Natural 1,2-alkanediols, compositions having natural 1,2-alkanediols and processes for making the same
A process is incorporated herein for the synthesis of bio-1,2-alkanediols, comprising: providing a bio-alkene having a carbon chain of about 5 to about 20 carbon atoms and a bio-1-alkene regioselectivity of at least about 80%, at least about 92% and/or at least about 95%; and converting the bio-alkene to a bio-1,2-alkanediol having a carbon chain length of about 5 to about 20 carbon atoms. Methods for treating catalysts which may be incorporated in the process for the synthesis of bio-1,2-alkanediols are also included herein. Such bio-1,2-alkanediols are used in compositions and products alone as antimicrobial materials, or with existing bio-compounds and/or antimicrobials, preservatives, alternative preservation systems and/or hurdle technology components. The bio-1,2-alkanediols incorporate a natural and bio-based pathway for antimicrobial effects in various compositions such as cosmetic, pharmaceutical, industrial and household products.
1. A process for the synthesis of bio-1,2-alkanediols, comprising:
providing a bio-alkene having a carbon chain of about 5 to about 20 carbon atoms and a bio-1-alkene regioselectivity of at least about 80%; and
converting the bio-alkene to a bio-1,2-alkanediol having a carbon chain length of about 5 to about 20 carbon atoms.
2. The process of claim 1 , wherein the bio-alkene and the bio-1,2-alkanediol each have a carbon chain of about 6 to about 14 carbon atoms.
3. The process according to claim 2 , wherein the bio-alkene and the bio-1,2-alkanediol each have a carbon chain length of about 6 to about 10 carbon atoms.
4. The process according to claim 3 , wherein the bio-alkene and the bio-1,2-alkanediol each have a carbon chain length of about 6 to about 8 carbon atoms.
5. The process according to claim 1 , wherein the bio-alkene is bio-octene and the bio-1,2-alkane diol is bio-1,2-octanediol.
6. The process according to claim 1 , wherein the bio-alkene results from a process wherein a bio-1-alcohol is dehydrated by heating the bio-1-alcohol in a reactor with a catalyst.
7. The process according to claim 6 , wherein the reactor is a fixed bed reactor.
8. The process according to claim 7 , wherein the fixed bed reactor is a fluidized fixed bed reactor.
9. The process according to claim 6 , wherein the catalyst is selected from ZnAl 2 O 4 and a γ-alumina catalyst.
10. The process according to claim 9 , wherein the bio-alkene has a bio-1-alkene regioselectivity of about 92% to about 99%.
11. The process according to claim 10 , wherein the bio-alkene have a bio-1-alkene regioselectivity of about 95% to about 99%.
12. The process according to claim 11 , wherein the process yields at least about 92% to about 99% of the bio-1,2-alkanediol.
13. The process according to claim 9 , wherein the catalyst is a γ-alumina catalyst is treated with a base to form a modified γ-alumina catalyst.
14. The process according to claim 13 , wherein the base comprises a Group I or a Group II metal.
15. The process according to claim 9 , wherein the γ-alumina catalyst is treated with a calcium promoter to provide a modified γ-alumina catalyst.
16. The process according to claim 15 , wherein the modified γ-alumina catalyst is calcined to provide a calcined γ-alumina catalyst.
17. The process according to claim 16 , wherein the calcium promoter is used in an amount of about 0.01 weight percent to about 4 weight percent based on the weight of CaO determined after calcination.
18. The process according to claim 17 , wherein the calcium promoter is used in an amount of about 1 weight percent to about 2 weight percent based on the weight of CaO determined after calcination.
19. The process according to claim 15 wherein a temperature during calcination is about 400° C. to about 500° C.
20. The process according to claim 19 , wherein the temperature during calcination is about 420° C. to about 480° C.
21. The process according to claim 20 , wherein the temperature during calcination is about 440° C. to about 460° C.
22. The process according to claim 15 , wherein calcination is carried out in an oven.
23. The process according to claim 15 , wherein the calcination is carried out in an atmosphere of air or inert gas.
24. The process according to claim 6 , wherein the bio-alkene undergoes a distillation step to refine the bio-alkene prior to converting the bio-alkene to the bio-1,2-alkanediol.
25. The process according to claim 6 , wherein the bio-1,2-alkanediol formed from the bio-alkene undergoes a final distillation step to refine the bio-1,2-alkanediol.
26. The process according to claim 1 , wherein the bio-alkene results from a process wherein the bio-1-alcohol in water is dehydrated by heating the bio-1-alcohol with a catalyst under a purge gas.
27. The process according to claim 1 , wherein the bio-alkene is converted to the bio-1,2-alkanediol by reacting the bio-alkene in the presence of at least one of formic acid or acetic acid and a peroxide to form a bio-1,2-epoxyalkane having an epoxy ring, and contacting the 1,2-epoxyalkane with water and sodium hydroxide to form the bio-1,2-alkanediol.
28. The process according to claim 1 , wherein the process yields at least about 60% to about 99% of the bio-1,2-alkanediol.
29. The process according to claim 28 , wherein the process yields at least about 72% to about 99% of the bio-1,2-alkanediol.
30. A process for making bio-1,2-alkanediols, comprising:
providing a bio-1-alcohol and a catalyst treated with a base;
dehydrating the bio-1-alcohol in the presence of the catalyst to form a bioalkene having a carbon chain of about 5 to about 20 carbon atoms and a bio-1-alkene regioselectivity of at least about 80%; and
converting the bio-alkene to a bio-1,2-alkanediol having a carbon chain length of about 5 to about 20 carbon atoms.
31. The process according to claim 30 , wherein the catalyst is a γ-alumina catalyst and the base comprises calcium.
32. The process according to claim 31 , wherein the γ-alumina catalyst is treated with a calcium promotor and after treatment is calcined at a temperature of about 400° C. to about 500° C.
33. The process according to claim 30 , wherein the process yields about 72% to about 99%/a of the bio-1,2-alkanediol.
34. The process according to claim 30 , wherein the bio-1-alkene regioselectivity is about 95% to about 99%.
35. The process of claim 1 , wherein the bio-alkene is converted to the bio-1,2-alkanediol having a carbon chain length of about 5 to about 20 carbon atoms by reacting the bio-alkene in the presence of at least one of a peracid and a hydroxide to form a reaction product, and contacting the reaction product with water and a base to form the bio-1,2-alkanediol.
36. The process according to claim 35 , wherein the bio-alkene is converted to the bio-1,2-alkanediol by reacting the bio-alkene in the presence of at least one of formic acid or acetic acid and a peroxide to form a bio-1,2-epoxyalkane having an epoxy ring, and contacting the 1,2-epoxyalkane with water and sodium hydroxide to form the bio-1,2-alkanediol.
37. The process according to claim 30 , wherein the bio-alkene is converted to the bio-1,2-alkanediol having a carbon chain length of about 5 to about 20 carbon atoms by reacting the bio-alkene in the presence of at least one of a peracid and a hydroxide to form a reaction product, and contacting the reaction product with water and a base to form the bio-1,2-alkanediol.
38. The process according to claim 37 , wherein the bio-alkene is converted to the bio-1,2-alkanediol by reacting the bio-alkene in the presence of at least one of formic acid or acetic acid and a peroxide to form a bio-1,2-epoxyalkane having an epoxy ring, and contacting the 1,2-epoxyalkane with water and sodium hydroxide to form the bio-1,2-alkanediol.