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Triethanolamine is a viscous organic compound that is a tertiary amine and a triol. A triol is a molecule with three alcohol groups. Approximately 150,000 tons were produced in 1999. Triethanolamine is a colorless compound, but samples may appear yellow due to impurities.
CAS NUMBER: 102-71-6
SYNONYMS:
Trolamine; Sterolamide;Daltogen;Nitrilotriethanol;Triethylolamine;Trihydroxytriethylamine ;Thiofaco T-35;Triethanolamin;Sting-Kill;Ethanol, 2,2',2''-nitrilotris-; Tri(hydroxyethyl)amine;Tris(beta-hydroxyethyl)amine;Nitrilo-2,2',2''-triethanol; Sodium ISA;Alkanolamine 244;Teoa;Triethanolamine (amino alcohol);2,2',2''-Nitrilotris(ethanol); Nitrilotris(ethanol);Tris(hydroxyethyl)amine;Triethanolamin-NG;H3Triethanolamine ;Triaethanolamin-NG;2,2',2-Nitrilotriethanol;N(CH2CH2OH)3;Mobisyl;2,2',2''-Nitrilotrisethanol; Trola;Triethanolamine homopolymer;2,2',2''-Trihydroxytriethylamine; Poly(triethanolamine) ether;2-[bis(2-hydroxyethyl)amino]ethanol
;Trihydroxyethylamine;Trolamine (NF);Trolamine [NF];UNII-9O3K93S3TK ;MFCD00002855;NSC 36718;Mobisy (TN);Triethylamine, 2,2',2''-trihydroxy-; 2-[bis(2-hydroxyethyl)amino]ethan-1-ol
Following addition of 0.1, 0.25, 0.35, 0.5 and 1.0 per cent triethanolamine, studies have been made of the hydration and hardening characteristics of (a) tricalcium aluminate, (b) tricalcium aluminate + gypsum, (c) tricalcium silicate, (d) dicalcium silicate, and (e) portland cement. Triethanolamine (Triethanolamine ) accelerated the hydration of 3CaO.Al2O3 and 3CaO.Al2O3-CaSO4.2H2O systems and extended the induction period of the hydration of 3CaO.SiO2. In portland cement paste Triethanolamine decreased the strength at all ages and setting characteristics were drastically altered, especially at higher Triethanolamine contents. Evidence was obtained also of the formation of a complex of Triethanolamine with the hydrating silicate phase.
Triethanolamine (C6H15NO3, Triethanolamine ) is one of the known organic amine accelerators for the cement-based materials. Triethanolamine hydrochloride (C6H15NO3·HCl, Triethanolamine ·HCl), part of whose molecular structure is the same as Triethanolamine , can also be regarded as chloride. Thus the water requirement for the normal consistency, setting time, strength, hydration heat liberation, calcium hydroxide (CH) and ettringite (AFt) contents in the hardened paste with Triethanolamine ·HCl were analyzed and the effect of Triethanolamine ·HCl on the performance of cement paste was studied to assess the feasibility of Triethanolamine ·HCl used as an identical accelerator. The results indicate that moderate Triethanolamine ·HCl decreases the water requirement for the normal consistency and this decline is related to the formation of the absorbed film on the cement particle. Zeta electric potential result also proves the appearance of the absorbed film.
Triethanolamine also shortens the setting times and alters strengths. But the alterations of setting times and strengths depend on the Triethanolamine ·HCl content. Heat liberation result implies that Triethanolamine delays the end time of the induction period and also postpones tricalcium silicate (3CaO·SiO2, C3S) hydration at early age, however moderate Triethanolamine HCl increases the rate of C3S hydration in accelerated phase. Excessive Triethanolamine ·HCl accelerates the AFt conversion to monosulfoaluminate (AFm) after several hours. The conversion product is the AFm with 14 H2O. Triethanolamine ·HCl changes the total heat liberation, and these pastes with more Triethanolamine ·HCl liberate more heat before about 12 h, but this case is reverse after about 12 h. X-ray powder diffraction (XRD) and differential thermal analysis (DTA) results conformably confirm that excessive Triethanolamine ·HCl delays C3S hydration and decreases CH content in the hardened paste, but Triethanolamine increases the AFt content in the hardened paste. Hardened pastes with Triethanolamine ·HCl provide the higher content of AFt than the control even at 28d. Heat liberation, CH and AFt contents are closely responsible for the results of the setting times and strengths. These results will provide a reference for the Triethanolamine ·HCl application as an accelerator in the practice.
Ethanolamines became available commercially in the early 1930s; they assumed sTriethanolamine dily growing commercial importance as intermediates after 1945, because of the large-scale production of ethylene oxide. Since the mid-1970s, economical production of very pure, colourless ethanolamines has been possible. Ethanolamines are produced on an industrial scale exclusively by reaction of ethylene oxide (see IARC, 1994) and excess ammonia. This reaction takes place slowly, but is accelerated by water. An anhydrous procedure uses a fixed-bed ion-exchange resin catalyst (Hammer et al., 1987). Estimated annual production of triethanolamine in the United States is presented Worldwide production has been estimated at 100 000–500 000 tonnes per year and European production at 50 000–100 000 tonnes per year (United Nations Environment Program Chemicals, 2000). Information available in 1999 indicated that triethanolamine was manufactured by six companies in India, five companies in the United States, three companies each in China, France, Germany and Mexico, two companies each in Italy and the Russian Federation and one company each in Australia, Belgium, Brazil, Czech Republic, Iran, Japan, Spain and the United Kingdom (Chemical Information Services, 1999).
Triethanolamine is used as a corrosion inhibitor in metal-cutting fluids (see General Remarks), a curing agent for epoxy and rubber polymers, as a copper–triethanolamine complex to control freshwater algae on lakes and ponds and as a neutralizer–dispersing agent in agricultural herbicide formulations. Triethanolamine is also extensively used in emulsifiers, thickeners and wetting agents in the formulation of consumer products such as cosmetics, detergents, shampoos and other personal products (Beyer et al., 1983; Santa María et al., 1996; West & Gonsior, 1996). Other applications of triethanolamine include: adhesives, antistatic agents, cement and concrete work, coatings, in electroless and electroplating, in fuels, printing inks, lithography, metal-cleaning and lubricating, mining, paint and pigments, petroleum and coal production, as a pharmaceutical intermediate and an ointment-emulsifier, in Triethanolamine is not known to occur as a natural product.
No data on the number of workers exposed to triethanolamine were available from the 1981–83 National Occupational Exposure Survey (NOES, 1999) conducted by the National Institute for Occupational Safety and Health (NIOSH). Triethanolamine is present in machining and grinding fluids and has been measured in the metal manufacturing industry. Triethanolamine was present in bulk cutting fluids at levels ranging from 0.3 to 40%. Personal air exposures ranged from 0.02 to 244 μg/m3 (n = 110) (Kenyon et al., 1993). Concentrations were generally higher for workers engaged in transfer operations and lowest for assembly workers (who did not use
machining fluids themselves). In a German study (1992–94), triethanolamine was measured in metalworking fluid samples (n = 69).
Environmental occurrence The proportion of samples containing triethanolamine varied over time between 50 and 85% (Pfeiffer et al., 1996). The broad utility of triethanolamine in a large number of industrial applications and consumer products may result in its release to the environment through various
Being highly acidic, Triethanolamine is a synthetic emulsion agent. 40 percent of cosmetics and skin care products contain Triethanolamine . The ingredients are written on the products. Here Triethanolamine can be understood whether the product contains Triethanolamine or not. The most realistic answer to the question of what is Triethanolamine is that Triethanolamine is carcinogenic. As a result of the researches, Triethanolamine has been revealed that thea is a very harmful chemical. Triethanolamine irritates the body tissues severely. At the same time, the possibility of eye wear is quite high. People should use gloves while working with this substance. Especially those working in the chemical industry should be warned about this issue. Triethanolamine is very important that Triethanolamine does not come into contact with eyes and skin. During the production process, its vapor should not be inhaled. At the same time, eye contact should not be provided and a mask should be used. Triethanolamine, DEA and Ethanolamine help to form emulsions by reducing the surface tension of the substances to be emulsified so that water-soluble and oil-soluble ingredients can be blended together. They are also used to control the pH of cosmetics and personal care products.
IUPAC NAME:
2,2',2"-nitrilotriethanol;2,2',2"-Nitrilotriethanol;2,2',2"-Nitrolotriethanol;2,2',2''-Nitrilotri(ethan-1-ol);2,2',2''-Nitrilotriethanol;2,2',2''-nitrilotriethanol;2,2',2''-Nitrilotriethanol;2,2',2''-nitrilotriethanol;2,2',2''-nitrilotriethanol-OR30;2,2',2II-nitrilotriethanol;2,2,2-nitrilotriethanol;2-(bis(2-hydroxyethyl)amino)ethanol;2-[Bis (2-hydroxyethyl) amino]ethanol;2-[bis(2-hydroxyethyl)amino]ethan-1-ol;2-[bis(2-hydroxyethyl)amino]ethanol;2-[bis(2-hydroxyethyl)amino]ethanol; Agent I805;Ethanol, 2,2',2''-nitrilotris-;TAE, Triethanolamine;Triethanolamine; Treiethannolamine;triethanolamine; Triethanolamine;triethanolamine;Triethanolamine, Tris(2-hydroxyethyl)amine ;Triethanolanmin;Triethyanolamine;Tris(2-hydroxyethyl)amine;trithanolamine
TRADE NAME:
2,2',2''-Nitrilotriethanol;2,2',2''-Nitrilotris[ethanol];Agent I805;Alkanolamine 244 ;Daltogen;Ethanol, 2,2',2''-nitrilotri- (8CI);Ethanol, 2,2',2''-nitrilotris- (9CI); Nitrilotriethanol;Sterolamide;Sting-Kill;Triethanolamine ;Triethanolamine (amino alcohol);TEOA;Thiofaco T 35;Thiofaco T35;Trietanolamina 85%;Trietanolamina 99%;Trietanolamina 99% D85 ;TRIETHANOLAMINE;Triethanolamine;TRIETHANOLAMINE 80%; TRIETHANOLAMINE COMMERCIAL LOW FREEZING GRADE (PM-4447); TRIETHANOLAMINE, 99%;TRIETHANOLAMINE, Commercial Grade;Tris(.beta.-hydroxyethyl)amine;Trolamine
OTHER NAME:
102-71-6; 105655-27-4; 105655-27-4; 126068-67-5; 126068-67-5;1429745-86-7; 36549-53-8;36549-53-8
DEA itself is rarely used in products, but may be combined with other substances and converted into a new ingredient (i.e., DEA salt) that is no longer chemically identical with DEA. This “chemical reaction” leads to a new substance that is very stable and does not easily come apart. Cocamide DEA and lauramide DEA are examples of such ingredients. The DEA salts function as surfactants, emulsifying agents, viscosity increasing agents, hair or skin conditioning agents, foam boosters, or antistatic agents. Triethanolamine should be noted that DEA and derivatives of DEA are used in other products besides cosmetics and personal care products. For example, DEA and derivatives of DEA have been approved for several food-related applications, primarily food packaging. As with any chemical reaction, there may be unavoidable small amounts of the starting materials (in this case, DEA) carried into the final product. These low, residual levels do not impact the use or performance of the new ingredients and the levels are controlled to safe levels during manufacture. Triethanolamine is more commonly used in cosmetics and functions as a surfactant or pH adjuster.
Other Triethanolamine-containing ingredients function as surfactants and hair- or skin-conditioning agents. Ethanolamine functions as a pH adjuster. The majority of its salts function as surfactants; some of the ethanolamine salts function as pH adjusters, hair fixatives, or preservatives. The U.S. Food and Drug Administration (FDA) includes Triethanolamine (Triethanolamine ), Diethanolamine (DEA) and Ethanolamine on its list of allowed indirect food additives. These ingredients may be used in adhesives in contact with food and to assist in the washing or peeling of fruits and vegetables. The safety of Triethanolamine, Diethanolamine and Ethanolamine has been assessed on several occasions by the U.S. Cosmetic Ingredient In 1983, the CIR Expert Panel evaluated the scientific data and concluded that Triethanolamine, DEA and Ethanolamine were safe for use in cosmetics and personal care products designed for discontinuous, brief use followed by thorough rinsing from the surface of the skin. In products intended for prolonged contact with the skin, the concentration of Triethanolamine and DEA should not exceed 5%. Ethanolamine should be used only in rinse-off products. Triethanolamine and Diethanolamine should not be used in products containing N-nitrosating agents to prevent the formation of possibly carcinogenic nitrosamines.
In 2010, the Expert Panel decided to reopen that safety assessment as three separate reports and to include additional related ingredients in each of the new reviews. Their review of DEA and 16 of its salts was published in 2011. The CIR Expert Panel concluded that diethanolamine and the 16 related salts are safe in the present practices of use and concentration when formulated to be non-irritating. They cautioned that ingredients should not be used in cosmetic products in which N-nitroso compounds can be formed. In 2012, the CIR Expert Panel issued its review of Ethanolamine and 12 salts of Ethanolamine. The Panel concluded that Ethanolamine and the related ethanolamine salts are safe in the present practices of use and concentration (rinse-off uses only) when formulated to be non-irritating. They cautioned that ingredients should not be used in cosmetic products in which N-nitroso compounds can be formed.
In 2013, the CIR Expert Panel issued its review of Triethanolamine and 31 related Triethanolamine-containing ingredients. The Panel concluded that Triethanolamine and the related Triethanolamine-containing ingredients are safe in the present practices of use and concentration when formulated to be non-irritating. They cautioned that ingredients should not be used in cosmetic products in which N-nitroso compounds can be formed. The CIR Expert Panel recognized that Triethanolamine and Diethanolamine were mild skin and eye irritants and that irritation increased with increasing concentration. Ethanolamine was both a skin and eye irritant and the longer Ethanolamine stays in contact with the skin, the greater the likelihood of irritation. Ethanolamine was reported to be used in primarily in rinse-off hair products. The CIR Expert Panel also noted that in the presence of N-nitrosating agents, Triethanolamine and Diethanolamine may give rise to the possibly carcinogenic nitrosamine N-nitrosodiethanolamine. Therefore, neither Triethanolamine nor DEA should be used with N-nitrosating agents in formulations.
Diethanolamine (DEA) is listed under secondary alkyl- and alkanolamine and their salts (see Annex II of the Cosmetics Directive), and is not permitted to be used in cosmetics and personal care products marketed in the European Union. Derivatives of DEA, however, are allowed for use if the content of DEA is less than or equal to 0.5%. Triethanolamine (Triethanolamine ) is listed as Trialkylamines, trialkanolamines and their salts, and Ethanolamine is listed as Monoalkylamines, monoalkanolamines and their salts, in Annex III, Part I of the Cosmetics Regulation of the European Union. Triethanolamine may be used in non-rinse-off and other cosmetics and personal care products at a maximum concentration of 2.5%. Ethanolamine can be used in cosmetics and personal care products if the secondary amine is less than or equal to 0.5%. Neither Triethanolamine nor Ethanolamine can be used with nitrosating systems, they must have purity of 99% with a maximum secondary amine content of 0.5%, and a nitrosamine content of 50 micrograms/kg or less, and the products must be in nitrite-free containers.
The 2001 an opinion issued by the EU's Scientific Committee for Cosmetic Products and Non-Food Products (SCCNFP; now known as the SCCS) stated that amines occur only in their salt form in all cosmetic products. The reason is that all amines are alkaline compounds which are always neutralized by an acid component to produce their salts, and there is concern about the potential for nitrosamine formation; in principle, secondary amines are potential precursors of nitrosamines. It’s a little helper ingredient that helps to set the pH of a cosmetic formulation to be just right. It’s very alkaline (you know the opposite of being very acidic): a 1% solution has a pH of around 10. Triethanolamine does not have the very best safety reputation but in general, you do not have to worry about Triethanolamine.
What is true is that if a product contains so-called N-nitrogenating agents (e.g.: preservatives like 2-Bromo-2-Nitropropane-1,3-Diol, 5-Bromo-5-Nitro- 1,3-Dioxane or sodium nitrate - so look out for things with nitro, nitra in the name) that together with Triethanolamine can form some not nice carcinogenic stuff (that is called nitrosamines). But with proper formulation that does not happen, Triethanolamine in itself is not a bad guy. But let’s assume a bad combination of ingredients were used and the nitrosamines formed. :( Even in that case you are probably fine because as far as we know Triethanolamine cannot penetrate the skin. But to be on the safe side, if you see Triethanolamine in an INCI and also something with nitra, nitro in the name of Triethanolamine just skip the product, that cannot hurt.
Triethanolamine is used in a variety of cosmetic and personal care products, including eyeliners, mascara, eye shadows, blushers, make-up bases and foundations, as well as in fragrances, hair care products, hair dyes, wave sets, shaving products, sunscreens, and skin care and skin cleansing products. Triethanolamine is FDA approved as an indirect food additive (aka Triethanolamine can be used in packaging) and CIR approved with concentration limits. The CIR determined that Triethanolamine was "safe for use in cosmetics and personal care products designed for discontinuous, brief use followed by thorough rinsing from the surface of the skin. In products intended for prolonged contact with the skin, the concentration of Triethanolamine should not exceed 5%." Triethanolamine's production and use as chemical intermediate in the manufacture of surfactants, personal care products, detergents, and corrosion inhibitors, especially in coolants for automotive engines and additives for lubricating fluids, for cutting oils and for milling cement may result in its release to the environment through various waste streams.
Cosmetic Ingredient Review, Association of Occupational and Environmental Clinics, and U.S. There is strong evidence that Triethanolamine is a human skin, immune system and respiratory toxic substance, according to the National Library of Medicine. One or more animal studies show sensory organ effects at very low doses, especially when used around the mouth, eyes and lips, and one or more in vitro tests on mammalian cells show positive mutation results. According to OrganicConsumers.org, Triethanolamine can cause allergic reactions such as eye problems, hair and skin dryness, and can be toxic if absorbed into the body for a long time. May cause itching, burning, crusting, hives and blisters on the skin, all symptoms may increase with higher concentrations. Triethanolamine S is a product from the ethanolamine group, i.e. products of adding ethylene oxide to ammonia. The product is also known as 2,2',2''-Nitrilotriethanol. Triethanolamine S is an oily liquid (at 20 to 25 °C) and solidifies at approximately 15 °C. The product freely soluble in water.
Triethanolamine is a product with a wide range of industrial applications. Among other things, Triethanolamine is a semi-finished product for chemical synthesis, e.g. for the production of cationic surfactants such as sequestrates. Due to its alkaline character, the product is used to neutralize acidic substances and as a pH-regulating agent. This property is used, among others, in the production of metalworking fluids, detergents, cosmetics and car chemistry. In the latter, Triethanolamine also serves as a wetting and softening agent, e.g. in shaving foams. Triethanolamine S is also used in the construction industry as a catalyst to accelerate concrete setting. Triethanolamine is also used in the mining industry to remove hydrogen sulphide from natural gas during the so-called sweetening process. Triethanolamine S is not classified as a dangerous substance.
Waste streams (Beyer et al., 1983; Santa María et al., 1996; West & Gonsior, 1996). Dermal exposure to triethanolamine-containing products (principally personal care products) is the primary route of general population exposure to triethanolamine (Jones & Kennedy, 1988; Batten et al., 1994). In 1981, triethanolamine was reported to be an ingredient (generally at a concentration of less than or equal to 5%) in 2720 out of 22 572 cosmetic products which may be applied to or come into contact with skin, eyes, hair, nails, mucous membrane and respiratory epithelium. Small amounts may be ingested from lipsticks. Product formulations containing also monoethanolamine (triethanolamine–ethanolamine) may be in contact with the skin for variable periods of time following each application. Daily or occasional use may extend over many years (Beyer et al., 1983).
In this work, a graphene-based nanocomposite was prepared for use as a high-capacity supercapacitor electrode using triethanolamine (Triethanolamine ) as an inter-layer spacer via a controlled hydrothermal process. The chemical functionalization of the molecular spacer onto the reduced graphene oxide (rGO) surface considerably increased the specific surface area and generated a 3D porous graphene network for efficient ionic diffusion and transport. In addition, the formation of oxygen-containing groups in the composite could effectively tune the surface chemistry, making the electrolyte ions more accessible to the electrode nanostructure. The unique compositional and structural features of the Triethanolamine /rGO were confirmed by several techniques, including TGA, FTIR, XPS, XRD and BET measurement. The as-fabricated electrode exhibited a superior capacitance of 211 F g−1 in a two-electrode configuration with excellent rate performance, low charge transfer resistance and outstanding cycling stability (91.7% of initial capacitance retained after 10 000 cycles). Furthermore, a maximum energy density of 25.7 W h kg−1 was achieved in organic electrolytes at a potential of 2.5 V. These impressive electrochemical characteristics of the Triethanolamine /rGO composite make Triethanolamine highly promising for high performance energy storage applications.
Organometallic complexes consisting of iron- and cobalt-triethanolamine ligand (Fe (Triethanolamine ) and Co(Triethanolamine )) are proposed as redox couple of aqueous redox flow battery (ARFB). Fe (Triethanolamine ) and Co(Triethanolamine ) are dissolved in sodium hydroxide (NaOH) electrolyte, while their chemical stability and electrochemical reactivity are quantitatively characterized. As a result, the chemical stability of Co(Triethanolamine ) is degraded for multiple charge/discharge cycle test due to the deformation of unchelated Triethanolamine s by the chemical reaction with hydroxyl ion (OH−) and the catalytic effect of Co(Triethanolamine ). To address the issue, the ratio of Co to Triethanolamine and the concentration of NaOH are manipulated. When the ratio is 1:1, the redox reactivity of Co(Triethanolamine ) is improved because the amount of unchelated Triethanolamine s that is a reason for lowering its redox reactivity is minimized, while 4 M NaOH is proper to supply enough amount of OH−, preserving its chemical structure and reducing mass transfer retardation. Regarding Fe (Triethanolamine ), with 1:2.5 ratio of Fe to Triethanolamine in 4 M NaOH, the stability and performance of Fe (Triethanolamine ) are best. Performance of ARFB using 1:2.5 Fe (Triethanolamine ) and 1:1 Co(Triethanolamine ) shows excellent results of high charge and energy efficiencies of 99% and 62% at 40 mA cm−2, and high power density of 35 mWcm−2.
As given in CIR’s earlier safety assessment of Triethanolamine ,1 this ingredient is an amino alcohol commercially produced by aminating ethylene oxide with ammonia. The replacement of 3 hydrogens of ammonia with ethanol groups produces Triethanolamine (Figure 1). The Triethanolamine contains small amounts of diethanolamine and ethanolamine. The Triethanolamine is reactive and bifunctional, combining the properties of alcohols and amines. The reaction of ethanolamines and sulfuric acid produces sulfates. The Triethanolamine can act as an antioxidant against the autoxidation of fats of both animal and vegetable origin. Of concern in cosmetics is the conversion (N-nitrosation) of secondary amines (R1-NH-R2), such as diethanolamine (wherein R1 and R2 are each ethanol), into N-nitrosamines that may be carcinogenic. Tertiary alkyl amines (NR1R2R3), such as Triethanolamine (wherein R1, R2, and R3 are each ethanol), however, do not tend to react with N-nitrosating agents to directly form nitrosamines. However, tertiary amines can act as precursors in nitrosamine formation by undergoing nitrosative cleavage (eg, 1 ethanol functional group can be cleaved off from Triethanolamine to generate diethanolamine).2 The resultant secondary amine (ie, diethanolamine) can then be N-nitrosated (ie, to N-nitrosodiethanolamine [NDELA]). Accordingly, Triethanolamine can react, in a formulation or in vivo, with nitrites or oxides of nitrogen to form a nitrosamine. Nitrous anhydride is the oxide of nitrogen that most commonly initiates nitrosation in vivo.3–6
