Reacting cyclopentadiene and maleic anhydride for the production of plasticizers

A process for making multi-esters comprising:

• reacting cyclopentadiene with maleic anhydride to form compounds of the following formula (I):
• optionally conducting a first esterification step by contacting said compounds of formula (I) with at least one C4 to C13 OXO-alcohol of the formula R1OH under esterification conditions to form compounds of the following formula (II):
• wherein R1 is a hydrocarbon residue of the OXO-alcohol R1OH;
• hydroformylating said compounds of formulae (I) or (II), and oxidizing said hydroformylated compounds to form multi-functional compounds of the following formula (IIa):
• wherein R′ can be H or R1;
• and
• reacting said multi-functional compounds of formula (IIa) with OXO-alcohols of the formula R1OH if R′ is H, or if R′ is R1 with an OXO-alcohol of the formula R3OH, under esterification conditions to form tri-esters of the following formula:
• wherein each R1 and R3 are the same or different hydrocarbon residues of said C4 to C13 OXO-alcohols averaging from 0.2 to 5.0 branches per residue.

A process for making multi-esters comprising:

• contacting maleic anhydride with at least one C4 to C13 OXO-alcohol of the formula R1OH under esterification conditions to form compounds of the following formula (III):
• reacting the compounds of formula (III) with cyclopentadiene to form compounds of the following formula (II):
• hydroformylating said compounds of formula (II), and oxidizing said hydroformylated compounds to form multi-functional compounds of the following formula (IIb):
• and
• reacting said multi-functional compounds of formula (IIb) with an OXO-alcohol of the formula R3OH, under esterification conditions to form tri-esters of the following formula:
• wherein each R1 and R3 are the same or different hydrocarbon residues of said C4 to C13 OXO-alcohols averaging from 0.2 to 5.0 branches per residue.

A process for making multi-esters comprising:

• reacting cyclopentadiene with maleic anhydride to form compounds of the following formula (I):
• reacting the compounds of formula (I) with CO and OXO-alcohols of the formula R1OH if R′ is H, or if R′ is R with an OXO-alcohol of the formula R3OH, in the presence of a metal catalyst to form compounds of the following formula (IV):
• reacting the compounds of formula (IV) with OXO-alcohols of the formula R1OH if R′ is H, or if R′ is R1 with an OXO-alcohol of the formula R3OH, under esterification conditions to form tri-esters of the following formula:
• wherein each R1 and R3 are the same or different hydrocarbon residues of said C4 to C13 OXO-alcohols averaging from 0.2 to 5.0 branches per residue.

A process for making multi-esters comprising:

• reacting cyclopentadiene with maleic anhydride to form compounds of the following formula (I):
• conducting a first esterification step by contacting said compounds of formula (I) with at least one C4 to C13 OXO-alcohol of the formula R1OH under esterification conditions to form compounds of the following formula (II):
• wherein R1 is a hydrocarbon residue of the OXO-alcohol R1OH;
• reacting the compounds of formula (II) with CO and OXO-alcohols of the formula R1OH if R′ is H, or if R′ is R1 with an OXO-alcohol of the formula R3OH, in the presence of a metal catalyst to form tri-esters of the following formula:
• wherein each R1 and R3 are the same or different hydrocarbon residues of said C4 to C13 OXO-alcohols averaging from 0.2 to 5.0 branches per residue.

A process for making multi-esters comprising:

• contacting maleic anhydride with at least one C4 to C13 OXO-alcohol of the formula R1OH under esterification conditions to form compounds of the following formula (III):
• reacting the compounds of formula (III) with cyclopentadiene to form compounds of the following formula (II):
• reacting the compounds of formula (II) with CO and OXO-alcohols of the formula R1OH if R′ is H, or if R′ is R1 with an OXO-alcohol of the formula R3OH, in the presence of a metal catalyst to form tri-esters of the following formula:
• wherein each R1 and R3 are the same or different hydrocarbon residues of said C4 to C13 OXO-alcohols averaging from 0.2 to 5.0 branches per residue.