Scientists Discover Method to Produce FDCA Using Non-food Glucose Derivative
Scientists have discovered a novel method to synthesize
furan-2,5-dicarboxylic acid (FDCA) in a high yield from a glucose
derivative of non-food plant cellulose, paving the way for replacing
petroleum-derived terephthalic acid with biomaterials in plastic bottle
applications.
The chemical industry is under pressure to establish energy-efficient
chemical procedures that do not generate by-products, and using
renewable resources wherever possible. Scientists believe that if
resources from non-food plants can be used without putting a burden on
the environment, it will help sustain existing social systems.
In the study published in Angewandte Chemie International Edition, a Japan-Netherland research team led by Associate Professor Kiyotaka Nakajima at Hokkaido University and Professor Emiel J.M. Hensen at Eindhove University of Technology succeeded in suppressing the side reactions and producing FDCA with high yields from concentrated HMF solutions (10~20 wt%) without by-products formation. Specifically, they first acetalized HMF with 1,3-propanediol to protect by-product-inducing formyl groups and then oxidized HMF-acetal with a supported Au catalyst.
Conventional methods produce by-products making large-scale FDCA production difficult, while this new method yields FDCA efficiently without by-products formation.
About 80% of 1,3-propanediol used to protect formyl groups can be reused for the subsequent reactions. In addition, drastic improvement in the substrate concentration reduces the amount of solvents used in the production process.
Kiyotaka Nakajima says “It is significant that our method can reduce the total energy consumption required for complex work-up processes to isolate the reaction product.”
“These results represent a significant advance over the current state of the art, overcoming an inherent limitation of the oxidation of HMF to an important monomer for biopolymer production. Controlling the reactivity of formyl group could open the door for the production of commodity chemicals from sugar-based biomaterials,” says Kiyotaka Nakajima. This study was conducted jointly with Mitsubishi Chemical Corporation.
Source: Hokkaido University
Decreasing Burden on the Environment with Renewable Resources
The chemical industry is under pressure to establish energy-efficient
chemical procedures that do not generate by-products, and using
renewable resources wherever possible. Scientists believe that if
resources from non-food plants can be used without putting a burden on
the environment, it will help sustain existing social systems.
It has been reported that various useful polymers can be synthesized
from 5-(hydroxymethyl)furfural (HMF), the biomaterial used in this
study. A high yield of FDCA can be obtained when HMF is oxidized in a
diluted solution under 2 weight percentage (wt%) with various supported
metal catalysts.
However, a major stumbling block to industrial application lies with the
use of a concentrated solution of 10-20 wt%, which is essential for
efficient and scalable production of FDCA in the chemical industry. When
HMF was simply oxidized in a concentrated solution (10 wt%), the FDCA
yield was only around 30%, and a large amount of solid by-products was
formed simultaneously. This is due to complex side reactions induced
from HMF itself.
Producing FDCA with High Yields
In the study published in Angewandte Chemie International Edition, a Japan-Netherland research team led by Associate Professor Kiyotaka Nakajima at Hokkaido University and Professor Emiel J.M. Hensen at Eindhove University of Technology succeeded in suppressing the side reactions and producing FDCA with high yields from concentrated HMF solutions (10~20 wt%) without by-products formation. Specifically, they first acetalized HMF with 1,3-propanediol to protect by-product-inducing formyl groups and then oxidized HMF-acetal with a supported Au catalyst.
Conventional methods produce by-products making large-scale FDCA production difficult, while this new method yields FDCA efficiently without by-products formation.
Producing Chemicals from Sugar-based Biomaterials
About 80% of 1,3-propanediol used to protect formyl groups can be reused for the subsequent reactions. In addition, drastic improvement in the substrate concentration reduces the amount of solvents used in the production process.
Kiyotaka Nakajima says “It is significant that our method can reduce the total energy consumption required for complex work-up processes to isolate the reaction product.”
“These results represent a significant advance over the current state of the art, overcoming an inherent limitation of the oxidation of HMF to an important monomer for biopolymer production. Controlling the reactivity of formyl group could open the door for the production of commodity chemicals from sugar-based biomaterials,” says Kiyotaka Nakajima. This study was conducted jointly with Mitsubishi Chemical Corporation.
Source: Hokkaido University
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