Production of substituted phenylene aromatic diesters
View Patent ↗The present disclosure is directed to the production of 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate and the purification thereof. Synthesis pathways for a precursor to 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate are provided. The precursor is 5-tert-butyl-3-methylcatechol.
1. A process comprising:
reacting, under reaction conditions, 5-tert-butyl-3-methylcatechol (BMC) with triethylamine and a member selected from the group consisting of an aromatic carboxylic acid and an aromatic carboxylic acid derivative; and
forming 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate (BMPD).
2. The process of claim 1 comprising adding benzoyl chloride to a reaction mixture comprising the BMC, acetonitrile and triethylamine; and forming the BMPD.
3. The process of claim 1 comprising adding water to the reaction mixture; and precipitating the BMPD.
4. The process of claim 1 comprising dissolving the precipitated BMPD and extracting with water.
5. The process of claim 1 comprising forming a BMPD composition comprising greater than 98 wt % BMPD.
6. The process of claim 1 further comprising:
alkylating, under reaction conditions, 3-methylcatechol with a member selected from the group consisting of tert-butanol and isobutylene; and
forming 5-tert-butyl-3-methylcatechol.
7. The process of claim 6 further comprising oxidizing, under reaction conditions, 2-hydroxy-3-methylbenzaldehyde; and
forming the 3-methylcatechol.
8. The process of claim 6 further comprising formylating, under reaction conditions, o-cresol with paraformaldehyde;
forming 2-hydroxy-3-methylbenzaldehyde;
oxidizing, under reaction conditions, the 2-hydroxy-3-methylbenzaldehyde; and
forming the 3-methylcatechol.
9. The process of claim 6 further comprising oxidizing, under reaction conditions, o-cresol; and
forming the 3-methylcatechol.
10. The process of claim 1 further comprising:
oxidizing, under reaction conditions, 5-tert-butyl-3-methyl-2-hydroxybenzaldehyde; and
forming 5-tert-butyl-3-methylcatechol.
11. The process of claim 10 further comprising formylating, under reaction conditions, 4-tert-butyl-2-methylphenol with formaldehyde; and
forming the 5-tert-butyl-3-methyl-2-hydroxybenzaldehyde.
12. The process of claim 10 further comprising alkylating, under reaction conditions, o-cresol with a member selected from the group consisting of isobutylene and t-butanol to form 4-tert-butyl-2-methylphenol; and
formylating, under reaction conditions, the 4-tert-butyl-2-methylphenol with formaldehyde to form the 5-tert-butyl-3-methyl-2-hydroxybenzaldehyde.
13. The process of claim 1 further comprising:
oxidizing, under reaction conditions, 4-tert-butyl-2-methylphenol; and
forming 5-tert-butyl-3-methylcatechol.
14. The process of claim 13 further comprising:
alkylating, under reaction conditions, o-cresol with a member selected from the group consisting of tert-butanol and isobutylene; and
forming the 4-tert-butyl-2-methylphenol.
15. The process claim 1 further comprising:
hydrolyzing, under reaction conditions, 2-halo-4-tert-butyl-6-methylphenol; and
forming 5-tert-butyl-3-methylcatechol.
16. The process of claim 15 further comprising chlorinating, under reaction conditions, 4-tert-butyl-2-methylphenol; and
forming 2-chloro-4-tert-butyl-6-methylphenol.
17. The process of claim 15 further comprising brominating, under reaction conditions, 4-tert-butyl-2-methylphenol; and
forming 2-bromo-4-tert-butyl-6-methylphenol.
18. The process of claim 15 further comprising alkylating, under reaction conditions, o-cresol with a member selected from the group consisting of isobutylene and t-butanol to form 4-tert-butyl-2-methylphenol; and
chlorinating the 4-tert-butyl-2-methylphenol to form 2-chloro-4-tert-butyl-6-methylphenol.
19. The process of claim 15 further comprising alkylating, under reaction conditions, o-cresol with a member selected from the group consisting of isobutylene and t-butanol to form 4-tert-butyl-2-methylphenol; and
brominating the 4-tert-butyl-2-methylphenol to form 2-bromo-4-tert-butyl-6-methylphenol.