WO2009057466A1 - ジトリメチロールプロパンの製造方法 - Google Patents

ジトリメチロールプロパンの製造方法 Download PDF

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Publication number
WO2009057466A1
WO2009057466A1 PCT/JP2008/068863 JP2008068863W WO2009057466A1 WO 2009057466 A1 WO2009057466 A1 WO 2009057466A1 JP 2008068863 W JP2008068863 W JP 2008068863W WO 2009057466 A1 WO2009057466 A1 WO 2009057466A1
Authority
WO
WIPO (PCT)
Prior art keywords
ditrimethylolpropane
propenal
formaldehyde
ethyl
tmp
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.)
Ceased
Application number
PCT/JP2008/068863
Other languages
English (en)
French (fr)
Inventor
Masafumi Watanabe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Gas Chemical Co Inc
Original Assignee
Mitsubishi Gas Chemical Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsubishi Gas Chemical Co Inc filed Critical Mitsubishi Gas Chemical Co Inc
Priority to EP08844216.5A priority Critical patent/EP2204356B1/en
Priority to US12/739,019 priority patent/US8492596B2/en
Priority to CN2008801109377A priority patent/CN101821222B/zh
Priority to JP2009539010A priority patent/JP5434595B2/ja
Publication of WO2009057466A1 publication Critical patent/WO2009057466A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/13—Saturated ethers containing hydroxy or O-metal groups
    • C07C43/132—Saturated ethers containing hydroxy or O-metal groups both carbon chains being substituted by hydroxy or O-metal groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

　塩基触媒の存在下、ノルマルブチルアルデヒドとホルムアルデヒドを反応させてトリメチロールプロパンと共にジトリメチロールプロパンを製造する方法であって、（Ｉ）塩基触媒（１）の存在下、ノルマルブチルアルデヒドとホルムアルデヒド(１)を反応させて、トリメチロールプロパン、ジトリメチロールプロパンおよび２－エチル－２－プロペナールを含有する反応混合液を得る工程、（II)  得られた反応混合液を蒸留して２－エチル－２－プロペナールを回収する工程および（III)２－エチル－２－プロペナールを回収した後の蒸留残留液に、回収された２－エチル－２－プロペナールおよびホルムアルデヒド（２）、または更に塩基触媒（２）を添加し、ジトリメチロールプロパンの生成反応を進行させる工程を有し、工程Iおよび工程IIでのホルムアルデヒド及び塩基触媒を特定の供給量とすることにより、ジトリメチロールプロパンを効率良く製造する方法を提供する。本発明によれば、ｄｉ－ＴＭＰ収率が著しく上昇し、また、目的とするｄｉ－ＴＭＰの生成量に対して、ｂｉｓ－ＴＭＰの副生量を大幅に削減できるので、ｄｉ－ＴＭＰを効率良く、工業的に有利に製造できる。
PCT/JP2008/068863 2007-10-30 2008-10-17 ジトリメチロールプロパンの製造方法 Ceased WO2009057466A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP08844216.5A EP2204356B1 (en) 2007-10-30 2008-10-17 Process for production of ditrimethylolpropane
US12/739,019 US8492596B2 (en) 2007-10-30 2008-10-17 Process for production of ditrimethylolpropane
CN2008801109377A CN101821222B (zh) 2007-10-30 2008-10-17 双三羟甲基丙烷的制备方法
JP2009539010A JP5434595B2 (ja) 2007-10-30 2008-10-17 ジトリメチロールプロパンの製造方法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2007-281509 2007-10-30
JP2007281509 2007-10-30
JP2007-323792 2007-12-14
JP2007323792 2007-12-14

Publications (1)

Publication Number Publication Date
WO2009057466A1 true WO2009057466A1 (ja) 2009-05-07

Family

ID=40590858

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/068863 Ceased WO2009057466A1 (ja) 2007-10-30 2008-10-17 ジトリメチロールプロパンの製造方法

Country Status (7)

Country Link
US (1) US8492596B2 (ja)
EP (1) EP2204356B1 (ja)
JP (1) JP5434595B2 (ja)
KR (1) KR101564119B1 (ja)
CN (1) CN101821222B (ja)
TW (1) TWI422567B (ja)
WO (1) WO2009057466A1 (ja)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009143867A (ja) * 2007-12-14 2009-07-02 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造方法
JP2009143866A (ja) * 2007-12-14 2009-07-02 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造方法
WO2012033055A1 (ja) 2010-09-07 2012-03-15 三菱瓦斯化学株式会社 ジトリメチロールプロパンの製造方法
WO2013005636A1 (ja) 2011-07-01 2013-01-10 三菱瓦斯化学株式会社 ジトリメチロールプロパンの製造方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011118953B4 (de) 2011-11-19 2014-06-05 Oxea Gmbh Destillatives Verfahren zur Gewinnung von Di-Trimethylolpropan

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3097245A (en) 1959-01-13 1963-07-09 Trojan Powder Co Process for the preparation of trimethylolalkane
JPS49133311A (ja) 1972-11-23 1974-12-21
JPS5711934A (en) * 1980-06-26 1982-01-21 Koei Chem Co Ltd Production of ditrimethylolalkane or dipentaerythritol in high ratio as by-product
JPS57139028A (en) 1981-02-19 1982-08-27 Koei Chem Co Ltd Method for producing dipentaerythritol or ditrimethylol-alkane in high ratio as by-product
JPS57142929A (en) 1981-02-27 1982-09-03 Koei Chem Co Ltd Forming method of dipentaerythritol or ditrimethylolalkane as by-product at given ratio
JPH06501470A (ja) 1990-09-24 1994-02-17 ペルストルプ　アーベー ジトリメチロールプロパンの製造方法
JPH08157401A (ja) 1994-12-07 1996-06-18 Koei Chem Co Ltd トリメチロールプロパン及びジトリメチロールプロパンの製造方法
JPH09268150A (ja) 1996-04-03 1997-10-14 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造方法
JP2002047231A (ja) 2000-08-03 2002-02-12 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造法
JP2003267904A (ja) * 2002-03-14 2003-09-25 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造方法
JP2005023067A (ja) 2003-06-13 2005-01-27 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19715746A1 (de) * 1997-04-16 1998-10-22 Bayer Ag Herstellung von aromatischen Aminen mittels neuer Hydrierkatalysatoren
JP4003018B2 (ja) * 1997-08-07 2007-11-07 三菱瓦斯化学株式会社 多価アルコールの製造法
US6080896A (en) * 1997-08-07 2000-06-27 Mitsubishi Gas Chemical Company, Inc. Process for producing polyhydric alcohol
JP4730611B2 (ja) 2006-06-27 2011-07-20 横河電機株式会社 遅延時間測定方法及びこれを用いた遅延時間測定装置
CN100400489C (zh) * 2006-08-24 2008-07-09 王强 双三羟甲基丙烷和三羟甲基丙烷甲缩醛生产工艺
JP2009107964A (ja) * 2007-10-30 2009-05-21 Mitsubishi Gas Chem Co Inc ２−エチル−２−プロペナールの製造方法

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3097245A (en) 1959-01-13 1963-07-09 Trojan Powder Co Process for the preparation of trimethylolalkane
JPS49133311A (ja) 1972-11-23 1974-12-21
JPS5711934A (en) * 1980-06-26 1982-01-21 Koei Chem Co Ltd Production of ditrimethylolalkane or dipentaerythritol in high ratio as by-product
JPS57139028A (en) 1981-02-19 1982-08-27 Koei Chem Co Ltd Method for producing dipentaerythritol or ditrimethylol-alkane in high ratio as by-product
JPS57142929A (en) 1981-02-27 1982-09-03 Koei Chem Co Ltd Forming method of dipentaerythritol or ditrimethylolalkane as by-product at given ratio
JPH06501470A (ja) 1990-09-24 1994-02-17 ペルストルプ　アーベー ジトリメチロールプロパンの製造方法
JPH08157401A (ja) 1994-12-07 1996-06-18 Koei Chem Co Ltd トリメチロールプロパン及びジトリメチロールプロパンの製造方法
JPH09268150A (ja) 1996-04-03 1997-10-14 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造方法
JP2002047231A (ja) 2000-08-03 2002-02-12 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造法
JP2003267904A (ja) * 2002-03-14 2003-09-25 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造方法
JP2005023067A (ja) 2003-06-13 2005-01-27 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP2204356A4 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009143867A (ja) * 2007-12-14 2009-07-02 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造方法
JP2009143866A (ja) * 2007-12-14 2009-07-02 Mitsubishi Gas Chem Co Inc ジトリメチロールプロパンの製造方法
WO2012033055A1 (ja) 2010-09-07 2012-03-15 三菱瓦斯化学株式会社 ジトリメチロールプロパンの製造方法
US9169184B2 (en) 2010-09-07 2015-10-27 Mitsubishi Gas Chemical Company, Inc. Method for producing ditrimethylolpropane
WO2013005636A1 (ja) 2011-07-01 2013-01-10 三菱瓦斯化学株式会社 ジトリメチロールプロパンの製造方法
JPWO2013005636A1 (ja) * 2011-07-01 2015-02-23 三菱瓦斯化学株式会社 ジトリメチロールプロパンの製造方法
US8981161B2 (en) 2011-07-01 2015-03-17 Mitsubishi Gas Chemical Company, Inc. Process for production of ditrimethylolpropane

Also Published As

Publication number Publication date
US20100240931A1 (en) 2010-09-23
EP2204356A1 (en) 2010-07-07
KR101564119B1 (ko) 2015-10-28
EP2204356A4 (en) 2012-06-27
KR20100074163A (ko) 2010-07-01
CN101821222B (zh) 2013-08-21
EP2204356B1 (en) 2015-12-09
CN101821222A (zh) 2010-09-01
JPWO2009057466A1 (ja) 2011-03-10
US8492596B2 (en) 2013-07-23
TW200930695A (en) 2009-07-16
TWI422567B (zh) 2014-01-11
JP5434595B2 (ja) 2014-03-05

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