GB1101056A - The production of esters, aldehydes, ketones and acids - Google Patents

The production of esters, aldehydes, ketones and acids

Info

Publication number
GB1101056A
GB1101056A GB6093/64A GB609364A GB1101056A GB 1101056 A GB1101056 A GB 1101056A GB 6093/64 A GB6093/64 A GB 6093/64A GB 609364 A GB609364 A GB 609364A GB 1101056 A GB1101056 A GB 1101056A
Authority
GB
United Kingdom
Prior art keywords
acetate
acrolein
allyl
palladium
acids
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
GB6093/64A
Inventor
Duncan CLARK
Percy Hayden
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB6093/64A priority Critical patent/GB1101056A/en
Priority to DE19651543047 priority patent/DE1543047B1/en
Priority to NL6501827A priority patent/NL6501827A/xx
Priority to BE659698A priority patent/BE659698A/xx
Priority to FR5449A priority patent/FR1431939A/en
Priority to ES0309338A priority patent/ES309338A1/en
Publication of GB1101056A publication Critical patent/GB1101056A/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
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
    • 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
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
    • C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds

Landscapes

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

Abstract

Unsaturated aldehydes, ketones and acids and esters of unsaturated alcohols with carboxylic acids are prepared by contacting an unsaturated compound <FORM:1101056/C2/1> in which each R1, R2, R3 and R4 is a hydrogen atom or a saturated alkyl (not more than 8C), or any two of R1, R2, R3 and R4 are combined as a divalent saturated alkyl group, and Y is an acyloxy, aroyloxy or hydroxy group or a chlorine or bromine atom, with a palladium salt in the presence of an aliphatic carboxylic acid containing between 2 and 10 carbon atoms, molecular oxygen and a salt of copper or iron either under anhydrous conditions or in the presence of not more than 20% of water, any halide ions present being chlorine or bromine ions in concentration not exceeding 0.35 molar. Palladium acetate, or preferably a palladium halide may be used and preferably carboxylate (2-10 C) ions are present additional to those provided by the ionization of the carboxylic acid. Processes mentioned use allyl acetate to yield allylidene diacetate which may be hydrolysed to acrolein, and allyl chloride or allyl alcohol to form acrolein; methylallyl acetate to prepare methacrolein; crotyl acetate to form crotonaldehyde; a -methyl allyl acetate to form methyl vinyl ketone; g -ethyl allyl acetate to form b -ethyl acrolein; and 1-cyclohexene-3-acetate to form 1-cyclohexen-3-one. Mixed products may be formed depending upon the reaction conditions. Examples describe the preparation of mixed products allylidene diacetate, acrolein, and propylene 1-acetate.
GB6093/64A 1964-02-13 1964-02-13 The production of esters, aldehydes, ketones and acids Expired GB1101056A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB6093/64A GB1101056A (en) 1964-02-13 1964-02-13 The production of esters, aldehydes, ketones and acids
DE19651543047 DE1543047B1 (en) 1964-02-13 1965-02-12 Process for the preparation of unsaturated aldehydes, unsaturated ketones, unsaturated carboxylic acids and diesters of unsaturated dihydric alcohols with saturated carboxylic acids
NL6501827A NL6501827A (en) 1964-02-13 1965-02-12
BE659698A BE659698A (en) 1964-02-13 1965-02-12
FR5449A FR1431939A (en) 1964-02-13 1965-02-12 Process for the production of esters, aldehydes, ketones and acids
ES0309338A ES309338A1 (en) 1964-02-13 1965-02-13 The production of esters, aldehydes, ketones and acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB6093/64A GB1101056A (en) 1964-02-13 1964-02-13 The production of esters, aldehydes, ketones and acids

Publications (1)

Publication Number Publication Date
GB1101056A true GB1101056A (en) 1968-01-31

Family

ID=9808247

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6093/64A Expired GB1101056A (en) 1964-02-13 1964-02-13 The production of esters, aldehydes, ketones and acids

Country Status (5)

Country Link
BE (1) BE659698A (en)
DE (1) DE1543047B1 (en)
ES (1) ES309338A1 (en)
GB (1) GB1101056A (en)
NL (1) NL6501827A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3968164A (en) * 1966-04-07 1976-07-06 Imperial Chemical Industries Limited Process for the production of acrolein

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE618071A (en) *
DE1059453B (en) * 1957-09-06 1959-06-18 Consortium Elektrochem Ind Process for the preparation of carbonyl compounds from oxygen-containing organic compounds containing one or more carbon-carbon double bonds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3968164A (en) * 1966-04-07 1976-07-06 Imperial Chemical Industries Limited Process for the production of acrolein

Also Published As

Publication number Publication date
ES309338A1 (en) 1965-12-16
NL6501827A (en) 1965-08-16
DE1543047B1 (en) 1970-06-04
BE659698A (en) 1965-08-12

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