Process for making 2,3-dihalopropanols

• US 6,350,922 B1
• Filed: 12/16/1999
• Issued: 02/26/2002
• Est. Priority Date: 12/18/1998
• Status: Expired due to Fees

• Current Assignee: The Dow Chemical Company (Dow, Inc.)
• Original Assignee: The Dow Chemical Company (Dow, Inc.)
• Inventors: Campbell, Robert M., Vosejpka, Paul C., Ito, Larry N., Maughon, Bob R., Hucul, Dennis A.
• Primary Examiner(s): Vollano, Jean F.
• Application Number:
  US09/464,682
• Time in Patent Office: 803 Days
• Field of Search: 568/841, 568/842, 568/846, 549/514, 549/520
• US Class Current: 568/846
• CPC Class Codes: C07C 29/141 with hydrogen or hydrogen-containing gases
• CPC Class Codes: C07C 31/36 the halogen not being fluorine

Abstract

A process for making 2,3-dihalopropanol including reacting 2,3-dihalopropanal with a hydrogenating agent in the presence of an iridium and a second transition metal mixed metal catalyst where the second transition metal is selected from the group comprising ruthenium, iron, molybdenum, tungsten, rhenium, osmium, manganese or vanadium, under conditions such that 2,3-dihalopropanol is formed. The 2,3-dihalopropanol is particularly useful in a process for making epihalohydrin.

Claims

1. A process for making 2,3-dihalopropanol comprising the step of reacting 2,3-dihalopropanal with a hydrogenating agent in the presence of a heterogeneous mixed transition metal catalyst under the conditions such that 2,3-dihalopropanol is formed, wherein the heterogeneous mixed transition metal catalyst comprises an iridium metal as a first transition metal and at least a second transition metal selected from the group consisting of ruthenium, iron, molybdenum, tungsten, rhenium, osmium, or vanadium;

and wherein the atomic ratio of iridium metal to said second transition metal is from about 0.02 to about 15 such that iridium metal plus the second transition metal used as a mixed metal catalyst provides a sustained high catalytic activity and a high selectivity to the 2,3-dihalopropanol superior to the pure iridium metal used as a metal catalyst.

2. The process in claim 1 wherein the second transition metal is ruthenium.

3. The process of claim 2 wherein the atomic ratio of iridium metal to ruthenium metal is from about 0.15 to 8.

4. The process of claim 3 wherein the atomic ratio of iridium metal to ruthenium metal is from about 0.3 to 2.

5. The process of claim 1 wherein the catalyst is a heterogeneous catalyst which contains the iridium and second transition metal deposited upon a supporting material.

6. The process of claim 5 wherein the supporting material is selected from the group consisting of silica, silylated silica, carbon, alumina, titania, zirconia, magnesia and combinations thereof.

7. The process of claim 6 wherein the supporting material is a silylated silica.

8. The process of claim 1 wherein the catalyst includes a Group I or transition metal promoter ion.

9. The process of claim 8 wherein the promoter ion is selected from the group consisting of Li, Na, K, Cs, Fe, Mo, W, V, Mn, Os, Pt, Pd, Rh and mixtures thereof.

10. The process of claim 9 wherein the promoter ion is K.

11. The process of claim 1 wherein the catalyst further contains a coordination ligand.

12. The process as described in claim 1 wherein the hydrogenating agent is molecular hydrogen.

13. The process of claim 12 wherein the consumed amount of molecular hydrogen to dihalopropanal is at least about 0.75:

1.

14. The process of claim 12 which is carried out with a hydrogen partial pressure of at least about 14 psia.

15. The process of claim 1 wherein the 2,3-dihalopropanal is selected from the group consisting of 2,3-dichloropropanal;

2,3-dibromopropanal;

2,3-dicholoro-2-methylpropanal 2,3-dibromo-2-methylpropanal; and

mixtures thereof.

16. The process of claim 1 wherein the 2,3-dihalopropanal is unsubstituted 2,3-dichloropropanal and the 2,3-dihalopropanol formed is 2,3-dichloropropanol.

17. The process of claim 1 wherein the 2,3-dihalopropanal is unsubstituted 2,3-dibromopropanal and the 2,3-dihalopropanol formed is 2,3-dibromopropanol.

18. The process of claim 1 which is carried out at a temperature of about 0°

C. to about 200°

C.

19. The process of claim 1 wherein the reaction mixture further contains a solvent.

20. The process of claim 19 wherein the solvent is selected from the group consisting of water, carboxylic acids, phenolic compounds, aliphatic alcohols, aliphatic and aromatic hydrocarbons, carbonates, ethers, glymes, glycol ethers, halogenated hydrocarbons and mixtures thereof.

21. The process of claim 1 wherein the reaction mixture further contains an acid scavenger.

22. The process of claim 21 wherein the acid scavenger is selected from the group consisting of alkali metal carbonates;

alkali metal bicarbonates;

alkali metal carboxylates;

ammonium and phosphonium carboxylates, bicarbonates, carbonates;

epoxides and mixtures thereof.

23. The process of claim 22 wherein the acid scavenger is epichlorohydrin.

24. The process of claim 1 comprising the step of reacting 2,3-dihalopropanal with at least a stoichiometric quantity of molecular hydrogen in the presence of the mixed transition metal catalyst and a solvent.

25. A process to make epihalohydrin comprising the steps of:

(a) reducing 2,3-dihalopropanal as described in claim 1 to form 2,3-dihalopropanol; and

(b) contacting the 2,3-dihalopropanol with a base, whereby an epihalohydrin is formed.

26. A process to make epihalohydrin comprising the steps of:

(a) halogenating acrolein to make 2,3-dihalopropanal;

(b) reducing 2,3-dihalopropanal as described in claim 1 to form 2,3-dihalopropanol; and

(c) contacting the 2,3-dihalopropanol with a base, whereby an epihalohydrin is formed.

27. A process to make epihalohydrin comprising the steps of:

(a) reacting a hydrocarbon which contains 3 carbon atoms with an oxidizing agent to form acrolein;

(b) reacting acrolein with a molecular halogen to form 2,3-dihalopropanal;

(c) reducing 2,3-dihalopropanal to form 2,3-dihalopropanol as described in claim 1 to form 2,3-dihalopropanol; and

(d) contacting the 2,3-dihalopropanol with a base, whereby an epihalohydrin is formed.