Ketones

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Ketones

Ketones is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. The carbonyl carbon of the ketone group is sp2 hybridized. The structure of ketones is a trigonal planar centered around the carbonyl carbon. Ketones are widespread in nature and are often combined with other functional groups. The following figures show the examples of naturally occurring molecules which contain ketone functional group. The chemicals in the figure 1 are found chiefly in plants or microorganisms and the compounds in the figure 2 have animal origins [1].

Ketone containing molecules isolated from plant sourcesFig. 1 Ketone containing molecules isolated from plant sources

Ketone containing molecules isolated from animal sourcesFig. 2 Ketone containing molecules isolated from animal sources

Synthesis Methods of Ketones

Important ketones include methyl ethyl ketone (also called butanone) and cyclohexanone. We take these two ketones as examples to illustrate the synthesis methods of ketones from biomass-derived feedstock.

  • Methyl ethyl ketone

Methyl ethyl ketone appears as colorless fairly volatile liquid with a pleasant pungent odor, and it can be used in the manufacture of synthetic rubber, paraffin wax, and to make other chemical products. Microbial fermentation is an attractive way to produce 2,3-butanediol, which was then converted to methyl ethyl ketone by dehydration over a solid acid catalyst. The fermentation process can be performed using the bacteria Klebsiella oxytoca. 2,3-Butanediol then is dehydrated to form methyl ethyl ketone on a solid acid catalyst, the proton form of ZSM-5 [2].

  • Cyclohexanone

Cyclohexanone is a key raw material for producing nylon 6 and nylon 66 and for synthesis of other chemicals. It has been reported that cyclohexanone and its derivatives can be obtained via hydrogenation and hydrolysis processes from aromatic ethers (derived from biomass) under the catalysis of bromide salt-modified Pd/C. Besides, the yields of cyclohexanone derivatives produced from the aromatic ethers, which can be extracted from plants or derived from lignin, are also satisfactory [3].

Applications

Biobased ketones are widely used in various industries. They can be used as reactants to produce complex chemicals, such as ketone ammonia, cyanohydrins, mixed aldols. They can be used as solvents in lacquers, paints, tanning, hydraulic fluids, and textiles. Besides, they can be used in food and medicine industries. In addition, certain ketones such as progesterone, testosterone, cortisone, and aldosterone are all steroid hormones which possess vital roles for humans or other living beings to promote health runs. Furthermore, Ketones are also commonly employed in the beauty industry like chemical peeling and acne treatments.

Applications

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References

  1. Natural Occurrence of Aldehydes and Ketones. The LibreTexts libraries.
  2. Multer, A., McGraw, N., Hohn, K., & Vadlani, P. Production of Methyl Ethyl Ketone from Biomass Using a Hybrid Biochemical/Catalytic Approach. Ind. Eng. Chem. Res. 2013, 52, 1, 56-60.
  3. Meng, Q., Hou, M., Liu, H. et al. Synthesis of ketones from biomass-derived feedstock. Nat Commun 8, 14190 (2017).

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