GB743933A - Improvements in or relating to synthesis of carboxylic acids - Google Patents

Improvements in or relating to synthesis of carboxylic acids

Info

Publication number
GB743933A
GB743933A GB1742453A GB1742453A GB743933A GB 743933 A GB743933 A GB 743933A GB 1742453 A GB1742453 A GB 1742453A GB 1742453 A GB1742453 A GB 1742453A GB 743933 A GB743933 A GB 743933A
Authority
GB
United Kingdom
Prior art keywords
nickel
iodide
acid
acetate
catalyst
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
GB1742453A
Inventor
Arthur Lawrence Glasebrook
John Chaplin Snyder
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.)
Hercules Powder Co
Original Assignee
Hercules Powder 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 Hercules Powder Co filed Critical Hercules Powder Co
Priority to GB1742453A priority Critical patent/GB743933A/en
Publication of GB743933A publication Critical patent/GB743933A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/10Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
    • C07C51/12Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/10Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
    • C07C51/14Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds

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

Carboxylic acids are synthesized by the catalytic addition of carbon monoxide to an alcohol, or of carbon monoxide and water to an olefin, ether or carboxylic acid ester in the presence of a catalyst containing an element of the iron sub-group and chlorine, bromine or iodine, at a temperature of from 200 DEG to 350 DEG C. and a pressure of 2000 to 15,000 p.s.i., in which the reaction is conducted in a reactor, the inner surfaces of which consist of, or which is lined with, a metal containing at least 90 per cent titanium or zirconium. Alcohols specified are methanol, ethanol, propanol, isopropanol, butanol, amyl alcohol, cyclohexanol, terpinol, fenchyl alcohol and benzyl alcohol. An acrylic or alicyclic olefine, or an aromatic hydrocarbon with an olefinic side chain may be used, e.g. ethylene, propylene, isobutylene, pentenes, hexenes, cyclohexene, menthene, camphene or styrene. The reaction is applicable to any alkyl, cycloalkyl, aralkyl or aryl ether, either simple or mixed. Thus acetic acid is obtained from dimethyl ether and propionic acid from diethyl ether. Dicarboxylic acids are obtained from cyclic ethers, e.g. adipic acid from tetrahydrofuran. The ester used may be any alkyl, cycloalkyl, aralkyl, mono or polyhydric alcohol ester of any alkanoic, cycloalkanoic, aryl or aralkyl carboxylic acid. In the catalyst, iron, cobalt or nickel may be used as free metal, or as a compound, e.g. carbonyl, acetate, or halide. The halogen may also be free or in the form of an inorganic salt or organic halide, such as methyl or ethyl iodide. A combination of nickel and iodine, either as free elements, as nickel iodide, or a combination of, e.g., nickel acetate or carbonyl with bismuth iodide, cuprous iodide or hydrogen iodide, is preferred. According to examples: (a) acetic acid, with methyl acetate as by-product, is produced by reaction of methanol, dimethyl ether, or methyl acetate with carbon monoxide and water, in a titanium-lined reactor, using as catalyst nickel iodide, nickel chloride, or nickel bromide, or a combination of nickel acetate, nickel carbonyl, nickel powder or cobalt acetate with methyl iodide, or nickel acetate with iodine; (b) pentene-1 is similarly converted to 2-methyl-pentanoic acid and n-hexanoic acid, and hexenes are converted to heptanoic acids, using nickel acetate-hydriodic acid as catalyst; (c) camphene is similarly converted to an acid using nickel iodide and bismuth triiodide as catalyst; (d) using a platinum-lined reactor in which strips of zirconium are hung, methanol is reacted with carbon monoxide and water, using a nickel iodide catalyst, to give acetic acid. Specification 628,161 is referred to.ALSO:A reactor, the inner surfaces of which consist of, or which is lined with, a metal containing at least 90 per cent titanium or zirconium is used for the synthesis of organic carboxylic acids by the catalytic addition of carbon monoxide to an alcohol, or of carbon monoxide and water to an olefin, ether or carboxylic acid ester, in the presence of a catalyst containing an element of the iron subgroup and chlorine, bromine or iodine, at a temperature of 200 DEG to 350 DEG C. and a pressure of 2000 to 15,000 p.s.i. Titanium and zirconium are resistant to the highly corrosive conditions of these syntheses. All parts of the apparatus coming into direct contact with the reactants or products at high temperatures and pressures are made of, plated with, or inner-lined with a metal containing at least 90 per cent titanium or zirconium. Such a plating or inner lining may be held in place by other materials capable of withstanding the temperature and pressure.
GB1742453A 1953-06-23 1953-06-23 Improvements in or relating to synthesis of carboxylic acids Expired GB743933A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1742453A GB743933A (en) 1953-06-23 1953-06-23 Improvements in or relating to synthesis of carboxylic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1742453A GB743933A (en) 1953-06-23 1953-06-23 Improvements in or relating to synthesis of carboxylic acids

Publications (1)

Publication Number Publication Date
GB743933A true GB743933A (en) 1956-01-25

Family

ID=10094963

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1742453A Expired GB743933A (en) 1953-06-23 1953-06-23 Improvements in or relating to synthesis of carboxylic acids

Country Status (1)

Country Link
GB (1) GB743933A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2417491A1 (en) * 1978-02-20 1979-09-14 Mitsubishi Gas Chemical Co METHOD AND APPARATUS FOR THE PREPARATION OF A HIGH PURITY TEREPHTHALIC ACID

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2417491A1 (en) * 1978-02-20 1979-09-14 Mitsubishi Gas Chemical Co METHOD AND APPARATUS FOR THE PREPARATION OF A HIGH PURITY TEREPHTHALIC ACID

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