RU2548361C2 - Способ получения изоцианатов в газовой фазе - Google Patents
Способ получения изоцианатов в газовой фазе Download PDFInfo
- Publication number
- RU2548361C2 RU2548361C2 RU2012105419/04A RU2012105419A RU2548361C2 RU 2548361 C2 RU2548361 C2 RU 2548361C2 RU 2012105419/04 A RU2012105419/04 A RU 2012105419/04A RU 2012105419 A RU2012105419 A RU 2012105419A RU 2548361 C2 RU2548361 C2 RU 2548361C2
- Authority
- RU
- Russia
- Prior art keywords
- reactor
- amine
- evaporated
- droplets
- gas
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 51
- 239000012948 isocyanate Substances 0.000 title claims abstract description 15
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 15
- 150000001412 amines Chemical class 0.000 claims abstract description 81
- 238000001704 evaporation Methods 0.000 claims abstract description 42
- 230000008020 evaporation Effects 0.000 claims abstract description 39
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 230000003993 interaction Effects 0.000 claims abstract description 11
- 150000003141 primary amines Chemical class 0.000 claims abstract description 8
- 239000007789 gas Substances 0.000 claims description 37
- 238000000926 separation method Methods 0.000 claims description 11
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 6
- 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 claims description 3
- 230000000737 periodic effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 40
- 150000004985 diamines Chemical class 0.000 description 34
- 239000012071 phase Substances 0.000 description 23
- 230000008569 process Effects 0.000 description 16
- 238000009835 boiling Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000013021 overheating Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- 230000000171 quenching effect Effects 0.000 description 7
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000010574 gas phase reaction Methods 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic amines Chemical class 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-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
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011555 saturated liquid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
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 |
|---|---|---|---|
| DE102009033639.7 | 2009-07-17 | ||
| DE102009033639A DE102009033639A1 (de) | 2009-07-17 | 2009-07-17 | Verfahen zur Herstellung von Isocyanaten in der Gasphase |
| PCT/EP2010/004109 WO2011006609A1 (de) | 2009-07-17 | 2010-07-06 | Verfahren zur herstellung von isocyanaten in der gasphase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012105419A RU2012105419A (ru) | 2013-08-27 |
| RU2548361C2 true RU2548361C2 (ru) | 2015-04-20 |
Family
ID=42985526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012105419/04A RU2548361C2 (ru) | 2009-07-17 | 2010-07-06 | Способ получения изоцианатов в газовой фазе |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9051243B2 (https=) |
| EP (1) | EP2454232B1 (https=) |
| JP (1) | JP2012533525A (https=) |
| KR (1) | KR20120038443A (https=) |
| CN (1) | CN102471242B (https=) |
| DE (1) | DE102009033639A1 (https=) |
| HU (1) | HUE035054T2 (https=) |
| RU (1) | RU2548361C2 (https=) |
| TW (1) | TW201109299A (https=) |
| WO (1) | WO2011006609A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105214568B (zh) * | 2014-06-10 | 2018-04-20 | 万华化学集团股份有限公司 | 一种加热器、该加热器的用途和应用该加热器制备异氰酸酯的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2004104739A (ru) * | 2003-02-20 | 2005-07-27 | Байер Акциенгезельшафт (De) | Способ получения диизоцианатов |
| EP1754698A2 (de) * | 2005-08-02 | 2007-02-21 | Bayer MaterialScience AG | Verfahren zur Gasphasenphosgenierung |
| EP1935876A1 (de) * | 2006-12-13 | 2008-06-25 | Bayer MaterialScience AG | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3714439A1 (de) | 1987-04-30 | 1988-11-10 | Bayer Ag | Verfahren zur herstellung von (cyclo)aliphatischen diisocyanaten |
| DE4217019A1 (de) | 1992-05-22 | 1993-11-25 | Bayer Ag | Verfahren zur Herstellung von aromatischen Diisocyanaten |
| FR2697017B1 (fr) | 1992-10-16 | 1995-01-06 | Rhone Poulenc Chimie | Procédé de préparation de composés du type isocyanates aromatiques en phase gazeuse. |
| DE19523385A1 (de) | 1995-06-23 | 1997-01-09 | Bayer Ag | Verfahren zur Herstellung von Triisocyanaten |
| DE10161384A1 (de) * | 2001-12-14 | 2003-06-18 | Bayer Ag | Verbessertes Verfahren für die Herstellung von (/Poly)-isocyanaten in der Gasphase |
| DE10245704A1 (de) | 2002-09-30 | 2004-04-01 | Bayer Ag | Verfahren zum Quenchen eines gasförmigen Reaktionsgemisches bei der Gasphasenphosgenierung von Diaminen |
| DE10335451A1 (de) | 2003-08-02 | 2005-03-10 | Bayer Materialscience Ag | Verfahren zur Entfernung von flüchtigen Verbindungen aus Stoffgemischen mittels Mikroverdampfer |
| HUE029625T2 (en) | 2006-11-07 | 2017-03-28 | Basf Se | Process for the preparation of isocyanates |
| DE102006058634A1 (de) | 2006-12-13 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| WO2010100221A1 (de) * | 2009-03-06 | 2010-09-10 | Basf Se | Verfahren und vorrichtung zur herstellung von isocyanaten |
-
2009
- 2009-07-17 DE DE102009033639A patent/DE102009033639A1/de not_active Withdrawn
-
2010
- 2010-07-06 RU RU2012105419/04A patent/RU2548361C2/ru not_active IP Right Cessation
- 2010-07-06 EP EP10735197.5A patent/EP2454232B1/de active Active
- 2010-07-06 JP JP2012519914A patent/JP2012533525A/ja active Pending
- 2010-07-06 WO PCT/EP2010/004109 patent/WO2011006609A1/de not_active Ceased
- 2010-07-06 HU HUE10735197A patent/HUE035054T2/en unknown
- 2010-07-06 CN CN201080033735.4A patent/CN102471242B/zh active Active
- 2010-07-06 KR KR1020127001176A patent/KR20120038443A/ko not_active Abandoned
- 2010-07-06 US US13/383,936 patent/US9051243B2/en active Active
- 2010-07-16 TW TW099123380A patent/TW201109299A/zh unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2004104739A (ru) * | 2003-02-20 | 2005-07-27 | Байер Акциенгезельшафт (De) | Способ получения диизоцианатов |
| EP1754698A2 (de) * | 2005-08-02 | 2007-02-21 | Bayer MaterialScience AG | Verfahren zur Gasphasenphosgenierung |
| EP1935876A1 (de) * | 2006-12-13 | 2008-06-25 | Bayer MaterialScience AG | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2454232A1 (de) | 2012-05-23 |
| EP2454232B1 (de) | 2017-06-14 |
| DE102009033639A1 (de) | 2011-01-20 |
| HUE035054T2 (en) | 2018-05-02 |
| WO2011006609A1 (de) | 2011-01-20 |
| US20120108845A1 (en) | 2012-05-03 |
| TW201109299A (en) | 2011-03-16 |
| KR20120038443A (ko) | 2012-04-23 |
| US9051243B2 (en) | 2015-06-09 |
| CN102471242B (zh) | 2015-09-16 |
| CN102471242A (zh) | 2012-05-23 |
| RU2012105419A (ru) | 2013-08-27 |
| JP2012533525A (ja) | 2012-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20170707 |