FR2243174A1 - 5-Alkenyl and 5-alkylidene-norbornene-2 cpds - novel multi-stage process from cyclopentadiene or dicyclopentadiene - Google Patents

5-Alkenyl and 5-alkylidene-norbornene-2 cpds - novel multi-stage process from cyclopentadiene or dicyclopentadiene

Info

Publication number
FR2243174A1
FR2243174A1 FR7332633A FR7332633A FR2243174A1 FR 2243174 A1 FR2243174 A1 FR 2243174A1 FR 7332633 A FR7332633 A FR 7332633A FR 7332633 A FR7332633 A FR 7332633A FR 2243174 A1 FR2243174 A1 FR 2243174A1
Authority
FR
France
Prior art keywords
pref
alkylidene
alkenyl
cpds
sulphoester
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
FR7332633A
Other languages
French (fr)
Other versions
FR2243174B1 (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.)
Compagnie Francaise de Raffinage SA
Original Assignee
Compagnie Francaise de Raffinage 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 Compagnie Francaise de Raffinage SA filed Critical Compagnie Francaise de Raffinage SA
Priority to FR7332633A priority Critical patent/FR2243174A1/en
Publication of FR2243174A1 publication Critical patent/FR2243174A1/en
Application granted granted Critical
Publication of FR2243174B1 publication Critical patent/FR2243174B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/39—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms
    • C07C13/42—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms with a bicycloheptene ring structure
    • C07C13/43—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms with a bicycloheptene ring structure substituted by unsaturated acyclic hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
    • C07C1/322—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom the hetero-atom being a sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Landscapes

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

Abstract

Prepg. 5-alkylidene and/or 5-alkenyl-norbornene-2-cpds. of formula (I) or (II) (where R1,R2 and R3 are H or alkyl) are prod. by (a) forming the 5-hydroxyalkyl cpd. (III) above from cyclopentadiene and/or dicyclopentadiene, pref. by reacting with a dialkyl alkenyl carbinal ester at 100-190 degrees C followed by alkaline hydrolysis of the prod. at 130-170 degrees C (b) reacting (III) with a cpd. R4SO2Cl(where R4 is aliphatic or aromatic) in the presence of an organic base pref. pyridine, picolines, lutidines, trimethylamino or dimethylaniline, to form the sulphoester (c) eliminating the sulphoester gp. using an org. base, pref. pyridine, picolines, lutidines, dimethylamine or triethylamine, in a polar solvent, pref. dimethylformaide, dimethylacetamide, hexametapel or alcohols, at at 50-150 degrees C. Alternatively the alcohol plus alcoholate may be used as solvent/base and also the sulphoester may pref. not be isolated (d) sepg. (I) and nII) formed pref. by distillation (e) isomerising the 5-alkenyl cpd (II) to the alkylidene (I). The 5-alkylidene cpds. are used as diene monomers in EPDM terpolymers (ethylene/propylene/diene monomers). The process gives higher yields, partic. in step (a) and also avoids costly inters.
FR7332633A 1973-09-11 1973-09-11 5-Alkenyl and 5-alkylidene-norbornene-2 cpds - novel multi-stage process from cyclopentadiene or dicyclopentadiene Granted FR2243174A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7332633A FR2243174A1 (en) 1973-09-11 1973-09-11 5-Alkenyl and 5-alkylidene-norbornene-2 cpds - novel multi-stage process from cyclopentadiene or dicyclopentadiene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7332633A FR2243174A1 (en) 1973-09-11 1973-09-11 5-Alkenyl and 5-alkylidene-norbornene-2 cpds - novel multi-stage process from cyclopentadiene or dicyclopentadiene

Publications (2)

Publication Number Publication Date
FR2243174A1 true FR2243174A1 (en) 1975-04-04
FR2243174B1 FR2243174B1 (en) 1977-05-13

Family

ID=9124856

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7332633A Granted FR2243174A1 (en) 1973-09-11 1973-09-11 5-Alkenyl and 5-alkylidene-norbornene-2 cpds - novel multi-stage process from cyclopentadiene or dicyclopentadiene

Country Status (1)

Country Link
FR (1) FR2243174A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0189581A1 (en) * 1985-01-03 1986-08-06 BASF Aktiengesellschaft 2,3-Disubstituted bicyclo[2,2,1]heptanes and heptenes, their preparation and their use as perfumes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0189581A1 (en) * 1985-01-03 1986-08-06 BASF Aktiengesellschaft 2,3-Disubstituted bicyclo[2,2,1]heptanes and heptenes, their preparation and their use as perfumes
US4728747A (en) * 1985-01-03 1988-03-01 Basf Aktiengesellschaft Novel 2,3-disubstituted bicyclo(2.2.1)heptanes and heptenes, their preparation, and their use as scents

Also Published As

Publication number Publication date
FR2243174B1 (en) 1977-05-13

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Legal Events

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