Alkyl poly glycol-ethers and their synthesis

A process to make a long chain ether lubricant, comprising:

• a) contacting at least one fatty acid with a ketonization catalyst in a ketonization zone under ketonization conditions to provide a long chain ketone according to the following Scheme 1:
• R1COOH+R2COOH→R1C(O)R2+CO2+H2O
• wherein R1 and R2 are independently selected from the group consisting of C5-C21 linear or branched alkyl and C5-C21 linear or branched alkenyl;
• b) contacting the long chain ketone with a selective ketone hydrogenation catalyst in a ketone hydrogenation zone in the presence of hydrogen gas under selective ketone hydrogenation conditions to provide a long chain secondary alcohol according to the following Scheme 2:
• R1C(O)R2+H2→R1′CH(OH)R2′
• wherein:
• R1 and R2 are the same or different,
• when R1 is alkyl R1′═R1,
• when R2 is alkyl R2′═R2,
• when R1 is alkenyl R1′ is alkyl or alkenyl,
• when R2 is alkenyl R2′ is alkyl or alkenyl,
• R1 and R1′ have an equal number of carbon atoms, and
• R2 and R2′ have an equal number of carbon atoms;
• c) providing a first reactant comprising a material selected from the group consisting of the long chain secondary alcohol, a long chain alkoxide, and combinations thereof;
• d) reacting the first reactant with at least a first epoxide to form a long chain ether intermediate selected from the group consisting of a long chain ether alcoholate of general Formula IIA, a long chain ether alcohol of general Formula IIB, and combinations thereof:
• wherein:
• R1′ and R2′ are independently selected from the group consisting of C5-C21 linear or branched alkyl and C5-C21 linear or branched alkenyl,
• R3 and R4 are independently selected from the group consisting of a hydrogen atom, C1-C35 linear or branched alkyl, and aryl,
• n is an integer from 1 to 50;
• and
• e) preparing the long chain ether lubricant from the long chain ether intermediate;
• wherein the long chain ether lubricant has a Viscosity Index from 120 to 230.

A process to make a long chain ether lubricant, comprising:

• a) contacting at least one fatty acid with a ketonization catalyst in a ketonization zone under ketonization conditions to provide a long chain ketone according to the following Scheme 1:
• R1COOH+R2COOH→R1C(O)R2+CO2+H2O
• wherein R1 and R2 are independently selected from the group consisting of C5-C21 linear or branched alkyl and C5-C21 linear or branched alkenyl, and
• b) contacting the long chain ketone with a selective ketone hydrogenation catalyst in a ketone hydrogenation zone in the presence of hydrogen gas under selective ketone hydrogenation conditions to provide the long chain secondary alcohol according to the following Scheme 2:
• R1C(O)R2+H2→R1′CH(OH)R2′
• wherein:
• R1 and R2 are the same or different,
• when R1 is alkyl R1′═R1,
• when R2 is alkyl R2′═R2,
• when R1 is alkenyl R1′ is alkyl or alkenyl,
• when R2 is alkenyl R2′ is alkyl or alkenyl,
• R1 and R1′ have an equal number of carbon atoms, and
• R2 and R2′ have an equal number of carbon atoms;
• and
• c) converting at least a portion of the long chain secondary alcohol to a long chain alkoxide;
• d) reacting the long chain alkoxide with at least a first epoxide to provide a long chain ether intermediate consisting of a long chain ether alcoholate of general Formula IIA:
• e) reacting the long chain ether alcoholate with an alkyl halide to form the long chain ether lubricant according to the following Scheme 6:
• wherein:
• R′ is selected from the group consisting of C1-C22 linear or branched alkyl and C2-C22 linear or branched alkenyl, X is a halogen atom, R1′ and R2′ are independently selected from the group consisting of C5-C21 linear or branched alkyl and C5-C21 linear or branched alkenyl,
• R3 and R4 are independently selected from the group consisting of a hydrogen atom, C1-C35 linear or branched alkyl, and aryl, and
• n is an integer from 1 to 50;
• and
• wherein the long chain ether lubricant has a Viscosity Index from 120 to 230.