GB661806A - Improvements in or relating to the production of dichlorobutenes - Google Patents

Improvements in or relating to the production of dichlorobutenes

Info

Publication number
GB661806A
GB661806A GB1374149A GB1374149A GB661806A GB 661806 A GB661806 A GB 661806A GB 1374149 A GB1374149 A GB 1374149A GB 1374149 A GB1374149 A GB 1374149A GB 661806 A GB661806 A GB 661806A
Authority
GB
Grant status
Application
Patent type
Prior art keywords
initial
deg
final
chlorine
butadiene
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
GB1374149A
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.)
E I du Pont de Nemours and Co
Original Assignee
E I du Pont de Nemours and Co
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

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/013Preparation of halogenated hydrocarbons by addition of halogens
    • C07C17/02Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons

Abstract

Dichlorobutenes are made by the vapour phase reaction between preheated butadiene and preheated chlorine, the chlorine and at least one mol. of butadiene per mol. of chlorine are introduced into an unpacked initial reaction zone wherein the reactants are thoroughly and rapidly mixed during a relatively short contact time, the temperature in said zone being controlled at a level somewhat above that required to insure a completely vaporous reaction system and the resultant gaseous mixture is subjected in a final reaction zone and during a relatively longer contact time, to a temperature appreciably higher than that of the initial reaction zone but below that at which substantial substitution chlorination of the butadiene takes place. The latter temperature is defined as that temperature at which more than about 5 per cent of the reaction takes place via substitution. 1,4-Dichlorobutene-2 and 3,4-dichlorobutene-1 are the primary products. At pressures of 0.5-2.0 atmos. the mol. ratio of butadiene to chlorine may be 1 : 1 to 16 : 1, temperatures 140-220 DEG C. in the initial and 200-450 DEG C. in the final zones, space velocities of 1500-100,000 and 30-300 vols. of gas at N.T.P. per vol. of initial and final reaction zones per hour respectively and a volume ratio of initial to final reactor of 1 : 10 to 1 : 1000. Preferably the mol. ratio of butadiene to chlorine is 3 : 1 to 6 : 1, initial and final temperature ranges of 160-190 DEG C. and 250-350 DEG C. respectively, and of initial to final reactor volume of 1 : 50 to 1 : 300. The mixing of the preheated reactants must not result in a temperature higher than that to be used in the initial zone. Inert diluents may be used to absorb heat. Products may be isolated by fractional distillation, approximately equal amounts of the two specified compounds being obtained. Unreacted butadiene may be recycled after removal of hydrochloric acid. Elongated or tubular reactors are preferred and the connections between vessels should be conical or graduated to avoid dead spaces. Water should be absent. Chlorination catalysts and packing or contact materials may be used in the final zone. Downflow operation is preferred. Chlorine may be injected at several points in the system including the final reactor. In examples: (1) butadiene at 140 DEG C. and chlorine at 124 DEG C. are thoroughly mixed by means of a tee mixer and reacted at 175 DEG C. in the initial and 250 DEG C. in the final zones to yield dichlorobutadienes, and examples (2)-(8) illustrate the effect of varying the temperatures and space velocities in the reaction of (1).
GB1374149A 1948-05-27 1949-05-23 Improvements in or relating to the production of dichlorobutenes Expired GB661806A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US661806X true 1948-05-27 1948-05-27

Publications (1)

Publication Number Publication Date
GB661806A true true GB661806A (en) 1951-11-28

Family

ID=22067776

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1374149A Expired GB661806A (en) 1948-05-27 1949-05-23 Improvements in or relating to the production of dichlorobutenes

Country Status (1)

Country Link
GB (1) GB661806A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2912471A (en) * 1956-03-21 1959-11-10 Distillers Co Yeast Ltd Chlorination of butadiene
US2928884A (en) * 1956-03-22 1960-03-15 Distillers Co Yeast Ltd Chlorination of butadiene
DE1078109B (en) * 1956-05-15 1960-03-24 Distillers Co Yeast Ltd A process for the preparation of dichlorobutenes
DE1090654B (en) * 1956-03-22 1960-10-13 Distillers Co Yeast Ltd A process for the preparation of dichlorobutenes
DE1090652B (en) * 1956-03-21 1960-10-13 Distillers Co Yeast Ltd A process for the preparation of dichlorobutenes
DE1090655B (en) * 1956-05-15 1960-10-13 Distillers Co Yeast Ltd A process for the preparation of dichlorobutenes
US3058966A (en) * 1959-06-29 1962-10-16 Exxon Research Engineering Co Polymers of halogenated alicyclic and straight chain monomers
US3708548A (en) * 1968-12-10 1973-01-02 Sumitomo Chemical Co Method for producing dichlorobutene

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2912471A (en) * 1956-03-21 1959-11-10 Distillers Co Yeast Ltd Chlorination of butadiene
DE1090652B (en) * 1956-03-21 1960-10-13 Distillers Co Yeast Ltd A process for the preparation of dichlorobutenes
US2928884A (en) * 1956-03-22 1960-03-15 Distillers Co Yeast Ltd Chlorination of butadiene
DE1090654B (en) * 1956-03-22 1960-10-13 Distillers Co Yeast Ltd A process for the preparation of dichlorobutenes
DE1078109B (en) * 1956-05-15 1960-03-24 Distillers Co Yeast Ltd A process for the preparation of dichlorobutenes
DE1090655B (en) * 1956-05-15 1960-10-13 Distillers Co Yeast Ltd A process for the preparation of dichlorobutenes
US3058966A (en) * 1959-06-29 1962-10-16 Exxon Research Engineering Co Polymers of halogenated alicyclic and straight chain monomers
US3708548A (en) * 1968-12-10 1973-01-02 Sumitomo Chemical Co Method for producing dichlorobutene

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