GB664992A - Hydroxy ester derivatives of propylene oxide - Google Patents

Hydroxy ester derivatives of propylene oxide

Info

Publication number
GB664992A
GB664992A GB24925/48A GB2492548A GB664992A GB 664992 A GB664992 A GB 664992A GB 24925/48 A GB24925/48 A GB 24925/48A GB 2492548 A GB2492548 A GB 2492548A GB 664992 A GB664992 A GB 664992A
Authority
GB
United Kingdom
Prior art keywords
acid
propylene oxide
hydroxy
molecular
ester
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
GB24925/48A
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
Publication of GB664992A publication Critical patent/GB664992A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Injection Moulding Of Plastics Or The Like (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Hydroxy ester derivatives of propylene oxide suitable for use as lubricants are obtained by reacting from 10 to 48 molecular proportions of propylene oxide with one molecular proportion of an aliphatic ester of a hydroxy aliphatic carboxylic acid containing from 1 to 3 carboxyl groups and one or more hydroxyl groups. The terminal hydroxyl group of the product may be etherified or esterified. It is preferred to use from 10 to 30 and especially from 14 to 22 molecular proportions of the propylene oxide. The p hydrocarbon chain of the hydroxy acids may be saturated or unsaturated and the acids specified are glycollic acid, hydracrylic acid, hydroxybutyric acid, hydroxy caproic acid, lactic acid, malic acid, citric acid, hydroxy-stearic acid and ricinoleic acid. The esterifying radical may be a saturated or unsaturated hydrocarbon group and may contain hydroxyl groups as in the glyceryl radical. Other specified radicals are ethyl, propyl, butyl, amyl, octyl, decyl, dodecyl, stearyl, oleyl and long-chain radicals derived from cracked paraffinic waxes. The preferred hydroxy acid esters are those having 2 to 20 carbon atoms in the acid radical and 1 to 20 carbon atoms in the ester group and the ester should preferably contain 1 to 4 hydroxyl groups per molecule. The reaction may be conducted at temperatures down to -10 DEG C. and metal halide catalysts such as boron fluoride and stannic chloride are generally required. In examples: (1) ethyl lactate (1 molecular proportion) is treated with propylene oxide (14 molecular proportions) in the presence of anhydrous SnCl4 in chloroform at 30 DEG C.; (2) di-n-butyl malate (1 molecular proportion) is reacted with propylene oxide 14 molecular proportions in the presence of BF3 at 35-45 DEG C.; (3) triethyl citrate and propylene oxide are reacted as in (2) except that the molecular proportion of propylene oxide to ester is 16 : 1; (4) castor oil (one molecular proportion) is reacted with 48 molecular proportions of propylene oxide in the presence of BF3 as in (2). The properties of the products as lubricants are given in each case. Specifications 312,523, [Class 2 (iii)], and 443,631 are referred to. The Specification as open to inspection under Sect. 91 refers to the use of any alkylene oxide in any molecular proportion and states that a hydroxy aliphatic carboxylic acid as well as the ester thereof may be treated. Ethylene oxide, isopropyl ethylene oxide, isobutylene oxide and butadiene monoxide are additional alkylene oxides, specified. This subject-matter does not appear in the Specification as accepted.ALSO:Hydroxy ester derivatives of propylene oxide suitable for use as lubricants are obtained by reacting from 10 to 48 molecular proportions of propylene oxide with one molecular proportion of an aliphatic ester of a hydroxy aliphatic carboxylic acid containing from 1 to 3 carboxyl groups and one or more hydroxyl groups. The terminal hydroxyl group of the product may be etherified or esterified. It is preferred to use from 10 to 30 and especially from 14 to 22 molecular proportions of the propylene oxide. The hydrocarbon chain of the hydroxy acids may be saturated or unsaturated and the acids specified are glycollic acid, hydracrylic acid, hydroxybutyric acid, hydroxy caproic acid, lactic acid, malic acid, citric acid, hydroxystearic acid and ricinoleic acid. The esterifying radical may be a saturated or unsaturated hydrocarbon group and may contain hydroxyl groups as in the glyceryl radical. Other specified radicals are ethyl, propyl, butyl, amyl, octyl, decyl, dodecyl, stearyl, oleyl and longchain radicals derived from cracked paraffinic waxes. The preferred hydroxy acid esters are those having 2 to 20 carbon atoms in the acid radical and 1 to 20 carbon atoms in the ester group and the ester should preferably contain 1 to 4 hydroxyl groups per molecule. The reaction may be conducted at temperatures down to - 10 DEG C. and metal halide catalysts such as boron fluoride and stannic chloride are generally required. In examples: (1) ethyl lactate (1 molecular proportion) is treated with propylene oxide (14 molecular proportions) in the presence of anhydrous SnCl4 in chloroform at 30 DEG C.; (2) di-n-butyl malate (1 molecular proportion) is reacted with propylene oxide (14 molecular proportions) in the presence of BF3 at 35-45 DEG C.; (3) triethyl citrate and propylene oxide are reacted as in (2) except that the molecular proportion of propylene oxide to ester is 16 : 1; (4) castor oil (1 molecular proportion) is reacted with 48 molecular proportions of propylene oxide in the presence of BF3 as in (2). The properties of the products as lubricants are given in each case. Specifications 312,523, [Class 2 (iii) and 443,631 are referred to. The Specification as open to inspection under Sect. 91 refers to the use of any alkylene oxide in any molecular proportion and states that a hydroxy aliphatic carboxylic acid as well as the ester thereof may be treated. Ethylene oxide, isopropyl ethylene oxide, isobutylene oxide and butadiene monoxide are additional alkylene oxides specified. This subject-matter does not appear in the Specification as accepted.
GB24925/48A 1947-12-31 1948-09-23 Hydroxy ester derivatives of propylene oxide Expired GB664992A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US664992XA 1947-12-31 1947-12-31

Publications (1)

Publication Number Publication Date
GB664992A true GB664992A (en) 1952-01-16

Family

ID=22069875

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24925/48A Expired GB664992A (en) 1947-12-31 1948-09-23 Hydroxy ester derivatives of propylene oxide

Country Status (1)

Country Link
GB (1) GB664992A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE974767C (en) * 1953-08-11 1961-05-18 Union Carbide Corp Process for the production of polyglycol ethers of higher alcohols
DE1135445B (en) * 1953-07-02 1962-08-30 Exxon Research Engineering Co Process for the preparation of complex esters which can be used as lubricating oils or lubricating oil components
CN105542145A (en) * 2016-02-22 2016-05-04 中国林业科学研究院林产化学工业研究所 Citrate ether polymeric polylol and preparation method and application thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1135445B (en) * 1953-07-02 1962-08-30 Exxon Research Engineering Co Process for the preparation of complex esters which can be used as lubricating oils or lubricating oil components
DE974767C (en) * 1953-08-11 1961-05-18 Union Carbide Corp Process for the production of polyglycol ethers of higher alcohols
CN105542145A (en) * 2016-02-22 2016-05-04 中国林业科学研究院林产化学工业研究所 Citrate ether polymeric polylol and preparation method and application thereof

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