GB794344A - Production of mesityl oxide and like ª‡-ethylenically unsaturated ketones - Google Patents

Production of mesityl oxide and like ª‡-ethylenically unsaturated ketones

Info

Publication number
GB794344A
GB794344A GB29547/54A GB2954754A GB794344A GB 794344 A GB794344 A GB 794344A GB 29547/54 A GB29547/54 A GB 29547/54A GB 2954754 A GB2954754 A GB 2954754A GB 794344 A GB794344 A GB 794344A
Authority
GB
United Kingdom
Prior art keywords
ketone
distilled
acetone
mixture
mesityl oxide
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
GB29547/54A
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.)
DERIVES de l ACETYLENE S I D A
Original Assignee
DERIVES de l ACETYLENE S I D A
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 DERIVES de l ACETYLENE S I D A filed Critical DERIVES de l ACETYLENE S I D A
Publication of GB794344A publication Critical patent/GB794344A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

<PICT:0794344/IV (b)/1> a -Ethylenically unsaturated ketones are prepared by the dimeric condensation of a ketone having at least two a -hydrogen atoms with splitting off of water, by heating at a pressure of less than 10 kg/sq. cm., a single liquid phase constituted by a solution of the monomeric ketone in an alkaline aqueous and/or alcoholic medium containing substantially 0.005 to 2 per cent by weight of an alkali metal hydroxide based on the monomeric ketone, at a temperature of substantially 50 DEG to 150 DEG C. for a reaction time such as to yield a product in which more than 60 per cent of the converted ketone is in the form of the desired unsaturated dimer, the remainder of the converted ketone being in the form of higher condensation products. The reation is preferably effected in a closed vessel under at least the autogenous pressure, and for a reaction period at least 10 mins. The conversion of acetone to mesityl oxide is suitably carried out at 75-120 DEG C. with a reaction time of 15-60 mins. in the presence of 0.5 to 7 gms. of KOH per litre of acetone. The condensation mixture may be distilled to recover the resulting unsaturated ketone. Preferably, however, the mixture is allowed to stand at 0-20 DEG C., whereby part of the unchanged ketone is converted to the hydroxylated dimers. The further reacted mixture may then be neutralized and distilled to recover the hydroxylated dimer and the unsaturated ketone formed in the first stage. Alternatively, the further reacted mixture is distilled from an acid medium whereby the hydroxylated dimer is dehydrated to yield more of the unsaturated ketone. A continuous method is described comprising feeding acetone and alkaline catalyst solution through lines 1, 2 and pumps 3, 4 and a preheater 5 into a heated reactor 6 under desired pressure. The reacted mixture from the reactor may be distilled directly in column 8. Alternatively, the mixture is passed through a cooler 9 to a reaction chamber 10 at ordinary temperature wherein dimerization of unchanged acetone to diacetone-alcohol occurs. The reacted mixture is then treated in mixer 13 with a neutralizing amount or more of an acid, e.g. phosphoric acid and distilled in column 8. Unchanged acetone and solvent are removed overhead and recycled to reactor 6 and mesityl oxide with or without diacetone-alcohol is removed as bottoms with minor amounts of isophorone. Examples illustrate the continuous conversion of acetone to mesityl oxide at 100-150 DEG C. using pressures of 3-9 kg/sq.cm. and 0.1 to 1 per cent KOH in water, methanol or ethanol; in most cases, the product is allowed to stand at 10 DEG C. for 5 hours and then distilled from phosphoric acid to increase the yield of mesityl oxide. Another example describes the similar conversion of methyl ethyl ketone to give 3-methyl-heptene-3-one-5 and 3:4-dimethyl-hexene-3-One-2 and a minor amount of a C12 ethylene ketone. Specifications 616,740 and 733,650 are referred to.
GB29547/54A 1953-12-24 1954-10-13 Production of mesityl oxide and like ª‡-ethylenically unsaturated ketones Expired GB794344A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR794344X 1953-12-24

Publications (1)

Publication Number Publication Date
GB794344A true GB794344A (en) 1958-04-30

Family

ID=9234039

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29547/54A Expired GB794344A (en) 1953-12-24 1954-10-13 Production of mesityl oxide and like ª‡-ethylenically unsaturated ketones

Country Status (1)

Country Link
GB (1) GB794344A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2066604B1 (en) 2006-09-05 2015-06-03 E. I. du Pont de Nemours and Company Dehydrofluorination process to manufacture hydrofluoroolefins

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2066604B1 (en) 2006-09-05 2015-06-03 E. I. du Pont de Nemours and Company Dehydrofluorination process to manufacture hydrofluoroolefins

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