Mild catalytic reduction of C—O bonds and C═O bonds using a recyclable catalyst system
AssigneeOrganofuel Sweden AB
InventorsArmando Córdova, Samson Afewerki, Carlos Palo-Nieto
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Abstract
A method of reducing a C—O bond to the corresponding C—H bond in a substrate, which could be a benzylic alcohol, allylic alcohol, ester or an ether bond beta to a hydroxyl group or alpha to a carbonyl group using a recyclable metal catalyst system. The recyclable catalyst system is also applicable to reducing a C═O bond to the corresponding C—OH bond and then C—H bond. These methodologies can be linked in one-pot to selective oxidation and depolymerizations of aromatic polyols such as lignin.
Claims21
A method of conversion of a C═O bond to a C—H bond, comprising the steps of:
- i. providing an alcohol and converting the alcohol to a compound comprising a C═O bond, wherein the compound comprising a C═O is selected from the group consisting of an aldehyde and a ketone, wherein the conversion of the alcohol to a compound comprising a C═O bond comprises the step of:
- oxidation with an oxidant and catalyst, wherein the oxidant is selected from the group consisting of H2O2, O2, and NaOCl, and wherein the catalyst is selected from the group consisting of heterogeneous supported metal catalyst, homogeneous organometallic complex, metal-free catalyst (mediator), and enzyme (EC 1:10:3:2);
- ii. providing the compound comprising a C═O bond from the previous step;
- and
- iii. reducing said compound comprising a C═O bond in a solvent comprising reducing agent and a catalyst, wherein the catalyst is selected from the group consisting of a heterogeneous metal catalyst and homogeneous organometallic complex, wherein the catalyst is a Pd-catalyst selected from the group consisting of Pd(0)-AmP-MCF and Pd(0)-AmP-CPG which is heterogeneously supported on silica containing material.
A method of conversion of a C—O or C═O bond to a C—H bond, comprising:
- i. providing a compound comprising a C—O bond or a C═O bond, wherein said compound is selected from the group consisting of an aldehyde, a ketone, an alcohol, an aldol, a compound having an ether bond beta to a hydroxyl group, or a compound having an ether bond alpha to a carbonyl group;
- and
- ii. reducing the C—O or C═O bond to a C—H bond in a solvent comprising a reducing agent and a catalyst, wherein the catalyst is selected from the group consisting of a heterogeneous metal catalyst and homogeneous organometallic complex, wherein the catalyst is a Pd-catalyst selected from the group consisting of Pd(0)-AmP-MCF and Pd(0)-AmP-CPG, which is heterogeneously supported on silica containing material wherein the catalyst is a Pd-catalyst selected from the group consisting of Pd(0)-AmP-MCF and Pd(0)-AmP-CPG, wherein the homogeneous organometallic complex comprises Pd, Ir, Ru, Ni, Co, Cu complexes;
- and
- iii. wherein an optional step of providing an alcohol and then converting the alcohol to a compound comprising a C═O bond is provided before step i).
Dependencies are inferred from the claim text.