Patent GB-788200-A (GB)
Title: Improvements in or relating to condensation products from aromatic hydrocarbon derivatives and carbohydrate-like materials
Inventor: LINN CARL BARNES
IPC: C08B15/00
Filed: 1955-10-28
Abstract: A compound having a hydroxy group attached directly to an aromatic nucleus is reacted with a simple sugar, a desoxy or omegacarboxy derivative thereof, a compound sugar or a polysaccharide, in the presence of hydrogen fluoride as catalyst, and the resultant condensation products recovered.  Reaction conditions and the carbohydrate-like reactants are as described in Specification 787,531.  Aromatic hydroxy compounds specified include mono-, di- and tri-hydric phenols, hydroxy-diphenyls, chlor-, brom- and amino-phenols, and such derivatives as saligenin and hydroxyacetophenones.  Sulphonation, sulphation, nitration and resinformation may be effected as in Specification 787,531.  Some products such as the reaction products of glucose with 2 mols. of 2,4-dimethylphenol are of use as antioxidants, e.g. for hydrocarbons, foods and alcoholic beverages.  In examples: (1) phenol and cellulose are reacted in n-pentane as diluent, the water-insoluble product yielding 1,1-di-p-hydroxyphenol-1-desoxy-D-glucitol; (2) a similar reaction yields also what is believed to be a monophenolated glucose; (3) 2,4-dimethylphenol and cellulose yield 1,1 - di - (2 - hydroxy - 3,5 - dimethylphenol) - 1 - desoxy - D - glucitol used as an antioxidant, a stabilizer for alcoholic beverages and for raising the induction period of cracked gasoline; (4) the product of (1) is condensed with formaldehyde using either basic or acidic catalysts to give resins; (5) a resin is produced with the use of heat and pressure but without formaldehyde; (6) nitric acid yields nitrates; (7) the nitrate yields a resin with formaldehyde and ammonia; (8) an acetate ester of the product of (1) is nitrated; (9) phenol and alginic acid are reacted at 0 DEG  C.; (10) fractions of the product of (9) are condensed with formaldehyde using various catalysts to give resins.ALSO:A compound having a hydroxy group attached directly to an aromatic nucleus is reacted with a simple sugar, a desoxy or omegacarboxy derivative thereof, a compound sugar or a polysaccharide, in the presence of hydrogen fluoride as catalyst, and the resultant condensation products are recoevered.  They are used as detergent aids.  Reaction conditions and the carbohydrate-like reactants are as described in Specification 787,531.  Aromatic hydroxy compounds specified include mono-, di- and tri-hydric phenols, hydroxy-diphenyls, chlor-, brom- and amino-phenols, and such derivatives as saligenin and hydroxyacetophenones.  Sulphonation and sulphation may be effected as in Specification 787,531 yielding detergent products. Some products, such as the reaction products of glucose with 2 mols. of 2,4-dimethylpheol, are of use as antioxidants, e.g. for hydrocarbons, foods, e.g. lard, and alcoholic beverages.  In an example, (3) 2,4-dimethylphenol and cellulose yield 1,1 - di - (2 - hydroxy - 3,5 - dimethylphenol) - 1 - desoxy - D - glucitol used as an antioxidant for lard, a stabilizer for alcoholic beverages, and for raising the induction period of cracked gasoline.ALSO:A compound having a hydroxy group attached directly to an aromatic nucleus is reacted with a simple sugar, a desoxy or omega-carboxy derivative thereof, a compound sugar or a polysaccharide, e.g. cellulose, in the presence of hydrogen fluoride as catalyst, and the resultant condensation products are recovered. Reaction conditions and the carbohydrate-like reactants are as described in Specification 787,531.  Aromatic hydroxy compounds specified include mono-, di- and tri-hydric phenols, hydroxy-diphenyls, chlor-, brom- and aminophenols, and such derivatives as saligenin and hydroxyacetophenones. Sulphonation, sulphation, nitration and resin-formation may be effected as in Specification 787,531.  In examples: (1) phenol and cellulose are reacted in n-pentane as diluent, the water-insoluble product yielding 1,1-di-p-hydroxyphenol-1-desoxy-D-glucitol; (2) a similar reaction yields also what is believed to be a monophenolated glucose; (3) 2,4-dimethylphenol and cellulose yield 1,1 - di - (2 - hydroxy - 3,5 - dimethyl - phenol) - 1 - desoxy - D - glucitol; (4) the product of (1) is condensed with formaldehyde, using either basic or acidic catalysts, to give resins; (5) a resin is produced with the use of heat and pressure, but without formaldehyde; (6) nitric acid yields nitrates; (7) the nitrate yields a resin with formaldehyde and ammonia; (8) an acetate ester of the product of (1) is nitrated; (9) phenol and alginic acid are reacted at 0 DEG  C.; (10) fractions of the product of (9) are condensed with formaldehyde, using various catalysts, to give resins.ALSO:As a preventative of oxidation in food products, e.g. lard, and of haze formation in fermented alcoholic beverages there is employed a product formed by reaction, in the presence of hydrogen fluoride, of a compound having a hydroxy group attached directly to an aromatic nucleus and a simple sugar, a desoxy or omega-carboxy derivative thereof, a compound sugar or a polysaccharide.  Examples of the reaction include formation of (i) 1,1-di-p-hydroxyphenol-1-desoxy-D-glucitol and of a monophenolated glucose from phenol and cellulose in n-pentane; (ii) 1,1,-di-(2-hydroxy-3,5-di-methylphenol) - 1 - desoxy - D - glucitol from 2,4-dimethylphenol and cellulose; (iii) a water-soluble antioxidant from 2,4-dimethylphenol and glucose.