GB614931A - Improvements in or relating to the production of new diels-alder adducts - Google Patents

Improvements in or relating to the production of new diels-alder adducts

Info

Publication number
GB614931A
GB614931A GB5784/46A GB578446A GB614931A GB 614931 A GB614931 A GB 614931A GB 5784/46 A GB5784/46 A GB 5784/46A GB 578446 A GB578446 A GB 578446A GB 614931 A GB614931 A GB 614931A
Authority
GB
United Kingdom
Prior art keywords
molar ratio
cyclopentadiene
hexachlorocyclopentadiene
heated
diels
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
GB5784/46A
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.)
Velsicol Corp
Original Assignee
Velsicol Corp
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 Velsicol Corp filed Critical Velsicol Corp
Publication of GB614931A publication Critical patent/GB614931A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
    • C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds

Abstract

The Diels-Alder synthesis is effected with a hexahalocyclopentadiene, and an unsaturated compound such as cyclopentadiene, dicyclopentadiene, butadiene, styrene, indene, p phenylacetylene, fulvene or maleic anhydride, to give products which may be used as intermediates in the preparation of alkyd resins.ALSO:The Diels-Alder synthesis is effected with a hexahalocyclopentadiene as the diene and an unsaturated compound such as cyclopentadiene, dicyclopentadiene, butadiene, styrene, indene, phenylacetylene, fulvene or maleic anhydride, as the dienophile, to give products which may be used variously as intermediates in the preparation of alkyd resins, as plasticizers or as insecticides. In examples: (1) hexachlorocyclopentadiene is reacted with cyclopentadiene in molar ratio 1 : 1; (2) hexabromocyclopentadiene is reacted with cyclopentadiene in hexane in molar ratio 1 : 1; (3) monochloropentabromocyclopentadiene is reacted with cyclopentadiene in molar ratio 1 : 1; (4) hexachlorocyclopentadiene is heated with styrene in molar ratio 1 : 1; (5) and (6) hexachlorocyclopentadiene is heated with dicyclopentadiene in molar ratio 1 : 1 and 2 : 1; (7) hexachlorocyclopentadiene is heated with indene in molar ratio 1 : 1; (8) hexachlorocyclopentadiene is heated with isoprene in molar ratio 1 : 1; (9) and (10) hexachlorocyclopentadiene is heated with butadiene in molar ratio 1 : 1 and 2 : 1; (11) hexachlorocyclopentadiene is heated with phenyl acetylene in molar ratio 1 : 1; and (12) hexachlorocyclopentadiene is heated with maleic anhydride in molar ratio 1 : 1.ALSO:The Diels-Alder adducts obtained by condensing a hexahalocyclopentadiene with an unsaturated compound in the Diels-Alder synthesis have insecticidal properties and examples are given of insecticides obtained by dissolving an organic thiocyanate and one of the following in a hydrocarbon base oil-the adduct of hexachloro - cyclopentadiene and cyclopentadiene (or styrene, butadiene or isoprene), the adduct of hexabromocyclopentadiene and cyclopentadiene, and the adduct of monochloropentabromocyclopentadiene and cyclopentadiene. The adducts may also be utilised in the form of oil sprays, dusts, aqueous emulsions and aerosols.
GB5784/46A 1945-03-05 1946-02-25 Improvements in or relating to the production of new diels-alder adducts Expired GB614931A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US614931XA 1945-03-05 1945-03-05

Publications (1)

Publication Number Publication Date
GB614931A true GB614931A (en) 1948-12-30

Family

ID=22036142

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5784/46A Expired GB614931A (en) 1945-03-05 1946-02-25 Improvements in or relating to the production of new diels-alder adducts

Country Status (3)

Country Link
BE (1) BE614931A (en)
GB (1) GB614931A (en)
MY (1) MY5300131A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2616899A (en) * 1951-03-26 1952-11-04 Us Rubber Co Chlorinated epoxy compounds
US2676132A (en) * 1950-04-18 1954-04-20 Shell Dev 1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4alpha,5,6,7,8,8alpha-octhydro-1,4,5,8-dimethanonaphthalene and insecticidal compositions thereof
DE951866C (en) * 1952-08-14 1956-11-08 Velsicol Chemical Corp Process for the preparation of insecticidally active 1-fluoro-4,5,6,7,8,8-hexachlor-3a, 4ú¼7ú¼7a-tetrahydro-4, 7-endomethylene indene
US2771479A (en) * 1949-10-17 1956-11-20 Universal Oil Prod Co Insecticidal compounds
US2779769A (en) * 1952-09-10 1957-01-29 Hooker Electrochemical Co Poly-halogen-containing dicarboxylic acids and anhydrides
DE960989C (en) * 1954-04-18 1957-03-28 Hoechst Ag Process for the preparation of halogenated bicyclo- [2, 2, 1] -hepten- (2) - and bicyclo- [2, 2, 1] -heptadiene- (2, 5) -bis-oxyalkylene- (5, 6) - links
DE1006418B (en) * 1952-12-23 1957-04-18 Hoechst Ag Process for the preparation of penta and hexachloro derivatives of 5-oxybicyclo- [2, 2, 1] -heptens- (2)
DE1035651B (en) * 1953-01-29 1958-08-07 Bataafsche Petroleum Process for the production of polycyclic pest control agents with two linearly linked bicyclo- (2, 2, 1) -heptane rings
US2898835A (en) * 1956-10-08 1959-08-11 Nig Mfg Company Ltd Apparatus for the continuous development of light sensitive papers
US2912356A (en) * 1954-03-29 1959-11-10 Universal Oil Prod Co Bicyclic organic compounds containing a large proportion per unit mass of halogen
DE1269115B (en) * 1953-06-17 1968-05-30 Hoechst Ag Process for the preparation of 2, 3, 4-trichlorobenzotrichloride

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2771479A (en) * 1949-10-17 1956-11-20 Universal Oil Prod Co Insecticidal compounds
US2676132A (en) * 1950-04-18 1954-04-20 Shell Dev 1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4alpha,5,6,7,8,8alpha-octhydro-1,4,5,8-dimethanonaphthalene and insecticidal compositions thereof
US2616899A (en) * 1951-03-26 1952-11-04 Us Rubber Co Chlorinated epoxy compounds
DE951866C (en) * 1952-08-14 1956-11-08 Velsicol Chemical Corp Process for the preparation of insecticidally active 1-fluoro-4,5,6,7,8,8-hexachlor-3a, 4ú¼7ú¼7a-tetrahydro-4, 7-endomethylene indene
US2779769A (en) * 1952-09-10 1957-01-29 Hooker Electrochemical Co Poly-halogen-containing dicarboxylic acids and anhydrides
DE1006418B (en) * 1952-12-23 1957-04-18 Hoechst Ag Process for the preparation of penta and hexachloro derivatives of 5-oxybicyclo- [2, 2, 1] -heptens- (2)
DE1035651B (en) * 1953-01-29 1958-08-07 Bataafsche Petroleum Process for the production of polycyclic pest control agents with two linearly linked bicyclo- (2, 2, 1) -heptane rings
DE1269115B (en) * 1953-06-17 1968-05-30 Hoechst Ag Process for the preparation of 2, 3, 4-trichlorobenzotrichloride
US2912356A (en) * 1954-03-29 1959-11-10 Universal Oil Prod Co Bicyclic organic compounds containing a large proportion per unit mass of halogen
DE960989C (en) * 1954-04-18 1957-03-28 Hoechst Ag Process for the preparation of halogenated bicyclo- [2, 2, 1] -hepten- (2) - and bicyclo- [2, 2, 1] -heptadiene- (2, 5) -bis-oxyalkylene- (5, 6) - links
US2898835A (en) * 1956-10-08 1959-08-11 Nig Mfg Company Ltd Apparatus for the continuous development of light sensitive papers

Also Published As

Publication number Publication date
BE614931A (en) 1962-09-10
MY5300131A (en) 1953-12-31

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