Configuration of the 2,3-Butylene Glycols<sup>1</sup>

Morell, Sam; Auernheimer, A. H.

doi:10.1021/ja01233a040

Cited by 21 publications

(4 citation statements)

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“…and refractive index exhibited by the three preparations of 2:3-butylene glycol are due to the different proportions of the dand meso-isomers present in the mixtures. The product obtained in the present work appears to contain more of the d-isomer than the glycols isolated by Harden & Walpole (1906) or Morell & Auerheimer (1944). Its content of the d-isomer is calculated from the optical rotation data to be approximately 14%.-2:3-Butylene glycol diphenylurethane and dibenzoate were prepared by treatment with phenylisocyanate and benzoyl chloride, respectively.…”

Section: Effect Of Aeration On Fermentation Co Co Co -_ Cmentioning

confidence: 45%

The fermentation of sucrose by Aerobacter aerogenes

Freeman¹

1947

Biochemical Journal

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The production of 2:3-butylene glycol as a bacterial metabolic product from carbohydrate was first observed by Harden & Walpole (1906) and Walpole (1911), but received comparatively little further attention until the second world war when the formation of this product as an intermediate for butadiene, synthetic rubber and other purposes was investigated in considerable detail. Recent work in Canada and the U.S.A. (Adams & Stanier, 1945; Perlman, 1944; Stanier & Adams, 1944; Ward, Pettijohn & Coghill, 1945), has established the characteristics of three distinct fermentations yielding 2:3-butylene glycol: (a) the Aerobacter aerogenes fermentation of hexoses yielding a mixture of d-and meso-isomers of the glycol, in which the latter predominates as the main non-gaseous product, (b) the Aerobacillus polymyxa fermentation of starches and dilute sugar solutions which yields 1-2:3-butylene glycol and ethanol, and (c) the Aeromonas hydrophila fermentation in which an 1and meso-mixture of 2:3-butylene glycol isomers, ethanol, and lactic acid are the main non-gaseous products. The object of the present investigation was to study the production of dand meso-2:3-butylene glycol from Aerobacter aerogenes fermentations of sucrose as the basis for a technical method using molasses. The factors influencing rate of fermentation and yield ofproduct have been investigatedwith a view to decreasing the time necessary for complete fermentation and simplifying the culture medium. EXPERIMENTAL Composition of media Although the early workers used complex nutrients such as peptone as a basis for the culture media it is now well known that A. aerogenes grows well on simple media containing citrate or glucose as carbon source and nitrates or ammonium salts as source of nitrogen (Koser, 1924; Lodge & Hinshelwood, 1944). The basal medium used in the present work was based on the formulae of Koser (1924) and of Czapek (as modified by Dox (1910)) and had the following composition: g. Sucrose 100 Dipotassium hydrogen phosphate (K2HPO4) 2-5 Ammonium sulphate 4-0 Magnesium sulphate (MgSO4. 7H20) 0.1 Potassium chloride 05 Ferrous sulphate (FeSO4 *7H20) 0 01 Water to 1000 ml.

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Section: Effect Of Aeration On Fermentation Co Co Co -_ Cmentioning

confidence: 45%

The fermentation of sucrose by Aerobacter aerogenes

Freeman¹

1947

Biochemical Journal

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“…Hydrogenation of A^-androstene-SCd),17(a)diol-16-one diacetate with Raney nickel in ethanol (Stodola, et al 1) or in ethyl acetate-ethanol (our confirmation) yields Butenandt's triol.7 Since this triol is known to be cts-oid at Cw-Cp,7 its structure must be A*-androstene-3(/9), 16(a), 17-(a)-triol.…”

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confidence: 99%

On the Maximum in the Equivalent Conductivity of Two Paraffin-Chain Salts in Water

Brown¹,

Pf²

1947

J. Am. Chem. Soc.

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“…The hydrogenations of butylvinylcarbinol (126) with colloidal platinum in acetic acid and of methylvinylcarbinol (150) with platinum oxide yield 3-heptanol and 2-butanol with little or no loss in optical purity.…”

Section: B Miscellaneous Catalytic Reactionsmentioning

confidence: 99%