Societe Nationale Des Poudres Et Explosifs

Marc D Piteau

Jean-Pierre G Senet

Thierry A Malfroot

Roy A Olofson

Michel Burgard

Jonathan T Martz

Alain J Rollat

Guy C Cagnon

Serge L Lecolier

Patrick Wolf

Vu A Dang

Annick G Coqueugniot

Genevieve Eck

Robert J Bruggeman

The invention relates to a new process for the synthesis of 2,4,6,8-tetranitro-2,4,6,8-tetraazabicyclo-[3.3.0]octane (bicyclo-HMX) by reaction of nitronium tetrafluoroborate with 2,4,6,8-tetraacetyl-2,4,6,8-tetraazabicyclo[3.3.0]octane in the presence of fluoride ions. The process makes it possible to obtain pure bicyclo-HMX in an acceptable yield. Bicyclo-HMX is an explosive which can be employed as explosive or propellent charge in solid pyrotechnic compositions.

Process for the synthesis of 2,4,6,8-tetranitro-2,4,6,8-tetraazabicyclo

The invention relates to a process for the preparation of 1-bromoethyl hydrocarbonyl carbonates, characterized in that anhydrous hydrobromic acid is reacted with a vinyl hydrocarbonyl carbonate of formula ##STR1## in which R denotes a saturated, substituted or unsubstituted C.sub.1 -C.sub.12 aliphatic radical or C.sub.5 -C.sub.24 alicyclic radical, or a substituted or unsubstituted aromatic radical, at a temperature between 10.degree. and 100.degree. C. The invention also relates to the new 1-bromoethyl hydrocarbonyl carbonates of formula: ##STR2## These carbonates are particularly sought after for introducing a carbonate group into a molecule.

Process for the preparation of 1-bromoethyl hydrocarbonyl carbonates and

A process for the preparation of fluoroformates of formula: ##STR1## in which R.sup.1 is a substituted or unsubstituted, saturated or unsaturated aliphatic, cycloaliphatic or polycyclic radical, or substituted or unsubstituted araliphatic radical or an aromatic radical, which consists of reacting a carbonate of formula: ##STR2## in which R.sup.1 has the same meaning as hereinabove and R.sup.2 is hydrogen, alkyl of 1-12 carbon atoms, cycloalkyl of 5-12 carbon atoms, saturated or unsaturated, unsubstituted or substituted by one or more halogen atoms or R.sup.2 is aryl, unsubstituted or substituted by one or more halogen atoms, with an alkali or alkaline earth fluoride, ammonium fluoride or a quaternary ammonium fluoride, of formula FNR.sup.3 R.sup.4 R.sup.5 R.sup.6, wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6 are the same or different and are hydrogen, alkyl or aralkyl of 1-12 carbon atoms or a fluoride which is KHF.sub.2, NH.sub.4 HF.sub.2 or KSO.sub.2 F. The fluoride is activated by a complexing agent for the cation which is a cryptate, a cyclic or linear polyether or by means of a polar aprotic compound. The carbonate is split to give a reaction mixture containing an aldehyde and the fluoroformate which is removed from the reaction mixture.

Process for the preparation of fluoroformates

Process for the synthesis of .alpha.-chlorinated chloroformates, and new .alpha.-chlorinated chloroformates. The invention relates to a new process for the manufacture of .alpha.-chlorinated chloroformates and, to new .alpha.-chlorinated chloroformates as new industrial products. The process according to the invention consists of a synthesis, by catalytic phosgenation, of .alpha.-chlorinated chloroformates of the formula: ##STR1## in which: R represents a substituted or unsubstituted hydrocarbon radical and m represents an integer superior or equal to one, this synthesis consisting in reacting phosgene with the aldehyde R--CHO).sub.m, in the presence of a catalyst which is an organic or inorganic substance which is capable in a medium containing an aldehyde of the formula R--CHO).sub.m, phosgene and, possibly, a solvent, of generating a pair of ions one of which is an halogenide anion and the other is a cation which is sufficiently separated from said halogenide anion so as to give to the latter a nucleophilic power enabling it to react with the function(s) aldehyde of the molecule R--CHO).sub.m.

Process for the synthesis of .alpha.-chlorinated chloroformates

Process for the synthesis of .alpha.-chlorinated chloroformates, and new .alpha.-chlorinated chloroformates. The invention relates to a new process for the manufacture of .alpha.-chlorinated chloroformates and, to new .alpha.-chlorinated chloroformates as new industrial products.

Process for the synthesis of alpha-chlorinated chloroformates

The invention relates to new industrial products of the general formula ##STR1## a process for the manufacture of these products and their application as extraction agents in hydrometallurgy.

Extraction of metals from aqueous solutions with cyclic organic

The invention relates to new industrial products of the general formula ##STR1## a process for the manufacture of these products and their application in hydrometallurgy. According to the invention, R is in particular an alkyl, cycloalkyl, aryl, aralkyl, carboxylate, polyoxyethylene, polyester or polycarbonate group. The process consists in reacting an alcohol or a polyol, ROH, with 2,3-dioxycarbonylpropyl chloroformate, at between -10.degree. and +20.degree. C., in the presence of an acid acceptor. Application: the compounds according to the invention are extraction agents for hydrometallurgy, which can be used in dilute solution.

Carbonates carrying cyclic carbonate groups

The invention relates, by way of new products, to poly-(carbonate-urethanes) with acrylic or methacrylic acid terminal groups, of the formula ##STR1## in which X represents either hydrogen or the methyl group, R represents a substituted or unsubstituted alkylene, cycloalkylene or arylene radical, R' represents a lower alkylene radical, Z represents a polycarbonate chain and C, H, N and O respectively represent carbon, hydrogen, nitrogen and oxygen. The unsaturated poly-(carbonate-urethanes) according to the invention are obtained by condensing a diisocyanate with a polycarbonate-diol and a lower hydroxyalkyl acrylate or methacrylate. They constitute a base for photocrosslinkable compositions which resist hydrolysis and possess a good adhesion.

Unsaturated poly-(carbonate-urethanes) and their applications to

The invention relates to a process for the preparation of halogeno-mercuri-aldehydes and -ketones. According to the invention, an alkenyl ester is reacted with a mercuric halide in the presence of water and, preferably, of an acid acceptor. The reaction, which is preferably carried out at between 15.degree. and 35.degree. C., makes it possible to obtain very pure products with excellent yields, especially when mercuric oxide is used as the acid acceptor.

Process for the preparation of halogeno-mercuri-aldehydes and -ketones

The invention relates to a process for the industrial scale synthesis of vinyl and isopropenyl chloroformates and thiochloroformates. According to the invention, phosgene or thiophosgene is reacted, at between 20.degree. and 70.degree. C., with a mercury salt XHg(CH.sub.2 CRO), in which X=Cl or --CH.sub.2 CRO, where R=H or CH.sub.3, in the presence of a solvent or a mixture of solvents having a dielectric constant greater than 10. The process can also be carried out using a mixture of the above solvents with a solvent which is not effective by itself (solvent of low polarity) but which is inexpensive. The yields achieved can exceed 90%.

Process for the industrial synthesis of vinyl and isopropenyl

A process for the preparation of chloroformates having terminal acrylic or methacrylic groups, comprises reacting at least one hydroxyalkyl acrylate or methacrylate with phosgene by introducing a solution of the acrylate or methacrylate into a solution of phosgene, while stirring, at a temperature of -25.degree. C to +5.degree. C, in the presence of an acid acceptor and a stoichiometric excess of phosgene.

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Itteville, France

Marc D Piteau