Produits Chimiques Ugine Kuhlmann

Other

Francis Weiss

Jean-Pierre Schirmann

Henri Mathais

Pierre Tellier

Serge Y Delavarenne

Jean P Schirmann

Andre Bader

This invention relates to a method for preparing oxaziridines which comprises reacting hydrogen peroxide with an azomethinic derivative or with a mixture of a carbonyl compound and a primary amine in the presence of catalytic amounts of selenium or of oxygenated compounds of selenium.

Process for the preparation of oxaziridine

New compounds comprising trioxa-1, 5, 7 spiro [2.5] octanes and bis(trioxa-1, 5, 7 spiro [2.5] octanes) and the process of preparing the compounds by reacting methylene-5 dioxanes-1, 3 and bis(methylene-5 dioxanes-1,3) respectively, with an epoxidation agent such as an organic peracid which can be used, for example, as non-reactive or reactive solvents for epoxy resin, in the preparation of thermosetting resins and for stabilizing polyvinylchloride.

Trioxa-1, 5, 7 spiro [2,5] octanes and their method of preparation

This invention relates to a method for preparing hydrazodicarbonamide ##STR1## which comprises reacting urea, sulfuric acid, water and an azine or a solution containing an azine of the formula ##STR2## wherein R.sub.1 is hydrogen and R.sub.2 or R.sub.1 and R.sub.2 each is a straight or branched alkyl radical or cycloalkyl radical of up to 6 carbon atoms or R.sub.1 and R.sub.2 of both the &gt;C=N-- moieties together form a straight or branched chain alkylene radical of from 3 to 5 carbon atoms and recovering the hydrazodicarbonamide from the reaction medium.

Method for manufacturing hydrazodicarbonamide

This invention relates to a method for preparing hydrazo-bis-acetonitriles of the general formula: ##EQU1## wherein R.sub.1 and R.sub.2 have the same meaning hereinafter given, which comprises:

Method for preparing hydrazo-bis-acetonitriles

This invention relates to a method for preparing an azine of the formula ##EQU1## wherein R.sub.1 and R.sub.2, which may be the same or different, represent a hydrogen atom or a straight alkyl radical of from 1 to 12 carbon atoms, a branched alkyl or cycloalkyl radical of 3 to 12 carbon atoms, or a hydrocarbon radical of from 6 to 12 carbon atoms containing a benzene, naphthalene, or pyridine aromatic ring or R.sub.1 and R.sub.2 together form a straight or branched alkylene radical of 3 to 11 carbon atoms, one of which may be replaced by an oxygen atom, all of the above being unsubstituted or substituted with chlorine, bromine, or fluorine atoms, or ethylene, nitro, hydroxy, alkoxy, carboxylic or percarboxylic acid, amide, nitrile, or carboxylic ester groups, or a mixture of an azine of formula (I) and a hydrazone of the formula ##EQU2## wherein R.sub.1 and R.sub.2 are as defined above and R.sub.3 and R.sub.4, which may be the same or different, represent a straight alkyl radical of from 1 to 12 carbon atoms, a branched alkyl or cycloalkyl radical of 3 to 12 carbon atoms, or a hydrocarbon radical of from 6 to 12 carbon atoms containing a benzene, naphthalene, or pyridine aromatic ring or R.sub.1 and R.sub.2 together form a straight or branched alkylene radical of 3 to 11 carbon atoms, one of which may be replaced by an oxygen atom, all of the above being unsubstituted or substituted by chlorine, bromine, fluorine, or iodine atoms, or hydroxy, ether oxide, carboxylic acid, carboxylic ester, nitrile, nitro, or sulphonic acid or amide groups or one of the two radicals R.sub.3 and R.sub.4 can represent a hydrogen atom, which comprises reacting hydrogen peroxide with ammonia or with a mixture of ammonia and primary or secondary amine of the formula ##EQU3## wherein R.sub.3 and R.sub.4 are as defined above, in the presence of a carbonyl compound of the formula ##EQU4## wherein R.sub.1 and R.sub.2 are as defined above, and a catalyst containing selenium.

Process for the preparation of hydrazine compounds

The invention relates to a method for preparing symmetrical ketazines of the formula ##EQU1## and unsymmetrical ketazines of the formula ##EQU2## and mixtures of ketazines (I), (II) and (IV) and (I), (III) and (V) wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each is a straight chain alkyl radical of from 1 to 12 carbon atoms, a branched chain alkyl radical or cycloalkyl radical of from 3 to 12 carbon atoms, or a phenyl radical, the aforesaid radicals being unsubstituted or substituted with radicals which are stable in the medium in which the ketazines are prepared; and in which case R.sup.1 and R.sup.2 can be the same or different radicals, and R.sup.3 and R.sup.4 are radicals different from each other and are each a radical different from R.sup.1 and R.sup.2 ; or R.sup.1 and R.sup.2, or R.sup.1 and R.sup.3, or R.sup.3 and R.sup.4 of either or both the ##EQU3## moieties together form a cyclic or substituted cyclic radical of from 3 to 11 carbon atoms in the ring, which comprises:

Method for preparing symmetrical and unsymmetrical ketazines and

A process is disclosed for the preparation of symmetrical azines of the formulas ##EQU1## and unsymmetrical azines of the formulas ##EQU2## and mixtures of azines (I), (II), and (IV), and (I), (III) and (V), wherein R.sup.1 , R.sup.2, R.sup.3 and R.sup.4 each is hydrogen, a straight-chain alkyl radical of from 1 to 12 carbon atoms, a branched-chain alkyl radical or a cycloalkyl radical of from 3 to 12 carbon atoms or a phenyl radical, the aforesaid radicals being unsubstituted or substituted with a radical which is stable in the medium in which said azines are produced; and in which case R.sup.1 and R.sup.2 can be the same or different radicals, R.sup.3 is a radical different from R.sup.1 and R.sup.2, R.sup.3 and R.sup. 4 are radicals different from each other, and each are different radicals from R.sup.1 and R.sup.2 ; or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, or R.sup. 3 and R.sup.4 of either or both the &gt;C=N-- moieties together form a cyclic or substituted cyclic radicals of from 3 to 11 carbon atoms in the ring.

Process for the preparation of symmetrical and unsymmetrical azines and

A method is disclosed for preparing symmetrical azines of the formulas ##EQU1## and unsymmetrical azines of the formulas ##EQU2## and mixtures of azines (I), (II) and (IV) and (I), (III) and (V), wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each is a hydrogen atom, a straight chain alkyl radical of from 1 to 12 carbon atoms, a branched chain alkyl radical or unsubstituted or alkyl substituted cycloalkyl radical of from 3 to 12 carbon atoms, a hydrocarbon radical of from 6 to 12 carbon atoms containing a benzene ring; further provided that R.sup.1 and R.sup.2 can be the same or different radicals, R.sup.3 is a radical different from R.sup.1 and R.sup.2 and R.sup.3 and R.sup.4 are radicals different from each other and each are different from R.sup.1 and R.sup.2 ; or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3 or R.sup.3 and R.sup.4 bonded to the same carbon atom together form an unsubstituted or aliphatic substituted alkylene radical of from 3 to 11 carbon atoms, each of the aforesaid radicals being unsubstituted or substituted with one or more radicals which are stable in the medium in which the azines are produced. The method comprises reacting in the liquid phase, ammonia with a percarboxylic acid of the formula ##EQU3## wherein R.sup.5 represents a hydrogen atom, a straight chain alkyl radical of from 1 to 18 carbon atoms, a branched chain alkyl radical or unsubstituted or alkyl substituted cycloalkyl radical of from 3 to 12 carbon atoms, a hydrocarbon radical of from 6 to 12 carbon atoms containing a benzene ring, further provided that the aforesaid radicals can contain a non-epoxidizable or epoxidizable ethylenic double bond and/or one or more radicals which are stable in the medium in which the azines are produced, in the presence of a carbonyl compound of the formula ##EQU4## alone or together with a different carbonyl compound ##EQU5## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each have the same meaning defined above and recovering the azine or mixture of azines from the reaction medium.

Method for preparing azines

A method is disclosed for preparing symmetrical azines of the formulas ##EQU1## and unsymmetrical azines of the formulas ##EQU2## and mixtures of azines (I), (II) and (IV) and (I), (III) and (V), wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each is a hydrogen atom, a straight chain alkyl radical of from 1 to 12 carbon atoms, a branched chain alkyl radical or unsubstituted or alkyl substituted cycloalkyl radical of from 3 to 12 carbon atoms, a hydrocarbon radical of from 6 to 12 carbon atoms containing an aromatic nucleus; further provided that R.sup.1 and R.sup.2 can be the same or different radicals, and R.sup.3 and R.sup.4 are the same or different radicals and each are different from R.sup.1 and R.sup.2 ; or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3 or R.sup.3 and R.sup.4 bonded to the same carbon atom together form an unsubstituted or aliphatic substituted alkylene radical of from 3 to 11 carbon atoms, each of the aforesaid radicals being unsubstituted or substituted with one or more radicals which are stable in the medium in which the azines are produced. The method comprises reacting ammonia and a carbonyl compound of the formula ##EQU3## alone or together with a different carbonyl compound ##EQU4## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each have the same meaning defined above with hydrogen peroxide in the presence of a carboxylic ester to provide the azine or mixture of azines.

An oxirane compound is prepared by reacting an olefinically unsaturated compound with hydrogen peroxide in the presence both of (i) at least one lead compound, exemplarily triethyl lead hydroxide and also of (ii) at least one compound of a group IV-A, V-A or VI-A transition metal exemplarily tungsten hexacarbonyl. The epoxided products are useful in the manufacture of plastics, adhesives and the like.

Epoxidation of olefins by hydrogen peroxide

A method is disclosed for preparing symmetrical azines of the formulas ##EQU1## and unsymmetrical azines of the formulas ##EQU2## and mixtures of azines (I), (II) and (IV) and (I), (III) and (V), wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each is a hydrogen atom, a straight chain alkyl radical of from 1 to 12 carbon atoms, a branched chain alkyl radical or unsubstituted or alkyl substituted cycloalkyl radical of from 3 to 12 carbon atoms, a hydrocarbon radical of from 6 to 12 carbon atoms containing a benzene ring; further provided that R.sup.1 and R.sup.2 can be the same or different radicals, R.sup.3 is a radical different from R.sup.1 and R.sup.2 and R.sup.3 and R.sup.4 are radicals different from each other and each are different from R.sup.1 and R.sup.2 ; or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3 or R.sup.3 and R.sup.4 bonded to the same carbon atom together form an unsubstituted or aliphatic substituted alkylene radical of from 3 to 11 carbon atoms, each of the aforesaid radicals being unsubstituted or substituted with one or more radicals which are stable in the medium in which the azines are produced. The method comprises reacting ammonia and a carbonyl compound of the formula ##EQU3## alone or together with a different carbonyl compound ##EQU4## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each have the same meaning defined above with at least one diacyl peroxide (acyl peroxide) which are compounds having one or several groups of the structure ##EQU5## and recovering the azine or mixture of azines from the reaction medium.

A method is disclosed for preparing symmetrical azines of the formulas ##EQU1## and unsymmetrical azines of the formulas ##EQU2## and mixtures of azines (I), (II) and (IV) and (I), (III) and (V), wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each is a hydrogen atom, a straight chain alkyl radical of from 1 to 12 carbon atoms, a branched chain alkyl radical or unsubstituted or alkyl substituted cycloalkyl radical of from 3 to 12 carbon atoms, a hydrocarbon radical of from 6 to 12 carbon atoms containing a benzene ring; further provided that R.sup.1 and R.sup.2 can be the same or different radicals, R.sup.3 is a radical different from R.sup.1 and R.sup.2 and R.sup.3 and R.sup.4 are radicals different from each other and each is different from R.sup.1 and R.sup.2 ; or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3 or R.sup.3 and R.sup.4 bonded to the same carbon atom together form an unsubstituted or alkyl substituted alkylene radical of from 3 to 11 carbon atoms, each of the aforesaid radicals being unsubstituted or substituted with one or more radicals which are stable in the medium in which said azines are produced. The method involves reacting in the liquid phase and in the absence of a nitrile, a carbonyl compound of the formula ##EQU3## alone or together with a different carbonyl compound ##EQU4## or ##EQU5## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each has the same meaning defined above, with ammonia and hydrogen peroxide in the presence of an effective amount of at least one catalyst selected from the group consisting of the hydroxides and water soluble organic and inorganic salts of ammonium and the metals of Groups 1a and IIa of the Periodic Table of the Elements, and recovering the azine or mixture of azines from the reaction medium.

Enolic monoether and diether of adipic dialdehyde such as 6-methoxy-5-hexene-1-al, 1,6-dimethoxy-1,5-hexadiene, 1,6-bis-(2 hydroxy propoxy)-1,5-hexadiene are prepared by heating to a sufficiently high temperature for a Cope rearrangement, e.g., 150.degree. to 450.degree. C. of the corresponding monoether or diether of 1,5-hexadiene-3,4-diol.

Enolic ethers of adipic dialdehyde and method for preparing the same

A method is disclosed for preparing symmetrical azines of the formulas ##EQU1## and unsymmetrical azines of the formulas ##EQU2## and mixtures of azines (I), (II) and (IV) and (I), (III) and (V) wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each is a hydrogen atom, a straight chain alkyl radical of from 1 to 12 carbon atoms, a branched chain alkyl radical or unsubstituted or alkyl substituted cycloalkyl radical of from 3 to 12 carbon atoms, a hydrocarbon radical of from 6 to 12 carbon atoms containing an aromatic nucleus; further provided that R.sup.1 and R.sup.2 can be the same or different radicals, and R.sup.3 and R.sup.4 are the same or different radicals and each are different from R.sup.1 and R.sup.2 ; or R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3 or R.sup.3 and R.sup.4 bonded to the same carbon atom together form an unsubstituted or aliphatic substituted alkylene radical of from 3 to 11 carbon atoms, each of the aforesaid radicals being unsubstituted or substituted with one or more radicals which are stable in the medium in which the azines are produced. The method comprises reacting ammonia, hydrogen peroxide and a carbonyl compound of the formula ##EQU3## alone or together with a different carbonyl compound ##EQU4## or ##EQU5## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each have the same meaning defined above in the presence of an amide or an imide of a carboxylic acid having an ionization constant greater than 5 .times. 10.sup..sup.-5 or of a di-, tri- or tetra-carboxylic acid of which at least one of the carboxylic acid functions has an ionization constant greater than 5 .times. 10.sup..sup.-5 (corresponding to a pK less than about 4.3) to produce the azine or mixture of azines.

This invention relates to a method of preparing hydrazones of the formula ##EQU1## in which R.sub.1 and R.sub.2, which may be identical or different, represent a linear alkyl radical of from 1 to 12 carbon atoms, a branched alkyl or cycloalkyl radical of from 3 to 12 carbon atoms, an aromatic radical of from 6 to 12 carbon atoms having a benzene or naphthalene nucleus, or a radical of from 5 to 12 carbon atoms having a pyridine nucleus, or R.sub.1 and R.sub.2 together form a linear or branched alkylene radical of from 3 to 12 carbon atoms in which one of the carbon atoms of the chain may be replaced by an oxygen atom, all of the above radicals being unsubstituted or substituted by one or more atoms or groups such as chlorine, bromine, fluorine, or iodine atoms or hydroxy, ether, carboxylic acid, carboxylic amide or ester, nitrile, nitro, or sulphonic acid or amide groups, or one of the two radicals R.sub.1 and R.sub.2 may be a hydrogen atom, and in which R.sub.3 and R.sub.4, which may be identical or different, represent a hydrogen atom, a linear alkyl or cycloalkyl radical of from 3 to 12 carbon atoms, in which one of the carbon atoms of the cycloalkyl radical may be replaced by an oxygen atom, or an aromatic hydrocarbon radical of from 6 to 12 carbon atoms or R.sub.3 and R.sub.4 together represent a linear or branched alkylene radical of from 3 to 11 carbon atoms, the above radicals being unsubstituted or substituted by atoms or groups such as chlorine, bromine, fluorine, ethylenic groups, nitro, hydroxy, alkoxy, or carboxylic acid or ester radicals , which comprises reacting a primary or secondary amine of the formula Wherein R.sub.1 and R.sub.2 are as defined above, ammonia, and a carbonyl compound of the formula Wherein R.sub.3 and R.sub.4 are as defined above, with a peroxide compound.

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Pierre Benite, France

Francis Weiss