Processes and systems for forming functionalized organic sulfides

A solvent-free process for forming a functionalized organic sulfide, the solvent-free process comprising:

• heating or maintaining, in a reactor, an olefin at a temperature in a range from about 20° C. to about 180° C., the olefin represented by formula (I):
• wherein each of R1a, R1b, R2a, and R2b of formula (I) is, independently, hydrogen, or a C1-C20 unsubstituted hydrocarbyl, or two or more of R1a, R1b, R2a, and R2b join to form a ring;
• introducing a mercaptan to the olefin represented by formula (I) to form a mixture, the mercaptan represented by formula (II):
• wherein R3 of formula (II) is a C1-C24 substituted hydrocarbyl;
• and
• wherein a molar ratio of the olefin represented by formula (I) to the mercaptan represented by formula (II) in the mixture is within a range from about 1:1 to about 10:1;
• reacting the mixture, under conversion conditions, to form a conversion product effluent comprising a functionalized organic sulfide and unreacted olefin represented by formula (I), the conversion conditions comprising:
• exposing the mixture to a first gas comprising air, O2, or a combination thereof;
• and
• exposing the mixture to a second gas, the second gas being different from the first gas, the second gas comprising a non-reactive gas;
• separating the unreacted olefin from the conversion product effluent;
• and
• combining the unreacted olefin with the mercaptan represented by formula (II) in the reactor.

A system for forming a functionalized organic sulfide, the system comprising:

• a reactor;
• a separation unit;
• and
• a controller, the reactor and the separation unit coupled to the controller, the controller configured:
• to cause the reactor to receive a first feed comprising an olefin, to heat the first feed, to receive a second feed comprising a mercaptan, to react a mixture comprising the first feed and the second feed under conversion conditions, and to discharge a conversion product effluent comprising a functionalized organic sulfide and unreacted olefin;
• and
• to cause the separation unit to receive the conversion product effluent and to separate the conversion product effluent into a plurality of output streams, a first output stream of the plurality of output streams comprising the unreacted olefin.