Amination of polymers terminated with aldehyde group and their functionalized derivatives for fouling mitigation in hydrocarbon refining processes

A method for preparing compound, comprising:

• (a) converting a polymer base unit R11 which is a branched or straight-chained C10-C800 alkyl or alkenyl group having a vinyl terminal group, to a polymer having an aldehyde terminal group;
• (b) reacting the polymer having the aldehyde terminal group obtained in (a) with a polyamine represented by
• to form an imine intermediate, wherein in Formula II:
• R12 is hydrogen or a C1-C4 branched or straight chained alkyl optionally substituted with one or more amine groups, R13 is a C1-C4 branched or straight chained alkylene group, and x is an integer between 1 and 10, and further wherein the —N(R12)—R13— unit is optionally interrupted in one or more places by a nitrogen-containing heterocyclic group, and wherein when the x-th —N(R12)—R13— unit along with the terminal nitrogen atom forms a heterocyclic cycloalkyl group, the terminal —NH2 is replaced by a —NH— group for valency;
• and
• (c) reducing the imine intermediate to form a product with a saturated C—N bond.

A compound produced by the method comprising:

• (a) converting a polymer base unit R11, which is a branched or straight-chained C10-C800 alkyl or alkenyl group having a vinyl terminal group, to a polymer having an aldehyde terminal group;
• (b) reacting the polymer having the aldehyde terminal group obtained in (a) with a polyamine represented by
• to generate an imine intermediate, wherein R12 is hydrogen or a C1-C4 branched or straight chained alkyl optionally substituted with one or more amine groups, R13 is a C1-C4 branched or straight chained alkylene group, and x is an integer between 1 and 10, and further wherein the —N(R12)—R13— unit is optionally interrupted in one or more places by a nitrogen-containing heterocyclic group, and wherein when the x-th —N(R12)—R13— unit along with the terminal nitrogen atom forms a heterocyclic cycloalkyl group, the terminal —NH2 is replaced by a —NH— group for valency;
• and
• (c) reducing the imine intermediate to form a product with a saturated C—N bond.

A method for reducing fouling in a hydrocarbon refining process comprising providing a crude hydrocarbon for a refining process;

• adding an additive to the crude hydrocarbon, the additive being represented by
• wherein R1 is a branched or straight-chained C10-C800 alkyl or alkenyl group;
• m is an integer between 0 and 10 inclusive;
• R2 is represented by
• or —CH2—CH2—CH2—CH2—*, wherein the asterisk (*) indicates a connecting point of R2 with the nitrogen that connects with R3;
• R3 is a C1-C4 branched or straight chained alkylene group;
• R31 is hydrogen or —R8—R9, wherein R8 is defined the same as R2 above, and R9 is branched or straight-chained C10-C800 alkyl or alkenyl group, or R8 and R9 together are a C1-C4 branched or straight chained alkyl group optionally substituted with one or more amine groups;
• and further wherein the —N(R31)—R3— repeat unit is optionally interrupted in one or more places by a nitrogen-containing heterocyclic cycloalkyl group;
• and
• R4 and R5 are each independently selected from (a) hydrogen, (b) —R6—R7, wherein R6 is defined the same as R2 above, and R7 is a C10-C800 branched or straight chained alkyl or alkenyl group, or (c) a bond connected to R31 in the m-th —N(R31)—R3— repeat unit.

A system for refining hydrocarbons comprising:

• at least one crude hydrocarbon refinery component;
• and
• crude hydrocarbon in fluid communication with the at least one crude hydrocarbon refinery component, the crude hydrocarbon comprising an additive represented by
• wherein R1 is a branched or straight-chained C10-C800 alkyl or alkenyl group;
• m is an integer between 0 and 10 inclusive;
• R2 is represented by
• or —CH2—CH2—CH2—CH2—*, wherein the asterisk (*) indicates a connecting point of R2 with the nitrogen that connects with R3;
• R3 is a C1-C4 branched or straight chained alkylene group;
• R31 is hydrogen or —R8—R9, wherein R8 is defined the same as R2 above, and R9 is branched or straight-chained C10-C800 alkyl or alkenyl group, or R8 and R9 together are a C1-C4 branched or straight chained alkyl group optionally substituted with one or more amine groups;
• and further wherein the —N(R31)—R3— repeat unit is optionally interrupted in one or more places by a nitrogen-containing heterocyclic cycloalkyl group;
• and
• R4 and R5 are each independently selected from (a) hydrogen, (b) —R6—R7, wherein R6 is defined the same as R2 above, and R7 is a C10-C800 branched or straight chained alkyl or alkenyl group, or (c) a bond connected to R31 in the m-th —N(R31)—R3— repeat unit.