GB471629A - Improvements in or relating to a process for the treatment of rosinyl compounds and products produced thereby - Google Patents

Abstract

The unsaturation of rosinyl compounds is reduced by contacting the rosinyl compound with a hydrogenation catalyst such as nickel, platinum, palladium, or copper chromite, in the absence of any added substance capable of reducing the unsaturation of the rosinyl compound by reaction therewith. Other substances that will react with a functional group of the rosinyl compound but which do not effect the unsaturation may be present. A suitable catalyst may be prepared by adsorbing on granular alumina a solution of palladium chloride in aqueous hydrochloric acid, treating the product with aqueous formaldehyde, then with aqueous caustic soda, washing with water, dilute acetic acid and then water and finally drying. Suitable rosinyl compounds include abietic acid, sapinic acid, d-pimaric acid; American wood rosin, American, French Portuguese or Spanish gum rosin, partially hydrogenated rosins; esters of rosins, rosin acids, partially hydrogenated rosins or rosin acids with alcohols such as methanol, ethanol, propanols, butanols, oleyl alcohol, lauryl alcohol, abietyl alcohol, hydroabietyl alcohol, furfuryl alcohol, tetrahydrofurfuryl alcohol, ethylene glycol, diethylene glycol, triethylene glycol, glycerol, erythritol, pentaerythritol, sorbitol, mannitol or phenol; alcohols derived from rosins, rosin acids, partially hydrogenated rosins or rosin acids by hydrogenation of the carboxyl groups, such as abietyl alcohol, dihydroabietyl alcohol, sapinyl alcohol, dihydrosapinyl alcohol, pimaryl alcohol, dihydropimaryl alcohol; ethers of such rosin alcohols, such as abietyl, pimaryl or sapinyl methyl, ethyl, butyl, phenyl, bornyl or terpinyl ethers; hydrocarbons produced by decarboxylation of the rosins, rosin acids, partially hydrogenated rosins or rosin acids by means of a catalyst such as p-toluene sulphonic acid or fuller's earth; or metallic salts of the acids. The reaction is preferably carried in liquid phase in solution in an inert solvent such as aromatic or hydro - aromatic aliphatic hydrocarbons or petroleum fractions, and in the presence of an inert atmosphere such as carbon dioxide or nitrogen. The treated rosinyl compounds may be further treated by such processes as esterification, decarboxylation, reduction to an alcohol and etherified, or converted into metal salts with oxides or hydroxide such as those of sodium, potassium, lead, cobalt, or manganese. In examples: (1) French gum rosin, dihydroabietic acid, wood rosin, American gum rosin or methyl abietate are contacted with a palladium catalyst; (2) wood rosin is contacted with a palladium catalyst in the presence of decane; (4) wood rosin is contacted with a palladium catalyst in the presence of methyl alcohol (to yield a treated methyl abietate); (5) a treated American gum rosin is esterified with stearyl alcohol or glycerol; (7) a treated French gum rosin is esterified with glycerol; (8) a treated wood rosin or American gum rosin is decarboxylated by treatment with p-toluene sulphonic acid, and purified as desired by treatment with alkali; (10) a treated wood rosin is converted into its sodium, zinc, lead, or calcium salt; (14) a treated American gum rosin is converted into its calcium, lead or manganese salt; (17) treated American gum rosin, French gum rosin, or wood rosin or their esters are converted into alcohols by hydrogenation of an ethereal solution in the presence of a catalyst such as copper chromite, zinc chromite or nickel chromite. A treated abietic acid that has been esterified with methyl alcohol and then nitrated has a similar melting point to a nitrated treated methyl abietate.ALSO:A palladium hydrogenation catalyst is prepared by adsorbing an aqueous hydrochloric acid solution of palladium chloride on granular alumina, treating with aqueous formaldehyde, then with aqueous caustic soda, washing with water, dilute acetic acid, and water, and then drying.