Claims
- 1. A method for increasing selectivity and productivity of a cumene process of phenol and acetone production comprising the steps of:
(a) treating, in a conversion reactor, organic cumene oxidation products containing from about 16 wt % to about 94 wt % cumene hydroperoxide, cumene, and by-products comprising at least dimethylbenzene alcohol and aldehydes, with the use of a hydrogen peroxide in a mutually insoluble organic and aqueous phase system of an aqueous hydrogen peroxide solution and an organic solution of said cumene oxidation products; and (b) mixing said organic phase cumene oxidation products with the aqueous phase hydrogen peroxide solution by use of a mixing device disposed within said conversion reactor, such that dimethylbenzene alcohol and said aldehydes are subject to a heterophase oxidation reaction with hydrogen peroxide so that dimethylbenzene alcohol is oxidized into cumene hydroperoxide and said aldehydes are oxidized into corresponding organic acids.
- 2. The method of claim 1, wherein hydrogen peroxide concentration in said aqueous solution of hydrogen peroxide is selected from a range of: from about 1% to about 70%, further comprising the step of:
(c) maintaining said selected hydrogen peroxide concentration at a substantially stable value.
- 3. The method of claim 2, wherein said step (c) comprises the step of:
(d) adding additional hydrogen peroxide aqueous solution into said conversion reactor, said additional hydrogen peroxide aqueous solution having a sufficient hydrogen peroxide concentration sufficient to maintain said selected hydrogen peroxide concentration in said conversion reactor.
- 4. The method of claim 2, wherein said step (c) further comprises the step of:
(e) feeding a hydrogen peroxide stabilizing agent into said conversion reactor to maintain said selected hydrogen peroxide concentration in said conversion reactor.
- 5. The method of claim 1, further comprising the step of:
(f) feeding an acidic catalyst into said conversion reactor to accelerate said oxidation reaction at said step (b).
- 6. The method of claim 5, wherein said acidic catalyst comprises at least one acid selected from at least the following acids:
1) weak organic acids, comprising at least formic, acetic, propionic, benzoic acids, and 2) acids of average strength, comprising at least fluorine, chlorine substituted acids of aliphatic range, mono-di-trichloracidic acids or their mixtures, mineral acids including at least H3PO4, H2SO4, HCl, HClO4, H2SO3, SO2, heterogeneous acidic catalysts including sulfanic ion exchange resins, naphiones, and acidic zeolites.
- 7. The method of claim 2, wherein said step (c) comprises the step of:
(g) adding a stabilizing catalytic agent to said conversion reactor to maintain said elected hydrogen peroxide concentration at a substantially stable value, and to provide an acidic catalyst for said oxidation reaction.
- 8. The method of claim 7, wherein said stabilizing catalytic agent is aqueous phosphoric acid.
- 9. The method of claim 8, wherein said aqueous phosphoric acid is maintained at a concentration from about 0.1 wt % to about 0.5 wt % of said aqueous hydrogen peroxide phase.
- 10. The method of claim 1, further comprising the step of:
(h) maintaining the weight ratio of said aqueous and organic phases in said conversion reactor within the range of about 0.1:1 to about 10:1
- 11. The method of claim 1, wherein said organic phase and aqueous phase containing hydrogen peroxide contact at a temperature of about 40° C. to about 75° C.
- 12. The method of claim 1, further comprising the step of:
(i) separating said oxidized organic products in said organic phase after contacting with hydrogen peroxide from said aqueous hydrogen peroxide phase at a phase separation stage, wherein said oxidized organic products contain less than 0.2 wt % of dimethylbenzene alcohol.
- 13. The method of claim 12, further comprising the step of:
(j) delivering said oxidized organic products to an evaporator to evaporate hydrogen peroxide therefrom under vacuum.
- 14. The method of claim 13, further comprising the steps of:
(k) concentrating said evaporated hydrogen peroxide in a fractionation column to produce water and aqueous hydrogen peroxide; (l) recycling said aqueous hydrogen peroxide to said conversion reactor; and (m) removing water from said fractionation column.
- 15. The method of claim 13, further comprising the step of:
(n) concentrating said oxidized organic products in a cumene hydroperoxide concentration stage to produce technical cumene hydroperoxide and by-products.
- 16. The method of claim 15, further comprising the steps of:
(o) directing said technical cumene hydroperoxide and by-products to a cumene hydroperoxide cleavage stage to produce output products containing at least phenol and acetone; (p) adding an acidic catalyst to said cumene hydroperoxide cleavage stage to accelerate said step (o) cleavage process; and (q) directing said output products to a neutralization stage to neutralize said acidic catalyst added at said step (p).
- 17. The method of claim 16, further comprising the step of:
(r) directing said neutralized output products, from said step (q) to a cumene hydroperoxide cleavage products fractionation stage to extract product phenol and acetone therefrom.
- 18. The method of claim 17, wherein said step (r) further comprises the steps of:
(s) directing said neutralized output products from said step (q) to an acetone and phenol fractionation column having a top and a bottom; and (t) delivering an acetone stream from said top of said acetone and phenol fractionation column to an acetone product column to extract final product acetone from a top of said acetone product column.
- 19. The method of claim 18, further comprising the steps of:
(u) delivering an acetone by-product stream from a bottom of said acetone product column to a phase separator vessel to separate cumene and by-products from an aqueous phase in said acetone by-product stream; (v) removing said aqueous phase from a bottom of said phase separator vessel; and (w) removing said cumene and said by-products from a top of said phase separator vessel.
- 20. The method of claim 19, further comprising the steps of:
(x) prior to said step (a), oxidizing cumene with air oxygen in an oxidation reactor to produce organic cumene oxidation products containing from about 16 wt % to about 45 wt % cumene hydroperoxide, cumene, and by-products comprising at least dimethylbenzene alcohol and aldehydes; and (y) delivering said cumene and by-products from said step (w) to said oxidation reactor.
- 21. The method of claim 20, further comprising the step of:
(z) after said step (y) and before said step (a), concentrating said organic cumene oxidation products in a concentration stage to produce organic cumene oxidation products containing from about 60 wt % to about 94 wt % cumene hydroperoxide and by-products comprising at least dimethylbenzene alcohol and aldehydes.
- 22. The method of claim 18, further comprising the steps of:
(aa) delivering a phenol stream from said bottom of said acetone and phenol fractionation column to a phenol column to perform fractionation of heavy products; and (bb) removing a bottom product containing at least phenol and acetophenone from a bottom of said phenol column to a phenol reclaiming stage.
- 23. The method of claim 22, further comprising the steps of:
(cc) delivering a crude phenol and trace by-products stream from a top of said phenol column to a catalytic treatment stage to produce treated phenol; (dd) delivering said treated phenol to a phenol finishing column to extract final product phenol therefrom; and (ee) removing said final product phenol from a side of said phenol finishing column.
- 24. The method of claim 12, further comprising the steps of:
(ff) recycling said separated unconverted hydrogen peroxide from said aqueous hydrogen peroxide phase to said conversion reactor.
- 25. The method of claim 1, wherein said aldehydes comprise at least: aliphatic C1-C3 aldehydes, and benzoic aldehyde, and wherein said cumene oxidation products further comprise acetophenone and dicumylperoxide.
- 26. A method for increasing selectivity and productivity of a cumene process of phenol and acetone production comprising the steps of:
(a) treating, in a conversion reactor, organic cumene oxidation products containing from about 16 wt % to about 94 wt % cumene hydroperoxide, cumene, and by-products comprising at least dimethylbenzene alcohol and aldehydes, with the use of a hydrogen peroxide in a mutually insoluble organic and aqueous phase system of an aqueous hydrogen peroxide solution and an organic solution of said cumene oxidation products; (b) maintaining hydrogen peroxide concentration at a substantially stable value selected from a range of about 20 wt % to about 50 wt %; and (c) mixing said organic phase cumene oxidation products with the aqueous phase hydrogen peroxide solution by use of a mixing device disposed within said conversion reactor, such that dimethylbenzene alcohol and said aldehydes are subject to a heterophase oxidation reaction with hydrogen peroxide so that dimethylbenzene alcohol is oxidized into cumene hydroperoxide and said aldehydes are oxidized into corresponding organic acids.
- 27. The method of claim 26, further comprising the step of:
(d) maintaining the weight ratio of said aqueous and organic phases in said conversion reactor within the range of about 1:1 to about 6:1
- 28. The method of claim 26, wherein said organic phase and aqueous phase containing hydrogen peroxide contact at a temperature of about 40° C. to about 75° C.
- 29. A method for increasing selectivity and productivity of a cumene process of phenol and acetone production comprising the steps of:
(a) treating, in a conversion reactor, organic cumene oxidation products containing from about 16 wt % to about 94 wt % cumene hydroperoxide, cumene, and by-products comprising at least dimethylbenzene alcohol and aldehydes, with the use of a hydrogen peroxide in a mutually insoluble organic and aqueous phase system of an aqueous hydrogen peroxide solution and an organic solution of said cumene oxidation products; (b) feeding an acidic catalyst into said conversion reactor; and (c) in the presence of said acidic catalyst, mixing said organic phase cumene oxidation products with the aqueous phase hydrogen peroxide solution by use of a mixing device disposed within said conversion reactor, such that dimethylbenzene alcohol and said aldehydes are subject to a heterophase oxidation reaction with hydrogen peroxide so that dimethylbenzene alcohol is oxidized into cumene hydroperoxide and said aldehydes are oxidized into corresponding organic acids.
- 30. A method for increasing selectivity and productivity of a cumene process of phenol and acetone production comprising the steps of:
(a) oxidizing cumene with air oxygen in an oxidation reactor to produce organic cumene oxidation products containing from about 16 wt % to about 45 wt % cumene hydroperoxide, cumene, and by-products comprising at least dimethylbenzene alcohol and aidehydes; (b) concentrating said organic cumene oxidation products in a concentration stage to produce concentrated organic cumene oxidation products containing from about 60 wt % to about 94 wt % cumene hydroperoxide and by-products comprising at least dimethylbenzene alcohol and aldehydes; (c) treating said concentrated organic cumene oxidation products in a conversion reactor, with the use of a hydrogen peroxide in a mutually insoluble organic and aqueous phase system of an aqueous hydrogen peroxide solution and an organic solution of said concentrated cumene oxidation products; and (d) mixing said organic phase concentrated cumene oxidation products with the aqueous phase hydrogen peroxide solution by use of a mixing device disposed within said conversion reactor, such that dimethylbenzene alcohol and said aldehydes are subject to a heterophase oxidation reaction with hydrogen peroxide so that dimethylbenzene alcohol is oxidized into cumene hydroperoxide and said aldehydes are oxidized into corresponding organic acids.
- 31. The method of claim 30, wherein hydrogen peroxide concentration in said aqueous solution of hydrogen peroxide is selected from a range of: from about 20% to about 50%, further comprising the step of:
(e) maintaining said selected hydrogen peroxide concentration at a substantially stable value.
- 32. The method of claim 31, wherein said step (e) comprises the step of:
(f) adding additional hydrogen peroxide aqueous solution into said conversion reactor, said additional hydrogen peroxide aqueous solution having a sufficient hydrogen peroxide concentration sufficient to maintain said selected hydrogen peroxide concentration in said conversion reactor.
- 33. The method of claim 31, wherein said step (e) further comprises the step of:
(g) feeding a hydrogen peroxide stabilizing agent into said conversion reactor to maintain said selected hydrogen peroxide concentration in said conversion reactor.
- 34. The method of claim 30, further comprising the step of:
(h) feeding an acidic catalyst into said conversion reactor to accelerate said oxidation reaction at said step (c).
- 35. The method of claim 31, wherein said step (e) comprises the step of:
(i) adding a stabilizing catalytic agent to said conversion reactor to maintain said selected hydrogen peroxide concentration at a substantially stable value, and to provide an acidic catalyst for said oxidation reaction.
- 36. The method of claim 35, wherein said stabilizing catalytic agent is aqueous phosphoric acid maintained at a concentration from about 0.1 wt % to about 0.5 wt % of said aqueous hydrogen peroxide phase.
- 37. The method of claim 30, further comprising the step of:
(j) maintaining the weight ratio of said aqueous and organic phases in said conversion reactor within the range of about 1:1 to about 6:1.
- 38. The method of claim 30, wherein said organic phase and aqueous phase containing hydrogen peroxide contact at a temperature of about 40° C. to about 75° C.
- 39. The method of claim 30, further comprising the step of:
(k) separating said oxidized organic products in said organic phase after contacting with hydrogen peroxide from said aqueous hydrogen peroxide phase at a phase separation stage, wherein said oxidized organic products contain less than 0.2 wt % of dimethylbenzene alcohol.
- 40. The method of claim 39, further comprising the step of:
(l) delivering said oxidized organic products to an evaporator to evaporate hydrogen peroxide therefrom under vacuum, such that only technical cumene hydroperoxide and by-products remain.
- 41. The method of claim 40, further comprising the steps of:
(m) concentrating said evaporated hydrogen peroxide in a fractionation column to produce water and aqueous hydrogen peroxide; (n) recycling said aqueous hydrogen peroxide to said conversion reactor; and (o) removing water from said fractionation column.
- 42. The method of claim 40, further comprising the steps of:
(p) directing said technical cumene hydroperoxide and by-products to a cumene hydroperoxide cleavage stage to produce output products containing at least phenol and acetone; (q) adding an acidic catalyst to said cumene hydroperoxide cleavage stage to accelerate said step (p) cleavage process; and (r) directing said output products to a neutralization stage to neutralize said acidic catalyst added at said step (q).
- 43. The method of claim 42, further comprising the steps of:
(s) directing said neutralized output products, from said step (r) to a cumene hydroperoxide cleavage products fractionation stage to extract product phenol and acetone therefrom.
- 44. The method of claim 39, further comprising the steps of:
(t) recycling said separated unconverted hydrogen peroxide from said aqueous hydrogen peroxide phase to said conversion reactor.
- 45. The method of claim 43, wherein said step (s) further comprises the steps of:
(u) directing said neutralized output products from said step (r) to an acetone and phenol fractionation column having a top and a bottom; and (v) delivering an acetone stream from said top of said acetone and phenol fractionation column to an acetone product column to extract final product acetone from a top of said acetone product column.
- 46. The method of claim 45, further comprising the steps of:
(w) delivering an acetone by-product stream from a bottom of said acetone product column to a phase separator vessel to separate cumene and by-products from an aqueous phase in said acetone by-product stream; (x) removing said aqueous phase from a bottom of said phase separator vessel; and (y) removing said cumene and said by-products from a top of said phase separator vessel.
- 47. The method of claim 46, further comprising the step of:
(z) delivering said cumene and by-products from said step (y) to said oxidation reactor.
- 48. The method of claim 45, further comprising the steps of:
(aa) delivering a phenol stream from said bottom of said acetone and phenol fractionation column to a phenol column to perform fractionation of heavy products; and (bb) removing a bottom product containing at least phenol and acetophenone from a bottom of said phenol column to a phenol reclaiming stage.
- 49. The method of claim 48, further comprising the steps of:
(cc) delivering a crude phenol and trace by-products stream from a top of said phenol column to a catalytic treatment stage to produce treated phenol; (dd) delivering said treated phenol to a phenol finishing column to extract final product phenol therefrom; and (ee) removing said final product phenol from a side of said phenol finishing column.
- 50. The method of claim 30, wherein said aldehydes comprise at least: aliphatic C1-C3 aldehydes, and benzoic aldehyde, and wherein said cumene oxidation products further comprise acetophenone and dicumylperoxide.
RELATED APPLICATIONS
[0001] This application claims priority from U.S. Provisional Patent Application Ser. No. 60/186,923 entitled “High Selective Method of Producing Cumene Hydroperoxide in a Phenol and Acetone Production Process” which was filed on Mar. 3, 2000, and from U.S. Provisional Patent Application Ser. No. 60/243,443 entitled “Improved High Selective Method of Producing Cumene Hydroperoxide in a Phenol and Acetone Production Process” which was filed on Oct. 26, 2000.
Provisional Applications (2)
|
Number |
Date |
Country |
|
60186923 |
Mar 2000 |
US |
|
60243443 |
Oct 2000 |
US |