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Taurates

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Taurates (or taurides ) are a group of mild anionic surfactants . They are composed of a hydrophilic head group, consisting of N -methyltaurine (2-methylaminoethanesulfonic acid) and a lipophilic residue, consisting of a long-chain carboxylic acid (fatty acid), both linked via an amide bond. The fatty acids used could be lauric (C 12 ), myristic (C 14 ), palmitic (C 16 ) or stearic acid (C 18 ), but mainly mixtures of oleic acid (C 18:1 ) and coconut fatty acid (C 8 – C 18 ) are used. Besides sodium, no other counterions play a relevant role (these could be e. g. ammonium or other alkali or alkaline earth metals).

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25-580: The surfactant group of the taurates was developed by I.G. Farben in Germany (just like the isethionates ) and produced under the trade name Igepon at the Hoechst plant. Taurates rapidly spread due to their lime resistance and their oil-removing effect in textile treatment, as detergent raw material and in cosmetics applications. They had a breakthrough in particular because they do not felt wool during washing (as opposed to soap). The production of taurates decreased after

50-501: A 1985 article in The New York Times , tallow was also used for frying at Burger King , Wendy's , Hardee's , Arby's , Dairy Queen , Popeyes , and Bob's Big Boy . Tallow is, however, making a comeback in certain nutrition circles. Greaves (also graves ) or cracklings is the fibrous matter remaining from rendering, typically pressed into cakes and used for animal feed , especially for dogs and hogs, or as fish bait . In

75-474: A U.S. Air Force C-17 Globemaster III flew using JP-8 conventional jet fuel in three of its engines and a 50/50 blend of JP-8 and HRJ biofuel made from beef tallow in one engine on August 23, followed by a flight with the same 50/50 blend in all four engines on August 24. On August 27, it flew using a blend of 50% JP-8, 25% HRJ, and 25% coal -based fuel made through the Fischer–Tropsch process , becoming

100-621: A pleasant skin feel. They are non-toxic and readily biodegradable. However, in contrast to the taurides , they are not long-term stable outside a pH range of 5 to 8. Isethionates are used in solid soaps (so-called syndet bars) and in other personal care products such as lotions, washing and shower gels, shampoos, liquid soaps , shaving creams, and other cosmetic and dermatological preparations. Wilfried Umbach (Hrsg.), Kosmetik und Hygiene von Kopf bis Fuß , Wiley-VCH Verlag GmbH & Co. KGaA, 3. vollst. überarb. u. erw. Auflage (27. Juli 2012), ISBN   978-3-527-30996-2 Tallow Tallow

125-504: A strip of burning cloth in a saucer of tallow grease—was an accessible substitute. Such a candle was often simply called a "dip" or, because of its low cost, a "farthing dip" or "penny dip". Early in the development of steam-driven piston engines, the hot vapors and liquids washed away most lubricants very quickly. It was soon found that tallow was quite resistant to this washing. Tallow and compounds including tallow were widely used to lubricate locomotive and steamship engines at least until

150-414: A variable mixture of sodium salts of fatty acids , such as oleic and palmitic . Tallow is 100% fat , mainly of monounsaturated fats (52%) and saturated fats (42%), and contains no water, protein or carbohydrates (table). The fatty acid content of tallow is: Tallow is used mainly in producing soap and animal feed. A significant use of tallow is for the production of shortening . It

175-443: 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, including its melting point . Commercial tallow commonly contains fat derived from other animals, such as lard from pigs , or even from plant sources. The solid material remaining after rendering

200-476: Is also one of the main ingredients of the Native American food pemmican . With a smoke point of 480 °F (249 °C), tallow is traditionally used in deep frying and was preferred for this use until the rise in popularity of plant oils for frying. Before switching to pure vegetable oil in 1990, McDonald's cooked its French fries in a mixture of 93% beef tallow and 7% cottonseed oil . According to

225-477: Is as a lubricant for certain types of light engineering work, such as cutting threads on electrical conduit. Specialist cutting compounds are available, but tallow is a traditional lubricant that is easily available for cheap and infrequent use. The use of tallow or lard to lubricate rifles was the spark that started the Indian Mutiny of 1857 . To load the new Pattern 1853 Enfield Rifle , the sepoys had to bite

250-414: Is called cracklings , greaves, or graves. It has been used mostly for animal food , such as dog food . In the soap industry and among soap-making hobbyists , the name tallowate is used informally to refer to soaps made from tallow. Sodium tallowate , for example, is obtained by reacting tallow with sodium hydroxide (lye, caustic soda) or sodium carbonate (washing soda). It consists chiefly of

275-493: Is low (the LD 50 , rat, oral is 7800 mg·kg for cocoyl tauride). They are easily biodegradable, they are not prone to bioaccumulation , but they are harmful to aquatic organisms (like all surfactants ). Due to their amide bond , taurates are stable in a much wider pH range (about 2–10) than the corresponding esters , as for example isethionates. They are very mild surfactants with good foaming ability and high foam stability, even in

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300-423: Is still used as a patch or projectile lubricant in present-day black powder arms. Tallow is used to make a biodegradable motor oil. Tallow is also used in traditional bell foundry , as a separation for the false bell when casting . Tallow can be used as flux for soldering . Mutton tallow is widely used as starch, lubricant and softener in textile manufacturing. Pretreatment processes in textiles include

325-461: Is therefore complicated and expensive. An advantage of the Schotten-Baumann method, however, is the very low content of free fatty acids in the end product. Taurates are also accessible by direct amidation of N -methyltaurine or its sodium salt with the corresponding fatty acid for 10 hours at 220 °C under nitrogen. The excess fatty acid (added for a favorable equilibrium) usually remain in

350-400: The taurides , isethionates are a class of particularly mild anionic surfactants which, unlike ordinary soaps , retain their washing-active properties even in hard water. Isethionates are obtained on an industrial scale reacting mixtures of carboxylic acids with salts of isethionic acid under acidic catalysis e. g. with methanesulfonic acid . The mixtures of carboxylic acids are obtained from

375-514: The 1950s. (During World War II, the vast fleets of steam-powered ships exhausted the supply, leading to the large-scale planting of rapeseed because rapeseed oil also resisted the washing effect.) Tallow is still used in the steel rolling industry to provide the required lubrication as the sheet steel is compressed through the steel rollers . There is a trend toward replacing tallow-based lubrication with synthetic oils in rolling applications for surface cleanliness reasons. Another industrial use

400-521: The United Kingdom were found to be affected, leading to objections from vegans and members of some religious communities. Tallow once was widely used to make molded candles before more convenient wax varieties became available—and for some time after since they continued to be a cheaper alternative. For those too poor even to avail themselves of homemade, molded tallow candles, the "tallow dip"—a reed that had been dipped in melted tallow or sometimes

425-498: The cartridge open. It was believed that the paper cartridges that were standard issue with the rifle were greased with lard (pork fat), which was regarded as unclean by Muslims , or tallow (cow fat), which is incompatible with Hindu dietary laws . Tallow, along with beeswax , was also used in the lubricant for American Civil War ammunition used in the Springfield rifled musket . A combination of mutton tallow, paraffin wax and beeswax

450-542: The first United States Department of Defense aircraft to fly on such a blend and the first aircraft to operate from Edwards using a fuel derived from beef tallow. Tallow also has a use in printmaking, where it is combined with bitumen and applied to metal print plates to resist acid etching. The use of trace amounts of tallow as an additive to the substrate used in polymer banknotes came to light in November 2016. Notes issued in 24 countries including Canada, Australia, and

475-464: The hydrolysis of animal fats ( tallow ) or vegetable oils, preferably coconut oil , but also palm oil , soybean oil or castor oil . Isethionates are solids which are often mixed with fatty acids (up to 30% by weight) to lower their freezing point. Despite its low water solubility (100ppm at 25 °C), the lower-priced sodium cocoylisethionate has found more widespread use than its well water-soluble ammonium salt (> 25 wt.% at 25 °C). To solubilize

500-515: The outbreak of the World War II , since only poor quality fatty acids were available due to the fat management. Taurates were first obtained by the Schotten-Baumann method which is the reaction of long-chain carboxylic acid chlorides with aqueous solutions of the sodium salt of N -methyltaurine. The formation of (at least) equimolar amounts of sodium chloride is problematic, as they worsen

525-400: The past, it has been both favored and shunned in dog food . Tallow can be used for the production of biodiesel in much the same way as oils from plants are currently used. The United States Air Force has experimented successfully with the use of beef tallow in aviation biofuels . During five days of flight testing from August 23 to 27, 2010, at Edwards Air Force Base , California ,

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550-919: The presence of fats and oils. Taurates retain their good washing properties even in hard water or seawater . Taurates are suitable in concentrations of about 2% as co-surfactants because of their good compatibility with all nonionic and anionic surfactants. Taurates are used as mild, well-foaming surfactants in body cleansing and personal care products ( shampoos , liquid soaps and cleansers, face lotions, skin creams, bubble baths, syndet soaps), textile processing (wetting agents and detergents, dye dispersants), in crop protection formulations and in other industrial applications. Isethionates Isethionates are esters of long-chain aliphatic carboxylic acids (C 8 – C 18 ) with isethionic acid (2-hydroxyethanesulfonic acid) or salts thereof, such as ammonium isethionate or sodium isethionate. They are also referred to as acyl isethionates or acyloxyethanesulfonates. Like

575-545: The product, which can interfere with some applications. The decomposition of N -methyltaurine already begins At temperatures above 200 °C and the resulting taurates darken and develop an unpleasant smell. Therefore, more recent variants of the direct amidation aim at gentler process conditions using suitable catalysts, such as sodium borohydride , boric acid or zinc oxide . At room temperature, taurates are usually pasty masses, which dissolve well in water and react then neutral to slightly alkaline ( pH 7–8). Their toxicity

600-436: The properties of surfactant mixtures with such taurates. The high salt content also makes the resulting taurates hygroscopic and corrosive. Another disadvantage of the Schotten-Baumann method is the hazardousness of the raw materials (such as phosphorus trichloride ) and the intermediates (the acyl chlorides ) and the accumulation of large amounts of waste materials, such as phosphonic acids . This synthesis pathway for taurates

625-422: The sparsely soluble isethionates and taurides, the formation of mixtures with amphoteric surfactants (such as cocamidopropyl betaine ) are proposed. From such mixtures, it is possible to prepare liquid, clear and transparent aqueous concentrates which are liquid at room temperature. Isethionates are characterized by excellent skin compatibility, excellent foaming (even in hard water), good cleansing properties and

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