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Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid. / Beerthuis, Rolf; Granollers, Marta; Brown, D. Robert et al.
In: RSC Advances, Vol. 5, No. 6, 01.05.2015, p. 4103-4108.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Beerthuis, R, Granollers, M, Brown, DR, Salavagione, HJ, Rothenberg, G & Shiju, NR 2015, 'Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid', RSC Advances, vol. 5, no. 6, pp. 4103-4108. https://doi.org/10.1039/C4RA12695E

APA

Beerthuis, R., Granollers, M., Brown, D. R., Salavagione, H. J., Rothenberg, G., & Shiju, N. R. (2015). Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid. RSC Advances, 5(6), 4103-4108. https://doi.org/10.1039/C4RA12695E

Vancouver

Beerthuis R, Granollers M, Brown DR, Salavagione HJ, Rothenberg G, Shiju NR. Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid. RSC Advances. 2015 May 1;5(6):4103-4108. doi: 10.1039/C4RA12695E

Author

Beerthuis, Rolf ; Granollers, Marta ; Brown, D. Robert et al. / Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid. In: RSC Advances. 2015 ; Vol. 5, No. 6. pp. 4103-4108.

Bibtex

@article{5e08ebc52e5d456aba2bfc8eb55c8271,
title = "Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid",
abstract = "We present an alternative synthetic route to acrylic acid, starting from the platform chemical lactic acid and using heterogeneous catalysis. To improve selectivity, we designed an indirect dehydration reaction that proceeds via acetoxylation of lactic acid to 2-acetoxypropionic acid. This intermediate can then be pyrolized to acrylic acid. Acetic acid is used both as a reagent and a solvent in the first step, and may be recovered in the subsequent pyrolysis step. We tested a range of solid acid catalysts for the acetoxylation step (Y zeolites, sulfated zirconia, ion-exchange resins, sulfonated graphene, and various sulfonated silica gels and mixed oxides). Recycling studies were carried out for the most active catalysts. To enable quantitative analysis using gas chromatography we also developed a reliable silylation derivatization method, which is also reported. These results open opportunities for improving the biorenewable production of acrylic acid.",
author = "Rolf Beerthuis and Marta Granollers and Brown, {D. Robert} and Salavagione, {Horacio J.} and Gadi Rothenberg and Shiju, {N. Raveendran}",
year = "2015",
month = may,
day = "1",
doi = "10.1039/C4RA12695E",
language = "English",
volume = "5",
pages = "4103--4108",
journal = "RSC Advances",
issn = "2046-2069",
publisher = "Royal Society of Chemistry",
number = "6",

}

RIS

TY - JOUR

T1 - Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid

AU - Beerthuis, Rolf

AU - Granollers, Marta

AU - Brown, D. Robert

AU - Salavagione, Horacio J.

AU - Rothenberg, Gadi

AU - Shiju, N. Raveendran

PY - 2015/5/1

Y1 - 2015/5/1

N2 - We present an alternative synthetic route to acrylic acid, starting from the platform chemical lactic acid and using heterogeneous catalysis. To improve selectivity, we designed an indirect dehydration reaction that proceeds via acetoxylation of lactic acid to 2-acetoxypropionic acid. This intermediate can then be pyrolized to acrylic acid. Acetic acid is used both as a reagent and a solvent in the first step, and may be recovered in the subsequent pyrolysis step. We tested a range of solid acid catalysts for the acetoxylation step (Y zeolites, sulfated zirconia, ion-exchange resins, sulfonated graphene, and various sulfonated silica gels and mixed oxides). Recycling studies were carried out for the most active catalysts. To enable quantitative analysis using gas chromatography we also developed a reliable silylation derivatization method, which is also reported. These results open opportunities for improving the biorenewable production of acrylic acid.

AB - We present an alternative synthetic route to acrylic acid, starting from the platform chemical lactic acid and using heterogeneous catalysis. To improve selectivity, we designed an indirect dehydration reaction that proceeds via acetoxylation of lactic acid to 2-acetoxypropionic acid. This intermediate can then be pyrolized to acrylic acid. Acetic acid is used both as a reagent and a solvent in the first step, and may be recovered in the subsequent pyrolysis step. We tested a range of solid acid catalysts for the acetoxylation step (Y zeolites, sulfated zirconia, ion-exchange resins, sulfonated graphene, and various sulfonated silica gels and mixed oxides). Recycling studies were carried out for the most active catalysts. To enable quantitative analysis using gas chromatography we also developed a reliable silylation derivatization method, which is also reported. These results open opportunities for improving the biorenewable production of acrylic acid.

U2 - 10.1039/C4RA12695E

DO - 10.1039/C4RA12695E

M3 - Journal article

VL - 5

SP - 4103

EP - 4108

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 6

ER -