Anhydro Sugar Formation in Acid and Base Hydrolyses of 3,4-Di-O-methylsulfonyl-D-mannitol: a Rapid Route to 1,4:3,6-Dianhydro-D-iditol(D-Isoidide)

1974 ◽  
Vol 52 (19) ◽  
pp. 3367-3372 ◽  
Author(s):  
David Roy Hicks ◽  
Bert Fraser-Reid
Keyword(s):  
Acid Hydrolysis ◽  
Ester Group ◽  
Sulfonate Group ◽  
Acid And Base ◽  
Hydrolysis Of

Brief acid hydrolysis of 1,2:5,6-di-O-isopropylidene-3,4-di-O-methylsulfonyl-D-mannitol (1a), removes the isopropylidene groups giving the disulfonated hexitol, 2a. Upon continued acid hydrolysis of 2a, one sulfonate group is lost with formation of a sulfonated monoanhydro hexitol, 5a, then the second ester group is lost to give 1,4:3,6-dianhydro-D-iditol (D-isoidide, 3a). If the disulfonate, 2a, is treated with base, an isomeric dianhydro hexitol, the bisoxirane 4, is formed. Under similar basic conditions, the monoanhydro hexitol, 5a, is stable. On acid hydrolysis, the bisoxirane, 4, gives hexitols and only 20% of D-isoidide, which indicates that 4 cannot be an intermediate in the conversion of 2a to 3a. These results indicate that, in 2a at least, five-membered anhydro rings are formed preferentially in acid hydrolyses and three-membered rings in saponification.The stage and course of hydrolysis of 2a are readily monitored by observing the τ 4–6 region in the n.m.r. spectra of D2O samples of the hydrolysate.

Selective acid hydrolysis of 2,4,6-trimethylbenzyl esters and its application in peptide synthesis

1966 ◽  
Vol 19 (8) ◽  
pp. 1511 ◽  
Author(s):  
FHC Stewart
Keyword(s):  
Acid Hydrolysis ◽  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Ester Group ◽  
Protecting Groups ◽  
Alkaline Conditions ◽  
Hydrolysis Of

Experiments with various N-acylamino acid 2,4,6-trimethylbenzyl esters have shown that the ester group is cleaved selectively by cold trifluoroacetic acid without affecting benzyloxycarbonyl, formyl, or phthaloyl amino-protecting groups present. The possible value of this selective behaviour in peptide syntheses where the use of alkaline conditions would be detrimental is illustrated by the synthesis of certain dipeptide derivatives.

Partial hydrolysis of acyl 1,6-anhydro-β-D-glucopyranose

1984 ◽  
Vol 49 (8) ◽  
pp. 1780-1787 ◽  
Author(s):  
Štefan Kučár ◽  
Juraj Zámocký ◽  
Juraj Zemek ◽  
Dušan Anderle ◽  
Mária Matulová
Keyword(s):  
Acid Hydrolysis ◽  
Hydrazine Hydrate ◽  
Hydrogen Chloride ◽  
Ester Group ◽  
The Other ◽  
Hydroxyl Group ◽  
Partial Hydrolysis ◽  
Substantial Influence ◽  
Hydrolysis Of ◽  
Derivatives Of

Partial hydrolysis of per-O-acetyl- and per-O-benzoyl derivatives of 1,6-anhydro-β-D-glucopyranose with methanolic hydrogen chloride and hydrazine hydrate was investigated. The acyl group at C(3) is of substantial influence on the course of hydrolysis. The esterified hydroxyl group at C(3) was found to be most stable on acid hydrolysis with methanolic hydrogen chloride when compared with that at C(2), or C(4); on the other hand, this ester group is the most labile upon hydrolysis with hydrazine hydrate. Selectivity of the respective ester groups towards hydrolysis made it possible to prepare all variations of acetyl and benzoyl derivatives of 1,6-anhydro-β-D-glucopyranose.

Photooxygenation of nitrobenzyl derivatives. Mechanisms of photogeneration and hydrolysis of α-hydroperoxy nitrobenzyl ethers

1987 ◽  
Vol 65 (8) ◽  
pp. 1775-1783 ◽  
Author(s):  
Peter Wan ◽  
S. Muralidharan ◽  
Iain McAuley ◽  
Christopher A. Babbage
Keyword(s):  
Aqueous Solution ◽  
Hydrogen Peroxide ◽  
Acid Hydrolysis ◽  
Quantum Yields ◽  
Acid And Base ◽  
Hydrolysis Of

The photooxygenation of nitrobenzyl derivatives 1–10 has been studied in aqueous solution as a function of pH. For m-nitrobenzyl ethers 2–4 and 9, stable α-hydroperoxy ethers (11–13) are the primary photochemical products. Acid hydrolysis of 11–13 gives m-nitrobenzaldehyde and hydrogen peroxide. Quantum yields for photooxygenation are reported for a number of derivatives as a function of pH. Acid and base catalyses of photooxygenation are observed for several compounds. A mechanism involving photogenerated nitrobenzyl carbanion intermediates is proposed.

DETERMINATION OF MICRO-AMOUNTS OF 5β-PREGNAN-3α-OL-20-ONE IN URINE USING INFRARED-SPECTROMETRY

1962 ◽  
Vol 41 (2) ◽  
pp. 234-246 ◽  
Author(s):  
H. J. van der Molen
Keyword(s):  
Infrared Spectrum ◽  
Quantitative Determination ◽  
Acid Hydrolysis ◽  
Chromatographic Separation ◽  
Pure Form ◽  
Infrared Spectrometry ◽  
Hydrolysis Of

ABSTRACT A procedure for the quantitative determination of 5β-pregnan-3α-ol-20-one in urine is described. After acid hydrolysis of the pregnanolone-conjugates in urine, the free steroids are extracted with toluene. Pregnanolone is isolated in a pure form as its acetate; after chromatographic separation of the free steroids on alumina, the fraction containing pregnanolone is acetylated and rechromatographed on alumina. Quantitative determination of the isolated pregnanolone-acetate is carried out with the aid of the infrared spectrum recorded by a micro KBr-wafermethod. The reliability of the method under various conditions is discussed under the headings, specificity, accuracy, precision and sensitivity. It is possible to determine 30–40 μg pregnanolone in a 24-hours urine portion with a precision of 25%.

Optimization of technological modes of cold acid hydrolysis of potato starch

2020 ◽  
Vol 26 (3) ◽  
pp. 222-233
Author(s):  
M. Alekseenko ◽  
V. Litvyak ◽  
A. Sysa ◽  
E. Hrabovska ◽  
O. Galenko
Keyword(s):  
Acid Hydrolysis ◽  
Potato Starch ◽  
Hydrolysis Of

FLOWTHROUGH ACID HYDROLYSIS OF RAPESEED STALKS

2012 ◽  
Vol 11 (12) ◽  
pp. 2313-2318
Author(s):  
Theodor Malutan ◽  
Adina Elena Panzariu
Keyword(s):  
Acid Hydrolysis ◽  
Hydrolysis Of

scholarly journals Tagasaste, leucaena and paulownia: three industrial crops for energy and hemicelluloses production

2021 ◽  
Vol 14 (1) ◽  
Author(s):  
Alberto Palma ◽  
Javier Mauricio Loaiza ◽  
Manuel J. Díaz ◽  
Juan Carlos García ◽  
Inmaculada Giráldez ◽  
...  
Keyword(s):  
Activation Energy ◽  
Acid Hydrolysis ◽  
Energy Production ◽  
Combustion Process ◽  
Operating Conditions ◽  
Raw Material ◽  
Energy Of Combustion ◽  
Increasing Temperature ◽  
Hydrolysis Of ◽  
Chamaecytisus Proliferus

Abstract Background Burning fast-growing trees for energy production can be an effective alternative to coal combustion. Thus, lignocellulosic material, which can be used to obtain chemicals with a high added value, is highly abundant, easily renewed and usually inexpensive. In this work, hemicellulose extraction by acid hydrolysis of plant biomass from three different crops (Chamaecytisus proliferus, Leucaena diversifolia and Paulownia trihybrid) was modelled and the resulting solid residues were used for energy production. Results The influence of the nature of the lignocellulosic raw material and the operating conditions used to extract the hemicellulose fraction on the heat capacity and activation energy of the subsequent combustion process was examined. The heat power and the activation energy of the combustion process were found to depend markedly on the hemicellulose content of the raw material. Thus, a low content in hemicelluloses resulted in a lower increased energy yield after acid hydrolysis stage. The process was also influenced by the operating conditions of the acid hydrolysis treatment, which increased the gross calorific value (GCV) of the solid residue by 0.6–9.7% relative to the starting material. In addition, the activation energy of combustion of the acid hydrolysis residues from Chamaecytisus proliferus (Tagasaste) and Paulownia trihybrid (Paulownia) was considerably lower than that for the starting materials, the difference increasing with increasing degree of conversion as well as with increasing temperature and acid concentration in the acid hydrolysis. The activation energy of combustion of the solid residues from acid hydrolysis of tagasaste and paulownia decreased markedly with increasing degree of conversion, and also with increasing temperature and acid concentration in the acid hydrolysis treatment. No similar trend was observed in Leucaena diversifolia (Leucaena) owing to its low content in hemicelluloses. Conclusions Acid hydrolysis of tagasaste, leucaena and paulownia provided a valorizable liquor containing a large amount of hemicelluloses and a solid residue with an increased heat power amenable to efficient valorization by combustion. There are many potential applications of the hemicelluloses-rich and lignin-rich fraction, for example as multi-components of bio-based feedstocks for 3D printing, for energy and other value-added chemicals.

Sign in / Sign up

Export Citation Format

Share Document