Diethanolamine formation

Hlkanolamides. The fatty acid alkanolamides are used widely ia shampoo formulations as viscosity and lather builders. They are formed by the condensation of a fatty acid with a primary or secondary alkanolamine. The early amides were compositions of 2 1 alkanolamine to fatty acid. Available technology allows the formation of amides with a 1 1 ratio of these additives. These amides are classified as superamide types. The typical amide used ia shampoo preparations usually contains the mono- or diethanolamine adduct, eg, lauric diethanolamide [120-40-1] (see Amides, fatty acid). 

Activated tertiary amines such as triethanolamine (TEA) and methyl diethanolamine (MDEA) have gained wide acceptance for CO2 removal. These materials require very low regeneration energy because of weak CO2 amine adduct formation, and do not form carbamates or other corrosive compounds (53). Hybrid CO2 removal systems, such as MDEA —sulfolane—water and DIPA—sulfolane—water, where DIPA is diisopropylamine, are aqueous alkaline solutions in a nonaqueous solvent, and are normally used in tandem with other systems for residual clean-up. Extensive data on the solubiUty of acid gases in amine solutions are available (55,56). 

The addition of an alkanolamine, such as diethanolamine, to TYZOR TBT, as well as the use of a less moisture-sensitive alkanolamine titanate complex such as TYZOR TE, has been reported to prolong catalyst life and minimi2e ha2e formation in the polymer (475—476). Several excellent papers are available that discuss the kinetics and mechanism of titanate-cataly2ed esterification and polycondensation reactions (477—484). 

The formation of nitrosamines, e.g. n-nitrosodiedianolamine, which are possible human carcinogens, can occur in synthetic or semi-synthetic fluids which contain a nitrite salt and diethanolamine or triethanolamine. 

Amine salts of a-sulfonated fatty acids and esters are also used as antistatic agents. Mixtures of alkyl a-sulfo fatty acid ester diethanolamine salts and hexa-decyl stearate or butyl stearate are coated onto nylon yarn after fiber formation and before stretching [97]. Polypropylene can be made antistatic with an amine salt of a-sulfolauric acid [C10H21CH(SO3Na)COO +NH(CH2CH(OH) CH3)3] [98]. 

The effect of various types of inhibitors with respect to structure and solubility on the formation of N-Nitrosodiethanolamine was studied in a prototype oil in water anionic emulsion, Nitrosation resulted from the action of nitrite on diethanolamine at pH 5.2-5.A, Among the water soluble inhibitors incorporated into the aqueous phase, sodium bisulfite and ascorbic acid were effective. Potassium sorbate was much less so. The oil soluble inhibitors were incorporated into the oil phase of the emulsion. 

In order to ascertain that the NDELA formation does not occur as a result of trapping of the smoke or during the analysis, we added diethanolamine to tobacco prior to extraction with ethyl acetate in the presence of ascorbic acid. The control value for NDELA was 121 ppb and the experiment with 5.5 iqg diethanolamine addition yielded 113 ppb NDELA. For control of the smoke analysis we added 5.5 mg of DELA in the solvent trap and smoked cigarettes known to be free of DELA. Analysis of the trapped material showed no significant quantities of NDELA, so that artifactual formation of this nitrosamine during smoke collection and analysis can be ruled out. 

Fig. 8). Signals from molecules with ratios of anhydride (A)/diisopropanol-amine (D) of n n and n (n-b 1) were predominantly observed. Other signals, for example composed of n (n+2), n (n+3), etc., indicative of the reaction proceeding via pathway C in Fig. 6 (observed abundantly in resins made of diethanolamine) appeared only in minor amounts. The signals with n n ratios of an-hydride/diisopropanolamine, also present in minor amounts (usually between 5% and 20%) compared to the n (n-i-1), can be ascribed to cycle formation [14]. The relative abundance of these perspective peak series varied considerably with the monomer ratios, i. e., molecular weights and the type of cyclic anhy-... 

A 100-mL flask protected with a positive pressure of nitrogen is charged with 11 mmol of a 0.25 M pentane solution of iodo(diisopinocampheyl)borane [derived from ( +)-a-pinene]. The solution is cooled to — 100 C and treated dropwise with a solution of 980 mg (10 mmol) of 1,2-epoxycyclohexane in 2 mL of pentane. After stirring the solution for 0.5 h at —100 CC, the mixture is quenched by the addition of 1.8 mL (excess) of butanal. The mixture is allowed to warm gradually to r.t. and stirred for an additional 1 h. By that time "B NMR indicates clean formation of boronate [R OB(OEt)Ipc, d = 31], The mixture is diluted with 50 mL of pentane and treated with a 4 M THF solution of 12 mmol of 2.2 -diethanolamine. After the solution is stirred for 0.5 h, the precipitated boronate 2,2 -diethanolamine complex is filtered off and the filtrate is washed with water and brine and dried with anhyd Na2S04. The solution is concentrated under reduced pressure and the residue is purified by column chromatography followed by crystallization from pentane to provide the title compound in 89% yield mp 44 - 45°C [a] 3 —31.6 (c = 5, CHClj). 

Condensation of anthrandic acid (77-1) with an iminoether represents another method for preparing quinazolones. The reaction with the iminoether (77-2) from 2-cyano-5-nitrofuran and ethanohc acid can be visualized as proceeding through the formation of the amidine from addition-elimination of anthranilic acid cycliza-tion then affords the observed product (77-3). This is then converted to chloride (77-4) in the usual way. Displacement of the newly introduced chlorine with diethanolamine leads to the formation of nifurquinazol (77-5) [86], one of the antibacterial nitrofmans (see Chapter 8). 

Excretion of 7V-nitrosodiethanolamine in urine was evident in Sprague-Dawley rats receiving diethanolamine via the skin (100-400 mg/animal) and sodium nitrite in the drinking water (2000 ppm [mg/L]) for six days but not in the absence of sodium nitrite (Preussmann et al, 1981). 7V-Nitrosodiethanolamine was detected in a gastric rinse of rats treated with 100 pmol diethanolamine [59 mg/kg bw] and 400 pmol sodium nitrite [153 mg/kg bw] by gavage (Konishi et al, 1987). No evidence of formation of /V-nitrosodiethanolamine in vivo was found, however, in B6C3Fi mice treated with diethanolamine (160 mg/kg bw per day) and sodium nitrite (140 ppm in drinking-water 40 mg/kg bw) (Stott et al, 2000). 

Diethanolamine induced cell transformation in Syrian hamster embryo cells in vitro in two studies but not in another. It did not induce gene mutations, sister chromatid exchanges or chromosomal aberrations. Diethanolamine did not induce micronucleus formation in larval newt blood cells in either the absence or presence of sodium nitrite or nitrate. It was without effect on gene conversion in yeast and was not mutagenic in bacteria. 

Artom, C., Comatzer, W.E. Crowder, M. (1949) The aetion of an analogue of ethanolamine (diethanolamine) on the formation of liver phospholipides. J. biol. Chem., 180, 495-503 Artom, C., Lofland, H.B. Oates, J.A., Jr (1958) In vivo ineorporation of diethanolamine into liver lipides. J. biol. Chem., 233, 833-837... 

Preussmarm, R., Spiegelhalder, B., Eisenbrand, G, Wrirtele, G Hofmarm, I. (1981) Urinary excretion of V-nitrosodiethanolamine in rats following its epicutaneous and intratracheal administration and its formation in vivo following skin application of diethanolamine. Cancer Lett., 13, 227-231... 

Yordy, J.R. Alexander, M. (1981) Formation of N-nitrosodiethanolamine from diethanolamine in lake water and sewage. J. environ. Qual, 10, 266-270 Zeisel, S.H. (1996) Choline. A nutrient that is involved in the regulation of cell proliferation, cell death and cell transformation. In Hebver Kritchevsky, eds. Dietary Fats, Lipids, Hormones and Tumorigenesis, New York, Plennm Press, pp. 131-141... 

Triethanolamine is rapidly absorbed and excreted in rodent urine (about 60%) and faeces (about 20%), mainly in the unchanged form. Biodegradation of triethanolamine to monoethanolamine or diethanolamine or to any other putative metabolite has not been shown in rodents, nor has its incorporation into endogenous macromolecules. There is no evidence for formation of A-nitrosodiethanolamine from triethanolamine under physiological conditions. 

V-Nitrosodiethanolamine is formed by the action of nitrosating agents (nitrites 2-bromo-2-nitropropane-l,3-diol nitrogen oxides) on diethanolamine and triethanolamine (Schmeltz Wenger, 1979 Hofimann etal, 1982 Budavari, 1998). The rate of formation of A-nitrosodiethanolamine in aqueous solutions of ethanolamines is pH-, temperature- and time-dependent. The reaction was originally thought to occur only... 

Pour, P. Wallcave, L. (1981) The carcinogenicity of A -nitrosodiethanolamine, an environmental pollntant, in Syrian hamsters. Cancer Lett, 14, 23-27 Preussmann, R., Wiirtele, G, Eisenbrand, G Spiegelhalder, B. (1978) Urinary excretion of A -nitrosodiethanolamine administered orally to rats. Cancer Lett, 4, 207-209 Preussmann, R., Spiegelhalder, B., Eisenbrand, G, Wiirtele, G Hofmann, I. (1981) Urinary excretion of A -nitrosodiethanolamine in rats following its epicutaneous and intratracheal administration and its formation in vivo following skin application of diethanolamine. Cancer Lett, 13, 227-231... 

Irradiation in the presence of MDEA completely inhibits the formation of products. The amine quenches the fluorescence of Eosin with a rate constant of 8 x 108 M-1s-1 and quenches the Eosin triplet with a rate two orders of magnitude lower. A summary of rate constants for the decay of the triplet is presented in Table 8. In addition to the reactions shown in Scheme 3, with Am = (V-methyl diethanolamine, the rate constants for reaction of PDO with Eosin triplet and semioxidized Eosin radical in aqueous solution (Eqs. 19 and 20) are included in the table. 

Dicyanocobalamin 870 3,6-Dideoxyhexoses, formation of 747 Dielectric constant 47 Diesenhofer, Johan 84 Diethanolamine, pKa value of 99 Diethylmalonic acid, pKa value of 99 Diethylpyrocarbonate reaction with histidine 126... 

---