Production of Bioacrylic Acid

Katryniok, Benjamin; Bonnotte, Thomas; Dumeignil, Franck; Paul, Sébastien

doi:10.1002/9783527698202.ch9

Cited by 5 publications

(4 citation statements)

References 85 publications

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“…LA is generally dehydrated to AA using a heterogeneously catalyzed process . Despite the attractiveness of a biomass derived AA, no process for the transformation of GLY to AA either by the direct or the indirect pathway has been commercialized so far …”

Section: Introductionmentioning

confidence: 99%

“…9 Despite the attractiveness of a biomass derived AA, no process for the transformation of GLY to AA either by the direct or the indirect pathway has been commercialized so far. 8 In this work, we report the transformation of 1,3-propandiol (1,3-P) to acrylate in an electroreformer. Low temperature electrochemical processes can offer attractive solutions, as they are energy efficient, flexible, and do not require harsh conditions or multiple reagents.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Bioacrylic acid (Bio-AA) can be obtained through both chemical or biochemical routes starting from renewable compounds such as glycerol (GLY), lactic acid (LA) or C6 sugars, and ethanol. 8 GLY can be oxidized in one step to AA or using an indirect pathway, where acrolein, 3-hydroxypropionaldehyde, or acrylonitrile can be, respectively, used as intermediates. 8 LA is generally dehydrated to AA using a heterogeneously catalyzed process.…”

Section: ■ Introductionmentioning

confidence: 99%

“…8 GLY can be oxidized in one step to AA or using an indirect pathway, where acrolein, 3-hydroxypropionaldehyde, or acrylonitrile can be, respectively, used as intermediates. 8 LA is generally dehydrated to AA using a heterogeneously catalyzed process. 9 Despite the attractiveness of a biomass derived AA, no process for the transformation of GLY to AA either by the direct or the indirect pathway has been commercialized so far.…”

Section: ■ Introductionmentioning

confidence: 99%

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Electrochemical Coproduction of Acrylate and Hydrogen from 1,3-Propandiol

Mahmoudian

Bellini

Pagliaro

et al. 2017

ACS Sustainable Chem. Eng.

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The coproduction of acrylate and hydrogen from 1,3-propandiol is achieved by electrochemical reforming using a nanoparticle Pd on mixed Vulcan XC-72 carbon and ceria electrocatalyst (Pd/C-CeO 2 ). Electrolysis cell parameters (potential, temperature, and flow conditions) are tuned to favor the formation of acrylate with respect to the other oxidation products (3-hydroxypropanoate and malonate). Using high cell temperature combined with a low cell voltage favors the formation of acrylate, the selectivity for which is further enhanced by flowing the 1,3-propandiol solution in single-pass mode rather than recycling through the electrolyzer. Hence, at a cell temperature of 80°C and at a fixed cell potential of 400 mV using a one pass continuous flow of 1,3-propandiol, 77% of selectivity for acrylate is obtained.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Electrochemical Coproduction of Acrylate and Hydrogen from 1,3-Propandiol

Mahmoudian

Bellini

Pagliaro

et al. 2017

ACS Sustainable Chem. Eng.

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Dynamic Trapping as a Selective Route to Renewable Phthalide from Biomass‐Derived Furfuryl Alcohol

et al. 2020

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A novel route for the production of the versatile chemical building block phthalide from biorenewable furfuryl alcohol and acrylate esters is presented. Two challenges that limit sustainable aromatics production via Diels–Alder (DA) aromatisation—an unfavourable equilibrium position and undesired regioselectivity when using asymmetric addends—were addressed using a dynamic kinetic trapping strategy. Activated acrylates were used to speed up the forward and reverse DA reactions, allowing for one of the four DA adducts to undergo a selective intramolecular lactonisation reaction in the presence of a weak base. The adduct is removed from the equilibrium pool, pulling the system completely to the product with a fixed, desired regiochemistry. A single 1,2‐regioisomeric lactone product was formed in up to 86 % yield and the acrylate activating agent liberated for reuse. The lactone was aromatised to give phthalide in almost quantitative yield in the presence of Ac2O and a catalytic amount of strong acid, or in 79 % using only catalytic acid.

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Dynamic Trapping as a Selective Route to Renewable Phthalide from Biomass‐Derived Furfuryl Alcohol

et al. 2020

View full text Add to dashboard Cite

A novel route for the production of the versatile chemical building block phthalide from biorenewable furfuryl alcohol and acrylate esters is presented. Two challenges that limit sustainable aromatics production via Diels-Alder (DA) aromatisation-an unfavourable equilibrium position and undesired regioselectivity when using asymmetric addendswere addressed using a dynamic kinetic trapping strategy. Activated acrylates were used to speed up the forward and reverse DA reactions, allowing for one of the four DA adducts to undergo a selective intramolecular lactonisation reaction in the presence of a weak base. The adduct is removed from the equilibrium pool, pulling the system completely to the product with a fixed, desired regiochemistry. A single 1,2-regioisomeric lactone product was formed in up to 86 % yield and the acrylate activating agent liberated for reuse. The lactone was aromatised to give phthalide in almost quantitative yield in the presence of Ac 2 O and a catalytic amount of strong acid, or in 79 % using only catalytic acid.

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Production of Bioacrylic Acid

Cited by 5 publications

References 85 publications

Electrochemical Coproduction of Acrylate and Hydrogen from 1,3-Propandiol

Electrochemical Coproduction of Acrylate and Hydrogen from 1,3-Propandiol

Dynamic Trapping as a Selective Route to Renewable Phthalide from Biomass‐Derived Furfuryl Alcohol

Dynamic Trapping as a Selective Route to Renewable Phthalide from Biomass‐Derived Furfuryl Alcohol

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