Amine oxides Manufacture

TOMAH AO-728 Special is a high foaming 50% active amine oxide. It is a very effective foam booster/stabilizer in liquid detergent formulations. It is an economical replacement for lauryl dimethyl amine oxide and many alkanolamldes. TOMAH AO-728 Special is manufactured from an ethoxylated tertiary amine. These amine oxides are generally considered to be milder to skin and eyes than amine oxides manufactured from methyl tertiary amines. 

Amine Guard, 4 813 Amine hydrates, 14 171 Amine oxides, 2 463-476 as cellulose solvents, 11 266 chemical reactions, 2 466-469 commercial, 2 464t economic aspects, 2 471 health and safety factors, 2 472 manufacturing and porcessing, 2 469-471... 

Fatty Amines. Fatty amines are the most important nitrogen derivatives of fatty acids. They are produced by the reaction of fatty acids with ammonia and hydrogen. They are the bases for the manufacture of quaternary ammonium compounds used as fabric softeners and biocides. Fatty amine oxides are mild to the skin with good cleaning and foaming properties and find application as a shampoo ingredient. The above mentioned products are but some of the oleochemical derivatives from coconut fatty acids (5). 

The asymmetrical tertiary amines are used exclusively as starting materials for the manufacture of quaternary ammonium compounds, cationic and amphoteric surfactants, and amine oxides. Quaternary ammonium compounds used as bactericides and algicides are produced by the reaction of tertiary amines with benzyl chloride, methyl chloride, or dimethyl sulfate. Of these, the benzyl ammonium chloride salt is the most widely used. 

Tertiary amines are also used in the manufacture of amine oxides by the oxidation with hydrogen peroxide. The amine oxides are used in cosmetic preparations for its good foaming properties and mildness to the skin. Another raw material used in the cosmetic industry is the betaines produced by the reaction of a tertiary fatty amine with sodium chloroacetate. The betaines exhibit good foam stability over a wide range of pH, are insensitive to water hardness, and are mild to the skin (33). 

Ozone is being promoted for use in the conversion of tertiary amines to amine oxides, of a-pinene to pinonic and pinic acids, of olefins to ozonides and these in turn to aldehydes and oxy-peroxides, of sulfides to sulfoxides and sulfones, and of various other organic substances. Such reactions are of practical interest in drug manufacture, and several drug companies are now commercially using ozone in their manufacturing operations, specifically in oxidation of sterols in hormone syntheses. 

Amine oxides of the same kind are manufactured by reaction of alkanoic acids and their esters with N,N-dimethyl-l,3-propanediamine and subsequent oxidation of the amino amide by hydrogen peroxide [9] ... 

This is not to say that surfactants or surfactant-like compounds are absolutely risk-free. However, the risk, in some cases, is from the contaminants that may accompany the surfactants, rather than from the surfactants themselves. An example of this was seen a few years ago in the concern over nitrosamine contamination of amine oxide surfactants, either from their manufacture or from the circumstances of their formulation. For example ... 

In addition to low-cloud point nonionics, the patent literature describes the use of some additional surfactants in ADDs. The use of a mixture of high- and low-cloud point surfactants is reported to provide benefit in terms of greasy soil cleaning. Low-cloud point nonionics are also used in combination with charged surfactants (anionic, zwitterionic) for removal of greasy soil such as lipstick. Examples include amine oxide, alkyl carboxy ethoxylate, or sulfobetaine. For automatic dishwashing tablets, the use of disulfonated anionics such as Dowfax 3B-2 or 2A-1 manufactured by Dow Chemicals has been reported to decrease the solubility rate and the friability percentage loss. ... 

Aliphatic tertiary amines can be oxidised to A-oxides using 35% w/w H2O2 alone [149], typically in water at 1.1 1.0 molar ratio for 4-5 hours at 60-65°C (example for dodecyldimethylamine). This reaction is employed worldwide on a scale in excess of 25 ktpa, to make fatty amine oxides, which are used as surfactants [150] in personal care products (e.g. shampoos) and as thickener components in hypochlorite household bleach. N-Methylmorpholine A-oxide has a growing use as a solvent for cellulose in the manufacture of a new cellulose fibre [151]. Substituted oxazolidine N-oxides are relatively new user-friendly biocides [152]. A further application involving an aliphatic tertiary amine oxide intermediate is glyphosate manufacture (section 9.5.1.7.6). 

Lonza offers a variety of biodegradable cosmetic grade amine oxides including alkyl dimethyl amine oxides and alkyl amido amine oxides. These compounds are manufactured under the BARLOX trade name from Lonza s own production of BARLENE Tertiary Amines and Alkyl Amido Amines. The BARLOX Amine Oxides find application for their foam stability and viscosity building in Personal Care and Industrial products. They possess broad acld/alkallne stability and are also used as specialty emulsifiers and conditioning agents. 

Lyocell is a cellulosic fibre derived from wood pulp produced from sustainable managed forests. The wood pulp is dissolved in a solution of an amine oxide (usually A-methylmorpholine-A-oxide (5.1)). The solution is spun into fibres and the solvent extracted as the fibres pass through a washing process. The manufacturing process recovers >99.5% of the solvent. The solvent itself is non-toxic and all the effluent produced is non-hazardous. 

Tertiary amines are also the starting material for the manufacture of quaternaries, amine oxides and alkyl betaines. Salts of amines, together with other surfactants, are used in cosmetics. Their usage is restricted to specialties they exhibit conditioning and antistatic properties in hair care applications. 

An example along the above lines may be the new solvent-spun fiber Tencel, by Courtaulds, which recently was introduced. It is claimed to have an environmentally clean process, with virtually total recycling of the solvent." The manufacturing process is said to involve the dissolving of pulp in hot amine oxide, filtration of the solution, and then spinning into a bath containing a dilute solution of the solvent. The bath removes the amine oxide from the fibers, which are washed and dried, and the removed solvent is reclaimed for further use. The final fiber is said to have a different molecular structure from that of normal rayon, and a smooth surface and a round cross section. The fiber is claimed to be stronger than cotton and normal rayon in both the dry and the wet states. 

Amine oxides are manufactured by the hydrogen peroxide oxidation of tertiary amines. The hydrogen peroxide is typically supplied in 35-70% aqueous solution and the reaction is conducted in a water miscible solvent such as isopropanol, ethanol or propylene glycol. Due to the low solubility of the higher alkylamines in water, amine oxide solutions are often quite low in actives content, 25-40%. Amine oxides are thermally unstable, degrading via the Cope reaction at temperatures above 120 °C and by reversion to amine at slightly lower temperatures. The reactions are therefore often catalysed to lower the reaction temperature and time. Carbon dioxide is the most common catalyst but carbon dioxide liberating salts such as ammonium bicarbonate or sodium bicarbonate are also used [30-34]. 

CCls CHO. A colourless oily liquid with a pungent odour b.p. 98°C. Manut actured by the action of chlorine on ethanol it is also made by the chlorination of ethanal. When allowed to stand, it changes slowly to a white solid. Addition compounds are formed with water see chloral hydrate), ammonia, sodium hydrogen sulphite, alcohols, and some amines and amides. Oxidized by nitric acid to tri-chloroethanoic acid. Decomposed by alkalis to chloroform and a methanoate a convenient method of obtaining pure CHCI3. It is used for the manufacture of DDT. It is also used as a hypnotic. 

CH3CH2OHCH3. B.p. 82 C. Manufactured by hydrolysis of propene. Used in the production of acetone (propanone) by oxidation, for the preparation of esters (e.g. the ethanoate used as a solvent), amines (diisopropylamines, etc.), glycerol, hydrogen peroxide. The alcohol is used as an important solvent for many resins, aerosols, anti-freezes. U.S. production 1978 775 000 tonnes. 

Three generations of latices as characterized by the type of surfactant used in manufacture have been defined (53). The first generation includes latices made with conventional (/) anionic surfactants like fatty acid soaps, alkyl carboxylates, alkyl sulfates, and alkyl sulfonates (54) (2) nonionic surfactants like poly(ethylene oxide) or poly(vinyl alcohol) used to improve freeze—thaw and shear stabiUty and (J) cationic surfactants like amines, nitriles, and other nitrogen bases, rarely used because of incompatibiUty problems. Portiand cement latex modifiers are one example where cationic surfactants are used. Anionic surfactants yield smaller particles than nonionic surfactants (55). Often a combination of anionic surfactants or anionic and nonionic surfactants are used to provide improved stabiUty. The stabilizing abiUty of anionic fatty acid soaps diminishes at lower pH as the soaps revert to their acids. First-generation latices also suffer from the presence of soap on the polymer particles at the end of the polymerization. Steam and vacuum stripping methods are often used to remove the soap and unreacted monomer from the final product (56). 

Maleic Anhydride. The ACGIH threshold limit value in air for maleic anhydride is 0.25 ppm and the OSHA permissible exposure level (PEL) is also 0.25 ppm (181). Maleic anhydride is a corrosive irritant to eyes, skin, and mucous membranes. Pulmonary edema (collection of fluid in the lungs) can result from airborne exposure. Skin contact should be avoided by the use of mbber gloves. Dust respirators should be used when maleic anhydride dust is present. Maleic anhydride is combustible when exposed to heat or flame and can react vigorously on contact with oxidizers. The material reacts exothermically with water or steam. Violent decompositions of maleic anhydride can be catalyzed at high temperature by strong bases (sodium hydroxide, potassium hydroxide, calcium hydroxide, alkaU metals, and amines). Precaution should be taken during the manufacture and use of maleic anhydride to minimize the presence of basic materials. 

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