Biobased n-Butanol Prepared from Poly-3-hydroxybutyrate: Optimization of the Reduction of n-Butyl Crotonate to n-Butanol

Schweitzer, Dirk; Mullen, Charles A.; Boateng, Akwasi A.; Snell, Kristi D.

doi:10.1021/op500156b

Cited by 11 publications

(10 citation statements)

References 35 publications

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“…The world consumption of butadiene reached 10 million metric tons in 2012 (Biddy et al, 2016). R3HBA can be esterified with butanol or ethanol or converted to ethers by reaction with alcohols using the catalytic Williamson ether synthesis (Fuhrmann and Talbiersky, 2005) or dehydrated to crotonic acid, which upon hydrogenation yields butyric acid and n-butanol (Schweitzer et al, 2015).…”

Section: Potential Uses Of Polyhydroxyalkanoates and Its Monomersmentioning

confidence: 99%

Beyond Intracellular Accumulation of Polyhydroxyalkanoates: Chiral Hydroxyalkanoic Acids and Polymer Secretion

Yáñez

Conejeros

Vergara-Fernández

et al. 2020

Front. Bioeng. Biotechnol.

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Polyhydroxyalkanoates (PHAs) are ubiquitous prokaryotic storage compounds of carbon and energy, acting as sinks for reducing power during periods of surplus of carbon source relative to other nutrients. With close to 150 different hydroxyalkanoate monomers identified, the structure and properties of these polyesters can be adjusted to serve applications ranging from food packaging to biomedical uses. Despite its versatility and the intensive research in the area over the last three decades, the market share of PHAs is still low. While considerable rich literature has accumulated concerning biochemical, physiological, and genetic aspects of PHAs intracellular accumulation, the costs of substrates and processing costs, including the extraction of the polymer accumulated in intracellular granules, still hampers a more widespread use of this family of polymers. This review presents a comprehensive survey and critical analysis of the process engineering and metabolic engineering strategies reported in literature aimed at the production of chiral (R)-hydroxycarboxylic acids (RHAs), either from the accumulated polymer or by bypassing the accumulation of PHAs using metabolically engineered bacteria, and the strategies developed to recover the accumulated polymer without using conventional downstream separations processes. Each of these topics, that have received less attention compared to PHAs accumulation, could potentially improve the economy of PHAs production and use. (R)-hydroxycarboxylic acids can be used as chiral precursors, thanks to its easily modifiable functional groups, and can be either produced de-novo or be obtained from recycled PHA products. On the other hand, efficient mechanisms of PHAs release from bacterial cells, including controlled cell lysis and PHA excretion, could reduce downstream costs and simplify the polymer recovery process.

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Section: Potential Uses Of Polyhydroxyalkanoates and Its Monomersmentioning

confidence: 99%

Beyond Intracellular Accumulation of Polyhydroxyalkanoates: Chiral Hydroxyalkanoic Acids and Polymer Secretion

Yáñez

Conejeros

Vergara-Fernández

et al. 2020

Front. Bioeng. Biotechnol.

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“…A conversion of PHB to chemicals has been proposed by Metabolix, where PHB is converted to CA via pyrolysis at 200°C using Ca(OH) 2 as a catalyst. The CA produced could be further converted into drop‐in chemicals such as n ‐butanol, maleic anhydride, and propylene . Converting PHB to chemicals can also be applied at the end of life of PHB products.…”

Section: Introductionmentioning

confidence: 99%

Conversion of polyhydroxybutyrate (PHB) to methyl crotonate for the production of biobased monomers

Spekreijse

Nôtre

Sanders

et al. 2015

J of Applied Polymer Sci

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Within the concept of the replacement of fossil with biobased resources, bacterial polyhydroxybutyrate (PHB) can be obtained from volatile fatty acids (VFAs) from agro‐food waste streams and used as an intermediate toward attractive chemicals. Here we address a crucial step in this process, the conversion of PHB to methyl crotonate (MC), which can be converted via cross‐metathesis with ethylene to methyl acrylate and propylene, two important monomers for the plastics industry. The conversion of PHB to MC proceeds via a thermolysis of PHB to crotonic acid (CA), followed by an esterification to MC. At pressures below 18 bar, the thermolysis of PHB to CA is the rate‐determining step, where above 18 bar, the esterification of CA to MC becomes rate limiting. At 200°C and 18 bar, a full conversion and 60% selectivity to MC is obtained. This conversion circumvents processing and application issues of PHB as a polymer and allows PHB to be used as an intermediate to produce biobased chemicals. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 42462.

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“…The manufacturing of PHB as a value-added co-product in plants, particularly high-biomass-yielding crops such as sugarcane, switchgrass, and maize, has the potential to improve the economics of their use for bio-plastic fabrication [ 7 , 8 ]. PHB has been successfully engineered in a number of plant species [ 9 ] and has potential applications not only as a bio-plastic but also for the manufacture of chemicals and improved animal feed [ 9 – 13 ].…”

Section: Introductionmentioning

confidence: 99%

Localization of polyhydroxybutyrate in sugarcane using Fourier-transform infrared microspectroscopy and multivariate imaging

Lupoi

Smith-Moritz

Singh

et al. 2015

Biotechnol Biofuels

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BackgroundSlow-degrading, fossil fuel-derived plastics can have deleterious effects on the environment, especially marine ecosystems. The production of bio-based, biodegradable plastics from or in plants can assist in supplanting those manufactured using fossil fuels. Polyhydroxybutyrate (PHB) is one such biodegradable polyester that has been evaluated as a possible candidate for relinquishing the use of environmentally harmful plastics.ResultsPHB, possessing similar properties to polyesters produced from non-renewable sources, has been previously engineered in sugarcane, thereby creating a high-value co-product in addition to the high biomass yield. This manuscript illustrates the coupling of a Fourier-transform infrared microspectrometer, equipped with a focal plane array (FPA) detector, with multivariate imaging to successfully identify and localize PHB aggregates. Principal component analysis imaging facilitated the mining of the abundant quantity of spectral data acquired using the FPA for distinct PHB vibrational modes. PHB was measured in the chloroplasts of mesophyll and bundle sheath cells, acquiescent with previously evaluated plant samples.ConclusionThis study demonstrates the power of IR microspectroscopy to rapidly image plant sections to provide a snapshot of the chemical composition of the cell. While PHB was localized in sugarcane, this method is readily transferable to other value-added co-products in different plants.

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Biobased n-Butanol Prepared from Poly-3-hydroxybutyrate: Optimization of the Reduction of n-Butyl Crotonate to n-Butanol

Cited by 11 publications

References 35 publications

Beyond Intracellular Accumulation of Polyhydroxyalkanoates: Chiral Hydroxyalkanoic Acids and Polymer Secretion

Beyond Intracellular Accumulation of Polyhydroxyalkanoates: Chiral Hydroxyalkanoic Acids and Polymer Secretion

Conversion of polyhydroxybutyrate (PHB) to methyl crotonate for the production of biobased monomers

Localization of polyhydroxybutyrate in sugarcane using Fourier-transform infrared microspectroscopy and multivariate imaging

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