GB775017A - Synthetic ester lubricants and lubricating compositions therefrom - Google Patents

Synthetic ester lubricants and lubricating compositions therefrom

Info

Publication number
GB775017A
GB775017A GB1020154A GB1020154A GB775017A GB 775017 A GB775017 A GB 775017A GB 1020154 A GB1020154 A GB 1020154A GB 1020154 A GB1020154 A GB 1020154A GB 775017 A GB775017 A GB 775017A
Authority
GB
United Kingdom
Prior art keywords
acid fraction
fraction
wax
oxidation
oxidized
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
GB1020154A
Inventor
George Gamble Evans
Hans Christian Henry Jensen
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering 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 Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Priority to GB1020154A priority Critical patent/GB775017A/en
Publication of GB775017A publication Critical patent/GB775017A/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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/34—Esters of monocarboxylic 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
    • C10M2207/28—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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated 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
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C10M2209/112—Complex polyesters having dihydric acid centres
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

The invention comprises an oleaginous fluid obtained by oxidizing a paraffin wax to obtain an acid fraction comprising C12-C26 acids and a non-acidic oxidized fraction, extracting the said acid fraction from the oxidized wax, and esterifying the said acid fraction with a saturated aliphatic alcohol. The oxidation may be effected by blowing the wax with air, preferably at elevated temperature and in the presence of an oxidation catalyst. If carried out for a sufficient length of time, the oxidation will result not only in the production of the said acid fraction but will also result in a complex mixture of esters, lactones and lactides which is difficult to hydrolyse. The acid fraction may be readily extracted by dissolving the total oxidized product in an organic solvent and extracting the acid portion with an alkaline agent, e.g. aqueous sodium carbonate. The acid fraction is released from the extract by acidification. The saturated aliphatic alcohols used for the esterification preferably contain 4 to 20 carbon atoms and have some branching of their chains. The oxo alcohols are particularly suitable. The esterification is preferably conducted at elevated temperature in the presence of an esterification catalyst such as sodium bisulphate and a water entrainer. The resulting ester may be refined by treating with an inorganic base and washing to give a product of residual acidity less than 1 milligram KOH/g. The yield of the esterified acids may be increased by adding selected alcohols or glycols to the wax during oxidation. In an example, a charge of slack wax and cobalt naphthenate is blown with air for 48 hours at 120 DEG C., the oxidized product is dissolved in ethyl acetate and extracted with an aqueous solution of sodium carbonate, the extract is acidified and the acid fraction so obtained is esterified with 2-ethylhexanol. The product is useful as a lubricant and as a component in lubricating compositions. The non-acid fraction may also be used as a lubricant. The Provisional Specification refers also to the use of predominantly paraffin, i.e. hydrocarbons having a molecular weight corresponding to more than 12 carbon atoms as starting materials for the oxidation. Naphthenic hydrocarbons having paraffinic side chains are also mentioned.ALSO:Lubricating compositions comprise an oleaginous fluid, obtained (see Group IV(b)) by oxidizing a paraffin wax to obtain a C12-C26 acid fraction and a nonacidic oxidized fraction, extracting the acid fraction, and esterifying said acid fraction with a saturated aliphatic alcohol, blended with a mineral oil, a diester or complex ester, or a glycol ether. The saturated aliphatic alcohol is preferably a branched-chain C4-C20 alcohol such as an oxo alcohol. The lubricating compositions may also contain oxidation inhibitors such as phenols or alkylated phenols, organic sulphur and/or phosphorus-containing compounds, or amines, e.g. phospho-sulphurized hydrocarbons, particularly terpenes, and phenothiazine. The non-acidic oxidized fraction may also be used in lubricating compositions similar to those described for the esterified acid fraction. Exemplified compositions comprise an ester product, obtained by oxidizing slack wax and esterifying the extracted acidic fraction with 2 - ethyl hexanol, together with di-octyl sebacate or di-nonyl sebacate.
GB1020154A 1954-04-07 1954-04-07 Synthetic ester lubricants and lubricating compositions therefrom Expired GB775017A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1020154A GB775017A (en) 1954-04-07 1954-04-07 Synthetic ester lubricants and lubricating compositions therefrom

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1020154A GB775017A (en) 1954-04-07 1954-04-07 Synthetic ester lubricants and lubricating compositions therefrom

Publications (1)

Publication Number Publication Date
GB775017A true GB775017A (en) 1957-05-15

Family

ID=9963440

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1020154A Expired GB775017A (en) 1954-04-07 1954-04-07 Synthetic ester lubricants and lubricating compositions therefrom

Country Status (1)

Country Link
GB (1) GB775017A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996015210A1 (en) * 1994-11-14 1996-05-23 Unichema Chemie B.V. Lubricant

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996015210A1 (en) * 1994-11-14 1996-05-23 Unichema Chemie B.V. Lubricant
US6008167A (en) * 1994-11-14 1999-12-28 Unilever Patent Holdings B.V. Lubricant
US6346504B1 (en) 1994-11-14 2002-02-12 Unilever Patent Holdings B.V. Lubricant

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