WO2004106314A1 - Procede de fabrication d'un compose biphenyle contenant un noyau d'oxetane - Google Patents

Procede de fabrication d'un compose biphenyle contenant un noyau d'oxetane Download PDF

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Publication number
WO2004106314A1
WO2004106314A1 PCT/JP2004/007328 JP2004007328W WO2004106314A1 WO 2004106314 A1 WO2004106314 A1 WO 2004106314A1 JP 2004007328 W JP2004007328 W JP 2004007328W WO 2004106314 A1 WO2004106314 A1 WO 2004106314A1
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WO
WIPO (PCT)
Prior art keywords
reaction
reaction solvent
water
compound
biphenyl
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/JP2004/007328
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English (en)
Japanese (ja)
Inventor
Osamu Fujimura
Tetsuro Tsuji
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.)
Ube Corp
Original Assignee
Ube Industries 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 Ube Industries Ltd filed Critical Ube Industries Ltd
Priority to JP2005506497A priority Critical patent/JPWO2004106314A1/ja
Publication of WO2004106314A1 publication Critical patent/WO2004106314A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms

Definitions

  • the above method (1) includes the above two steps, and when this method is carried out on an industrial scale, there is a problem that the process operation is complicated, and (2) 4, 4, 1, bis (c) (Rhomethyl) Biphenyl and the aromatic hydrocarbon for the reaction solvent cause a Freetel-Crafts reaction. There is a problem that by-products are generated.
  • J. Macromolecule ar Chem., Pure Appl. Nem., A30, 189 describes a 3-hydroxymethyloxetane compound, a trimethylolalkane compound and dimethyl carbonate.
  • a method for producing as a starting material is disclosed. Disclosure of the invention
  • R in the formula (1) represents a hydrogen atom or an alkyl group
  • 4,4,1-bis (chloromethyl) biphenyl and a base are reacted in a reaction solvent to obtain the following formula ( 2)
  • the non-aromatic hydrocarbon for a reaction solvent is preferably selected from aliphatic saturated hydrocarbons.
  • the reaction further includes removing water produced as a reaction by-product by azeotropic distillation with the reaction solvent.
  • 4,4,1-bis (chloromethyl) biphenyl can be produced by a known method, for example, a method described in JP-A-10-139699, or a commercially available product can be used. May be used.
  • the concentration of the raw materials in the reaction system may be excessively low, and the production efficiency may be insufficient. If it exceeds 75% by mass, the viscosity of the reaction system becomes excessively high, and the stirring efficiency may become insufficient.
  • phase transfer catalyst for example, a phase transfer catalyst, 4, 4 '- relative to bis (black Romechi Le) molar amount of biphenyl, 10 moles 0 It may be used in a ratio of not more than / o, and a preferable use ratio is 5 mol% or less.
  • the method of the present invention is further described by the following examples.
  • the quantitative analysis of the products of the following examples was performed using high performance liquid chromatography (HPLC) under the following conditions.
  • the resulting mixture was heated under a nitrogen stream at a hot water bath temperature of 110 ° C., and heated to reflux for 3 hours while removing water by azeotropic reaction to carry out a reaction.
  • the amount of water removed by azeotropic distillation during this reaction reached 1.9 ml.
  • the cooled reaction mixture was cooled to 40 ° C, and 2.5 ml of ethanol was added thereto, followed by total reflux for 1 hour. Thereafter, 40 ml of cyclohexane was added to the reaction mixture, and the mixture was stirred for 30 minutes.
  • the obtained reaction mixture was subjected to filtration to remove insoluble white solids, and the obtained filtrate was washed twice with 40 ml of water.
  • the reaction mixture after washing with water is heated to remove cyclohexane by evaporation, and the target compound: 4,4'-bis (1'-ethyl-1,3-oxetanylmethoxy) 19.5 g of methylbiphenyl is collected as a yellow oil. (Yield 88%).
  • the purity of the collected product was 90.4% in terms of area percentage by HPLC analysis.
  • the method of the present invention solves the problems of the known production methods, that is, suppresses the formation of by-products, and is a single-step, simple operation, and efficiently, the desired biphenyl compound having an oxetane ring. Can be manufactured.
  • the method of the present invention by using a reaction solvent that azeotropes with water and using an alkali metal hydroxide as the base, the generation of by-products is suppressed, and the water generated as by-products is suppressed. Is efficiently removed by azeotropic distillation with the reaction solvent can do. Since the target substance can be efficiently purified and collected from the reaction mixture produced by the single-step reaction of the method of the present invention, the method of the present invention has high industrial utility.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé pour produire en un seul stade, efficacement et facilement, un composé biphényle contenant un noyau d'oxétane représenté par la formule générale (2). Le procédé consiste à faire réagir un composé de 3-hydroxyméthyloxane représenté par la formule générale (1) avec 4,4'-bis(chlorométhyl)biphényl dans un solvant de réaction en présence d'une base, le solvant de réaction étant un hydrocarbure non aromatique (p.ex., aliphatique), et la base étant un hydroxyde de métal alcalin. De préférence, la réaction est effectuée pendant l'évacuation de l'eau de sous-produit en tant que mélange azéotropique avec le solvant de réaction.
PCT/JP2004/007328 2003-05-28 2004-05-21 Procede de fabrication d'un compose biphenyle contenant un noyau d'oxetane Ceased WO2004106314A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2005506497A JPWO2004106314A1 (ja) 2003-05-28 2004-05-21 オキセタン環含有ビフェニル化合物の製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2003150302 2003-05-28
JP2003-150302 2003-05-28

Publications (1)

Publication Number Publication Date
WO2004106314A1 true WO2004106314A1 (fr) 2004-12-09

Family

ID=33487173

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2004/007328 Ceased WO2004106314A1 (fr) 2003-05-28 2004-05-21 Procede de fabrication d'un compose biphenyle contenant un noyau d'oxetane

Country Status (2)

Country Link
JP (1) JPWO2004106314A1 (fr)
WO (1) WO2004106314A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006206464A (ja) * 2005-01-26 2006-08-10 Ube Ind Ltd ビフェニル誘導体の製法
US20100243304A1 (en) * 2007-03-05 2010-09-30 Nobuaki Otsuki Solder resist, dry film thereof, cured product, and printed wiring board
WO2021197057A1 (fr) * 2020-04-03 2021-10-07 常州强力先端电子材料有限公司 Procédé de synthèse pour synthétiser un dérivé d'oxétane par microréacteur
CN113493427A (zh) * 2020-04-03 2021-10-12 常州强力先端电子材料有限公司 通过微反应器合成氧杂环丁烷衍生物的合成方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11106380A (ja) * 1997-09-30 1999-04-20 Ube Ind Ltd オキセタン環を有するビフェニル誘導体
JP2001163882A (ja) * 1999-09-28 2001-06-19 Ube Ind Ltd オキセタン環を有するシアヌル酸誘導体

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11106380A (ja) * 1997-09-30 1999-04-20 Ube Ind Ltd オキセタン環を有するビフェニル誘導体
JP2001163882A (ja) * 1999-09-28 2001-06-19 Ube Ind Ltd オキセタン環を有するシアヌル酸誘導体

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MORRISON R.T. ET AL.: "Morrison boyd yuki kagaku (chu)", TOKYO KAGAKU DOJIN, 1994, pages 720 - 721, XP002983049 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006206464A (ja) * 2005-01-26 2006-08-10 Ube Ind Ltd ビフェニル誘導体の製法
US20100243304A1 (en) * 2007-03-05 2010-09-30 Nobuaki Otsuki Solder resist, dry film thereof, cured product, and printed wiring board
US8722816B2 (en) * 2007-03-05 2014-05-13 Nippon Shokubai Co., Ltd. Solder resist, dry film thereof, cured product, and printed wiring board
WO2021197057A1 (fr) * 2020-04-03 2021-10-07 常州强力先端电子材料有限公司 Procédé de synthèse pour synthétiser un dérivé d'oxétane par microréacteur
CN113493427A (zh) * 2020-04-03 2021-10-12 常州强力先端电子材料有限公司 通过微反应器合成氧杂环丁烷衍生物的合成方法
KR20220161446A (ko) * 2020-04-03 2022-12-06 창저우 트론리 어드벤스드 일렉트로닉 머티어리얼스 컴퍼니, 리미티드 마이크로 반응기를 통해 옥세탄 유도체를 합성하는 합성 방법
JP2023520477A (ja) * 2020-04-03 2023-05-17 常州強力先端電子材料有限公司 オキセタン誘導体をマイクロ反応器により合成する合成方法
CN113493427B (zh) * 2020-04-03 2024-11-15 常州强力先端电子材料有限公司 通过微反应器合成氧杂环丁烷衍生物的合成方法
JP7599505B2 (ja) 2020-04-03 2024-12-13 常州強力先端電子材料有限公司 オキセタン誘導体をマイクロ反応器により合成する合成方法
KR102755419B1 (ko) 2020-04-03 2025-01-21 창저우 트론리 어드벤스드 일렉트로닉 머티어리얼스 컴퍼니, 리미티드 마이크로 반응기를 통해 옥세탄 유도체를 합성하는 합성 방법
US12583830B2 (en) 2020-04-03 2026-03-24 Changzhou Tronly Advanced Electronic Materials Co., Ltd. Synthesis method for synthesizing oxetane derivative by microreactor

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