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1. 发明授权

US5252309A Azine synthesis in the absence of CO.sub.2 失效
标题翻译：在不存在二氧化碳的情况下合成Azine
公开(公告)号：US5252309A
公开(公告)日：1993-10-12
申请号：US897830
申请日：1992-06-12
申请人： Gerard Krempf , Bertrand Collier , Pierre Tellier , Jean-Pierre Schirmann
发明人： Gerard Krempf , Bertrand Collier , Pierre Tellier , Jean-Pierre Schirmann
IPC分类号： C07B61/00 , C07C249/00 , C07C249/16 , C07C251/88 , C01B21/16 , C07C241/00 , C07C241/02
CPC分类号： C07C249/00 , Y02P20/582
摘要： Azines, well suited for hydrolysis into hydrazine, are prepared in high yields by reacting ammonia, aqueous hydrogen peroxide and a carbonyl compound reactant in the presence of a catalytically effective amount of a catalyst medium therefor, i.e., an aqueous solution of ammonium acetate and acetamide or of acetamide and acetic acid, but in the absence of CO.sub.2.
摘要翻译：通过在催化有效量的催化剂介质，即乙酸铵和乙酰胺的水溶液存在下，使氨，过氧化氢水溶液和羰基化合物反应物反应，以高产率制备非常适合水解成肼的氮杂环丁烷或乙酰胺和乙酸，但在不存在CO 2的情况下。

2. 发明授权

US5393508A Vaporization of solutions of hydrazine hydrate 失效
标题翻译：水合肼溶液的蒸发
公开(公告)号：US5393508A
公开(公告)日：1995-02-28
申请号：US118775
申请日：1993-09-10
申请人： Gerard Krempf , Bertrand Collier , Pierre Tellier , Jean-Pierre Pleuvry
发明人： Gerard Krempf , Bertrand Collier , Pierre Tellier , Jean-Pierre Pleuvry
IPC分类号： C01B21/16 , F28F21/08
CPC分类号： F28F21/082 , C01B21/16 , Y10S203/06
摘要： Solutions of hydrazine hydrate are vaporized, without any concomitant decomposition thereof, by heating such solutions, in the liquid phase, under conditions as to effect the decompression or volatilization thereof; this process is particularly applicable for the vaporization of that hydrazine hydrate solution contained in the reboiler of a column wherein the hydrolysis of an azine R.sub.1 R.sub.2 C.dbd.N-N.dbd.CR.sub.1 R.sub.2 is carried out, with recovery of hydrazine hydrate at the base of the column and of a ketone, R.sub.1 R.sub.2 C.dbd.O, at the column head.
摘要翻译：通过在液相中加热这些溶液，在其减压或挥发的条件下，将水合肼溶液蒸发而不伴随其分解; 该方法特别适用于在塔的再沸器中蒸发含水合肼的水合物溶液，其中进行吖嗪R1R2C = NN = CR1R2is的水解，同时回收塔底部的水合肼和酮， R1R2C = O，在柱头。

3. 发明授权

US3943132A Process for the preparation of hydrazones 失效
标题翻译：制备腙的方法
公开(公告)号：US3943132A
公开(公告)日：1976-03-09
申请号：US406467
申请日：1973-10-15
申请人： Jean-Pierre Schirmann , Henri Mathais , Pierre Tellier , Francis Weiss
发明人： Jean-Pierre Schirmann , Henri Mathais , Pierre Tellier , Francis Weiss
IPC分类号： C07D213/77 , C07B43/00 , C07C20060101 , C07C67/00 , C07C241/00 , C07C251/76 , C07C251/82 , C07C251/84 , C07C251/86 , C07D20060101 , C07C109/14 , C07C109/16 , C07C109/18
CPC分类号： C07C249/16 , C07C251/76 , C07C251/84
摘要： 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 formulaWherein R.sub.1 and R.sub.2 are as defined above, ammonia, and a carbonyl compound of the formulaWherein R.sub.3 and R.sub.4 are as defined above, with a peroxide compound.
摘要翻译：本发明涉及制备式R 1 R 3 ANGLE NN = C ANGLE（I）R 2 R 4的腙的方法，其中可以相同或不同的R 1和R 2表示1至12个碳原子的直链烷基，支链具有3至12个碳原子的烷基或环烷基，具有苯或萘核的6至12个碳原子的芳族基团或具有吡啶核的5至12个碳原子的基团，或者R 1和R 2一起形成具有3至12个碳原子的直链或支链亚烷基，其中链中的一个碳原子可以被氧原子代替，所有上述基团都是未取代的或被一个或多个原子或基团取代，例如氯，溴，氟或碘原子或羟基，醚，羧酸，羧酰胺或酯，腈，硝基或磺酸或酰胺基，或两个基团R 1和R 2之一可以是氢原子，其中 R3和R4可以相同或相同不同的是氢原子，具有3-12个碳原子的直链烷基或环烷基，其中环烷基的一个碳原子可以被氧原子取代，或6-12的芳族烃基碳原子或R3和R4一起表示具有3至11个碳原子的直链或支链亚烷基，上述基团是未取代的或被诸如氯，溴，氟，烯基，硝基，羟基，烷氧基，或羧酸或酯基，其包括使式WHEREIN R 1和R 2如上所定义的伯胺或仲胺与氨过氧化合物与式WHEREIN R 3和R 4如上定义的羰基化合物反应。

4. 发明授权

US5239119A Catalytic synthesis of azines from H.sub.2 O.sub.2 /NH.sub.3 /carbonyl compounds 失效
标题翻译：来自H 2 O 2 / NH 3 /碳化合物的AZINES的催化合成
公开(公告)号：US5239119A
公开(公告)日：1993-08-24
申请号：US797356
申请日：1991-11-25
申请人： Jean-Pierre Schirmann , Pierre Tellier
发明人： Jean-Pierre Schirmann , Pierre Tellier
IPC分类号： B01J31/04 , C07B61/00 , C07C249/16 , C07C251/08 , C07C251/88
CPC分类号： C07C249/16
摘要： Azines are synthesized from aqueous hydrogen peroxide, ammonia and a carbonyl compound, e.g., acetone, methyl ethyl ketone or methyl isobutyl ketone, in the presence of a catalytically effective amount of immixture of an amide of a weak acid and an ammonium salt corresponding to such weak acid. A more general high output such process comprises (a) interreacting aqueous hydrogen peroxide, ammonia and a carbonyl compound in the presence of a catalytically effective amount of immixture comprising an amide of a weak acid, (b) separating the azine thus produced from the medium of reaction, (c) reconstituting the amount of the amide in the medium of reaction to the initial amount thereof present at the onset of step (a), and (d) recycling such reconstituted medium of reaction to step (a).
摘要翻译：在催化有效量的弱酸和对应于此的铵盐的酰胺的混合物的存在下，由过氧化氢水，氨和羰基化合物（例如丙酮，甲基乙基酮或甲基异丁基酮）合成氮杂弱酸。更一般的高产量，这种方法包括（a）在催化有效量的包含弱酸酰胺的混合物存在下，使过氧化氢，氨和羰基化合物反应，（b）将由此产生的吖嗪与介质分离的反应，（c）将反应介质中的酰胺量与步骤（a）开始时的初始量重构，和（d）将这种重新配制的反应介质再循环到步骤（a）。

5. 发明授权

US3959262A Method for preparing azines 失效
标题翻译：制备吖嗪的方法
公开(公告)号：US3959262A
公开(公告)日：1976-05-25
申请号：US290507
申请日：1972-09-20
申请人： Henri Mathais , Jean-Pierre Schirmann , Pierre Tellier , Francis Weiss
发明人： Henri Mathais , Jean-Pierre Schirmann , Pierre Tellier , Francis Weiss
IPC分类号： C07C251/88 , C07C20060101 , C07C67/00 , C07C241/00 , C07C119/00
CPC分类号： C07C251/88
摘要： 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.
摘要翻译：公开了一种用于制备式R1R1的对称吖嗪的方法。方法C = NN = C ANGLE（I）R2R2 R1R1角度C = NN = C角度（II）R3R3 R3R3角度C = NN = C角度（III）R4R4和不对称吖嗪式（I），（II）和（IV）和（I），（III）的混合物，其中R 1，R 2，R 3，R 3，R 3，和（V），其中R 1，R 2，R 3和R 4各自为氢原子，具有1至12个碳原子的直链烷基，支链烷基或未取代的或烷基取代的3至12个碳原子的环烷基原子，含有苯环的6-12个碳原子的烃基; 进一步提供R1和R2可以相同或不同的基团，R3是不同于R1和R2的基团，R3和R4是彼此不同的基团，并且各自不同于R1和R2; 或者R 1和R 2或R 1，R 3或R 3或R 4和R 4与R 4相同的碳原子一起形成未取代的或脂族取代的3-11个碳原子的亚烷基，上述每个基团是未取代的或被一个或多个基团取代，在其中产生吖嗪的培养基中是稳定的。

6. 发明授权

US3951964A Method for preparing azines 失效
公开(公告)号：US3951964A
公开(公告)日：1976-04-20
申请号：US308836
申请日：1972-11-22
申请人： Pierre Tellier , Henri Mathais , Jean-Pierre Schirmann , Francis Weiss
发明人： Pierre Tellier , Henri Mathais , Jean-Pierre Schirmann , Francis Weiss
IPC分类号： C07C251/88 , C07C20060101 , C07C67/00 , C07C241/00 , C07C119/00
CPC分类号： C07C251/88
摘要： 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.

7. 发明授权

US3943152A Method for preparing azines 失效
标题翻译：制备吖嗪的方法
公开(公告)号：US3943152A
公开(公告)日：1976-03-09
申请号：US341057
申请日：1973-03-14
申请人： Pierre Tellier , Jean-Pierre Schirmann , Henri Mathais , Francis Weiss
发明人： Pierre Tellier , Jean-Pierre Schirmann , Henri Mathais , Francis Weiss
IPC分类号： C07C251/88 , C07C20060101 , C07C67/00 , C07C241/00 , C07C109/14 , C07C109/16
CPC分类号： C07C251/88
摘要： 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.
摘要翻译：公开了一种用于制备式R1R1的对称吖嗪的方法。方法C = NN = C ANGLE（I）R2R2 R1R1角度C = NN = C角度（II）R3R3 R3R3角度C = NN = C角度（III）R4R4和不对称吖嗪式（I），（II）和（IV）和（I），（III）的混合物，其中R 1，R 2，R 3，R 3，R 3，和（V）其中R 1，R 2，R 3和R 4各自为氢原子，具有1至12个碳原子的直链烷基，支链烷基或未取代或具有3至12个碳原子的烷基取代的环烷基含有6至12个碳原子的烃基含有芳香核; 进一步提供R1和R2可以相同或不同的基团，并且R3和R4是相同或不同的基团，并且各自不同于R1和R2; 或者R 1和R 2或R 1，R 3或R 3或R 4和R 4与R 4相同的碳原子一起形成未取代的或脂族取代的3-11个碳原子的亚烷基，上述每个基团是未取代的或被一个或多个基团取代，在其中产生吖嗪的培养基中是稳定的。

8. 发明授权

US06605265B1 Continuous production of azines/hydrazine hydrate 失效
标题翻译：连续生产吖嗪/水合肼
公开(公告)号：US06605265B1
公开(公告)日：2003-08-12
申请号：US08217752
申请日：1994-03-25
申请人： Jean-Pierre Schirmann , Jean-Pierre Pleuvry , Pierre Tellier
发明人： Jean-Pierre Schirmann , Jean-Pierre Pleuvry , Pierre Tellier
IPC分类号： C01B2116
CPC分类号： C01B21/16 , C07C249/00 , C07C251/88 , Y02P20/582
摘要： Azines, e.g., ketazines, are continuously produced by (i) establishing a loop having an azine reaction medium circulating therein, such loop including an azine reaction zone, means for separating azine final product from the circulating reaction medium, means for heating the reaction medium and for purging water therefrom, and means for recycling heated and purged reaction medium to the azine reaction zone, (ii) introducing hydrogen peroxide, ammonia and a carbonyl compound into the circulating reaction medium in the azine reaction zone, (iii) withdrawing azine final product thus formed from the circulating reaction medium. downstream of the azine reaction zone, (iii) thereafter purging water from the circulating reaction medium to maintain the volume thereof essentially constant, (iv) heating the circulating reaction medium to a temperature of at least 130° C., (v) recycling thus heated reaction medium to the azine reaction zone, and (vi), at any point along the loop, introducing a reagent into the circulating reaction medium as to essentially maintain the equilibrium of the azine-forming reaction; the final product azines are conveniently hydrolyzed into hydrazine hydrate.
摘要翻译：通过（i）建立其中循环其中的吖嗪反应介质的环，包括吖嗪反应区的环路，用于从循环反应介质中分离吖嗪最终产物的装置，连续制备氮杂环丁烷，例如加入反应介质和用于从其中清洗水的装置，以及用于将加热和净化的反应介质再循环到吖嗪反应区的装置，（ii）在吖嗪反应区中将过氧化氢，氨和羰基化合物引入循环反应介质中，（iii）由循环反应介质形成的产物。（iii）然后从循环反应介质中清洗水以使其体积保持基本恒定，（iv）将循环反应介质加热到至少130℃的温度，（v）由此回收加热的反应介质到吖嗪反应区，和（vi）在沿着环的任何点，将试剂引入循环反应介质中，从而基本维持吖嗪形成反应的平衡; 最终产物吖嗪方便地水解成水合肼。

9. 发明授权

US3956282A Method for preparing azines 失效
标题翻译：制备吖嗪的方法
公开(公告)号：US3956282A
公开(公告)日：1976-05-11
申请号：US340763
申请日：1973-03-13
申请人： Pierre Tellier , Henri Mathais , Jean-Pierre Schirmann , Francis Weiss
发明人： Pierre Tellier , Henri Mathais , Jean-Pierre Schirmann , Francis Weiss
IPC分类号： C07C251/88 , C07C20060101 , C07C67/00 , C07C241/00 , C07C119/00
CPC分类号： C07C251/88
摘要： 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.
摘要翻译：公开了一种用于制备式R1R1的对称吖嗪的方法。方法C = NN = C ANGLE（I）R2R2 R1R1角度C = NN = C角度（II）R3R3 R3R3角度C = NN = C角度（III）R4R4和不对称吖嗪式（I），（II）和（IV）和（I），（III）的混合物，其中R 1，R 2，R 3，R 3，R 3，和（V），其中R 1，R 2，R 3和R 4各自为氢原子，具有1至12个碳原子的直链烷基，支链烷基或未取代的或烷基取代的3至12个碳原子的环烷基原子，含有6至12个碳原子的含有芳香核的烃基; 进一步提供R1和R2可以相同或不同的基团，并且R3和R4是相同或不同的基团，并且各自不同于R1和R2; 或者R 1和R 2或R 1，R 3或R 3或R 4和R 4与R 4相同的碳原子一起形成未取代的或脂族取代的3-11个碳原子的亚烷基，上述每个基团是未取代的或被一个或多个基团取代，在其中产生吖嗪的培养基中是稳定的。

10. 发明授权

US3978049A Process for the preparation of hydrazine compounds 失效
公开(公告)号：US3978049A
公开(公告)日：1976-08-31
申请号：US433710
申请日：1974-01-16
申请人： Jean-Pierre Schirmann , Pierre Tellier , Henri Mathais , Francis Weiss
发明人： Jean-Pierre Schirmann , Pierre Tellier , Henri Mathais , Francis Weiss
IPC分类号： C07D213/42 , B01J21/00 , B01J23/00 , C07B43/00 , C07B61/00 , C07C20060101 , C07C67/00 , C07C241/00 , C07C251/76 , C07C251/82 , C07C251/84 , C07C251/86 , C07C251/88 , C07D213/53 , C07C109/00
CPC分类号： C07C251/88 , C07C249/16
摘要： 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.

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