Nanohybrid catalyst for hydrogenation reactions
A nanohybrid material includes a plurality of gold nanohybrid particles having formula (I). The gold nanohybrid particles have a gold nanoparticle (AuNPs) core and a shell of at least one fatty acid derivative at least partially disposed around the AuNPs core. The AuNPs core has a cuboidal shape and an average particle size of 20 to 60 nanometers (nm). Each R 1 , and R 2 are independently selected from the group consisting of a hydrogen atom, and a fatty acid hydrocarbon chain having 16 to 22 carbon atoms. R 3 is selected from the group consisting of a hydrogen atom, an alkyl, an alkoxy, an optionally substituted alkoxy having 1 to 10 carbon atoms, and an optionally substituted alkoxyalky.
1 . A nanohybrid material, comprising:
a plurality of gold nanohybrid particles having formula (I);
wherein the gold nanohybrid particles have a gold nanoparticle (AuNPs) core and a shell of at least one fatty acid derivative at least partially disposed around the AuNPs core;
wherein the AuNPs core has a cuboidal shape and an average particle size of 20 to 60 nanometers (nm);
wherein formula (I) is
wherein each R 1 , and R 2 are independently selected from the group consisting of a hydrogen atom, and a fatty acid hydrocarbon chain having 16 to 22 carbon atoms;
wherein R 3 is selected from the group consisting of a hydrogen atom, an alkyl, an alkoxy, an optionally substituted alkoxy having 1 to 10 carbon atoms, and an optionally substituted alkoxyalky; and
n is any positive integer.
2 . The nanohybrid material of claim 1 , having a multi-layered porous structure.
3 . The nanohybrid material of claim 2 , wherein the multi-layered porous structure of the nanohybrid material has an average layer thickness of 60 to 500 nm.
4 . The nanohybrid material of claim 1 , having a pore size of 1 to 20 micrometers (μm).
5 . The nanohybrid material of claim 1 , wherein a weight ratio of the AuNPs core to the fatty acid derivative shell in the nanohybrid material ranges from about 1:10 to 1:50.
6 . The nanohybrid material of claim 1 , wherein the AuNPs core comprises Au nanoparticles having a plurality of carboxylate functional groups, wherein the at least one fatty acid derivative is connected to a carboxylate functional group of the plurality of carboxylate functional groups of the Au nanoparticles.
7 . The nanohybrid material of claim 1 , wherein the gold nanohybrid particles are uniformly distributed throughout the nanohybrid material and not forming aggregates.
8 . The nanohybrid material of claim 1 , wherein the gold nanohybrid particle is (9Z,9′Z,9″Z,12Z,12′Z,12″Z)-5-((2-hydroxyethoxy)carbonyl)benzene-1,2,3-triyl tris(octadeca-9,12-dienoate) (AuNPs/HCBTDE) having formula (II)
and n is any positive integer.
9 . A method of making the nanohybrid material of claim 8 , comprising:
mixing and dissolving at least one fatty acid derivative having formula (III) in a first solvent to form a surfactant solution;
drop-wise adding the surfactant solution into a dispersion containing the AuNPs under continuous agitation to from a reaction mixture containing the nanohybrid material; and
drying the reaction mixture to from the nanohybrid material;
wherein formula (III) is
10 . The method of claim 9 , wherein a volume ratio of the surfactant solution to the dispersion is in a range of 1:2 to 1:10.
11 . The method of claim 9 , wherein the AuNPs present in the dispersion have an average particle size of 30 to 50 nm.
12 . The method of claim 9 , further comprising:
preparing the at least one fatty acid derivative of formula (III) by:
mixing a fatty acid and a trihydroxybenzoic acid in a second solvent in the presence of a sulfonic acid and refluxing to form a first product having formula (IV);
mixing the first product and ethylene glycol in the second solvent in the presence of a sulfonic acid and refluxing to form the at least one fatty acid derivative having formula (III).
13 . The method of claim 12 , wherein a molar ratio of the fatty acid to the trihydroxybenzoic acid is in a range of 2:1 to 1:2.
14 . The method of claim 12 , wherein a molar ratio of the first product to the ethylene glycol is in a range of 2:1 to 1:2.
15 . The method of claim 12 , wherein the fatty acid is octadeca-9,12-dienoic acid.
16 . The method of claim 12 , wherein the second solvent is xylene, and wherein the sulfonic acid is p-toluene sulfonic acid.
17 . A method of benzaldehyde hydrogenation, comprising:
mixing and heating an aromatic aldehyde compound, and the nanohybrid material of claim 1 under a hydrogen flow thereby reducing the aromatic aldehyde compound with hydrogen molecules to form a reduction product;
wherein the reduction product is at least one selected from the group consisting of a substituted aromatic alcohol derivative, a substituted aromatic derivative, and an arene.
18 . The method of claim 17 , wherein up to 80 wt. % of the aromatic aldehyde compound is reduced to form the reduction product at a temperature of 100 to 200° C., each wt. % based on an initial weight of the aromatic aldehyde compound.
19 . The method of claim 17 , wherein a weight ratio of the nanohybrid material to the aromatic aldehyde compound is in a range of 1:200 to 1:10.