Butyl oleate explained

Butyl oleate is a fatty acid ester and an organic chemical found in liquid form. It has the formula C22H42O2 and the CAS Registry Number 142-77-8.[1] It is REACH registered and produced or imported into the European Union with the EC number of 205-559-6.

Synthesis and reactions

It is formed by the condensation of oleic acid and butanol often using an enzyme as catalyst or other biobased catalysts.[2] [3] [4] Ionic liquids may also be used as the catalyst.[5] It undergoes the Bouveault–Blanc reduction with oleyl alcohol and butanol as the products.[6]

Alternative names

It is also known as Butyl cis-9-octadecenoate, Oleic acid butyl ester, butyl 9-octadecenoate and 1-butyl oleate. The IUPAC name is butyl (Z)-octadec-9-enoate.[7]

Uses

It has approval for use as a food additive in Europe[8] and also the US by the FDA.[9] Various other uses include as a lubricant and lubricant additive,[10] paints and coatings additive, and as a plasticizer especially for PVC.[11] [12] Similar to other fatty acid esters, it has found use in biodiesel and as a fuel additive.[13]

See also

References

  1. Web site: CAS Common Chemistry . 2023-11-10 . commonchemistry.cas.org.
  2. Orrego . Carlos Eduardo . Valencia . Jesús Sigifredo . Zapata . Catalina . 2009-05-01 . Candida rugosa Lipase Supported on High Crystallinity Chitosan as Biocatalyst for the Synthesis of 1-Butyl Oleate . Catalysis Letters . en . 129 . 3 . 312–322 . 10.1007/s10562-009-9857-6 . 86759909 . 1572-879X.
  3. Book: Linko . Y.-Y. . Progress in Biotechnology . Factors Affecting Lipase Catalyzed n-Butyl Oleate Synthesis . 1992-01-01 . 8 . 601–608 . Tramper . J. . Biocatalysis in Non-Conventional Media . Elsevier . 10.1016/b978-0-444-89046-7.50087-4 . Rantanen . O. . Yu . H. -C. . Linko . P. . 9780444890467 . Vermüe . M. H. . Beeftink . H. H. . von Stockar . U..
  4. Leitgeb . M. . Knez . ž. . November 1990 . The influence of water on the synthesis of n‐butyl oleate by immobilized Mucor miehei lipase . Journal of the American Oil Chemists' Society . en . 67 . 11 . 775–778 . 10.1007/BF02540490 . 84864739 . 0003-021X.
  5. Zhou . Ningning . Yang . Liancheng . Wang . Yuehan . Ding . Yunlong . 2022-08-01 . N-butyl oleate catalyzed- synthesized by triethylamine citrate lonic liquid . Journal of Physics: Conference Series . 2321 . 1 . 012022 . 10.1088/1742-6596/2321/1/012022 . 2022JPhCS2321a2022Z . 251491831 . 1742-6588. free .
  6. Book: 109. Bouveault - Blanc Reduction. Comprehensive Organic Name Reactions and Reagents. 493–496. 2009. 10.1002/9780470638859.conrr109. Zerong. Wang. 978-0-471-70450-8.
  7. Web site: PubChem . Butyl oleate . 2023-11-10 . pubchem.ncbi.nlm.nih.gov . en.
  8. Web site: EU Commission Implementing Regulation adopting the list of flavouring substances . 2012-10-01 . 2023-11-10 . en.
  9. Web site: Inventory of Food Contact Substances Listed in 21 CFR . 2023-11-10 . www.cfsanappsexternal.fda.gov . en-US.
  10. Dailey . Oliver D. . Prevost . Nicolette T. . Strahan . Gary D. . July 2008 . Synthesis and Structural Analysis of Branched‐Chain Derivatives of Methyl Oleate . Journal of the American Oil Chemists' Society . en . 85 . 7 . 647–653 . 10.1007/s11746-008-1235-9 . 84876707 . 0003-021X.
  11. Riser . G. R. . Bloom . F. W. . Witnauer . L. P. . March 1964 . Evaluation of butyl stearate, butyl oleate, butyl ricinoleate, and methyl oleate as poly(vinyl chloride) plasticizers . Journal of the American Oil Chemists' Society . en . 41 . 3 . 172–174 . 10.1007/BF03024639 . 101771799 . 0003-021X.
  12. Ghamgui . Hanen . Karra-Chaâbouni . Maha . Gargouri . Youssef . 2004-09-01 . 1-Butyl oleate synthesis by immobilized lipase from Rhizopus oryzae: a comparative study between n-hexane and solvent-free system . Enzyme and Microbial Technology . 35 . 4 . 355–363 . 10.1016/j.enzmictec.2004.06.002 . 0141-0229.
  13. Lee . Inmok . Johnson . Lawrence A. . Hammond . Earl G. . October 1995 . Use of branched‐chain esters to reduce the crystallization temperature of biodiesel . Journal of the American Oil Chemists' Society . en . 72 . 10 . 1155–1160 . 10.1007/BF02540982 . 84340949 . 0003-021X.

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Butyl oleate".

Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2024, A B Cryer, All Rights Reserved. Cookie policy.