Zeolite-catalyzed ring-shift isomerization of sym-octahydrophenanthrene and conformational isomerization of cis-decahydronaphthalene

Chunshan Song; Kimberly Moffatt

doi:10.1016/0927-6513(94)00023-9

Zeolite-catalyzed ring-shift isomerization of sym-octahydrophenanthrene and conformational isomerization of cis-decahydronaphthalene

Chunshan Song
, Kimberly Moffatt

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

This paper reports on two zeolite-catalyzed isomerization reactions of polycyclic hydrocarbons. The first is the transformation of 1,2,3,4,5,6,7,8-octahydrophenanthrene (sym-OHP) to 1,2,3,4,5,6,7,8-octahydroanthracene (sym-OHAn), which we call ring-shift isomerization. Among the Y zeolites and mordenites tested, a proton-form mordenite (HML8) with relatively lower SiO₂/Al₂O₃ ratio afforded a higher yield of sym-OHAn with a higher sym-OHAn/sym-OHP ratio. The best selectivities towards sym-OHAn with HML8 at 250°C are 89-91% at 58-59% conversion of sym-OHP in decalin and in mesitylene solvents. The second is the conversion of cis-decahydronaphthalene (cis-DeHN) to trans-DeHN, which may be called conformational isomerization. For this reaction, a La ion-exchanged Y zeolite (LaHY) displayed the best selectivity with a trans-DeHN/cis-DeHN ratio of over 10 at 250°C.

Original language	English (US)
Pages (from-to)	459-466
Number of pages	8
Journal	Microporous Materials
Volume	2
Issue number	5
DOIs	https://doi.org/10.1016/0927-6513(94)00023-9
State	Published - Jan 1 1994

All Science Journal Classification (ASJC) codes

General Chemistry
General Materials Science
General Engineering

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title = "Zeolite-catalyzed ring-shift isomerization of sym-octahydrophenanthrene and conformational isomerization of cis-decahydronaphthalene",

abstract = "This paper reports on two zeolite-catalyzed isomerization reactions of polycyclic hydrocarbons. The first is the transformation of 1,2,3,4,5,6,7,8-octahydrophenanthrene (sym-OHP) to 1,2,3,4,5,6,7,8-octahydroanthracene (sym-OHAn), which we call ring-shift isomerization. Among the Y zeolites and mordenites tested, a proton-form mordenite (HML8) with relatively lower SiO2/Al2O3 ratio afforded a higher yield of sym-OHAn with a higher sym-OHAn/sym-OHP ratio. The best selectivities towards sym-OHAn with HML8 at 250°C are 89-91\% at 58-59\% conversion of sym-OHP in decalin and in mesitylene solvents. The second is the conversion of cis-decahydronaphthalene (cis-DeHN) to trans-DeHN, which may be called conformational isomerization. For this reaction, a La ion-exchanged Y zeolite (LaHY) displayed the best selectivity with a trans-DeHN/cis-DeHN ratio of over 10 at 250°C.",

author = "Chunshan Song and Kimberly Moffatt",

year = "1994",

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doi = "10.1016/0927-6513(94)00023-9",

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AU - Moffatt, Kimberly

PY - 1994/1/1

Y1 - 1994/1/1

N2 - This paper reports on two zeolite-catalyzed isomerization reactions of polycyclic hydrocarbons. The first is the transformation of 1,2,3,4,5,6,7,8-octahydrophenanthrene (sym-OHP) to 1,2,3,4,5,6,7,8-octahydroanthracene (sym-OHAn), which we call ring-shift isomerization. Among the Y zeolites and mordenites tested, a proton-form mordenite (HML8) with relatively lower SiO2/Al2O3 ratio afforded a higher yield of sym-OHAn with a higher sym-OHAn/sym-OHP ratio. The best selectivities towards sym-OHAn with HML8 at 250°C are 89-91% at 58-59% conversion of sym-OHP in decalin and in mesitylene solvents. The second is the conversion of cis-decahydronaphthalene (cis-DeHN) to trans-DeHN, which may be called conformational isomerization. For this reaction, a La ion-exchanged Y zeolite (LaHY) displayed the best selectivity with a trans-DeHN/cis-DeHN ratio of over 10 at 250°C.

AB - This paper reports on two zeolite-catalyzed isomerization reactions of polycyclic hydrocarbons. The first is the transformation of 1,2,3,4,5,6,7,8-octahydrophenanthrene (sym-OHP) to 1,2,3,4,5,6,7,8-octahydroanthracene (sym-OHAn), which we call ring-shift isomerization. Among the Y zeolites and mordenites tested, a proton-form mordenite (HML8) with relatively lower SiO2/Al2O3 ratio afforded a higher yield of sym-OHAn with a higher sym-OHAn/sym-OHP ratio. The best selectivities towards sym-OHAn with HML8 at 250°C are 89-91% at 58-59% conversion of sym-OHP in decalin and in mesitylene solvents. The second is the conversion of cis-decahydronaphthalene (cis-DeHN) to trans-DeHN, which may be called conformational isomerization. For this reaction, a La ion-exchanged Y zeolite (LaHY) displayed the best selectivity with a trans-DeHN/cis-DeHN ratio of over 10 at 250°C.

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Zeolite-catalyzed ring-shift isomerization of sym-octahydrophenanthrene and conformational isomerization of cis-decahydronaphthalene

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