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Alkylation of 2-methoxynaphthalene with propylene oxide using titanium and zirconium containing molecular sieves

Brait, Axel and Davis, Mark E. (2000) Alkylation of 2-methoxynaphthalene with propylene oxide using titanium and zirconium containing molecular sieves. Applied Catalysis A: General, 204 (1). pp. 117-127. ISSN 0926-860X. https://resolver.caltech.edu/CaltechAUTHORS:20170816-153452128

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Abstract

Titanium and zirconium containing molecular sieves are active catalysts for the alkylation of 2-methoxynaphthalene (2-MN) with propylene oxide (PO). Temperatures above 423 K are necessary in order to promote the alkylation reaction. A major competing reaction that deactivates the catalyst is the oligomerization of PO that provides for deposition of these oligomers on the catalyst surface. A high 2-MN to PO ratio as well as the addition of PO in a semi-batch mode of operation help minimize the oligomerization reaction. The main reaction products are an O-alkylated product (I) and four C-alkylated products: 1-(2-methoxy-1-naphthyl)-2-propanol (II), 2-(2-methoxy-1-naphthyl)propanol (III), 1-(6-methoxy-2-naphthyl)-2-propanol (IV) and 2-(6-methoxy-2-naphthyl)propanol (V). The conversion of the limiting compound (PO) can be as high as 50% with selectivities towards the desired product V ranging from 12 to 20%. The ratio of 2,6- to 1,2-product is 1.6 for Ti-BEA, while Zr-BEA shows a value of 3.0. The shape-selective effect of the molecular sieve catalysts can be enhanced by passivation or poisoning of the outer surface of the catalyst by treatment with tetraethylorthosilicate (TEOS), tris[2-(diphenylphosphino)ethyl]-phosphine (TETRAPHOS-II), ethylenediaminetetraacetic acid (EDTA) or hydrogen peroxide (H_2O_2). For these cases, the 2,6- to 1,2-products ratios can reach values of up to 4. No leaching of Ti or Zr from the molecular sieve materials is observed.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1016/S0926-860X(00)00510-XDOIArticle
http://www.sciencedirect.com/science/article/pii/S0926860X0000510XPublisherArticle
ORCID:
AuthorORCID
Davis, Mark E.0000-0001-8294-1477
Additional Information:© 2000 Elsevier Science B.V. Received 13 December 1999, Revised 1 March 2000, Accepted 3 March 2000, Available online 15 September 2000.
Subject Keywords:Alkylation; Lewis acid; Aromatics; Propylene oxide; Naproxen; Molecular sieves
Issue or Number:1
Record Number:CaltechAUTHORS:20170816-153452128
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170816-153452128
Official Citation:Axel Brait, Mark E Davis, Alkylation of 2-methoxynaphthalene with propylene oxide using titanium and zirconium containing molecular sieves, Applied Catalysis A: General, Volume 204, Issue 1, 6 November 2000, Pages 117-127, ISSN 0926-860X, https://doi.org/10.1016/S0926-860X(00)00510-X. (http://www.sciencedirect.com/science/article/pii/S0926860X0000510X)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:80515
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:16 Aug 2017 23:28
Last Modified:09 Mar 2020 13:18

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