Method for making organodiphosphites from phosphorochloridites characterized by measuring side-product levels to determine further additions

A method for producing a diphosphite ligand structure (DLS) having the following structure,

• comprising:
• contacting a phosphorochloridite having the following structure,
• with a bisaryl compound having the following structure,
• and a tertiary organic amine to provide a final reaction mixture comprising the diphosphite;
• wherein the contacting comprises
• providing a pre-determined limit for the mole percent of phosphorus present as T-phite ligand structure (TLS), having the chemical structure shown below, in the final reaction mixture
• providing a pre-determined limit for the mole percent of phosphorus present as C-phite ligand structure (CLS), having the chemical structure shown below, in the final reaction mixture
• providing a pre-determined limit for the mole percent of phosphorus present as a ligand hydrolysis product (LHP) in the final reaction mixture, comprising a product derived by a process comprising
• hydrolysis of the DLS or of the phosphorochloridite;
• hydrolysis of a product derived from the DLS or from the phosphorochloridite;
• or
• reaction of the hydrolysis product of the DLS or of the phosphorochloridite, or reaction of the hydrolysis product of a product derived from the DLS or from the phosphorochloridite;
• providing a pre-determined goal for a conversion of phosphorochloridite in the first reaction mixture;
• adding the bisaryl compound to the phosphorochloridite in a first serial addition to provide a first reaction mixture, wherein the amount of bisaryl compound added is sufficient to cause the percent conversion of the phosphorochloridite in the first reaction mixture to be equal to or greater than the pre-determined goal for a conversion of the phosphorochloridite in the first reaction mixture;
• determining the mole percent of phosphorus present in the first reaction mixture as TLS;
• determining the mole percent of phosphorus present in the first reaction mixture as CLS;
• determining the mole percent of phosphorus present in the first reaction mixture as LHP;
• determining the percent conversion of the phosphorochloridite in the first reaction mixture;
• wherein if in the first reaction mixture both the mole percents of phosphorus present as the CLS and the TLS are equal to or greater than the respective pre-determined limits for the mole percents of phosphorus present as the CLS or the TLS in the final reaction mixture, then the second serial addition comprises water;
• wherein if in the first reaction mixture the mole percent of phosphorus present as the CLS is equal to or above the pre-determined limit for the mole percent of phosphorus present as the CLS in the final reaction mixture, and in the first reaction mixture the mole percent of phosphorus present as the TLS is not equal to or above the pre-determined limit for the mole percent of phosphorus present as the TLS in the final reaction mixture, and in the first reaction mixture the mole percent of phosphorus present as LHP is equal or to greater than the pre-determined limit for the mole percent of phosphorus present as LHP in the final reaction mixture, then the second serial addition comprises the alcohol having the chemical structure R1—OH or R2—OH;
• wherein if in the first reaction mixture neither the mole percent of phosphorus present as the CLS nor the TLS is equal to or above the respective pre-determined limits for the mole percents of phosphorus present as the CLS or the TLS in the final reaction mixture, and the conversion of phosphorochloridite in the first reaction product is less than the pre-determined goal for the conversion of phosphorochloridite in the second reaction mixture, then second serial addition comprises the bisaryl compound, wherein the quantity of the bisaryl compound to add in the second serial addition is determined using a comparison of the percent conversion of the phosphorochloridite in the first reaction mixture to the pre-determined goal for the conversion of phosphorochloridite in the second reaction mixture to determine the amount of the bisaryl compound to add in the second serial addition, comprising:
• using at least one selectivity ratio of the phosphorochloridite to the phosphorus-containing ligand and CLS at a given conversion range in combination with the determined mole percents of TLS and CLS in the first reaction mixture to forecast a maximum percent conversion of phosphorochloridite such that at the forecasted percent conversion in the second reaction mixture the percent of phosphorus present as CLS in the second reaction mixture is less than the pre-determined limit for the percent of phosphorus present as CLS in the final reaction mixture;
• and
• setting a pre-determined goal for the conversion of phosphorochloridite in the second reaction mixture to the forecasted maximum percent conversion of the phosphorochloridite;
• adding the second serial addition to the first reaction mixture, comprising one or more compounds selected from the group consisting of the bisaryl compound, water, and the alcohol having the chemical structure R1—OH or R2—OH, to provide the second reaction mixture, wherein if bisaryl compound is added in the second serial addition then the amount of the bisaryl compound in the second serial addition is sufficient to cause the percent conversion of the phosphorochloridite in the second reaction mixture to be about equal to the pre-determined goal for the conversion of the phosphorochloridite in the second reaction mixture;
• and
• either
• performing third addition steps comprising
• optionally determining a mole percent of phosphorus present in the second reaction mixture as at least one side-product;
• optionally using a comparison of the mole percent of phosphorus present in the second reaction mixture as the at least one side-product to a pre-determined limit for the mole percent of phosphorus present as the at least one side-product in the final reaction mixture, to determine an amount of one or more compounds selected from the group consisting of water and the alcohol having the chemical structure R1—OH or R2—OH, to add in a third serial addition;
• and
• adding the third serial addition to the second reaction mixture to provide the final reaction mixture, wherein the quantities of the one or more compounds added in the third addition are such that the conversion of the phosphorochloridite in the final reaction mixture is about 100%;
• or
• the final reaction mixture is the second reaction mixture, wherein the quantities of the one or more compounds added in the second addition are such that conversion of the phosphorochloridite in the final reaction mixture is about 100%;
• wherein R1 and R2 are the same or different, substituted or unsubstituted, monovalent aryl groups;
• and each of R3, R4, R5, R6 is independently selected from the group consisting of hydrogen and C1-10 alkyl wherein alkyl refers to straight chain (C1-C10)alkyl groups, branched (C1-C20)alkyl groups or (C3-C20)cycloalkyl groups.