Production of p-cymene from crude sulphate turpentine with commercial zeolite catalyst using a continuous fixed bed reactor

Juha Linnekoski (Corresponding Author), Martta Asikainan, Harri Heikkinen, Reetta Kaila, Jari Räsänen, Antero Laitinen, Ali Harlin

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

9 Citations (Scopus)

Abstract

Crude sulphate turpentine (CST), containing α-pinene, 3-carene, other terpene isomers, and organic sulphur compounds, was used as feedstock in the production of cymenes with commercial zeolite catalysts. The catalysts used were not sensitive to sulphur, and the desulphurisation step was not needed prior to cymene synthesis. The experiments were performed in a continuous fixed bed reactor. Promising results were obtained after initial optimization at temperatures close to 300 °C with faujasite Y zeolite under 5 bar N2 pressure. Cymenes were produced with 54% yields from model compound α-pinene and with 28% yields from CST. The mechanistic route of the reaction can be divided into three steps: (1) ring opening, (2) rearrangement, and (3) dehydrogenation. The final step in the formation of p-cymene can occur via dehydrogenation or disproportion; here the effect of reaction conditions and catalyst plays a crucial role.
Original languageEnglish
Pages (from-to)1468-1475
JournalOrganic Process Research and Development
Volume18
Issue number11
DOIs
Publication statusPublished - 2014
MoE publication typeA1 Journal article-refereed

Fingerprint

turpentine
Turpentine
Zeolites
Sulfates
beds
sulfates
reactors
Dehydrogenation
dehydrogenation
catalysts
Catalysts
organic sulfur compounds
terpenes
Sulfur Compounds
Terpenes
Sulfur
Isomers
Feedstocks
sulfur
isomers

Keywords

  • turpentine
  • catalysts
  • chemical reactors
  • dehydrogenation
  • isomers
  • monoterpenes
  • sulfur
  • chemical synthesis
  • commercial zeolite
  • faujasites
  • fixed bed reactor
  • initial optimization
  • model compound
  • reaction conditions
  • ring opening
  • Y zeolites

Cite this

Linnekoski, Juha ; Asikainan, Martta ; Heikkinen, Harri ; Kaila, Reetta ; Räsänen, Jari ; Laitinen, Antero ; Harlin, Ali. / Production of p-cymene from crude sulphate turpentine with commercial zeolite catalyst using a continuous fixed bed reactor. In: Organic Process Research and Development. 2014 ; Vol. 18, No. 11. pp. 1468-1475.
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title = "Production of p-cymene from crude sulphate turpentine with commercial zeolite catalyst using a continuous fixed bed reactor",
abstract = "Crude sulphate turpentine (CST), containing α-pinene, 3-carene, other terpene isomers, and organic sulphur compounds, was used as feedstock in the production of cymenes with commercial zeolite catalysts. The catalysts used were not sensitive to sulphur, and the desulphurisation step was not needed prior to cymene synthesis. The experiments were performed in a continuous fixed bed reactor. Promising results were obtained after initial optimization at temperatures close to 300 °C with faujasite Y zeolite under 5 bar N2 pressure. Cymenes were produced with 54{\%} yields from model compound α-pinene and with 28{\%} yields from CST. The mechanistic route of the reaction can be divided into three steps: (1) ring opening, (2) rearrangement, and (3) dehydrogenation. The final step in the formation of p-cymene can occur via dehydrogenation or disproportion; here the effect of reaction conditions and catalyst plays a crucial role.",
keywords = "turpentine, catalysts, chemical reactors, dehydrogenation, isomers, monoterpenes, sulfur, chemical synthesis, commercial zeolite, faujasites, fixed bed reactor, initial optimization, model compound, reaction conditions, ring opening, Y zeolites",
author = "Juha Linnekoski and Martta Asikainan and Harri Heikkinen and Reetta Kaila and Jari R{\"a}s{\"a}nen and Antero Laitinen and Ali Harlin",
year = "2014",
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language = "English",
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Linnekoski, J, Asikainan, M, Heikkinen, H, Kaila, R, Räsänen, J, Laitinen, A & Harlin, A 2014, 'Production of p-cymene from crude sulphate turpentine with commercial zeolite catalyst using a continuous fixed bed reactor', Organic Process Research and Development, vol. 18, no. 11, pp. 1468-1475. https://doi.org/10.1021/op500160f

Production of p-cymene from crude sulphate turpentine with commercial zeolite catalyst using a continuous fixed bed reactor. / Linnekoski, Juha (Corresponding Author); Asikainan, Martta; Heikkinen, Harri; Kaila, Reetta; Räsänen, Jari; Laitinen, Antero; Harlin, Ali.

In: Organic Process Research and Development, Vol. 18, No. 11, 2014, p. 1468-1475.

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

TY - JOUR

T1 - Production of p-cymene from crude sulphate turpentine with commercial zeolite catalyst using a continuous fixed bed reactor

AU - Linnekoski, Juha

AU - Asikainan, Martta

AU - Heikkinen, Harri

AU - Kaila, Reetta

AU - Räsänen, Jari

AU - Laitinen, Antero

AU - Harlin, Ali

PY - 2014

Y1 - 2014

N2 - Crude sulphate turpentine (CST), containing α-pinene, 3-carene, other terpene isomers, and organic sulphur compounds, was used as feedstock in the production of cymenes with commercial zeolite catalysts. The catalysts used were not sensitive to sulphur, and the desulphurisation step was not needed prior to cymene synthesis. The experiments were performed in a continuous fixed bed reactor. Promising results were obtained after initial optimization at temperatures close to 300 °C with faujasite Y zeolite under 5 bar N2 pressure. Cymenes were produced with 54% yields from model compound α-pinene and with 28% yields from CST. The mechanistic route of the reaction can be divided into three steps: (1) ring opening, (2) rearrangement, and (3) dehydrogenation. The final step in the formation of p-cymene can occur via dehydrogenation or disproportion; here the effect of reaction conditions and catalyst plays a crucial role.

AB - Crude sulphate turpentine (CST), containing α-pinene, 3-carene, other terpene isomers, and organic sulphur compounds, was used as feedstock in the production of cymenes with commercial zeolite catalysts. The catalysts used were not sensitive to sulphur, and the desulphurisation step was not needed prior to cymene synthesis. The experiments were performed in a continuous fixed bed reactor. Promising results were obtained after initial optimization at temperatures close to 300 °C with faujasite Y zeolite under 5 bar N2 pressure. Cymenes were produced with 54% yields from model compound α-pinene and with 28% yields from CST. The mechanistic route of the reaction can be divided into three steps: (1) ring opening, (2) rearrangement, and (3) dehydrogenation. The final step in the formation of p-cymene can occur via dehydrogenation or disproportion; here the effect of reaction conditions and catalyst plays a crucial role.

KW - turpentine

KW - catalysts

KW - chemical reactors

KW - dehydrogenation

KW - isomers

KW - monoterpenes

KW - sulfur

KW - chemical synthesis

KW - commercial zeolite

KW - faujasites

KW - fixed bed reactor

KW - initial optimization

KW - model compound

KW - reaction conditions

KW - ring opening

KW - Y zeolites

U2 - 10.1021/op500160f

DO - 10.1021/op500160f

M3 - Article

VL - 18

SP - 1468

EP - 1475

JO - Organic Process Research and Development

JF - Organic Process Research and Development

SN - 1083-6160

IS - 11

ER -

Linnekoski J, Asikainan M, Heikkinen H, Kaila R, Räsänen J, Laitinen A et al. Production of p-cymene from crude sulphate turpentine with commercial zeolite catalyst using a continuous fixed bed reactor. Organic Process Research and Development. 2014;18(11):1468-1475. https://doi.org/10.1021/op500160f

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