Shape-selective methylation of 2-methynaphthalene to 2,6-dimethylnaphthalene over modified HZSM-5 zeolite catalysts

Chen Zhang, Xinwen Guo, Chunshan Song

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

Shape-selective alkylation of polycyclic hydrocarbons has been the focus of many recent studies1-5 for preparation of symmetric intermediates such as 2,6-dialkylnaphthalene (2,6-DAN) which are used for synthesizing advanced polymer materials. Among 2,6-DANs, 2,6-dimethylnaphthalene (DMN) is regarded as the most suitable desirable intermediate with which can be oxidized with high selectivity reactivity in process of oxidation into 2,6-naphthalenedicarboxylic acid (2,6-NDCA), a monomor for aromatic polyester materials.Therefore, effective synthesis of 2,6-DMN has been become an important subjectstudied extensively.In this work, we compared the effects of potassium and phosphorus modification on the selectivity and activity of ZSM-5 for the methylation of 2-MN with methnol, and identified the promising direction for modification towards increasing the ratio of 2,6/2,7-DMN. Furthermore, we aimed to clarify the reason why the modified HZSM-5 zeolites exhibit higher selectivity for the methylation of 2-MN.Over KZSM-5(1.0), selectivity of DMN and 2,6-DMN were 72.8% and 54.1% respectively. Especially, at 6th hr of TOS, the selectivity to 2,6-DMN reached to 58%. The yield of 2,6-DMN was around 9.0% which is one of the best results as we know according to the literature.P and K modification showed totally opposite impact on ratio of 2,6/2,7-DMN for different effct on the acid properties of HZSM-5.

Original languageEnglish (US)
Title of host publicationAmerican Chemical Society - 238th National Meeting and Exposition, ACS 2009, Abstracts of Scientific Papers
StatePublished - 2009
Event238th National Meeting and Exposition of the American Chemical Society, ACS 2009 - Washington, DC, United States
Duration: Aug 16 2009Aug 20 2009

Other

Other238th National Meeting and Exposition of the American Chemical Society, ACS 2009
CountryUnited States
CityWashington, DC
Period8/16/098/20/09

Fingerprint

Zeolites
Methylation
Catalysts
Acids
Alkylation
Potassium
Phosphorus
Polyesters
Hydrocarbons
Cyclic Hydrocarbons
Oxidation
Polymers
2,6-dimethylnaphthalene

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Zhang, C., Guo, X., & Song, C. (2009). Shape-selective methylation of 2-methynaphthalene to 2,6-dimethylnaphthalene over modified HZSM-5 zeolite catalysts. In American Chemical Society - 238th National Meeting and Exposition, ACS 2009, Abstracts of Scientific Papers
Zhang, Chen ; Guo, Xinwen ; Song, Chunshan. / Shape-selective methylation of 2-methynaphthalene to 2,6-dimethylnaphthalene over modified HZSM-5 zeolite catalysts. American Chemical Society - 238th National Meeting and Exposition, ACS 2009, Abstracts of Scientific Papers. 2009.
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title = "Shape-selective methylation of 2-methynaphthalene to 2,6-dimethylnaphthalene over modified HZSM-5 zeolite catalysts",
abstract = "Shape-selective alkylation of polycyclic hydrocarbons has been the focus of many recent studies1-5 for preparation of symmetric intermediates such as 2,6-dialkylnaphthalene (2,6-DAN) which are used for synthesizing advanced polymer materials. Among 2,6-DANs, 2,6-dimethylnaphthalene (DMN) is regarded as the most suitable desirable intermediate with which can be oxidized with high selectivity reactivity in process of oxidation into 2,6-naphthalenedicarboxylic acid (2,6-NDCA), a monomor for aromatic polyester materials.Therefore, effective synthesis of 2,6-DMN has been become an important subjectstudied extensively.In this work, we compared the effects of potassium and phosphorus modification on the selectivity and activity of ZSM-5 for the methylation of 2-MN with methnol, and identified the promising direction for modification towards increasing the ratio of 2,6/2,7-DMN. Furthermore, we aimed to clarify the reason why the modified HZSM-5 zeolites exhibit higher selectivity for the methylation of 2-MN.Over KZSM-5(1.0), selectivity of DMN and 2,6-DMN were 72.8{\%} and 54.1{\%} respectively. Especially, at 6th hr of TOS, the selectivity to 2,6-DMN reached to 58{\%}. The yield of 2,6-DMN was around 9.0{\%} which is one of the best results as we know according to the literature.P and K modification showed totally opposite impact on ratio of 2,6/2,7-DMN for different effct on the acid properties of HZSM-5.",
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Zhang, C, Guo, X & Song, C 2009, Shape-selective methylation of 2-methynaphthalene to 2,6-dimethylnaphthalene over modified HZSM-5 zeolite catalysts. in American Chemical Society - 238th National Meeting and Exposition, ACS 2009, Abstracts of Scientific Papers. 238th National Meeting and Exposition of the American Chemical Society, ACS 2009, Washington, DC, United States, 8/16/09.

Shape-selective methylation of 2-methynaphthalene to 2,6-dimethylnaphthalene over modified HZSM-5 zeolite catalysts. / Zhang, Chen; Guo, Xinwen; Song, Chunshan.

American Chemical Society - 238th National Meeting and Exposition, ACS 2009, Abstracts of Scientific Papers. 2009.

Research output: Chapter in Book/Report/Conference proceedingConference contribution

TY - GEN

T1 - Shape-selective methylation of 2-methynaphthalene to 2,6-dimethylnaphthalene over modified HZSM-5 zeolite catalysts

AU - Zhang, Chen

AU - Guo, Xinwen

AU - Song, Chunshan

PY - 2009

Y1 - 2009

N2 - Shape-selective alkylation of polycyclic hydrocarbons has been the focus of many recent studies1-5 for preparation of symmetric intermediates such as 2,6-dialkylnaphthalene (2,6-DAN) which are used for synthesizing advanced polymer materials. Among 2,6-DANs, 2,6-dimethylnaphthalene (DMN) is regarded as the most suitable desirable intermediate with which can be oxidized with high selectivity reactivity in process of oxidation into 2,6-naphthalenedicarboxylic acid (2,6-NDCA), a monomor for aromatic polyester materials.Therefore, effective synthesis of 2,6-DMN has been become an important subjectstudied extensively.In this work, we compared the effects of potassium and phosphorus modification on the selectivity and activity of ZSM-5 for the methylation of 2-MN with methnol, and identified the promising direction for modification towards increasing the ratio of 2,6/2,7-DMN. Furthermore, we aimed to clarify the reason why the modified HZSM-5 zeolites exhibit higher selectivity for the methylation of 2-MN.Over KZSM-5(1.0), selectivity of DMN and 2,6-DMN were 72.8% and 54.1% respectively. Especially, at 6th hr of TOS, the selectivity to 2,6-DMN reached to 58%. The yield of 2,6-DMN was around 9.0% which is one of the best results as we know according to the literature.P and K modification showed totally opposite impact on ratio of 2,6/2,7-DMN for different effct on the acid properties of HZSM-5.

AB - Shape-selective alkylation of polycyclic hydrocarbons has been the focus of many recent studies1-5 for preparation of symmetric intermediates such as 2,6-dialkylnaphthalene (2,6-DAN) which are used for synthesizing advanced polymer materials. Among 2,6-DANs, 2,6-dimethylnaphthalene (DMN) is regarded as the most suitable desirable intermediate with which can be oxidized with high selectivity reactivity in process of oxidation into 2,6-naphthalenedicarboxylic acid (2,6-NDCA), a monomor for aromatic polyester materials.Therefore, effective synthesis of 2,6-DMN has been become an important subjectstudied extensively.In this work, we compared the effects of potassium and phosphorus modification on the selectivity and activity of ZSM-5 for the methylation of 2-MN with methnol, and identified the promising direction for modification towards increasing the ratio of 2,6/2,7-DMN. Furthermore, we aimed to clarify the reason why the modified HZSM-5 zeolites exhibit higher selectivity for the methylation of 2-MN.Over KZSM-5(1.0), selectivity of DMN and 2,6-DMN were 72.8% and 54.1% respectively. Especially, at 6th hr of TOS, the selectivity to 2,6-DMN reached to 58%. The yield of 2,6-DMN was around 9.0% which is one of the best results as we know according to the literature.P and K modification showed totally opposite impact on ratio of 2,6/2,7-DMN for different effct on the acid properties of HZSM-5.

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M3 - Conference contribution

SN - 9780841200050

BT - American Chemical Society - 238th National Meeting and Exposition, ACS 2009, Abstracts of Scientific Papers

ER -

Zhang C, Guo X, Song C. Shape-selective methylation of 2-methynaphthalene to 2,6-dimethylnaphthalene over modified HZSM-5 zeolite catalysts. In American Chemical Society - 238th National Meeting and Exposition, ACS 2009, Abstracts of Scientific Papers. 2009