Patent GB-749712-A (GB)
Title: Improvements in or relating to the production of esters of phosphorus oxy-acids and compositions containing such esters
IPC: C07F9/11
Filed: 1953-09-21
Abstract: A composition suitable for use in producing textile lubricants and containing an ester of a phosphorus oxy-acid is obtained by reacting an organic hydroxy compound with a solid ester-forming derivative of a phosphorus oxy-acid previously dispersed in a hydrocarbon lubricant liquid.  The process is particularly applicable to the production of alkyl esters from aliphatic alcohols, e.g. n-propanol, n-butanol, n-hexanol, n-decanol, mixed decanols, 3.5.5-trimethyl hexanol, 2-butyl octanol, trimethyl nonanol, and di-isobutyl carbinol.  It may also be employed for the production of esters of other organic hydroxy compounds, including aromatic compounds, e.g. phenol, and the cresols and xylenols.  Specified ester-forming derivatives are phosphorus pentoxide, phosphorus tetroxide and phosphorus pentachloride.  The hydrocarbon lubricant liquid is preferably an oil having a viscosity of at least 40 seconds at 100 DEG  F. on the Saybolt Universal Viscosity Scale.  A hydrocarbon lubricant wax which can be melted at a temperature suitable for use in carrying out the reaction may also be used.  The reaction temperature is preferably between 50 DEG  C. and 100 DEG  C. with a reaction time of between 10 and 60 minutes.  The ratio of organic hydroxy compound to the phosphorus compound may be such as to provide 3 to 4 free hydroxyl groups per mol. of phosphorus compound when it is desired to produce a tri-ester, e.g. a trialkyl phosphate, but for producing mono and di-esters the quantity of hydroxy compound may be such as to provide only 1.5 to 2.0 hydroxy groups per mol. of phosphorus compound, e.g. phosphorus pentoxide.  If desired the ester may be separated from the composition formed by conventional methods such as extraction with water or other suitable-solvent.  The dispersion of the ester-forming phosphorus compound in hydrocarbon lubricant preferably contains between 15 and 25 parts by weight of the phosphorus compound for each 100 parts by weight of the hydrocarbon lubricant.  In examples (1) n-decanol is added to a dispersion of phosphorus pentoxide in a mineral oil having a Saybolt Universal Viscosity of 50 seconds at 100 DEG  F. and the mixture heated to 80 DEG  C. for 20 minutes, cooled, and filtered to yield a clear liquid containing n-decanol esters of phosphoric acid; (2) as in (1) except that 3,5,5-trimethyl hexanol is used instead of n-decanol to yield a clear liquid containing 3,5,5-trimethyl hexanol esters of phosphoric acid. Specifications 725,799, 732,933 and 747,499, [all in Group III], are referred to.ALSO:A composition suitable for use in producing textile lubricants and containing an ester of a phosphorus oxy-acid is obtained by reacting an organic hydroxy compound with a solid ester-forming derivative of a phosphorus oxy-acid previously dispersed in a hydrocarbon lubricant liquid (see Group IV(b)). Specified hydroxy compounds are aliphatic alcohols, e.g. n-propanol, n-butanol, n-hexanol, n-decanol, mixed decanols, 3, 5, 5-trimethyl hexanol, 2-butyl octanol, trimethyl nonanol, and diisobutyl carbinol, and aromatic compounds, e.g. phenol, and the cresols and xylenols. Specified ester-forming derivatives are phosphorus pentoxide, phosphorus tetroxide, and phosphorus pentachloride.  The hydrocarbon lubricant liquid is preferably an oil having a viscosity of at least 40 seconds at 100 DEG F. on the Saybolt Universal Viscosity Scale.  A hydrocarbon lubricant wax which can be melted at a temperature suitable for use in carrying out the reaction may also be used.  The reaction temperature is preferably between 50 DEG C. and 100 DEG C. with a reaction time of between 10 and 60 minutes.  The ratio of organic hydroxy compound to the phosphorus compound may be such as to provide 3 to 4 free hydroxyl groups per mole of phosphorus compound when it is desired to produce a tri-ester, e.g. a trialkyl phosphate, but for producing mono and di-esters the quantity of hydroxy compound may be such as to provide only 1.5 to 2.0 hydroxy groups per mole of phosphorus compound, e.g. phosphorus pentoxide.  The dispersion of the ester-forming phosphorus compound in hydrocarbon lubricant preferably contains between 15 and 25 parts by weight of the phosphorus compound for each 100 parts by weight of the hydrocarbon lubricant.  In examples: (1) n-decanol is added to a dispersion of phosphorus pentoxide in a mineral oil having a Saybolt Universal Viscosity of 50 seconds at 100 DEG F. and the mixture heated at 80 DEG C. for 20 minutes, cooled, and filtered to yield a clear liquid containing n-decanol esters of phosphoric acid; (2) as in (1) except that 3, 5, 5-trimethyl hexanol is used instead of n-decanol to yield a clear liquid containing 3, 5, 5-trimethyl hexanol esters of phosphoric acid.  Specifications 725,799, 732,933 and 747,499 are also referred to.