verfahren zur kontinuierlichen herstellung von organischen isocyanaten |
Country Status (6)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19521800A1 (de) * | 1994-11-17 | 1996-05-23 | Bayer Ag | Verfahren zur Herstellung von Isocyanaten |
| EP2093215A1 (de) | 2008-02-19 | 2009-08-26 | Bayer MaterialScience AG | Verfahren zur Herstellung von Isocyanaten |
| US7584629B2 (en) | 2002-12-19 | 2009-09-08 | Basf Aktiengesellschaft | Separation of a substance mixture consisting of hydrogen chloride and phosgene |
| US7851648B2 (en) | 2002-12-19 | 2010-12-14 | Basf Aktiengesellschaft | Method for the continuous production of isocyanates |
| WO2017055311A1 (de) | 2015-09-30 | 2017-04-06 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3323882A1 (de) * | 1982-10-09 | 1984-04-12 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur kontinuierlichen heissphosgenierung von aminen |
| SK281459B6 (sk) * | 1994-11-17 | 2001-03-12 | Bayer Aktiengesellschaft | Spôsob jednostupňovej kontinuálnej prípravy izokyanatanov |
| DE4443642A1 (de) * | 1994-12-08 | 1996-06-13 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von organischen Isocyanaten |
| DE19827086A1 (de) * | 1998-06-18 | 1999-12-23 | Basf Ag | Verfahren zur Aufarbeitung von Destillationsrückständen aus der Synthese von Toluylendiisocyanat |
| JP4739798B2 (ja) * | 2005-04-05 | 2011-08-03 | 三井化学株式会社 | ポリイソシアネート連続製造装置 |
| US7504533B2 (en) * | 2006-04-24 | 2009-03-17 | Bayer Materialscience Llc | Process for the production of isocyanates |
| 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. |
| US9266824B2 (en) | 2014-01-13 | 2016-02-23 | Warsaw Orthopedic, Inc. | Methods and compositions for making an amino acid triisocyanate |
| CN103787920B (zh) * | 2014-02-18 | 2016-05-11 | 青岛科技大学 | 甲苯二异氰酸酯生产中紧急分解光气的方法 |
| WO2017001322A1 (de) | 2015-06-29 | 2017-01-05 | Covestro Deutschland Ag | Verfahren zur herstellung von polyisocyanaten |
| CN112480364A (zh) * | 2017-04-10 | 2021-03-12 | 三井化学株式会社 | 苯二甲撑二异氰酸酯组合物、苯二甲撑二异氰酸酯改性物组合物、二液型树脂原料及树脂 |
| JP6373536B1 (ja) | 2017-04-10 | 2018-08-15 | 三井化学株式会社 | キシリレンジイソシアネート組成物、キシリレンジイソシアネート変性体組成物、二液型樹脂原料および樹脂 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1206888B (de) * | 1959-08-11 | 1965-12-16 | Fmc Corp | Verfahren zur vorzugsweise kontinuierlichen Herstellung aromatischer Isocyanate |
| DE1263754B (de) * | 1964-08-19 | 1968-03-21 | Basf Ag | Verfahren zur Herstellung aromatischer Polyisocyanate |
| US3544612A (en) * | 1966-02-28 | 1970-12-01 | Toulousaine Prod Chim | Process for the production of organic isocyanates |
| DE1468445B2 (US20100223739A1-20100909-C00025.png) * | 1963-07-29 | 1974-07-04 | Olin Corp., New York, N.Y. (V.St.A.) | |
| DE2624285A1 (de) * | 1976-05-31 | 1977-12-22 | Basf Ag | Verfahren zur kontinuierlichen herstellung von organischen isocyanaten |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184494A (en) * | 1965-05-18 | Process for producing organic isocyanates | ||
| US2822373A (en) * | 1958-02-04 | Amine | ||
| GB827376A (en) * | 1955-03-17 | 1960-02-03 | France Etat | Improvements in the manufacture of isocyanates |
| US3226410A (en) * | 1962-07-20 | 1965-12-28 | Fmc Corp | Continuous method of preparing aromatic isocyanates |
| US3234253A (en) * | 1962-09-06 | 1966-02-08 | Du Pont | Two-stage phosgenation process for preparing aromatic isocyanates |
| DE1593588C3 (de) * | 1965-09-06 | 1974-05-22 | Takeda Chemical Industries Ltd., Osaka (Japan) | Verfahren zur Herstellung von m- und p-Xylylendiisocyanat |
| FR1469105A (fr) * | 1965-12-27 | 1967-02-10 | Toulousaine De Prod Chim Toloc | Procédé de fabrication d'esters isocyaniques |
-
1982
- 1982-04-02 US US06/364,894 patent/US4422976A/en not_active Expired - Lifetime
- 1982-04-03 DE DE3212510A patent/DE3212510A1/de active Granted
- 1982-04-06 BR BR8201971A patent/BR8201971A/pt not_active IP Right Cessation
- 1982-04-06 MX MX192184A patent/MX156500A/es unknown
- 1982-04-07 GB GB8210299A patent/GB2097789B/en not_active Expired
- 1982-04-07 FR FR8206087A patent/FR2503146B1/fr not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1206888B (de) * | 1959-08-11 | 1965-12-16 | Fmc Corp | Verfahren zur vorzugsweise kontinuierlichen Herstellung aromatischer Isocyanate |
| DE1468445B2 (US20100223739A1-20100909-C00025.png) * | 1963-07-29 | 1974-07-04 | Olin Corp., New York, N.Y. (V.St.A.) | |
| DE1263754B (de) * | 1964-08-19 | 1968-03-21 | Basf Ag | Verfahren zur Herstellung aromatischer Polyisocyanate |
| US3544612A (en) * | 1966-02-28 | 1970-12-01 | Toulousaine Prod Chim | Process for the production of organic isocyanates |
| DE2624285A1 (de) * | 1976-05-31 | 1977-12-22 | Basf Ag | Verfahren zur kontinuierlichen herstellung von organischen isocyanaten |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19521800A1 (de) * | 1994-11-17 | 1996-05-23 | Bayer Ag | Verfahren zur Herstellung von Isocyanaten |
| DE19521800C2 (de) * | 1994-11-17 | 1998-07-02 | Bayer Ag | Verfahren zur Herstellung von Isocyanaten |
| US7584629B2 (en) | 2002-12-19 | 2009-09-08 | Basf Aktiengesellschaft | Separation of a substance mixture consisting of hydrogen chloride and phosgene |
| US7851648B2 (en) | 2002-12-19 | 2010-12-14 | Basf Aktiengesellschaft | Method for the continuous production of isocyanates |
| EP2093215A1 (de) | 2008-02-19 | 2009-08-26 | Bayer MaterialScience AG | Verfahren zur Herstellung von Isocyanaten |
| DE102008009761A1 (de) | 2008-02-19 | 2009-08-27 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten |
| WO2017055311A1 (de) | 2015-09-30 | 2017-04-06 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
Also Published As
| Publication number | Publication date |
|---|---|
| MX156500A (es) | 1988-09-02 |
| BR8201971A (pt) | 1983-03-08 |
| FR2503146A1 (fr) | 1982-10-08 |
| GB2097789A (en) | 1982-11-10 |
| US4422976A (en) | 1983-12-27 |
| GB2097789B (en) | 1985-03-27 |
| DE3212510C2 (US20100223739A1-20100909-C00025.png) | 1987-07-23 |
| DE3212510C3 (US20100223739A1-20100909-C00025.png) | 1990-03-08 |
| FR2503146B1 (fr) | 1985-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8366 | Restricted maintained after opposition proceedings | ||
| 8305 | Restricted maintenance of patent after opposition | ||
| D4 | Patent maintained restricted | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: MITSUI CHEMICALS, INC., TOKIO/TOKYO, JP |
|
| 8339 | Ceased/non-payment of the annual fee |