Successful selective production of vanillic acid from depolymerized sulfite lignin and its application to poly(ethylene vanillate) synthesis

Yudai Higuchi; Hiroya Ishimaru; Takuya Yoshikawa; Takao Masuda; Chiho Sakamoto; Naofumi Kamimura; Eiji Masai; Daisuke Takeuchi; Tomonori Sonoki

doi:10.1016/j.biortech.2023.129450

Successful selective production of vanillic acid from depolymerized sulfite lignin and its application to poly(ethylene vanillate) synthesis

Bioresour Technol. 2023 Oct:385:129450. doi: 10.1016/j.biortech.2023.129450. Epub 2023 Jul 3.

Authors

Yudai Higuchi¹, Hiroya Ishimaru², Takuya Yoshikawa³, Takao Masuda², Chiho Sakamoto¹, Naofumi Kamimura⁴, Eiji Masai⁴, Daisuke Takeuchi⁵, Tomonori Sonoki⁶

Affiliations

¹ Faculty of Agriculture and Life Science, Hirosaki University, Hirosaki, Aomori 036-8561, Japan.
² Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.
³ Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan; Obihiro University of Agriculture and Veterinary Medicine, Obihiro, Hokkaido 080-8555, Japan.
⁴ Department of Materials Science and Bioengineering, Nagaoka University of Technology, Nagaoka, Niigata 940-2188, Japan.
⁵ Graduate School of Science and Technology, Hirosaki University, Hirosaki, Aomori 036-8561, Japan.
⁶ Faculty of Agriculture and Life Science, Hirosaki University, Hirosaki, Aomori 036-8561, Japan. Electronic address: sonoki@hirosaki-u.ac.jp.

PMID: 37406831
DOI: 10.1016/j.biortech.2023.129450

Abstract

Towards lignin upgrading, vanillic acid (VA), a lignin-derived guaiacyl compound, was produced from sulfite lignin for successfully synthesizing poly(ethylene vanillate), an aromatic polymer. The engineered Sphingobium sp. SYK-6-based strain in which the genes responsible for VA/3-O-methyl gallic acid O-demethylase and syringic acid O-demethylase were disrupted was able to produce vanillic acid (VA) from the mixture consisting of acetovanillone, vanillin, VA, and other low-molecular-weight aromatics obtained by Cu(OH)₂-catalyzed alkaline depolymerization of sulfite lignin and membrane fractionation. From the bio-based VA, methyl-4-(2-hydroxyethoxy)-3-methoxybenzoate was synthesized via methylesterification, hydroxyethylation, and distillation, and then it was subjected to polymerization catalyzed by titanium tetraisopropoxide. The molecular weight of the obtained poly(ethylene vanillate) was evaluated to be M_w = 13,000 (M_w/M_n = 1.99) and its melting point was 261 °C. The present work proved that poly(ethylene vanillate) is able to be synthesized using VA produced from lignin for the first time.

Keywords: Alkaline depolymerization; Lignin upgrading; Poly(ethylene vanillate); Sphingobium sp. SYK-6; Vanillic acid.

MeSH terms

Ethylenes
Lignin*
Oxidoreductases, O-Demethylating / genetics
Polyethylene
Vanillic Acid*

Substances

Lignin
Vanillic Acid
Polyethylene
Oxidoreductases, O-Demethylating
Ethylenes