GB446026A - Improvements in the production of aliphatic organic compounds - Google Patents

Improvements in the production of aliphatic organic compounds

Info

Publication number
GB446026A
GB446026A GB36660/34A GB3666034A GB446026A GB 446026 A GB446026 A GB 446026A GB 36660/34 A GB36660/34 A GB 36660/34A GB 3666034 A GB3666034 A GB 3666034A GB 446026 A GB446026 A GB 446026A
Authority
GB
United Kingdom
Prior art keywords
product
ethylpropylacrolein
ethylhexaldehyde
methylisobutylketone
sulphated
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
GB36660/34A
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.)
Carbide and Carbon Chemicals Corp
Original Assignee
Carbide and Carbon Chemicals Corp
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 Carbide and Carbon Chemicals Corp filed Critical Carbide and Carbon Chemicals Corp
Publication of GB446026A publication Critical patent/GB446026A/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
    • 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
    • C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration

Landscapes

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

Abstract

Methylisobutylketone is condensed with an aliphatic aldehyde having at least eight carbon atoms to form a ketol, which may then be dehydrated to give an unsaturated ketone, e.g. by heating after acidification. By reduction, the corresponding saturated ketone is first produced and by further reduction a secondary alcohol which may be sulphated to give, in the form of an alkali metal or alkaline earth metal salt, a detergent. In an example, methylisobutylketone is condensed in the presence of methanol or ethanol with ethylhexaldehyde and the resulting ketol converted into the unsaturated ketone. The latter is heated with hydrogen under pressure using nickel, copper, platinum, palladium or copper chromite as catalyst whereby a product is obtained which on fractionation yields 7-ethyl-2-methylundecanone-4 and 7-ethyl-2-methylundecanol-4. The latter is sulphated with sulphuric acid and acetic anhydride, the neutralized product taken up in methanol and extracted with hexane after the addition of water. The aqueous methanol solution is finally evaporated. For the sulphonation, diluents such as dichlorethyl-ether or carbon tetrachloride may be used and other sulphonating agents. The use of ethylpropylacrolein instead of ethylhexaldehyde is mentioned, in which case 7-ethyl-2-methylundecadiene-5 : 7-one-4 is obtained as the unsaturated ketone. This is reduced to give the corresponding saturated ketone and secondary tetradecyl alcohol, the latter being sulphated to produce the detergent. The use of the product in the textile and leather industries as wetting, impregnating, foaming and emulsifying agents is mentioned. Methylisobutylketone may be prepared by dehydrating diacetone alcohol and hydrogenating the product. Ethylpropylacrolein may be prepared by forming an aldol from butyraldehyde and dehydrating. Ethylhexaldehyde may be prepared by hydrogenating ethylpropylacrolein.
GB36660/34A 1934-01-05 1934-12-21 Improvements in the production of aliphatic organic compounds Expired GB446026A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US446026XA 1934-01-05 1934-01-05

Publications (1)

Publication Number Publication Date
GB446026A true GB446026A (en) 1936-04-23

Family

ID=21933274

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36660/34A Expired GB446026A (en) 1934-01-05 1934-12-21 Improvements in the production of aliphatic organic compounds

Country Status (1)

Country Link
GB (1) GB446026A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0919532A1 (en) * 1997-11-29 1999-06-02 Celanese GmbH Process for the preparation of saturated alcohols
US6960694B2 (en) 2003-07-01 2005-11-01 Eastman Chemical Company Processes for preparing β-hydroxy-ketones and α,β-unsaturated ketones
US7071361B2 (en) 2004-06-25 2006-07-04 Fastman Chemical Company Processes for the preparation of high molecular weight saturated ketones

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0919532A1 (en) * 1997-11-29 1999-06-02 Celanese GmbH Process for the preparation of saturated alcohols
US6288288B1 (en) 1997-11-29 2001-09-11 Celanese Gmbh Process for preparing saturated alcohols
US6960694B2 (en) 2003-07-01 2005-11-01 Eastman Chemical Company Processes for preparing β-hydroxy-ketones and α,β-unsaturated ketones
US7071361B2 (en) 2004-06-25 2006-07-04 Fastman Chemical Company Processes for the preparation of high molecular weight saturated ketones

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