Shape-selective isopropylation of naphthalene over H-mordenite catalysts for environmentally friendly synthesis of 2,6-dialkylnaphthalene

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Abstract

Recent development of advanced polymer materials such as polyethylene naphthalate, polybutylene naphthalate and liquid crystalline polymers has created an increasing demand for 2,6-dialkylnaphthalene, which has spurred interest in shape-selective naphthalene alkylation. This work deals with mordenite-catalyzed shape-selective naphthalene isopropylation to produce 2,6-diisopropylnaphthalene (2,6-DIPN). Effects of dealumination of mordenite on the structural and acidic characteristics and on the shape selectivity and activity were examined by physicochemical analysis, TPD, solid-state 27Al and 29Si MAS NMR, XRD, as well as catalytic alkylation reactions. Dealumination removes octahedral Al species as well as tetrahedral Al species, decreases the unit cell dimensions and reduces the number of strong acid sites in mordenites. Proper dealumination can improve selectivity to 2,6-DIPN from 33 to 61 % and significantly increases 2,6/2,7 ratio. Improved selectivity to 2,6-DIPN upon proper dealumination was attributed to the decrease in mordenite acidity, reduction in unit cell dimension and removal of some strong acid sites. However, neither the change in selectivity nor that in activity is a simple function of dealumination degree or SiO2/Al2O3 ratio. Some minor difference in the apparent framework SiO2/Al2O3 ratio can result in a major difference in activity or selectivity. There exist optimum conditions of dealumination as well as optimum reaction conditions for achieving higher selectivity to 2,6-DIPN.

Original languageEnglish (US)
Pages (from-to)477-496
Number of pages20
JournalComptes Rendus de l'Academie des Sciences - Series IIc: Chemistry
Volume3
Issue number6
DOIs
StatePublished - Jan 1 2000

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Catalysts
Alkylation
Acids
Liquid crystal polymers
Polyethylene
Temperature programmed desorption
Acidity
Polymers
Nuclear magnetic resonance
mordenite
2,6-diisopropylnaphthalene
naphthalene
polybutene

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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title = "Shape-selective isopropylation of naphthalene over H-mordenite catalysts for environmentally friendly synthesis of 2,6-dialkylnaphthalene",
abstract = "Recent development of advanced polymer materials such as polyethylene naphthalate, polybutylene naphthalate and liquid crystalline polymers has created an increasing demand for 2,6-dialkylnaphthalene, which has spurred interest in shape-selective naphthalene alkylation. This work deals with mordenite-catalyzed shape-selective naphthalene isopropylation to produce 2,6-diisopropylnaphthalene (2,6-DIPN). Effects of dealumination of mordenite on the structural and acidic characteristics and on the shape selectivity and activity were examined by physicochemical analysis, TPD, solid-state 27Al and 29Si MAS NMR, XRD, as well as catalytic alkylation reactions. Dealumination removes octahedral Al species as well as tetrahedral Al species, decreases the unit cell dimensions and reduces the number of strong acid sites in mordenites. Proper dealumination can improve selectivity to 2,6-DIPN from 33 to 61 {\%} and significantly increases 2,6/2,7 ratio. Improved selectivity to 2,6-DIPN upon proper dealumination was attributed to the decrease in mordenite acidity, reduction in unit cell dimension and removal of some strong acid sites. However, neither the change in selectivity nor that in activity is a simple function of dealumination degree or SiO2/Al2O3 ratio. Some minor difference in the apparent framework SiO2/Al2O3 ratio can result in a major difference in activity or selectivity. There exist optimum conditions of dealumination as well as optimum reaction conditions for achieving higher selectivity to 2,6-DIPN.",
author = "Chunshan Song",
year = "2000",
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doi = "10.1016/S1387-1609(00)01164-6",
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TY - JOUR

T1 - Shape-selective isopropylation of naphthalene over H-mordenite catalysts for environmentally friendly synthesis of 2,6-dialkylnaphthalene

AU - Song, Chunshan

PY - 2000/1/1

Y1 - 2000/1/1

N2 - Recent development of advanced polymer materials such as polyethylene naphthalate, polybutylene naphthalate and liquid crystalline polymers has created an increasing demand for 2,6-dialkylnaphthalene, which has spurred interest in shape-selective naphthalene alkylation. This work deals with mordenite-catalyzed shape-selective naphthalene isopropylation to produce 2,6-diisopropylnaphthalene (2,6-DIPN). Effects of dealumination of mordenite on the structural and acidic characteristics and on the shape selectivity and activity were examined by physicochemical analysis, TPD, solid-state 27Al and 29Si MAS NMR, XRD, as well as catalytic alkylation reactions. Dealumination removes octahedral Al species as well as tetrahedral Al species, decreases the unit cell dimensions and reduces the number of strong acid sites in mordenites. Proper dealumination can improve selectivity to 2,6-DIPN from 33 to 61 % and significantly increases 2,6/2,7 ratio. Improved selectivity to 2,6-DIPN upon proper dealumination was attributed to the decrease in mordenite acidity, reduction in unit cell dimension and removal of some strong acid sites. However, neither the change in selectivity nor that in activity is a simple function of dealumination degree or SiO2/Al2O3 ratio. Some minor difference in the apparent framework SiO2/Al2O3 ratio can result in a major difference in activity or selectivity. There exist optimum conditions of dealumination as well as optimum reaction conditions for achieving higher selectivity to 2,6-DIPN.

AB - Recent development of advanced polymer materials such as polyethylene naphthalate, polybutylene naphthalate and liquid crystalline polymers has created an increasing demand for 2,6-dialkylnaphthalene, which has spurred interest in shape-selective naphthalene alkylation. This work deals with mordenite-catalyzed shape-selective naphthalene isopropylation to produce 2,6-diisopropylnaphthalene (2,6-DIPN). Effects of dealumination of mordenite on the structural and acidic characteristics and on the shape selectivity and activity were examined by physicochemical analysis, TPD, solid-state 27Al and 29Si MAS NMR, XRD, as well as catalytic alkylation reactions. Dealumination removes octahedral Al species as well as tetrahedral Al species, decreases the unit cell dimensions and reduces the number of strong acid sites in mordenites. Proper dealumination can improve selectivity to 2,6-DIPN from 33 to 61 % and significantly increases 2,6/2,7 ratio. Improved selectivity to 2,6-DIPN upon proper dealumination was attributed to the decrease in mordenite acidity, reduction in unit cell dimension and removal of some strong acid sites. However, neither the change in selectivity nor that in activity is a simple function of dealumination degree or SiO2/Al2O3 ratio. Some minor difference in the apparent framework SiO2/Al2O3 ratio can result in a major difference in activity or selectivity. There exist optimum conditions of dealumination as well as optimum reaction conditions for achieving higher selectivity to 2,6-DIPN.

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JO - Comptes Rendus de l'Academie des Sciences - Series IIc: Chemistry

JF - Comptes Rendus de l'Academie des Sciences - Series IIc: Chemistry

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