GB885872A - Improvements relating to the production of alkenyl aromatic compounds - Google Patents

Improvements relating to the production of alkenyl aromatic compounds

Info

Publication number
GB885872A
GB885872A GB27555/60A GB2755560A GB885872A GB 885872 A GB885872 A GB 885872A GB 27555/60 A GB27555/60 A GB 27555/60A GB 2755560 A GB2755560 A GB 2755560A GB 885872 A GB885872 A GB 885872A
Authority
GB
United Kingdom
Prior art keywords
product
butadiene
benzene
reacted
believed
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
GB27555/60A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB885872A publication Critical patent/GB885872A/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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C07C2527/12—Fluorides
    • C07C2527/1213—Boron fluoride

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epoxy Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Epoxy resins are obtained by reacting at least 2 mols of a conjugated diene (which may be cyclic or chlorinated) with 1 mol of an aromatic hydrocarbon in the presence of boron trifluoride or a complex thereof, epoxidising the ethylenically unsaturated aromatic compound obtained and curing, e.g. with phthalic anhydride. In the Examples (1) benzene is reacted with butadiene to yield a product believed to contain compounds of the formula: <FORM:0885872/IV (a)/1> which is epoxidized with peracetic acid and cured with 0,85 mol of phthalic anhydride per epoxide equivalent for 6 hours at 120 DEG C. and 15 hours at 160 DEG C., (2) toluene is reacted with butadiene to yield a product comprising mono- and dibutenyl toluenes and compounds believed to be of the formula <FORM:0885872/IV (a)/2> which is epoxidized and can be similarly cured.ALSO:The reaction of a conjugated diene with an aromatic hydrocarbon to yield an olefinically unsaturated product is effected with a mol ratio of diene to aromatic hydrocarbon of at least 2:1 in the presence of boron trifluoride or a complex thereof. The aromatic hydrocarbon may be benzene, toluene, xylene, naphthalene, alkylated naphthalene, diphenyl, diphenyl methane or anthracene and the diene butadiene, isoprene, piperylene, 2-methylpentadiene-1,3, pentadiene-1,3, cyclopentadiene, methyl-cyclopentadiene, hexadiene-1,3,1-chloro-2-methyl-butadiene-1,3 or chloroprene, the ratio of diene to aromatic being 2-8:1. The temperature may be 0 DEG C.-30 DEG C. In the examples (1) benzene is reacted with butadiene the main product of which is believed to be of the formula <FORM:0885872/IV (b)/1> (2) toluene is reacted with butadiene which is believed to result in <FORM:0885872/IV (b)/2> as well as mono- and di-butenyl toluenes. Epoxides of the products of the above process are obtained by oxidation, e.g. with hydrogen peroxide in the presence of formic acid or with peracetic acid, perbenzoic acid or monoperphthalic acid, preferably in the presence of chloroform, ethyl ether, methlene chloride, benzene or ethyl acetate as solvent at -20 DEG C. to 100 DEG C. The product of example (1) is epoxidised with 1.3 mols of peracetic acid for every equivalent of double bonds in the product and the product of example (2) is epoxidised with formic acid and hydrogen peroxide.
GB27555/60A 1959-08-13 1960-08-09 Improvements relating to the production of alkenyl aromatic compounds Expired GB885872A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH885872X 1959-08-13

Publications (1)

Publication Number Publication Date
GB885872A true GB885872A (en) 1961-12-28

Family

ID=4545263

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27555/60A Expired GB885872A (en) 1959-08-13 1960-08-09 Improvements relating to the production of alkenyl aromatic compounds

Country Status (2)

Country Link
GB (1) GB885872A (en)
NL (1) NL254823A (en)

Also Published As

Publication number Publication date
NL254823A (en)

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