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WO2004069780A1 - Procede de production d'acides adipiques comportant des chaines laterales - Google Patents

Procede de production d'acides adipiques comportant des chaines laterales Download PDF

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Publication number
WO2004069780A1
WO2004069780A1 PCT/JP2004/001403 JP2004001403W WO2004069780A1 WO 2004069780 A1 WO2004069780 A1 WO 2004069780A1 JP 2004001403 W JP2004001403 W JP 2004001403W WO 2004069780 A1 WO2004069780 A1 WO 2004069780A1
Authority
WO
WIPO (PCT)
Prior art keywords
reaction
alkyl
hydroxide
adipic acid
general formula
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/JP2004/001403
Other languages
English (en)
Japanese (ja)
Inventor
Yukihiro Isogai
Tomoyasu Ishiguro
Kenji Harada
Yoshiyasu Kubota
Masumi Iwasawa
Seiji Saitou
Ikuo Shimizu
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.)
KH Neochem Co Ltd
Original Assignee
Kyowa Hakko Chemical Co Ltd
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 Kyowa Hakko Chemical Co Ltd filed Critical Kyowa Hakko Chemical Co Ltd
Priority to JP2005504918A priority Critical patent/JPWO2004069780A1/ja
Publication of WO2004069780A1 publication Critical patent/WO2004069780A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting

Definitions

  • the present invention relates to a method for producing a branched adipic acid which is useful for applications such as a polyamide modifier, a polyester modifier, a cosmetic base, and a raw material of polyester or polyamide.
  • the method for producing 2,5-getyl adipic acid is as follows: 1,3-butadiene and sodium metal are reacted in dimethyl ether at -70 ° C, and magnesium bromide; There is known a method for producing the desired 2,5-getyl adipic acid by reacting (see US Pat. No. 3,375,272).
  • a peroxide such as ditert-butylperoxide is used as a catalyst, and propionic acid and acetylene are reacted at 120 ° C in n-nonane.
  • a method for producing the desired 2,5-dimethyladipic acid is known (see US Pat. No. 3,549,977).
  • An object of the present invention is to provide an industrially suitable method for producing a branched adipic acid.
  • the present invention provides the following (1) to (3).
  • R 7 represents formyl or hydroxymethyl, and is a single bond or a double bond.
  • a general formula (II) characterized by including a step of reacting in the presence of a hydroxide of an alkaline earth metal.
  • examples of the alkyl include linear or branched alkyl having 1 to 1 ° carbon atoms, and specific examples thereof include methyl, ethyl, propyl, isopropyl, and butyl. And isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl and the like, and among them, methyl or ethyl is preferable.
  • Compound (I) which is a raw material of the production method of the present invention, can be obtained by cyclizing an acrolein derivative by a known method (US Pat. Accordingly, the obtained dihydropyran derivative is converted to hydrogen It can be obtained by reduction.
  • hydroxides of alkaline metal or alkaline earth metals include hydroxide hydroxide, sodium hydroxide, magnesium hydroxide, calcium hydroxide, and the like. These may be used alone or in combination of two or more.
  • the amount of hydroxide of alkali metal or earth metal used is preferably 1.5 mol or more, more preferably 1.5 to 5.5 mol, per 1 mol of compound (I). It is preferably 0 mol, and more preferably 1.8 to 3.0 mol. ''
  • the reaction temperature is preferably from 200 to 320 ° C, more preferably from 200 to 250 ° C, and further preferably from 220 to 250 ° C. More preferably, the temperature is 250 ° C.
  • the reaction is carried out at normal pressure or under pressure, preferably at most 2.0 MPa, more preferably at most 1.0 MPa.
  • the reaction time is not particularly limited, but is preferably 5 hours or more, and more preferably 5 to 20 hours.
  • reaction solvent In the reaction, a reaction solvent may be used, and the reaction solvent is not particularly limited as long as it does not affect the reaction.
  • the reaction solvent include ether solvents such as dibenzyl ether, hydrocarbon solvents such as liquid paraffin, and the like, and these may be used as a mixture.
  • the amount of the reaction solvent is not particularly limited, but is preferably 50 to 200% by weight, more preferably 70 to 150% by weight, based on the compound (I). '
  • the reaction may be performed by adding a metal oxide such as zinc oxide or copper oxide as a catalyst.
  • a metal oxide such as zinc oxide or copper oxide
  • the amount of the catalyst to be used is preferably 0.1 to 5% by weight based on the compound (I). '
  • the compound (II) can be obtained in the form of a salt of an alkali metal or an alkaline earth metal.
  • the compound (II) can be obtained by adding an aqueous solution of sulfuric acid, hydrochloric acid or the like thereto.
  • the obtained compound (II) may be subjected to a purification operation such as extraction, crystallization, or distillation from the reaction solution or the like in order to improve the purity.
  • the production method of the present invention is an industrially suitable production method that is simple, inexpensive, and excellent in safety.
  • Compound (II) is useful for applications such as polyamide modifiers, polyester modifiers, cosmetic bases, and raw materials for polyesters or polyamides.
  • the reaction solution containing 2,5-getyl sodium adipic acid salt was cooled to 100 ° C or less, dissolved in 400 g of distilled water, and further precipitated by adding dropwise 420 g of 30% sulfuric acid.
  • 5-Jetyl adipine yeast was collected by filtration.
  • the obtained crude 2,5-diethyladipate was dissolved in 300 ml of methyl isobutyl ketone, washed with water, and concentrated under reduced pressure at 60 ° C to obtain 183 g of a residue containing 2,5-diethyladipate. Obtained.
  • the residue was crystallized from n-hexane to obtain 170 g (yield: 85%) of white crystals of 2,5-getyladipic acid.
  • the physical property values of the obtained 2,5-getyladipic acid are shown below.
  • the starting materials were 2,5-diethyltetrahydropyran-1-methanol 172.0 g (1. Omo 1), potassium hydroxide (manufactured by Kanto Chemical Co., Ltd.) 99.0 g (3.0 mo 1) and liquid paraffin 60
  • S manufactured by Chuo Kasei Co., Ltd.
  • S was changed to 200 g, to give 158 g (yield 79%) of white crystals of 2,5-getyladipic acid.
  • Example 3 Synthesis of 2,5-diethyladipate
  • the raw materials were 2,5-tetraethyl-1,4-dihydro-2H-pyran-1-2-carboaldehyde '168.0 g (1.0 Omo 1), hydroxide hydroxide (Kanto Chemical Co., Ltd.) 99.0 g ( 3. Omo 1) and liquid paraffin 60 S (manufactured by Chuo Kasei Co., Ltd.) were changed to 200 g, and the same operation as in Example 1 was carried out to obtain 131 g of 2,5-getylazivic acid as white crystals (yield 65 %).
  • an industrially suitable method for producing a branched adipic acid which is useful for applications such as a polyamide modifier, a polyester modifier, a cosmetic base, a polyester or a polyamide raw material, and the like.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production d'acides adipiques comportant des chaînes latérales et représentés par la formule générale (II) (dans laquelle R1, R2, R3, R4, R5 et R6 représentent chacun indépendamment hydrogène ou alkyle, à condition qu'au moins un desdits R représente alkyle). Le procédé est caractérisé en ce qu'il comporte l'étape consistant à faire réagir un composé représenté par la formule générale (I) (dans laquelle R1, R2, R3, R4, R5 et R6 sont tels que définis plus haut ; R7 représente formyle ou hydroxyméthyle ; et le symbole ????? représente une liaison simple ou double) en présence d'un hydroxyde de métal alcalin ou d'un hydroxyde de métal alcalino-terreux.
PCT/JP2004/001403 2003-02-10 2004-02-10 Procede de production d'acides adipiques comportant des chaines laterales Ceased WO2004069780A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2005504918A JPWO2004069780A1 (ja) 2003-02-10 2004-02-10 分岐アジピン酸の製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2003-032090 2003-02-10
JP2003032090 2003-02-10

Publications (1)

Publication Number Publication Date
WO2004069780A1 true WO2004069780A1 (fr) 2004-08-19

Family

ID=32844328

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2004/001403 Ceased WO2004069780A1 (fr) 2003-02-10 2004-02-10 Procede de production d'acides adipiques comportant des chaines laterales

Country Status (3)

Country Link
JP (1) JPWO2004069780A1 (fr)
TW (1) TW200418753A (fr)
WO (1) WO2004069780A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008080613A1 (fr) * 2006-12-29 2008-07-10 Abbott Laboratories Vascular Enterprises Limited Dispositifs médicaux comprenant un polyamide modifié
US8389646B2 (en) 2007-05-10 2013-03-05 Abbott Laboratories Vascular Enterprises Limited Medical devices comprising a co-polymer of a modified polyamide and a polycarbonate
US8492484B2 (en) 2007-05-10 2013-07-23 Abbott Laboratories Vascular Enterprises Limited Medical devices comprising a co-polymer of a polyamide and a polycarbonate diamine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07258148A (ja) * 1994-03-23 1995-10-09 Kuraray Co Ltd ３−メチルグルタル酸の製造方法
JPH10316610A (ja) * 1997-05-13 1998-12-02 Daicel Chem Ind Ltd エーテル類の酸化方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07258148A (ja) * 1994-03-23 1995-10-09 Kuraray Co Ltd ３−メチルグルタル酸の製造方法
JPH10316610A (ja) * 1997-05-13 1998-12-02 Daicel Chem Ind Ltd エーテル類の酸化方法

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008080613A1 (fr) * 2006-12-29 2008-07-10 Abbott Laboratories Vascular Enterprises Limited Dispositifs médicaux comprenant un polyamide modifié
US8304498B2 (en) 2006-12-29 2012-11-06 Abbott Laboratories Vascular Enterprises Limited Medical devices comprising a modified polyamide
CN101611075B (zh) * 2006-12-29 2014-06-25 雅培血管企业有限公司 包含改性聚酰胺的医用器件
US8389646B2 (en) 2007-05-10 2013-03-05 Abbott Laboratories Vascular Enterprises Limited Medical devices comprising a co-polymer of a modified polyamide and a polycarbonate
US8492484B2 (en) 2007-05-10 2013-07-23 Abbott Laboratories Vascular Enterprises Limited Medical devices comprising a co-polymer of a polyamide and a polycarbonate diamine

Also Published As

Publication number Publication date
JPWO2004069780A1 (ja) 2006-05-25
TW200418753A (en) 2004-10-01

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