Fatty Acids
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Fatty Acids

Chemistry, Synthesis, and Applications

Moghis U. Ahmad, Moghis U. Ahmad

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eBook - ePub

Fatty Acids

Chemistry, Synthesis, and Applications

Moghis U. Ahmad, Moghis U. Ahmad

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About This Book

Fatty Acids: Chemistry, Synthesis and Applications is a comprehensive source of information about a wide range of industrially important fatty acids. This practical resource provides key insights into the chemistry, synthesis, industrial applications, derivatives, and analysis of fatty acids, and the chemical modifications that transform them for use in products from biodiesel fuels to pharmaceuticals.

Written by a team of industry experts, Fatty Acids includes detailed descriptions of fatty acid crystallization, enzymatic synthesis, and microbial production. This book focuses heavily on the chemistry of trans fatty acids, with extensive explanations of their synthesis and measurement. Further, the book addresses advances in the analytical methodology, including mass spectrometry, of fatty acids as well as their derivatives.

This book serves as a reference manual to a new generation of lipid scientists and researchers; a useful resource for oleochemical industries; and a valuable teaching aid for undergraduate and graduate students who are interested in fields related to the chemistry of oils, fats, and food.

  • Includes recent developments in the synthesis of fatty acid derivatives, as renewable raw materials for the chemical industry
  • Presents efficient synthetic methods for the dietary trans fatty acids in multi-gram scale allowing scientists and researchers to study dietary effects of individual trans fatty acids on human health
  • Addresses uses of fats and fatty acids in foods and nutrition
  • Identifies the roles of fatty acids and derivatives in cosmetic technology

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Chapter 1

History of Fatty Acids Chemistry*

Gary R. List1, James A. Kenar2 and Bryan R. Moser2, 1G.R. List Consulting, Washington, IL, United States, 2National Center for Agricultural Utilization Research, Peoria, IL, United States

Abstract

Fatty acids are basic renewable chemical building blocks that can be used as intermediates for a multitude of products. Today the global value of fatty acids exceeds 18 billion dollars and is expected to increase to nearly 26 billion over the period from 2014 to 2019. From its auspicious beginnings, the growth of the fats and oils industry has rested upon the shoulders of those that have gone before and worked tirelessly to understand fatty acids and expand their utilization. Because of the important advances made by these and other researchers, renewable oleochemicals are now an important component of the worldwide chemical industry. This chapter provides a brief general historical perspective of some important developments in the chemistry of fatty acids.

Keywords

History; fatty acids; oleochemistry; fats and oils; lipids

1.1 Introduction

The history of fatty acids is a complex one with discoveries often coinciding. However, a number of landmark developments that had significant impact are covered here. The historian is often challenged by who discovered what and when. Fortunately, most of the major events and discoveries surrounding the chemistry of fatty acids are well documented in journal literature. The application of these discoveries in industry is often times difficult to discern because they are mainly documented in the patent literature, which can be time consuming to search, difficult to interpret, and most patents contain references to other patents, which in turn must be examined for prior art. A chronological summary of important discoveries in fatty acid, oleochemical, and triacylglycerol chemistry is shown in Table 1.1. This list is compiled from various sources including the open literature, patents, and chronological compilations from Blank (1942) and the Cyberlipid website (Anonymous, 2016).
Table 1.1
Chronological Summary of Important Discoveries in Fatty Acid, Oleochemical, and Triacylglycerol Chemistry
Year Event
800 Soap produced in Germany
900 Soap produced in France
1600 Soap expands in France
1768 Candles exported to Great Britain
1779 Discovery of glycerol
1801 First oil mill in United States
1811 Bleaching with bone black
1814 Butyric acid discovered
1816 Saponification discovered
1817 Stearic acid discovered
1818 Valeric, caproic, oleic acids isolated
1819 Elaidizination of oleic acid
1823 Chevreul publishes Chemistry of Fats and Oils
1825 Candles patented in France
1825 Distillation of fatty acids
1828 Method for separation of solid and liquid fatty acids
1829 Splitting of tallow with sulfuric acid
1833 Saponification of fats with lime/pressure
1841 Myristic acid discovered
1844 First synthesis of a trigylceride
1844 Linoleic acid discovered
1848 Behenic acid discovered, ricinoleic acid discovered
1849 Lauric acid discovered
1849 Erucic acid discovered
1851 Autoclave for saponification
1852 Polymorphism discovered
1852 Interesterification discovered
1853 Term gylceride first used
1855 Correct structure of glycerol
1855 Margaric acid a mixture
1869 Margarine discovered
1879 Soxhlet extraction
1879 Saponification index
1880 Bleaching patented
1881 Hydroxy myristic acid discovered
1883 Chill roller patented
1884 Iodine value reported
1886 Diene structure of linoleic acid
1886 Tax on margarine
1887 Triene acid in hempseed oil
1889 Death of Chevreul
1892 First acetylenic acid reported
1894 Correct structure of ricinoleic acid
1895 Engine runs on peanut oil
1895 First book on the chemistry of fats and oils
1895 First English book on fats
1895 Lead salts for separation of solid/liquid triglycerides
1897 Discovery of hydrogenation/gas phase
1898 Fat-splitting patented
1898 Correct structure of oleic acid
1898 Liquid chromatography reported
1900 Benzenestearosulphonic acid as fat-splitting catalyst
1903 Hydrogenation in liquid phase
1904 First cyclopentyl acid discovered
1906 Hydrogenation of whale oil
1907 Reagent for splitting of fats
1911 Crisco shortening marketed
1915 Hydrogenation patented
1918 Continuous centrifuge patented
1920 Dimer acids discovered
1921 Separation of solid and liquid fatty acids
1923 Continuous refining patented
1923 Process for lecithin
1924 Industrial interesterification patented
1927 Method for classifying fats
1929 Isomerization during hydrogenation reported
1929 Essential fatty acids discovered
1930 Votator patented
1931 X-ray diffraction used for fatty acids
1931 Continuous fat-splitting patented
1932 Spray shortening
1933 Distillation of fatty acids patented
1933 High-ratio shortenings
1934 Synthesis of oleic acid
1934 First solvent extraction plant in United States
1934 Centrifugal refining introduced
1936 Distillation of fatty acids patented
1936 Primex shortening marketed
1937 Conjugation of linoleic acid by alkali
1937 Synthesis of linoleic acid
1940 Hilditch published Chemical Constitution of Fats
1940 Fatty amines/nitriles patented
1942 DHA from fish oil
1942 Chronology of fats, oils, waxes
1944 Comparison of fat-splitting catalysts
1945 Bailey published Industrial Oil and Fat Products
1945 Displacement analysis for fatty acids reported
1945 Relative rates of fatty acid oxidation reported
1947 Swiftning shortening marketed
1948 Directed interesterification reported
1948 Bailey published cottonseed book
1949 Mechanism of hydrogenation reported
1950 Bailey published melting and solidification of fats
1950 Markley published soybeans and products, 2 volumes
1951 Second edition of Bailey’s book published
1951 Thin-layer chromatography introduced
1952 GC introduced
1953 Death of Bailey
1954 Eckey published third edition of Vegetable Fats and Oils
1954 First soft margarine—Chiffon
1955 Synthesis of mixed acid triglyceride
1955 Golden Fluffo shortening marketed
1956 Stahl advances thin-layer chromatography
1960 Theory of glyceride structures proposed
1961 Hydrogenated winterized soybean oil marketed
1963 Nobel prize for Ziegler-Natta catalyst
1964 Last volume edition of Bailey’s book
1964 Olefin disproportination reported
1964 Markley published five-volume set on fatty acids
1965 Death of Hilditch
1974 Metathesis for synthesis of mono- and dicarboxylic acids
1980 Fatty acids published AOCS Press
1993 First trait modified soybean oil commercialized
2003 Trans fat labeling law
2004 Metathesis reviewed
2004 Metathesis for long-chain dicarboxylic acids
2005 Nobel Prize ...

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