Partially Hydrogenated Oil
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Fat hydrogenation is the process of combining
unsaturated fat An unsaturated fat is a fat or fatty acid in which there is at least one double bond within the fatty acid chain. A fatty acid chain is Monounsaturated fat, monounsaturated if it contains one double bond, and polyunsaturated fat, polyunsaturated i ...
with hydrogen in order to partially or completely convert it into
saturated fat A saturated fat is a type of fat in which the fatty acid chains have all single bonds between the carbon atoms. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone, and fatty acids that each cont ...
. Typically this
hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...
is done with liquid
vegetable oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of edible plants. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed ...
s resulting in solid or semi-solid
fat In nutrition science, nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such chemical compound, compounds, most commonly those that occur in living beings or in food. The term often refers specif ...
s. Changing the degree of saturation of the fat changes some important physical properties, such as the melting range, which is why liquid oils become semi-solid. Solid or semi-solid fats are preferred for some baked goods such as biscuits and pie dough because how the fat mixes with flour produces a more desirable, crumbly texture in the baked product. Because partially hydrogenated vegetable oils are cheaper than animal fats, are available in a wide range of consistencies, and have other desirable characteristics such as increased oxidative
stability Stability may refer to: Mathematics *Stability theory, the study of the stability of solutions to differential equations and dynamical systems ** Asymptotic stability ** Exponential stability ** Linear stability **Lyapunov stability ** Marginal s ...
and longer
shelf life Shelf life is the length of time that a commodity may be stored without becoming unfit for use, consumption, or sale. In other words, it might refer to whether a commodity should no longer be on a pantry shelf (unfit for use), or no longer on a s ...
, they are the predominant fats used as
shortening Shortening is any fat that is a solid at room temperature and is used to make crumbly pastry and other food products. The idea of shortening dates back to at least the 18th century, well before the invention of modern, shelf-stable vegetable ...
in most commercial baked goods. The process is typically carried out at very high pressure, with the help of a
nickel Nickel is a chemical element; it has symbol Ni and atomic number 28. It is a silvery-white lustrous metal with a slight golden tinge. Nickel is a hard and ductile transition metal. Pure nickel is chemically reactive, but large pieces are slo ...
catalyst that is removed from the final product.


Process

Hydrogenating vegetable oil is done by raising a blend of vegetable oil and a metal catalyst, typically nickel, in near-vacuum to very high temperatures, and introducing hydrogen. This causes the carbon atoms of the oil to break double-bonds with other carbons. Each carbon atom becomes single-bonded to an individual hydrogen atom, and the double bond between carbons can no longer exist. Full hydrogenation results in the conversion of all of the unsaturated fats into saturated fats by transforming all of the double bonds in the fat into single bonds. Partial hydrogenation reduces some, but not all, of the double bonds by the partial replacement with single bonds. The degree of hydrogenation is controlled by restricting the amount of hydrogen, reaction temperature and time, and the catalyst.


History

Nobel Prize The Nobel Prizes ( ; ; ) are awards administered by the Nobel Foundation and granted in accordance with the principle of "for the greatest benefit to humankind". The prizes were first awarded in 1901, marking the fifth anniversary of Alfred N ...
laureate In English, the word laureate has come to signify eminence or association with literary awards or Military awards and decorations, military glory. It is also used for recipients of the Nobel Prize, the Gandhi Peace Award, the Student Peace Pri ...
Paul Sabatier worked in the late 1890s to develop the chemistry of hydrogenation. Whereas Sabatier considered hydrogenation of only vapors, the German
chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a graduated scientist trained in the study of chemistry, or an officially enrolled student in the field. Chemists study the composition of ...
Wilhelm Normann Wilhelm Normann (16 January 1870, in Petershagen – 1 May 1939, in Chemnitz) (sometimes also spelled ''Norman'') was a German chemist who introduced the hydrogenation of fats in 1901. This invention, protected by German patent 141,029 in 1902 ...
showed in 1901 that liquid oils could be hydrogenated, and patented the process in 1902. Normann's hydrogenation process made it possible to stabilize affordable
whale oil Whale oil is oil obtained from the blubber of whales. Oil from the bowhead whale was sometimes known as train-oil, which comes from the Dutch word ''traan'' ("tear drop"). Sperm oil, a special kind of oil used in the cavities of sperm whales, ...
or
fish oil Fish oil is oil derived from the tissues of oily fish. Fish oils contain the omega−3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), precursors of certain eicosanoids that are known to reduce inflammation in the bod ...
for human consumption, a practice kept secret to avoid consumer distaste. During the years 1905–1910, Normann built a fat-hardening facility in the
Herford Herford (; ) is a town in North Rhine-Westphalia, Germany, located in the lowlands between the hill chains of the Wiehen Hills and the Teutoburg Forest. It is situated in the cultural region of Ostwestfalen-Lippe (OWL) and the Detmold (administrat ...
company. At the same time, the invention was extended to a large-scale plant in
Warrington Warrington () is an industrial town in the Borough of Warrington, borough of the same name in Cheshire, England. The town sits on the banks of the River Mersey and was Historic counties of England, historically part of Lancashire. It is east o ...
, England, at Joseph Crosfield & Sons, Limited. It took only two years until the hardened fat could be successfully produced in the plant in Warrington, commencing production in late 1909. The initial year's production totalled nearly 3,000 tonnes. In 1909,
Procter & Gamble The Procter & Gamble Company (P&G) is an American multinational consumer goods corporation headquartered in Cincinnati, Ohio. It was founded in 1837 by William Procter and James Gamble. It specializes in a wide range of personal health/con ...
acquired the United States rights to the Normann patent; in 1911, they began marketing the first hydrogenated
shortening Shortening is any fat that is a solid at room temperature and is used to make crumbly pastry and other food products. The idea of shortening dates back to at least the 18th century, well before the invention of modern, shelf-stable vegetable ...
,
Crisco Crisco is an American brand of shortening that is produced by B%26G Foods. Introduced in June 1911 by Procter & Gamble, it was the first shortening to be made entirely of vegetable oil, originally cottonseed oil. Additional products marketed ...
(composed largely of partially hydrogenated
cottonseed oil Cottonseed oil is cooking oil from the seeds of cotton plants of various species, mainly ''Gossypium hirsutum'' and ''Gossypium herbaceum'', that are grown for cotton fiber, animal feed, and oil. cottonseed, Cotton seed has a similar structure to ...
). Further success came from the marketing technique of giving away free cookbooks in which every recipe called for Crisco. Before 1910, dietary fats in industrialized nations consisted mostly of
butterfat Butterfat or milkfat is the fatty portion of milk. Milk and cream are often sold according to the amount of butterfat they contain. Composition Butterfat is mainly composed of triglycerides. Each triglyceride contains three fatty acids. Butt ...
, beef
tallow Tallow is a rendered form of beef or mutton suet, primarily made up of triglycerides. In industry, tallow is not strictly defined as beef or mutton suet. In this context, tallow is animal fat that conforms to certain technical criteria, inc ...
, and
lard Lard is a Quasi-solid, semi-solid white fat product obtained by rendering (animal products), rendering the adipose tissue, fatty tissue of a domestic pig, pig.
. During Napoleon's reign in France in the early 19th century, a type of margarine was invented to feed troops using tallow and buttermilk. Soybeans began to be imported into the U.S. as a source of protein in the early 20th century, resulting in an abundance of soybean oil as a by-product that could be turned into a solid fat, thereby addressing a shortage of butterfat. With the advent of refrigeration, margarines based on hydrogenated fats presented the advantage that, unlike butter, they could be taken out of a refrigerator and immediately spread on bread. Some minor changes to the chemical composition of hydrogenated fats yielded superior baking properties compared to lard. As a result of these factors, margarine made from partially hydrogenated soybean oil began to replace butterfat. Partially hydrogenated fat such as Crisco and Spry, sold in England, began to replace butter and lard in baking bread, pies, cookies, and cakes in 1920. Production of partially hydrogenated fats increased steadily in the 20th century as processed vegetable fats replaced animal fats in the U.S. and other Western countries. At first, the argument was a financial one due to the lower costs of margarines and shortenings compared to lard and butter, particularly for restaurants and manufacturers. However, during the 1980s regulators, physicians, nutritionists, popular health media, educational curricula and cookbooks began to promote diets low in saturated fats for health reasons. Advocacy groups in the U.S. responded by demanding the replacement of saturated animal and tropical fats with vegetable alternatives. The Center for Science in the Public Interest (CSPI) campaigned vigorously against the use of saturated fats by corporations, including fast-food restaurants, endorsing trans fats as a healthier alternative. The National Heart Savers Association took out full page ads in major newspapers, attacking the use of
beef tallow Tallow is a rendered form of beef or mutton suet, primarily made up of triglycerides. In industry, tallow is not strictly defined as beef or mutton suet. In this context, tallow is animal fat that conforms to certain technical criteria, incl ...
in
McDonald's McDonald's Corporation, doing business as McDonald's, is an American Multinational corporation, multinational fast food chain store, chain. As of 2024, it is the second largest by number of locations in the world, behind only the Chinese ch ...
French fries. They urged multinational fast-food restaurants and food manufacturers to switch to vegetable oils, and almost all targeted firms responded by replacing saturated fats with trans fats. Since then the food industry has moved away from partially hydrogenated fats in response to the health concerns about trans fats, labeling requirements, and removal of trans fats from permitted food additives. They have been replaced with fully hydrogenated fats, vegetable oils that are naturally higher in saturated fat and therefore more solid at room temperature, such as
palm oil Palm oil is an edible vegetable oil derived from the mesocarp (reddish pulp) of the fruit of oil palms. The oil is used in food manufacturing, in beauty products, and as biofuel. Palm oil accounted for about 36% of global oils produced from o ...
and
coconut oil Coconut oil (or coconut fat) is an edible oil derived from the kernels, meat, and milk of the coconut palm fruit. Coconut oil is a white solid fat below around , and a clear thin liquid oil at higher temperatures. Unrefined varieties have a disti ...
, and
interesterified fat In the food industry and biochemistry, interesterification (IE) is a process that rearranges the fatty acids of a fat product, typically a mixture of triglycerides. The process implies breaking and reforming the ester bonds C–O–C that connec ...
s, which cannot result in the formation of trans fats.


Alternatives to hydrogenation

The negative public image and strict regulations has not led to substantial interest in replacing partial hydrogenation. In principle, the level of trans fat may be altered by modification of the catalysts and conditions of hydrogenation.


Issues

''Cis''–''trans'' isomerization of some of the remaining unsaturated carbon bonds to their
trans isomer Trans- is a Latin prefix meaning "across", "beyond", or "on the other side of". Used alone, trans may refer to: Sociology * Trans, a sociological term which may refer to: ** Transgender, people who identify themselves with a gender that dif ...
s during the partial hydrogenation process produces
trans fat Trans fat is a type of unsaturated fat that occurs in foods. Small amounts of trans fats occur naturally, but large amounts are found in some processed foods made with partially hydrogenated oils. Because consumption of trans fats is associated ...
, which can increase the risk cardiovascular problems. The conversion from cis to trans bonds is favored because the trans configuration has lower energy than the natural cis one. At equilibrium, the trans/cis isomer ratio is about 2:1.


See also

* Hydrotreated vegetable oil


References

Reprinted online:


External links

* {{Vascular diseases Edible oil chemistry