GB759416A - Improvements relating to cleavage products of aliphatic compounds - Google Patents

Improvements relating to cleavage products of aliphatic compounds

Info

Publication number
GB759416A
GB759416A GB13706/54A GB1370654A GB759416A GB 759416 A GB759416 A GB 759416A GB 13706/54 A GB13706/54 A GB 13706/54A GB 1370654 A GB1370654 A GB 1370654A GB 759416 A GB759416 A GB 759416A
Authority
GB
United Kingdom
Prior art keywords
acid
acetoxy
give
lead
acetate
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
GB13706/54A
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.)
Baker Castor Oil Co
Original Assignee
Baker Castor Oil Co
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 Baker Castor Oil Co filed Critical Baker Castor Oil Co
Publication of GB759416A publication Critical patent/GB759416A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation
    • 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
    • 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
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/296—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with lead derivatives
    • 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
    • C07C45/673—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 change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • 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
    • 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
    • C07C51/373—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 doubly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/035—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with saturated hydrocarbons

Landscapes

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

Abstract

The invention comprises the new compounds 11 - acetoxy - 9 - undecenoic acid, methyl - 11 - acetoxy - 9 - undecenoate, 11 - hydroxy - 9- undecenoic acid, 1 - acetoxy - 9 - undecen - 1 - ol and 1.11-dihydroxy-9-undecene. They may be made, among other products, by reacting an aliphatic compound having a group <FORM:0759416/IV(a)/1> in which R is H, COOH or alkyl, R1 is H or alkyl and R11 is H, OH or alkyl, with a tetravalent lead salt of an aliphatic carboxylic acid having from 2 to 6 carbon atoms per molecule in the presence of a solvent. The lead salt may be prepared in situ from a lead compound and an aliphatic carboxylic acid having from 2 to 6 carbon atoms. Typical aliphatic compounds which may be used as starting materials are allyl carbinol, b -hydroxy propionaldehyde, hydracrylic acid, citric acid and the alkali metal salts, malic acid, citramalic acid, agaracinic acid, norcaperatic acid (n - C14H29CH(COOH)C(OH) (COOH)CH2COOH), b - hydroxybutyric acid, b -hydroxyvaleric acid, b -hydroxyisovaleric acid, b -acetylethyl alcohol, 2.5-hexanedion-3-ol, diacetone alcohol, methyl acetonyl, carbinol and aldol condensation products such as acetaldol and heptaldol. Castor oil and ricinoleyl derivatives, such as methyl ricinoleate, butyl ricinoleate, ricinoleic acid, ricinoleyl alcohol, ricinoleic acid salts and ricinoleic amide may also be used. Suitable tetravalent lead salts are those of acetic acid, propionic acid, pivalic acid and caproic acid. Suitable solvents are aliphatic carboxylic acids having from 2 to 6 carbon atoms, aromatic hydrocarbons, nitro aromatic hydrocarbons and chlorinated aliphatic hydrocarbons. The cleavage reaction takes place at temperatures from 10 DEG C. to 200 DEG C. In the examples (a) a solution of sodium citrate in acetic acid is heated with lead tetra-acetate to give a mixture of oxaloacetic acid and acetoxy acetic acid; (b) a solution of diacetone alcohol in acetic acid is treated with lead tetra-acetate to give acetone and acetoxyacetone; (c) a solution of heptaldol in benzene is treated with lead tetra-acetate to give heptaldehyde and a -acetoxy-heptaldehyde; (d) methyl ricinoleate is dissolved in acetic acid and treated with lead tetra-acetate to give heptaldehyde and methyl-11-acetoxy-9-undecenoate which on saponification gives 11-hydroxy-9-undecenoic acid and on oxidation with potassium permanganate give azelaic acid; (e) methyl ricinoleate is dissolved in caproic acid and treated with lead tetracaproate to give heptaldehyde and methyl-11 - acetoxy - 9 - undecenoate; (f) ricinoleyl alcohol dissolved in acetic acid is treated with lead tetra-acetate to give heptaldehyde and 11-acetoxy - 9 - undecene - 1 - ol which on saponification gives 1.11-dihydroxy-9-undecene; (g) castor oil is treated with lead tetra-acetate in acetic acid to give heptaldehyde and glycery tri - (11 - acetoxy - 9 - undecenoate); (h) the butyl ester of castor oil fatty acids is reacted with lead tetra-acetate in acetic acid to give heptaldehyde and butyl-11-acetoxy-9-undecenate; (j) castor oil fatty acids are treated with lead tetra acetate in acetic acid to give 11-acetoxy-9-undecenoic acid; and (k) methyl ricinoleate is treated with lead tetra-acetate using benzene and dichlorethylene as solvents to give heptaldehyde and methyl-11-acetoxy-9-undecenoate. The lead tetra-acetate used is prepared by adding red lead to a mixture of glacial acetic acid and acetic anhydride and heating.
GB13706/54A 1953-07-31 1954-05-11 Improvements relating to cleavage products of aliphatic compounds Expired GB759416A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US371711A US2790824A (en) 1953-07-31 1953-07-31 Oxidation of hydroxyl-containing aliphatic compounds

Publications (1)

Publication Number Publication Date
GB759416A true GB759416A (en) 1956-10-17

Family

ID=23465104

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13706/54A Expired GB759416A (en) 1953-07-31 1954-05-11 Improvements relating to cleavage products of aliphatic compounds

Country Status (3)

Country Link
US (1) US2790824A (en)
GB (1) GB759416A (en)
NL (2) NL187897B (en)

Also Published As

Publication number Publication date
US2790824A (en) 1957-04-30
NL88892C (en) 1958-07-16
NL187897B (en) 1958-03-15

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