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    • 11. 发明授权
    • Method for preparing azines
    • 制备吖嗪的方法
    • US3948902A
    • 1976-04-06
    • US515156
    • 1974-10-16
    • Jean Pierre SchirmannFrancis Weiss
    • Jean Pierre SchirmannFrancis Weiss
    • C07C109/00
    • 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 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.
    • 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可以是相同或不同的基团,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和R 4与相同碳原子一起形成未取代的或具有3至11个碳原子的烷基取代的亚烷基,上述每个基团是未取代的或被一个或多个基团取代, 在生产所述吖嗪的培养基中是稳定的。
    • 16. 发明授权
    • Method for preparing hydrazo-bis-acetonitriles
    • 制备双氢 - 二乙腈的方法
    • US3984451A
    • 1976-10-05
    • US579548
    • 1975-05-21
    • Francis WeissJean-Pierre Schirmann
    • Francis WeissJean-Pierre Schirmann
    • C07C255/66C07C120/00
    • C07C251/88C07C255/00
    • 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:A. i. reacting a carbonyl compound of the general formula: ##EQU2## wherein R.sub.1 and R.sub.2 have the same meaning hereinafter given, with ammonia and hydrogen peroxide in the presence of cyanogen or a nitrile of the formulaR.sub.3 (CN).sub.n (III)wherein n is an integer from 1 to 6 and R.sub.3 is an unsubstituted or substituted saturated aliphatic, acyclic or cyclic radical of from 1 to 12 carbon atoms or a benzenyl or pyridinyl radical, to form a symmetrical azine of the formula ##EQU3## ii. oxidizing a secondary alcohol of ##EQU4## wherein R.sub.1 and R.sub.2 have the same meaning hereinafter given, at a temperature and pressure which is sufficient to maintain the alcohol in the liquid phase and result in a liquid phase mixture containing the peroxidic products of the auto-oxidation of the alcohol [v] and reacting auto-oxidation products with ammonia and cyanogen or the nitrile R.sub.3 (CN).sub.n of formula (III) to form the symmetrical azine of formula (IV)b. eliminating unreacted ammonia from the medium resulting from (a);C. reacting the azine of formula (IV) contained in the ammonia-free medium resulting from (b) with at least two moles of hydrocyanic acid per mole of azine; andD. recovering the hydrazo-bis-acetonitrile of formula (I).
    • 本发明涉及通式为R1R1 || NC-C-NH-NH-C-CN(Ⅰ)| R2R2的双氢 - 二乙腈制备方法,其中R1和R2具有以下相同的含义, 包含:
    • 17. 发明授权
    • Process for the preparation of symmetrical and unsymmetrical azines and
mixtures thereof
    • 制备对称和不对称吖嗪及其混合物的方法
    • US3972876A
    • 1976-08-03
    • US532650
    • 1974-12-13
    • Jean-Pierre SchirmannFrancis Weiss
    • Jean-Pierre SchirmannFrancis Weiss
    • C07C249/02C01B21/16C07C20060101C07C251/88C07C255/45C07C109/00
    • C07C251/88
    • 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 >C=N-- moieties together form a cyclic or substituted cyclic radicals of from 3 to 11 carbon atoms in the ring.
    • 公开了用于制备式R1R1的对称吖嗪的方法。R1 = 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 (I),(II)和(IV)和(I)的混合物,其中R 1,R 2,R 3,R 3,R 4, ,(III)和(V),其中R 1,R 2,R 3和R 4各自为氢,具有1至12个碳原子的直链烷基,支链烷基或环烷基为3至12 碳原子或苯基,上述基团是未被取代的或被在所述制备所述吖嗪的介质中稳定的基团取代; 在这种情况下,R 1和R 2可以是相同或不同的基团,R 3是不同于R 1和R 2的基团,R 3和R 4是彼此不同的基团,并且各自是不同的R 1和R 2基团; 或者R 1和R 2或R 1和R 3或R 3和R 4中的任一个或两个> C = N-部分一起形成环中具有3至11个碳原子的环状或取代的环状基团。