Butanol and Acetone

More than seventy years ago the impressive discovery was made that bioreduction of mannitol, glycerol and starch yields butanol. Fermentations in which butyric acid, butanol and acetone are formed from carbohydrates by different bacilli (butyl bacteria) belong in this group. The term butyl bacteria as a generic name for microbes producing the genetically related substances of the four-carbon series was proposed in 1921" and has been applied since then. The approximate course of these reactions is shown by the following formulations which, however, do not explain the mechanism ... 

The pentose sugars, as well as the hexoses, are utilized by acetone-and butyl alcohol-producing organisms. Partansky and Henry reported the production of butanol and acetone from wood sugars. This work was continued in the laboratory of W. H. Peterson of the University of Wisconsin. Tables VIII and IX summarize their findings with two organisms. 

Whey permeate may also be fermented anaerobically to fuel gas. Studies have also been reported on the production of ammonium lactate by continuous fermentation of deproteinized whey to lactic acid followed by neutralization with ammonia. Conversion of whey and whey permeate to oil and single-cell protein with strains of Candida curvata and Trichosporon cutaneum have been examined. Production of the solvents n-butanol and acetone by Clostridium acetobutylicum or C. butyricum is under investigation in New Zealand. Whey permeate also has potential for citric acid and acrylic acid manufacture. Extracellular microbial polysaccharide production from whey permeate has... 

Sunlight irradiation (solar photochemical synthesis) of 1,4-naphthoquinone (27) in the presence of aldehyde (28) in a mixture of -butanol and acetone gives a good yield of the corresponding acyl hydroquinone (29) through the abstraction of the formyl hydrogen atom of aldehyde by the excited triplet biradical derived from 1,4-naphthoquinone, followed by the reaction of the acyl radical with 1,4-naphthoquinone (eq. 12.7). Here,... 

First production of neat lactic acid by industrial fermentation Public wastewater treatment plants Industrial production of butanol and acetone by aseptic fermentation... 

Recently Manahan and Iwamoto° ° determined the stability constants of the chloride complexes of Cu(I) and Cu(II) in methanol, ethanol, 2-propanol, 2-butanol, and acetone by observing shifts in values. Although a constant ionic strength medium of 0.1 M (LiC104 + LiCl) was used and ion-association was neglected, the results are of interest since they indicate a small decrease in solvation energy for Cu(I) in going from H2O to the solvents in the order listed above. The half-wave potential data show that the solvation of Cu(II) is similar to Cu(I). The stability of the chloride complexes of both Cu(I) and Cu(II) increases in the order... 

Nair, R.V, Green, E.M., Watson, D.E., Bennett, G.N. et al (1999) Regulation of the sol locus genes for butanol and acetone formation in Clostridium ace-tobutylicum ATCC 824 by a putative transcriptional repressor. J. Bacteriol,... 

Solvents are not dominating compounds in the biosphere of our planet. Under natural conditions, their presence in appreciable amounts is restricted to specific areas. Only a very limited number of solvents is of biological origin and some may reach higher concentrations in nature. The best known example is ethanol. However, also butanol and acetone can be... 

The ending of the Second World War, in 1945, was the beginning of a drastically decline of the industrial butanol and acetone production by ABE fermentation. Between the years of 1950 and 1960 the solvent production by fermentation almost... 

Killeffer DH. (1927). Butanol and acetone from corn-a description of the fermentation process. Industrial Engineering Chemistry, 19, 46-50. 

Vane LM, Alvarez FR, Rosenblum L, Govindaswamy S. Hybrid vapor stripping-vapor permeation process for recovery and dehydration of 1-butanol and acetone/butanol/ethanol from dilute aqueous solutions. Part 2. Experimental validation with simple mixtures and actual fermentation broth. J Chem Technol Biotechnol 2013 88 1448-58. 

The title sounds simple enough, but it really involves talking about the past, the present and the future. In addition, the term "solvents" could cover a multitude of compounds and this review is going to consider only a few in fact, the focus is concerned mainly with three - ethanol, butanol and acetone. The other word in the title is"fermentation"- so that fixes the parameters. 

Polyhydroxybutyric acid is a storage compound for excess carbon in many microorganisms (E 2.2). It may be used in the production of plastics (F 4). Acetoacetic acid, acetone, and /S-hydroxybutyric acid are excreted in the urine of people with a pathologically high blood sugar level (diabetes mellitus) (E 1). Their appearance is of diagnostic value. Butyric acid, butanol, and acetone are products of microbial fermentations. 

This continual modification of the process allowed it to compete with the petrochemical synthesis of butanol and acetone (see sections 9.8.1 and 9.9.7 of Vol. I) (Figure 6.6), until molasses found a competing use as an animal feed and its price began to rise. British production stopped in 1957, but the process survives in South Africa and Taiwan, where oil supplies are limited. A process which made use of waste cellulose might still be economic. However, its main legacy to biotechnology lies in that early phase of its development which laid the foundations of the modern fermentation industry. 

This process is now only of historical interest. Like the fermentation of butanol and acetone it has succumbed to advances in chemistry. However, it illustrates the other important feature of microbial transformations, which is their stereoselectivity. This, together with the regioselectivity apparent in the oxidation of sorbitol, is an important argument in favour of biological catalysis. 

Water, 2-butanol and acetone are determined by gas chromatography using a Varian CX 300 Star gas chromatograph with a Porapak-Q packed column and a thermal conductivity detector the hydrogen flow rate was 30 cm min and the column temperature was 180°C. However, the salt cannot be allowed in the packed column or in the detector. So, an empty column section of 30 cm is placed before the paeked column. The salt is deposed on the inner walls of this empty eolumn, being eliminated from the gas stream. Periodically, this section is washed with distillated water and acetone, and further dried at 120°C. 

A solution that is 95% ethyl alcohol (190 proof) may be obtained from the final mixture by fractional distillation. The mixture also yields two other products of commercial value today 1-butanol and acetone (Section 21.11). 

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