Selective hydrogenation catalyst and selective hydrogenation method using the same
The present invention relates to a Ru—Pd bimetallic catalyst for use in hydrogenation of a compound, and more particularly to a catalyst prepared by loading both ruthenium and palladium on a g-C 3 N 4 support and to a selective hydrogenation process of a pyridine group in a reaction system containing both a pyridine group and a benzene group using the catalyst.
1. A selective hydrogenation method, comprising selectively hydrogenating a pyridine compound of Chemical Formula 2 below in a mixture of a benzene compound represented by Chemical Formula 1 below and the pyridine compound represented by Chemical Formula 2 using a Ru—Pd/g-C 3 N 4 catalyst in which ruthenium and palladium as active components are loaded on a g-C 3 N 4 support so that a sum of weights of the active components is 0.1 to 15 wt % based on a total weight of the catalyst including the support and a weight ratio (b/a) of the ruthenium (b) relative to the palladium (a) ranges from 0.25 to 10:
wherein, in Chemical Formulas 1 and 2, R is hydrogen, a C 1 -C 13 alkyl or cycloalkyl group, a C 7 -C 13 arylalkyl group, C 1 -C 13 alkyl alcohol, or C 1 -C 13 alkylether.
2. The selective hydrogenation method of claim 1 , wherein a mass of the Ru—Pd/g-C 3 N 4 catalyst is 0.5 to 10 wt % based on a total weight of reactants that are used.
3. The selective hydrogenation method of claim 1 , performed at a temperature ranging from 20 to 200° C.
4. The selective hydrogenation method of claim 1 , performed at a pressure ranging from 1 to 100 bar.
5. A selective hydrogenation method, comprising selectively hydrogenating a pyridine group in a compound represented by Chemical Formula 3 below using a Ru—Pd/g-C 3 N 4 catalyst in which ruthenium and palladium as active components are loaded on a g-C 3 N 4 support so that a sum of weights of the active components is 0.1 to 15 wt % based on a total weight of the catalyst including the support and a weight ratio (b/a) of the ruthenium (b) relative to the palladium (a) ranges from 0.25 to 10:
in Chemical Formula 3,
Z represents hydrogen; a C 1 -C 6 alkyl group; C 1 -C 6 alkyl alcohol; C 1 -C 6 alkylether; or
wherein Q is CH or N,
R 1 represents hydrogen, a C 1 -C 6 alkyl group, C 1 -C 6 alkyl alcohol, C 1 -C 6 alkylether or
wherein * denotes a point of attachment to the Chemical Formula 3,
R 2 represents hydrogen, a C 1 -C 6 alkyl group, C 1 -C 6 alkyl alcohol or C 1 -C 6 alkylether,
R 3 represents hydrogen, a C 1 -C 6 alkyl group, C 1 -C 6 alkyl alcohol or C 1 -C 6 alkylether, and
X 1 or X 2 represents a single bond line; —(CHR 4 ) n —, wherein n is an integer of 1 to 3, and R 4 is H, OH, or a C 1 -C 6 alkyl group, —C(═CH 2 )—, —C(O)—; or —N(R 5 )—, wherein R 5 is hydrogen or a C 1 -C 6 alkyl group.
6. A selective hydrogenation method, comprising selectively hydrogenating a pyridine compound in a mixture of a benzene compound and the pyridine compound using a Ru—Pd/g-C 3 N 4 catalyst in which ruthenium and palladium as active components are loaded on a g-C 3 N 4 support so that a sum of weights of the active components is 0.1 to 15 wt % based on a total weight of the catalyst including the support and a weight ratio (b/a) of the ruthenium (b) relative to the palladium (a) ranges from 0.25 to 10:
wherein the benzene compound is at least one selected from among benzene, toluene, xylene, cyclohexyltoluene, diphenylmethane, benzyl alcohol, phenylethyl alcohol, methyl phenyl ether, and ethyl phenyl ether, and
the pyridine compound is at least one selected from among pyridine, methylpyridine, ethylpyridine, cyclohexyl methylpyridine, benzylpyridine, pyridinemethanol, pyridylethanol, methoxypyridine, and ethoxypyridine.