FR2389588A1 - Metathesis conversion of olefin to unsatd. ester and di:ester - by reacting a cyclic olefin and an acyclic olefin having a functional gp. in presence of tungsten halide catalyst - Google Patents

Metathesis conversion of olefin to unsatd. ester and di:ester - by reacting a cyclic olefin and an acyclic olefin having a functional gp. in presence of tungsten halide catalyst

Info

Publication number
FR2389588A1
FR2389588A1 FR7713804A FR7713804A FR2389588A1 FR 2389588 A1 FR2389588 A1 FR 2389588A1 FR 7713804 A FR7713804 A FR 7713804A FR 7713804 A FR7713804 A FR 7713804A FR 2389588 A1 FR2389588 A1 FR 2389588A1
Authority
FR
France
Prior art keywords
olefin
ester
unsatd
diesters
esters
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.)
Granted
Application number
FR7713804A
Other languages
French (fr)
Other versions
FR2389588B1 (en
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.)
Rhone Poulenc Industries SA
Original Assignee
Rhone Poulenc Industries SA
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 Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA
Priority to FR7713804A priority Critical patent/FR2389588A1/en
Priority to US05/902,709 priority patent/US4233230A/en
Priority to JP5289078A priority patent/JPS5416412A/en
Priority to BE187425A priority patent/BE866741A/en
Priority to NL7804882A priority patent/NL7804882A/en
Priority to GB18054/78A priority patent/GB1586747A/en
Priority to IT49209/78A priority patent/IT1104196B/en
Priority to DE2819598A priority patent/DE2819598C3/en
Publication of FR2389588A1 publication Critical patent/FR2389588A1/en
Application granted granted Critical
Publication of FR2389588B1 publication Critical patent/FR2389588B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A cyclic alefine of formula (I). (where R1 and R4, each are H, CH3 or C2H5; R2 and R3 each are H or a =5C alkyl gp; and n1 is a 2-12 integer) is reacted with an acyclic olefic of formula (II) (where R5 is as R1 or R4, or is -(CR2R3)n3 Y(where Y is OOCR10, OCOR11, or halogen; and n3 is a >=1 integer except when Y is OOCR10, when it is >=2; R10 and R11 are opt branced chain alkyl or aryl); R6 and R7 are as R1 or R4; R8 and R9 are as R2 and R3; X is a Y; and n2 is a >=1 integer except when X is OOC CH3 when n2 is >=2). The reaction between (I) and (II) is carried out in the presence of a pair of catalysts comprising a tungsten halide and an organotin reducing agent. Metathesis can yield unsatd. linear esters or diesters which are starting materials leading via the satd. esters or diesters to alcohols which are totally biodegradable, excellent detergents. The process gives simply, and on an industrial scale, selectively, unsatd. esters or diesters of a well defined C chain length between 12 and 18C so that the required stable mechanical and thermal properties are obtd.
FR7713804A 1977-05-06 1977-05-06 Metathesis conversion of olefin to unsatd. ester and di:ester - by reacting a cyclic olefin and an acyclic olefin having a functional gp. in presence of tungsten halide catalyst Granted FR2389588A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
FR7713804A FR2389588A1 (en) 1977-05-06 1977-05-06 Metathesis conversion of olefin to unsatd. ester and di:ester - by reacting a cyclic olefin and an acyclic olefin having a functional gp. in presence of tungsten halide catalyst
JP5289078A JPS5416412A (en) 1977-05-06 1978-05-04 Double decomposition method of cyclic olefin and nonncyclic olefin having functional group
US05/902,709 US4233230A (en) 1977-05-06 1978-05-04 Process for preparing olefins by metathesis of cyclic olefins with acyclic olefins
NL7804882A NL7804882A (en) 1977-05-06 1978-05-05 METHOD OF PERFORMING A METHATHESIS REACTION BETWEEN A CYCLICAL ALKES AND A FUNCTIONAL GROUP CONTAINING ACYCLICAL ALKES.
BE187425A BE866741A (en) 1977-05-06 1978-05-05 PROCESS FOR THE METATHESIS OF A CYCLIC OLEFIN AND OF AN ACYCLIC OLEFIN CARRIING A FUNCTIONAL GROUP
GB18054/78A GB1586747A (en) 1977-05-06 1978-05-05 Process for the metathesis of a cyclic olefin and an acrylic olefin carrying a functional group
IT49209/78A IT1104196B (en) 1977-05-06 1978-05-05 METHODESIS PROCEDURE OF A CYCLIC OLEPHINE AND AN ACYCLIC OLEFINE CARRIER OF A FUNCTIONAL GROUP
DE2819598A DE2819598C3 (en) 1977-05-06 1978-05-05 Process for the metathesis of olefins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7713804A FR2389588A1 (en) 1977-05-06 1977-05-06 Metathesis conversion of olefin to unsatd. ester and di:ester - by reacting a cyclic olefin and an acyclic olefin having a functional gp. in presence of tungsten halide catalyst

Publications (2)

Publication Number Publication Date
FR2389588A1 true FR2389588A1 (en) 1978-12-01
FR2389588B1 FR2389588B1 (en) 1979-10-12

Family

ID=9190433

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7713804A Granted FR2389588A1 (en) 1977-05-06 1977-05-06 Metathesis conversion of olefin to unsatd. ester and di:ester - by reacting a cyclic olefin and an acyclic olefin having a functional gp. in presence of tungsten halide catalyst

Country Status (2)

Country Link
BE (1) BE866741A (en)
FR (1) FR2389588A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0084437A1 (en) * 1982-01-13 1983-07-27 BP Chemicals Limited Dismutation of functionalised olefins
EP0099572A1 (en) * 1982-07-20 1984-02-01 Phillips Petroleum Company Disproportionation of functional olefins

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NEANT *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0084437A1 (en) * 1982-01-13 1983-07-27 BP Chemicals Limited Dismutation of functionalised olefins
EP0099572A1 (en) * 1982-07-20 1984-02-01 Phillips Petroleum Company Disproportionation of functional olefins

Also Published As

Publication number Publication date
FR2389588B1 (en) 1979-10-12
BE866741A (en) 1978-11-06

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Legal Events

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