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Review
. 2023 Nov 27:11:1306182.
doi: 10.3389/fchem.2023.1306182. eCollection 2023.

Mechanochemistry and oleochemistry: a green combination for the production of high-value small chemicals

Christophe Len  1   2 , Vaishaly Duhan  3 , Weiyi Ouyang  1 , Remi Nguyen  2 , Bimlesh Lochab  3
Affiliations
Review

Mechanochemistry and oleochemistry: a green combination for the production of high-value small chemicals

Christophe Len et al. Front Chem. .

Abstract

Mechanochemistry and oleochemistry and their combination have been known for centuries. Nevertheless, bioeconomy and circular economy concepts is much more recent and has motivated a regain of interest of dedicated research to improve alternative technologies for the valorization of biomass feedstocks. Accordingly, this review paper aims essentially at outlining recent breakthroughs obtained in the field of mechanochemistry and oleochemicals such as triglycerides, fatty acids, and glycerol derivatives. The review discusses advances obtained in the production of small chemicals derived from oils with a brief overview of vegetable oils, mechanochemistry and the use of mechanochemistry for the synthesis of biodiesel, lipidyl-cyclodextrine, dimeric and labelled fatty acids, calcium diglyceroxide, acylglycerols, benzoxazine and solketal. The paper also briefly overviews advances and limits for an industrial application.

Keywords: batch reactor; continuous flow reactor; glycerol; mechanochemistry; vegetable oil.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest. The author(s) declared that they were an editorial board member of Frontiers, at the time of submission. This had no impact on the peer review process and the final decision.

Figures

FIGURE 1
FIGURE 1
Main fatty acids present in the composition of vegetable oils.
FIGURE 2
FIGURE 2
Main chemical reactive sites of unsaturated triglycerides.
FIGURE 3
FIGURE 3
Roadmap to selected bio-based C3 chemicals starting from glycerol and their applications (Varma and Len, 2019).
FIGURE 4
FIGURE 4
Most utilized types of grinding and milling equipment. (A) Mortar and pestle. (B) Automatic mortar. (C) Vertical vibrational mini-mill. (D) Vibratory micro-mill. (E) Vibrational ball mill. (F) Vibrational ball mill with temperature. (G) Planetary ball mill. (H) Multisample mill. (I) Twin screw for continuous mechanochemical synthesis. (J) Continuous flow heated mechanochemical reactor.
FIGURE 5
FIGURE 5
Basic concept for ball impact energy in mechanochemical synthesis (Wang et al., 2023).
SCHEME 1
SCHEME 1
General chemical equation of the biodiesel formation.
SCHEME 2
SCHEME 2
Semi-continuous biodiesel production catalyzed by CaDG using a high-throughput reactor filles with beads (Malpartida et al., 2020b; Malpartida et al., 2020).
SCHEME 3
SCHEME 3
Synthesis of bicaternary lipidyl-cyclodextrins from oleic acid in 3 steps via ring-opening of methyl oleate epoxide by vibrating ball-milling in a mixer mill (Oliva et al., 2020).
SCHEME 4
SCHEME 4
Continuous dimerization of soybean fatty acid using a horizontal ball-mill reactor (Lu et al., 2019).
SCHEME 5
SCHEME 5
Synthesis of labeled oleic acid by vibrating ball-milling in a mixer mill (Spackova et al., 2020).
SCHEME 6
SCHEME 6
Synthesis of labeled stearic acid by vibrating ball-milling in a mixer mill (Spackova et al., 2020).
FIGURE 6
FIGURE 6
Synthesis of labeled fatty acids by vibrating ball-milling in a mixer mill (Spackova et al., 2021).
FIGURE 7
FIGURE 7
Labeled polyunsaturated fatty acids obtained by vibrating ball-milling in a mixer mill (Spackova et al., 2021).
SCHEME 7
SCHEME 7
Synthesis of acetylene and CaDG starting from calcium carbide and glycerol in a planetary ball mill (Li et al., 2018).
SCHEME 8
SCHEME 8
Silylation of glycidol with TBDMSCl by vibrating ball-milling in a mixer mill or in a planetary ball mill (Ardila-Fierro et al., 2019).
SCHEME 9
SCHEME 9
Cobalt-catalyzed ring-opening of epoxide by vibrating ball-milling in a mixer mill (Ardila-Fierro et al., 2019).
SCHEME 10
SCHEME 10
Mechanical synthesis of DAG obtained by vibrating ball-milling in a mixer mill (Ardila-Fierro et al., 2019).
FIGURE 8
FIGURE 8
Different DAGs obtained by vibrating ball-milling in a mixer mill (Ardila-Fierro et al., 2019).
SCHEME 11
SCHEME 11
Conjugation of DAG with 7-hydroxycoumarin by vibrating ball-milling in a mixer mill (Ardila-Fierro et al., 2019).
SCHEME 12
SCHEME 12
Synthesis of benzoxazine from glycerol using successive mechanochemistry in ball mill and microwave irradiation (Torres-Pastor et al., 2022).
SCHEME 13
SCHEME 13
General ketalization of glycerol with acetone in acid conditions.
FIGURE 9
FIGURE 9
Twelve principles of green chemistry and mechanochemistry inputs.
See this image and copyright information in PMC

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