# US 9,040,755 B2 · Hydrogenation of styrene oxide forming 2-phenyl ethanol

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- Number: US 9,040,755 B2
- Document ID: US9040755B2
- Status: Granted
- Kind: B2
- Application number: 14/365,592
- Filed: 2012-12-14
- Published: 2014-11-06
- Granted: 2015-05-26
- Earliest claimed: 2011-12-15
- Assignees: Council of Scientific and Industrial Research
- Applicants: Council of Scientific and Industrial Research
- Inventors: Hari Chand Bajaj; Sayed Hasan Razi Abdi; Rukhsana Ilyas Kureshy; Noor-Ul Hasan Khan; Aasif Asharafbhai Dabbawala; Tamal Roy
- Web page: https://patentgrep.com/patent/US9040755B2

## CPC

- C07C 29/132: by reduction of an oxygen containing functional group
- B01J 23/44: Palladium
- B01J 23/58: with alkali- or alkaline earth metals
- B01J 27/236: Hydroxy carbonates
- B01J 29/7415: {Zeolite Beta}
- B01J 35/613: {10-100 m2/g}
- B01J 37/009: {Preparation by separation, e.g. by filtration, decantation, screening}
- B01J 37/0201: {Impregnation}
- B01J 2229/186: not in framework positions
- B01J 2235/00: Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
- B01J 2235/10: Infrared [IR]
- B01J 2235/15: X-ray diffraction
- Y02P 20/50: Improvements relating to the production of bulk chemicals
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A process for preparation of 2-phenyl ethanol by catalytic hydrogenation of styrene oxide using a catalyst consisting of Pd (II) on basic inorganic support is investigated. The present invention comprises development of new Pd based catalysts. The present method yields 2-phenyl ethanol in 98% selectivity at total conversion of styrene oxide. The present process represents an environment friendly alternative to conventionally used methods in industry and eliminates the reduction step for catalyst preparation. In the present invention the active catalyst is generated in situ during the hydrogenation of styrene oxide. In addition, Pd (II) supported catalysts do not catch fire (non pyrophoric), can be stored under ambient conditions and produce very less or no dust which makes said catalysts suitable for industrial application.

## Claims

### Claim 1

A process for the preparation of 2-phenyl ethanol using Pd(II) salt on a basic support as precatalyst without calcination, wherein said process comprises the steps of:
(a) mixing styrene oxide, an organic solvent and Pd(II) salt on basic support as precatalyst under stirring followed by flushing the reaction mixture with hydrogen gas at a temperature ranging between 24° C. to 30° C.;
(b) pressurizing the reaction mixture as obtained in step (a) with hydrogen gas at 400-800 pounds per square inch gauge (psig) followed by stirring at a speed rate ranging between 800-1300 revolutions per minute (rpm) at a temperature ranging between 24° C. to 30° C. for a period ranging between 1 h to 5 h, subsequently maintaining hydrogen pressure inside the reactor by intermittent supply of hydrogen gas;
(c) depressurizing the reaction mixture as obtained in step (b) at a temperature ranging between 24° C. to 30° C.;
(d) separating the catalyst Pd(0) on a basic support which generates in situ from the reaction mixture as obtained in step (c) by decantation/filtration and obtaining 2-phenyl ethanol with organic solvent; and
(e) distilling the solvent from 2-phenyl ethanol with organic solvent as obtained in step (d) to obtain solid 2-phenyl ethanol.

### Claim 2 (depends on 1)

The process as claimed in claim 1, wherein the Pd (II) salt in step (a) is selected from the group consisting of chloride, bromide, iodide, nitrate, oxide, cyanide, sulfate, trifluoroacetate, acetate, acetylacetonate and tetraammine dichloro.

### Claim 3 (depends on 1)

The process as claimed in claim 1, wherein the basic support in step (a) is selected from the group consisting of hydrotalcite, MgO, CaO, basic alumina, barium carbonate, calcium carbonate, and alkali zeolites.

### Claim 4 (depends on 3)

The process as claimed in claim 3, wherein hydrotalcite is used having Mg: Al ratio ranging from 2 to 6 by weight.

### Claim 5 (depends on 1)

The process as claimed in claim 1, wherein the loading of Pd on the basic support in step (a) is in the range of 0.1 to 10% by weight.

### Claim 6 (depends on 1)

The process as claimed in claim 1, wherein loading of Pd on the basic support in step (a) is carried out by an impregnation method.

### Claim 7 (depends on 1)

The process as claimed in claim 1, wherein Pd(II) on a basic support in step (a) is used with styrene oxide: precatalyst ratio ranging from 5 to 200 by weight.

### Claim 8 (depends on 1)

The process as claimed in claim 1, wherein the organic solvent used in step (a) is selected from methanol, ethanol, propanol, isopropanol, butanol, 1,4-dioxane, tetrahydrofuran, acetone, acetonitrile, toluene, benzene, cyclohexane, hexane, N,N-dimethylformamide, N,N-dimethylacetamide, chloroform, carbon tetrachloride, dichloromethane and dichloroethane.

### Claim 9 (depends on 1)

The process claimed in claim 1, wherein selectivity of 2-phenyl ethanol is in the range of 90-99%.

### Claim 10 (depends on 3)

The process as claimed in claim 3, wherein the zeolite is Na beta zeolite or Na ZSM-5.

### Claim 11

A process for the preparation of 2-phenyl ethanol comprising:
contacting styrene oxide, in an organic solvent, with Pd(0) catalyst generated in situ from Pd(II) precatalyst on a basic support without calcination to obtain 2-phenyl ethanol dissolved in the organic solvent;
separating the Pd(0) catalyst on the basic support; and
removing the solvent to obtain 2-phenyl ethanol.