PT1575905E - Processo para a separação de isocianatos a partir de uma mistura reactiva - Google Patents
Processo para a separação de isocianatos a partir de uma mistura reactiva Download PDFInfo
- Publication number
- PT1575905E PT1575905E PT03789263T PT03789263T PT1575905E PT 1575905 E PT1575905 E PT 1575905E PT 03789263 T PT03789263 T PT 03789263T PT 03789263 T PT03789263 T PT 03789263T PT 1575905 E PT1575905 E PT 1575905E
- Authority
- PT
- Portugal
- Prior art keywords
- column
- isocyanate
- process according
- mbar
- separation
- Prior art date
Links
- 239000012948 isocyanate Substances 0.000 title claims abstract description 59
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 57
- 239000011541 reaction mixture Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 22
- 238000000926 separation method Methods 0.000 claims abstract description 26
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 238000000746 purification Methods 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 23
- 238000009834 vaporization Methods 0.000 claims description 13
- 230000008016 vaporization Effects 0.000 claims description 13
- 239000006200 vaporizer Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 7
- 238000011144 upstream manufacturing Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 description 22
- 238000004821 distillation Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 238000009835 boiling Methods 0.000 description 12
- -1 polymethylene Polymers 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 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 7
- 239000006227 byproduct Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 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
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- JLVWYWVLMFVCDI-UHFFFAOYSA-N diethyl benzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(C(=O)OCC)=C1 JLVWYWVLMFVCDI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011273 tar residue Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000002699 waste material Substances 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
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
- C07C263/20—Separation; Purification
-
- 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
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10260093A DE10260093A1 (de) | 2002-12-19 | 2002-12-19 | Verfahren zur Abtrennung von Isocyanaten aus einem Reaktionsgemisch |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1575905E true PT1575905E (pt) | 2009-09-30 |
Family
ID=32404076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT03789263T PT1575905E (pt) | 2002-12-19 | 2003-12-13 | Processo para a separação de isocianatos a partir de uma mistura reactiva |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20060089507A1 (enExample) |
| EP (1) | EP1575905B1 (enExample) |
| JP (1) | JP4324559B2 (enExample) |
| KR (1) | KR101016737B1 (enExample) |
| CN (1) | CN1729166A (enExample) |
| AT (1) | ATE442350T1 (enExample) |
| AU (1) | AU2003293872A1 (enExample) |
| DE (2) | DE10260093A1 (enExample) |
| ES (1) | ES2330518T3 (enExample) |
| MX (1) | MXPA05006056A (enExample) |
| PT (1) | PT1575905E (enExample) |
| WO (1) | WO2004056757A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10333929A1 (de) * | 2003-07-25 | 2005-02-24 | Bayer Materialscience Ag | Herstellung von Mischungen von Di- und Polyisocyanaten der Diphenylmethanreihe mit hohen Gehalten an 4,4'-Methylendiphenyldiisocyanat und 2,4'-Methylendiphenyldiisocyanat |
| US8030522B2 (en) * | 2006-06-07 | 2011-10-04 | Bayer Materialscience Llc | Process for the production of toluene diisocyanate |
| WO2008055898A1 (de) * | 2006-11-07 | 2008-05-15 | Basf Se | Verfahren zur herstellung von isocyanaten |
| DE102007020444A1 (de) | 2007-04-27 | 2008-11-06 | Bayer Materialscience Ag | Verfahren zur Oxidation eines Chlorwasserstoffenthaltenden Gasgemisches |
| CN101790510B (zh) * | 2007-08-31 | 2013-07-24 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| CN102675154B (zh) * | 2011-03-11 | 2013-11-06 | 中国科学院过程工程研究所 | 一种氨基甲酸酯热解制备mdi复杂产物的分离精制装置及方法 |
| WO2013139703A1 (de) | 2012-03-19 | 2013-09-26 | Bayer Intellectual Property Gmbh | Verfahren zur herstellung von isocyanaten |
| CN103382167B (zh) * | 2013-05-16 | 2015-06-17 | 甘肃银光聚银化工有限公司 | 一种精制六亚甲基二异氰酸酯的装置和方法 |
| WO2015024859A1 (de) * | 2013-08-19 | 2015-02-26 | Bayer Materialscience Ag | Verfahren zur gewinnung von organischen isocyanaten aus destillationsrückständen der isocyanatherstellung |
| HUE060286T2 (hu) * | 2014-06-24 | 2023-02-28 | Covestro Intellectual Property Gmbh & Co Kg | Eljárás kémiai termékek elõállítására az eljárás megszakítása mellett |
| HUE051732T2 (hu) | 2016-10-10 | 2021-03-29 | Basf Se | Eljárás toluoldiamin (TDA) kátrány hidrogénezésére |
| WO2018114846A1 (de) | 2016-12-21 | 2018-06-28 | Covestro Deutschland Ag | Verfahren zur herstellung eines isocyanats |
| CN107652208B (zh) * | 2017-08-30 | 2020-06-02 | 万华化学（宁波）有限公司 | 一种从光气化反应得到的异氰酸酯产物中脱除溶剂的方法和装置 |
| EP4031526B1 (de) | 2019-09-17 | 2024-07-10 | Covestro Deutschland AG | Verfahren zur herstellung von isocyanaten |
| KR102839455B1 (ko) * | 2020-12-30 | 2025-07-25 | 한화솔루션 주식회사 | 이소시아네이트 화합물의 제조 방법 |
| KR102847664B1 (ko) * | 2021-11-30 | 2025-08-18 | 한화솔루션 주식회사 | 디이소시아네이트의 제조방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3140305A (en) * | 1962-12-17 | 1964-07-07 | Fmc Corp | Preparation of diisocyanates |
| US3410888A (en) * | 1965-05-18 | 1968-11-12 | Upjohn Co | Process for recovering aromatic diisocyanates |
| US3405040A (en) * | 1965-08-31 | 1968-10-08 | Mobay Chemical Corp | Method for recovering tolylene diisocyanate |
| CA998060A (en) * | 1970-05-22 | 1976-10-05 | Carl F. Irwin | Recovery of organic isocyanate |
| DE19528781A1 (de) * | 1995-08-04 | 1997-02-06 | Bayer Ag | Verfahren zur Herstellung von Toluylendiisocyanat, spezielle Gemische aus Toluylendiamin und Wasser und deren Verwendung zur Herstellung von Toluylendiisocyanat |
| DE19804915A1 (de) * | 1998-02-07 | 1999-08-12 | Basf Ag | Verfahren zur Herstellung von Methylendi(phenylamin) und Methylendi(phenylisocyanat) |
| DE19817691A1 (de) * | 1998-04-21 | 1999-10-28 | Basf Ag | Verfahren zur Herstellung von Mischungen aus Diphenylmehandiisocyanaten und Polyphenylen-polymethylen-polyisocyanaten mit vermindertem Gehalt an chlorierten Nebenprodukten und verminderter Jodfarbzahl |
| EP1371633A1 (en) * | 2002-06-14 | 2003-12-17 | Bayer Ag | Process for the purification of mixtures of toluenediisocyanate incorporating a dividing-wall distillation column |
-
2002
- 2002-12-19 DE DE10260093A patent/DE10260093A1/de not_active Withdrawn
-
2003
- 2003-12-13 JP JP2004561289A patent/JP4324559B2/ja not_active Expired - Fee Related
- 2003-12-13 CN CNA2003801067827A patent/CN1729166A/zh active Pending
- 2003-12-13 ES ES03789263T patent/ES2330518T3/es not_active Expired - Lifetime
- 2003-12-13 PT PT03789263T patent/PT1575905E/pt unknown
- 2003-12-13 EP EP03789263A patent/EP1575905B1/de not_active Expired - Lifetime
- 2003-12-13 AU AU2003293872A patent/AU2003293872A1/en not_active Abandoned
- 2003-12-13 MX MXPA05006056A patent/MXPA05006056A/es active IP Right Grant
- 2003-12-13 DE DE50311902T patent/DE50311902D1/de not_active Expired - Lifetime
- 2003-12-13 WO PCT/EP2003/014186 patent/WO2004056757A1/de not_active Ceased
- 2003-12-13 AT AT03789263T patent/ATE442350T1/de not_active IP Right Cessation
- 2003-12-13 KR KR1020057011102A patent/KR101016737B1/ko not_active Expired - Fee Related
- 2003-12-13 US US10/538,119 patent/US20060089507A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20060089507A1 (en) | 2006-04-27 |
| KR101016737B1 (ko) | 2011-02-25 |
| EP1575905A1 (de) | 2005-09-21 |
| AU2003293872A1 (en) | 2004-07-14 |
| DE10260093A1 (de) | 2004-07-01 |
| MXPA05006056A (es) | 2005-08-16 |
| EP1575905B1 (de) | 2009-09-09 |
| ES2330518T3 (es) | 2009-12-11 |
| DE50311902D1 (de) | 2009-10-22 |
| JP2006510693A (ja) | 2006-03-30 |
| CN1729166A (zh) | 2006-02-01 |
| JP4324559B2 (ja) | 2009-09-02 |
| WO2004056757A1 (de) | 2004-07-08 |
| KR20050089053A (ko) | 2005-09-07 |
| ATE442350T1 (de) | 2009-09-15 |
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