Balsohn alkylation

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The Balsohn alkylation is a name reaction of organic chemistry , which was published in 1879 by M. Balsohn.

Overview reaction

In the Balson alkylation, benzene reacts with ethene in the presence of aluminum chloride to form ethylbenzene .

Balsohn overview V2.svg

Reaction mechanism

In the proposed reaction mechanism, the ethene initially reacts with the aluminum chloride to form a carbenium ion . The carbenium ion is then nucleophilically attacked by the aromatic ring of benzene. After a proton has been split off, the desired ethylbenzene is formed.

Balsohn mechanism V2.svg

modification

In addition to aluminum chloride, sulfuric acid, phosphoric acid, phosphorus pentoxide and boron trifluoride can also be used for activation. In addition, the reaction is not limited to ethene and benzene; other alkenes and aromatics can also be converted in the Balson alkylation. The alkylation of the following para / ortho - regioselectivity .

application

Balson alkylation has already been used for industrial production.

See also

Individual evidence

  1. ↑ a b c d e Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , doi : 10.1002 / 9780470638859 .
  2. ↑ Ernest M. Hodnett, Charles F. Feldman: Kinetics of the Friedel-Crafts Ethylation of Benzene with Ethylene and with Ethylene-C14 . In: Journal of the American Chemical Society . tape 81 , no. 7 , April 1, 1959, pp. 1638-1640 , doi : 10.1021 / ja01516a032 .
  3. ↑ UN Ipatieff, BB Corson, Herman Pines: Influence of Sulfuric Acid Concentration upon reaction between Olefins and Benzene . In: Journal of the American Chemical Society . tape 58 , no. 6 , June 1, 1936, p. 919-922 , doi : 10.1021 / ja01297a021 .
  4. ↑ UN Ipatieff, Herman Pines, VI Komarewsky: Phosphoric Acid as the Catalyst for Alkylation of Aromatic Hydrocarbons . In: Industrial & Engineering Chemistry . tape 28 , no. 2 , February 1, 1936, p. 222-223 , doi : 10.1021 / ie50314a019 .
  5. ↑ Vladimir N. Ipatieff, Aristid V. Grosse: Reaction of Paraffins with Olefins1 . In: Journal of the American Chemical Society . tape 57 , no. 9 , September 1, 1935, pp. 1616–1621 , doi : 10.1021 / ja01312a034 .
  6. ^ Henry Gilman, Nathaniel O. Calloway, Robert R. Burtner: Orientation in the Furan Series. IX. The Friedel — Crafts Reaction with 2-Furfural . In: Journal of the American Chemical Society . tape 57 , no. 5 , May 1, 1935, p. 906-907 , doi : 10.1021 / ja01308a037 .
  7. ↑ JW Cook, EC Dodds, CL Hewett: A Synthetic Oestrus-Exciting Compound . In: Nature . tape 131 , no. 3298 , 1933, pp. 56-57 , doi : 10.1038 / 131056b0 .
  8. ^ Joseph B. Niederl, Charles H. Riley: The Addition of Phenols to Arylenes. The Synthesis of Phenylthymol and its Isomers . In: Journal of the American Chemical Society . tape 56 , no. 11 , November 1, 1934, pp. 2412–2414 , doi : 10.1021 / ja01326a059 .
  9. ↑ Preparation of 1,1,3,4,4,6-hexamethyl-1,2,3,4-tetra-hydronaphthalenes . March 13, 1991 ( google.com [accessed May 26, 2019]).