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GB687347A - Improved lubricant blend - Google Patents

Improved lubricant blend

Info

Publication number
GB687347A
GB687347A GB7473/49A GB747349A GB687347A GB 687347 A GB687347 A GB 687347A GB 7473/49 A GB7473/49 A GB 7473/49A GB 747349 A GB747349 A GB 747349A GB 687347 A GB687347 A GB 687347A
Authority
GB
United Kingdom
Prior art keywords
alcohol
glycol
acid
ester
acids
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
GB7473/49A
Inventor
Ronald William Morton
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.)
Standard Oil Development Co
Original Assignee
Standard Oil Development 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 Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to GB7473/49A priority Critical patent/GB687347A/en
Publication of GB687347A publication Critical patent/GB687347A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M3/00Liquid 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/08Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/30Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11Complex polyesters
    • C10M2209/112Complex polyesters having dihydric acid centres
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08Resistance to extreme temperature
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/12Gas-turbines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/12Gas-turbines
    • C10N2040/13Aircraft turbines

Landscapes

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

Abstract

Ester blends are prepared by reacting together in one or more stages and in the presence of an esterification catalyst if necessary, an aliphatic dicarboxylic acid or acids or esterifying equivalent, an aliphatic glycol or glycols, polyglycol or polyglycols or esterifying equivalent and an aliphatic alcohol or alcohols or esterifying equivalent in appropriate proportions adapted to yield after the final esterifying stage a mixture of a complex ester of general formula R1-OOC-R2-COO-R3-OOC-R4-COOR5, and the alcohol diester or diesters of the dicarboxylic acid or acids, R1 and R5 representing the alcohol (including ether alcohol) residues, R2 and R4 representing the hydrocarbon radicals of the acid or acids, and R3 representing the hydrocarbon or oxahydrocarbon radical of the glycol or glycols, all the radicals R1 to R5 being saturated and the total number of carbon atoms in the complex ester being from 20 to 100, preferably from 30 to 60. The preferred starting materials are the acids, glycols and alcohols used in presence of an esterification catalyst, but there may also be used alkali metal salts of the acids and halogen derivatives of the alcohol and glycol or the acid chlorides and alkali metal derivatives of the alcohol and glycol. The components may be reacted in several ways; thus all three may be refluxed together; the glycol may be reacted with the acid in a first stage to form a mixture of glycol half-ester and free acid, which mixture is then esterified with the alcohol; the alcohol may be reacted with the acid in a first stage to form a mixture of diester and alcohol half-ester, which mixture is then esterified with the glycol, and in these methods the preferred mol, ratio of the acid, alcohol and glycol starting materials are 2+n : 2+2n : 1 where n : 1 is the desired molar ratio of diester to complex ester in the blend; or the glycol, glycols, polyglycol or polyglycols may be reacted in the presence of an esterification catalyst with more than 2 molar proportions of an alkyl di-ester of a dicarboxylic acid whereby the blend of complex ester and diester is obtained in which connection, Specification 683,803 is referred to. Preferably, the blend contains a minor proportion of the diester. The processes may be artificially broken down to any number of desired stages; for example, half of the glycol may be esterified with all the acid, half the alcohol added in a second stage, the remainder of the glycol in a third and the remainder of the alcohol in a fourth stage. Suitable starting materials are C1 to C12 alkanols or mixtures thereof, e.g. iso-octanol, oxo-nonanol or other oxo-fractions, C6 to C20 acids or mixtures thereof, e.g. polymethylene succinic acids such as adipic or sebacic acid, C4 to C24 polyglycols such as tri- or tetra-ethylene glycol. Ester blends are described obtained by the one stage method or glycol half-ester method, water of esterification being removed by means of toluene as an entrainer, from (1) 2 mols. each of 2-ethyl hexanol and oxo-nonanol, 3 mols sebacic acid and one mol. polyglycol 200; (2) oxo-nonanol, sebacic acid and polyglycol 200, yielding blends containing 64 and 73 per cent complex ester; (3) nonanol, 2-ethyl-hexanol, sebacic acid and polyglycol 200, the resulting blend containing 79 per cent complex ester; (4) nonanol, capryl alcohol, sebacic acid and polyglycol 200, the resulting blend containing 81 per cent complex esters; the blends are compared with similar blends prepared by mixing the complex ester with the diester. Specifications 666,697, 683,803, and 687,346, [Group III], are referred to.ALSO:Lubricant ester blends for use, e.g. in aviation turbines, are prepared by reacting together in one or more stages in the presence of an esterification catalyst if necessary, an aliphatic dicarboxylic acid or acids or esterifying equivalent, an aliphatic glycol or glycols, polyglycol or polyglycols or esterifying equivalent and an aliphatic alcohol or alcohols or esterifying equivalent in appropriate proportions adapted to yield after the final esterifying stage a mixture of complex ester, of the general formula R1-OOOC-R2-COO-R3-OOC-R4-COO R5, and the alcohol diester or diesters of the dicarboxylic acid or acids, R1 and R5 being the alcohol (including ether alcohol) residues, R2 and R4 being the hydrocarbon radicals of the acid or acids, and R3 being the hydrocarbon or oxahydrocarbon radical of the glycol or glycols, all the radicals R1 to R5 being saturated and the total number of carbon atoms in the complex ester being from 20 to 100, preferably from 30 to 60. Several methods of effecting the preparation of the blends are described, (see Group IV(b)). The reactants are preferably used in the mol ratio of acid: alcohol:glycol of 2+n:2+n:1 where n:1 is the desired molar ratio of diester to complex ester in the blend; the diester preferably constitutes a minor proportion of the blend. Suitable starting materials are C1 to C12 alkanols or mixtures thereof, e.g. 2-ethyl hexanol, iso-octanol and oxo-nonanol or other oxo-fractions, C6 to C20 acids or mixtures thereof, e.g. polymethylene succinic acids such as adipic or sebacic, and C4 to C24 polyglycols, e.g. tri-and tetra-ethylene glycols. Blends are described obtained from (1) 2-ethyl-hexanol, oxo-nonanol, polyglycol 200 and sebacic acid, the blend containing 64 per cent complex ester; (2) oxo-nonanol, sebacic acid and polyglycol 200, blends being formed containing 64 and 73 per cent complex ester; (3) nonanol, 2-ethyl-hexanol, sebacic acid and polyglycol 200, the complex ester content being 79 per cent; (4) nonanol, capryl alcohol, sebacic acid and polyglycol 200, the complex ester content being 81 per cent. These blends are compared with those obtained by mixing the complex ester with the diester. Specifications 666,697, 683,803 and 687,346 are referred to.
GB7473/49A 1949-03-18 1949-03-18 Improved lubricant blend Expired GB687347A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB7473/49A GB687347A (en) 1949-03-18 1949-03-18 Improved lubricant blend

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB7473/49A GB687347A (en) 1949-03-18 1949-03-18 Improved lubricant blend

Publications (1)

Publication Number Publication Date
GB687347A true GB687347A (en) 1953-02-11

Family

ID=9833777

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7473/49A Expired GB687347A (en) 1949-03-18 1949-03-18 Improved lubricant blend

Country Status (1)

Country Link
GB (1) GB687347A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2937996A (en) * 1955-03-04 1960-05-24 British Petroleum Co Synthetic lubricants
US2956954A (en) * 1955-07-11 1960-10-18 Exxon Research Engineering Co Synthetic ester lubricants
US3016353A (en) * 1954-12-15 1962-01-09 Exxon Research Engineering Co Ester type synthetic lubricants

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3016353A (en) * 1954-12-15 1962-01-09 Exxon Research Engineering Co Ester type synthetic lubricants
US2937996A (en) * 1955-03-04 1960-05-24 British Petroleum Co Synthetic lubricants
US2956954A (en) * 1955-07-11 1960-10-18 Exxon Research Engineering Co Synthetic ester lubricants

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