Tall oil fatty acid reactions

Diethylenetriamine, tall oil fatty acids reaction product... 

Tall oil fatty acids, reaction product with diethylene-triamine. Diethylenetriamine, tall oil fatty acids reaction product EINECS 263-160-2 Fatty acids, tail-oil, reaction products with diethylenetriamine Tall oil fatty acids, reaction product with diethylenetriamine. 

Oleic aminoethylimidazoline CAS 68526-44-3 EINECS/ELINCS 271-205-2 Synonyms Fatty acids, tall oil compds. with diethylene triamine tall oil fatty acid reaction prods. 

Fatty acids, soya, esters wtth propylene glycol. See Propylene glycol soyate Fa% acids, tall oil. See Tall oil acid Fa% acids, tall oil, ammonium saHs. See Ammonium tallate Fa% acids, tall oil, butyl esters, sulfated. See Sulfated butyl tallate Fa% acids, tall oil compds. wtth diethylene triamine tall oil fatty acid reaction prods.. See Oleic aminoethylimidazoline Fa% acids, tall oil, compds. wtth triethanolamine. See TEA-tallate Fa% acids, tail-oil, esters with ethoxylated sorbitol CAS 68953-01-5... 

C-21 dicarboxyhc acids are produced by Westvaco Corporation in Charleston, South Carolina in multimillion kg quantities. The process involves reaction of tall oil fatty acids (TOFA) (containing about 50% oleic acid and 50% hnoleic acid) with acryhc acid [79-10-7] and iodine at 220—250°C for about 2 hours (90). A yield of C-21 as high as 42% was reported. The function of the iodine is apparendy to conjugate the double bond in linoleic acid, after which the acryhc acid adds via a Diels-Alder type reaction to form the cycHc reaction product. Other catalysts have been described and include clay (91), palladium, and sulfur dioxide (92). After the reaction is complete, the unreacted oleic acid is removed by distillation, and the cmde C-21 diacid can be further purified by thin film distillation or molecular distillation. 

The dimer acids [61788-89-4] 9- and 10-carboxystearic acids, and C-21 dicarboxylic acids are products resulting from three different reactions of C-18 unsaturated fatty acids. These reactions are, respectively, self-condensation, reaction with carbon monoxide followed by oxidation of the resulting 9- or 10-formylstearic acid (or, alternatively, by hydrocarboxylation of the unsaturated fatty acid), and Diels-Alder reaction with acryUc acid. The starting materials for these reactions have been almost exclusively tall oil fatty acids or, to a lesser degree, oleic acid, although other unsaturated fatty acid feedstocks can be used (see Carboxylic acids. Fatty acids from tall oil Tall oil). 

Hydrogenation reactions were carried out in a stainless steel autoclave at 180°C, under 2-8 atm H2, in the presence of powdered supported Cu catalysts (10% wt) with a 3-15% copper loading. Si02, AI2O3 and Ti02 were used as the catalyst support and the catalysts prepared as already reported. These reactions were carried out on the esterified and distilled fraction of tall oil fatty acids. 

Fatty Acid. High-grade tall oil fatty acid is comprised essentially of oleic and linoleic acids in equal proportions. Typical carboxylic related reactions such as salt formation, esterification, amidization, reduction, sulfonation, sulfation, and ethylene oxide adduction are well-known. Since these reactions are common to all fatty acids, they will not be discussed further. However, there are a number of other more specific reactions applicable mainly to tall oil fatty acid that are significant industrially a brief review of these is in order. 

Tall oil fatty acid readily undergoes isomerization and reduction to essentially all monoenoic acid in the presence of a catalyst and a hydrogen donor. The reaction is very similar to the rosin disproportionation discussed earlier. Since tall oil rosin and fatty acid are produced simultaneously, it becomes obvious that... 

CAS 61790-12-3 EINECS/ELINCS 263-107-3 Synonyms Acids, tall oil Disproportionated tall oil fatty acid Fatty acids, tall oil Tall oil acids Tall oil fatty acid Tall oil fatty acids TOFA Definition Mixture of rosin acids and fatty acids recovered from the hydrolysis of tall oil Properties Liq. anionic Toxicoiogy Mildly irritating to skin repeated skin contact may result in allergic reactions such as rash or dermatitis inh. of mists can cause irritation TSCA listed Precaution Combustible Uses Emulsifier for metalworking fluids, polymerization, dyes, leather, coatings, petroleum industry mfg. of surfactants, soaps. 

Synonyms Fatty acids, tall oil, compds. with triethanolamine Fatty acids, tall oil, reaction prods, with triethanolamine Tall oil acids, triethanolamine condensate Tall oil fatty acids, triethanolamide Triethanolamine tallate Definition Triethanolamine salt of tall oil acid Uses Emulsifier, surfactant in cosmetics defoamer in mfg. of paper/paperboard Regulatory FDA 21CFR 176.210 Tea (Thea sinensis) extract CAS 84650-60-2... 

C2i-Diacid is prepared from tall oil fatty acids by reaction with iodine and acrylic (propenoic) acid at... 

The simplest reaction ofTOFA is the formation of soaps upon treatment with bases. Tall oil fatty acid soaps, such as ammonium tallate, potassium taUate, and sodium tallate are water soluble. The low proportion of saturated fatty acids allows them to be used in numerous cosmetic and personal care applications, functioning as an emulsifier or surfactant. The same applies for many industrial applications such as bitumen emulsions commonly used in roadway construction and maintenance. Asphalt emulsions are classified based on their ionic charge anionic, cationic, and nonionic. Anionic emulsions... 

The condensation reaction ofTOFA with a polyalkylene polyamine such as diethyl-enetriamine (DETA), triethylenetetramine (TETA), or tetraethylenepentamine (TEPA) in a molar ratio 1 1 yields amidoamines ofTOFA (also called tall oil fatty acid polyamides). Typically the amidation reaction is conducted at temperatures between 250 and 290 and usually a mixture of tall oil fatty acid polyamide and the corresponding tall oil fatty acid imidazoline is obtained (Figure 3B.12). 

The amidoamines possess reactive amine sites that allow for the cross-finking of epoxy resins in coatings, adhesives, and other applications. They are also used in asphalt to improve performance in road surfacing. Amidoamines and substituted imidazolines, prepared by the reaction of DETA or TETA with TOFA or crude tall oil, find use as corrosion inhibitors in petroleum production operations. Amidoamines have also been used in the processing of minerals. In the mining industry, the reaction product of tall oil fatty acids and DETA can be used to separate silica firom phosphate ore by flotation... 

Figure 3B.16 Diels-Alder and ene reactions with tall oil fatty acid.

Fig. 8 Reaction time by acid number. (1) Heated to 380°F in ly hr held at 380°F for 2 hr, lowered to 360 F, and held for properties. (2) Heated to 360 F in 1 hr and held for properties. Resin 3823 NT is similar to 3712 NT but contains TMA (244 gm), neopentyl glycol (352 gm), adipic acid (123 gm), tall oil fatty acids (362 gm). It is processed in a manner similar to resin 3712 NT. [Reprinted from Amoco TMA in Primers for Alkyd-Melamine Enamels and Acrylic Lacquers, Tech. Bull. TMA 25a. Copyright by the Amoco Chemical Corporation, Chicago, Illinois, 1974. Reprinted by permission of the copyright owner.]...

Branched fatty acids show a low pour point, low viscosity, high chemical stabihty, and high flash point compared to linear fatty acids. Saturated, branched fatty acids are therefore used as plasticizer, base fluids for lubricants, and for personal care formulations. One possibihty of manufacturing such alkyl-branched fatty acid derivatives is the cool o-merization ofethene or propene with tall oil fatty acid methyl ester (Figure 3B.14).This reaction is homogeneously catalyzed, for example, over RhCl3 3Fl20. 

The synthesis of higher Cl8 fatty acids (oleic, stearic) using a renewable, inedible feedstock, i.e. tall oil fatty acids (a by-product of wood processing of paper and pulp plants), is described. The effect on this process of amount of catalyst, hydrogen pressure, temp, and time of reaction is considered. The fatty acids are of use as activators of rubber mix vulcanisation. 1 ref. (Full translation of Kauch.i Rezina, No.6, 1996, p.39)... 

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