Renewable linear alpha olefins by selective ethenolysis of decarboxylated fatty acids

Research output: Contribution to journalArticleAcademicpeer-review

22 Citations (Scopus)

Abstract

A two-step concept for the production of linear alpha olefins from biomass is reported. As a starting material an internally unsaturated C17 alkene was used, which was obtained by the decarboxylation of oleic acid. Here, we report on the ethenolysis of this bio-based product, using commercially available metathesis catalysts. The desired alpha olefin products, 1-nonene and 1-decene, were obtained in excellent yield (96%) and selectivity (96%). Practical applications: The two-step conversion described in this contribution, starting from unsaturated fatty acids, provides a method for the production of industrially important linear alpha olefins. These valuable products are widely used as starting materials for the production of surfactants and polymers such as linear low density polyethylene (LLDPE).
LanguageEnglish
Pages911-918
JournalEuropean Journal of Lipid Science and Technology
Volume114
Issue number8
DOIs
Publication statusPublished - 2012

Fingerprint

alkenes
Alkenes
Fatty acids
Olefins
Fatty Acids
fatty acids
olefin
biobased products
decarboxylation
Unsaturated fatty acids
catalysts
unsaturated fatty acids
surfactants
polyethylene
Linear low density polyethylenes
Decarboxylation
oleic acid
Oleic acid
polymers
Polyethylene

Keywords

  • productive catalyst turnovers
  • metathesis catalysts
  • cross-metathesis
  • methyl oleate
  • natural oils
  • dimethyl carbonate
  • high conversion
  • diesel fuel
  • deoxygenation
  • feedstocks

Cite this

@article{64a1bf1512f84d42a776a48d5ded8eda,
title = "Renewable linear alpha olefins by selective ethenolysis of decarboxylated fatty acids",
abstract = "A two-step concept for the production of linear alpha olefins from biomass is reported. As a starting material an internally unsaturated C17 alkene was used, which was obtained by the decarboxylation of oleic acid. Here, we report on the ethenolysis of this bio-based product, using commercially available metathesis catalysts. The desired alpha olefin products, 1-nonene and 1-decene, were obtained in excellent yield (96{\%}) and selectivity (96{\%}). Practical applications: The two-step conversion described in this contribution, starting from unsaturated fatty acids, provides a method for the production of industrially important linear alpha olefins. These valuable products are widely used as starting materials for the production of surfactants and polymers such as linear low density polyethylene (LLDPE).",
keywords = "productive catalyst turnovers, metathesis catalysts, cross-metathesis, methyl oleate, natural oils, dimethyl carbonate, high conversion, diesel fuel, deoxygenation, feedstocks",
author = "{van der Klis}, F. and {le Notre}, J.E.L. and R. Blaauw and {van Haveren}, J. and {van Es}, D.S.",
year = "2012",
doi = "10.1002/ejlt.201200024",
language = "English",
volume = "114",
pages = "911--918",
journal = "European Journal of Lipid Science and Technology",
issn = "1438-7697",
publisher = "Wiley-VCH Verlag",
number = "8",

}

Renewable linear alpha olefins by selective ethenolysis of decarboxylated fatty acids. / van der Klis, F.; le Notre, J.E.L.; Blaauw, R.; van Haveren, J.; van Es, D.S.

In: European Journal of Lipid Science and Technology, Vol. 114, No. 8, 2012, p. 911-918.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Renewable linear alpha olefins by selective ethenolysis of decarboxylated fatty acids

AU - van der Klis, F.

AU - le Notre, J.E.L.

AU - Blaauw, R.

AU - van Haveren, J.

AU - van Es, D.S.

PY - 2012

Y1 - 2012

N2 - A two-step concept for the production of linear alpha olefins from biomass is reported. As a starting material an internally unsaturated C17 alkene was used, which was obtained by the decarboxylation of oleic acid. Here, we report on the ethenolysis of this bio-based product, using commercially available metathesis catalysts. The desired alpha olefin products, 1-nonene and 1-decene, were obtained in excellent yield (96%) and selectivity (96%). Practical applications: The two-step conversion described in this contribution, starting from unsaturated fatty acids, provides a method for the production of industrially important linear alpha olefins. These valuable products are widely used as starting materials for the production of surfactants and polymers such as linear low density polyethylene (LLDPE).

AB - A two-step concept for the production of linear alpha olefins from biomass is reported. As a starting material an internally unsaturated C17 alkene was used, which was obtained by the decarboxylation of oleic acid. Here, we report on the ethenolysis of this bio-based product, using commercially available metathesis catalysts. The desired alpha olefin products, 1-nonene and 1-decene, were obtained in excellent yield (96%) and selectivity (96%). Practical applications: The two-step conversion described in this contribution, starting from unsaturated fatty acids, provides a method for the production of industrially important linear alpha olefins. These valuable products are widely used as starting materials for the production of surfactants and polymers such as linear low density polyethylene (LLDPE).

KW - productive catalyst turnovers

KW - metathesis catalysts

KW - cross-metathesis

KW - methyl oleate

KW - natural oils

KW - dimethyl carbonate

KW - high conversion

KW - diesel fuel

KW - deoxygenation

KW - feedstocks

U2 - 10.1002/ejlt.201200024

DO - 10.1002/ejlt.201200024

M3 - Article

VL - 114

SP - 911

EP - 918

JO - European Journal of Lipid Science and Technology

T2 - European Journal of Lipid Science and Technology

JF - European Journal of Lipid Science and Technology

SN - 1438-7697

IS - 8

ER -