Regioselective dialkylation of naphthalene

Smith, Keith; Roberts, Simon D.

doi:10.1016/s0920-5861(00)00339-4

Cited by 24 publications

(21 citation statements)

References 19 publications

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“…We have already given a preliminary account of some of the results. 9 We now report the full details of the successful production of 2,6-di-tert-butylnaphthalene, which can be easily separated from the reaction mixture by crystallisation.…”

Section: Introductionmentioning

confidence: 99%

Study of regioselective dialkylation of naphthalene in the presence of reusable zeolite catalysts

2003

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Highly regioselective dialkylation of naphthalene using various alkylating agents can be achieved over zeolite catalysts. For example, the tert-butylation of naphthalene (1) using tert-butanol in cyclohexane over a dealuminated H-Mordenite (HM) zeolite has been optimised to give a 60% yield of 2.6-di-tert-butylnaphthalene (3) with a 2.6/2.7 ratio of over 50. This has been achieved by varying the reaction time, temperature, solvent, pressure, amount of tert-butanol, solvent and catalyst, Si/Al ratio of the catalyst, and the mode of addition. The zeolites can be easily regenerated by heating and reused.

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Section: Introductionmentioning

confidence: 99%

Study of regioselective dialkylation of naphthalene in the presence of reusable zeolite catalysts

2003

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“…Compared with poly(ethylene terephthalate) (PET), in addition to its excellent properties as a gas barrier, PEN has good thermal and chemical stability as well as mechanical properties, leading to its wide application in electronics components, insulation material, food containers, aviation, and so on (Song et al, 1993;Tsutsui et al, 2004;Wu et al, 2010;. Highly regioselective synthesis of 2,6-DKN can be achieved over different molecular sieve catalysts using various alkylating agents and solvents (Brzozowski et al, 2012;Liu et al, 1997;Smith et al, 2000;Smith et al, 2003;Smith et al, 2012;Song et al, 2000;Sugi et al, 2008). Liu et al (1997) reported that the alkylation of naphthalene with tbutanol should be both practical and attractive not only because of the high activity, but also due to the easy separation of the desired product from the reaction mixtures by crystallization.…”

Section: Introductionmentioning

confidence: 99%

“…Liu et al (1997) reported that the alkylation of naphthalene with tbutanol should be both practical and attractive not only because of the high activity, but also due to the easy separation of the desired product from the reaction mixtures by crystallization. Smith et al (2000) surveyed the dialkylation of naphthalene over a dealuminated mordenite molecular sieve using tertbutanol as an alkylating agent. The experimental results showed that a 60% yield of 2,6-di-tertbutylnaphthalene was obtained with a 2,6/2,7-ratio of over 50.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,6-Dimethylnaphthalene Over Sapo-11, Sapo-5 and Mordenite Molecular Sieves

Wang

Liu

Wei

et al. 2017

Braz. J. Chem. Eng.

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-Shape-selective methylation of naphthalene over SAPO-11, SAPO-5 and mordenite molecular sieves were carried out in a fixed-bed flow reactor under atmospheric pressure. Methanol and mesitylene were used as methylation and solvent agents. The experiment results showed that SAPO-11 exhibited higher stability, higher selectivity of 2,6-dimethylnaphthalene (2,6-DMN) and higher 2,6-/2,7-DMN ratio than SAPO-5 and mordenite molecular sieves. The catalytic performances for the methylation of naphthalene were mainly related to the pore structure of the catalysts. The comparison of the spent SAPO-11 with fresh SAPO-11 suggested that structure collapse of the SAPO-11 by dealumination was occurred during the methylation of naphthalene with methanol, which may have been caused by high temperature steam from water produced in the reaction or by high temperature methanol vapor.

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“…46,47 By studying the above reaction in more detail, we have previously shown that highly regioselective di-tert-butylation of naphthalene could be achieved over zeolite H-mordenite using tert-butyl alcohol as the alkylating agent under autoclave conditions. 34,35 The process was a convenient, high yielding and highly regioselective method for the synthesis of 2,6-di-tert-butylnaphthalene, which was produced in 60% yield, along with only 1% of 2,7-di-tert-butylnaphthalene, i.e. a 2,6/2,7 ratio of over 50.…”

Section: Introductionmentioning

confidence: 99%

Highly regioselective di-tert-amylation of naphthalene over reusable H-mordenite zeolite

et al. 2012

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Highly regioselective di-tert-amylation of naphthalene using different alcohols can be achieved over a H-mordenite (HM) zeolite. For example, the tert-amylation of naphthalene using tert-amyl alcohol in cyclohexane over HM (Si/Al = 10) zeolite has been optimised to give a 70% yield of 2,6-dialkylnaphthalenes, of which 2,6-di-tertamylnaphthalene was produced in 46% yield along with 2-tert-amyl-6-tertbutylnaphthalene (23%) and 2,6-di-tert-butylnaphthalene (1%). This has been achieved by varying the reaction time, temperature, pressure and amounts of tert-amyl alcohol and zeolite. No 2,7-dialkylnaphathalenes were seen under the conditions tried. The zeolites can be easily regenerated by heating and then reused.

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Regioselective dialkylation of naphthalene

Cited by 24 publications

References 19 publications

Study of regioselective dialkylation of naphthalene in the presence of reusable zeolite catalysts

Study of regioselective dialkylation of naphthalene in the presence of reusable zeolite catalysts

Synthesis of 2,6-Dimethylnaphthalene Over Sapo-11, Sapo-5 and Mordenite Molecular Sieves

Highly regioselective di-tert-amylation of naphthalene over reusable H-mordenite zeolite

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