Synthesis of p-Xylene by Dehydroaromatization of 3-Methyleneheptane obtained from Ethylene

Alan Goldman (Inventor), Andrew Steffens (Inventor), William Schinski (Inventor)

Research output: Innovation

Abstract



Invention Summary:

p -Xylene is mostly produced from cracking of naphtha, but there is a need for new and cost-effective methods for the production.  Indeed, conventional p-xylene synthesis requires toluene separation from refinery gasoline streams; performing a disproportionation reaction to yield a benzene fraction and a mixed xylene fraction; and finally an isomerization step over a zeolite catalyst which converts ortho- and meta- xylenes to the para isomer. p -Xylene is then separated in a costly crystallization step from the unconverted ortho and meta isomers which are recycled to the zeolite.

Rutgers scientists have developed a new method of preparing p-xylene by dehydroaromatization of 3-methyleneheptane (i.e. 2-ethylhex-1-ene) or 3-methylheptane using pincer-ligated iridium catalysts under relatively mild conditions and with yields of up to 60%. 3-Methyleneheptane can be obtained from the dimerization of butenes.Butenes can in turn can be obtained as refinery products or from the dimerization of ethylene.

Market Applications:

  • Petrochemicals
  • Catalysts

Advantages:

  • Relatively mild reaction conditions
  • Good yields
  • Ethylene or butene refinery products as feedstock
  • The proposed method is more cost-effective than current methods

Intellectual Property & Development Status:

Patent pending. This product is available for licensing and/or research collaboration.

Original languageEnglish (US)
StatePublished - Dec 2017

Fingerprint

Zeolites
Dimerization
Isomers
Catalysts
Iridium
Xylenes
Intellectual property
Toluene
Patents and inventions
Isomerization
Crystallization
Benzene
Petrochemicals
Feedstocks
Gasoline
Costs
ethylene
4-xylene
butylene
3-xylene

Cite this

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title = "Synthesis of p-Xylene by Dehydroaromatization of 3-Methyleneheptane obtained from Ethylene",
abstract = "Invention Summary: p -Xylene is mostly produced from cracking of naphtha, but there is a need for new and cost-effective methods for the production.  Indeed, conventional p-xylene synthesis requires toluene separation from refinery gasoline streams; performing a disproportionation reaction to yield a benzene fraction and a mixed xylene fraction; and finally an isomerization step over a zeolite catalyst which converts ortho- and meta- xylenes to the para isomer. p -Xylene is then separated in a costly crystallization step from the unconverted ortho and meta isomers which are recycled to the zeolite. Rutgers scientists have developed a new method of preparing p-xylene by dehydroaromatization of 3-methyleneheptane (i.e. 2-ethylhex-1-ene) or 3-methylheptane using pincer-ligated iridium catalysts under relatively mild conditions and with yields of up to 60{\%}. 3-Methyleneheptane can be obtained from the dimerization of butenes.Butenes can in turn can be obtained as refinery products or from the dimerization of ethylene. Market Applications: Petrochemicals Catalysts Advantages: Relatively mild reaction conditions Good yields Ethylene or butene refinery products as feedstock The proposed method is more cost-effective than current methods Intellectual Property & Development Status: Patent pending. This product is available for licensing and/or research collaboration.",
author = "Alan Goldman and Andrew Steffens and William Schinski",
year = "2017",
month = "12",
language = "English (US)",
type = "Patent",

}

Synthesis of p-Xylene by Dehydroaromatization of 3-Methyleneheptane obtained from Ethylene. / Goldman, Alan (Inventor); Steffens, Andrew (Inventor); Schinski, William (Inventor).

Research output: Innovation

TY - PAT

T1 - Synthesis of p-Xylene by Dehydroaromatization of 3-Methyleneheptane obtained from Ethylene

AU - Goldman, Alan

AU - Steffens, Andrew

AU - Schinski, William

PY - 2017/12

Y1 - 2017/12

N2 - Invention Summary: p -Xylene is mostly produced from cracking of naphtha, but there is a need for new and cost-effective methods for the production.  Indeed, conventional p-xylene synthesis requires toluene separation from refinery gasoline streams; performing a disproportionation reaction to yield a benzene fraction and a mixed xylene fraction; and finally an isomerization step over a zeolite catalyst which converts ortho- and meta- xylenes to the para isomer. p -Xylene is then separated in a costly crystallization step from the unconverted ortho and meta isomers which are recycled to the zeolite. Rutgers scientists have developed a new method of preparing p-xylene by dehydroaromatization of 3-methyleneheptane (i.e. 2-ethylhex-1-ene) or 3-methylheptane using pincer-ligated iridium catalysts under relatively mild conditions and with yields of up to 60%. 3-Methyleneheptane can be obtained from the dimerization of butenes.Butenes can in turn can be obtained as refinery products or from the dimerization of ethylene. Market Applications: Petrochemicals Catalysts Advantages: Relatively mild reaction conditions Good yields Ethylene or butene refinery products as feedstock The proposed method is more cost-effective than current methods Intellectual Property & Development Status: Patent pending. This product is available for licensing and/or research collaboration.

AB - Invention Summary: p -Xylene is mostly produced from cracking of naphtha, but there is a need for new and cost-effective methods for the production.  Indeed, conventional p-xylene synthesis requires toluene separation from refinery gasoline streams; performing a disproportionation reaction to yield a benzene fraction and a mixed xylene fraction; and finally an isomerization step over a zeolite catalyst which converts ortho- and meta- xylenes to the para isomer. p -Xylene is then separated in a costly crystallization step from the unconverted ortho and meta isomers which are recycled to the zeolite. Rutgers scientists have developed a new method of preparing p-xylene by dehydroaromatization of 3-methyleneheptane (i.e. 2-ethylhex-1-ene) or 3-methylheptane using pincer-ligated iridium catalysts under relatively mild conditions and with yields of up to 60%. 3-Methyleneheptane can be obtained from the dimerization of butenes.Butenes can in turn can be obtained as refinery products or from the dimerization of ethylene. Market Applications: Petrochemicals Catalysts Advantages: Relatively mild reaction conditions Good yields Ethylene or butene refinery products as feedstock The proposed method is more cost-effective than current methods Intellectual Property & Development Status: Patent pending. This product is available for licensing and/or research collaboration.

UR - http://rutgers.technologypublisher.com/tech/Synthesis_of_p-Xylene_by_Dehydroaromatization_of_3-Methyleneheptane_obtained_from_Ethylene

M3 - Innovation

ER -