Alkylaromatic lubricant fluids

Abstract

The alkylaromatic compositions include an aromatic moiety other than unsubstituted naphthalene; and an alkyl moiety having a carbon atom number in the range between 12 to 40, wherein said alkyl moiety is attached to said aromatic moiety such that at least 25 mol % of the benzylic carbons are quaternary. The process for producing the alkylaromatic compositions include contacting at least one an aromatic compound and a mono-olefin having a carbon atom number in the range between 12 to 40 in the presence of an acidic alkylation catalyst under alkylation conditions, wherein at least 50 mol % of the mono-olefin structure comprises a vinylidenyl structure, and thereby producing said alkylaromatic compound having at least 25 mol % of benzylic carbons that are quaternary. The alkylaromatic compositions disclosed herein are liquids that have improved thermo- and oxidative stability and pour point.

1 . An alkylaromatic composition comprising:
 an aromatic moiety other than unsubstituted naphthalene; and   an alkyl moiety having a carbon atom number in the range between 12 to 40, wherein said alkyl moiety is attached to said aromatic moiety such that at least 25 mol % of the benzylic carbons are quaternary.   
     
     
         2 . The alkylaromatic composition of  claim 1 , wherein at least 35 mol % of the benzylic carbons are quaternary. 
     
     
         3 . The alkylaromatic composition of  claim 1 , wherein at least 70 mol % of the benzylic carbons are quaternary. 
     
     
         4 . The alkylaromatic composition of  claim 1 , wherein said aromatic moiety is chosen from benzene, toluene, xylenes, ethylbenzene naphthalene, diphenyl sulfide, diphenyl oxide, and mixtures thereof. 
     
     
         5 . The alkylaromatic composition of  claim 1 , wherein said aromatic moiety is chosen from substituted or unsubstituted benzene, substituted naphthalene, substituted or unsubstituted furan, substituted or unsubstituted thiophene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrole, substituted or unsubstituted indole, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzofuran, substituted or unsubstituted dibenzofuran, substituted or unsubstituted phenoxanthiin, substituted or unsubstituted thianthrene, substituted or unsubstituted biphenyl, substituted or unsubstituted pyrene, bisphenol A, bisphenol sulfide, anisole, thioanisole, diphenyl oxide, diphenyl sulfide, diphenylmethane, and mixtures thereof. 
     
     
         6 . The alkylaromatic composition of  claim 1 , wherein said aromatic moiety is chosen from toluene, o-, m- or p-xylene, hydroxybenzene, methoxy or ethoxybenzene, thioanisole, diphenylether, diphenylmethane, diphenyl sulfide, methylnaphthalene, methoxynaphthalene, ethoxynaphthalene, methylnaphthal sulfide, ethyl naphthylsulfide, bisphenol-A, bisphenol sulfide and mixtures thereof. 
     
     
         7 . The alkylaromatic composition of  claim 1 , wherein said alkyl moiety has a carbon atom number in the range between 16 to 24. 
     
     
         8 . The alkylaromatic composition of  claim 4 , wherein said aromatic moiety is toluene. 
     
     
         9 . The alkylaromatic composition of  claim 8 , wherein said composition has an oxidative stability as measured by RBOT of greater than 30 minutes. 
     
     
         10 . The alkylaromatic composition of  claim 4 , wherein said aromatic moiety is benzene. 
     
     
         11 . The alkylaromatic composition of  claim 10 , wherein said composition has an oxidative stability as measured by RBOT of greater than 20 minutes. 
     
     
         12 . The alkylaromatic composition of  claim 1 , wherein said composition has a pour point of less than or equal to −35° C. 
     
     
         13 . The alkylaromatic composition of  claim 12 , wherein said composition has a pour point of less than or equal to −50° C. 
     
     
         14 . A process for the preparation of an alkylaromatic compound comprising: contacting at least one an aromatic compound and a mono-olefin having a carbon atom number in the range between 12 to 40 in the presence of an acidic alkylation catalyst under alkylation conditions, wherein at least 50 mol % of the mono-olefin structure comprises a vinylidenyl structure, and thereby producing said alkylaromatic compound having at least 25 mol % of benzylic carbons that are quaternary. 
     
     
         15 . The process according to  claim 14 , further comprising: separating and recovering said alkylaromatic compound. 
     
     
         16 . The process according to  claim 14 , wherein said alkylaromatic compounds has at least 65 mol % of benzylic carbons that are quaternary. 
     
     
         17 . The process according to  claim 14 , wherein said acidic alkylation catalyst is chosen from zeolite catalysts, MCM-22, MCM-57, MCM-36, MCM-49, MCM-56, ITQ-1, and ITQ-3. 
     
     
         18 . The process according to  claim 14 , wherein acidic alkylation catalyst is a Friedel Craft catalysts chosen from BF 3 , promoted BF 3 , AlCl 3 , SnCl 4 , FeCl 3 , and ZnCl 2 . 
     
     
         20 . The process according to  claim 14 , wherein said aromatic moiety is chosen from benzene, toluene, xylenes, ethylbenzene naphthalene, diphenyl sulfide, diphenyl oxide, and mixtures thereof. 
     
     
         21 . The process according to  claim 14 , wherein said aromatic moiety is chosen from substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted furan, substituted or unsubstituted thiophene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrole, substituted or unsubstituted indole, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzofuran, substituted or unsubstituted dibenzofuran, substituted or unsubstituted phenoxanthiin, substituted or unsubstituted thianthrene, substituted or unsubstituted biphenyl, substituted or unsubstituted pyrene, bisphenol A, bisphenol sulfide, anisole, thioanisole, diphenyl oxide, diphenyl sulfide, diphenylmethane, and mixtures thereof. 
     
     
         22 . The process according to  claim 14 , wherein said aromatic moiety is chosen from toluene, 0-, m- or p-xylene, hydroxybenzene, methoxy or ethoxybenzene, thioanisole, diphenylether, diphenylmethane, diphenyl sulfide, naphthalene, methylnaphthalene, methoxyhaphthalene, ethoxynaphthalene, methylnaphthal sulfide, ethyl naphthylsulfide, bisphenol-A, bisphenol sulfide and mixtures thereof. 
     
     
         23 . The process according to  claim 14 , wherein said mono-olefin has a carbon atom number in the range between 16 to 24. 
     
     
         24 . The process according to  claim 14 , wherein said alkyl moiety is derived from alkyl aluminum catalysts. 
     
     
         25 . The process according to  claim 24 , wherein said alkyl aluminum catalyst is triisobutyl aluminum. 
     
     
         26 . The process according to of  claim 14 , wherein said alkyl moiety is derived from a metallocene-catalyzed alpha-olefin polymerization process. 
     
     
         27 . The process according to  claim 24 , wherein said alkyl moiety is derived from a vinylidene with a carbon atom number less than 40. 
     
     
         28 . The process according to  claim 26 , wherein said alkyl moiety is derived from a vinylidene with a carbon atom number less than 40. 
     
     
         29 . The process according to  claim 27 , wherein said vinylidene is chosen from 2-hexyl-1-decene, 2-octyl-1-dodecene, or 2-decyl-1-tetradecene, and mixtures thereof. 
     
     
         30 . The process according to  claim 28 , wherein said vinylidene is chosen from 2-hexyl-1-decene, 2-octyl-1-dodecene, or 2-decyl-1-tetradecene, and mixtures thereof. 
     
     
         31 . The process according to  claim 14 , wherein at least 65 mol % of the mono-olefin structure comprises a vinylidenyl structure.