Effective strategy for high-yield furan dicarboxylate production for biobased polyester applications

Minjune Kim, Yaqiong Su, T. Aoshima, A. (Atsushi) Fukuoka, Emiel Hensen (Corresponding author), Kiyotaka Nakajima (Corresponding author)

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

3 Citaties (Scopus)
1 Downloads (Pure)

Uittreksel

A unique strategy for the formation of furan-2,5-dicarboxylic acid (FDCA)-derived esters with methanol and ethylene glycol in concentrated solutions was reported using a six-membered ring acetal of (5-hydroxymethyl)furfural (HMF) with 1,3-propanediol in order to improve the economics for the production of polyethylene 2,5-furandicarboxylate (PEF), a biobased polyester. Aerobic oxidative esterification with methanol and ethylene glycol in the presence of a CeO 2 -supported Au catalyst gave 80-95% yields of methyl furan-2,5-dicarboxylate and bis(2-hydroxyethyl)furan-2,5-dicarboxylate from concentrated HMF-acetal solutions (10-20 wt %). Kinetic studies combined with density functional theory (DFT) calculations were used to identify two key steps for the conversion of the cyclic acetal ring to the corresponding methyl ester: (i) partial hydrolysis of the acetal ring by OH - ions and (ii) subsequent oxidation of the hemiacetal in solution by molecular O 2 on Au nanoparticles. These results represent a significant contribution not only to cutting-edge conversion technology for renewable biomass feedstocks to PEF-based applications but also to opportunities for the efficient conversion of substrates with a reactive formyl group in high yield.

Originele taal-2Engels
Pagina's (van-tot)4277-4285
Aantal pagina's9
TijdschriftACS Catalysis
Volume9
Nummer van het tijdschrift5
DOI's
StatusGepubliceerd - 3 mei 2019

Vingerafdruk

Acetals
Polyesters
Furfural
Ethylene glycol
Ethylene Glycol
Polyethylenes
Esters
Polyethylene
Methanol
Esterification
Catalyst supports
Dicarboxylic Acids
Feedstocks
Density functional theory
Hydrolysis
Biomass
Nanoparticles
Oxidation
Economics
Kinetics

Citeer dit

Kim, Minjune ; Su, Yaqiong ; Aoshima, T. ; Fukuoka, A. (Atsushi) ; Hensen, Emiel ; Nakajima, Kiyotaka. / Effective strategy for high-yield furan dicarboxylate production for biobased polyester applications. In: ACS Catalysis. 2019 ; Vol. 9, Nr. 5. blz. 4277-4285.
@article{609b6fbd0e214bb4923a05cc85f7b511,
title = "Effective strategy for high-yield furan dicarboxylate production for biobased polyester applications",
abstract = "A unique strategy for the formation of furan-2,5-dicarboxylic acid (FDCA)-derived esters with methanol and ethylene glycol in concentrated solutions was reported using a six-membered ring acetal of (5-hydroxymethyl)furfural (HMF) with 1,3-propanediol in order to improve the economics for the production of polyethylene 2,5-furandicarboxylate (PEF), a biobased polyester. Aerobic oxidative esterification with methanol and ethylene glycol in the presence of a CeO 2 -supported Au catalyst gave 80-95{\%} yields of methyl furan-2,5-dicarboxylate and bis(2-hydroxyethyl)furan-2,5-dicarboxylate from concentrated HMF-acetal solutions (10-20 wt {\%}). Kinetic studies combined with density functional theory (DFT) calculations were used to identify two key steps for the conversion of the cyclic acetal ring to the corresponding methyl ester: (i) partial hydrolysis of the acetal ring by OH - ions and (ii) subsequent oxidation of the hemiacetal in solution by molecular O 2 on Au nanoparticles. These results represent a significant contribution not only to cutting-edge conversion technology for renewable biomass feedstocks to PEF-based applications but also to opportunities for the efficient conversion of substrates with a reactive formyl group in high yield.",
keywords = "acetal functionality, biobased polymer, biomass conversion, oxidative esterification, supported Au catalyst",
author = "Minjune Kim and Yaqiong Su and T. Aoshima and Fukuoka, {A. (Atsushi)} and Emiel Hensen and Kiyotaka Nakajima",
year = "2019",
month = "5",
day = "3",
doi = "10.1021/acscatal.9b00450",
language = "English",
volume = "9",
pages = "4277--4285",
journal = "ACS Catalysis",
issn = "2155-5435",
publisher = "American Chemical Society",
number = "5",

}

Effective strategy for high-yield furan dicarboxylate production for biobased polyester applications. / Kim, Minjune; Su, Yaqiong; Aoshima, T.; Fukuoka, A. (Atsushi); Hensen, Emiel (Corresponding author); Nakajima, Kiyotaka (Corresponding author).

In: ACS Catalysis, Vol. 9, Nr. 5, 03.05.2019, blz. 4277-4285.

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

TY - JOUR

T1 - Effective strategy for high-yield furan dicarboxylate production for biobased polyester applications

AU - Kim, Minjune

AU - Su, Yaqiong

AU - Aoshima, T.

AU - Fukuoka, A. (Atsushi)

AU - Hensen, Emiel

AU - Nakajima, Kiyotaka

PY - 2019/5/3

Y1 - 2019/5/3

N2 - A unique strategy for the formation of furan-2,5-dicarboxylic acid (FDCA)-derived esters with methanol and ethylene glycol in concentrated solutions was reported using a six-membered ring acetal of (5-hydroxymethyl)furfural (HMF) with 1,3-propanediol in order to improve the economics for the production of polyethylene 2,5-furandicarboxylate (PEF), a biobased polyester. Aerobic oxidative esterification with methanol and ethylene glycol in the presence of a CeO 2 -supported Au catalyst gave 80-95% yields of methyl furan-2,5-dicarboxylate and bis(2-hydroxyethyl)furan-2,5-dicarboxylate from concentrated HMF-acetal solutions (10-20 wt %). Kinetic studies combined with density functional theory (DFT) calculations were used to identify two key steps for the conversion of the cyclic acetal ring to the corresponding methyl ester: (i) partial hydrolysis of the acetal ring by OH - ions and (ii) subsequent oxidation of the hemiacetal in solution by molecular O 2 on Au nanoparticles. These results represent a significant contribution not only to cutting-edge conversion technology for renewable biomass feedstocks to PEF-based applications but also to opportunities for the efficient conversion of substrates with a reactive formyl group in high yield.

AB - A unique strategy for the formation of furan-2,5-dicarboxylic acid (FDCA)-derived esters with methanol and ethylene glycol in concentrated solutions was reported using a six-membered ring acetal of (5-hydroxymethyl)furfural (HMF) with 1,3-propanediol in order to improve the economics for the production of polyethylene 2,5-furandicarboxylate (PEF), a biobased polyester. Aerobic oxidative esterification with methanol and ethylene glycol in the presence of a CeO 2 -supported Au catalyst gave 80-95% yields of methyl furan-2,5-dicarboxylate and bis(2-hydroxyethyl)furan-2,5-dicarboxylate from concentrated HMF-acetal solutions (10-20 wt %). Kinetic studies combined with density functional theory (DFT) calculations were used to identify two key steps for the conversion of the cyclic acetal ring to the corresponding methyl ester: (i) partial hydrolysis of the acetal ring by OH - ions and (ii) subsequent oxidation of the hemiacetal in solution by molecular O 2 on Au nanoparticles. These results represent a significant contribution not only to cutting-edge conversion technology for renewable biomass feedstocks to PEF-based applications but also to opportunities for the efficient conversion of substrates with a reactive formyl group in high yield.

KW - acetal functionality

KW - biobased polymer

KW - biomass conversion

KW - oxidative esterification

KW - supported Au catalyst

UR - http://www.scopus.com/inward/record.url?scp=85065072352&partnerID=8YFLogxK

U2 - 10.1021/acscatal.9b00450

DO - 10.1021/acscatal.9b00450

M3 - Article

AN - SCOPUS:85065072352

VL - 9

SP - 4277

EP - 4285

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 5

ER -