GB664180A - The manufacture of 3,5,5-trimethylhexanoic acid - Google Patents

The manufacture of 3,5,5-trimethylhexanoic acid

Info

Publication number
GB664180A
GB664180A GB3336/49A GB333649A GB664180A GB 664180 A GB664180 A GB 664180A GB 3336/49 A GB3336/49 A GB 3336/49A GB 333649 A GB333649 A GB 333649A GB 664180 A GB664180 A GB 664180A
Authority
GB
United Kingdom
Prior art keywords
trimethylhexanol
acid
trimethylhexanoic acid
greases
thickeners
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
GB3336/49A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB664180A publication Critical patent/GB664180A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms
    • C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
    • 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
    • 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
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • C10M2209/062—Vinyl esters of saturated carboxylic or carbonic acids, e.g. vinyl acetate

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Catalysts (AREA)
  • Lubricants (AREA)

Abstract

A process for preparing 3,5,5-trimethylhexanoic acid comprises intimately mixing molecular oxygen with 3,5,5-trimethylhexanol at a temperature of 0 DEG to 100 DEG C. and continuing the resulting oxidation until 3,5,5-trimethylhexanoic acid is obtained. The preferred temperature range is 20 DEG to 75 DEG C. An organic peroxy compound is formed initially but this disappears gradually and 3,5,5-trimethylhexanoic acid is obtained in virtually p quantitative yield. Inorganic oxidation catalysts need not be employed but to carry out the reaction at the maximum rate oxidation catalysts such as compounds of cobalt, copper, vanadium, manganese, osmium and cerium may be employed though polycarboxylic acids may also be produced. In examples: (1) air is passed through 3,5,5-trimethylhexanol and the product is purified by distillation under reduced pressure; (2) 3,5,5-trimethylhexanol in acetic acid is oxidized by air in the presence of manganous acetate, the product is distilled and treated with aqueous alkali, extracted with ether and acidified and the desired product separated and again distilled. 3,5,5-Trimethylhexanol is obtained by heating diisobutylene in ether with carbon monoxide and hydrogen under pressure with a cobalt catalyst. 3,5,5-Trimethylhexanol-1 is also formed and is separated by distillation. 3,5,5 - Trimethylhexanoic acid may be esterified with monohydric or polyhdric alcohols, the polyvinyl ester being valuable as a lubricating oil thickener and the metallic salts as thickeners in greases (see Group III), as catalysts in organic salt type driers and as modifiers in alkyd resins. Specification 614,010 is referred to.ALSO:3, 5, 5-trimethyl-hexanoic acid, prepared by the oxidation of 3, 5, 5-trimethylhexanal (see Group IVb), may be employed in the form of the polyvinyl ester as a thickener for both naphthenic and paraffin base lubricating oils and the metallic salts of the acid may be used as thickeners in greases. Metal salts of caproic, caprylic and pelargonic acids are also stated to be suitable as thickeners for greases and their esters are stated to be of value as lubricants. Specification 614,010, [Group IV(b)], is referred to.
GB3336/49A 1948-02-25 1949-02-07 The manufacture of 3,5,5-trimethylhexanoic acid Expired GB664180A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US664180XA 1948-02-25 1948-02-25

Publications (1)

Publication Number Publication Date
GB664180A true GB664180A (en) 1952-01-02

Family

ID=22069366

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3336/49A Expired GB664180A (en) 1948-02-25 1949-02-07 The manufacture of 3,5,5-trimethylhexanoic acid

Country Status (1)

Country Link
GB (1) GB664180A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4199599A (en) * 1977-06-27 1980-04-22 Dragoco Gerberding & Co. Gmbh Glyceryl-tri-3,5,5-trimethylhexanoate protecting the skin therewith and cosmetic compositions therefore

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4199599A (en) * 1977-06-27 1980-04-22 Dragoco Gerberding & Co. Gmbh Glyceryl-tri-3,5,5-trimethylhexanoate protecting the skin therewith and cosmetic compositions therefore

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