GB667030A - Improvements in and relating to methods of preparing 3-vinylpyrene - Google Patents

Improvements in and relating to methods of preparing 3-vinylpyrene

Info

Publication number
GB667030A
GB667030A GB12450/49A GB1245049A GB667030A GB 667030 A GB667030 A GB 667030A GB 12450/49 A GB12450/49 A GB 12450/49A GB 1245049 A GB1245049 A GB 1245049A GB 667030 A GB667030 A GB 667030A
Authority
GB
United Kingdom
Prior art keywords
pyrene
effected
pyrenes
dehydration
vinyl
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
GB12450/49A
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.)
British Thomson Houston Co Ltd
Original Assignee
British Thomson Houston Co 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
Application filed by British Thomson Houston Co Ltd filed Critical British Thomson Houston Co Ltd
Publication of GB667030A publication Critical patent/GB667030A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/50—Pyrenes; Hydrogenated pyrenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

3-Vinylpyrene is prepared by the vapour phase catalytic dehydration of 3-(a -hydroxyethyl) pyrene with activated alumina. Pyrene is acetylated with, e.g. acetic acid or anhydride, acetyl chloride or bromide to form 3-acetylpyrene which is hydrogenated to 3-(a -hydroxyethyl) pyrene. The acetylation is effected using a Friedel-Crafts' catalyst which may be dissolved or suspended in an inert solvent such as carbon disulphide, nitrobenzene, and carbon tetrachloride, preferably at 20-45 DEG C. The product is hydrogenated and the ketone separated from the organic layer by distillation. Hydrogenation to the alcohol may be effected with platinum, platinum oxide, palladium or copper chromite as catalyst, preferably at pressures of 100-3000 p.s.i. and in a solvent such as methanol. Dehydration to vinyl pyrene may be effected by dissolving the alcohol in, e.g., benzene, toluene or dioxane and feeding to a column packed with alumina pellets at, e.g., 340-360 DEG C., and about 6 mm. The product may be purified by recrystallization. Polymerization may be inhibited by catechol or hydroquinone. Polymers or copolymers are used in the plastics and coating arts and as dielectrics. The Specification as open to inspection under Sect. 91 comprises the preparation of other vinyl pyrenes starting with other acetyl pyrene isomers. Polyacetyl pyrenes obtained by further acetylation yield polyvinyl pyrenes. Dehydration of the carbinol may be effected with chemical dehydrating agents such as KHSO4, ZnCl2, and P2O5, or catalysts containing activated alumina with oxides of Cr, W, Mo or Mn. 3-Vinyl pyrene may also be prepared by decarboxylating pyrenyl - 3 - acrylic acid which is dissolved in benzene and quinoline and passed through copper borate-alumina at 520-580 DEG C. and 10-20 mm. This subject-matter does not appear in the Specification as accepted.
GB12450/49A 1948-05-13 1949-05-10 Improvements in and relating to methods of preparing 3-vinylpyrene Expired GB667030A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US667030XA 1948-05-13 1948-05-13

Publications (1)

Publication Number Publication Date
GB667030A true GB667030A (en) 1952-02-20

Family

ID=22071155

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12450/49A Expired GB667030A (en) 1948-05-13 1949-05-10 Improvements in and relating to methods of preparing 3-vinylpyrene

Country Status (1)

Country Link
GB (1) GB667030A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2646792A1 (en) * 1975-10-23 1977-04-28 Mitsubishi Petrochemical Co PROCESS FOR THE PREPARATION OF ALPHA (ARYL SUBSTITUTED) PROPIONIC ACIDS
US5254720A (en) * 1992-12-28 1993-10-19 Ethyl Corporation Process for preparing aryl-substituted aliphatic carboxylic acids and their alkyl esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2646792A1 (en) * 1975-10-23 1977-04-28 Mitsubishi Petrochemical Co PROCESS FOR THE PREPARATION OF ALPHA (ARYL SUBSTITUTED) PROPIONIC ACIDS
US5254720A (en) * 1992-12-28 1993-10-19 Ethyl Corporation Process for preparing aryl-substituted aliphatic carboxylic acids and their alkyl esters

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