A method for forming a carbon-carbon bond, wherein a reaction is performed by filling a platinum group metal-supported catalyst into a filling container, and passing a raw material liquid through the platinum group metal-supported catalyst in a continuous circulation manner, and wherein the platinum group metal-supported catalyst is a platinum group metal-supported catalyst in which nanoparticles of a platinum group metal with an average particle diameter of 1 to 100 nm are supported on a non-particulate organic porous ion exchanger formed of a continuous framework phase and a continuous pore phase.

A solid-supported Pd catalyst is suitable for C—C bond formation, e.g., via Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with a support that is reusable, cost-efficient, regioselective, and naturally available. Such catalysts may contain Pd nanoparticles on jute plant sticks (GS), i.e., Pd@GS, and may be formed by reducing, e.g., K.sub.2PdCl.sub.4 with NaBH.sub.4 in water, and then used this as a “dip catalyst.” The dip catalyst can catalyze Suzuki-Miyaura and Mizoroki-Heck cross coupling-reactions in water. The catalysts may have a homogeneous distribution of Pd nanoparticles with average dimensions, e.g., within a range of 7 to 10 nm on the solid support. Suzuki-Miyaura cross-coupling reactions may achieve conversions of, e.g., 97% with TOFs around 4692 h.sup.−1, Mizoroki-Heck reactions with conversions of, e.g., a 98% and TOFs of 237 h.sup.−1, while the same catalyst sample may be used for 7 consecutive cycles, i.e., without addition of any fresh catalyst.

A solid-supported Pd catalyst is suitable for C—C bond formation, e.g., via Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with a support that is reusable, cost-efficient, regioselective, and naturally available. Such catalysts may contain Pd nanoparticles on jute plant sticks (GS), i.e., Pd@GS, and may be formed by reducing, e.g., K.sub.2PdCl.sub.4 with NaBH.sub.4 in water, and then used this as a “dip catalyst.” The dip catalyst can catalyze Suzuki-Miyaura and Mizoroki-Heck cross coupling-reactions in water. The catalysts may have a homogeneous distribution of Pd nanoparticles with average dimensions, e.g., within a range of 7 to 10 nm on the solid support. Suzuki-Miyaura cross-coupling reactions may achieve conversions of, e.g., 97% with TOFs around 4692 h.sup.−1, Mizoroki-Heck reactions with conversions of, e.g., a 98% and TOFs of 237 h.sup.−1, while the same catalyst sample may be used for 7 consecutive cycles, i.e., without addition of any fresh catalyst.

Method of forming a trisubstituted ethylene compound, the method comprising: (A) providing a trisubstituted ethylene compound bearing a first, a second and a third substituent, in which the first and the second substituent are bound to the one olefinic carbon atom and are different from one another; (B) providing a monosubstituted ethylene compound or a disubstituted ethylene compound in which the substituents are vicinally bound to the olefinic carbon atoms, bearing at least a fourth substituent, respectively; (C) subjecting the trisubstituted ethylene compound provided in step (A) to a cross-metathesis reaction with olefin provided in step (B) to form said trisubstituted ethylene, wherein the cross-metathesis reaction is catalysed by a transition metal complex bearing ligands from which one ligand is a carbene ligand, wherein the carbene complex is characterized by a M=C moiety, wherein M is the transition metal; and wherein the reaction proceeds stereoselectively.

Method of forming a trisubstituted ethylene compound, the method comprising: (A) providing a trisubstituted ethylene compound bearing a first, a second and a third substituent, in which the first and the second substituent are bound to the one olefinic carbon atom and are different from one another; (B) providing a monosubstituted ethylene compound or a disubstituted ethylene compound in which the substituents are vicinally bound to the olefinic carbon atoms, bearing at least a fourth substituent, respectively; (C) subjecting the trisubstituted ethylene compound provided in step (A) to a cross-metathesis reaction with olefin provided in step (B) to form said trisubstituted ethylene, wherein the cross-metathesis reaction is catalysed by a transition metal complex bearing ligands from which one ligand is a carbene ligand, wherein the carbene complex is characterized by a M=C moiety, wherein M is the transition metal; and wherein the reaction proceeds stereoselectively.

High activity metal nanoparticle catalysts, such as Pd or Pt nanoparticle catalyst, are provided. Adsorption of metal precursors such as Pd or Pt precursors onto carbon based materials such as graphene followed by solventless (or low-solvent) microwave irradiation at ambient conditions results in the formation of the catalysts in which metal nanoparticles are supported on i) the surface of the carbon based materials and ii) in/on/within defects/holes in the carbon based materials.

High activity metal nanoparticle catalysts, such as Pd or Pt nanoparticle catalyst, are provided. Adsorption of metal precursors such as Pd or Pt precursors onto carbon based materials such as graphene followed by solventless (or low-solvent) microwave irradiation at ambient conditions results in the formation of the catalysts in which metal nanoparticles are supported on i) the surface of the carbon based materials and ii) in/on/within defects/holes in the carbon based materials.

A solid-supported Pd catalyst is suitable for C—C bond formation, e.g., via Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with a support that is reusable, cost-efficient, regioselective, and naturally available. Such catalysts may contain Pd nanoparticles on jute plant sticks (GS), i.e., Pd@GS, and may be formed by reducing, e.g., K.sub.2PdCl.sub.4 with NaBH.sub.4 in water, and then used this as a “dip catalyst.” The dip catalyst can catalyze Suzuki-Miyaura and Mizoroki-Heck cross coupling-reactions in water. The catalysts may have a homogeneous distribution of Pd nanoparticles with average dimensions, e.g., within a range of 7 to 10 nm on the solid support. Suzuki-Miyaura cross-coupling reactions may achieve conversions of, e.g., 97% with TOFs around 4692 h.sup.−1, Mizoroki-Heck reactions with conversions of, e.g., a 98% and TOFs of 237 h.sup.−1, while the same catalyst sample may be used for 7 consecutive cycles, i.e., without addition of any fresh catalyst.

A solid-supported Pd catalyst is suitable for C—C bond formation, e.g., via Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with a support that is reusable, cost-efficient, regioselective, and naturally available. Such catalysts may contain Pd nanoparticles on jute plant sticks (GS), i.e., Pd@GS, and may be formed by reducing, e.g., K.sub.2PdCl.sub.4 with NaBH.sub.4 in water, and then used this as a “dip catalyst.” The dip catalyst can catalyze Suzuki-Miyaura and Mizoroki-Heck cross coupling-reactions in water. The catalysts may have a homogeneous distribution of Pd nanoparticles with average dimensions, e.g., within a range of 7 to 10 nm on the solid support. Suzuki-Miyaura cross-coupling reactions may achieve conversions of, e.g., 97% with TOFs around 4692 h.sup.−1, Mizoroki-Heck reactions with conversions of, e.g., a 98% and TOFs of 237 h.sup.−1, while the same catalyst sample may be used for 7 consecutive cycles, i.e., without addition of any fresh catalyst.

The present invention provides a one-pot process of synthesis of phenyl naphthalene compounds that are employed as heat transfer agents. More particularly, the present invention provides a process of preparation of 1-phenylnaphthalene and 2-methyl-1-phenylnaphthalene using refinery spent catalyst. These molecules are known for application as synthetic heat transfer fluids that deliver outstanding performance and thermal stability at continuously high operating temperatures. The reaction is carried out in aqueous medium using a spent catalyst which is a palladium based charcoal catalyst as obtained from various refinery processes. Further, the present invention provides a heat resistant formulation using the synthesized polyhydrocarbons, wherein the formulation is optimized with a free radical scavenger.