Hydrogenolysis of glycerol

• US 6,080,898 A
• Filed: 07/23/1998
• Issued: 06/27/2000
• Est. Priority Date: 07/23/1997
• Status: Expired due to Fees

• Current Assignee: Shell Oil Company (Shell Plc)
• Original Assignee: Shell Oil Company (Shell Plc)
• Inventors: Jager, Willem Wabe, Drent, Eit
• Primary Examiner(s): PADMANABHAN, SREENIVASAN
• Application Number:
  US09/121,465
• Time in Patent Office: 705 Days
• Field of Search: 568/449, 568/486, 568/492, 568/861, 568/862, 568/863
• US Class Current: 568/861
• CPC Class Codes: C07C 29/60 by elimination of -OH groups, e.g. by dehydration C07C29/34 takes precedence
• CPC Class Codes: C07C 31/10 containing three carbon atoms
• CPC Class Codes: C07C 31/205 1,3-Propanediol; 1,2-Propanediol
• CPC Class Codes: C07C 45/52 by dehydration and rearrangement involving two hydroxy groups in the same molecule
• CPC Class Codes: C07C 47/22 Acryaldehyde; Methacryaldehyde

Abstract

A process for the catalytic hydrogenolysis of glycerol in the presence of a homogeneous catalyst that is based on a platinum group metal or a compound of a platinum group metal, an anion source, and a metal-complexing compound of the formula Q¹ Q² MQ³ (I) or Q¹ Q² MQMQ³ Q⁴ (II) wherein M represents phosphorus, arsenic or antimony, Q represents a group that is covalently bonded to both M'"'"'s and having at least two carbon atoms in the bridge and Q¹ to Q⁴ are independently similar or dissimilar optionally substituted hydrocarbyl groups or Q¹ and Q² and/or Q³ and Q⁴ represent similar or dissimilar optionally substituted hydrocarbylene groups.

Claims

1. In a process for the catalytic hydrogenolysis of glycerol in the presence of a homogeneous catalyst, the improvement wherein the homogeneous catalyst is based on a platinum group metal or a compound of a platinum group metal, an anion source, and a metal-complexing compound of the formula Q¹ Q² MQ³ (I) or Q¹ Q² MQMQ³ Q⁴ (II) wherein M represents phosphorus, arsenic or antimony, Q represents a group that is covalently bonded to both M'"'"'s and has at least two carbon atoms in the bridge, and Q¹ to Q⁴ are independently similar or dissimilar optionally substituted hydrocarbyl groups or Q¹ and Q² and/or Q³ and Q⁴ together represent similar or dissimilar optionally substituted hydrocarbylene groups;

wherein the process is carried out at a temperature in the range of 50 to 250°

C. and at a pressure in the range of 5 to 100 bar.

2. The process of claim 1 wherein the platinum group metal is platinum or palladium.

3. The process of claim 1 wherein an acid having a pKa value of less than 3, measured in aqueous solution at 18°

C., is the anion source.

4. The process of claim 1 that is carried out in the presence of a catalyst system comprising a halide anion as the anion source.

5. The process of claim 1 wherein each M in the metal-complexing compound is phosphorus.

6. The process of claim 1 wherein a metal-complexing compound of formula (II) is used.

7. The process of claim 1 wherein Q¹ together with Q², and in case of a compound of general formula (II) Q³ together with Q⁴, represent an optionally substituted hydrocarbylene group.

8. The process of claim 1 that is carried out in the presence of sulpholane, water or a mixture thereof.