Squalane and isosqualane compositions and methods for preparing the same

Fisher, Karl; Schofer, Susan Jessica; Kanne, David B

Title: Squalane and isosqualane compositions and methods for preparing the same

Abstract

Provided herein are methods comprising catalytic dimerization of .beta.-farnesene to obtain squalane and/or isosqualane. Compositions comprising squalane and/or isosqualane are provided. In certain embodiments, squalane and isosqualane prepared by the methods provided herein can be useful for applications in cosmetic industry and/or in the lubricants industry.

Inventors:: Fisher, Karl; Schofer, Susan Jessica; Kanne, David B

Issue Date:: 2013-11-19

Research Org.:: Amyris, Inc. (Emeryville, CA)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1108726

Patent Number(s):: 8586814

Application Number:: 13/112,991

Assignee:: Amyris, Inc. (Emeryville, CA)

Patent Classifications (CPCs):: C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10M - LUBRICATING COMPOSITIONS

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

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C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10M - LUBRICATING COMPOSITIONS
C10M2209/084 - Acrylate

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C2531/38 - of titanium, zirconium or hafnium
C07C5/09 - to carbon-to-carbon double bonds

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10N - INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
C10N2040/25 - Internal combustion engines

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10M - LUBRICATING COMPOSITIONS
C10M2205/028 - containing aliphatic monomers having more than four carbon atoms

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C2531/30 - Halides
C07C9/22 - with more than fifteen carbon atoms

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10N - INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
C10N2040/30 - Refrigerator lubricant

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10M - LUBRICATING COMPOSITIONS
C10M2207/282 - of
C10M105/04 - aliphatic

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10N - INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
C10N2040/04 - Oil-bath

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C11/21 - Alkatrienes

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10M - LUBRICATING COMPOSITIONS
C10M2203/0206 - used as base material

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C2/403 - {Catalytic processes}

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10N - INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
C10N2040/08 - Hydraulic fluids, e.g. brake-fluids

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C2531/28 - of the platinum group metals, iron group metals or copper

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10N - INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
C10N2040/20 - Metal working
C10N2030/02 - Pour-point

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DOE Contract Number:: EE0002869

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Fisher, Karl, Schofer, Susan Jessica, and Kanne, David B. Squalane and isosqualane compositions and methods for preparing the same.  United States: N. p., 2013. 
        Web.

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                    Fisher, Karl, Schofer, Susan Jessica, & Kanne, David B. Squalane and isosqualane compositions and methods for preparing the same.  United States.

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                    Fisher, Karl, Schofer, Susan Jessica, and Kanne, David B. Tue .  
        "Squalane and isosqualane compositions and methods for preparing the same".  United States.  https://www.osti.gov/servlets/purl/1108726.

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@article{osti_1108726,

  title        = {Squalane and isosqualane compositions and methods for preparing the same},

  author       = {Fisher, Karl and Schofer, Susan Jessica and Kanne, David B},

  abstractNote = {Provided herein are methods comprising catalytic dimerization of .beta.-farnesene to obtain squalane and/or isosqualane. Compositions comprising squalane and/or isosqualane are provided. In certain embodiments, squalane and isosqualane prepared by the methods provided herein can be useful for applications in cosmetic industry and/or in the lubricants industry.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2013},

  month        = {11}

}

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Works referenced in this record:

Metal-Assisted Terpenoid Synthesis. V. The Catalytic Trimerization of Isoprene to trans -β-Farnesene and Its Synthetic Applications for Terpenoids
journal, April 1978

Akutagawa, Susumu; Taketomi, Takanao; Kumobayashi, Hidenori
Bulletin of the Chemical Society of Japan, Vol. 51, Issue 4
https://doi.org/10.1246/bcsj.51.1158

Codimerization of C6-C10 ?-olefins with butadiene using zirconium complexes
journal, June 1981

Vostrikova, O. S.; Ibragimov, A. G.; Tolstikov, G. A.
Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 30, Issue 6
https://doi.org/10.1007/BF00950315

Zur Telomerisierung von Isopren mit Palladium-Komplexen bei niedriger Temperatur
journal, January 1985

Berger, R.; Gaube, W.
Journal f�r Praktische Chemie, Vol. 327, Issue 4
https://doi.org/10.1002/prac.19853270415

Linear dimerization and codimerization of substituted 1,3-dienes catalyzed by zirconium complexes
journal, September 1979

Dzhemilev, U. M.; Ibragimov, A. G.; Vostrikova, O. S.
Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 28, Issue 9
https://doi.org/10.1007/BF00952475

Synthesis and structure of zirconium tetrachloride ester complexes, ethylene oligomerization catalyst precursors
journal, August 1989

Young, David A.
Journal of Molecular Catalysis, Vol. 53, Issue 3
https://doi.org/10.1016/0304-5102(89)80074-4

Squalene–hopene cyclase: insight into the role of the methyl group on the squalene backbone upon the polycyclization cascade. Enzymatic cyclization products of squalene analogs lacking a 26-methyl group and possessing a methyl group at C(7) or C(11)
journal, January 2004

Nakano, Shin-ichi; Ohashi, Shumi; Hoshino, Tsutomu
Org. Biomol. Chem., Vol. 2, Issue 14
https://doi.org/10.1039/B404287E

Metal-Assisted Terpenoid Synthesis ii. Catalytic Conversion of Isoprene into Farnesene and its Isomer, 2,6-Dimethyl-10-Methylene-1,6-Trans,11-Dodecatriene
journal, May 1976

Akutagawa, Susumu; Taketomi, Takanao; Otsuka, Sei
Chemistry Letters, Vol. 5, Issue 5
https://doi.org/10.1246/cl.1976.485

Die Synthese des Isosqualens
journal, May 1955

Mondon, Albert
Chemische Berichte, Vol. 88, Issue 5
https://doi.org/10.1002/cber.19550880522

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Similar Records

Title: Squalane and isosqualane compositions and methods for preparing the same

Abstract

Citation Formats

Metal-Assisted Terpenoid Synthesis. V. The Catalytic Trimerization of Isoprene to trans -β-Farnesene and Its Synthetic Applications for Terpenoids journal, April 1978

Codimerization of C6-C10 ?-olefins with butadiene using zirconium complexes journal, June 1981

Zur Telomerisierung von Isopren mit Palladium-Komplexen bei niedriger Temperatur journal, January 1985

Linear dimerization and codimerization of substituted 1,3-dienes catalyzed by zirconium complexes journal, September 1979

Synthesis and structure of zirconium tetrachloride ester complexes, ethylene oligomerization catalyst precursors journal, August 1989

Squalene–hopene cyclase: insight into the role of the methyl group on the squalene backbone upon the polycyclization cascade. Enzymatic cyclization products of squalene analogs lacking a 26-methyl group and possessing a methyl group at C(7) or C(11) journal, January 2004

Metal-Assisted Terpenoid Synthesis ii. Catalytic Conversion of Isoprene into Farnesene and its Isomer, 2,6-Dimethyl-10-Methylene-1,6-Trans,11-Dodecatriene journal, May 1976

Die Synthese des Isosqualens journal, May 1955

Metal-Assisted Terpenoid Synthesis. V. The Catalytic Trimerization of Isoprene to trans -β-Farnesene and Its Synthetic Applications for Terpenoids
journal, April 1978

Codimerization of C6-C10 ?-olefins with butadiene using zirconium complexes
journal, June 1981

Zur Telomerisierung von Isopren mit Palladium-Komplexen bei niedriger Temperatur
journal, January 1985

Linear dimerization and codimerization of substituted 1,3-dienes catalyzed by zirconium complexes
journal, September 1979

Synthesis and structure of zirconium tetrachloride ester complexes, ethylene oligomerization catalyst precursors
journal, August 1989

Squalene–hopene cyclase: insight into the role of the methyl group on the squalene backbone upon the polycyclization cascade. Enzymatic cyclization products of squalene analogs lacking a 26-methyl group and possessing a methyl group at C(7) or C(11)
journal, January 2004

Metal-Assisted Terpenoid Synthesis ii. Catalytic Conversion of Isoprene into Farnesene and its Isomer, 2,6-Dimethyl-10-Methylene-1,6-Trans,11-Dodecatriene
journal, May 1976

Die Synthese des Isosqualens
journal, May 1955