Sebacic acid, esterification

More recent developments in this country have included synthesis of relatively stable oils of low volatility, low pour point, and high viscosity index by esterification of octyl alcohols, such as 2-ethylhexanol, with dibasic acids such as adipic acid and sebacic acid (3). Octyl alcohols may be synthesized from petroleum hydrocarbons via the oxo process. Although of relatively high cost, these synthetic oils find general application in making greases for lubrication of antifriction bearings and instruments in aircraft. 

Polyesters from propylene glycol and dicarboxylic acids, especially adipic and sebacic acid, are commercial products suggested for PVC as well as for cellulose esters. The well known Paraplex resins of Rohm Haas, which are compatible with nitrile and GRS rubber, belong to this group. Other products are the Ultramolls of Farbenfabriken Bayer. Some polyesters of this type have a tendency to exude on storage, especially if esterification is not complete. 

Dibutyl sebacate is manufactured by the esterification of n-butanol and sebacic acid in the presence of a suitable catalyst, and by the distillation of sebacic acid with -butanol in the presence of concentrated acid. 

Ethyl hydrogen sebacate has been prepared by the direct esterification of sebacic acid with ethyl alcohol, by the halfsaponification of diethyl sebacate, and by heating equimolecular quantities of sebacic acid and diethyl sebacate for several hours. ... 

Castor oil and vernoia oil are also based on tryglycerides, but they bear different functional groups. The first contains hydroxyl and vernoia oil epoxy groups. When one of these two oils reacts with difunctional sebacic acid, a three-dimensional esterification reaction occurs, forming a network [64, 65]. 

Titanium alkoxides feature as catalysts in the esterification of succinic, adipic, azelaic, and sebacic acids with 2-ethyl hexanol and in the production of acetate... 

Stearic Acid 0.2-20 150-300 65-148 - E - - in esterification kettle with sebacic acid, adipic acid, phthalic anhydride, and toluene sulfonic acid. Alloy C - 2 mpy In liquid. 1.2 mpy m vapors. 

In all these oils, because the average functionality is greater than two, a crosslinked product can be made using difunctional reactants. When castor (or lesquerella) oil reacts with difunctional sebacic acid, a three dimensional esterification reaction occurs between the hydroxyl and acid functionalities, forming a network polymer. Oxirane (epoxy) groups can also react to form crosslinked polyesters with dibasic acids, albeit... 

In plasticizer manufacture, eg, of phthalates or sebacates, uskig sulfuric or/ -toluenesulfonic acid catalysts, the temperature (140—150°C) requked for rapid reaction and high conversion may dehydrate or oxidize the alcohol and may yield a dark or foul-smelling product. Neutral titanates do not cause such side reactions. Although a temperature of 200°C is requked, esterifications can easily be forced to over 99% conversion without the formation of odors or... 

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