Bio-based acrylic acid from sugar <i>via</i> propylene glycol and allyl alcohol

Pramod, Chodimella Venkata; Fauziah, R.; Seshan, K.; Lange, Jean‐Paul

doi:10.1039/c7cy01416c

Cited by 34 publications

(33 citation statements)

References 52 publications

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“…Another key C 3 olefin compound is prop-2-en-1-ol (allyl alcohol, 3), which is involved in numerous organic synthesis such as preparation of polymer crosslinking agents, resin, coatings and serves as feedstock for various value-added chemical intermediates for the manufacturing of high value added 2,3-epoxy-1propanol (glycidol, 4), 1-chloro-2,3-epoxypropane (epichlorohydrin, 5), butane-1,4-diol (6), prop-2-enal (7) and prop-2-enoic acid (acrylic acid, 8) to name a few. [55][56][57][58][59] Allyl alcohol 3 can be obtained through the DODH of GL and the primary and patent literature have witnessed an increase in related process technologies. Currently, the global production of olefin 3 mostly relies on fossil resources with an estimated market size of 0.1 Mt y À 1 and prices ranging from 2.2-3.2 US$ per kg.…”

Section: Olefins As Privileged Targetsmentioning

confidence: 99%

Perspectives for the Upgrading of Bio‐Based Vicinal Diols within the Developing European Bioeconomy

Muzyka

Monbaliu

2022

ChemSusChem

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The previous decade has witnessed a drastic increase of European incentives aimed at pushing forward the transition from an exclusively petro‐based economy toward a strong and homogeneous bio‐based economy. Since 2012, numerous programs have been developed to stimulate and promote research and innovation relying on sustainable and renewable resources. Terrestrial biomass is a virtually infinite reservoir of biomacromolecules, the biorefining of which provides platform molecules of low complexity yet with tremendous industrial potential. Among such bio‐based platform molecules, polyols and, more specifically, molecules featuring vicinal diols have gained tremendous interest and have stimulated an increasing research effort from the chemistry and chemical engineering communities. This Review revolves around the most promising process conditions and technologies reported since 2012 that specifically target bio‐based vicinal diols and promote their transformation into value‐added molecules of wide industrial interest, such as olefins, epoxides, cyclic carbonates, and ketals.

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Section: Olefins As Privileged Targetsmentioning

confidence: 99%

Perspectives for the Upgrading of Bio‐Based Vicinal Diols within the Developing European Bioeconomy

Muzyka

Monbaliu

2022

ChemSusChem

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“…Acrylic acid and acrylates are valuable monomers for commercial polymers in absorbents, coatings, paints, and adhesives with a market demand of eight megatons in 2017 at an annual growth rate of 4%. 20,21 Currently, acrylic acid is produced via propylene oxidation as a downstream product of the petroleum industry. Lactic acid has been considered as a promising renewable feedstock to acrylic acid and desirable selectivity around 60 -70 C % to acrylic acid has been achieved in gas phase dehydration over solid acid catalysts such as alkali-modified zeolites, hydroxyapatites, and phosphates.…”

Section: ____________________________________________________________________________mentioning

confidence: 99%

“…A 5 ns diffusion simulation with 1 fs time step was performed and the mean-square displacement (MSD) was calculated from the diffusion paths of the water molecules (Figure S11). Using Equation (20) in the mean text, the self-diffusion coefficient ( ) was extracted from the MSD. The water diffusion simulation was repeated with four independent initial configurations and the calculated self-diffusion coefficients were consistent with literature values in Table S2, validating the method and chose of framework.…”

Section: Supporting Information Page S5mentioning

confidence: 99%

On the Spatial Design of Co-Fed Amines for Selective Dehydration of Methyl Lactate to Acrylates

et al. 2021

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Co-feeding an inert and site-selective chemical titrant provides desirable selectivity tuning when titrant adsorption is favored over side reaction pathways on a solid acid catalyst. Here, a selectivity enhancement from 61 to 84 C % was demonstrated for methyl lactate dehydration to methyl acrylate and acrylic acid over a NaY zeolite catalyst using amines as the co-fed titrants to suppress side reactions on in situ-generated Brønsted acid sites (BASs). The effectiveness of BAS titration was evaluated by considering both the basicity and steric properties of the titrant molecule with the goal to maximize the selectivity enhancement. The presence of electron-donating alkyl functional groups not only enhances amine basicity but also introduces additional steric constraints to the molecule with respect to the pore dimensions of the NaY zeolite. While higher basicity of titrant amines favors stronger adsorption on BASs, steric limitations hinder site binding through contributions from internal diffusion limitations and local steric repulsion between the titrant and the zeolite wall around the BAS. Titrant bases with proton affinities above ∼1040 kJ/mol and sizes below 85% of the NaY supercage window or pore diameter are predicted to afford dehydration selectivities above 90 C % to acrylate products.

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“…[71] Innovative routes to produce bio-based acrylic acid have been developed; one promising approach is through hydrogenolysis of carbohydrates to produce propylene glycol, which is further converted to allyl alcohol and then acrylic acid. [72][73][74] Glycerol can be produced readily via transesterification of triglycerides in vegetable oils. It is worth noting that glycerol production has increased significantly with the development of the biodiesel industry.…”

Section: Principle 4: Use Renewable Feedstockmentioning

confidence: 99%

Sustainable polymer reaction engineering: Are we there yet?

et al. 2020

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Polymers are a class of materials that provide unparalleled benefits to humanity, fulfilling countless needs in an exceedingly broad range of applications. Because of their ubiquity and current ways of producing them, polymers also pose significant challenges to the environment. Inspired by a previous publication on sustainable polymer reaction engineering, an update is provided on the latest trends in the use of renewable starting materials for polymers, efforts in process intensification and water-based polymerization, as well as approaches to dealing with the end of the polymers' application life. We seek to answer the question about how far along we are regarding the achievement of completely sustainable polymer processes.

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Bio-based acrylic acid from sugar via propylene glycol and allyl alcohol

Abstract: Propylene glycol is converted to acrylic acid via dehydration to allyl alcohol. A process flow scheme is proposed, based on distillation resistance.

Cited by 34 publications

References 52 publications

Perspectives for the Upgrading of Bio‐Based Vicinal Diols within the Developing European Bioeconomy

Perspectives for the Upgrading of Bio‐Based Vicinal Diols within the Developing European Bioeconomy

On the Spatial Design of Co-Fed Amines for Selective Dehydration of Methyl Lactate to Acrylates

Sustainable polymer reaction engineering: Are we there yet?

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