Alkylation–acylation of p-xylene with γ-butyrolactone or vinylacetic acid catalyzed by heteropolyacid supported on silica
Kamiya, Y; Ooka, Y; Obara, C; Ohnishi, R; Fujita, T; Kurata, Y; Tsuji, K; Nakajyo, T; Okuhara, T
| HERO ID | 854632 |
|---|---|
| In Press | No |
| Year | 2007 |
| Title | Alkylation–acylation of p-xylene with γ-butyrolactone or vinylacetic acid catalyzed by heteropolyacid supported on silica |
| Authors | Kamiya, Y; Ooka, Y; Obara, C; Ohnishi, R; Fujita, T; Kurata, Y; Tsuji, K; Nakajyo, T; Okuhara, T |
| Journal | Journal of Molecular Catalysis A: Chemical |
| Volume | 262 |
| Issue | 1-2 |
| Page Numbers | 77-85 |
| Abstract | Friedel-Crafts-type reaction of p-xylene with gamma-butyrolactone or vinylacetic acid over H4SiW12O40 supported on SiO2 have been investigated with different loadings of H4SiW12O40. The catalytic performance of H4SiW12O40/SiO2 have been compared with those of typical solid acid catalysts such as zeolites, ion-exchanged resins, and binary oxides. H4SiW12O40 supported on SiO2 was superior in activity and selectivity to 5,8-dimethyl-alpha-tetralone compared to other catalysts for the reaction between p-xylene and gamma-butyrolactone. SiO2-supported H4SiW12O40 also was efficient for the formation of 3,4,7-tetramethyl-alpha-indanone from p-xylene and vinylacetic acid. The formation of 5,8-dimethyl-a-tetralone is extremely sensitive to the load of H4SiW12O40 on SiO2, reaching a maximum at approximately 30 wt%, due to the change in the acid amount of the outermost surface as determined by benzonitrile-temperature programmed desorption. By analogy with reaction between 1,3,5-trimethylbenzene and gamma-butyrolactone, the reaction pathway involves initial alkylation of p-xylene with gamma-butyrolactone, followed by intramolecular acylation to 5,8-dimethyl-alpha-tetralone, which was supported by quantum calculations of gamma-butyrolactone and protonated gamma-butyrolactone. (c) 2006 Elsevier B.V. All rights reserved. |
| Doi | 10.1016/j.molcata.2006.08.055 |
| Wosid | WOS:000244183400012 |
| Url | http://linkinghub.elsevier.com/retrieve/pii/S1381116906011290 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | heteropolyacid; Friedel-Crafts reaction; gamma-butyrolactone; vinylacetic acid |
| Is Qa | No |