IP Library Granted Patent US 9,822,052
Granted Patent B2
US 9,822,052 · App. 15/279,837 · Granted Nov 21, 2017

Nanoparticle catalysts for conversion of cyclohexanol to cyclohexanone

Inventors: Alan B. Levy (Randolph, NJ); Scott R. Keenan (Marlton, NJ); Robert Raja (Fair Oak, GB); Arran M. Gill (Guiseley, GB); Matthew E. Potter (Leigh, GB); Sivan A. Van Aswegen (Tunbridge Wells, GB)
Assignees: ADVANSIX RESINS & CHEMICALS LLC; UNIVERSITY OF SOUTHAMPTON
C07C45/39B01J27/13B01J27/1856B01J37/04B01J37/088C07C2601/14
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Quick Facts
Patent No.
US 9,822,052
App. No.
15/279,837
Granted
Nov 21, 2017
Kind
B2
Abstract

Methods for converting an alcohol, such as cyclohexanol to a ketone, such as cyclohexanone, include reacting the alcohol in the presence of a catalyst and oxygen to produce the ketone. In one exemplary embodiment, the catalyst comprises a microporous copper chloropyrophosphate framework including a plurality of noble metal nanoparticles. In one exemplary embodiment, the noble metal nanoparticles include at least one metal selected from the group consisting of platinum, palladium, and gold.

Claims (16)

1. A method of converting an alcohol to a ketone, comprising:

reacting the alcohol in the presence of a catalyst and oxygen to produce the ketone, wherein the catalyst comprises a microporous copper chloropyrophosphate framework including a plurality of noble metal nanoparticles.

2. The method of claim 1 , wherein the alcohol is a cyclic alcohol.

3. The method of claim 2 , wherein the alcohol is cyclohexanol and the ketone is cyclohexanone.

4. The method of claim 3 , further comprising providing a mixture of cyclohexanone and cyclohexanol, wherein the provided cyclohexanol is reacted in said reacting step.

5. The method of claim 4 , wherein the mixture comprises 5 wt. % to 95 wt. % cyclohexanol, based on the total weight of the cyclohexanol and cyclohexanone.

6. The method of claim 4 , wherein the mixture comprises 40 wt. % to 60 wt. % cyclohexanol, based on the total weight of the cyclohexanol and cyclohexanone.

7. The method of claim 1 , wherein the noble metal nanoparticles include at least one metal selected from the group consisting of platinum, palladium, and gold.

8. The method of claim 1 , wherein the noble metal nanoparticles include at least two metals selected from the group consisting of platinum, palladium, and gold.

9. A catalyst comprising a bimetallic microporous copper chloropyrophosphate framework including a plurality of platinum and gold noble metal nanoparticles, the microporous copper chloropyrophosphate framework having a general formula of Rb 9 Cu 6 (P 2 O 7 ) 4 Cl 4 (AuCl 4 )Rb 9 Cu 6 (P 2 O 7 ) 4 Cl 3 (PtCl 4 ).

10. The catalyst of claim 9 , wherein the catalyst has been activated at a temperature of about 300° C.

11. A method of making a catalyst, the method comprising:

mixing copper (II) fluoride, orthophosphoric acid, rubidium hydroxide, rubidium chloride, and at least one source of metal chloride;

heating the mixture in a sealed container to form a catalyst precursor including precursor complexes; and

activating the catalyst by heating the catalyst precursor at a temperature of at least 175° C. to converting the precursor complexes to noble metal nanoparticle sites.

12. The method of claim 11 , wherein the source of metal chloride is selected from the group consisting of K 2 PtCl 4 , K 2 PdCl 4 , HAuCl 4 , and KAuCl 4 .

Assignments (6)
SECURITY INTEREST Recorded Oct 27, 2021
From: ADVANSIX INC.; ADVANSIX RESINS & CHEMICALS LLC
To: TRUIST BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 057940/0794 →
RELEASE OF SECURITY INTEREST Recorded Oct 27, 2021
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: ADVANSIX INC.; ADVANSIX RESINS & CHEMICALS LLC
Reel/Frame 057941/0536 →
SECURITY INTEREST Recorded May 2, 2018
From: ADVANSIX INC.; ADVANSIX RESINS & CHEMICALS LLC
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045696/0109 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2017
From: HONEYWELL INTERNATIONAL INC.
To: ADVANSIX RESINS & CHEMICALS LLC
Reel/Frame 042016/0029 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2017
From: LEVY, ALAN B.; KEENAN, SCOTT R.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 041366/0520 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2017
From: RAJA, ROBERT; GILL, ARRAN M.; POTTER, MATTHEW E.; VAN ASWEGEN, SIVAN A.
To: UNIVERSITY OF SOUTHAMPTON
Reel/Frame 041811/0415 →
Continuity (2)
Provisional Application 62235684 · Oct 1, 2015
Related Publication 20170096380A1 · Apr 6, 2017