Patent GB-475572-A (GB)
Title: Esters of the thio-acids of phosphorus and their manufacture
IPC: C07F9/17
Filed: 1936-02-19
Abstract: Esters of thioacids of phosphorus are prepared by reacting an esterifying derivative of a thioacid of phosphorus with at least one molecular proportion of an alcohol containing at least ten carbon atoms or by reacting an esterifying derivative of an oxygen acid of phosphorus with at least one molecular proportion of an aliphatic mercaptan containing at least ten carbon atoms.  When acid esters are produced they may be further reacted with a different alcohol or mercaptan or with a phenol.  The esters may be converted into salts with alkalies, alkaline earths, zinc, lead, ammonia, laurylamine, diethylamine, cyclohexylamine, triethanolamine, naphthylamine, o-toluidine or diphenylguanidine. The esters or their salts may be used as foaming or flotation agents, as acid inhibitors in pickling baths, as corrosion inhibitors to retard the oxidation of metals in aqueous baths, as high pressure lubricant assistants and as vulcanization accelerators.  In examples: (1) dilauryldithiophosphate is prepared by reacting phosphorus pentasulphide in toluene with lauryl alcohol; its sodium, aniline, pyridine and p-nitroaniline salts are mentioned; (2) phosphoruspentasulphide is also reacted with oleyl and stearyl alcohols and the alcohols derived from coconut oil; (3) myristyl and cetyl alcohols are esterified by means of phosphorusthiochloride; (4) lauryl mercaptan is reacted with phosphorus oxychloride, phosphorus trichloride and also with phosphorus pentasulphide; (4) lauryl alcohol is esterified with phosphorus trisulphide; (5) phosphorus trisulphotetrabromide is reacted with myristyl and eicosyl alcohols.  Decyl, undecyl, ceryl, eleostearyl, linoleyl, ricinoleyl and abietyl alcohols and mercaptans may also be employed as well as alcohols obtained by reduction of sperm oil or from olefines obtained by cracking paraffin wax.  Chlor benzene, carbontetrachloride and benzene may be used as solvents.ALSO:Esters of thio-acids of phosphorus or salts thereof which are prepared (a) by reacting an esterifying derivative of a thio-acid of phosphorus with at least one molecular proportion of an alcohol containing at least ten carbon atoms, or (b) by reacting an esterifying derivative of an oxygen acid of phosphorus with at least one molecular proportion of an aliphatic mercaptan containing at least ten carbon atoms, may be used as high-pressure lubricant assistants.  When acid esters are produced they may be further reacted with a different alcohol or mercaptan or with a phenol.  The esters may be converted into salts with alkalies, alkaline earths, zinc, lead, ammonia, laurylamine, diethylamine, cyclohexylamine, triethanolamine, naphthylamine, o-toluidine or diphenylguanidine.  In examples: (1) dilauryldithiophosphate is prepared by reacting phosphorus pentasulphide in toluene with laurylalcohol; its sodium, aniline, pyridine and p-nitroaniline salts are mentioned: (2) phosphorus-pentasulphide is also reacted with oleyl and stearyl alcohols and the alcohols derived from coconut oil: (3) myristyl and cetyl alcohols are esterified by means of phosphorus thiochloride: (4) lauryl mercaptan is reacted with phosphorus oxychloride, phosphorus trichloride and also with phosphorus pentasulphide: (5) lauryl alcohol is esterified with phosphorus trisulphide: (6) phosphorus trisulphotetrabromide is reacted with myristyl and eicosyl alcohols.  Decyl, undecyl, ceryl, eleostearyl, linoleyl, ricinoleyl and abietyl alcohols and mercaptans may also be employed, as well as alcohols obtained by reduction of sperm oil or derived from olefines obtained by cracking paraffin wax.ALSO:Esters of thio-acids of phosphorus or salts thereof which are prepared (a) by reacting an esterifying derivative of a thio-acid of phosphorus with at least one molecular proportion of an alcohol containing at least ten carbon atoms or (b) by reacting an esterifying derivative of an oxygen acid of phosphorus with at least one molecular proportion of an aliphatic mercaptan containing at least ten carbon atoms may be used as vulcanization-accelerators.  When acid esters are produced they may be further reacted with a different alcohol or mercaptan or with a phenol.  The esters may be converted into salts with alkalies, alkaline earths, zinc, lead, ammonia, laurylamine, diethylamine, cyclohexylamine, triethanolamine, naphthylamine, o-toluidine or diphenylguanidine.  In examples: (1) dilauryldithiophosphate is prepared by reacting phosphorus pentasulphide in toluene with laurylalcohol, its sodium, aniline, pyridine and p-nitroaniline salts are mentioned; (2) phosphorus-pentasulphide is also reacted with oleyl and stearyl alcohols and the alcohols derived from coconut oil; (3) myristyl and cetyl alcohols are esterified by means of phosphorusthiochloride; (4) lauryl mercaptan is reacted with phosphorus oxychloride, phosphorus trichloride and also with phosphorus pentasulphide; (5) lauryl alcohol is esterified with phosphorus trisulphide; (6) phosphorus trisulphotetrabromide is reacted with myristyl and eicosyl alcohols.  Decyl, undecyl, ceryl, eleostearyl, linoleyl, ricinoleyl and abietyl alcohols and mercaptans may also be employed as well as alcohols obtained by reduction of sperm oil or derived from olefines obtained by cracking paraffin wax.