Carbonylation of Ethylene Oxide to β-Propiolactone: A Facile Route to Poly(3-hydroxypropionate) and Acrylic Acid

Dunn, Erin W.; Lamb, Jessica R.; LaPointe, Anne M.; Coates, Geoffrey W.

doi:10.1021/acscatal.6b02773

Cited by 47 publications

(50 citation statements)

References 52 publications

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“…Carbon monoxide is known to be an intermediate of CO 2 reduction on copper electrodes in aqueous electrolytes [21][22] as well as in acetonitrile electrolyte containing small amounts of water. [23] However, the absence of the band at 1800 cm À 1 (corresponding with propylene carbonate) when CO 2 is exchanged for CO, discards CO as the electroactive species in the mechanism of propylene carbonate formation. [23] However, the absence of the band at 1800 cm À 1 (corresponding with propylene carbonate) when CO 2 is exchanged for CO, discards CO as the electroactive species in the mechanism of propylene carbonate formation.…”

Section: Proposed Mechanismmentioning

confidence: 99%

“…[17] It is also known that the catalytic reaction between CO and propylene oxide can yield propiolactone under certain conditions. [23] However, the absence of the band at 1800 cm À 1 (corresponding with propylene carbonate) when CO 2 is exchanged for CO, discards CO as the electroactive species in the mechanism of propylene carbonate formation. Previous studies of CO 2 reduction in non-aqueous solvents showed that the main products formed at high overpotentials are bi(carbonates).…”

Section: Proposed Mechanismmentioning

confidence: 99%

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Mechanistic Study of the Electrosynthesis of Propylene Carbonate from Propylene Oxide and CO₂ on Copper Electrodes

2019

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Efficient and selective electrosynthesis of propylene carbonate can be performed by the reaction of carbon dioxide with propylene oxide at copper electrodes. In this paper, we investigate this electrochemical reaction by using cyclic voltammetry, Fourier transform infrared spectroscopy and highperformance liquid chromatography in order to unravel details of the catalytic mechanism of the reaction. The combination of the results obtained by these different techniques allows the exclusion of different reduced forms of CO 2 , such as CO and (bi) carbonates, as possible carboxylation agents. Moreover, the results also indicate that electrochemical activation of the propylene oxide by ring opening is not the initial step for this reaction, as no product was detected when a current was not applied in presence of "activated propylene oxide" and CO 2 . Our results show that the reaction is initiated by the activation of CO 2 to CO 2 * À , which then attacks the epoxide to form the cyclic carbonate. This work also gives evidence for the noncatalytic nature of the synthesis of the cyclic carbonate because its formation also occurs on other metals such as gold and platinum in the same range of applied currents. This result clearly indicates the potential of in situ electrochemical techniques in the mechanistic investigation of electrosynthesis reactions.

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Section: Proposed Mechanismmentioning

confidence: 99%

Section: Proposed Mechanismmentioning

confidence: 99%

Mechanistic Study of the Electrosynthesis of Propylene Carbonate from Propylene Oxide and CO₂ on Copper Electrodes

2019

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“…However, poly(3HP) was not commercially feasible to produce in large quantities because β-propiolactone as a substrate has carcinogenic properties ( Dunn, 2012 ; Dunn et al, 2016 ). 3-HP, which has low crystallinity, is an ideal precursor that forms a constituent for several copolymers like poly(3-hydroxybutyrate-co-3-hydroxypropionate) [poly(3HB-co-3HP)] or poly(3-hydroxypropionate-co-4-hydroxybutyrate) [Poly(3HP-co-4HB)] ( Zhou et al, 2011 ; Wang et al, 2013 ).…”

Section: Introductionmentioning

confidence: 99%

Poly(3-hydroxypropionate): Biosynthesis Pathways and Malonyl-CoA Biosensor Material Properties

Aduhene

Cui

Yang

et al. 2021

Front. Bioeng. Biotechnol.

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Many single-use non-degradable plastics are a threat to life today, and several polyhydroxyalkanoates (PHAs) biopolymers have been developed in the bioplastic industry to place petrochemical-based plastics. One of such is the novel biomaterial poly(3-hydroxypropionate) [poly(3HP)] because of its biocompatibility, biodegradability, and high yield synthesis using engineered strains. To date, many bio-polymer-based functional composites have been developed to increase the value of raw microbial-biopolymers obtained from cheap sources. This review article broadly covers poly(3HP), a comprehensive summary of critical biosynthetic production pathways comparing the yields and titers achieved in different Microbial cell Factories. This article also provides extensive knowledge and highlights recent progress on biosensors’ use to optimize poly(3HP) production, some bacteria host adopted for production, chemical and physical properties, life cycle assessment for poly(3HP) production using corn oil as carbon source, and some essential medical applications of poly(3HP).

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“…[ 44 ] In 2016, Coates and co‐workers investigated various catalysts for the Novomer route. [ 45 ] Ethylene oxide and carbon monoxide can be derived from fossil resources or respectively from bioethanol and CO 2 or gasified biomass, making it virtually a biobased route. Similarly, poly(3‐hydroxybutyrate) (PHB), biosynthesized by various microorganisms from wastewater, can be pyrolyzed to crotonic acid (CrA) (see Section 2.5.4) for more details).…”

Section: Production Of Biobased Acrylates and Analogsmentioning

confidence: 99%

Production and Polymerization of Biobased Acrylates and Analogs

Fouilloux

Thomas

2021

Macromol. Rapid Commun.

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To prepare biobased polymers, particular attention must be paid to the obtention of the monomers from which they are derived. (Meth)acrylates and their analogs constitute such a class of monomers that have been extensively studied due to the wide range of polymers accessible from them. This review therefore aims to highlight the progresses made in the production and polymerization of (meth)acrylates and their analogs. Acrylic acid production from biomass is close to commercialization, as three different high‐potential intermediates are identified: glycerol, lactic acid, and 3‐hydroxypropionic acid. Biobased methacrylic acid is less common, but several promising options are available, such as the decarboxylation of itaconic acid or the dehydration of 2‐hydroxyisobutyric acid. Itaconic acid is also a vinylic monomer of great interest, and polymers derived from it have already found commercial applications. Methylene butyrolactones are promising monomers, obtained from bioresources via three different intermediates: levulinic, succinic, or itaconic acid. Although expensive, methylene butyrolactones have a strong potential for the production of high‐performance polymers. Finally, β‐substituted acrylic monomers, such as cinnamic, fumaric, muconic, or crotonic acid, are also examined, as they provide an original access to biobased materials from various renewable raw materials, such as protein waste, lignin, or wastewater.

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Carbonylation of Ethylene Oxide to β-Propiolactone: A Facile Route to Poly(3-hydroxypropionate) and Acrylic Acid

Cited by 47 publications

References 52 publications

Mechanistic Study of the Electrosynthesis of Propylene Carbonate from Propylene Oxide and CO₂ on Copper Electrodes

Mechanistic Study of the Electrosynthesis of Propylene Carbonate from Propylene Oxide and CO₂ on Copper Electrodes

Poly(3-hydroxypropionate): Biosynthesis Pathways and Malonyl-CoA Biosensor Material Properties

Production and Polymerization of Biobased Acrylates and Analogs

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Carbonylation of Ethylene Oxide to β-Propiolactone: A Facile Route to Poly(3-hydroxypropionate) and Acrylic Acid

Cited by 47 publications

References 52 publications

Mechanistic Study of the Electrosynthesis of Propylene Carbonate from Propylene Oxide and CO2 on Copper Electrodes

Mechanistic Study of the Electrosynthesis of Propylene Carbonate from Propylene Oxide and CO2 on Copper Electrodes

Poly(3-hydroxypropionate): Biosynthesis Pathways and Malonyl-CoA Biosensor Material Properties

Production and Polymerization of Biobased Acrylates and Analogs

Contact Info

Product

Resources

About

Mechanistic Study of the Electrosynthesis of Propylene Carbonate from Propylene Oxide and CO₂ on Copper Electrodes

Mechanistic Study of the Electrosynthesis of Propylene Carbonate from Propylene Oxide and CO₂ on Copper Electrodes