Nitrate-acetate esters

As esters the alkyl halides are hydrolysed by alkalis to alcohols and salts of halogen acids. They are converted by nascent hydrogen into hydrocarbons, by ammonia into amines, by alkoxides into ethers, by alkali hydrogen sulphides into mercaptans, by potassium cyanide into nitriles, and by sodium acetate into acetic esters. (Formulate these reactions.) The alkyl halides are practically insoluble in water but are, on the other hand, miscible with organic solvents. As a consequence of the great affinity of iodine for silver, the alkyl iodides are almost instantaneously decomposed by aqueous-alcoholic silver nitrate solution, and so yield silver iodide and alcohol. The important method of Ziesel for the quantitative determination of alkyl groups combined in the form of ethers, depends on this property (cf. p. 80). 

Marans and Preckel " synthesized both the mononitrate (95) and the dinitrate (92) esters of metriol by using a similar strategy to that used for pentaerythritol trinitrate. Thus, nitration of both the mono- (90) and the di- (93) acetate esters of metriol, followed by selective hydrolysis of the acetate groups, yields (92) and (95) respectively the latter could be useful as a monomer for the synthesis of energetic polyurethane polymers. 

Synthetic Membrane Appropriate inert and commercially available synthetic membranes such as polysulfone, cellulose acetate/nitrate mixed ester, or Polytetrafluoroethylene 70 Fm membrane of appropriate size to fit the diffusion cell diameter (e.g., 25 imn in above case). 

Clement and Riviere [59] also reported that cellulose acetate or a mixed ester — a nitrate-acetate — can be obtained by reacting cellulose nitrate with acetic anhydride, acetic acid, and sulphuric acid. According to more recent contributions, e.g. Wolfrom, Bower and Maker [60], the reaction should be performed as follows Cellulose nitrate is dissolved in the cold in a little sulphuric add and acetic anhydride, the surplus of acetic anhydride is then hydrolysed also in the cold, and cellulose acetate is extracted with a suitable solvent, such as chloroform. Other methods of acetylating nitrocellulose consist in reduction, for instance with zinc and hydrogen chloride, which entails denitration of the ester, followed by acetylation with acetic anhydride. All these reactions are carried out in the same vessel. Further, it is possible to synthesize mixed esters, cellulose nitrate-acetates, by subjecting cellulose to the action of a mixture that includes nitric acid, acetic add and acetic anhydride in the presence of sulphuric acid (Kruger [61]). The use of a large amount of nitric acid favours the formation of nitrocellulose only. Mixed esters are formed... 

Note Polar solvent soluble in water, alcohols (organic halides), ether, and many oils flammable moderately toxic by inhalation and skin absorption incompatible with strong oxidizers, nitrates, strong alkalis, strong acids. Synonyms acedin, acetic ether, acetic ester, ethyl ethanoate, vinegar naphtha, acetic acid ethyl ester. 

Tables II to X give the melting points and, where applicable, the optical rotations of the inositols, inososes, inosamines, and quercitols, and of all of their known O-substituted derivatives. Anhydroinositols, although not substitution products in the strict sense, are included, as are the carbonyl-functional derivatives of the inososes. Halogen- and nitro-substituted cyclitols, and the C-methyl-inositols and their derivatives, are not included most of these compounds are referred to in the text. The derivatives are arranged in the following order salts (inosamines) or functional derivatives (inososes), carboxylic esters, borates, nitrates, sulfonic esters, phosphates, glycosides, acetals (and Schiff bases), ethers (and IV-alkyl derivatives), and anhydrides.

Esters from unsaturated fatty acid chlorides are usually viscous or limpid oils soluble in hydrocarbons and turpentine, and whose primary applications are as varnishes, films, artificial threads, aqueous emulsions, and rubber-like plastics.2067,2068 Heating them in an inert gas produced insoluble products formed by polymerization involving double bonds in the acyl moieites.2069 As mentioned in the section on nitrates, acetates of amylose are less compact than amylopectin acetate.1468 Esters of unsaturated acids have also been proposed as re-moistenable adhesives.1971 1972... 

ACETIC ESTER (141-78-6) Forms explosive mixture with air (flash point 135°F/57°C oc). Violent reaction with oxidizers, chlorosulfonic acid. Incompatible with strong acids, nitrates, lithium aluminum hydride, lithium tetrahydroaluminate, oleum. Will hydrolyze on standing, forming acetic acid and ethyl alcohol this reaction is greatly accelerated by strong bases. 

BUTYL ACETATE ESTER (110-19-0) Forms explosive mixture with air (flash point 63°F/17°C). Reacts with water slowly, forming acetic acid and isobutyl alcohol. Reacts violently with strong oxidizers. Incompatible with sulfuric acid, nitric acid, caustics, aliphatic amines, nitrates, isocyanates. Dissolves rubber, many plastics, resins, and some coatings. Flow or agitation of substance may generate electrostatic charges due to low conductivity. 

Picatinny Arsenal, Dover, N, J., Cellulose Nitrate-Acetate Mixed Esters, PA-TR-3105. 

Cellulose esters n. Any derivative of cellulose in which the free hydroxyl groups attached to the cellulose chain have been replaced wholly or in part by acidic groups, e.g., nitrate, acetate, propionate, butyrate, or stearate groups. Esterification is effected by the use of a mixture of an acid with its anhydride in the presence of a catalyst such as sulfuric acid. Mixed esters of cellulose, e.g., cellulose acetate butyrate, are prepared by using mixed acids and mixed anhydrides. 

Chemical structure of cellulose (or regenerated cellulose) is shown in Scheme 1. Other important families of cellulose polymers are the cellulose esters, with the presence of groups such as nitrate, acetate, methyl or ethyl. All these polymers, also called cellophanes, are very sensitive to thermal, chemical and also biological degradation, since cellulose is a polysaccharide. 

Front-side exchange (path (e)) partakes of the character of an add-base reaction in the nitrosoamide decomposition (section a (2) (e)), and in view of the basicity of the incipient hydroxide ion, one would expect extensive exchange of the counter ion in the nitrous add deamination (equation 146, path (e)). In fact, acetate esters are the chief products from deaminations in acetic add (ref. of Table 12), and the alcohol component of the reaction has only rarely been reported (Table 12). In acetic acid runs, the adds present in the medium (HX, equation 146) are HO2CCH3, HONO and HONO2 (the latter from the disproportionation of nitrous add). Acetate esters have invariably been reported as products in deamination and in a few instances nitrite and nitrate estershave been isolated. 

ETHYl, ACETATE CH.COOCjH, Acetic ester. AcHk ether. Ethyl enthoAoate Nitrates strong oxidizers, BialirT. and adds 24 2.2 11... 

METHYL ACETATE CHjCOOCHj Acetk acid, methyl ester Methyl acetic ester Methyl eihanoate Nitrates strong oxMizcrs, alkalies, and acids 14 3.1 16... 

Acetobutyrate is the most resistant among the cellulose esters (nitrate, acetate, and acetobutyrate) and thus is used most often. Acetobutyrate is resistant to water, naphtha, organic solvents, and salt solutions. Pipelines made from cellulose acetobutyrate are used for gas, water, naphtha and mineral oil CAB is not suitable for... 

With solutions of acetyl nitrate, olefins may be converted to acetate esters of / -nitro alochols produced from the olefins. 

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