Catalytic studies toward synthesis of 2,6-dimethylnaphthalene from 1-(p -Tolyl)-2-methylbutane

Kari Vahteristo (Corresponding Author), Kari-Matti Sahala, Salme Koskimies

Research output: Contribution to journalArticleScientificpeer-review

2 Citations (Scopus)

Abstract

In this work experiments have been performed in order to study the synthesis of 2,6-dimethylnaphthalene (DMN) via dehydrocyclizing 1-(p-tolyl)-2-methylbutane over Pt/SiO2, V/Ca/Al2O3, and unimpregnated or potassium-impregnated Cr2O3/Al2O3 catalysts. The obtained liquid product mixture consisted of 1,6-cyclization products (dimethylnaphthalenes) and dealkylated 1,6-cyclization products (2-methylnaphthalene and naphthalene), 1,5-cyclization products (trimethylindanes and -indenes), and fragmentation products (mainly p-xylene and 3-(p-tolyl)-propylenes) and 1-(p-tolyl)-2-methylbutenes. Among 10 possible DMN isomers 1,5-, 1,6-, 2,6-, and 2,7-DMN were identified. Metal catalysts V/Ca/Al2O3 (5 wt % vanadium) and Pt/SiO2 (1 wt % platinum) were slightly more active than unimpregnated commercial Cr2O3/Al2O3. After 1 h on-stream time the conversion of 1-(p-tolyl)-2-methylbutane was 96 mol % when the artificial contact time (1/weight-hourly space velocity (WHSV)) was 5.7 h at 783 K over unimpregnated Cr2O3/Al2O3. Potassium impregnation decreased the conversion into 84 mol % because of the decreased Brunauer−Emmett−Teller surface area (from 97 m2/g unimpregnated to 70 m2/g potassium-impregnated catalyst).
Original languageEnglish
Pages (from-to)4018-4025
JournalIndustrial & Engineering Chemistry Research
Volume49
Issue number9
DOIs
Publication statusPublished - 2010
MoE publication typeA1 Journal article-refereed

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Cyclization
Potassium
Catalysts
Indenes
Vanadium
Xylene
Naphthalene
Platinum
Impregnation
Isomers
Metals
Liquids
isopentane
2,6-dimethylnaphthalene
Experiments

Cite this

Vahteristo, Kari ; Sahala, Kari-Matti ; Koskimies, Salme. / Catalytic studies toward synthesis of 2,6-dimethylnaphthalene from 1-(p -Tolyl)-2-methylbutane. In: Industrial & Engineering Chemistry Research. 2010 ; Vol. 49, No. 9. pp. 4018-4025.
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title = "Catalytic studies toward synthesis of 2,6-dimethylnaphthalene from 1-(p -Tolyl)-2-methylbutane",
abstract = "In this work experiments have been performed in order to study the synthesis of 2,6-dimethylnaphthalene (DMN) via dehydrocyclizing 1-(p-tolyl)-2-methylbutane over Pt/SiO2, V/Ca/Al2O3, and unimpregnated or potassium-impregnated Cr2O3/Al2O3 catalysts. The obtained liquid product mixture consisted of 1,6-cyclization products (dimethylnaphthalenes) and dealkylated 1,6-cyclization products (2-methylnaphthalene and naphthalene), 1,5-cyclization products (trimethylindanes and -indenes), and fragmentation products (mainly p-xylene and 3-(p-tolyl)-propylenes) and 1-(p-tolyl)-2-methylbutenes. Among 10 possible DMN isomers 1,5-, 1,6-, 2,6-, and 2,7-DMN were identified. Metal catalysts V/Ca/Al2O3 (5 wt {\%} vanadium) and Pt/SiO2 (1 wt {\%} platinum) were slightly more active than unimpregnated commercial Cr2O3/Al2O3. After 1 h on-stream time the conversion of 1-(p-tolyl)-2-methylbutane was 96 mol {\%} when the artificial contact time (1/weight-hourly space velocity (WHSV)) was 5.7 h at 783 K over unimpregnated Cr2O3/Al2O3. Potassium impregnation decreased the conversion into 84 mol {\%} because of the decreased Brunauer−Emmett−Teller surface area (from 97 m2/g unimpregnated to 70 m2/g potassium-impregnated catalyst).",
author = "Kari Vahteristo and Kari-Matti Sahala and Salme Koskimies",
year = "2010",
doi = "10.1021/ie9008887",
language = "English",
volume = "49",
pages = "4018--4025",
journal = "Industrial & Engineering Chemistry Research",
issn = "0888-5885",
publisher = "American Chemical Society",
number = "9",

}

Catalytic studies toward synthesis of 2,6-dimethylnaphthalene from 1-(p -Tolyl)-2-methylbutane. / Vahteristo, Kari (Corresponding Author); Sahala, Kari-Matti; Koskimies, Salme.

In: Industrial & Engineering Chemistry Research, Vol. 49, No. 9, 2010, p. 4018-4025.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Catalytic studies toward synthesis of 2,6-dimethylnaphthalene from 1-(p -Tolyl)-2-methylbutane

AU - Vahteristo, Kari

AU - Sahala, Kari-Matti

AU - Koskimies, Salme

PY - 2010

Y1 - 2010

N2 - In this work experiments have been performed in order to study the synthesis of 2,6-dimethylnaphthalene (DMN) via dehydrocyclizing 1-(p-tolyl)-2-methylbutane over Pt/SiO2, V/Ca/Al2O3, and unimpregnated or potassium-impregnated Cr2O3/Al2O3 catalysts. The obtained liquid product mixture consisted of 1,6-cyclization products (dimethylnaphthalenes) and dealkylated 1,6-cyclization products (2-methylnaphthalene and naphthalene), 1,5-cyclization products (trimethylindanes and -indenes), and fragmentation products (mainly p-xylene and 3-(p-tolyl)-propylenes) and 1-(p-tolyl)-2-methylbutenes. Among 10 possible DMN isomers 1,5-, 1,6-, 2,6-, and 2,7-DMN were identified. Metal catalysts V/Ca/Al2O3 (5 wt % vanadium) and Pt/SiO2 (1 wt % platinum) were slightly more active than unimpregnated commercial Cr2O3/Al2O3. After 1 h on-stream time the conversion of 1-(p-tolyl)-2-methylbutane was 96 mol % when the artificial contact time (1/weight-hourly space velocity (WHSV)) was 5.7 h at 783 K over unimpregnated Cr2O3/Al2O3. Potassium impregnation decreased the conversion into 84 mol % because of the decreased Brunauer−Emmett−Teller surface area (from 97 m2/g unimpregnated to 70 m2/g potassium-impregnated catalyst).

AB - In this work experiments have been performed in order to study the synthesis of 2,6-dimethylnaphthalene (DMN) via dehydrocyclizing 1-(p-tolyl)-2-methylbutane over Pt/SiO2, V/Ca/Al2O3, and unimpregnated or potassium-impregnated Cr2O3/Al2O3 catalysts. The obtained liquid product mixture consisted of 1,6-cyclization products (dimethylnaphthalenes) and dealkylated 1,6-cyclization products (2-methylnaphthalene and naphthalene), 1,5-cyclization products (trimethylindanes and -indenes), and fragmentation products (mainly p-xylene and 3-(p-tolyl)-propylenes) and 1-(p-tolyl)-2-methylbutenes. Among 10 possible DMN isomers 1,5-, 1,6-, 2,6-, and 2,7-DMN were identified. Metal catalysts V/Ca/Al2O3 (5 wt % vanadium) and Pt/SiO2 (1 wt % platinum) were slightly more active than unimpregnated commercial Cr2O3/Al2O3. After 1 h on-stream time the conversion of 1-(p-tolyl)-2-methylbutane was 96 mol % when the artificial contact time (1/weight-hourly space velocity (WHSV)) was 5.7 h at 783 K over unimpregnated Cr2O3/Al2O3. Potassium impregnation decreased the conversion into 84 mol % because of the decreased Brunauer−Emmett−Teller surface area (from 97 m2/g unimpregnated to 70 m2/g potassium-impregnated catalyst).

U2 - 10.1021/ie9008887

DO - 10.1021/ie9008887

M3 - Article

VL - 49

SP - 4018

EP - 4025

JO - Industrial & Engineering Chemistry Research

JF - Industrial & Engineering Chemistry Research

SN - 0888-5885

IS - 9

ER -