JP5398714B2 - イソシアネートの製造方法 - Google Patents
イソシアネートの製造方法 Download PDFInfo
- Publication number
- JP5398714B2 JP5398714B2 JP2010522352A JP2010522352A JP5398714B2 JP 5398714 B2 JP5398714 B2 JP 5398714B2 JP 2010522352 A JP2010522352 A JP 2010522352A JP 2010522352 A JP2010522352 A JP 2010522352A JP 5398714 B2 JP5398714 B2 JP 5398714B2
- Authority
- JP
- Japan
- Prior art keywords
- evaporator
- tdi
- polyisocyanate
- spiral tube
- diisocyanate
- 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 - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 239000012948 isocyanate Substances 0.000 title description 26
- 150000002513 isocyanates Chemical class 0.000 title description 26
- 238000000034 method Methods 0.000 claims description 46
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 11
- 239000005056 polyisocyanate Substances 0.000 claims description 10
- 229920001228 polyisocyanate Polymers 0.000 claims description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 30
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- 238000011144 upstream manufacturing Methods 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
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 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
- 239000012084 conversion product Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000004094 preconcentration Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000005514 two-phase flow Effects 0.000 description 1
- 238000010626 work up procedure 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
-
- 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
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 |
|---|---|---|---|
| EP07115380.3 | 2007-08-31 | ||
| EP07115380 | 2007-08-31 | ||
| PCT/EP2008/061188 WO2009027418A1 (de) | 2007-08-31 | 2008-08-27 | Verfahren zur herstellung von isocyanaten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010536928A JP2010536928A (ja) | 2010-12-02 |
| JP2010536928A5 JP2010536928A5 (enExample) | 2011-10-13 |
| JP5398714B2 true JP5398714B2 (ja) | 2014-01-29 |
Family
ID=40090056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010522352A Expired - Fee Related JP5398714B2 (ja) | 2007-08-31 | 2008-08-27 | イソシアネートの製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8273915B2 (enExample) |
| EP (1) | EP2197836B1 (enExample) |
| JP (1) | JP5398714B2 (enExample) |
| KR (1) | KR101578565B1 (enExample) |
| CN (1) | CN101790510B (enExample) |
| MX (1) | MX2010001396A (enExample) |
| WO (1) | WO2009027418A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100810828B1 (ko) * | 2006-03-17 | 2008-03-06 | 와이케이케이 가부시끼가이샤 | 정음 면파스너 |
| KR101756998B1 (ko) | 2009-04-24 | 2017-07-26 | 바스프 에스이 | 색 안정성 ｍｄａ 및 ｍｄｉ의 제조 방법 |
| EP2446247B1 (de) | 2009-06-24 | 2013-05-01 | Basf Se | Verfahren zur erfassung von wassereintritten in phosgenführenden anlagen |
| EP2445869B1 (en) | 2009-06-26 | 2014-12-24 | Basf Se | Process for the production of isocyanates, preferably diisocyanates and polyisocyanates with solvent recirculation |
| CN102471241B (zh) | 2009-07-14 | 2015-11-25 | 巴斯夫欧洲公司 | 制备二苯甲烷系列的浅色异氰酸酯的方法 |
| JP2012532918A (ja) | 2009-07-16 | 2012-12-20 | ビーエーエスエフ ソシエタス・ヨーロピア | ジフェニルメタンジイソシアネート類の明色イソシアネートの製造方法 |
| IN2014DN07241A (enExample) * | 2012-03-19 | 2015-04-24 | Bayer Ip Gmbh | |
| CN113444022B (zh) * | 2020-03-24 | 2022-11-08 | 万华化学（宁波）有限公司 | 一种制备低色号长保质期耐低温的mdi-50的方法 |
| CN111961185B (zh) * | 2020-08-27 | 2022-07-12 | 万华化学集团股份有限公司 | 一种多亚甲基多苯基多异氰酸酯组合物及其制备方法 |
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 |
| DE2452805A1 (de) * | 1974-11-07 | 1976-05-20 | Basf Ag | Verfahren zur abtrennung von rueckstaenden der toluylendiisocyanatherstellung |
| DE4127514A1 (de) | 1991-08-20 | 1993-02-25 | Bayer Ag | Verfahren zur gewinnung von polyisocyanaten aus destillationsrueckstaenden der toluylendiisocyanatherstellung |
| DE4142769A1 (de) | 1991-12-23 | 1993-06-24 | Bayer Hispania Ind S A | Verfahren zur herstellung von isocyanaten und aufarbeitung des rueckstandes |
| US5962728A (en) * | 1997-10-31 | 1999-10-05 | Arco Chemical Technology, L.P. | Isocyanate residue purification |
| DE19827852A1 (de) | 1998-06-23 | 1999-12-30 | Bayer Ag | Verfahren zur Isolierung von Polymeren aus Lösungen |
| DE10260092A1 (de) | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur Reinigung von Isocyanaten |
| DE10260093A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur Abtrennung von Isocyanaten aus einem Reaktionsgemisch |
-
2008
- 2008-08-27 JP JP2010522352A patent/JP5398714B2/ja not_active Expired - Fee Related
- 2008-08-27 EP EP08803255.2A patent/EP2197836B1/de not_active Not-in-force
- 2008-08-27 CN CN2008801048496A patent/CN101790510B/zh not_active Expired - Fee Related
- 2008-08-27 WO PCT/EP2008/061188 patent/WO2009027418A1/de not_active Ceased
- 2008-08-27 KR KR1020107007079A patent/KR101578565B1/ko not_active Expired - Fee Related
- 2008-08-27 MX MX2010001396A patent/MX2010001396A/es not_active Application Discontinuation
- 2008-08-27 US US12/675,095 patent/US8273915B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR101578565B1 (ko) | 2015-12-17 |
| EP2197836B1 (de) | 2013-04-24 |
| US8273915B2 (en) | 2012-09-25 |
| CN101790510B (zh) | 2013-07-24 |
| WO2009027418A1 (de) | 2009-03-05 |
| CN101790510A (zh) | 2010-07-28 |
| US20110124908A1 (en) | 2011-05-26 |
| KR20100082831A (ko) | 2010-07-20 |
| MX2010001396A (es) | 2010-03-01 |
| JP2010536928A (ja) | 2010-12-02 |
| EP2197836A1 (de) | 2010-06-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5398714B2 (ja) | イソシアネートの製造方法 | |
| JP5599129B2 (ja) | イソシアネートの製造方法 | |
| CN106458863B (zh) | 运行气相光气化装置的方法 | |
| CN109748822B (zh) | 一种制备异氰酸酯单体的方法和系统 | |
| KR101685699B1 (ko) | 이소시아네이트의 기상 제조 방법 | |
| JP7155125B2 (ja) | イソシアネートの製造方法 | |
| CN110891932B (zh) | 在气相中制备异氰酸酯的方法 | |
| KR20160137545A (ko) | 이소시아네이트의 제조 방법 | |
| JP2016531124A (ja) | イソシアネート製造において生じる蒸留残渣から有機イソシアネートを取得する方法 | |
| KR20150114523A (ko) | 기체상에서 1차 아민의 포스겐화에 의해 제조된 이소시아네이트를 포스겐화 기체의 조생성물로부터 분리하는 방법 | |
| US9845286B2 (en) | Process for operating a gas phase phosgenation plant | |
| US10858311B2 (en) | Method for producing isocyanates | |
| JP7093183B2 (ja) | 気相中におけるジイソシアネートの製造方法 | |
| HUE024436T2 (en) | Method for preparing an isocyanate compound | |
| CN101273010A (zh) | 纯化含有异氰酸酯的残余物的方法 | |
| CN115397808A (zh) | 运行用于连续制备异氰酸酯的装置的方法 | |
| HK1124586A (en) | A process for the production of isocyanates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110826 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110826 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130417 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130521 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130819 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130924 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20131022 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |