History of Lecithin and Phospholipids (1850-2016)

William Shurtleff, Akiko AoyagiISBN: 978-1-928914-86-0

Publication Date: 2016 May 20

Number of References in Bibliography: 2825

Earliest Reference: 1793

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Special thanks to Armin Wendel of Germany.
More than any other person (by far) Armin has transformed this book. First, he is responsible for 553 documents being in this book that would probably not be there without him. In the 1990s he decided to write a book on the history of lecithin / phospholipids. He wrote excellent biographies (in German) of all the most important figures in the history of phospholipids in Germany and cited his sources. He even wrote a history of soybeans in the Western world. He wrote several outstanding articles for INFORM and other periodicals, and gave an award-winning Power-Point presentation. He retired in 2010. But alas, many of his responsibilities continued after retirement and at some point he realized that he would never find the time to finish his history book. So when he received an alert that Soyinfo Center had published a book on the History of Soybeans and Soyfoods in Germany, he contacted us (in July 2015) and asked if we were planning a history of lecithin. Indeed we were and we had already done most of the research for it – or so we thought. For the past year Armin has sent us (via hundreds of e-mails) a wealth of materials on the history of lecithin and answered countless questions.
      In the early 1970s, Armin joined Nattermann Phospholipids GmbH (in Cologne) and quickly rose through the ranks. In 1999 he was Managing Director of Nattermann Phospholipid GmbH, Köln (Cologne), Germany, and Chairman of the Board at American Lecithin Company (Oxford, Connecticut, USA). In 2002 Nattermann Phospholipid GmbH became an independent company. After retiring in 2010, he worked as a consultant, and at the Phospholipid Research Center: http://www.phospholipid-institute.com. Armin has a deep understanding of the patent literature related to phospholipids and a marvelous, well organized collection (in digital PDF format) of most of the key books and articles concerning lecithin. He is one of the world’s foremost authorities on lecithin and other phospholipids.
      To Armin our deepest thanks for his mastery, his kindness, generosity and patience – and for transforming this book.
 
 
WHAT IS SOY LECITHIN?
Lecithin is the popular and commercial name for a naturally occurring mixture of phospholipids (formerly called phosphatides), which varies in color from light tan to dark reddish brown and in consistency from a fluid to a plastic solid. Lecithin is the gummy material contained in crude vegetable oils which can be removed by degumming. Soybeans are by far the most important source of commercial lecithin and lecithin is the most important by-product of the soy oil processing industry because of its many applications in foods and in nonfood industrial products. The three main phospholipids in this complex mixture called "commercial soy lecithin" are phosphatidylcholine (also called "pure" or "chemical" lecithin to distinguish it from the natural mixture), phosphatidylethanolamine (popularly called "cephalin"), and phosphatidylinositols (also called inositol phosphatides). Commercial soy lecithin also typically contains roughly 30-35% unrefined soy oil. Indeed lecithin is one of the most complex and versatile substances derived from the soybean.
 
      Etymology and Nomenclature: The word "lecithin" is derived from the Greek term lekithos meaning "egg yolk." In 1846 Gobley isolated lecithin from egg yolk and in 1850 gave it its present name (Maclean and Maclean 1927). In the late 1800s it was also spelled "lecithine" in English, a spelling that is still (according to Kunze 1941) used (conveniently) in German to refer to the pure or chemical lecithin. In present-day English, the term "lecithin" has two different meanings, which can be confusing. To most food processors and food chemists it refers to the natural complex mixture of phospholipids, but to most regular chemists, biochemists, and pharmacists it is a trivial term for the chemically pure phospholipid, phosphatidyl choline. In this book we will try to explain in which sense we are using the word. The commercial term "soybean phospholipids" may be used to denote the oil-free lecithin complex.
 
      Manufacture: Lecithin is obtained in the process of degumming crude soy oil, usually at the refinery of the company making commercial lecithin rather than at the oil mill. Crude soy oil contains an average of 1.8% (range 1.2-3.2%; Bailey 1951) hydratable compounds, primarily lecithin phospholipids. Roughly 1% of live steam or warm water is then added to the crude soy oil at about 70ºC., in a batch or continuous process. The emulsion is then agitated or stirred for 10-60 minutes as the phospholipids hydrate and agglomerate, forming a heavy oil-insoluble sludge, which is separated from the oil by use of a centrifuge. The sludge coming from the degumming centrifuge, a lecithin and water emulsion containing 25-50% water, may then be bleached once or twice, typically with hydrogen peroxide, to reduce its color from brown or beige to light yellow. Fluidizing additives can then be added to reduce the viscosity to that of honey and prevent the end product, on cooling, from being a highly plastic solid. Finally the product is film or batch dried to reduce the moisture to about 1% (Szuhaj 1980). Whether bleached or not, the finished commercial product is called "unrefined lecithin" or "natural lecithin;" it contains 65-70% phospholipids and 30-35% crude soy oil. The oil in unrefined lecithin can be removed by extraction with acetone (phospholipids are insoluble in acetone) to give a dry granular product called "refined lecithin."
 
      Varieties of Lecithin and Their Composition: All varieties of soy lecithin can be classified into three broad types: unrefined or natural (including bleached varieties), refined, and chemically modified. Unrefined or natural lecithin comes in six basic varieties, long defined by specifications of the National Soybean Processors Association: plastic or fluid, each either unbleached, bleached, or double bleached. (Because fluid lecithins are easier to handle and dissolve more rapidly in various solvents, only small amounts of plastic grades are now produced.) Refined lecithin (which has had the oil removed using acetone) comes in three basic varieties: custom blended natural, oil free phospholipids (as is or custom blended), and alcohol-fractionated oil-free phospholipids (as is or custom blended). These latter special refined grades, which may contain 60-99.7% phosphatidyl choline, are used mostly for pharmaceutical applications and research (Brekke 1980). Chemically modified lecithin products, altered through selective chemical treatment, improve lecithin's compatibility to certain systems. Szuhaj (1983), using another method of classification, has noted that in addition to the six basic types of natural or unrefined lecithin, there are six types of upgraded lecithin products, including clarified lecithins (filtered), fluidized lecithins, compounded lecithins, hydroxylated lecithin, deoiled lecithin (granular), and fractionated lecithin.
Lecithin is also available as a dietary supplement in two forms: as granular lecithin (oil-free refined lecithin with calcium phosphate as a flow agent) and as capsules, containing a dispersion in oil (Wood and Allison 1981).
Structurally, the phospholipids in soy lecithin consist of glycerides (the basic component of soy oil) in which one fatty acid radical has been replaced with phosphoric acid. In the case of pure or chemical lecithin (phosphatidyl choline), the phosphoric acid is further esterified with choline; in cephalin it is similarly esterified with cholamine. Lecithin is composed mostly of fatty acids, and they are in roughly the same proportion as in soy oil; 50-57% linoleic and 5% linolenic.
 
      Natural Sources of Lecithin: Themost concentrated natural and unrefined sources of lecithin are soybeans (1.48 to 3.08% lecithin), peanuts (1.11%), calf liver (0.85%), wheat (0.61%), oatmeal (0.65%), and eggs (0.39%) (Wood and Allison 1981). The human spinal cord contains 6-10% lecithin and the human brain 4-6% lecithin in fresh substance. Among refined substances, especially concentrated sources of lecithin include dehydrated (powdered) egg yolk (14-20%), natural egg yolk (7-10%), wheat germ 2.82%, soy oil (1.8% but 2.65% including the 30-35% entrained soy oil), and butterfat (1.4%). Soy oil has the highest lecithin and phospholipid content of any known oil; other vegetable oils average 0.5% lecithin. Unlike animal phospholipids, soybean phospholipids contain no cholesterol. In plant seeds the phospholipids are largely associated with oil, but strangely their content varies roughly with the protein rather than the oil content (Stanley 1950). Moreover, all of the above indicates that phospholipids and lecithin appear to be closely connected with the most important vital and reproductive organs and processes. In addition to the spinal cord, brain, eggs, and seeds, they are also concentrated in the nerves, liver, kidneys, and sperm. Actually, lecithin is found in the cell membranes of all human cells, and it tends to be most concentrated where membrane functions are specialized. Lecithin compounds are also closely associated with fatty acids in the body.
 
      Functional Properties. Lecithin is a multi-functional surface-active agent. Each molecule has, like Janus, two faces. The fatty-acid portion of the molecule is attracted to fats (it is lipotrophic) and the opposite end is attracted to water (it is hydrotrophic). Because of this dual nature, lecithin molecules tend to position themselves at the boundary between immiscible materials, such as oil and water. There they serve many useful functions through a surface modifying effect. According to Szuhaj (1980, 1983) lecithin serves the following major functions: (1) Emulsifying allows the mixing of otherwise immiscible substances, especially in water-in-oil systems, such as margarine and chocolate. This is the most widespread of its various uses; (2) Solubilization makes it possible to dissolve oils (such as flavor oils and oil-soluble colors) in water; (3) Suspension, for example, keeps pigments dispersed in paints, preventing agglomeration; (4) Wetting/instantizing helps powders to dissolve quickly in water; (5) Lubrication and Release; when lecithin is applied in a thin film to a cooking utensil or a mold, it promotes release of food or other materials from that surface; (6) Crystallization Control is used especially to control the crystallization of sugar in fat systems, as in chocolate; (7) Complexing tends to retard crystallization of starch associated with staling in baked goods. (8) Anti-spatter, asin margarine; (9) Viscosity Modifying, as in chocolate;and (10) Therapeutical. It also serves as a stabilizer in ice creams and shortenings and as an antioxidant in oils and fats.
 
      Food Uses. Lecithin is used in a surprisingly large array of our daily foods. Perhaps most widely used in margarine (for anti-spatter and as an emulsifier), it is also used in chocolates, caramels and coatings (to control viscosity, crystallization, weepage, and sticking), in chewing gum (for its softening, plasticizing, and release effects), in instant foods such as cocoa powders, coffee creamer and instant breakfast (for wetting, dispersing, and emulsifying), in calf milk replacers (to add energy and aid digestibility and emulsification). It is also found in baked goods, cheeses, meat and poultry products, dairy and imitation dairy products, and still other products (Stanley 1950; Brekke 1980; Szuhaj 1980, 1983).
 
      Therapeutic Uses: Much research has been done and is being done on the therapeutic use of lecithin, especially in the prevention or treatment of neurochemical and cardiovascular disorders. Although the results are not conclusive, many health food consumers use lecithin for benefits they believe it will bring in these areas.
 
      Nonfood and Industrial Uses: In this realm there are at least as many applications as in the food industry. Lecithin is used in cosmetics, pharmaceuticals, coatings (paints, magnetic tape coatings, waxes, polishes, wood coatings), plastic and rubber industry, glass and ceramic processing, paper and printing, masonry and asphalt products, petroleum industry, metal processing, pesticides, adhesives, textiles, and leathers (Stanley 1950; Brekke 1980; Szuhaj 1980, 1983).
 
      World Production:The major countries refining soy oil (USA, Western Europe, Japan) are also the major producers of soy lecithin. Stanley (1950) estimated that in the year 1936-37 the world produced 1,787,000 tonnes (metric tons) of soy oil. From this it recovered 1,814 tonnes of lecithin and left 47,174 tonnes unrecovered, thereby utilizing only about 4% of potential production. The main producers were the USA, Germany, Japan, Denmark, and Norway. In 1948 world soy lecithin recovery was estimated at 4,535 tonnes, and plant derived lecithin other than soy was estimated at one-fifth this amount. Recovery and utilization of soy lecithin was thought to be less than 10% of potential production. In 1976 Van Nieuwenhuyzen (in Brekke 1980) estimated world recovery of soy lecithin to be 90,700 tonnes a year, from 8.8 million tonnes of soy oil produced containing 233,200 tonnes of soy lecithin. Thus roughly 39% of the total lecithin was recovered and used. Clearly the percentage used has been increasing, but the majority that could be recovered is not yet used directly. The unsold portion is mixed back into defatted soybean meal, which is used for livestock fodder. Although this practice is not widely discussed by the industry, the lecithin is considered neither negative nor a positive factor.
 
 
Chronology/timeline of lecithin
 
1719 – J.T. Hensing isolated phosphorus compounds from the brain.
 
1812 – L.N. Vaquelin (1755-1809) isolated phosphorus- and fat-containing compounds from the brain.
 
1850 June – The word lecithin is first used worldwide by T.N. Gobley in French, in an article titled Recherches chimiques sur les oeufs de carpe [Chemical investigations on carp eggs]. He isolated a phosphorus-containing substance from these eggs which he called Lécithin (first mentioned on p. 403), a term derived from the Greek word lekithos or “egg yolk” (see p. 411).
 
1861 – Lecithin (actually “lecithine” is first mentioned in English in the book Elements of Medical Zoology (translated from the French), by Alfred Moquin-Tandon. It states (Book III, Section II, Chap. 1, p. 85-86): “According to a recent analysis of M. Gobley, helcine cannot be considered as a proximate principle; it does not contain sulphur; it consists, like human venous blood, of oleine, margarine, cholesterine, lecithine, and cerebrine.”
 
1883 April 19Ueber die Bestandtheile der Bohnen von Soja hispida [On the constituents of soybeans], an article by E. Meissl and F. Böcker is the earliest document seen stating that soybeans contain lecithin. It is also the earliest German-language document seen that uses the word Lecithin to refer to lecithin (Sitzungsberichte der Kaiserlichen Akademie der Wissenschaften…).
 
1884 – Lecithin is first mentioned in English in connection with soybeans in the Year-Book of Pharmacy, in an English-language summary of the 1883 German-language article by Meissl and Böcker.
 
1884A Treatise on the Chemical Constitution of the Brain: Based throughout upon Original Researches, by J.L. William Thudichum is published. This is the earliest English-language document seen that contains the word “phospholipids,” which appears on many pages throughout, e.g. “Phospholipids are the centre of life, and chemical soul of all bioplasm whatever, that of plants as well as animals… Amongst these properties [of phospholipids] none are more deserving of further inquiry than those which may be described as their power of colloidation. Without this power no brain as an organ would be possible, as indeed the existence of all bioplasm is dependent on the colloid state” (p. xii).
      Thudichum also uses the words “kephalins” and “kephalin” – now called “cephalin(s)” (p. 52-64). The word “lecithin” is used on 28 pages of this book.
 
1907 July 9 – The earliest known German patent for lecithin is applied for by H.C. Buer, PhD, from Marienburg. Cologne, Germany. This patent, issued in July 1908 as German patent 200,253, was titled Process for obtaining lecithin from the seeds of lupins and other legumes [English translation].
      At a time when the only source of lecithin was the yolk of eggs, Dr. Buer had the foresight to look for a less expensive plant-based source. Lupins served as his first source.
      Also in 1907, Dr. H.C. Buer founded the company Neura-Werk Dr. Buer & Co. KG (Dr. Buer & Co. Neura Factory Limited Partnership) in Cologne, which launched as its first product Dr. Buer Neura Lecithin Pearls (Dr. Buer-Neura-Lecithinperlen) (Wendel 1999, C.H. Buer).
      Throughout the 20th century, the Germans are the undisputed leaders in lecithin research and patents. From 1900 to 1913, in Germany more than 100 preparations containing lecithin or phospholipids were introduced commercially. Note that in the early years the word was often spelled Lezithin in German (this is important when searching the superb German patents database, DEPATISnet) and it was sometimes spelled “Lecithine” in English.
 
1908 Nov. 14 – An ad for “Ovaltine: a food drink” says that it is made with eggs which contain “active lecithin, the best brain and nerve tonic known” (Gloucester Journal {England}, p. 10).
 
1908 – Egg lecithin is a commercial product in Europe. More than 100 pharmaceuticals containing egg lecithin are on the market. The main manufacturer and distributor is J.D. Riedel AG, Berlin. His brand is Lecithol.
 
1909 March 25 – The earliest known U.S. patent for lecithin is applied for by Heinrich Carl Buer, a chemist from Bonn-on-the-Rhine, Germany. This patent, issued in Aug. 1911 as U.S. patent 1,001,247, was titled Process for the extraction of lecithin from the seeds of lupines and other pulses. About “1-1½ kilograms of pure lecithin are obtained from 100 kilograms of lupines.” This is the earliest U.S. patent seen that mentions “oil-free lecithin.”
      As soon as the source of lecithin moves from animal sources (eggs) to plant sources (oilseeds), the price begins to decrease.
 
1909 – By June, Soybeans are first imported into Germany on a commercial scale (Oil, Paint and Drug Reporter. 1909. June 21, p. 7-8).
 
1910 March – Germany removes it duty on soybeans so they can now be imported duty-free. (Teichmann, William C. 1911. "Soya-bean industry in Germany."
Daily Consular and Trade Reports {U.S. Bureau of Manufactures, Department of Commerce and Labor}. May 13. p. 680-81).
 
1910 – From January to Oct., 28,110 tonnes of soybeans were imported. They originate in Manchuria and arrive via the ports of Vladivostok, Dalny, etc. The main importer in Germany is the firm Henry P. Newman in Hamburg. The processing of the beans into oil and cake takes place in Hamburg oil factories, for example Thörls Vereinigte Oelfabriken A.-G. in Harburg. A new factory is under construction at Stettin (Chemische Industrie {Berlin}. 1910, Dec. 15. p. 792).
      Thörl’s was processing these soybeans using benzine as a solvent as early as 1913 (Horvath 1938, p. 73). This solvent enabled the company to make a good-tasting and inexpensive soy flour; Aguma, which was introduced by Oct. 1913 (Allgemeine Medizinische Central-Zeitung. 1913. Oct. 11, p. 483-86).
 
1918 – The first long (206-page) English-language bibliography on lecithin is titled Lecithin and Allied Substances: The Lipins [Lipids], by Hugh MacLean of London. It contains 636 references, and soja or soya are mentioned on 3 pages.
 
1921 June 25 – German patent 382,191, by Hermann Bollmann, founder of Hansa Muehle (The Hansa Mill) in Hamburg, is the earliest German patent seen that mentions both lecithin and soybeans. It marks the beginning of the commercial availability of soy lecithin worldwide. Moreover, this is also the earliest German patent seen that contains the string entöl* or the word entöl (meaning "deoiled") in connection with lecithin. Previously, most commercial lecithin contained at least 1/3 oil.
      The U.S counterpart of this patent is No. 1,464,557, application filed 10 June 1922. However, the soybean is not mentioned in this U.S. patent. In its place Bollmann refers repeatedly (15 times) to “vegetable raw materials.” This is one of the most important early U.S. patents for lecithin.
      The first big uses for soy lecithin in Europe were in margarine and chocolate (Eichberg, 1947, Chemurgic Digest, March 31, p. 109-11).
 
1924 – Hansa Muehle in Hamburg, Germany now makes 50 metric tons of soybean lecithin per year.
 
1925 Jan. – The term “soy bean lecithin” is first used in English by Levene and Rolph, in the Journal of Biological Chemistry (p. 759-66). They write: “Through the courtesy of Dr. H. Bollmann of the Hanseatische Mühlenwerke [Hansa Mühle, in Germany] a considerable quantity of commercial lecithin obtained from soy beans was placed at our disposal. From this material lecithin was prepared which was free from cephalin.”
      This is also the earliest English-language document that mentions commercial lecithin and the first which describes making lecithin that is free of cephalin.
 
1925 May 28 – Hermann Bollmann of Hansa Muehle in Hamburg, Germany, applies for the earliest known U.S. patent that mentions both soybeans and lecithin (“soya lecithin”). U.S. Patent 1,575,529, titled “Process of increasing the durability of pure salad or sweet oils” is issued on 2 March 1926.
      In this patent he discovered that the addition of a small percentage lecithin to refined oils served to prevent or retard rancidity and rancid taste, and to increase the durability and keeping qualities of such oils.
 
1925 Nov. 9 – The term “soya lecithin” is first used in English by Hermann Bollmann in British Patent 260,108, “A method for improving the durability of liquid vegetable oils.”
 
1925 Nov. 9 – Hermann Bollmann, president and founder of Hansa Muehle, applies for British Patent No. 262,239, titled “An improved process for producing soluble cocoa powders.” This is the earliest document (or patent) seen showing how lecithin can improve the processing of cocoa beans or the making of chocolate. Only very small amount of lecithin (0.1 to 0.5%) is needed to have a large emulsifying effect.
      This is also the earliest English-language patent that uses the word “purification” (or one of its congeners) in connection with lecithin or phospholipids.
 
1926 May – The word “cephalin” (or “cephalins”) is first used in English in an article by Levene and Rolph titled “Plant phosphatides. II. Lecithin, cephalin, and so called cuorin of the soy bean,” in J. of Biological Chemistry (p. 285-93).
 
1927 July 17 – German patent 514,399, by Hermann Bollmann and Bruno Rewald describes a means for greasing leather. This is Dr. Bruno Rewald’s earliest patent related to lecithin; this lecithin is made from soybean oil. It is also the world’s earliest document seen worldwide that describes an industrial (non-food, non-feed) use for soy lecithin, and the earliest known patent related to soy lecithin and leatherworking.
 
1927 July 17 – The German word Sojaschlamm (“Soybean sludge”), referring to a mixture of mostly lecithin and water, is first used in German Patent 522,041 by Bruno Rewald. The patent is assigned to Hansa Muehle.
 
1927-1928 – Joseph Eichberg of American Associated Companies (AAC) in Atlanta, Georgia, who had heard about Hansa Muehle as early as 1923, contacts then visits them in Hamburg, Germany to ask about being their lecithin representative in the USA. A deal is finalized. Lecithin is first imported into the U.S. (non-commercially) from Europe by American Associated Companies, Atlanta, Georgia, then after organization of American Lecithin Corporation (ALC) from 1930 to 1934 by the latter (Eichberg 1983 letter of April 11 and interview of March 25; Eichberg 1992 letter of Aug. 3).
 
1929 July 30 – The term “soya bean lecithin” and the term “vegetable lecithin” are first used in English by Hermann Bollmann and Bruno Rewald in British Patent 330,450, “Improvements in and relating to the production of chocolate.” They write: “It is sufficient to add 0.1 to 0.5% lecithin in order to attain the desired effect and to prevent the goods becoming grey and unattractive for a long period.” The patent does not mention that lecithin can also (and more importantly) lower the viscosity of chocolate.
 
1929 Aug. 19 – Soy lecithin’s future arrives in the United States in the person of Bruno Rewald, PhD of Hansa Muehle (Hamburg, Germany); this is his first trip to the United States. He arrives in New York harbor on this date on the ship Albert Ballin (Hamburg America line). He and Adolf Schneider (also of Hansa Muehle) travel to Atlanta, Georgia to meet Joseph Eichberg. Together they travel throughout the Midwest to visit America’s leading soybean processors (The Glidden Co., A.E. Staley Manufacturing Co., Archer-Daniels-Midland Co., etc.) to find a domestic source of lecithin and to encourage their interest in lecithin and in the “Bollmann-Process” soy lecithin patents they hold. Joseph Eichberg becomes Hansa Muehle’s representative in America, establishes the American Lecithin Company in Atlanta (by July 1930), and for the next 50+ years works tirelessly to establish lecithin as a new commodity in the USA.
 
1929 July 8 – Hermann Bollmann and Bruno Rewald apply for British Patent No. 330,450. “Improvements in and relating to the production of chocolate.” After it is accepted/issued (12 June 1930), it governs the use of lecithin in chocolate in England. Thus, only firms which have purchased a license under this patent may make chocolate that contains lecithin. As of July 1939 only these brands “made by the following British firms, may be used: Emulgo (Messrs. Fredk. Boehm Ltd.); Chocothin (Messrs. A. Lane and Co. Ltd.); and Collabrac (Messrs. A. Boake, Roberts and Co., Ltd.)” (Stanley 1939).
 
1929 Oct. 21 – Hermann Bollmann applies for British patent 356,384 titled “Improvements in and relating to the production and purification of phosphatides.” It is the earliest known patent to describe bleaching of lecithin with hydrogen peroxide. The priority date was 21 Oct. 1929 in Germany.
 
1929 Nov. – The fact that the addition of small amounts of lecithin to chocolate can dramatically lower its viscosity is first mentioned by Sherman Woodrow. However, according to Armin Wendel, a German lecithin expert, the earliest known use of lecithin was that from egg yolks in chocolate.
 
1929 – Hansa Muehle in Hamburg, Germany now makes 800 metric tons of soybean lecithin per year.
 
1929 – “Soybean lecithin first appeared on the American market and for several years thereafter was imported from Europe” (Eichberg 1942, p. 3). Prior to 1929 only egg lecithin was available – and very expensive. The first big use for soy lecithin in the USA was in chocolate (Eichburg 1947).
 
1929 – The word lecithin is first used in Japanese in connection with soybeans by Sato and Seto, writing in a Manchurian periodical.
 
1930 Jan. – The basic idea that “commercial lecithin” contains a mixture of lecithin and other substances is first mentioned in the journal Food Manufacture (London). It states: Commercial lecithin has a waxy consistency, a bland, oily flavour, and a faint odour; it is said to contain about 60% lecithin.
 
1930 June – The earliest known mention of the use of lecithin in margarine appears in U.S. patent 1,762,077 by Bruno Rewald, titled “Production of egg-yolk substitutes.”
 
1930 July 16 – The earliest known reference to American Lecithin Corp. (Or Company, of Atlanta, Georgia) appears when they are assigned U.S. Patent 1,831,728 by Earl B. Working. He applied for a patent, titled “Shortening composition and method,” on this date.
 
1930 Oct. – The word “choline” is first used in English in connection with lecithin in an article by Suzuki and Yokoyama titled “Soy bean lecithins. I. The separation of alpha- and beta-series” in Proceedings of the Imperial Academy (Tokyo) (p. 341-44).
 
1930 ca. – American Lecithin Co. (ALC-1) is incorporated in Atlanta, Georgia, with Joseph Eichberg as president. Most of the stock is owned by American Associated Companies, but Hansa Muehle may have owned a small portion. ALC has two main sources of income: Royalties on patents licensed, and profits from sale of lecithin. All the lecithin in the USA from 1930 to 1935 is imported from Germany and Denmark (Eichberg. 1983, March 25 interview; Horvath 1933).
 
1931 Jan. – Ross & Rowe, Inc. of New York City start to advertise their Yelkin brand [soy] lecithin, obtained from Aarhus Oliefabrik in Denmark, as “The new, improved vegetable lecithin.” American Lecithin Co. has its first (small) competitor, which by 1934 becomes a cooperator. This is the earliest document seen that mentions Ross & Rowe in connection with lecithin (Oil and Fat Industries, p. 8).
 
1931 Nov. 13 – The word “sludge” and the terms “soybean sludge” and “soya sludge” (referring to a mixture of mostly lecithin and water) and the term “bleached lecithin” are first used in English in U.S. Patent 1,892,588 titled “Treatment of vegetable lecithin,” by Albert Schweiger. The patent was applied for on Nov. 13 and assigned to Hansa Muehle in Hamburg, Germany.
 
1932 May 27 – An article in the Journal of the Society of Chemical Industry (London) by Avent and Morgan states: “The production of lecithin from soya beans in recent years has made what was hitherto an expensive material comparatively cheap, as well as supplying it in quantity on an industrial scale.”
      It must be emphasized that the term 'commercial lecithin' refers not to chemically pure lecithin, but to the product sold commercially under various trade names which contains about 60% of lecithin, together with other phosphatides, soya-bean oil, etc.
 
1934 – “Prior to 1934, commercial lecithin used in this country was imported largely from Germany and Denmark. The principal German manufacturer, Hanseatische Mühlenwerke A.G. (Hansa-Mühle), marketed its lecithin products in the United States through the American Lecithin Corporation. The principal Danish manufacturer, Aarhus Oliefabrik, A/S (Aarhus), marketed its lecithin products in the United States through Ross & Rowe, Inc.” (Wittcoff 1951, p. 484-85).
 
1934 late – American Lecithin Co. opens a research and sales office on Corona Ave. in Woodside, Long Island, New York. They stay at this address until Oct.1947 when they move to 29-28 41st Avenue in Long Island City, Queens. In April 1949 the address is 57-01 32nd Avenue, Woodside, Queens. In 1961-62 the address is 32-30 61st Street, Woodside, and in 1976-77 it expands to 32-34 61st Street. It remains at this address until at least May 1990 (Queens, New York, telephone directory, white pages).
 
1934 – ADM and Glidden initiate large-scale solvent extraction of soybeans in the United States. ADM purchased from Germany a 150-ton-per day capacity Hildebrandt continuous-flow, counter-current (U-tube) hexane solvent extractor. It began operation in March 1934 on Blackhawk Street in Chicago. It was America's first successful continuous solvent extractor; at the time it was also America's largest and most modern soybean crushing system, and the first to use hexane as a solvent with soybeans. The Glidden Co. purchased an identical solvent extraction plant from Germany and also installed it in Chicago. It began operation in about Nov. 1934 (Shurtleff 1984. “Early soy crushing”).
 
1934 June – Archer Daniels Midland Co. (ADM, Chicago) makes not only the first soy lecithin in the USA, they make the first commercial lecithin of any type. ADM had developed a patent for the use of hexane, the Sorensen and Beale patent, which described the use of hexane in place of the alcohol-benzol procedure. ADM's manufacture of soy lecithin was followed in Dec. 1934 by The Glidden Co. in Chicago (both under license from ALC). Glidden went their own way in the 1940s and not long thereafter ADM did too (Cross 1954, p. 60-61; Eichberg. 1983, March 25 interview).
 
1934 Nov. 19 – The Glidden Co. is now “erecting a plant from the separation of lecithin from crude soya bean oil… The lecithin will be manufactured and refined under patents owned by the Hansa-Muehle Company of Hamburg [Germany]. The product will be marketed under patents owned by the American Lecithin Corporation of the United States.” (Oil, Paint, and Drug Reporter, p. 52). Glidden Lecithin (Food Grade) was on the market by Dec. 1934.
 
1935 March 10 – The modern English term “soy lecithin” is first used by Dr. A.A. Horvath in an article in Industrial and Engineering Chemistry, News Edition (p. 89) titled “Phosphatides of the soy bean: What we know about them.” He writes that “according to [Bruno] Rewald, over 1 million pounds of soy lecithin were used annually in the German margarine industry. For a number of years, soy lecithin was imported into the United States, but recently two mills were built in this country to supply the present-day demand.”
 
1935 – In the USA, the complicated patent situation prompts companies “to join a patent pool.” ALC is reorganized as the American Lecithin Company (ALC-2), an Ohio corporation with headquarters in New York. Glidden and ADM are stockholders. Adrian Joyce, president of The Glidden Co., lives in Cleveland, Ohio, and has a legal staff there. Moreover, Ohio laws are favorable. Eichberg is president of ALC-2 (he worked at headquarters in New York) and Adrian Joyce is chairman of the board. This new ALC grants exclusive manufacturing licenses to ADM and Glidden and a selling license to Ross & Rowe (Eichberg 1983, letter of March 25; Wendel 2000, Aug. p. 892).
 
1937 – Soya lecithin starts to be used in margarine in the USA. That year 36,000 lb were used, rising to 83,000 lb in 1940. Thereafter use of lecithin in U.S. margarine skyrocketed, reaching 659,000 lb in 1945 and an estimated 1,651,000 lb in 1950. Almost all of this lecithin is made in the USA (Howard 1951).
 
1937 July – The word lecithin is first used in Spanish in connection with soy in an article in the periodical Revista de Agricultura (Cuba).
 
1937 Dec. 9 – The word “foots” is first used in English in connection with lecithin in U.S. Patent 2,206,210 by Benjamin H. Thurman. The patent, titled “Process of removing materials containing phosphatides from vegetable oils,” was issued on 2 July 1940.
 
1937 – The word lecithin is first used in Portuguese in connection with soy by Ruben Descartes de Garcia Paula of Brazil in an article about the soybean as a raw material for industry.
 
1939 March – The earliest known published article by Joseph Eichberg (president of American Lecithin Co., Inc., Elmhurst, Long Island) about lecithin appears in Oil and Soap, under the title “Lecithin – Its manufacture and use in the fat and oil industry.” Eichberg is the first to make clear in English that the “soya lecithin of commerce” refers to a mixture of about 25-35% soya oil (the inert carrier) and 65-75% active phosphatides.
 
1939 – Klenk and Sakai in Germany first demonstrate the presence of an inositol-containing phospholipid in soybeans. They first use the term “inositol” in connection with lecithin or soy (Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie 258:33-38).
 
1942 July 6 – Joseph Eichberg of American Lecithin Co applies for his first patent, which is assigned to American Lecithin Co. It is issued as U.S. Patent 2,335,061 on 8 Aug. 1944. He has invented a way of making turpentine free from objectionable appearance by adding a small percentage of lecithin.
 
1942 – The American Lecithin Company, Inc. (Cleveland, Ohio) has total lecithin sales in 1942 of 2.3 million lb. compared to 1.8 million lb. in 1941 (ALC Annual Report).
 
1943 Jan. – American Lecithin Co.’s total sales in 1942 “amounted to 2,345,373 pounds (R&R [Ross & Rowe] 1,371,370 pounds – Alco 974,003 pounds) compared with 1,873,742 pounds in 1941 (dollar value: $874,009.09 and $706,627.11); net profits were $828.61 and $73,928.77 respectively,…” A little over 2% of net sales was spent on “Experimental and Research.” “Sales to the chocolate industry were 449,747 pounds compared with 471,907 pounds in 1941 in spite of the shortage of cocoa beans” caused by World War II (Eichberg 1943. Report of Annual Meeting).
 
1943 March – The words “inositol,” “lipositol” and “ethanolamine” are first used in English in an article by D.W. Woolley titled “Isolation and partial determination of structure of soy bean lipositol, a new inositol-containing phospholipid,” in J. of Biological Chemistry (p. 581-91).
 
1944 Feb. 26Business Week publishes a long, excellent article titled “No war baby: Lecithin, long used by food industry and confectioners, now is widely used in paints, oils, cosmetics, textiles and soaps.” Most commercial lecithin is now extracted from soybeans. “Soya lecithin” now sells for 30-35 cents a pound, which is much less expensive than egg lecithin ($8-12 a pound).
 
1944 Aug. 10 – American Lecithin Co. applies for Alcolec as a registered U.S. trademark. It is issued as U.S. Trademark 412,959 on 3 April 1945.
 
1946 – “Certain trade practices of the American Lecithin Company were modified by Federal Trade Commission action in 1941, and the patent pool arrangement was terminated by Consent Decree in 1946.” By 1950 there were about a dozen known manufacturers of commercial lecithin, most of which were operating under license from the American Lecithin Company (Wittcoff 1951).
 
1947 – The term “phosphatidyl choline” first appears in English in a document by Joseph Eichberg, titled The Lecithin Story – with a Moral. This term refers to “pure lecithin.” It soon begins to be written as one word.
 
1948 – "It can safely be said that during 1934-1938 the world utilized only about 4% of its potential production of soybean lecithin, and it is doubtful whether more than 10% was utilized even in 1948."
      This is also the earliest dated English-language document seen that contains the word “phosphatidylcholine” – written as one word. (Joseph Stanley 1951, in Markley).
 
1948 – In the USA, 8 million pounds of lecithin are recovered – mainly from soy oil – and sold. However an additional 40 million pounds are produced but not recovered (Aylward 1952, July, p. 287).
 
1950 – The word “phospholipids” passes the word “phosphatides” in frequency of use in English-language publications (Google Books Ngram Viewer).
 
1950 – The price of lecithin in the United States has fallen from $0.75 per pound in 1930 to $0.15 per pound in 1950 – a five-fold decrease (Aylward 1952, July, p. 287).
 
1953 May – American Lecithin Co. issues the first of many short leaflets (or brochures) titled “Data-Gram from the Alcolec Laboratory.” Each gives technical details concerning a new application for lecithin. The first one is “Lecithin in Reconstituted Cream and Toppings.”
 
1954 – Lecithin production in the USA rose from 8,000,000 pounds (3,629 metric tons) in 1947, to 26,100,000 pounds (11,839 metric tons) in 1954 – a 3.26-fold increase in 8 years. When centrifuges began to be used to separate the phosphatides from the oil, production became much larger than consumption and prices dropped to oil prices or lower. The drop in price fostered new uses (Cowan 1954, p. 15; Cowan 1958).
 
1955 Jan. – The Glidden Co., Soya Products Div. (in Chicago, Illinois), introduces Glidden RG Lecithin. “RG” stands for “Refined, Granulated.” It is sold in an 8-ounce bottle to consumers – with no health claims. It is one of the first granulated lecithin products.
 
1955 July 12 – Carl Heinz Buer, PhD applies for German patent 1,027,366 titled Process for manufacturing high-percentage stabile emulsions… [English translation] which is the “breakthrough” patent that enables the production of liquid Buer lecithin, which is still very popular today.
 
1958 Sept. 1 – Central Soya Co. takes over the operations of The Glidden Company’s Chemurgy Division – which means all of Glidden’s soy products, including its various lecithin products.
 
1959 June 11 – Central Soya opens and dedicates a new lecithin plant and office building at Gibson City, Illinois (Soybean Digest, July, p. 37)
 
1965 Aug. – The first description of liposomes appears in an article by Bangham, Standish, and Watkins titled “Diffusion of univalent ions across the lamellae of swollen phospholipids” in J. of Molecular Biology (p. 238-52). By March 1989 this article has become a classic, and has been cited in more than 710 publications.
      Liposomes were later found by Bangham et al. to serve as the first good model for biological cell membranes.
 
1968 May – The word “liposomes” in its modern sense first appears in print in a paper by Sessa and Weissmann titled “Phospholipid spherules (liposomes) as a model for biological membranes,” in the Journal of Lipid Research (p. 310-18). Credit for coining the new word is widely given to Weissmann.
 
1976 Jan. – U.S. demand for soybean lecithin is estimated at about 80 million pounds per year (40,000 tons/year). The soybean is currently the only source of commercial lecithin.
      A table shows the approximate percentage composition of commercial crude soybean lecithin:
Phosphatidyl choline (chemical lecithin) 20%
Phosphatidyl ethanolamine 20%
Inositol phosphatides 20%
Soybean oil 35%
Sugars, sterols, and moisture 5%
(Ross Brian 1976, p. 27-29).
 
1976 June – The demand for lecithins worldwide is estimated at 100,000 tons per year. Of this, 30,000 tons are used in Western Europe (van Nieuwhuyzen, p. 435-27).
 
1978 – Statistics for lecithin usage and production are estimated as follows: Of the estimated 110,000 metric tons (tonnes) used worldwide: about 40,000 tonnes were used in Europe, 50,000 tonnes in North America, and 10,000 to 20,000 tonnes in the rest of the world.
      In the same year the use in various European countries was: Belgium 2,000 tonnes. Denmark 1,300 tonnes. Germany (East and West): 13,000 tonnes. England and Ireland: 1,500 tonnes. France 5,000 tonnes. Netherlands 7,000 tonnes. Italy 3,000 to 4,000 tonnes, Sweden 500 tonnes, Spain 4,000 tonnes.
      18,000 to 20,000 tonnes were used in Europe for feeds, and 11,000 to 15,000 tonnes in foods. 2,000 tonnes were used for dietetic and pharmaceutical products. The rest went to industrial uses.
      In 1973 in Europe: Baked goods 3,300 tonnes. Chocolate and sweets 2,700 tonnes. Margarine 3,000 to 4,000 tonnes. And baby foods 700 tonnes (Rebmann 1978).
 
1981 – Commercial lecithin production in the USA was about 33,000 metric tons, but the total commercial lecithin potential from the domestic production of crude soybean oil was about 140,000 metric tons. Therefore only about 23.6% of the potential was actually recovered (Eichberg 1981).
 
1982 Oct. – The three largest uses of lecithin in the USA are probably in the baking industry, the coatings industry [paints, varnishes, etc.], and in the manufacture of margarine (Letter of Oct. 8 from Joseph Eichberg {President, American Lecithin Co., P.O. Box 4056, Atlanta, Georgia} to William Shurtleff of Soyfoods Center).
 
1985 – The word “phosphatidylserine” is first used in connection with lecithin in English in a book chapter by C.R. Scholfield titled “Occurrence, structure, compensation and nomenclature” [of lecithins].
 
1986 – The first commercial liposome product, a cosmetic named Capture®, is launched by Christian Dior of Paris. It is first widely publicized in Jan. 1987.
 
1989 – Nattermann Phospholipid GmbH purchases American Lecithin Co. By this time Nattermann is the world leader in lecithin fractionation technology – which is a major reason the company was acquired in 1986 by the Rhône-Poulenc Group.
 
1996 – “On the history of liposomes,” by Danilo D. Lasic, is published. One of the best English-language histories of the subject seen.
 
1999-2005 – Armin Wendel, an expert on lecithin from Natterman in Germany, writes biographies and histories (in German) of Hermann Bollmann (1880-1935), Dr. Bruno Rewald (1883+), American Lecithin Co., Dr. Hermann Pardun (1908+), C.H. Buer Chemical and Pharmaceutical Factory, Soybeans: from the soybean to soy lecithin, and 150 years of lecithin.
      In May 2001 he delivers a History of Lecithin (Powerpoint Presentation) to the American Oil Chemists’ Society (AOCS) for which he receives an award. In 2005 he writes Biography of Dr. Hans Eikermann 1910-2005. He gives Soyoinfo Center permission to have these translated into English.
      He estimates that in 1999, worldwide, the uses of lecithin are as follows: margarine 25-30%; baking, chocolate and ice cream 25-30%; technical/industrial products 10-20%; cosmetics 3-5%; and pharmaceuticals 3%.
 
2006 – Natterman’s 100th Anniversary (100 Jahre Nattermann) by A. Nattermann & Cie, GmbH (23 p.) is published in Cologne, Germany.
 
2000-2016 – In recent years, there has been great interest and activity in the fields of studying developing liposomes, both as models of biological membranes and as delivery vehicles for pharmaceuticals and cosmetics.

 

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