Method to selectively remove safrole from nutmeg oil

• US 7,985,818 B2
• Filed: 04/10/2006
• Issued: 07/26/2011
• Est. Priority Date: 04/10/2006
• Status: Active Grant

• Current Assignee: R J Reynolds Tobacco Company (R. J. Reynolds Tobacco)
• Original Assignee: R J Reynolds Tobacco Company (R. J. Reynolds Tobacco)
• Inventors: Pertsovich, Svetlana I.
• Primary Examiner(s): Lipman; Bernard
• Application Number:
  US12/296,468
• Publication Number:
  US 20100239726A1
• Time in Patent Office: 1,933 Days
• Field of Search: 526/199, 526/200, 526/201, 526/215, 526/243, 526/317.1, 526/318.43, 526/323.2, 526/326, 424/728, 424/769, 514/26
• US Class Current: 526/199
• CPC Class Codes: B01D 15/3852 using imprinted phases or molecular recognition; using imprinted phases
• CPC Class Codes: B01J 20/26 Synthetic macromolecular compounds
• CPC Class Codes: B01J 20/268 Polymers created by use of a template, e.g. molecularly imprinted polymers
• CPC Class Codes: B01J 20/285 based on polymers

Abstract

Methods for removing safrole from a sample, molecular imprinted copolymers that bind safrole, and methods of making the same are provided.

Claims

1. A method of preparing substantially safrole free nutmeg essential oil comprising the steps of:

providing at least one monomer, wherein the monomer is acrylamide;

providing a template molecule, wherein the template molecule is purified dihydrosafrole;

co-polymerizing the at least one monomer in the presence of a crosslinking agent and in the presence of the template molecule to form a co-polymerized composition;

substantially removing dihydrosafrole from the co-polymerized composition to form a molecularly imprinted co-polymer;

providing nutmeg essential oil comprising safrole; and

contacting the molecularly imprinted co-polymer with the nutmeg essential oil comprising safrole to bind the safrole to the molecularly imprinted co-polymer and form substantially safrole free nutmeg essential oil.

2. The method of claim 1 further comprising the steps of:

separating the substantially safrole free nutmeg essential oil from the molecularly imprinted co-polymer.

3. The method of claim 2, wherein the co-polymerizing is done the presence of an initiator, wherein the initiator is 2,2-azobis(isobutyronitrile);

and

wherein the crosslinking agent is ethylene glycol dimethacrylate.

4. The method of claim 3, wherein substantially removing dihydrosafrole from the co-polymerized composition comprises:

crushing the co-polymerized composition to form a crushed co-polymerized composition;

contacting the crushed co-polymerized composition with a first solvent; and

separating the solvent from the crushed co-polymerized composition to form the molecularly imprinted co-polymer.

5. The method of claim 4, wherein the first solvent comprises about at least 90% by weight ethanol.

6. A method for removing safrole, dihydrosafrole, or isosafrole from a sample, comprising the steps of:

providing at least one monomer comprising an alkenyl group having at least one pendent group comprising a functional group selected from the group consisting of an amide, a carboxylic acid, a sulfonic acid, and a phosphonic acid;

providing a template molecule, wherein the template molecule is purified dihydrosafrole;

co-polymerizing the at least one monomer in the presence of a crosslinking agent, an initiator, and the template molecule to form a co-polymerized composition;

substantially removing dihydrosafrole from the co-polymerized composition to form a molecularly imprinted co-polymer;

providing a sample comprising a recognition molecule selected from the group consisting of safrole, dihydrosafrole, and isosafrole; and

contacting the molecularly imprinted co-polymer with the sample to bind the recognition molecule to the molecularly imprinted co-polymer.

7. The method of claim 6, wherein the at least one monomer comprises an alkenyl group having a pendent group comprising an amide functional group.

8. The method of claim 7, wherein substantially removing dihydrosafrole from the co-polymerized composition comprises:

crushing the co-polymerized composition to form a crushed co-polymerized composition;

contacting the crushed co-polymerized composition with a first solvent; and

separating the solvent from the crushed co-polymerized composition to form the molecularly imprinted co-polymer.

9. The method of claim 8, wherein the monomer is acrylamide, the crosslinking agent is ethylene glycol dimethacrylate, and the initiator is 2,2-azobis(isobutyronitrile).

10. A molecularly imprinted co-polymer prepared by the steps of:

co-polymerizing at least one monomer in the presence of a crosslinking agent, an initiator, and a template molecule to form a co-polymerized composition;

the template molecule comprising purified dihydrosafrole, and the at least one monomer comprising an alkenyl group having at least one pendent group comprising a functional group selected from the group consisting of an amide, a carboxylic acid, a sulfonic acid, and a phosphonic acid; and

substantially removing dihydrosafrole from the co-polymerized composition to form the molecularly imprinted co-polymer.

11. The molecularly imprinted co-polymer according to claim 10, wherein the monomer is acrylamide, the crosslinking agent is ethylene glycol dimethacrylate, and the initiator is 2,2-azobis(isobutyronitrile).

12. The molecularly imprinted co-polymer according to claim 11, wherein substantially removing dihydrosafrole comprises:

crushing the co-polymerized composition to form a crushed co-polymerized composition;

contacting the crushed co-polymerized composition with a solvent, wherein the solvent comprises at least about 90% ethanol; and

separating the solvent from the crushed co-polymerized composition.

13. A method of preparing a molecularly imprinted co-polymer comprising:

co-polymerizing at least one monomer in the presence of a crosslinking agent, an initiator, and a template molecule to form a co-polymerized composition;

wherein the template molecule is purified dihydrosafrole;

wherein the at least one monomer comprises an alkenyl group having at least one pendent group comprising a functional group selected from the group consisting of an amide, a carboxylic acid, a sulfonic acid, and a phosphonic acid; and

substantially removing dihydrosafrole from the co-polymerized composition to form the molecularly imprinted co-polymer.

14. The method of claim 13, wherein the monomer comprises an alkenyl group having at least one pendent group comprising an amido functional group.

15. The method of claim 14, wherein the monomer is acrylamide.

16. The method of claim 15, wherein the crosslinking agent is ethylene glycol dimethacrylate.

17. The method of claim 16, wherein the initiator is 2,2-azobis(isobutyronitrile).

18. The method of claim 17, wherein the co-polymerizing is performed between about 50 and 70°

C.; and

wherein the co-polymerizing is performed in a solvent, wherein the solvent comprises at least about 90% ethanol.

19. The method of claim 18, wherein substantially removing dihydrosafrole comprises:

crushing the co-polymerized composition to form a crushed co-polymerized composition;

contacting the crushed co-polymerized composition with a solvent, wherein the solvent comprises at least about 90% ethanol; and

separating the solvent from the crushed co-polymerized composition to form the molecularly imprinted co-polymer.

20. The method of claim 19, further comprising drying the molecularly imprinted co-polymer at between about 50 and about 70°

C.