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GB894639A - Improvements relating to the preparation of esters - Google Patents

Improvements relating to the preparation of esters

Info

Publication number
GB894639A
GB894639A GB1671259A GB1671259A GB894639A GB 894639 A GB894639 A GB 894639A GB 1671259 A GB1671259 A GB 1671259A GB 1671259 A GB1671259 A GB 1671259A GB 894639 A GB894639 A GB 894639A
Authority
GB
United Kingdom
Prior art keywords
acid
refluxing
diol
mixture
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
GB1671259A
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.)
HILDA MARY BIRCH
BP PLC
Original Assignee
HILDA MARY BIRCH
BP PLC
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 HILDA MARY BIRCH, BP PLC filed Critical HILDA MARY BIRCH
Priority to GB1671259A priority Critical patent/GB894639A/en
Publication of GB894639A publication Critical patent/GB894639A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Complex esters are prepared by esterifying in one or more stages (a) either (i) a monohydric alcohol or mixture of such alcohols or (ii) an aliphatic monocarboxylic acid or mixture of such acids, (b) an aliphatic dicarboxylic acid or mixture of such acids, and (c) a diol or mixture of such diols, in the presence of an alkali metal pyrosulphate as esterification catalyst. Esterification may be effected by: (i) refluxing all the reactants together; (ii) refluxing the diol and dicarboxylic acid together, the product being subsequently refluxed with alcohol or monocarboxylic acid; (iii) refluxing the alcohol and dicarboxylic acid together, the product being subsequently refluxed with diol; (iv) refluxing the monocarboxylic acid and diol together, the product being subsequently refluxed with dicarboxylic acid. In examples: (1) adipic acid, sebacic acid, neopentyl glycol and iso-octanol are reacted as in method (ii) above in the presence of benzene and (a) no catalyst, (b) sodium bisulphate, or (c) potassium pyrosulphate; (2) 3:5:5-trimethyl-hexanol, sebacic acid, adipic acid and neopentyl glycol are reacted as in method (i) above in the presence of benzene and (a) no catalyst, (b) sodium bisulphate, or (c) potassium pyrosulphate. Other reactants specified are: C8-C18 alcohols, e.g. 2-ethylhexanol, 2:2:4-trimethylpentanol and iso-tridecanol (as prepared by the oxo process); C8-C10 acids, e.g. pelargonic and 2-ethylhexanoic acid; azelaic acid; ethylene glycol, propylene glycol and polyethylene glycol 200. Specification 687,348 is referred to.ALSO:Complex esters are prepared by esterifying in one or more stages (a) either (i) a monohydric alcohol or mixture of such alcohols or (ii) an aliphatic monocarboxylic acid or mixture of such acids, (b) an aliphatic dicarboxylic acid or mixture of such acids, and (c) a diol or mixture of diols, in the presence of an alkali metal pyrosulphate as esterification catalyst. Esterification may be effected by (i) refluxing all the reactants together; (ii) refluxing the diol and dicarboxylic acid together, the product being subsequently refluxed with alcohol or monocarboxylic acid; (iii) refluxing the alcohol and dicarboxylic acid together, the product being subsequently refluxed with diol; or (iv) refluxing the monocarboxylic acid and diol together, the product being subsequently refluxed with dicarboxylic acid. In examples (i) adipic acid, sebacic acid, neopentyl glycol and iso-octanol are reacted as in method (ii) above in the presence of benzene and (a) no catalyst, (b) sodium bisulphate, or (c) potassium pyrosulphate; (2) 3 : 5 : 5-trimethylhexanol, sebacic acid, adipic acid and neopentyl glycol are reacted as in method (i) above in the presence of benzene and (a) no catalyst, (b) sodium bisulphate, or (c) potassium pyrosulphate. Other reactants specified are C8-C18 alcohols, e.g. 2-ethylhexanol, 2 : 2 : 4-trimethylpentanol, and iso-tridecanol (as produced by the oxo process); C8-C10 acids, e.g. pelargonic acid and 2-ethylhexanoic acid; azelaic acid; ethylene glycol, propylene glycol and polyethylene glycol 200. Specification 687,348 is referred to.
GB1671259A 1959-05-15 1959-05-15 Improvements relating to the preparation of esters Expired GB894639A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1671259A GB894639A (en) 1959-05-15 1959-05-15 Improvements relating to the preparation of esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1671259A GB894639A (en) 1959-05-15 1959-05-15 Improvements relating to the preparation of esters

Publications (1)

Publication Number Publication Date
GB894639A true GB894639A (en) 1962-04-26

Family

ID=10082305

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1671259A Expired GB894639A (en) 1959-05-15 1959-05-15 Improvements relating to the preparation of esters

Country Status (1)

Country Link
GB (1) GB894639A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5820777A (en) 1993-03-10 1998-10-13 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US5833876A (en) 1992-06-03 1998-11-10 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5851968A (en) 1994-05-23 1998-12-22 Henkel Corporation Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants
US5853609A (en) 1993-03-10 1998-12-29 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
US5906769A (en) 1992-06-03 1999-05-25 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5976399A (en) 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US6183662B1 (en) 1992-06-03 2001-02-06 Henkel Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5833876A (en) 1992-06-03 1998-11-10 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5906769A (en) 1992-06-03 1999-05-25 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5976399A (en) 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US6183662B1 (en) 1992-06-03 2001-02-06 Henkel Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US6221272B1 (en) 1992-06-03 2001-04-24 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
US6296782B1 (en) 1992-06-03 2001-10-02 Henkel Corporation Polyol ester lubricants for refrigerator compressors operating at high temperatures
US6551524B2 (en) 1992-06-03 2003-04-22 Cognis Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US6666985B2 (en) 1992-06-03 2003-12-23 Cognis Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
US5820777A (en) 1993-03-10 1998-10-13 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US5853609A (en) 1993-03-10 1998-12-29 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
US5851968A (en) 1994-05-23 1998-12-22 Henkel Corporation Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants
US6551523B1 (en) 1995-06-07 2003-04-22 Cognis Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids

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