GB1117308A - Improvements in the manufacture of self-condensed ªÏ-hydroxyacids - Google Patents

Improvements in the manufacture of self-condensed ªÏ-hydroxyacids

Info

Publication number
GB1117308A
GB1117308A GB37451/64A GB3745164A GB1117308A GB 1117308 A GB1117308 A GB 1117308A GB 37451/64 A GB37451/64 A GB 37451/64A GB 3745164 A GB3745164 A GB 3745164A GB 1117308 A GB1117308 A GB 1117308A
Authority
GB
United Kingdom
Prior art keywords
ions
ketone
per
sulphate
bisulphate
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
GB37451/64A
Inventor
Gordon Ernest Smith
Colin James Mcnae
Ernest Jan Kowolik
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.)
Acordis UK Ltd
Original Assignee
British Celanese Ltd
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
Priority to NL129848D priority Critical patent/NL129848C/xx
Application filed by British Celanese Ltd filed Critical British Celanese Ltd
Priority to GB37451/64A priority patent/GB1117308A/en
Priority to BE669607A priority patent/BE669607A/xx
Priority to FR31305A priority patent/FR1446847A/en
Priority to NL6511967A priority patent/NL6511967A/xx
Priority to DE19651518597 priority patent/DE1518597A1/en
Publication of GB1117308A publication Critical patent/GB1117308A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/23—Oxidation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A process for making polyesters comprises oxidizing an alicyclic ketone having at most 8 carbon atoms in the ring to a self-condensed o -hydroxy acid, the oxidizing agent being formed by electrolysing an aqueous solution containing bisulphate ions to convert at least some of the ions to perdisulphate ions and allowing the perdisulphate ions to hydrolyse forming permonosulphate ions. The alicyclic ketone is added to the oxidizing solution to form the self-condensed o -hydroxy acid with reduction of permonosulphate to bisulphate, the acid is separated and the remaining bisulphate solution is recycled to the electrolysis cell.ALSO:Self-condensed o -hydroxy acids consisting of lactones, and linear poly-esters are made by oxidizing an alicyclic ketone having at most 8C atoms using an aqueous solution containing permono-sulphate ions which oxidize the ketone, and become reduced to bisulphate ions. The solution of bisulphate ions is recycled to an electrolytic cell where per-disulphate ions are formed which is then allowed to hydrolyze to per-mono-sulphate ions and the ketone is then added. A solution containing ammonium sulphate and sulphuric acid with a trace of ammonium thiocyanate, is electrolyzed forming ammonium per-disulphate [(NH4)2S2O8]; this hydrolyzes spontaneousl to per-mono-sulphate containing 2.31 mols of active oxygen of which 2.07 mols. are per-mono-sulphate. The ketone e.g. cyclohexanone is added gradually before further hydrolysis occurs yielding bisulphate and H2O2. The reaction temperature is maintained at 50 DEG C. The product separates into two layers. The aqueous layer is extracted with a solvent e.g. a ketone or alcohol, and the extracted material added to the upper layer. The total product is 0.53 mol. of 6-hydroxy caproic acid and its self-condensed derivative with minor amounts of cyclohexanone and adipic acid. The aqueous electrolyte is fixed from residual organic matters by filtration through an absorbent e.g. activated charcoal, and recycled to the electrolytic cell to regenerate per-disulphate. In another example, cycloheptanone is oxidized to form poly-oenanthate ester. The lactone may be convected to capiolactain by heating under pressure with ammonia. The formation and consumption of per-mono-sulphate during addition of the ketone should be monitored e.g. by measuring the oxidation potential of the electrolyte, so that the rate of addition of the ketone does not exceed the rate of formation of per-mono-sulphate ions formed by hydrolysis.
GB37451/64A 1964-09-14 1964-09-14 Improvements in the manufacture of self-condensed ªÏ-hydroxyacids Expired GB1117308A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL129848D NL129848C (en) 1964-09-14
GB37451/64A GB1117308A (en) 1964-09-14 1964-09-14 Improvements in the manufacture of self-condensed ªÏ-hydroxyacids
BE669607A BE669607A (en) 1964-09-14 1965-09-14
FR31305A FR1446847A (en) 1964-09-14 1965-09-14 Improvements in the production of hydroxy acids
NL6511967A NL6511967A (en) 1964-09-14 1965-09-14
DE19651518597 DE1518597A1 (en) 1964-09-14 1965-09-14 Process for the preparation of self-condensed omega-hydroxy acids

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB37451/64A GB1117308A (en) 1964-09-14 1964-09-14 Improvements in the manufacture of self-condensed ªÏ-hydroxyacids
GB4788164 1964-11-25
GB830765 1965-02-26

Publications (1)

Publication Number Publication Date
GB1117308A true GB1117308A (en) 1968-06-19

Family

ID=27255186

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37451/64A Expired GB1117308A (en) 1964-09-14 1964-09-14 Improvements in the manufacture of self-condensed ªÏ-hydroxyacids

Country Status (4)

Country Link
BE (1) BE669607A (en)
DE (1) DE1518597A1 (en)
GB (1) GB1117308A (en)
NL (2) NL6511967A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4874485A (en) * 1987-06-29 1989-10-17 United Kingdom Atomic Energy Authority Method for the treatment of waste matter

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4874485A (en) * 1987-06-29 1989-10-17 United Kingdom Atomic Energy Authority Method for the treatment of waste matter

Also Published As

Publication number Publication date
NL6511967A (en) 1966-03-15
DE1518597A1 (en) 1969-04-03
NL129848C (en)
BE669607A (en) 1965-12-31

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