FR2362102A1 - 1,1-Dihalo 4-methyl pentadiene prepn. - from isobutene and 1,1,2-trihalo ethylene - Google Patents

1,1-Dihalo 4-methyl pentadiene prepn. - from isobutene and 1,1,2-trihalo ethylene

Info

Publication number
FR2362102A1
FR2362102A1 FR7620117A FR7620117A FR2362102A1 FR 2362102 A1 FR2362102 A1 FR 2362102A1 FR 7620117 A FR7620117 A FR 7620117A FR 7620117 A FR7620117 A FR 7620117A FR 2362102 A1 FR2362102 A1 FR 2362102A1
Authority
FR
France
Prior art keywords
prepn
isobutene
pref
dihalo
trihaloethylene
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.)
Withdrawn
Application number
FR7620117A
Other languages
French (fr)
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 claimed from GB27923/75A external-priority patent/GB1531733A/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of FR2362102A1 publication Critical patent/FR2362102A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/266—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of hydrocarbons and halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/19—Halogenated dienes

Landscapes

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

Abstract

The prepn. of 1,1-dihalo-4-methylpentadienes is carried out by vapour-phase reaction of isobutene with a 1,1,2-trihaloethylene at elevated temp. The major product when halo = Cl, viz. 1,1-dichloro-4-methyl-1,4-pentadiene (I), can be isomerised to 1,1-dichloro-4-methyl-1,3-pentadiene (II) by heating in the presence of p-toluenesulphonic acid. (II) is an intermediate for the prepn. of insecticidal 2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropane-1-carboxylate esters. The trihaloethylene is pref. 1,1,2-trichloroethylene (III). The reaction temp. is pref. 250-600 degrees C (esp. 475-525degrees C). The contact time is pref. 20 (esp. 5-15) sec. The trihaloethylene/isobutene molar ratio is pref. >1 (esp. 3-10). A radical initiator (e.g. t-butyl hydroperoxide or H2O2) can opt. be used.
FR7620117A 1975-07-02 1976-07-01 1,1-Dihalo 4-methyl pentadiene prepn. - from isobutene and 1,1,2-trihalo ethylene Withdrawn FR2362102A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB27923/75A GB1531733A (en) 1975-07-02 1975-07-02 Production of 1,1-dihalo-4-methylpenta-1,3-or 1,4-dienes
GB1224776 1976-03-26

Publications (1)

Publication Number Publication Date
FR2362102A1 true FR2362102A1 (en) 1978-03-17

Family

ID=26248888

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7620117A Withdrawn FR2362102A1 (en) 1975-07-02 1976-07-01 1,1-Dihalo 4-methyl pentadiene prepn. - from isobutene and 1,1,2-trihalo ethylene

Country Status (9)

Country Link
JP (1) JPS527907A (en)
CA (1) CA1072126A (en)
DE (1) DE2629868A1 (en)
DK (1) DK297576A (en)
FR (1) FR2362102A1 (en)
IE (1) IE43137B1 (en)
IT (1) IT1064095B (en)
LU (1) LU75277A1 (en)
NL (1) NL7607264A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2349961B1 (en) * 2008-10-13 2016-11-23 Blue Cube IP LLC Process for the production of chlorinated and/or fluorinated propenes

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1017159B (en) * 1952-06-18 1957-10-10 Dow Chemical Co Process for the preparation of 3-aryl-1, 1-dichloro-2-methylpropenen-1
FR1297752A (en) * 1960-03-23 1962-07-06 Stauffer Chemical Co Process for manufacturing chlorinated unsaturated hydrocarbons, products obtained and their applications
FR2309499A1 (en) * 1975-04-28 1976-11-26 Ici Ltd PROCESS FOR PREPARING 1,1-DICHLORO-4-METHYLPENTA-1,3-DIENE AND PRODUCT OBTAINED

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1017159B (en) * 1952-06-18 1957-10-10 Dow Chemical Co Process for the preparation of 3-aryl-1, 1-dichloro-2-methylpropenen-1
FR1297752A (en) * 1960-03-23 1962-07-06 Stauffer Chemical Co Process for manufacturing chlorinated unsaturated hydrocarbons, products obtained and their applications
FR2309499A1 (en) * 1975-04-28 1976-11-26 Ici Ltd PROCESS FOR PREPARING 1,1-DICHLORO-4-METHYLPENTA-1,3-DIENE AND PRODUCT OBTAINED

Also Published As

Publication number Publication date
CA1072126A (en) 1980-02-19
IE43137B1 (en) 1980-12-31
AU1523576A (en) 1978-01-05
NL7607264A (en) 1977-01-04
DE2629868A1 (en) 1977-01-20
DK297576A (en) 1977-01-03
LU75277A1 (en) 1977-07-22
JPS527907A (en) 1977-01-21
IT1064095B (en) 1985-02-18
IE43137L (en) 1977-01-02

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