JP5787908B2 - イソシアネートの生産方法 - Google Patents
イソシアネートの生産方法 Download PDFInfo
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- JP5787908B2 JP5787908B2 JP2012557489A JP2012557489A JP5787908B2 JP 5787908 B2 JP5787908 B2 JP 5787908B2 JP 2012557489 A JP2012557489 A JP 2012557489A JP 2012557489 A JP2012557489 A JP 2012557489A JP 5787908 B2 JP5787908 B2 JP 5787908B2
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- 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 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
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- 238000005406 washing Methods 0.000 description 2
- ODKSRULWLOLNJQ-UHFFFAOYSA-N 1,2-diisocyanatocyclohexane Chemical compound O=C=NC1CCCCC1N=C=O ODKSRULWLOLNJQ-UHFFFAOYSA-N 0.000 description 1
- PFUKECZPRROVOD-UHFFFAOYSA-N 1,3,5-triisocyanato-2-methylbenzene Chemical compound CC1=C(N=C=O)C=C(N=C=O)C=C1N=C=O PFUKECZPRROVOD-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 description 1
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
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- LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
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- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
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- 125000005843 halogen group Chemical group 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
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- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical class COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
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- RPDJEKMSFIRVII-UHFFFAOYSA-N oxomethylidenehydrazine Chemical compound NN=C=O RPDJEKMSFIRVII-UHFFFAOYSA-N 0.000 description 1
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Images
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
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(a)反応ゾーン中での少なくとも一種のアミンとホスゲンとの気相反応と、
(b)続く間接冷却による冷却ゾーン中での反応ガスの冷却、
ただし、少なくとも該冷却ゾーン中の最も温度が高い領域において、反応ガスの熱を吸収する冷却媒体が生成物に対して交流で流される。
「反応ゾーン」は、反応器の内部で工程(a)の反応が進行する領域を意味するものとする。化学量論的また反応速度論的に出発化合物と中間体の変換が実質的に完了している領域または点は、(空間的)反応ゾーンの末端と(反応のための)変換の終了を示す。本プロセスで製造しようとするイソシアネートまたは相当するカルバモイル塩化物の少なくとも90重量%、好ましくは少なくとも95重量%、特に少なくとも99重量%の生成が終了している時には、出発化合物の変換は実質的に完了している。
本発明によれば、次いで工程(b)で、反応ガスを冷却ゾーンで間接冷却により冷却する。その際、反応ガスの熱を吸収する冷却媒体は、少なくとも該冷却ゾーン中の最も高温の領域において生成物流に対して向流に流される。
行われる。
工程(b)と必要なら他の冷却ステージ(bb等)の後で、イソシアネートを、必要なら工程(c)における副生成物と未反応反応物の除去のための後処理にかける。この後処理には、凝縮相中の残留するホスゲンと塩化水素の気化が含まれる。
少なくとも一種のアミンとホスゲンを含む反応物流(6)が、反応器(2)中にある反応ゾーン(1)に入る。次いで、得られたガス流(生成物流(5))が、冷却装置(3)、好ましくは管束伝熱装置(管束熱交換器)内にある冷却ゾーン(12)に入る。
2 反応器
3 冷却装置
4 冷却流体流
5 生成物流
6 反応物流
7 混合装置
8 アミン流
9 加熱装置
10 ホスゲン流
11 冷却流
12 冷却ゾーン
13 任意の補助熱源
Claims (16)
- (a)反応ゾーン中での少なくとも一種のアミンとホスゲンとの気相反応と
(b)続く冷却ゾーンでの間接冷却による反応ガスの冷却とを含む
イソシアネートの生産方法であって、
該冷却ゾーン中の少なくとも最も高温の領域において、反応ガスの熱を吸収する冷却媒体を、生成物流に対して向流に流すことを特徴とする方法。 - 工程(b)の冷却が、比伝熱面積が反応ガス1m3に対して少なくとも300m2/m3である熱交換器中で行われる請求項1に記載の方法。
- 上記熱交換器が管束熱交換器である請求項2に記載の方法。
- 工程(b)での冷却時間が0.01〜10秒間である請求項1〜3のいずれか一項に記載の方法。
- 上記イソシアネートが、工程(b)の間、凝縮状態で存在しない請求項1〜4のいずれか一項に記載の方法。
- 工程(a)の反応ゾーンと工程(b)の冷却ゾーンが、管形である同一装置内にある請求項1〜5のいずれか一項に記載の方法。
- 工程(b)での冷却の後に、工程(bb)として反応ガスのさらなる冷却が続く請求項1〜6のいずれか一項に記載の方法。
- 工程(b)と(bb)での冷却がいずれの場合も間接的に行われ、工程(b)と(bb)での冷媒が異なる回路を流れる請求項7に記載の方法。
- 上記反応ガスが工程(bb)で直接冷却される請求項7に記載の方法。
- 冷却が、工程(bb)での急冷により行われる請求項9に記載の方法。
- 工程(b)で冷却媒体により吸収された熱が、少なくとも部分的に、工程(a)の反応における少なくとも一つの反応物流への間接的熱移動に使用される請求項1〜10のいずれか一項に記載の方法。
- 反応ガスの熱を吸収する冷却媒体が溶融塩である請求項1〜11のいずれか一項に記載の方法。
- 用いるアミンが、6〜18個の炭素原子を有する少なくとも一種の芳香族ジアミンであるか、2〜18個の炭素原子を有する少なくとも一種の(環式)脂肪族ジアミンである請求項1〜12のいずれか一項に記載の方法。
- 用いるアミンが、トルエンジアミンから選ばれる少なくとも一種である請求項1〜13のいずれか一項に記載の方法。
- 用いるアミンが、ジアミノジフェニルメタンから選ばれる少なくとも一種である請求項1〜13のいずれか一項に記載の方法。
- 用いるアミンが、2〜18個の炭素原子を有する少なくとも一種の脂肪族ジアミンである請求項1〜13のいずれか一項に記載の方法。
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EP10156944 | 2010-03-18 | ||
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PCT/EP2011/053583 WO2011113737A1 (de) | 2010-03-18 | 2011-03-10 | Verfahren zur herstellung von isocyanaten |
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JP (1) | JP5787908B2 (ja) |
KR (1) | KR20130029064A (ja) |
CN (1) | CN102803206B (ja) |
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US9321720B2 (en) | 2010-10-14 | 2016-04-26 | Basf Se | Process for preparing isocyanates |
US8969615B2 (en) | 2011-03-31 | 2015-03-03 | Basf Se | Process for preparing isocyanates |
US8816126B2 (en) | 2011-09-02 | 2014-08-26 | Basf Se | Process for preparing isocyanates |
US8791291B2 (en) | 2011-11-29 | 2014-07-29 | Basf Se | Process for preparing isocyanates by phosgenation of the corresponding amines in the gas phase |
EP2829533A1 (de) | 2013-07-26 | 2015-01-28 | Bayer MaterialScience AG | Verfahren zur herstellung von isocyanaten |
WO2016198404A1 (de) * | 2015-06-12 | 2016-12-15 | Covestro Deutschland Ag | Verfahren zur herstellung von diisocyanaten in der gasphase |
US10618871B2 (en) * | 2016-08-17 | 2020-04-14 | Covestro Deutschland Ag | Process for producing isocyanate and at least one further chemical product in an integrated production |
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FR2723585B1 (fr) | 1994-08-12 | 1996-09-27 | Rhone Poulenc Chimie | Procede de preparation de composes du type polyisocyanates aromatiques en phase gazeuse. |
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DE19654515C1 (de) * | 1996-12-27 | 1998-10-01 | Degussa | Verfahren zur kontinuierlichen Herstellung von Methylmercaptan |
DE10133729A1 (de) | 2001-07-11 | 2003-01-23 | Bayer Ag | Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten |
DE10133728A1 (de) | 2001-07-11 | 2003-01-23 | Bayer Ag | Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten |
DE10158160A1 (de) * | 2001-11-28 | 2003-06-12 | Basf Ag | Herstellung von Isocyanaten in der Gasphase |
DE10161384A1 (de) | 2001-12-14 | 2003-06-18 | Bayer Ag | Verbessertes Verfahren für die Herstellung von (/Poly)-isocyanaten in der Gasphase |
DE10222023A1 (de) | 2002-05-17 | 2003-11-27 | Bayer Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
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DE102006058634A1 (de) * | 2006-12-13 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
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CN101801920B (zh) | 2007-09-19 | 2013-07-10 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
EP2060560B1 (en) * | 2007-11-14 | 2016-04-13 | Covestro Deutschland AG | Preparation of light-colored isocyanates |
DE102007056511A1 (de) | 2007-11-22 | 2009-05-28 | Bayer Materialscience Ag | Verfahren zur Herstellung aromatischer Diisocyanate in der Gasphase |
CN102317254B (zh) | 2008-07-23 | 2014-11-19 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
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JP2013522261A (ja) | 2013-06-13 |
WO2011113737A1 (de) | 2011-09-22 |
PL2547652T3 (pl) | 2015-03-31 |
KR20130029064A (ko) | 2013-03-21 |
EP2547652B1 (de) | 2014-09-03 |
EP2547652A1 (de) | 2013-01-23 |
CN102803206B (zh) | 2015-01-07 |
ES2522840T3 (es) | 2014-11-18 |
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