Process for producing middle distillate by alkylating C5+ isoparaffin and C5+ olefin

An alkylation process, comprising:

• a. contacting a naphtha comprising C5+ isoparaffins and having a RON less than 70, and
• a hydrocarbon stream comprising C5 olefins with an acidic haloaluminate ionic liquid catalyst in an alkylation reactor under alkylation conditions to produce an alkylate product, wherein the acidic haloaluminate ionic liquid catalyst has the general formula RR′ R″ N H+ Al2Cl7—, and wherein RR′ and R″ are alkyl groups containing 1 to 12 carbons, and where RR′ and R″ may or may not be the same;
• b. adjusting over time a level of a halide containing additive provided to the ionic liquid alkylation reactor to improve a selectivity of the acidic haloaluminate ionic liquid catalyst;
• and
• c. recovering a middle distillate from the alkylate product, wherein the middle distillate comprises less than 3 wt % olefin prior to any optional hydrofinishing.

An alkylation process, comprising:

• a. providing an isoparaffin feed that comprises at least 50 wt % C5+;
• b. providing a hydrocarbon stream that comprises at least 20 wt % C5+ olefins;
• c. contacting the isoparaffin feed and the hydrocarbon stream with an acidic haloaluminate ionic liquid catalyst in an alkylation zone under alkylation conditions wherein a middle distillate is produced;
• d. adjusting over time a level of a halide containing additive provided to the alkylation zone to improve a selectivity of the acidic haloaluminate ionic liquid catalyst;
• wherein the middle distillate has less than 10 ppm sulfur and less than 3 wt % olefin, prior to any optional hydrofinishing;
• and wherein the acidic haloaluminate ionic liquid catalyst is an alkyl substituted pyridinium chloroaluminate or an alkyl substituted imidazolium chloroaluminate of the general formula A and B, respectively,
• where R, R1, R2, and R3═H, methyl, ethyl, propyl, butyl, pentyl or hexyl group, and X is a chloroaluminate, and where R, R1, R2 and R3 may or may not be the same.

An alkylation process, comprising:

• a. contacting a naphtha comprising C5+ isoparaffins and having a RON less than 70, and a hydrocarbon stream comprising C5 olefins with an acidic haloaluminate ionic liquid catalyst in an alkylation reactor under alkylation conditions to produce an alkylate product, wherein the acidic haloaluminate ionic liquid catalyst is an alkyl substituted pyridinium chloroaluminate or an alkyl substituted imidazolium chloroaluminate of the general formula A and B, respectively,
• where R, R1, R2, and R3═H, methyl, ethyl, propyl, butyl, pentyl or hexyl group, and X is a chloroaluminate, and where R, R1, R2 and R3 may or may not be the same;
• b. adjusting over time a level of a halide containing additive provided to the ionic liquid alkylation reactor to improve a selectivity of the acidic haloaluminate ionic liquid catalyst;
• and
• c. recovering a middle distillate from the alkylate product, wherein the middle distillate comprises less than 3 wt % olefin prior to any optional hydrofinishing.