Multifunctional lubricating oil base stocks and processes for preparing same

Abstract

A composition that includes one or more compounds represented by the formula (R 1 ) a (X)(R 2 ) b wherein R 1 and R 2 are the same or different and are the residue of an alkyl group having from about 4 to about 40 carbon atoms, X is the residue of at least one polycyclic, heteroatom-containing, hydrocarbon compound, a is a value from 1 to about 8, and b is a value from 0 to about 8. The composition has a viscosity (Kv 100 ) from about 2 to about 300 at 100° C. as determined by ASTM D-445, and a viscosity index (VI) from about −100 to about 300 as determined by ASTM D-2270. The disclosure also relates to a process for producing the composition, a lubricating oil base stock and lubricating oil containing the composition, and a method for improving oxidative stability of a lubricating oil by using as the lubricating oil a formulated oil containing the composition.

What is claimed is: 
     
         1 . A composition comprising one or more compounds represented by the formula
   (R 1 ) a (X)(R 2 ) b      
       wherein R 1  and R 2  are the same or different and are the residue of an alkyl group having from 4 to 40 carbon atoms, X is the residue of at least one polycyclic, heteroatom-containing, hydrocarbon compound, a is a value from 1 to 8, and b is a value from 0 to 8; wherein said composition has a viscosity (Kv 100 ) from 2 to 300 at 100° C. as determined by ASTM D-445, and a viscosity index (VI) from −100 to 300 as determined by ASTM D-2270. 
     
     
         2 . The composition of  claim 1  wherein R 1  and R 2  are selected from the residue of a mPAO dimer (C 6 -C 40 ), trimer (C 6 -C 40 ), tetramer (C 6 -C 40 ), pentamer (C 6 -C 40 ), and hexamer (C 6 -C 40 ), or α-olefin (C 4 -C 40 ), X is selected from the residue of at least one of phenothiazine and phenyl phenothiazine, a is a value from 1 to 4, and b is a value of 0 or 1. 
     
     
         3 . The composition of  claim 1  wherein the polycyclic, heteroatom-containing, hydrocarbon compound comprises phenothiazine, a derivative of phenothiazine, 2-methylthiophenothiazine, 10-methylphenothiazine, monotetradecylphenothiazine, ditetradecylphenothiazine, monodecylphenothiazine, didecylphenothiazine, monononylphenothiazine, dinonylphenothiazine, monoctylphenothiazine, dioctylphenothiazine, monobutylphenothiazine, dibutylphenothiazine, monostyrylphenothiazine, distyrylphenothiazine, butyloctylphenothiazine, styryloctylphenothiazine, and mixtures thereof. 
     
     
         4 . The composition of  claim 1  which comprises one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds. 
     
     
         5 . The composition of  claim 3  which comprises an alkylated phenothiazine, an alkylated derivative of phenothiazine, or mixtures thereof. 
     
     
         6 . The composition of  claim 4  wherein the one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds comprise monoalkylated polycyclic, heteroatom-containing, hydrocarbon compounds and dialkylated polycyclic, heteroatom-containing, hydrocarbon compounds, wherein the ratio of monoalkylated polycyclic, heteroatom-containing, hydrocarbon compounds to dialkylated polycyclic, heteroatom-containing, hydrocarbon compounds is from 5:95 to 95:5. 
     
     
         7 . The composition of  claim 4  wherein the alkylated polycyclic, heteroatom-containing, hydrocarbon compounds have a quaternary carbon content from 50 percent to 100 percent, based on the total primary, secondary, tertiary and quaternary carbons in the alkylated polycyclic, heteroatom-containing, hydrocarbon compounds. 
     
     
         8 . The composition of  claim 1  which is selected from a polycyclic, heteroatom-containing, hydrocarbon compound-containing mPAO dimer, trimer, tetramer, pentamer, hexamer and higher oligomer. 
     
     
         9 . A composition comprising one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds, wherein said one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds are produced by a process comprising reacting a polyalphaolefin oligomer or α-olefin (C 4 -C 40 ) with at least one polycyclic, heteroatom-containing, hydrocarbon compound, in the presence of a catalyst, under reaction conditions sufficient to produce said one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds. 
     
     
         10 . The composition of  claim 9  wherein the one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds are represented by the formula
   (R 1 ) a (X)(R 2 ) b    
 
       wherein R 1  and R 2  are the same or different and are the residue of an alkyl group having from 4 to 40 carbon atoms, X is the residue of at least one polycyclic, heteroatom-containing, hydrocarbon compound, a is a value from 1 to 8, and b is a value from 0 to 8; wherein said composition has a viscosity (Kv 100 ) from 2 to 300 at 100° C. as determined by ASTM D-445, and a viscosity index (VI) from −100 to 300 as determined by ASTM D-2270. 
     
     
         11 . The composition of  claim 10  wherein R 1  and R 2  are selected from the residue of a mPAO dimer (C 6 -C 40 ), trimer (C 6 -C 40 ), tetramer (C 6 -C 40 ), pentamer (C 6 -C 40 ), and hexamer (C 6 -C 40 ), or α-olefin (C 4 -C 40 ), X is selected from the residue of at least one of phenothiazine and phenyl phenothiazine, a is a value from 1 to 4, and b is a value of 0 or 1. 
     
     
         12 . The composition of  claim 10  wherein the polycyclic, heteroatom-containing, hydrocarbon compound comprises phenothiazine, a derivative of phenothiazine, 2-methylthiophenothiazine, 10-methylphenothiazine, monotetradecylphenothiazine, ditetradecylphenothiazine, monodecylphenothiazine, didecylphenothiazine, monononylphenothiazine, dinonylphenothiazine, monoctylphenothiazine, dioctylphenothiazine, monobutylphenothiazine, dibutylphenothiazine, monostyrylphenothiazine, distyrylphenothiazine, butyloctylphenothiazine, styryloctylphenothiazine, and mixtures thereof. 
     
     
         13 . The composition of  claim 12  which comprises an alkylated phenothiazine, an alkylated derivative of phenothiazine, or mixtures thereof. 
     
     
         14 . The composition of  claim 9  wherein the one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds comprise monoalkylated polycyclic, heteroatom-containing, hydrocarbon compounds and dialkylated polycyclic, heteroatom-containing, hydrocarbon compounds, wherein the ratio of monoalkylated polycyclic, heteroatom-containing, hydrocarbon compounds to dialkylated polycyclic, heteroatom-containing, hydrocarbon compounds is from 5:95 to 95:5. 
     
     
         15 . The composition of  claim 9  wherein the alkylated polycyclic, heteroatom-containing, hydrocarbon compounds have a quaternary carbon content from 50 percent to 100 percent, based on the total primary, secondary, tertiary and quaternary carbons in the alkylated polycyclic, heteroatom-containing, hydrocarbon compounds. 
     
     
         16 . The composition of  claim 9  which is selected from a polycyclic, heteroatom-containing, hydrocarbon compound-containing mPAO dimer, trimer, tetramer, pentamer, hexamer and higher oligomer. 
     
     
         17 . The composition of  claim 9  wherein the process is carried out under reaction conditions sufficient to couple the polyalphaolefin oligomer or α-olefin (C 4 -C 40 ) with at least one polycyclic, heteroatom-containing, hydrocarbon compound, to produce said one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds. 
     
     
         18 . The composition of  claim 9  wherein the catalyst comprises a Bronsted acid, a Lewis acid, an aluminum silicate, an ion exchange resin, a zeolite, a naturally occurring sheet silicate, a modified sheet silicate, and an acidic ionic liquid. 
     
     
         19 . A process for producing a composition comprising one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds, said process comprising reacting a polyalphaolefin oligomer or α-olefin (C 4 -C 40 ) with at least one polycyclic, heteroatom-containing, hydrocarbon compound, in the presence of a catalyst, under reaction conditions sufficient to produce said composition. 
     
     
         20 . The process of  claim 19  which is carried out under reaction conditions sufficient to couple the polyalphaolefin oligomer or α-olefin (C 4 -C 40 ) with the at least one polycyclic, heteroatom-containing, hydrocarbon compound, to produce said composition. 
     
     
         21 . The process of  claim 19  wherein the catalyst comprises a Bronsted acid, a Lewis acid, an aluminum silicate, an ion exchange resin, a zeolite, a naturally occurring sheet silicate, a modified sheet silicate, and an acidic ionic liquid. 
     
     
         22 . The process of  claim 19  wherein the polyalphaolefin oligomer is selected from a mPAO dimer (C 6 -C 40 ), trimer (C 6 -C 40 ), tetramer (C 6 -C 40 ), pentamer (C 6 -C 40 ), and hexamer (C 6 -C 40 ), and the at least one polycyclic, heteroatom-containing, hydrocarbon compound is selected from phenothiazine, phenyl phenothiazine, 2-methylthiophenothiazine, 10-methylphenothiazine, monotetradecylphenothiazine, ditetradecylphenothiazine, monodecylphenothiazine, didecylphenothiazine, monononylphenothiazine, dinonylphenothiazine, monoctylphenothiazine, dioctylphenothiazine, monobutylphenothiazine, dibutylphenothiazine, monostyrylphenothiazine, distyrylphenothiazine, butyloctylphenothiazine, styryloctylphenothiazine, and mixtures thereof. 
     
     
         23 . The process of  claim 19  wherein the one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds are represented by the formula
   (R 1 ) a (X)(R 2 ) b    
 
       wherein R 1  and R 2  are the same or different and are the residue of an alkyl group having from 4 to 40 carbon atoms, X is the residue of at least one polycyclic, heteroatom-containing, hydrocarbon compound, a is a value from 1 to 8, and b is a value from 0 to 8; wherein said alkylated polycyclic, heteroatom-containing, hydrocarbon compounds have a viscosity (Kv 100 ) from 2 to 300 at 100° C. as determined by ASTM D-445, and a viscosity index (VI) from −100 to 300 as determined by ASTM D-2270. 
     
     
         24 . The process of  claim 23  wherein R 1  and R 2  are selected from the residue of a mPAO dimer (C 6 -C 40 ), trimer (C 6 -C 40 ), tetramer (C 6 -C 40 ), pentamer (C 6 -C 40 ), and hexamer (C 6 -C 40 ), or α-olefin (C 4 -C 40 ), X is selected from the residue of at least one of phenothiazine and phenyl phenothiazine, a is a value from 1 to 4, and b is a value of 0 or 1. 
     
     
         25 . The process of  claim 23  wherein the polycyclic, heteroatom-containing, hydrocarbon compound comprises phenothiazine, a derivative of phenothiazine, 2-methylthiophenothiazine, 10-methylphenothiazine, monotetradecylphenothiazine, ditetradecylphenothiazine, monodecylphenothiazine, didecylphenothiazine, monononylphenothiazine, dinonylphenothiazine, monoctylphenothiazine, dioctylphenothiazine, monobutylphenothiazine, dibutylphenothiazine, monostyrylphenothiazine, distyrylphenothiazine, butyloctylphenothiazine, styryloctylphenothiazine, and mixtures thereof. 
     
     
         26 . The process of  claim 25  wherein the composition comprises an alkylated phenothiazine, an alkylated derivative of phenothiazine, or mixtures thereof. 
     
     
         27 . The process of  claim 19  wherein the one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds comprise monoalkylated polycyclic, heteroatom-containing, hydrocarbon compounds and dialkylated polycyclic, heteroatom-containing, hydrocarbon compounds, wherein the ratio of monoalkylated polycyclic, heteroatom-containing, hydrocarbon compounds to dialkylated polycyclic, heteroatom-containing, hydrocarbon compounds is from 5:95 to 95:5. 
     
     
         28 . The process of  claim 19  wherein the one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds have a quaternary carbon content from 50 percent to 100 percent, based on the total primary, secondary, tertiary and quaternary carbons in the one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds. 
     
     
         29 . The process of  claim 19  wherein the composition is selected from a polycyclic, heteroatom-containing, hydrocarbon compound-containing mPAO dimer, trimer, tetramer, pentamer, hexamer and higher oligomer. 
     
     
         30 . A lubricating oil base stock comprising one or more compounds represented by the formula
   (R 1 ) a (X)(R 2 ) b      
       wherein R 1  and R 2  are the same or different and are the residue of an alkyl group having from 4 to 40 carbon atoms, X is the residue of at least one polycyclic, heteroatom-containing, hydrocarbon compound, a is a value from 1 to 8, and b is a value from 0 to 8; wherein said compounds have a viscosity (Kv 100 ) from 2 to 300 at 100° C. as determined by ASTM D-445, and a viscosity index (VI) from −100 to 300 as determined by ASTM D-2270. 
     
     
         31 . The lubricating oil base stock of  claim 30  wherein R 1  and R 2  are selected from the residue of a mPAO dimer (C 6 -C 40 ), trimer (C 6 -C 40 ), tetramer (C 6 -C 40 ), pentamer (C 6 -C 40 ), and hexamer (C 6 -C 40 ), or α-olefin (C 4 -C 40 ), X is selected from the residue of at least one of phenothiazine and phenyl phenothiazine, a is a value from 1 to 4, and b is a value of 0 or 1. 
     
     
         32 . The lubricating oil base stock of  claim 30  wherein the polycyclic, heteroatom-containing, hydrocarbon compound comprises phenothiazine, a derivative of phenothiazine, 2-methylthiophenothiazine, 10-methylphenothiazine, monotetradecylphenothiazine, ditetradecylphenothiazine, monodecylphenothiazine, didecylphenothiazine, monononylphenothiazine, dinonylphenothiazine, monoctylphenothiazine, dioctylphenothiazine, monobutylphenothiazine, dibutylphenothiazine, monostyrylphenothiazine, distyrylphenothiazine, butyloctylphenothiazine, styryloctylphenothiazine, and mixtures thereof. 
     
     
         33 . The lubricating oil base stock of  claim 30  which comprises one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds. 
     
     
         34 . The lubricating oil base stock of  claim 30  which comprises an alkylated phenothiazine, an alkylated derivative of phenothiazine, or mixtures thereof. 
     
     
         35 . The lubricating oil base stock of  claim 33  wherein the one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds comprise monoalkylated polycyclic, heteroatom-containing, hydrocarbon compounds and dialkylated polycyclic, heteroatom-containing, hydrocarbon compounds, wherein the ratio of monoalkylated polycyclic, heteroatom-containing, hydrocarbon compounds to dialkylated polycyclic, heteroatom-containing, hydrocarbon compounds is from 5:95 to 95:5. 
     
     
         36 . The lubricating oil base stock of  claim 33  wherein the alkylated polycyclic, heteroatom-containing, hydrocarbon compounds have a quaternary carbon content from 50 percent to 100 percent, based on the total primary, secondary, tertiary and quaternary carbons in the alkylated polycyclic, heteroatom-containing, hydrocarbon compounds. 
     
     
         37 . The lubricating oil base stock of  claim 30  which is selected from a polycyclic, heteroatom-containing, hydrocarbon compound-containing mPAO dimer, trimer, tetramer, pentamer, hexamer and higher oligomer. 
     
     
         38 . A lubricating oil comprising a lubricating oil base stock as a major component, and a polycyclic, heteroatom-containing, hydrocarbon compound cobase stock as a minor component; wherein said polycyclic, heteroatom-containing, hydrocarbon compound cobase stock comprises one or more compounds represented by the formula
   (R 1 ) a (X)(R 2 ) b      
       wherein R 1  and R 2  are the same or different and are the residue of an alkyl group having from 4 to 40 carbon atoms, X is the residue of at least one polycyclic, heteroatom-containing, hydrocarbon compound, a is a value from 1 to 8, and b is a value from 0 to 8; wherein said polycyclic, heteroatom-containing, hydrocarbon compound cobase stock has a viscosity (Kv 100 ) from 2 to 300 at 100° C. as determined by ASTM D-445, and a viscosity index (VI) from −100 to 300 as determined by ASTM D-2270. 
     
     
         39 . The lubricating oil of  claim 38  wherein the lubricating oil base stock comprises a Group I, II, III, IV or V base oil stock. 
     
     
         40 . The lubricating oil of  claim 38  wherein the lubricating oil base stock comprises a polyalphaolefin (PAO) or gas-to-liquid (GTL) oil base stock. 
     
     
         41 . The lubricating oil of  claim 38  wherein the lubricating oil base stock is present in an amount from 50 weight percent to 99 weight percent, and the polycyclic, heteroatom-containing, hydrocarbon compound cobase stock is present in an amount from 1 weight percent to 50 weight percent, based on the total weight of the lubricating oil. 
     
     
         42 . The lubricating oil of  claim 38  wherein R 1  and R 2  are selected from the residue of a mPAO dimer (C 6 -C 40 ), trimer (C 6 -C 40 ), tetramer (C 6 -C 40 ), pentamer (C 6 -C 40 ), and hexamer (C 6 -C 40 ), or α-olefin (C 4 -C 40 ), X is selected from the residue of at least one of phenothiazine and phenyl phenothiazine, a is a value from 1 to 4, and b is a value of 0 or 1. 
     
     
         43 . The lubricating oil of  claim 38  wherein the polycyclic, heteroatom-containing, hydrocarbon compound comprises phenothiazine, a derivative of phenothiazine, 2-methylthiophenothiazine, 10-methylphenothiazine, monotetradecylphenothiazine, ditetradecylphenothiazine, monodecylphenothiazine, didecylphenothiazine, monononylphenothiazine, dinonylphenothiazine, monoctylphenothiazine, dioctylphenothiazine, monobutylphenothiazine, dibutylphenothiazine, monostyrylphenothiazine, distyrylphenothiazine, butyloctylphenothiazine, styryloctylphenothiazine, and mixtures thereof. 
     
     
         44 . The lubricating oil of  claim 38  wherein said polycyclic, heteroatom-containing, hydrocarbon compound cobase stock comprises one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds. 
     
     
         45 . The lubricating oil of  claim 38  wherein said polycyclic, heteroatom-containing, hydrocarbon compound cobase stock comprises an alkylated phenothiazine, an alkylated derivative of phenothiazine, or mixtures thereof. 
     
     
         46 . The lubricating oil of  claim 44  wherein the one or more alkylated polycyclic, heteroatom-containing, hydrocarbon compounds comprise monoalkylated polycyclic, heteroatom-containing, hydrocarbon compounds and dialkylated polycyclic, heteroatom-containing, hydrocarbon compounds, wherein the ratio of monoalkylated polycyclic, heteroatom-containing, hydrocarbon compounds to dialkylated polycyclic, heteroatom-containing, hydrocarbon compounds is from 5:95 to 95:5. 
     
     
         47 . The lubricating oil of  claim 44  wherein the alkylated polycyclic, heteroatom-containing, hydrocarbon compounds have a quaternary carbon content from 50 percent to 100 percent, based on the total primary, secondary, tertiary and quaternary carbons in the alkylated polycyclic, heteroatom-containing, hydrocarbon compounds. 
     
     
         48 . The lubricating oil of  claim 38  wherein said polycyclic, heteroatom-containing, hydrocarbon compound cobase stock is selected from a polycyclic, heteroatom-containing, hydrocarbon compound-containing mPAO dimer, trimer, tetramer, pentamer, hexamer and higher oligomer. 
     
     
         49 . The lubricating oil of  claim 38  wherein the polycyclic, heteroatom-containing, hydrocarbon compound cobase stock comprises a polycyclic, heteroatom-containing, hydrocarbon compound-containing polyalphaolefin oligomer. 
     
     
         50 . The lubricating oil of  claim 38  wherein the polycyclic, heteroatom-containing, hydrocarbon compound cobase stock is formed from the reaction of a polyalphaolefin dimer, trimer or tetramer with phenothiazine or derivative of phenothiazine. 
     
     
         51 . The lubricating oil of  claim 38  wherein the lubricating oil further comprises one or more of a viscosity improver, antioxidant, detergent, dispersant, pour point depressant, corrosion inhibitor, metal deactivator, seal compatibility additive, anti-foam agent, inhibitor, and anti-rust additive. 
     
     
         52 . A method for improving oxidative stability of a lubricating oil by using as the lubricating oil a formulated oil comprising a lubricating oil base stock as a major component, and polycyclic, heteroatom-containing, hydrocarbon compound cobase stock as a minor component; wherein said polycyclic, heteroatom-containing, hydrocarbon compound cobase stock comprises one or more compounds represented by the formula
   (R 1 ) a (X)(R 2 ) b      
       wherein R 1  and R 2  are the same or different and are the residue of an alkyl group having from 4 to 40 carbon atoms, X is the residue of at least one polycyclic, heteroatom-containing, hydrocarbon compound, a is a value from 1 to 8, and b is a value from 0 to 8; wherein said polycyclic, heteroatom-containing, hydrocarbon compound cobase stock has a viscosity (Kv 100 ) from 2 to 300 at 100° C. as determined by ASTM D-445, a viscosity index (VI) from −100 to 300 as determined by ASTM D-2270, and an oxidation onset temperature (OOT)/oxidation peak temperature (OPT) ranging from 175° C./325° C. to 225° C./375° C.; wherein oxidative stability is improved as compared to oxidative stability achieved using a lubricating engine oil containing a minor component other than the polycyclic, heteroatom-containing, hydrocarbon compound cobase stock. 
     
     
         53 . A composition comprising one or more compounds represented by the formula 
       
         
           
           
               
               
           
         
       
       wherein R′ 1  and R′ 2  are the same or different and are hydrogen or the residue of an alkyl group having from 1 to 40 carbon atoms, R′ 3  and R′ 4  are the same or different and are the residue of an alkyl group having from 1 to 40 carbon atoms; wherein the composition has a viscosity (Kv 100 ) from 2 to 300 at 100° C. as determined by ASTM D-445, and a viscosity index (VI) from −100 to 300 as determined by ASTM D-2270. 
     
     
         54 . A lubricating oil base stock comprising one or more compounds represented by the formula 
       
         
           
           
               
               
           
         
       
       wherein R′ 1  and R′ 2  are the same or different and are hydrogen or the residue of an alkyl group having from 1 to 40 carbon atoms, R′ 3  and R′ 4  are the same or different and are the residue of an alkyl group having from 1 to 40 carbon atoms; wherein the composition has a viscosity (Kv 100 ) from 2 to 300 at 100° C. as determined by ASTM D-445, and a viscosity index (VI) from −100 to 300 as determined by ASTM D-2270. 
     
     
         55 . The composition of  claim 1  wherein the polycyclic, heteroatom-containing, hydrocarbon compound is represented by the formula 
       
         
           
           
               
               
           
         
       
       wherein R′ 1  and R′ 2  are the same or different and are hydrogen or the residue of an alkyl group having from 1 to 40 carbon atoms. 
     
     
         56 . The lubricating oil base stock of  claim 30  wherein the polycyclic, heteroatom-containing, hydrocarbon compound is represented by the formula 
       
         
           
           
               
               
           
         
       
       wherein R′ 1  and R′ 2  are the same or different and are hydrogen or the residue of an alkyl group having from 1 to 40 carbon atoms. 
     
     
         57 . A lubricating oil comprising the lubricating oil base stock of  claim 30  which is present in an amount from 20 weight percent to 80 weight percent, based on the total weight of the lubricating oil.