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GB779391A - Improvements in 2, 5-dimethyl-1, 6-hexanediol and esters thereof - Google Patents

Improvements in 2, 5-dimethyl-1, 6-hexanediol and esters thereof

Info

Publication number
GB779391A
GB779391A GB22904/55A GB2290455A GB779391A GB 779391 A GB779391 A GB 779391A GB 22904/55 A GB22904/55 A GB 22904/55A GB 2290455 A GB2290455 A GB 2290455A GB 779391 A GB779391 A GB 779391A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
acid
hexane diol
give
carbon atoms
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
GB22904/55A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas 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 Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB779391A publication Critical patent/GB779391A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • 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
    • C07C29/147—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 carboxylic acids or derivatives thereof
    • C07C29/149—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 carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • 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
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • 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
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The esters of 2.5-dimethyl-1.6-hexane diol with straight-chained alkanoic acids of four to twelve carbon atoms are stated to be excellent low-temperature plasticizers for polyvinyl chloride and like polymers and copolymers. Polyesters are formed by reaction between 2.5-dimethyl-1.6-hexane diol and dicarboxylic acids such as succinic, adipic, dimethyladipic, pimelic, azelaic, sebacic and the various phthalic acids.ALSO:The invention comprises esters of formula <FORM:0779391/IV(b)/1> in which R DEG is the acyl group of a straight-chained saturated aliphatic monocarboxylic acid of four to twelve carbon atoms. 2.5-Dimethyl-1.6-hexane diol, from which these esters are derived, is prepared by reacting an alkyl ester of a .a 1-dimethyl adipic acid, in which the alkyl group contains from 1 to 4 carbon atoms, with hydrogen under pressure in the presence of a copperchromium oxide hydrogenation catalyst between 200 DEG and 350 DEG C. The diol may then be heated with a straight-chained alkanoic acid, containing from four to twelve carbon atoms, in the presence of an acidic esterification catalyst and a water-immiscible volatile organic solvent to produce an ester with the above formula. The hydrogenation is carried out at temperatures of 200-350 DEG C. and a hydrogen pressure of 1500-2500 p.s.i. Suitable esterification catalysts are, for example, sulphuric acid, a sulphonated cation-exchange resin in hydrogen form, an arylsulphonic acid or an alkane sulphonic acid. Suitable solvents are benzene, toluene, xylene, chlorinated hydrocarbons and naphthas. In the examples: (a) dimethyl-a -a 1-dimethyl adipate is treated with hydrogen in the presence of a copper-chromium oxide catalyst to give 2.5-dimethyl-1.6-hexane diol; (b) 2.5-dimethyl-1.6-hexane diol is heated with butyric acid in the presence of p-toluene sulphonic acid and toluene to give the ester of formula C3H7COOCH2CH(CH3)CH2CH2CH (CH3)CH2COOC3H7; (c) 2.5-dimethyl-1.6-hexane diol is reacted with caprylic acid to give the di-octanoate; (d) 2.5-dimethyl-1.6-hexane diol is reacted with lauric acid to give the di-laurate and (e) 2.5-dimethyl-1.6-hexane diol is reacted with caproic acid and butyric acid to give the half butyrate half caproate.ALSO:The esters of 2.5 - dimethyl - 1.6 - hexane diol with straight-chained alkanoic acids of four to twelve carbon atoms may be used as liquid lubricants and may be made into greases with lithium stearate. The oils and greases may contain anti-oxidants, stabilizers, E.P. agents, and corrosion inhibitors. They may also contain oil-soluble resinous products which are used to depress pour point and improve viscosity index, such as alkyl polymethacrylates, polyacrylates, polyfumarates or polyitaconates, and copolymers from two or more polymerizable monovinylidene compounds.
GB22904/55A 1954-08-13 1955-08-09 Improvements in 2, 5-dimethyl-1, 6-hexanediol and esters thereof Expired GB779391A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US779391XA 1954-08-13 1954-08-13

Publications (1)

Publication Number Publication Date
GB779391A true GB779391A (en) 1957-07-17

Family

ID=22140911

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22904/55A Expired GB779391A (en) 1954-08-13 1955-08-09 Improvements in 2, 5-dimethyl-1, 6-hexanediol and esters thereof

Country Status (3)

Country Link
FR (1) FR1128860A (en)
GB (1) GB779391A (en)
NL (2) NL199446A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023111143A1 (en) * 2021-12-16 2023-06-22 Totalenergies Onetech Process for producing diesters, and diesters obtained thereby

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023111143A1 (en) * 2021-12-16 2023-06-22 Totalenergies Onetech Process for producing diesters, and diesters obtained thereby
FR3130798A1 (en) * 2021-12-16 2023-06-23 Totalenergies Marketing Services METHOD FOR MANUFACTURING DIESTERS AND DIESTERS THUS OBTAINED

Also Published As

Publication number Publication date
NL92698C (en)
NL199446A (en)
FR1128860A (en) 1957-01-11

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