GB718485A - Manufacture of ethyl toluenes and methyl styrenes - Google Patents

Manufacture of ethyl toluenes and methyl styrenes

Info

Publication number
GB718485A
GB718485A GB30692/52A GB3069252A GB718485A GB 718485 A GB718485 A GB 718485A GB 30692/52 A GB30692/52 A GB 30692/52A GB 3069252 A GB3069252 A GB 3069252A GB 718485 A GB718485 A GB 718485A
Authority
GB
United Kingdom
Prior art keywords
mixture
fraction
isomer
per cent
toluene
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
GB30692/52A
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.)
Dow Chemical Co
Original Assignee
Dow Chemical 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
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Publication of GB718485A publication Critical patent/GB718485A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
    • C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
    • C07C15/46—Styrene; Ring-alkylated styrenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C07C2/68—Catalytic processes with halides

Abstract

Toluene is ethylated in the presence of a Friedel-Crafts' catalyst and the ethylation mixture fractionally distilled to obtain a fraction rich in toluene, a fraction rich in o-ethyltoluene, and a fraction rich in a mixture of m- and p-ethyltoluenes and containing not more than 0.5 per cent by weight of the o isomer. This last fraction may be dehydrogenated and a fraction consisting of m- and p-methylstyrenes and less than 0.5 per cent of o-isomer, indane, and indene recovered. This is polymerizable to colourless, thermoplastic resins. The ethylation is preferably effected with ethylene and activated aluminium chloride, e.g. at 90-101 DEG C., in the presence of the recycled o-ethyltoluene fraction and poly-ethyltoluenes whereby formation of the desired products is enhanced. Unreacted toluene is also recycled. The products are fractionated under reduced pressure, and a fraction containing o-, m- and p-ethyltoluenes separated and refractionated to recover a mixture of m- and p-isomers usually with less than 0.2 per cent of o-isomer. This mixture is dehydrogenated with or without gaseous diluents and catalysts, preferably in admixture with steam and with solid or fluidized catalysts at 550-700 DEG C. The product is fractionally distilled, preferably in a series of columns at reduced pressure, to recover a mixture of m-and p-methylstyrenes. U.S.A. Specification 2,531,327 is referred to.ALSO:Toluene is ethylated in the presence of a Friedel-Crafts' catalyst and the ethylation mixture fractionally distilled to obtain a fraction rich in toluene, a fraction rich in o-ethyltoluene, and a fraction rich in a mixture of m- and p-ethyltoluenes and containing not more than 0.5 per cent. by weight of the o isomer. This last fraction may be dehydrogenated and a fraction consisting of m- and p-methylstyrenes and less than 0.5 per cent. of o-isomer, indane, and indene recovered. The ethylation products are fractionated under reduced pressure, and a fraction containing om- and pethyltoluenes separated and refractionated to recover a mixture of m- and p-isomers usually with less than 0.2 per cent. of o-isomer. This mixture is dehydrogenated and the product fractionally distilled, preferably in a series of columns at reduced pressure, to recover a mixture of m- and p-methylstyrenes.
GB30692/52A 1952-02-28 1952-12-03 Manufacture of ethyl toluenes and methyl styrenes Expired GB718485A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US718485XA 1952-02-28 1952-02-28

Publications (1)

Publication Number Publication Date
GB718485A true GB718485A (en) 1954-11-17

Family

ID=22103983

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30692/52A Expired GB718485A (en) 1952-02-28 1952-12-03 Manufacture of ethyl toluenes and methyl styrenes

Country Status (1)

Country Link
GB (1) GB718485A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0062625A1 (en) * 1981-04-02 1982-10-13 Cosden Technology Inc. Process for the production of vinyltoluene

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0062625A1 (en) * 1981-04-02 1982-10-13 Cosden Technology Inc. Process for the production of vinyltoluene

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