GB818434A - The decarboxylation of aromatic hydroxy acids - Google Patents

The decarboxylation of aromatic hydroxy acids

Info

Publication number
GB818434A
GB818434A GB1305957A GB1305957A GB818434A GB 818434 A GB818434 A GB 818434A GB 1305957 A GB1305957 A GB 1305957A GB 1305957 A GB1305957 A GB 1305957A GB 818434 A GB818434 A GB 818434A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
per cent
ammonia
acid
amine
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.)
Expired
Application number
GB1305957A
Inventor
Arthur John Rostron
Arthur Marshall Spivey
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.)
Monsanto Chemicals Ltd
Original Assignee
Monsanto Chemicals 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 Monsanto Chemicals Ltd filed Critical Monsanto Chemicals Ltd
Priority to GB1305957A priority Critical patent/GB818434A/en
Publication of GB818434A publication Critical patent/GB818434A/en
Expired 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
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms

Landscapes

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

Abstract

Hydroxy aryl carboxylic acids are decarboxylated by heating in an aqueous medium in the presence of ammonia or an aliphatic amine. The preferred amines are mono- or di-methylamine or ethylamine or mono- or di-ethanolamine and the decarboxylation may be carried out by heating the mixture in a closed system at 100-300 DEG C., preferably 150-200 DEG C. The amine or ammonia may be present in an amount between 0.5 and 5 per cent, preferably about 1 per cent, of the weight of the hydroxy acid and the quantity of water may vary from 0.5 to 3 times the weight of the hydroxy acid. In the examples 4-hydroxy isophthalic acid is heated in a sealed tube for 1 1/2 hours at about 180 DEG C. with (1) 1 per cent monoethanolamine; (2) 1 per cent diethylamine; (4) 1 per cent ammonia; (3) a mixture containing 4-hydroxy isophthalic acid, p-hydroxy benzoic acid, salicylic acid and phenol is heated 6 hours at 159-62 DEG with 1 per cent monoethanolamine. Blank runs without ammonia or an amine are made in each example. The products from all the examples include phenol, p-hydroxy benzoic acid, salicylic acid and unchanged starting material. A higher yield of phenol is obtained when the mixture includes ammonia or an aliphatic amine.
GB1305957A 1957-04-24 1957-04-24 The decarboxylation of aromatic hydroxy acids Expired GB818434A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1305957A GB818434A (en) 1957-04-24 1957-04-24 The decarboxylation of aromatic hydroxy acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1305957A GB818434A (en) 1957-04-24 1957-04-24 The decarboxylation of aromatic hydroxy acids

Publications (1)

Publication Number Publication Date
GB818434A true GB818434A (en) 1959-08-19

Family

ID=10016049

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1305957A Expired GB818434A (en) 1957-04-24 1957-04-24 The decarboxylation of aromatic hydroxy acids

Country Status (1)

Country Link
GB (1) GB818434A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4594459A (en) * 1985-03-25 1986-06-10 The Dow Chemical Company Preparation of p-isopropenyl phenol and related compounds
US5329054A (en) * 1993-07-19 1994-07-12 Albemarle Corporation Decarboxylation process
EP0741122A1 (en) * 1995-05-02 1996-11-06 Hoechst Aktiengesellschaft Process for preparing aromatic compounds through decarboxylation of aromatic carboxylic acids
JP2017093371A (en) * 2015-11-26 2017-06-01 Ｍｃフードスペシャリティーズ株式会社 New smoke feeling imparting agent, and method for producing the same
CN111087309A (en) * 2019-12-19 2020-05-01 西安近代化学研究所 Method for preparing 2-methylbutylamine by one-step method
WO2020114925A1 (en) * 2018-12-07 2020-06-11 Covestro Deutschland Ag Method for producing a hydroxy compound by decarboxylation in the presence of a bronsted base
CN113227030A (en) * 2018-12-07 2021-08-06 科思创知识产权两合公司 Method for producing hydroxy compounds by decarboxylation
CN113382978A (en) * 2018-12-07 2021-09-10 科思创知识产权两合公司 Method for producing hydroxy compounds by decarboxylation in the absence of a catalyst

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4594459A (en) * 1985-03-25 1986-06-10 The Dow Chemical Company Preparation of p-isopropenyl phenol and related compounds
US5329054A (en) * 1993-07-19 1994-07-12 Albemarle Corporation Decarboxylation process
EP0635466A1 (en) * 1993-07-19 1995-01-25 Albemarle Corporation Decarboxylation process
EP0741122A1 (en) * 1995-05-02 1996-11-06 Hoechst Aktiengesellschaft Process for preparing aromatic compounds through decarboxylation of aromatic carboxylic acids
US5739388A (en) * 1995-05-02 1998-04-14 Hoechst Aktiengesellschaft Process for the preparation of aromatic compounds by decarboxylation of aromatic carboxylic acids
JP2017093371A (en) * 2015-11-26 2017-06-01 Ｍｃフードスペシャリティーズ株式会社 New smoke feeling imparting agent, and method for producing the same
CN113227029A (en) * 2018-12-07 2021-08-06 科思创知识产权两合公司 Method for producing hydroxy compounds by decarboxylation in the presence of Bronsted bases
WO2020114925A1 (en) * 2018-12-07 2020-06-11 Covestro Deutschland Ag Method for producing a hydroxy compound by decarboxylation in the presence of a bronsted base
CN113227030A (en) * 2018-12-07 2021-08-06 科思创知识产权两合公司 Method for producing hydroxy compounds by decarboxylation
CN113382978A (en) * 2018-12-07 2021-09-10 科思创知识产权两合公司 Method for producing hydroxy compounds by decarboxylation in the absence of a catalyst
JP2022513707A (en) * 2018-12-07 2022-02-09 コベストロ・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・アンド・コー・カーゲー Method for Producing Hydroxy Compound by Decarboxylation
JP2022513698A (en) * 2018-12-07 2022-02-09 コベストロ・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・アンド・コー・カーゲー A method for producing a hydroxy compound by decarboxylation in the presence of Bronsted base.
CN113227030B (en) * 2018-12-07 2023-09-12 科思创知识产权两合公司 Process for preparing hydroxy compounds by decarboxylation
CN111087309A (en) * 2019-12-19 2020-05-01 西安近代化学研究所 Method for preparing 2-methylbutylamine by one-step method
CN111087309B (en) * 2019-12-19 2023-03-21 西安近代化学研究所 Method for preparing 2-methylbutylamine by one-step method

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