GB761203A - Process for producing condensation products from saturated carbonyl-compounds - Google Patents

Process for producing condensation products from saturated carbonyl-compounds

Info

Publication number
GB761203A
GB761203A GB29204/54A GB2920454A GB761203A GB 761203 A GB761203 A GB 761203A GB 29204/54 A GB29204/54 A GB 29204/54A GB 2920454 A GB2920454 A GB 2920454A GB 761203 A GB761203 A GB 761203A
Authority
GB
United Kingdom
Prior art keywords
feeding
mixture
sodium hydroxide
hydroxide solution
butyraldehyde
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
GB29204/54A
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.)
Usines de Melle SA
Original Assignee
Usines de Melle SA
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 Usines de Melle SA filed Critical Usines de Melle SA
Publication of GB761203A publication Critical patent/GB761203A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C45/61—Preparation 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
    • C07C45/67—Preparation 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
    • C07C45/68—Preparation 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
    • C07C45/72—Preparation 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
    • C07C45/74—Preparation 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
    • 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
    • C07C45/61—Preparation 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
    • C07C45/62—Preparation 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 hydrogenation of carbon-to-carbon double or triple bonds
    • 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
    • C07C45/61—Preparation 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
    • C07C45/67—Preparation 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
    • C07C45/68—Preparation 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
    • C07C45/72—Preparation 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated 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

Aldols, ketols or unsaturated carbonyl compounds are obtained by the condensation of either a saturated carbonyl compound having 3 or more carbon atoms in the molecule or a mixture of two saturated carbonyl compounds, of which at least one has 3 or more carbon atoms, the process being carried out by feeding the starting materials into a stream of liquid consisting of water and from 1 to 300 gms/litre of sodium hydroxide or an equinormal amount of another inorganic alkaline condensation catalyst, the rate of flow of the stream in volumes per unit time being from 10 to 100 times the rate of feed of the initial carbonyl compounds and the stream being maintained in turbulent state at a substantially constant temperature until condensation is complete. Suitable inorganic condensation catalysts, in addition to sodium hydroxide, are other caustic alkalis, alkali metal carbonates and alkali metal cyanides. At operating temperatures in the range 0 DEG to 60 DEG C., an aldehyde or a mixture of aldehydes generally gives an aldol and a ketone or a mixture of two ketones or of a ketone and an aldehyde generally gives a ketol or aldol; at operating temperatures in the range 60 DEG to 150 DEG C. an aldehyde, a mixture of two aldehydes or a mixture of an aldehyde and a ketone gives an unsaturated carbonyl compound. In the examples (a) ethyl propyl acrolein is obtained by feeding butyraldehyde into a stream of sodium hydroxide solution; it may be hydrogenated to ethyl hexyl alcohol; (b) diacetone-alcohol is obtained by feeding acetone into sodium hydroxide solution; (c) methyl ethyl acrolein is obtained by feeding a mixture of butyraldehyde and acetaldehyde into sodium hydroxide solution; (d) butyraldol is obtained by feeding butyraldehyde into sodium hydroxide solution; (e) pentyl hexyl acrolein is obtained by feeding heptaldehyde into sodium hydroxide solution; (f) furfurylidene acetone is obtained by feeding a mixture of furfural and acetone into potassium hydroxide solution; and (g) 3-hepten-2-one is obtained by feeding a mixture of butyraldehyde and acetone into potassium hydroxide solution.
GB29204/54A 1953-10-16 1954-10-18 Process for producing condensation products from saturated carbonyl-compounds Expired GB761203A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR761203X 1953-10-16

Publications (1)

Publication Number Publication Date
GB761203A true GB761203A (en) 1956-11-14

Family

ID=9172225

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29204/54A Expired GB761203A (en) 1953-10-16 1954-10-18 Process for producing condensation products from saturated carbonyl-compounds

Country Status (1)

Country Link
GB (1) GB761203A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1149344B (en) * 1958-04-07 1963-05-30 Eastman Kodak Co Process for the production of alpha, ß-unsaturated, branched aliphatic aldehydes by aldol condensation
DE1176120B (en) * 1958-05-27 1964-08-20 Eastman Kodak Co Process for the purification of ª,ª-unsaturated aliphatic aldehydes
EP1106596A2 (en) * 1999-11-30 2001-06-13 Oxeno Olefinchemie GmbH Process to perform aldolcondensations using catalysed multiphase reactions
DE102009045139A1 (en) 2009-09-30 2011-03-31 Evonik Oxeno Gmbh Preparation of alpha, beta-unsaturated aldehydes by means of a reaction mixing pump
DE102011012846A1 (en) 2011-03-03 2012-09-06 Oxea Gmbh Process for carrying out multiphase aldol condensation reactions to give mixed α, β-unsaturated aldehydes

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1149344B (en) * 1958-04-07 1963-05-30 Eastman Kodak Co Process for the production of alpha, ß-unsaturated, branched aliphatic aldehydes by aldol condensation
DE1176120B (en) * 1958-05-27 1964-08-20 Eastman Kodak Co Process for the purification of ª,ª-unsaturated aliphatic aldehydes
EP1106596A2 (en) * 1999-11-30 2001-06-13 Oxeno Olefinchemie GmbH Process to perform aldolcondensations using catalysed multiphase reactions
EP1106596A3 (en) * 1999-11-30 2002-04-17 Oxeno Olefinchemie GmbH Process to perform aldolcondensations using catalysed multiphase reactions
CZ301057B6 (en) * 1999-11-30 2009-10-29 Evonik Oxeno Gmbh Process to perform catalytic aldol condensation using multiphase reaction in tube reactor
DE102009045139A1 (en) 2009-09-30 2011-03-31 Evonik Oxeno Gmbh Preparation of alpha, beta-unsaturated aldehydes by means of a reaction mixing pump
WO2011038957A1 (en) 2009-09-30 2011-04-07 Evonik Oxeno Gmbh PRODUCING α,β-UNSATURATED ALDEHYDES BY MEANS OF A REACTION MIXING PUMP
DE102011012846A1 (en) 2011-03-03 2012-09-06 Oxea Gmbh Process for carrying out multiphase aldol condensation reactions to give mixed α, β-unsaturated aldehydes
WO2012116775A2 (en) 2011-03-03 2012-09-07 Oxea Gmbh METHOD FOR CARRYING OUT MULTIPHASE ALDOL CONDENSATION REACTIONS TO OBTAIN MIXED α,β-UNSATURATED ALDEHYDES
US8841489B2 (en) 2011-03-03 2014-09-23 Oxea Gmbh Method for carrying out multiphase aldol condensation reactions to give mixed α, β-unsaturated aldehydes

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