Method and apparatus for conducting microwave assisted organic reactions with gas-phase reactants

• US 7,955,479 B2
• Filed: 03/07/2006
• Issued: 06/07/2011
• Est. Priority Date: 03/07/2006
• Status: Active Grant

• Current Assignee: CEM Global LLC
• Original Assignee: CEM Global LLC
• Inventors: Vanier, Grace S.
• Primary Examiner(s): Wong; Edna
• Application Number:
  US11/370,139
• Publication Number:
  US 20070209924A1
• Time in Patent Office: 1,918 Days
• Field of Search: 204/157.15, 204/157.6
• US Class Current: 204/157.15
• CPC Class Codes: B01J 19/126 Microwaves
• CPC Class Codes: B01J 2219/00006 Large-scale industrial plants
• CPC Class Codes: B01J 2219/00063 of the reactants
• CPC Class Codes: B01J 2219/0009 Coils
• CPC Class Codes: B01J 2219/00108 involving reactant vapours
• CPC Class Codes: B01J 2219/00162 controlling the pressure
• CPC Class Codes: B01J 2219/1215 Single reactor
• CPC Class Codes: B01J 2219/1227 Reactors comprising tubes with open ends
• CPC Class Codes: B01J 2219/123 Vessels in the form of a cup
• CPC Class Codes: B01J 2219/1233 Closure means, such as lids, caps, seals B01J3/03 takes precedence; pressure relief systems in the lid, e.g. rupture discs B01J2219/0027
• CPC Class Codes: B01J 2219/1239 Means for feeding and evacuation
• CPC Class Codes: B01J 2219/126 in the form of a closed housing
• CPC Class Codes: B01J 2219/1269 Microwave guides
• CPC Class Codes: B01J 2219/1293 Single source
• CPC Class Codes: C07B 2200/07 Optical isomers
• CPC Class Codes: C07B 35/02 Reduction
• CPC Class Codes: C07C 209/26 by reduction with hydrogen
• CPC Class Codes: C07C 209/36 by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
• CPC Class Codes: C07C 209/365 by reduction with preservation of halogen-atoms in compounds containing nitro groups and halogen atoms bound to the same carbon skeleton
• CPC Class Codes: C07C 211/45 Monoamines
• CPC Class Codes: C07C 211/46 : Aniline
• CPC Class Codes: C07C 211/52 : the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
• CPC Class Codes: C07C 2523/44 : Palladium
• CPC Class Codes: C07C 29/17 : by hydrogenation of carbon-to-carbon double or triple bonds
• CPC Class Codes: C07C 29/172 : with the obtention of a fully saturated alcohol
• CPC Class Codes: C07C 31/125 : containing five to twenty-two carbon atoms
• CPC Class Codes: C07C 5/03 : of non-aromatic carbon-to-carbon double bonds
• CPC Class Codes: C07C 67/303 : by hydrogenation of unsaturated carbon-to-carbon bonds
• CPC Class Codes: C07C 69/40 : Succinic acid esters
• CPC Class Codes: C07C 69/612 : Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
• CPC Class Codes: C07D 207/08 : with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 207/16 : Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07J 9/00 : Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
• CPC Class Codes: H05B 6/802 : for heating fluids methods of heating fluids in conventional microwave ovens H05B6/687

Abstract

A method of accelerating the hydrogenation of organic compounds is provided. The method includes positioning an microwave transparent reaction vessel containing at least one reactant suitable for hydrogenation in a microwave cavity, purging the reaction vessel, charging the reaction vessel with hydrogen gas, and applying a continuous single mode of microwave radiation within the cavity and to the vessel and its contents for a time sufficient to effect a chemical change in the reactants.

Claims

1. A method of accelerating organic reactions that include a gas phase reactant, the method comprising:

conducting a hydrogenation reaction selected from the group consisting of olefin hydrogenation, alkyne hydrogenation, carbobenzyloxy deprotection, and reductive amination, using the steps of;

introducing a microwave transparent reaction vessel containing an organic compound to be hydrogenated into a microwave cavity;

purging the reaction vessel containing the organic compound to be hydrogenated;

charging the reaction vessel with hydrogen gas in an amount that is at least stoichiometric with respect to the amount of the organic compound to be hydrogenated;

applying a continuous single mode of microwave radiation within the cavity and to the vessel and the organic compound in the vessel until the organic compound is hydrogenated to a desired yield; and

venting the vessel at the completion of the hydrogenation reaction.

2. The method of accelerating organic reactions according to claim 1 further comprising catalyzing the reaction with a hydrogenation catalyst.

3. The method of accelerating organic reactions according to claim 2 wherein the hydrogenation catalyst is a palladium catalyst.

4. The method of accelerating organic reactions according to claim 1 wherein the step of purging the reaction vessel comprises purging the reaction vessel more than one time.

5. The method of accelerating organic reactions according to claim 1 wherein the step of charging the reaction vessel with hydrogen gas comprises charging the reaction vessel with an amount of hydrogen gas that is greater than stoichiometric with respect to the organic compound to be hydrogenated.

6. The method of accelerating organic reactions according to claim 1 further comprising the step of monitoring the temperature of the reaction vessel.

7. The method of accelerating organic reactions according to claim 1 comprising applying the continuous single mode of microwave radiation within the cavity and to the reaction vessel and to the organic compound to be hydrogenated for a time sufficient to effect a yield of greater than 50% hydrogenation.

8. The method of accelerating organic reactions according to claim 1 comprising applying the continuous single mode of microwave radiation within the cavity and to the reaction vessel and to the organic compound to be hydrogenated for a time sufficient to effect a yield of greater than about 75% hydrogenation.

9. The method of accelerating organic reactions according to claim 1 comprising applying the continuous single mode of microwave radiation within the cavity and to the reaction vessel and to the organic compound to be hydrogenated for a time sufficient to effect a yield of greater than about 90% hydrogenation.

10. The method of accelerating organic reactions according to claim 1 comprising applying the continuous single mode of microwave radiation within the cavity and to the vessel and to the organic compound to be hydrogenated to produce a temperature sufficient to hydrogenate the organic compound to be hydrogenated to the desired yield.

11. The method of accelerating organic reactions according to claim 1 further comprising cooling the reaction vessel during the application of microwave radiation to moderate and control the temperature of the reaction vessel and the organic compound to be hydrogenated.

12. The method of accelerating organic reactions according to claim 1 wherein the step of applying a continuous single mode of microwave radiation within the cavity and to the vessel and to the organic compound to be hydrogenated comprises heating the vessel contents to a temperature of between about 60 and 180°

C.