fat hydrogenation

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.

File:FatHydrogenation.svg is a trans fat with negative health effects.]]

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.Ian P. Freeman "Margarines and Shortenings" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a16_145}}

Cis–trans isomerization of some of the remaining unsaturated carbon bonds to their trans isomers during the partial hydrogenation process produces trans fat, which has been demonstrated to have cardiovascular health risk.{{cite journal | last1 = Teresa Tarrago-Trani | first1 = Maria | last2 = Phillips | first2 = Katherine M. | last3 = Lemar | first3 = Linda E. | last4 = Holden | first4 = Joanne M. | year = 2006 | title = New and Existing Oils and Fats Used in Products with Reduced Trans-Fatty Acid Content | url = https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/JADA106_867-880.pdf| journal = Journal of the American Dietetic Association | volume = 106 | issue = 6| pages = 867–880 | doi = 10.1016/j.jada.2006.03.010 | pmid = 16720128 }} The conversion from cis to trans bonds is chemically favored because the trans configuration has lower energy than the natural cis one. At equilibrium, the trans/cis isomer ratio is about 2:1.

Numerous studies have concluded that these trans fatty acids have negative health effects. As a result, many countries have enacted trans fat regulation that aims to eliminate or severely restrict their amount in industrialized food products, such as mandatory labeling of trans fats on food products.{{cite news|url=https://www.independent.co.uk/life-style/health-and-wellbeing/healthy-living/deadly-fats-why-are-we-still-eating-them-843400.html|title=Deadly fats: why are we still eating them?|date=2008-06-10|work=The Independent|access-date=2008-06-16|url-status=live|archive-url=https://web.archive.org/web/20080614071803/http://www.independent.co.uk/life-style/health-and-wellbeing/healthy-living/deadly-fats-why-are-we-still-eating-them-843400.html|archive-date=2008-06-14}}{{cite news|url=http://www.nbcnews.com/id/16051436|archive-url=https://web.archive.org/web/20130213023223/http://www.nbcnews.com/id/16051436/|url-status=dead|archive-date=February 13, 2013|title=New York City passes trans fat ban|date=2006-12-05|work=NBC News|access-date=2010-01-09}} The United States Food and Drug Administration has concluded that partially hydrogenated oils are not generally recognized as safe, and since 2018 categorizes them as food additives, not food.{{cite news|url=https://www.nytimes.com/2015/06/17/health/fda-gives-food-industry-three-years-eliminate-trans-fats.html|title=F.D.A. Gives Food Industry 3 Years to Eliminate Trans Fats|date=2015-06-16|work=The New York Times|access-date=2015-06-16|url-status=live|archive-url=https://web.archive.org/web/20150616164203/http://www.nytimes.com/2015/06/17/health/fda-gives-food-industry-three-years-eliminate-trans-fats.html|archive-date=2015-06-16}}

A number of old and new ingredients are available to replace partially-hydrogenated oil with significant levels of trans fat.{{cite journal | last1 = Teresa Tarrago-Trani | first1 = Maria | last2 = Phillips | first2 = Katherine M. | last3 = Lemar | first3 = Linda E. | last4 = Holden | first4 = Joanne M. | year = 2006 | title = New and Existing Oils and Fats Used in Products with Reduced Trans-Fatty Acid Content | url = https://www.ars.usda.gov/ARSUserFiles/80400525/Articles/JADA106_867-880.pdf| journal = Journal of the American Dietetic Association | volume = 106 | issue = 6| pages = 867–880 | doi = 10.1016/j.jada.2006.03.010 | pmid = 16720128 }}

• Improved hydrogenation processes can produce partially-hydrogenated oil with much lower amounts of trans fat.
• Oils rich in monounsaturated fatty acids (especially oleic acid) obtained from plant breeding have higher stability compared to their polyunsaturated-rich ancestors, offering a similar improvement to shelf life.
• Tropical oils (palm oil, palm kernel oil, coconut oil) are naturally rich in saturated fat. They can be further fractionated to increase the concentration of desired fatty acids.
• Interesterification can be used to mix multiple types of fats, obtaining an oil with intermediate properties. For example, soybean oil and fully-hydrogenated soybean oil can be interesterified to obtain a semi-hard oil.

Many health organizations recommend limiting or replacing dietary intake of trans fats and saturated fats, in favor of unsaturated fats.the American Heart Association,{{Cite journal |vauthors=Sacks FM, Lichtenstein AH, Wu JH, Appel LJ, Creager MA, Kris-Etherton PM, Miller M, Rimm EB, Rudel LL, Robinson JG, Stone NJ, Van Horn LV |date=July 2017 |title=Dietary Fats and Cardiovascular Disease: A Presidential Advisory From the American Heart Association |journal=Circulation |volume=136 |issue=3 |pages=e1–e23 |doi=10.1161/CIR.0000000000000510 |pmid=28620111|s2cid=367602 |doi-access=free }}the World Health Organization, Health Canada,{{cite web | url = https://food-guide.canada.ca/en/healthy-eating-recommendations/make-it-a-habit-to-eat-vegetables-fruit-whole-grains-and-protein-foods/choosing-foods-with-healthy-fats/ | title = Choosing foods with healthy fats | publisher = Health Canada | access-date = 2019-09-24| date = 2018-10-10 }}, the US Department of Health and Human Services,{{cite web | url = https://health.gov/dietaryguidelines/2015/resources/DGA_Cut-Down-On-Saturated-Fats.pdf | title = Cut Down on Saturated Fats | publisher = United States Department of Health and Human Services | access-date = 2019-09-24}} the UK National Health Service,{{cite web | url = https://www.nhs.uk/live-well/eat-well/different-fats-nutrition/ | title = Fat: the facts | publisher = United Kingdom's National Health Service | access-date = 2019-09-24| date = 2018-04-27 }} the UK Scientific Advisory Committee on Nutrition [https://assets.publishing.service.gov.uk/government/uploads/system/uploads/attachment_data/file/814995/SACN_report_on_saturated_fat_and_health.pdf "Saturated Fats and Health"]. Scientific Advisory Committee on Nutrition (SACN). Retrieved 26 July 2021], the Australian Department of Health and Aging,{{cite web | url = https://www.eatforhealth.gov.au/food-essentials/fat-salt-sugars-and-alcohol/fat | title = Fat | publisher = Australia's National Health and Medical Research Council and Department of Health and Ageing | access-date = 2019-09-24| date = 2012-09-24 }} the Singapore Ministry of Health,{{cite web | url = https://www.healthhub.sg/live-healthy/458/Getting%20the%20Fats%20Right | title = Getting the Fats Right! | publisher = Singapore's Ministry of Health | access-date = 2019-09-24}} the Indian Ministry of Health and Family Welfare,{{cite web | url = https://www.nhp.gov.in/healthlyliving/healthy-diet | title = Health Diet | publisher = India's Ministry of Health and Family Welfare | access-date = 2019-09-24}} the New Zealand Ministry of Health,{{cite web |url=https://www.health.govt.nz/your-health/healthy-living/food-activity-and-sleep/healthy-eating/making-healthier-food-choices | title = Making healthier food choices | publisher = New Zealand's Ministry of Health | access-date = 2021-06-03}} and Hong Kong's Department of Health.{{cite web | url = https://www.chp.gov.hk/en/static/100023.html | title = Know More about Fat | publisher = Hong Kong's Department of Health | access-date = 2019-09-24}}

File:Wilhelm Normann.jpg patented the hydrogenation of liquid oils in 1902]]

File:Crisco Cookbook 1912.jpg

Nobel Prize laureate Paul Sabatier worked in the late 1890s to develop the chemistry of hydrogenation. Whereas Sabatier considered hydrogenation of only vapors, the German chemist Wilhelm Normann showed in 1901 that liquid oils could be hydrogenated, and patented the process in 1902.{{patent|de|141029|Process for converting unsaturated fatty acids or their glycerides into saturated compounds}}{{patent|gb|190301515|Process for converting unsaturated fatty acids or their glycerides into saturated compounds}}{{cite journal| vauthors = Patterson HB |title=Hydrogenation |journal=Sci Lecture Papers Series |year=1998 |url=http://www.soci.org/SCI/publications/2001/pdf/pb97.pdf |access-date=7 January 2007 |archive-url=https://web.archive.org/web/20070926141346/http://www.soci.org/SCI/publications/2001/pdf/pb97.pdf |archive-date=26 September 2007}} Normann's hydrogenation process made it possible to stabilize affordable whale oil or fish oil 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 company. At the same time, the invention was extended to a large-scale plant in Warrington, 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.{{cite web|url=http://www.dgfett.de/history/normann/nr_fiedler.htm|title=Wilhelm Normann und die Geschichte der Fetthärtung von Martin Fiedler, 2001|date=20 December 2011|access-date=14 August 2007|archive-url=https://web.archive.org/web/20111001212626/http://www.dgfett.de/history/normann/nr_fiedler.htm|archive-date=1 October 2011|df=dmy-all}} In 1909, Procter & Gamble acquired the United States rights to the Normann patent;{{cite web| last1=Shurtleff|first1=William|last2=Aoyagi|first2=Akiko|title=History of Soybeans and Soyfoods: 1100 B.C. to the 1980s|archive-url=https://web.archive.org/web/20051018105337/http://www.thesoydailyclub.com/SFC/MSPproducts501.asp|url=http://www.thesoydailyclub.com/SFC/MSPproducts501.asp| url-status=usurped|archive-date=18 October 2005}} in 1911, they began marketing the first hydrogenated shortening, Crisco (composed largely of partially hydrogenated cottonseed oil). 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, beef tallow, and lard. 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.{{cite book | first = Fred A. | last = Kummerow |title=Cholesterol Won't Kill You – But Trans Fat Could|publisher=Trafford Publishing|year=2008|isbn=978-1-4251-3808-0}}

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 in McDonald's 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.{{cite journal | vauthors = Schleifer D | title = The perfect solution: How trans fats became the healthy replacement for saturated fats | journal = Technology and Culture | volume = 53 | issue = 1 | pages = 94–119 | date = January 2012 | doi = 10.1353/tech.2012.0018 | jstor = 41475458 | pmid = 22530389 | s2cid = 26343964 }}{{cite journal|vauthors=Henderson GD |title= Re: The scientific report guiding the US dietary guidelines: is it scientific?|journal=BMJ|year=2015|volume=351|pages=h4962|doi=10.1136/bmj.h4962|pmid= 26400973|s2cid= 42013152|url=https://www.bmj.com/content/351/bmj.h4962/rr-3|access-date=22 July 2023|doi-access=free}}{{cite web | author=Mary G. Enig | title=The Tragic Legacy of Center for Science in the Public Interest (CSPI) | url=https://www.westonaprice.org/health-topics/know-your-fats/the-tragic-legacy-of-center-for-science-in-the-public-interest-cspi/ | access-date=22 July 2023}}

In the early 20th century, soybeans began to be imported into the United States as a source of protein; large quantities of soybean oil were a by-product. At the same time, there was not enough butterfat available for consumers. Margarine manufacturers found that hydrogenated fats worked better than the previously used combination of animal and liquid vegetable fats. Margarine made from hydrogenated soybean oil and vegetable shortenings such as Crisco and Spry, sold in England, began to replace butter and lard in baking bread, pies, cookies, and cakes by 1920.

Production of hydrogenated fats increased steadily until the 1960s, as processed vegetable fats replaced animal fats in the United States and other Western countries. At first, the argument was a financial one due to lower costs; advocates also said that the hydrogenated fats of margarine were healthier than the saturated fats of butter.

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.{{cite web |title=Ask the Experts: Hydrogenated Oils |url=http://www.berkeleywellness.com/healthy-eating/food/article/hydrogenated-oils |website=Berkeley Wellness |publisher=Remedy Health Media |access-date=24 November 2018 |date=October 1, 2011}}{{cite web |last1=Collette |first1=Robert L. |title=Why a Monograph for Fully Hydrogenated Oils and Fats is Needed |url=https://qualitymatters.usp.org/why-monograph-fully-hydrogenated-oils-and-fats-needed |website=Quality Matters |publisher=United States Pharmacopeial Convention |access-date=24 November 2018 |date=July 7, 2015}}{{cite web |last1=Haynes |first1=Fiona |title=Partially vs. Fully Hydrogenated Oils: The Truth About Trans Fats |url=https://www.thespruceeats.com/do-hydrogenated-oils-contain-trans-fats-2246050 |website=The Spruce Eats |publisher=Dotdash |access-date=24 November 2018 |date=September 23, 2018}} 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 and coconut oil, and interesterified fats, which cannot result in the formation of trans fats.

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.

• Hydrotreated vegetable oil

{{cite book | title=Nobel Lectures, Chemistry, 1901–1921 | year=1966 | publisher=Elsevier}} Reprinted online: {{cite web | title=Paul Sabatier, The Nobel Prize in Chemistry 1912 | publisher=Nobel Foundation | url=http://nobelprize.org/nobel_prizes/chemistry/laureates/1912/sabatier-bio.html | access-date=7 January 2007}}

{{patent | de | 141029 | Process for converting unsaturated fatty acids or their glycerides into saturated compounds}}

{{patent | gb | 190301515 | Process for converting unsaturated fatty acids or their glycerides into saturated compounds}}

{{cite journal | vauthors = Patterson HB | title=Hydrogenation | journal=Sci Lecture Papers Series | year=1998 | url=http://www.soci.org/SCI/publications/2001/pdf/pb97.pdf | access-date=7 January 2007 | url-status=dead | archive-url=https://web.archive.org/web/20070926141346/http://www.soci.org/SCI/publications/2001/pdf/pb97.pdf | archive-date=26 September 2007}}

{{cite web | url=http://www.dgfett.de/history/normann/nr_fiedler.htm | title=Wilhelm Normann und die Geschichte der Fetthärtung von Martin Fiedler, 2001 | date=20 December 2011 | access-date=14 August 2007 | archive-url=https://web.archive.org/web/20111001212626/http://www.dgfett.de/history/normann/nr_fiedler.htm | archive-date=1 October 2011 | url-status=dead | df=dmy-all}}

{{cite journal | vauthors=Ascherio A, Stampfer MJ, Willett WC | title=Trans fatty acids and coronary heart disease | journal=The New England Journal of Medicine | year=1999 | volume=340 | issue=25 | pages=1994–8 | doi=10.1056/NEJM199906243402511 | pmid=10379026 | url=http://www.hsph.harvard.edu/reviews/transfats.html | access-date=14 September 2006 | archive-url=https://web.archive.org/web/20060903061226/http://www.hsph.harvard.edu/reviews/transfats.html | archive-date=3 September 2006}}

{{cite book | first = Fred A. | last = Kummerow | name-list-style = vanc | title=Cholesterol Won't Kill You – But Trans Fat Could | publisher=Trafford Publishing | year=2008 | isbn=978-1-4251-3808-0}} NOTE: Unreliable source.

• {{cite book |last1=Shurtleff |first1=William |last2=Aoyagi |first2=Akiko |title=History of Hydrogenation, Shortening and Margarine (1860-2020): Extensively Annotated Bibliography and Sourcebook |date=2020 |publisher=Soyinfo Center |location=Lafayette, CA |isbn=9781948436182 |url=https://www.soyinfocenter.com/pdf/227/Hydr.pdf}}

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Category:Edible oil chemistry