Processes For Forming Alkylated Aryl Phosphite Compositions From Complex Hydrocarbon Streams

Abstract

Processes for alkylating hydroxyaryl compounds by reacting a hydroxyaryl with at least one olefin of a complex hydrocarbon stream. The complex hydrocarbon stream preferably comprises a fraction of a cracked hydrocarbon feed stream or the reaction products of a dehydrogenation of a paraffinic feedstock. The olefin of the complex hydrocarbon stream is preferably a branched olefin, e.g., isobutylene or isoamylene. The alkylated compositions are suitable for forming liquid phosphite compositions.

What is claimed is: 
     
         1 . A process for forming a phosphite composition, comprising
 reacting a hydroxyaryl compound with an olefin in a complex hydrocarbon stream to form an alkylate composition comprising two or more alkylated hydroxyaryl compounds; and   reacting the two or more alkylated hydroxyaryl compounds with a phosphorous trihalide to form the phosphite composition, wherein the phosphite composition comprises a least two different phosphites and is a liquid at ambient conditions.   
     
     
         2 . The process of  claim 1 , wherein the olefin is a branched olefin. 
     
     
         3 . The process of  claim 2 , wherein there is from 45 to 95 wt. % of the branched olefin in the complex hydrocarbon stream. 
     
     
         4 . The process of  claim 1 , wherein the complex hydrocarbon stream further comprises saturates. 
     
     
         5 . The process of  claim 4 , wherein there is from 0.5 to 20 wt. % of the saturates in the complex hydrocarbon stream. 
     
     
         6 . The process of  claim 1 , wherein the complex hydrocarbon stream is derived from a fraction of a cracked hydrocarbon feed stream. 
     
     
         7 . The process of  claim 1 , wherein the complex hydrocarbon stream is derived from reaction products of a dehydrogenation of a paraffinic feedstock. 
     
     
         8 . The process of  claim 1 , wherein the complex hydrocarbon stream contains at least 80 wt. % of hydrocarbons having a same number of carbon atoms. 
     
     
         9 . The process of  claim 8 , wherein the number of carbon atoms is from 2 to 18 carbons. 
     
     
         10 . The process of  claim 1 , wherein the hydroxyaryl compound is selected from the group consisting of phenol, 1-naphthol 2-naphthol, 9-phenanthrol, indanol, catechol, resorcinol, anthracen-2-ol, 4-biphenol, 4,4′-biphenol, xylenol, cresol, and derivatives thereof. 
     
     
         11 . The process of  claim 1 , further separating unreacted components of the complex hydrocarbon stream from the reaction mixture. 
     
     
         12 . The process of  claim 1 , wherein the at least two different phosphites comprise the following:
 tris(dialkylaryl)phosphite,   tris(monoalkylaryl)phosphite,   bis(dialkylaryl)monoalkylaryl phosphite, and   bis(monoalkylaryl)dialkylaryl phosphite.   
     
     
         13 . The process of  claim 1 , wherein the at least two different phosphites comprise the following:
 tris(monoalkylaryl)phosphite in an amount from 20 to 70 wt. %;   bis(monoalkylaryl)dialkylaryl phosphite in an amount from 15 to 60 wt. %,   tris(dialkylaryl)phosphite in an amount of from 0.1 to 20 wt. %; or   bis(dialkylaryl)monoaryl phosphite in an amount of from 2 to 20 wt. %.   
     
     
         14 . A process for forming a phosphite composition comprising at least two phosphites, the process comprising the steps of:
 (a) providing a complex hydrocarbon stream comprising at least one olefin and at least one saturate compound;   (b) contacting a hydroxyaryl with the complex hydrocarbon stream under conditions effective to form two or more alkylated hydroxyaryls in a reaction mixture;   (c) separating the at least one saturate compound from the reaction mixture; and   (d) reacting the two or more alkylated hydroxyaryls with a phosphorous trihalide to form the phosphite composition, wherein the phosphite composition is liquid at ambient conditions.   
     
     
         15 . An integrated reaction system for forming a phosphite composition, comprising:
 (a) a petrochemical refining system for forming a complex hydrocarbon stream comprising at least one olefin;   (b) an alkylate synthesis reactor in fluid communication with the petrochemical refining system and in which the olefin from the complex hydrocarbon stream is reacted with to one or more hydroxyaryls under conditions effective to form an alkylate composition; and   (c) a phosphite synthesis reactor in fluid communication with the alkylate synthesis reactor and in which the alkylate composition is reacted with a phosphorus trihalide, with or without catalyst, under conditions effective to form the liquid phosphite composition.