DE2112181A1 - Verfahren zur kontinuierlichen Herstellung von organischen Isocyanaten - Google Patents
Verfahren zur kontinuierlichen Herstellung von organischen IsocyanatenInfo
- Publication number
- DE2112181A1 DE2112181A1 DE19712112181 DE2112181A DE2112181A1 DE 2112181 A1 DE2112181 A1 DE 2112181A1 DE 19712112181 DE19712112181 DE 19712112181 DE 2112181 A DE2112181 A DE 2112181A DE 2112181 A1 DE2112181 A1 DE 2112181A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- liquid
- phosgene
- organic
- phase
- 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.)
- Withdrawn
Links
- 239000012948 isocyanate Substances 0.000 title claims description 23
- 150000002513 isocyanates Chemical class 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 21
- 238000010924 continuous production Methods 0.000 title claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 60
- 239000007789 gas Substances 0.000 claims description 35
- 239000011541 reaction mixture Substances 0.000 claims description 32
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 28
- 239000007788 liquid Substances 0.000 claims description 26
- 238000012856 packing Methods 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000012071 phase Substances 0.000 claims description 9
- 230000007704 transition Effects 0.000 claims description 9
- 239000007792 gaseous phase Substances 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 150000003141 primary amines Chemical class 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 7
- 239000011261 inert gas Substances 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 238000013021 overheating 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
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-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
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 1
- YYDRNPOEMZZTPM-UHFFFAOYSA-N 2,4,6-triaminotoluene Chemical compound CC1=C(N)C=C(N)C=C1N YYDRNPOEMZZTPM-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
- 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
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- ADUMIBSPEHFSLA-UHFFFAOYSA-N 4-[bis(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 ADUMIBSPEHFSLA-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
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- -1 amine hydrochloride Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000017525 heat dissipation Effects 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
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000010349 pulsation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000004575 stone Substances 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
- 150000003613 toluenes Chemical class 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes 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)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712112181 DE2112181A1 (de) | 1971-03-13 | 1971-03-13 | Verfahren zur kontinuierlichen Herstellung von organischen Isocyanaten |
| FR7208236A FR2129554A5 (en) | 1971-03-13 | 1972-03-09 | Continuous isocyanates prepn - from primary amines and phosgenes by recycling separated gas and liq phases |
| BE780513A BE780513A (fr) | 1971-03-13 | 1972-03-10 | Procede de preparation en continu d'isocyanates organiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712112181 DE2112181A1 (de) | 1971-03-13 | 1971-03-13 | Verfahren zur kontinuierlichen Herstellung von organischen Isocyanaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2112181A1 true DE2112181A1 (de) | 1972-10-05 |
| DE2112181B2 DE2112181B2 (enExample) | 1980-02-21 |
Family
ID=5801469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712112181 Withdrawn DE2112181A1 (de) | 1971-03-13 | 1971-03-13 | Verfahren zur kontinuierlichen Herstellung von organischen Isocyanaten |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE780513A (enExample) |
| DE (1) | DE2112181A1 (enExample) |
| FR (1) | FR2129554A5 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0716079A1 (de) * | 1994-12-08 | 1996-06-12 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von organischen Isocyanaten |
| WO2004026813A1 (de) * | 2002-08-20 | 2004-04-01 | Basf Aktiengesellschaft | Gasphasenphosgenierung bei moderaten drücken |
| US7112694B2 (en) | 2002-05-23 | 2006-09-26 | Basf Aktiengesellschaft | Method for producing isocyanates |
| US7851648B2 (en) | 2002-12-19 | 2010-12-14 | Basf Aktiengesellschaft | Method for the continuous production of isocyanates |
| US8546606B2 (en) | 2003-03-11 | 2013-10-01 | Basf Aktiengesellschaft | Method for producing polyisocyanates |
| WO2017001322A1 (de) * | 2015-06-29 | 2017-01-05 | Covestro Deutschland Ag | Verfahren zur herstellung von polyisocyanaten |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3736988C1 (de) * | 1987-10-31 | 1989-03-23 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von organischen Mono- und Polyisocyanaten |
-
1971
- 1971-03-13 DE DE19712112181 patent/DE2112181A1/de not_active Withdrawn
-
1972
- 1972-03-09 FR FR7208236A patent/FR2129554A5/fr not_active Expired
- 1972-03-10 BE BE780513A patent/BE780513A/xx unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0716079A1 (de) * | 1994-12-08 | 1996-06-12 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von organischen Isocyanaten |
| US7112694B2 (en) | 2002-05-23 | 2006-09-26 | Basf Aktiengesellschaft | Method for producing isocyanates |
| WO2004026813A1 (de) * | 2002-08-20 | 2004-04-01 | Basf Aktiengesellschaft | Gasphasenphosgenierung bei moderaten drücken |
| US7994361B2 (en) | 2002-08-20 | 2011-08-09 | Basf Aktiengesellschaft | Moderate-pressure gas phase phosgenation |
| US7851648B2 (en) | 2002-12-19 | 2010-12-14 | Basf Aktiengesellschaft | Method for the continuous production of isocyanates |
| US8546606B2 (en) | 2003-03-11 | 2013-10-01 | Basf Aktiengesellschaft | Method for producing polyisocyanates |
| WO2017001322A1 (de) * | 2015-06-29 | 2017-01-05 | Covestro Deutschland Ag | Verfahren zur herstellung von polyisocyanaten |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2112181B2 (enExample) | 1980-02-21 |
| BE780513A (fr) | 1972-09-11 |
| FR2129554A5 (en) | 1972-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8230 | Patent withdrawn |