System and process for producing an oxirane

• US 9,498,762 B2
• Filed: 02/03/2012
• Issued: 11/22/2016
• Est. Priority Date: 02/04/2011
• Status: Active Grant

• Current Assignee: Blue Cube IP LLC (OLIN Corporation)
• Original Assignee: Blue Cube IP LLC (OLIN Corporation)
• Inventors: Forlin, Anna, Carlberg, Philip J., Crampton, Hannah L., Pedernera, Esteban, Meza, Cesar E.
• Primary Examiner(s): Seifu, Lessanework
• Application Number:
  US13/983,361
• Publication Number:
  US 20130302216A1
• Time in Patent Office: 1,754 Days
• US Class Current: 1/1
• CPC Class Codes: B01D 11/0488 Flow sheets
• CPC Class Codes: B01D 11/0492 Applications, solvents used
• CPC Class Codes: B01J 19/00 Chemical, physical or physico-chemical processes in general; Their relevant apparatus
• CPC Class Codes: B01J 2219/00247 Fouling of the reactor or the process equipment
• CPC Class Codes: B01J 8/0278 Feeding reactive fluids for solid material B01J8/0015
• CPC Class Codes: B01J 8/20 with liquid as a fluidising medium
• CPC Class Codes: C07D 301/12 with hydrogen peroxide or inorganic peroxides or peracids
• CPC Class Codes: C07D 301/32 Separation; Purification
• CPC Class Codes: Y02P 20/52 using catalysts, e.g. selective catalysts

Abstract

Embodiments of the present disclosure are directed to a system and a process for producing an oxirane. For the various embodiments, the system and process of the present disclosure includes: a reaction vessel having a reaction mixture of an olefin, a peroxide compound, a solvent mixture with an alcohol and a non-reactive co-solvent, a solid phase, and reaction products of the reaction mixture, where the reaction products include an oxirane; a separation vessel coupled to the reaction vessel, where an effluent of the reaction mixture and reaction products from the reaction vessel separates in the separation vessel into a liquid aqueous phase and a liquid organic phase; and an extraction vessel coupled to an outlet of the separation vessel, where the liquid aqueous phase taken from the outlet of the separation vessel mixes with an extraction solvent to extract oxirane from the aqueous phase.

Claims

1. A system, comprising:

a reaction vessel having a multiple liquid phase reaction mixture of an olefin, a peroxide compound, a solvent mixture with an alcohol and a non-reactive co-solvent, a solid phase, and reaction products of the reaction mixture, where the reaction products include an oxirane;

an exchange vessel holding a solid support with active sites to bind iron ions, the exchange vessel having an inlet that carries an organic stream including the olefin and iron ions, where the active sites on the solid support remove iron ions from the organic stream to provide an iron ion concentration of less than one weight percent based on the total weight of the organic stream, and where the exchange vessel has an outlet that connects to the reaction vessel that receives the organic stream having the olefin and the iron ion concentration of less than one weight percent;

a separation vessel having a first outlet, wherein the separation vessel is coupled to the reaction vessel, where an effluent of the multiple liquid phase reaction mixture and reaction products from the reaction vessel separates in the separation vessel into a liquid aqueous phase and a liquid organic phase; and

an extraction vessel comprising an extraction solvent capable of extracting oxirane from the liquid aqueous phase, the extraction vessel coupled to the first outlet of the separation vessel, wherein the liquid aqueous phase taken from the outlet of the separation vessel mixes with the extraction solvent to extract oxirane from the liquid aqueous phase.

2. The system of claim 1, where the solid phase has an affinity for the liquid aqueous phase, and where both the liquid aqueous phase and the solid phase form a slurry that is taken from the outlet of the separation vessel and mixes with the extraction solvent to extract at least the oxirane from the liquid aqueous phase.

3. The system of claim 1, wherein the extraction solvent i-sand the non-reactive co-solvent are both 1,2-dichlorobenzene.

4. The system of claim 1, where the solid phase includes a polar group, a charged group or a combination thereof.

5. The system of claim 1, where the active sites of the solid support are represented by the following formula I:

6. The system of claim 1, where the iron ion concentration of the organic stream after removing the iron ions is less than one part per million of the organic stream.

7. The system of claim 1, wherein the solid phase is a titanium silicalite catalyst fouled during a reaction between the olefin and the peroxide compound to produce the oxirane, the system further comprising a regeneration solution in contact with the solid phase, wherein the regeneration solution has an organic compound and an oxidizing agent, the oxidizing agent having a concentration of 0.1 to 50 weight percent based on a total weight of the regeneration solution, exclusive of the solid phase, and wherein the regeneration solution regenerates a first part of the solid phase suspended in the liquid phase with the proviso that the regenerates does not include washing in addition to contact with the regeneration solution to regenerate the solid phase.

8. The system of claim 7, where the oxidizing agent is selected from the group consisting of hydrogen peroxide, ozone, organic peroxide compounds, inorganic peroxide compounds, and combinations thereof.

9. The system of claim 1, where the extraction vessel includes a first outlet through which the extraction solvent with the oxirane and olefin return to the reaction mixture in the reaction vessel.

10. The system of claim 1, further including a distillation unit operation, where the extraction vessel includes a second outlet through which the extraction solvent with the oxirane is transported to the distillation unit operation.

11. The system of claim 1, where the separation vessel includes a second outlet to remove the liquid organic phase from the separation vessel, the second outlet coupled to a distillation unit operation that separates oxirane from a remainder of the liquid organic phase, where the remainder of the liquid organic phase returns to the reaction mixture in the reaction vessel.

12. The system of claim 1, where the oxirane is epichlorohydrin, the olefin is allyl chloride, and the peroxide compound is a hydrogen peroxide solution.