GB731917A - Manufacture of 2-ethyl-hexanal-(1) and 2-ethyl-hexanol-(1) - Google Patents

Manufacture of 2-ethyl-hexanal-(1) and 2-ethyl-hexanol-(1)

Info

Publication number
GB731917A
GB731917A GB1045151A GB1045151A GB731917A GB 731917 A GB731917 A GB 731917A GB 1045151 A GB1045151 A GB 1045151A GB 1045151 A GB1045151 A GB 1045151A GB 731917 A GB731917 A GB 731917A
Authority
GB
United Kingdom
Prior art keywords
ethyl
hexanol
mixture
hydrogenated
crotonaldehyde
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
GB1045151A
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.)
Individual
Original Assignee
Individual
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
Priority to FR1044689D priority Critical patent/FR1044689A/en
Application filed by Individual filed Critical Individual
Priority to GB1045151A priority patent/GB731917A/en
Publication of GB731917A publication Critical patent/GB731917A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/175—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo 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
    • C07C45/61—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
    • C07C45/73—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 hydrogenation
    • 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

Landscapes

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

Abstract

2-Ethyl-hexanal-1 and 2-ethyl-hexanol-1 are obtained by hydrogenation of crotonaldehyde, condensation of the butyraldehyde formed with caustic alkali so as to obtain 2-ethyl-hexenal-1 and subsequent catalytic hydrogenation, the reaction stages being carried out discontinuously or continuously without isolation of the individual organic intermediate products. 2-Ethyl-hexanol-1 may be obtained by first hydrogenating the 2-ethyl-hexenal-1, formed as intermediate product, to 2-ethyl-hexanal-1 and then hydrogenating this until 2-ethyl-hexanol-1 is obtained. It is particularly advantageous to carry out this last hydrogenation in the gaseous phase after the separation of the aqueous phase and of the catalyst present up to that point. In the examples: (a) crotonaldehyde is hydrogenated in the presence of calcium carbonate nickel catalyst and kieselguhr and oleyl-methyl-tauride as emulsifying agent; caustic soda is then added with heating and the hydrogen pressure is raised; a mixture containing 2-ethyl-hexanol-1 and some butanol is obtained; (b) crotonaldehyde together with a nickel catalyst, oleyl-sarcoside, as emulsifying agent, and water are treated with hydrogen; caustic soda is then added and the mixture is then hydrogenated again to give 2-ethyl-hexanol-1; if 2-ethyl-hexanal-1 is required the 2nd hydrogenation is carried out at a lower temperature; (c) a mixture of crotonaldehyde, water and calcium carbonate is hydrogenated in the presence of a catalyst consisting of nickel on a carrier in a paste with ethyl-hexanol-1; a small amount of the sodium salt of oleylmethyl-tauride is added as emulsifier; the resulting mixture is treated with caustic soda; the temperature is raised and the mixture is hydrogenated to give a mixture containing ethyl-hexanol-1 and some butanol; (d) crotonaldehyde is hydrogenated in the presence of calcium carbonate and active nickel on a carrier in the absence or otherwise of an indifferent solvent; the resulting mixture consisting mainly of butyraldehyde is run into a vessel in the absence of air and caustic soda p solution is added; the mixture is then hydrogenated to give a mixture containing ethyl-hexanol-1 and some butanol; (e) crude ethyl-hexanal prepared by the process previously described on hydrogenation gives a mixture containing chiefly ethyl hexanol and some butanol.
GB1045151A 1951-05-03 1951-05-03 Manufacture of 2-ethyl-hexanal-(1) and 2-ethyl-hexanol-(1) Expired GB731917A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FR1044689D FR1044689A (en) 1951-05-03 1951-05-02 Process for the preparation of 2-ethylhexanal- (1) or 2-ethylhexanol- (1) and products obtained by this process
GB1045151A GB731917A (en) 1951-05-03 1951-05-03 Manufacture of 2-ethyl-hexanal-(1) and 2-ethyl-hexanol-(1)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1045151A GB731917A (en) 1951-05-03 1951-05-03 Manufacture of 2-ethyl-hexanal-(1) and 2-ethyl-hexanol-(1)

Publications (1)

Publication Number Publication Date
GB731917A true GB731917A (en) 1955-06-15

Family

ID=9968104

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1045151A Expired GB731917A (en) 1951-05-03 1951-05-03 Manufacture of 2-ethyl-hexanal-(1) and 2-ethyl-hexanol-(1)

Country Status (2)

Country Link
FR (1) FR1044689A (en)
GB (1) GB731917A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1275042B (en) * 1963-05-31 1968-08-14 Kyowa Hakko Kogyo Kk Process for the production of saturated alcohols and carbonyl compounds
EP0487035A2 (en) * 1990-11-20 1992-05-27 Montell North America Inc. Process for the preparation of diethers
WO2000031011A1 (en) * 1998-11-25 2000-06-02 Imperial Chemical Industries Plc Aldol condensation
WO2002024621A1 (en) * 2000-09-20 2002-03-28 Cognis Deutschland Gmbh & Co. Kg Method for producing branched alcohols and/or hydrocarbons
CN104151138A (en) * 2014-08-13 2014-11-19 中国石油大学(华东) Process for producing alcohol type high-carbon organic solvent by using n-butanol and n-octanol residual liquid
CN118005493A (en) * 2024-04-10 2024-05-10 张家港市华昌新材料科技有限公司 Preparation method of 2-ethylhexanal, catalyst and preparation method thereof

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1275042B (en) * 1963-05-31 1968-08-14 Kyowa Hakko Kogyo Kk Process for the production of saturated alcohols and carbonyl compounds
EP0487035A2 (en) * 1990-11-20 1992-05-27 Montell North America Inc. Process for the preparation of diethers
EP0487035A3 (en) * 1990-11-20 1992-11-25 Himont Incorporated Process for the preparation of diethers
US5371299A (en) * 1990-11-20 1994-12-06 Himont Incorporated Process for the preparation of diethers
WO2000031011A1 (en) * 1998-11-25 2000-06-02 Imperial Chemical Industries Plc Aldol condensation
US6586636B2 (en) 1998-11-25 2003-07-01 Imperial Chemical Industries Plc Aldol condensation
WO2002024621A1 (en) * 2000-09-20 2002-03-28 Cognis Deutschland Gmbh & Co. Kg Method for producing branched alcohols and/or hydrocarbons
US7365235B2 (en) 2000-09-20 2008-04-29 Cognis Deutschland Gmbh & Co. Kg Processes for producing branched compounds via condensation and hydrogenation
CN104151138A (en) * 2014-08-13 2014-11-19 中国石油大学(华东) Process for producing alcohol type high-carbon organic solvent by using n-butanol and n-octanol residual liquid
CN104151138B (en) * 2014-08-13 2016-08-24 中国石油大学(华东) The technique that a kind of octyl alconyl residual liquid produces alcohols high-carbon organic solvent
CN118005493A (en) * 2024-04-10 2024-05-10 张家港市华昌新材料科技有限公司 Preparation method of 2-ethylhexanal, catalyst and preparation method thereof

Also Published As

Publication number Publication date
FR1044689A (en) 1953-11-19

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