STUDIES ON RDX AND RELATED COMPOUNDS: X. ANALYSIS FOR NITRIC ACID IN ACETIC ACID – ACETIC ANHYDRIDE MEDIA

1953 ◽  
Vol 31 (3) ◽  
pp. 214-215 ◽  
Author(s):  
R. A. Marcus ◽  
C. A. Winkler
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Analytical Method ◽  
Potassium Acetate ◽  
Standard Solution ◽  
Related Compounds

An analytical method has been developed for the estimation of nitric acid in acetic acid – acetic anhydride media, with a precision of 0.3%. The procedure involves the addition of a solution of potassium acetate in acetic acid to the sample. The excess is back-titrated conductometrically with a standard solution of nitric acid in acetic acid.

STUDIES OF RDX AND RELATED COMPOUNDS: III. THE REACTION TO FORM RDX FROM AMMONIUM NITRATE AND FORMALDEHYDE IN ACETIC ANHYDRIDE

1951 ◽  
Vol 29 (5) ◽  
pp. 377-381 ◽  
Author(s):  
A. Gillies ◽  
H. L. Williams ◽  
C. A. Winkler
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Ammonium Nitrate ◽  
Glacial Acetic Acid ◽  
Related Compounds

This reaction at 35°C. exhibits a behavior indicative of the presence of an intermediate in the reaction. Reaction of paraformaldehyde and ammonium nitrate in glacial acetic acid resulted in the isolation of hexamine dinitrate. Evidence is presented to indicate that formation of hexamine dinitrate, accompanied by the production of nitric acid, is responsible for the production of RDX in the acetic anhydride system.

REACTIONS OF 2-ACETOXY-4,6-DI-O-ACETYL-3-O-(2,6-DICHLOROBENZOYL)-D-GLUCAL, TRI-O-ACETYL-3-DEOXY-α-D-erythro-HEX-2-ENOPYRANOSYL CHLORIDE, AND RELATED COMPOUNDS

1966 ◽  
Vol 44 (15) ◽  
pp. 1855-1862 ◽  
Author(s):  
R. U. Lemieux ◽  
R. J. Bose
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Acetic Anhydride ◽  
Potassium Acetate ◽  
Equimolar Mixture ◽  
Related Compounds ◽  
Reaction Compound

Attempts to dehydrobrominate tri-O-acetyl-3-O-tosyl-α-D-glucopyranosyl bromide with diethylamine led directly to products resulting from the replacement of the tosyloxy group by the diethylamine. It was readily possible to prepare 2-acetoxy-di-O-acetyl-3-(2,6-dichlorobenzoyl)-D-glucal (V). Acetolysis of this compound gave an equimolar mixture of the α- and β-anomers (II and VI, respectively) of 2-acetoxy-di-O-acetyl-pseudo-D-glucal as the first products of the reaction. Compound V reacted only reluctantly with methanol in pyridine to give a mixture of the anomeric methyl di-O-acetyl-3-deoxy-D-erythro-hex-2-enopyranosides. These glycosides were readily prepared by reaction of tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-eno-pyranosyl chloride with methanol in the presence of pyridine. 2-Acetoxy-di-O-acetyl-3-O-mesitoyl-D-glucal was prepared from 3-O-mesitoyl-β-D-glucose. The anomerizations of compounds II and VI were examined with both sulfuric acid in 1:1 acetic acid – acetic anhydride and potassium acetate in acetic acid. The conformations of II and VI are discussed, as are a number of the mechanistic features of the reactions studied.

STUDIES ON RDX AND RELATED COMPOUNDS: II. THE NITROLYSIS OF HEXAMINE IN ACETIC ACID

1950 ◽  
Vol 28b (11) ◽  
pp. 715-719 ◽  
Author(s):  
C. A. Winkler ◽  
M. Kirsch
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Deleterious Effect ◽  
Reaction Rate ◽  
Harmful Effect ◽  
Maximum Yield ◽  
Related Compounds

Acetic acid has a harmful effect on the reaction rate and on the yield of RDX at 1 °C. and at 30 °C. for a given nitric acid – hexamine ratio below a certain optimum value. At the optimum, however, the maximum yield of 80% is obtained at both temperatures. The deleterious effect of acetic acid may be explained by assuming that the concentration of the active nitrolyzing agent (nitracidium ion) is decreased by reaction between acetic acid and nitric acid.

STUDIES ON LIGNIN AND RELATED COMPOUNDS: IV. THE NITRATION OF GLYCOL-LIGNIN

1930 ◽  
Vol 3 (2) ◽  
pp. 130-139 ◽  
Author(s):  
Harold Hibbert ◽  
Leo Marion
Keyword(s):  
Nitric Acid ◽  
Acetic Anhydride ◽  
Nitro Group ◽  
Nitroso Compound ◽  
Initial Oxidation ◽  
Percentage Composition ◽  
Acidic Component ◽  
Fuming Nitric Acid ◽  
Related Compounds

Glycol-lignin at temperatures below 0 °C., dissolves completely in a mixture of four parts of acetic anhydride and one part of fuming nitric acid, giving rise to a 125% yield of a product (nitrated-lignin) which has undergone nitration and acetylation. The nitrogen in the product is present partly in the form of a nitro group, an ester of nitric acid, a nitroso compound and in another form not yet determined. A further treatment of this nitrated-lignin with a nitrating liquor of the same composition, followed by heating at 80 °C. causes a short initial oxidation, and yields a substance differing slightly from the first and having a C:H ratio almost 1:1. Repetition of the treatment does not seem to alter the percentage composition appreciably, until after the fourth treatment.Nitrated-lignin can be methylated, the methoxyl content of the product being more than double that of the original nitrated-lignin. It can also be reduced, the resulting product diazotized and coupled with β-naphthol disulphonic acid.The soluble products of the nitration reaction contain an acidic component which has not been identified.

scholarly journals STUDIES ON RDX AND RELATED COMPOUNDS: IX. DETERMINATION OF NITRIC ACID AND ACETIC ANHYDRIDE IN BACHMANN LIQUORS

1953 ◽  
Vol 31 (3) ◽  
pp. 201-203
Author(s):  
R. H. Betts ◽  
R. S. Stuart ◽  
C. A. Winkler
Keyword(s):  
Nitric Acid ◽  
Acetic Anhydride ◽  
Ammonium Nitrate ◽  
Routine Analysis ◽  
Calcium Hypochlorite ◽  
Electrometric Method ◽  
Direct Titration ◽  
Related Compounds ◽  
External Indicator

An electrometric method for determination of nitric acid in RDX(B) liquors has been developed. The method is not largely affected by ammonium nitrate and acetic anhydride. A precision of ± 0.5% may be readily obtained. Acetic anhydride in RDX(B) liquors may be determined by direct titration with standard aniline–toluene solution at 0 °C., using calcium hypochlorite as an external indicator. In routine analysis, a precision of ± 2% may be obtained.

scholarly journals On the Reaction of 4-(2'-Furyl)pyrimidine with Nitric Acid in Acetic Anhydride-Acetic Acid.

1967 ◽  
Vol 21 ◽  
pp. 2296-2298 ◽  
Author(s):  
Salo Gronowitz ◽  
Anders Hallberg ◽  
J. Sandström ◽  
S. J. Cyvin ◽  
G. Hagen
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride

SYNTHESIS OF 2-, AND 3-NITROBENZANTHRONE VIA DIRECT NITRATION OF BENZANTHRONE WITH NITRIC ACID/ACETIC ACID

2019 ◽  
Vol 71 (1) ◽  
Author(s):  
Kefa K. Onchoke ◽  
Jorge J. Ojeda
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Standard Sample ◽  
Major Product ◽  
Fragmentation Patterns

Abstract Three mono-nitrobenzanthrone isomers (1-, 2-, and 3-nitrobenzanthrone; 1-, 2-, and 3-NBA) were synthesized by reacting benzanthrone (BA) with nitric acid (HNO3) in acetic anhydride at ice-cold conditions. The major product, 2-nitrobenzanthrone (2-NBA), was confirmed using GC-MS via comparisons with a standard sample. On the basis of the elution profiles and fragmentation patterns two other isomers formed were assigned to 1-, and 3-nitrobenzanthrone (1-, and 3-NBA). The average percent yields of 1-, 2-, and 3-NBA were 0.3 ± 0.1%, 10.5 ± 2.6 %, and 6.4 ± 1.3 %, respectively.

The Nitration of α- and β-Acylnaphthalenes

1995 ◽  
Vol 48 (12) ◽  
pp. 1969 ◽  
Author(s):  
SD Barker ◽  
K Wilson ◽  
RK Norris
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Nitro Compound ◽  
Nitro Compounds ◽  
The Other ◽  
Coupling Constant ◽  
Significant Extent ◽  
Nitro Derivatives ◽  
High Yields

The nitration of α- and β- acylnaphthalenes with copper(II) nitrate in acetic anhydride or nitric acid/acetic acid mixtures gives high yields of the corresponding mononitro compounds. The assignment of constitution to these products is made on the basis of extensive 1H n.m.r. chemicl shift and coupling constant data. In the case of α- acylnaphthalenes, with the notable exception of α- pivalonaphthone, nitration occurs in the α-positions of the unsubstituted ring to give mixtures of 5- and 8-nitro compounds. α- Pivalonaphthone gives appreciable amounts of the 4-nitro compound and also of the 8-nitro compound. This result indicates that the pivaloyl group does not shield the 8-position sterically to any significant extent and is effectively electronically neutral, unlike the other acyl substituents , in allowing attack at the α-position (position 4) of the acylated ring. This result is ascribable to the lack of coplanarity of the pivaloyl group with the naphthalene system. All of the β- acylnaphthalenes gave mixtures of 4-, 5- and 8-nitro derivatives in proportions that did not vary significantly with the nature of the acyl group.

Adduct Intermediates in the Side-chain Nitration of 1,4-Dimethylnaphthalene

1972 ◽  
Vol 50 (24) ◽  
pp. 3988-3992 ◽  
Author(s):  
Alfred Fischer ◽  
Alan Leslie Wilkinson
Keyword(s):  
Acetic Acid ◽  
Nitric Acid ◽  
Acetic Anhydride ◽  
Room Temperature ◽  
Methylene Chloride ◽  
Side Chain ◽  
Trans Isomers ◽  
Cis And Trans Isomers ◽  
Cis And Trans ◽  
Naphthyl Acetate

cis and trans isomers of 1,4-dimethyl-4-nitro-1,4-dihydro-1-naphthyl acetate (1) have been isolated from a mixture of 1,4-dimethylnaphthalene and nitric acid in acetic anhydride by quenching at −40°. At room temperature only 1-methyl-4-nitromethylnaphthalene (4) is obtained. The conversion of 1,4-dimethylnaphthalene to 4 and of the cis (1a) and trans (1b) adducts to 4, by nitric acid in acetic anhydride, has been followed by n.m.r. 1,4-Dimethyl-4-nitro-1,4-dihydro-1-naphthyl nitrate (5) appears to be the immediate product from nitration of 1,4-dimethylnaphthalene in acetic anhydride, methylene chloride, or nitromethane. In acetic anhydride 5 is converted into 1. Decomposition of 1 in acetic acid gives 1,4-dimethyl-2-naphthyl acetate and some 4. The formation of 4 in this reaction is suppressed by urea.

Sign in / Sign up

Export Citation Format

Share Document