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    • 6. 发明授权
    • Process for the preparation of hydrazine compounds
    • US3978049A
    • 1976-08-31
    • US433710
    • 1974-01-16
    • Jean-Pierre SchirmannPierre TellierHenri MathaisFrancis Weiss
    • Jean-Pierre SchirmannPierre TellierHenri MathaisFrancis Weiss
    • C07D213/42B01J21/00B01J23/00C07B43/00C07B61/00C07C20060101C07C67/00C07C241/00C07C251/76C07C251/82C07C251/84C07C251/86C07C251/88C07D213/53C07C109/00
    • C07C251/88C07C249/16
    • 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.
    • 9. 发明授权
    • Method for preparing symmetrical and unsymmetrical ketazines and
mixtures thereof
    • 制备对称和不对称的喹的方法及其混合物
    • US3972874A
    • 1976-08-03
    • US531058
    • 1974-12-09
    • Henri MathaisJean-Pierre SchirmannFrancis Weiss
    • Henri MathaisJean-Pierre SchirmannFrancis Weiss
    • C07C109/00
    • C07C251/88
    • 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:A. oxidizing a secondary alcohol of the formula ##EQU4## alone or together with a different secondary alcohol of the formula ##EQU5## or ##EQU6## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each has the same meaning as defined above, the oxidation to be carried out in the liquid phase employing molecular oxygen or a gaseous mixture containing the same, at a temperature and pressure which is sufficient to maintain the alcohol or alcohols in the liquid phase and result in a liquid phase mixture containing the peroxidic products of the auto-oxidation of the alcohol (VI) or the alcohols (VI) and (VII) or (VI) and (VIII);b. reacting the peroxidic products with ammonia in the presence of cyanogen or a nitrile R.sup.5 (CN).sub.n (IX) wherein n is an integer of from 1 to 6 and R.sup.5 is an unsubstituted or substituted saturated aliphatic, acyclic, or cyclic radical of from 1 to 12 carbon atoms or a phenyl or pyridinyl radical to result in the ketazine (I) or the mixture of ketazines (I), (II) and (IV) or (I), (III) and (V); andC. recovering the ketazine or mixture of ketazines.
    • 本发明涉及一种制备式R1R1对称的嗪酮的方法。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 式(R1)的非对称性的喹诺酮C = NN = C角度(IV)R2R3 R1R3角C = NN = C角(V)R2R4以及它们的混合物(I),(II)和(IV)和(I) III)和(V)其中R 1,R 2,R 3和R 4各自为具有1至12个碳原子的直链烷基,具有3至12个碳原子的支链烷基或环烷基,或苯基, 上述基团是未取代的或被其中制备该酮的培养基中稳定的基团取代; 并且在这种情况下,R 1和R 2可以是相同或不同的基团,并且R 3和R 4是彼此不同的基团,并且各自是与R 1和R 2不同的基团。 或R 1和R 2,或R 1和R 3,或任意一个或两个ANGLE C = N-部分的R 3和R 4一起形成在环中具有3至11个碳原子的环状或取代的环状基团,其包括:
    • 10. 发明授权
    • Method for preparing azines
    • 制备吖嗪的方法
    • US3956282A
    • 1976-05-11
    • US340763
    • 1973-03-13
    • Pierre TellierHenri MathaisJean-Pierre SchirmannFrancis Weiss
    • Pierre TellierHenri MathaisJean-Pierre SchirmannFrancis Weiss
    • C07C251/88C07C20060101C07C67/00C07C241/00C07C119/00
    • C07C251/88
    • 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.
    • 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。