Method of Making a Phosphite Ester
The present disclosure is directed to a method of making a phosphite ester. The method comprises reacting a hydroxyl-substituted compound comprising a hydroxyl-substituted alkyl compound, a hydroxyl-substituted aryl compound, or a mixture thereof with a phosphorus halide to make a product mixture comprising a hydrogen halide and a reaction product comprising the phosphite ester and a phosphohalodite and removing the hydrogen halide from the product mixture.
1 - 66 . (canceled)
67 . A method of making a phosphite ester, the method comprising:
reacting a hydroxyl-substituted compound comprising a hydroxyl-substituted alkyl compound, a hydroxyl-substituted aryl compound, or a mixture thereof with a phosphorus halide, wherein the hydroxyl-substituted compound and the phosphorus halide are reacted in a molar ratio of from about 2.3 to about 5, at a temperature of about 200° C. or less to make a product mixture comprising a hydrogen halide and a reaction product comprising the phosphite ester and one or more compounds having the following structure (I) and being present in an amount of about 0.3 wt. % or more to about 15 wt. % or less based on the weight of the reaction product:
wherein
R 1 is an alkyl or an aryl;
R 2 is an alkyl or an aryl;
Y is Z or —O—H; and
Z is a halide; and
removing the hydrogen halide from the product mixture.
68 . The method of claim 67 , wherein the phosphorus halide comprises a phosphorus trichloride.
69 . The method of claim 67 , wherein the hydroxyl-substituted compound comprises a hydroxyl-substituted aryl compound.
70 . The method of claim 69 , wherein the hydroxyl-substituted alkaryl compound comprises a C 1 -C 4 alkyl group substitution.
71 . The method of claim 67 , wherein the removing step includes a vacuum, a nitrogen sweep, a nitrogen sparge, or a combination thereof.
72 . The method of claim 67 , wherein the phosphite ester has the following structure:
wherein
R 21 , R 22 , and R 23 are each independently an alkyl or an aryl.
73 . The method of claim 72 , wherein R 21 , R 22 , and R 23 are each aryl.
74 . The method of claim 73 , wherein the aryl comprises a C 1 -C 4 alkyl group substitution.
75 . The method of claim 67 , wherein the phosphite ester has the following structure:
76 . The method of claim 67 , wherein the phosphite ester has the following structure:
77 . The method of claim 67 , wherein the one or more compounds of structure (I) has the following structure:
wherein
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are independently hydrogen or an alkyl.
78 . The method of claim 67 , wherein the one or more compounds of structure (I) has the following structure:
wherein
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are independently hydrogen or an alkyl; and
Z is as defined above.
79 . The method of claim 67 , wherein the one or more compounds of structure (I) has the following structure:
wherein
Z is as defined above.
80 . The method of claim 67 , wherein the reaction product comprises a first compound having the following structure based on structure (I):
wherein
R 1 and R 2 are as defined above;
Y is Z; and
Z is as defined above; and
a second compound having the following structure based on structure (I):
wherein
R 1 and R 2 are as defined above.
81 . The method of claim 67 , wherein the hydrogen halide comprises hydrogen chloride.
82 . The method of claim 67 , wherein the phosphite ester is present in the reaction product in an amount of about 80 wt. % or more.
83 . The method of claim 67 , wherein the compound of structure (I) is present in the reaction product in an amount of about 1 wt. % or more to about 12 wt. % or less.
84 . The method of claim 67 , wherein the compound of structure (I) is present in the reaction product in an amount of about 2 wt. % or more to about 4 wt. % or less.
85 . The method of claim 67 , wherein the compound of structure (I) is present in the reaction product in an amount of about 7 wt. % or more to about 12 wt. % or less.
86 . The method of claim 67 , wherein the reaction product has a chloride content of from about 3,000 ppm to about 15,000 ppm.
87 . The method of claim 67 , wherein the reaction product has a chloride content of from about 10,000 ppm to about 15,000 ppm.
88 . The method of claim 67 , wherein the reaction product comprises 1.5 wt. % or less of phenol.
89 . The method of claim 67 , wherein the hydroxyl-substituted compound and the phosphorus halide are reacted in a molar ratio of from about 2.3 to less than about 3.
90 . The method of claim 67 , wherein the reacting step is conducted without the presence of a solvent and/or the presence of a catalyst.