Nitrate glycidyl

Since Glycidyl Nitrate is the monomer of PGN, its properties should be noted in Vol 6,... 

Glycidyl nitrate and NIMMO - batch reactor verses flow reactor ... 

Reaction optimization was achieved by varying flow rate, concentration and the reaction exotherm temperature. In this way glycidol nitration reactions were scaled-up from 0.85 moles up to 40.5 moles. In a single run 4.64 kg of glycidyl nitrate (99.8 % yield) of 99.9 % purity was produced. Similar optimization for HMMO nitration produced 5.5 kg of NIMMO (99.1 % yield) of 99.6 % purity in a single run. 

Jones, A.R. O Brien, R.W. (1980) Metabolism of three active analogues of the male antifertility agent a-chlorohydrin in the rat. Xenobiotica, 5, 365-370 Kaplan, D.L., Cornell, J.H. Kaplan, A.M. (1982) Biodegradation of glycidol and glycidyl nitrate. Appl. environ. Microbiol., 43, 144-150... 

Prepared from l-azido-3-chloro-2-propanol and aqueous sodium hydroxide as described for glycidyl nitrate. See W. L. Petty and P. L. Nichols, Jr., J. Amer. Chem. Soc. 76, 4385 (1954). 

Polyurethane energetic block copolymers, (VIII), consisting of toluene diisocyanate, 1,4-butanediol, and dihydroxyl poly(3-azidomethyl-3-methylox-etane) were prepared by Sanderson et al. (3) and used as binders in high-energy compositions, especially rocket propellants. Poly(glycidyl nitrate) urethanes were previously prepared by the authors and are discussed (4). 

Glycidyl nitrate (GlyN) is synthesized in a similar manner to NiMMO by selective -OH nitration of glycidol using N2Os. The yield and purity are both high. 

Structure (4.20) Poly(glycidyl nitrate) [Poly(GlyN)]... 

The U. S. Naval Ordnance Test Station and JPL studied the preparation and polymerization of glycidyl nitrate ... 

Sanderson [1] and Highsmith [2] prepared glycidyl nitrate and subsequently converted it into polyglycidyl nitrate (I) using calcium hydride and boron trifluoride. 

More recently Estrin and Entelis [26] have published a series of papers on the polymerization of ECH and glycidyl nitrate initiated by BF3 and BF3. Et2 0. They have attempted to explain the low molecular weight... 

Estrin and Entelis [26] report that the BF3 catalysed polymerizations of ECH and glycidyl nitrate both show rapid slowing down of polymerization after 20—40% conversion. Kinetics measured at —40 to —70°C were complex. Initial rates had an order of 1.8 with respect to monomer and were first order with respect to BF3. Initiation was slow and chain transfer determined the molecular weight of the products. Activation energies determined were approximately 6 kcalmole for each monomer. 

Thus, 50g of I(R=0CH2CH20, m = 2 n = l), prepd by adding (CH20H)2 to glycidyl nitrate, 0.5g EtgN, and 30g tolylene diisocyanate were mixed and allowed to stand at RT for 4—12 hrs to give a brown elastic, inflammable resin which was useful as a component of expl compns]... 

Photodissociation dynamics of alkyl nitrites adsorbed on Mgp2 surfaces and on the Ag(lll) surface have been studied. The laser photodissociation and thermal pyrolysis of poly(glycidyl nitrate) have been investigated. Such high-energy polymers have been proposed for use as binders in solid rocket motors. 

Epichlorohydrin or chloromethyloxirane is manufactured from allyl chloride, and, in 2006, had a merchant price of US 1.66 kg [4]. It is used as a building block in the manufacture of plastics, epoxy resins, phenoxy resins, and other polymers, and as a solvent for cellulose, resins, and paints, and has also found use as an insect fumigant. Epoxy resins (aryl glycidyl ethers) are manufactured successfully in large scale (1.2 x 10 metric tons in 2000) [26] and are widely used in a variety of industrial and commercial applications [27]. These are made by addition reactions of epichlorohydrins or by epoxidation of allyl ethers or esters (Table 1.1). Epichlorohydrin can be reacted with an alkali nitrate to produce glycidyl nitrate, an energetic binder used in explosive and propellant compositions. 

---