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WO1992009555A1 - Procede de preparation de carbonates de phenyle - Google Patents

Procede de preparation de carbonates de phenyle Download PDF

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Publication number
WO1992009555A1
WO1992009555A1 PCT/US1990/006860 US9006860W WO9209555A1 WO 1992009555 A1 WO1992009555 A1 WO 1992009555A1 US 9006860 W US9006860 W US 9006860W WO 9209555 A1 WO9209555 A1 WO 9209555A1
Authority
WO
WIPO (PCT)
Prior art keywords
phenyl
acetic anhydride
acetate
carbonate
methyl acetate
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/US1990/006860
Other languages
English (en)
Inventor
Hendrik E. Tuinstra
Cynthia L. Rand
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.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
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 Dow Chemical Co filed Critical Dow Chemical Co
Priority to EP19910900661 priority Critical patent/EP0558474A4/en
Priority to JP91500881A priority patent/JPH05507060A/ja
Priority to PCT/US1990/006860 priority patent/WO1992009555A1/fr
Publication of WO1992009555A1 publication Critical patent/WO1992009555A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates

Definitions

  • the present invention relates to a process for the preparation of phenyl carbonates. More particularly, the present invention allows for the preparation of phenyl carbonates utilizing as reactants a phenol; acetic anhydride; carbon monoxide; and oxygen.
  • step B reacting dimethyl carbonate with at least a portion of the phenyl acetate from step A to produce a phenyl carbonate and methyl acetate and separating the methyl acetate;
  • step D employing the acetic anhydride as at least a portion of the acetic anhydride reactant of step A.
  • reaction of phenols with acetic anhydride to form a phenyl acetate and acetic acid, step A of the present invention is a well known acetylation reaction, Suitable process conditions are disclosed, for example, in U.S. Patent 4,374,263.
  • phenol is included hydroxy benzene and C ⁇ _ ⁇ _ j alkyl or halo substituted phenols, however, the preferred reactant is hydroxybenzene.
  • the reaction of a phenol and acetic anhydride may be depicted by the following illustration. 0 0 0
  • Ar represents a arvl group or alkyl or halo substituted aryl group, particularly phenyl.
  • the reaction is conducted at moderate temperatures from 25°C to 180°C, more preferably 75°C to 150°C.
  • the products are easily separated by fractional distillation or other suitable technique. While numerous catalysts are known for the esterification process, preferred catalysts are acids, especially heterogeneous macroporous ion exchange resins in the acid form.
  • the dimethyl carbonate reactant for step B may be prepared by the reaction between methanol, carbon monoxide and oxygen, according to any suitable procedure. Suitable are those processes disclosed in U.S. Patents 3,846,468, 3,980,690, 4,452,690, 4,533,504, and 4,360,477.
  • the reaction is generally expedited by the use of a catalyst, particularly a copper or cobalt complex and the use of elevated temperatures and pressures.
  • Preferred catalysts are cuprous chloride complexed with an organic base such as pyridine, dipyridyl, imidazole, alkyl or aryl phosphines, etc.
  • Preferred temperatures are from 20 to 75°C, more preferably 25 to 50°C.
  • Preferred pressures of 0 2 and CO are from atmospheric to 20 atmospheres pressure. Reaction of dimethyl carbonate and a phenyl acetate to give the desired phenyl carbonate and by ⁇ product alkyl acetate is a known chemical transformation. This step of the process may be illustrated schematically by the following diagram.
  • this reaction has been previously disclosed, for example, in U.S. Patent 4,182,726, and U.S. Patent 4,533,504.
  • this reaction is conducted in 0 the presence of a catalyst, particularly a Lewis acid, such as AlCl , or stannate or titanate catalysts.
  • Temperatures of the reaction are from 100°C to 350°C,._ _ preferably from 150°C to 300°C.
  • Pressures are generally from atmospheric to 25 atmospheres, more preferably 5 to 5 10 atmospheres.
  • the phenyl carbonate product is a highly desired article of commerce for conversion into polycarbonate resins. Processes for such conversion are 0 also well known having been disclosed in U.S. Patents
  • the synthesized product may be a mixture of both the mono- and ditransesterified products, that is both the diphenyl carbonate and phenyl methyl carbonate products 5 are formed.
  • the phenyl carbonate product and methyl acetate are readily separated by use of standard distillation techniques and the by-product, methyl acetate, is recycled by means of a reaction with carbon monoxide to produce acetic anhydride that is used in step A.
  • Suitable processes for such reaction between methyl acetate and carbon monoxide are known and previously disclosed in the art, for example, in U.S. Patents 4,374,070, 4,559,183, and 4,046,807 and in S. W.
  • a preferred process utilizes a noble metal catalyst and temperatures from 50°C to 250°C, preferably 100°C to 200°C, and pressures from atmospheric to 500 atmospheres, preferably 10 to 250 atmospheres.
  • the present process scheme allows for the overall conversion of a phenol to the corresponding phenyl carbonate utilizing as reactants acetic anhydride, carbon monoxide and oxygen.
  • the recycle of methyl acetate intermediate allows for great economy and simplicity in the resulting process compared to the generation of a ketene intermediate.
  • the present process utilizes much lower reaction temperatures and results in greatly improved efficiency of operation.
  • intermediate by ⁇ product acetic acid may also be recycled if desired by reaction with additional methanol to form methyl acetate and then carbonylated as above explained to form acetic anhydride.
  • the acetic acid which represents a significant increase in value over the starting material, methanol, may be sold.

Landscapes

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

Abstract

Procédé permettant de préparer un carbonate aromatique à partir d'un phénol, d'anhydride acétique, de monoxyde de carbone et d'oxygène. Ce procédé comprend les étapes suivantes: A) on fait réagir de l'anhydride acétique avec du phénol pour obtenir de l'acétate de phényle; B) on fait réagir l'acétate de phényle avec du carbonate de diméthyle pour produire un carbonate de phényle et de l'acétate de méthyle; et C) on fait réagir l'acétate de méthyle avec du monoxyde de carbone pour produire de l'anhydride acétique destiné à être utilisé dans l'étape A.
PCT/US1990/006860 1990-11-21 1990-11-21 Procede de preparation de carbonates de phenyle Ceased WO1992009555A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP19910900661 EP0558474A4 (en) 1990-11-21 1990-11-21 Process for the preparation of phenyl carbonates
JP91500881A JPH05507060A (ja) 1990-11-21 1990-11-21 フェニルカーボネート類の製造方法
PCT/US1990/006860 WO1992009555A1 (fr) 1990-11-21 1990-11-21 Procede de preparation de carbonates de phenyle

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1990/006860 WO1992009555A1 (fr) 1990-11-21 1990-11-21 Procede de preparation de carbonates de phenyle

Publications (1)

Publication Number Publication Date
WO1992009555A1 true WO1992009555A1 (fr) 1992-06-11

Family

ID=22221177

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/006860 Ceased WO1992009555A1 (fr) 1990-11-21 1990-11-21 Procede de preparation de carbonates de phenyle

Country Status (3)

Country Link
EP (1) EP0558474A4 (fr)
JP (1) JPH05507060A (fr)
WO (1) WO1992009555A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0684221A1 (fr) * 1994-05-25 1995-11-29 Nippon Shokubai Co., Ltd. Procédé de préparation d'esters de l'acide carbonique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5714627A (en) * 1995-08-28 1998-02-03 Mitsubishi Gas Chemical Company, Inc. Method for preparing aromatic carbonate

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4333885A (en) * 1981-04-02 1982-06-08 Air Products And Chemicals, Inc. Method for producing carboxylic acid anhydride
US4533504A (en) * 1982-01-08 1985-08-06 General Electric Company Process for the preparation of diaryl carbonates

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4182726A (en) * 1974-06-25 1980-01-08 Snamprogetti, S.P.A. Process for the preparation of aromatic carbonates
DE2450965C2 (de) * 1974-10-26 1983-06-09 Hoechst Ag, 6230 Frankfurt Verfahren zur Herstellung von Essigsäureanhydrid
US4191996A (en) * 1977-07-22 1980-03-04 Chesley Gilman D Self-configurable computer and memory system
JPS5524452A (en) * 1978-08-08 1980-02-21 Nec Corp Integrated circuit
NZ195265A (en) * 1979-10-27 1983-05-10 British Petroleum Co Catalytic esterification of carboxylic acids or anhydrides thereof
US4452968A (en) * 1981-11-30 1984-06-05 General Electric Company Synthesis of polycarbonate from dialkyl carbonate and bisphenol diester
US4498134A (en) * 1982-01-26 1985-02-05 Hughes Aircraft Company Segregator functional plane for use in a modular array processor
JPS5968965A (ja) * 1982-10-13 1984-04-19 Mitsubishi Electric Corp 半導体メモリ
JPS5987852A (ja) * 1982-11-10 1984-05-21 Toshiba Corp 半導体記憶装置

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4333885A (en) * 1981-04-02 1982-06-08 Air Products And Chemicals, Inc. Method for producing carboxylic acid anhydride
US4533504A (en) * 1982-01-08 1985-08-06 General Electric Company Process for the preparation of diaryl carbonates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0558474A4 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0684221A1 (fr) * 1994-05-25 1995-11-29 Nippon Shokubai Co., Ltd. Procédé de préparation d'esters de l'acide carbonique
US5543546A (en) * 1994-05-25 1996-08-06 Nippon Shokubai Co., Ltd. Process for preparing carbonate esters
CN1065234C (zh) * 1994-05-25 2001-05-02 株式会社日本触媒 碳酸酯的制备方法

Also Published As

Publication number Publication date
JPH05507060A (ja) 1993-10-14
EP0558474A1 (fr) 1993-09-08
EP0558474A4 (en) 1993-09-29

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