System and Process for Making Phenol and/or Cyclohexanone
US-2015375135-A1 · Dec 31, 2015 · US
US9249078B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9249078-B2 |
| Application number | US-201214347422-A |
| Country | US |
| Kind code | B2 |
| Filing date | Aug 29, 2012 |
| Priority date | Oct 7, 2011 |
| Publication date | Feb 2, 2016 |
| Grant date | Feb 2, 2016 |
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Disclosed herein are catalyst compositions useful in selective decomposition of organic oxygenates. A feed comprising an organic oxygenate may be contacted with a catalyst comprising (a) at least 0.1 wt % of an oxide of an element selected from Group 3 of the Periodic Table of Elements, wherein Group 3 includes the Lanthanide series; (b) at least 0.1 wt % of an oxide of an element selected from Group 6 of the Periodic Table of Elements; and (c) at least 0.1 wt % of an oxide of at least one element selected from Group 4 of the Periodic Table of Elements, wherein the wt % s are based upon the total combined weight of the oxides in (a) through (c) and excludes any other components.
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The invention claimed is: 1. A process comprising: contacting a feed comprising an organic oxygenate with a catalyst comprising: (a) at least 0.1 wt % of an oxide of cerium; (b) at least 0.1 wt % of an oxide of tungsten; and (c) at least 0.1 wt % of an oxide of zirconium, wherein the wt % s are based upon the total combined weight of the oxides in (a) through (c) and excludes any other components; wherein the organic oxygenate is an alkyl aromatic hydroperoxide or a dialkyl ether. 2. The process of claim 1 , wherein the catalyst comprises 0.1 wt % to 30 wt % of the oxide of cerium, wherein the wt % is based upon the total combined weight of the oxides in (a) through (c) and excludes any other components. 3. The process of claim 1 , wherein the catalyst comprises 0.1 wt % to 30 wt % of the oxide of tungsten, wherein the wt % is based upon the total combined weight of the oxides in (a) through (c) and excludes any other components. 4. The process of claim 1 , wherein the organic oxygenate is an alkyl aromatic hydroperoxide. 5. The process of claim 1 , wherein the organic oxygenate is selected from cumene hydroperoxide, cyclohexylbenzene hydroperoxide, and sec-butylbenzene hydroperoxide. 6. The process of claim 1 , wherein the oxide of cerium is cerium dioxide. 7. The process of claim 1 , wherein the oxide of cerium is present in an amount of from 1 wt % to 20 wt %. 8. The process of claim 1 , wherein the oxide of tungsten is tungsten dioxide. 9. The process of claim 1 , wherein the oxide of zirconium is zirconium dioxide. 10. The process of claim 1 , wherein the weight ratio of the oxide of cerium to the oxide of tungsten is from 1:1 to 1:8. 11. The process of claim 1 , wherein said catalyst further comprises a support that contains at least one of silica, alumina, zirconia, titania, clay, carbon, and mixtures thereof. 12. A process for producing phenol, the process comprising: (i) hydroalkylating benzene with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising cyclohexylbenzene; (ii) contacting at least a portion of the cyclohexylbenzene with an oxygen-containing compound in the presence of an oxidation catalyst under oxidation conditions effective to produce an oxidation product comprising cyclohexylbenzene hydroperoxide; and (iii) contacting at least a portion of the cyclohexylbenzene hydroperoxide with a cleavage catalyst under conditions to convert said cyclohexylbenzene hydroperoxide to phenol and cyclohexanone, wherein the cleavage catalyst comprises: (a) at least 0.1 wt % of an oxide of cerium; (b) at least 0.1 wt % of an oxide of tungsten; and (c) at least 0.1 wt % of an oxide of zirconium, wherein the wt % s are based upon the total combined weight of the oxides in (a) through (c) and excludes any other components. 13. The process of claim 12 , wherein the oxide of cerium is cerium dioxide. 14. The process of claim 12 , wherein the oxide of cerium is present in an amount of from 1 wt % to 20 wt %, wherein the wt % s are based upon the total combined weight of the oxides in (a) through (c) and excludes any other components. 15. The process of claim 12 , wherein the oxide of tungsten is tungsten dioxide. 16. The process of claim 12 , wherein the weight ratio of the oxide of cerium to the oxide of tungsten is from 1:1 to 1:8. 17. The process of claim 12 , wherein the contacting step (iii) is conducted at temperature of about 20° C. to about 200° C. and a pressure of about 100 kPa, gauge to about 2000 kPa, gauge.
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