WO2005104774B1 - Method of preparing alkoxylation catalysts and their use in alkoxylation processes - Google Patents

Method of preparing alkoxylation catalysts and their use in alkoxylation processes

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Publication number
WO2005104774B1
WO2005104774B1 PCT/US2005/014562 US2005014562W WO2005104774B1 WO 2005104774 B1 WO2005104774 B1 WO 2005104774B1 US 2005014562 W US2005014562 W US 2005014562W WO 2005104774 B1 WO2005104774 B1 WO 2005104774B1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
pentanol
butanol
acid
dimethyl
Prior art date
Application number
PCT/US2005/014562
Other languages
French (fr)
Other versions
WO2005104774A3 (en
WO2005104774A2 (en
Filing date
Publication date
Priority claimed from US10/832,613 external-priority patent/US7119236B2/en
Application filed filed Critical
Priority to EP05740203.4A priority Critical patent/EP1747183B1/en
Priority to CN200580021529.0A priority patent/CN1976887B/en
Priority to PL05740203T priority patent/PL1747183T3/en
Publication of WO2005104774A2 publication Critical patent/WO2005104774A2/en
Publication of WO2005104774A3 publication Critical patent/WO2005104774A3/en
Publication of WO2005104774B1 publication Critical patent/WO2005104774B1/en

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Abstract

A process for preparing an alkoxylation catalyst suitable for alkoxylating compounds that includes mixing a calcium-containing compound in a dispersing medium having a boiling point less that 160 °C with a carboxylic acid and an inorganic acid or anhydride.

Claims

25AMENDED CLAIMS received by the International Bureau on 23 February 2006What is claimed and desired to be secured by Letters Patent is as follows:
1. A process for preparing an alkoxylation catalyst comprising: admixing a volatile dispersing medium consisting essentially of media having a boiling point less than 160 °C and comprised of one or more branched or straight chain alcohols, volatile esters, volatile ethers selected from the group consisting of dimethyl ether, diethyl ether, dimethoxy ethane, diethoxymethane, dibutylether, and isopropyl ether, or volatile aldehydes and ketones, a calcium-containing compound that is at least partially dispersible in said dispersing medium and a carboxylic acid or anhydride having from about 4 to about 15 carbon atoms, with the mole ratio of calcium to said carboxylic acid or anhydride being from about 15:1 to 1:1, to produce a calcium-containing composition.
2. The process according to claim 1, further comprising the step of adding an amount of an inorganic acid or anhydride to produce a partially neutralized calcium-containing catalyst.
3. The process of claim 2, wherein said inorganic acid or anhydride is selected from the group consisting of sulfuric acid, phosphoric acid, oleum, sulfur trioxide, and phosphorous pentoxide, or mixtures thereof.
4. The process according to claim 2, further comprising the step of adding an aluminum alkoxide to the calcium-containing composition.
5. The process of claim 2, including heating said partially neutralized composition at a temperature of from about 25 °C to about 160 0C under reflux conditions.
6. The process of claim 5, wherein said heating is conducted for a period of 1 to 5 hours.
7. The process of claim 1 , wherein said calcium-containing compound is selected from the group consisting of calcium hydride, calcium acetate, calcium oxalate, calcium oxide, calcium hydroxide, calcium lactate, calcium alkoxide, and mixtures thereof.
8. The process of claim 1, wherein said carboxylic acid is selected from the group consisting of octanoic acid, 2-methyl hexanoic acid, heptanoic acid, 3 -methyl octanoic acid, 4- ethyl nonanoic acid, 2-ethyl hexanoic acid, or mixtures thereof.
9. The process of claim 1, wherein said dispersing medium consists essentially of one or more branched or straight chain alcohols.
10. The process of claim 9, wherein said branched or straight chain alcohols are selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, 2-methyl-l-propanol, 2-methyl-2-propanol, 1-butanol, 2,3 -dimethyl- 1-butanol, 3, 3 -dimethyl- 1-butanol, 2-ethyl-l- butanol, 2-methyl- 1-butanol, 3 -methyl- 1-butanol, 2-butanol, 2-methyl-2-butanol, 2,3-dimethyl- 2-butanol, 3,3-dimethyl-2-butanol, 3-methyl-2-butanol, 2-methyl- 1-pentanol, 3-methyl-l- pentanol, 4-methyl- 1-pentanol, 2-pentanol, 2,4-dimethyl-2-pentanol, 2-methyl-2-pentanol, 3- methyl-2-pentanol, 4-methyl-2-pentanol, 3-pentanol, 2,4,4-trimethyl-2-pentanol, 2,2-dimethyl- 3-pentanol, 2,3-dimethyl-3-pentanol, 2,4-dimethyl-3-pentanol, 3-ethyl-3-pentanol, 3-ethyl-2- methyl-3-pentanol, 2-methyl-3-pentanol, 2,3,4-trimethyl-3-pentanol, 1-pentanol, 1-hexanol, 2- hexanol, 2-methyl-2-hexanol, 5-methyl-2-hexanol, 3-hexanol, and 3-methyl-3-hexanol.
11. The process of claim 9, wherein said branched or straight chain alcohols are selected from the group consisting of ethanol, 1-propanol, 2-propanol, 2-methyl-l-propanol, 1-butanol, 2,3 -dimethyl- 1-butanol, 3, 3 -dimethyl- 1-butanol, 2-ethyl- 1-butanol, 2-methyl- 1-butanol, 3- methyl- 1-butanol, 2-butanol, 3,3-dimethyl-2-butanol, 3-methyl-2-butanol, 2-methyl- 1- pentanol, 3 -methyl- 1-pentanol, 4-methyl- 1-pentanol, 2-pentanol, 3-methyl-2-pentanol, 4- methyl-2-pentanol, 3-pentanol, 2,2-dimethyl-3-pentanol, 2,4-dimethyl-3-pentanol, 2-methyl-3- pentanol, 1-pentanol, 1-hexanol, 2-hexanol, 5-methyl-2-hexanol, and 3-hexanol.
12. The process of claim 1, wherein said dispersing medium consists essentially of one or more volatile esters.
13. The process according to claim 12, wherein said ester is an ester of formic acid, acetic acid, propionic acid, or butyric acid.
14. The process according to claim 12, wherein said ester is selected from the group consisting of allyl formate, butyl formate, isobutyl formate, sec-butyl formate, ethyl formate, hexyl formate, methyl formate, pentyl formate, isopentyl formate, propyl formate, and isopropyl formate.
15. The process according to claim 12, wherein said ester is selected from the group consisting of allyl acetate, butyl acetate, iso-butyl acetate, sec-butyl acetate, tert-butyl acetate, ethyl acetate, methyl acetate, tert-amyl acetate, isopentyl acetate, 2-methyl-3-pentyl acetate, 3- methyl-3 -pentyl acetate, 4-methyl-2 -pentyl acetate, pentyl acetate, 2-pentyl acetate, 3-pentyl acetate, propyl acetate, isopropyl acetate, and 1,2,2-trimethyl propyl acetate. 27
16. The process according to claim 12, wherein said ester is selected from the group consisting of allyl propionate, butyl propionate, isobutyl propionate, sec-butyl propionate, ethyl propionate, propyl propionate, isopropyl propionate, and methyl propionate.
17. The process according to claim 12, wherein said ester is selected from the group consisting of sec-butyl butyrate, iso-butyl butyrate, tert-butyl butyrate, ethylbutyrate, ethyl-2- methyl butyrate, isopropyl-3 -methyl butyrate, ethyl iso valerate, methyl iso valerate, propyl isovalerate, propyl butyrate, and iso-propyl butyrate.
18. The process of claim 1 , wherein said dispersing medium consists essentially of one or more volatile ethers.
19. The process of claim 18, wherein said ether is selected from the group consisting of dimethyl ether, diethyl ether, dimethoxy ethane, diethoxymethane, dibutylether, and isopropyl ether.
20. The process of claim 1, wherein said dispersing medium consists essentially of one or more volatile aldehydes and ketones.
21. The process of claim 20, wherein said aldehydes and ketones are selected from the group consisting of acetaldehyde, propionaldehyde, butyraldehyde, hexanal, heptanal, acetone, butanone, pentanones, hexanones, and heptanones.
22. The process of claim 1, wherein said dispersing medium consists essentially of media having a boiling point less than 120 °C.
23. The process of claim 1 , wherein said dispersing medium consists essentially of media having a boiling point between about 80 0C and 140 0C.
24. The process of claim 3, further comprising the step of removing the volatile dispersing medium to generate an active catalyst in a solid form.
25. A process for preparing an alkoxylation catalyst comprising: admixing a volatile dispersing medium consisting of media having a boiling point less than 160 °C and comprised of one or more branched or straight chain alcohols, volatile esters, volatile ethers selected from the group consisting of dimethyl ether, diethyl ether, dimethoxy ethane, diethoxymethane, dibutylether, and isopropyl ether, or volatile aldehydes and ketones, a calcium-containing compound that is at least partially dispersible in said dispersing medium 28
and a carboxylic acid or anhydride having from about 4 to about 15 carbon atoms, the mole ratio of calcium to said carboxylic acid or anhydride being from about 15:1 to 1 :1, to produce a calcium-containing composition.
26. An alkoxylation process comprising: forming an alkoxylation catalyst by admixing a volatile dispersing medium having a boiling point below about 160 0C and comprised of one or more branched or straight chain alcohols, volatile esters, volatile ethers selected from the group consisting of dimethyl ether, diethyl ether, dimethoxy ethane, diethoxymethane, dibutylether, and isopropyl ether, or volatile aldehydes and ketones, a calcium-containing compound that is at least partially dispersible in said volatile dispersing medium, and a carboxylic acid or anhydride having from about 4 to about 15 carbon atoms, with the mole ratio of calcium to said carboxylic acid or anhydride being from about 15 : 1 to 1 : 1 , to produce a calcium-containing composition having titratable alkalinity; and adding an amount of inorganic acid or anhydride to produce a partially neutralized calcium-containing alkoxylation catalyst; and reacting, in the presence of said alkoxylation catalyst, a reactant selected from the group consisting of alcohols, phenols, esters, glycerides, carboxylic acids, amides, and amines and mixtures thereof and an alkylene oxide under alkoxylation conditions to produce an alkoxylated derivative of said reactant.
27. The process of claim 26, wherein said reaction occurs at a temperature greater than about 160 0C.
28. The process of claim 26, wherein said reactant is selected from the group consisting of methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol; octadecanol, isopropyl alcohol, sec-butanol, isobutanol, 2-pentanol, 3-pentanol, 2-ethylhexanol, isodecanol, cyclopentanol, cyclohexanol, cycloheptanol, cyclooctanol, benzyl alcohol, phenylethyl alcohol, phenylpropyl alcohol, and 2-butoxy ethanol.
29. The process of claim 26, wherein said reactant is selected from the group consisting of p-methylphenol, p-ethylphenol, p-butylphenol, p-heptylphenol, p-octylphenol, p-nonylphenol, dinonylphenol, p-decylphenol, and p-dodecylphenol. 29
30. The process of claim 26, wherein said reactant is selected from the group consisting of ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, neopentylene glycol, decylene glycol, diethylene glycol, Methylene glycol, and dipropylene glycol.
31. The process of claim 26, wherein said reactant is selected from the group consisting of glycerin, 1,3-propanediol, pentaerythritol, galactitol, sorbitol, mannitol, erythritol, trimethylolethane and trimethylolpropane.
32. The process of claim 26, wherein said reactant is selected from the group consisting of formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, benzoic acid, phenylacetic acid, toluic acid, and phthalic acid.
33. The process of claim 26, wherein said reactant is selected from the group consisting of N,N-diethylamine, N-ethylamine, N-butylamine, N-octylamine, N-decylamine, N- dodecylamine, diethanolamine, hexamethylenediamine, ethylenediamine, diethylenetriamine, and trietheylenetetraamine.
34. The process of claim 26, wherein said volatile dispersing media is the same as said reactant.
35. The process of claim 26, wherein said volatile dispersing media is removed prior to said reacting step.
36. The process of claim 26, wherein said reactant has a boiling point greater than the boiling point of said dispersing medium.
37. The process of claim 26, wherein the reactant has boiling point about 20 °C or more higher than the boiling point of said dispersing medium.
38. The process of claim 26, wherein said calcium-containing compound is selected from the group consisting of calcium hydride, calcium acetate, calcium oxalate, calcium oxide, calcium hydroxide, calcium lactate, calcium alkoxide, and mixtures thereof.
39. The process of claim 26, wherein said carboxylic acid is selected from the group consisting of octanoic acid, 2-methyl hexanoic acid, heptanoic acid, 3-methyl octanoic acid, 4- ethyl nonanoic acid, 2-ethyl hexanoic acid, or mixtures thereof. 30
40. The process of claim 26, wherein said inorganic acid or anhydride is selected from the group consisting of sulfuric acid, phosphoric acid, oleum, sulfur trioxide, and phosphorous pentoxide, or mixtures thereof.
41. The process of claim 26, wherein said dispersing medium consists essentially of one or more branched or straight chain alcohols.
42. The process of claim 41 , wherein said branched or straight chain alcohols are selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, 2-methyl-l-propanol, 2-methyl-2-propanol, 1-butanol, 2,3-dimethyl-l-butanol, 3,3-dimethyl-l-butanol, 2-ethyl-l- butanol, 2-methyl- 1-butanol, 3 -methyl- 1-butanol, 2-butanol, 2-methyl-2-butanol, 2,3-dimethyl- 2-butanol, 3,3-dimethyl-2-butanol, 3-methyl-2-butanol, 2-methyl- 1-pentanol, 3-methyl-l- pentanol, 4-methyl- 1-pentanol, 2-pentanol, 2,4-dimethyl-2-pentanol, 2-methyl-2-pentanol, 3- methyl-2-pentanol, 4-methyl-2-pentanol, 3-pentanol, 2,4,4-trimethyl-2-pentanol, 2,2-dimethyl- 3-pentanol, 2,3-dimethyl-3-pentanol, 2,4-dimethyl-3-pentanol, 3-ethyl-3-pentanol, 3-ethyl-2- methyl-3-pentanol, 2-methyl-3-pentanol, 2,3,4-trimethyl-3-pentanol, 1-pentanol, 1-hexanol, 2- hexanol, 2-methyl-2-hexanol, 5-methyl-2-hexanol, 3-hexanol, and 3-methyl-3-hexanol.
43. The process of claim 41, wherein said branched or straight chain alcohols are selected from the group consisting of ethanol, 1-propanol, 2-propanol, 2-methyl-l-propanol, 1-butanol, 2,3-dimethyl-l-butanol, 3,3-dimethyl-l-butanol, 2-ethyl- 1-butanol, 2-methyl- 1-butanol, 3- methyl- 1-butanol, 2-butanol, 3,3-dimethyl-2-butanol, 3-methyl-2-butanol, 2-methyl- 1- pentanol, 3 -methyl- 1-pentanol, 4-methyl- 1-pentanol, 2-pentanol, 3-methyl-2-pentanol, A- methyl-2-pentanol, 3-pentanol, 2,2-dimethyl-3-pentanol, 2,4-dimethyl-3-pentanol, 2-methyl-3- pentanol, 1-pentanol, 1-hexanol, 2-hexanol, 5-methyl-2-hexanol, and 3-hexanol.
44. The process of claim 26, wherein said dispersing medium consists essentially of one or more volatile esters.
45. The process according to claim 44, wherein said ester is an ester of formic acid, acetic acid, propionic acid, or butyric acid. 31
46. The process according to claim 45, wherein said ester is selected from the group consisting of allyl formate, butyl formate, isobutyl formate, sec-butyl formate, ethyl formate, hexyl formate, methyl formate, pentyl formate, isopentyl formate, propyl formate, and isopropyl formate.
47. The process according to claim 45, wherein said ester is selected from the group consisting of allyl acetate, butyl acetate, iso-butyl acetate, sec-butyl acetate, tert-butyl acetate, ethyl acetate, methyl acetate, tert-amyl acetate, isopentyl acetate, 2-methyl-3 -pentyl acetate, 3- methyl-3 -pentyl acetate, 4-methyl-2 -pentyl acetate, pentyl acetate, 2-pentyl acetate, 3 -pentyl acetate, propyl acetate, isopropyl acetate, and 1,2,2-trimethyl propyl acetate.
48. The process according to claim 45, wherein said ester is selected from the group consisting of allyl propionate, butyl propionate, isobutyl propionate, sec-butyl propionate, ethyl propionate, propyl propionate, isopropyl propionate, and methyl propionate.
49. The process according to claim 45, wherein said ester is selected from the group consisting of sec-butyl butyrate, iso-butyl butyrate, tert-butyl butryate, ethylbutyrate, ethyl-2- methyl butyrate, isopropyl-3 -methyl butyrate, ethyl iso valerate, methyl iso valerate, propyl isovalerate, propyl butyrate, and iso-propyl butyrate.
50. The process of claim 26, wherein said dispersing medium consists essentially of one or more volatile ethers.
51. The process of claim 50, wherein said ether is selected from the group consisting of dimethyl ether, diethyl ether, dimethoxy ethane, diethoxymethane, dibutylether, and isopropyl ether.
52. The process of claim 26, wherein said dispersing medium consists essentially of one or more volatile aldehydes and ketones.
53. The process of claim 52, wherein said aldehydes and ketones are selected from the group consisting of acetaldehyde, propionaldehyde, butyraldehyde, hexanal, heptanal, acetone, butanone, pentanones, hexanones, and heptanones.
54. The process of claim 26, wherein said dispersing medium consists essentially of media having a boiling point less than 120 0C. 32
55. The process of claim 26, wherein said dispersing medium consists essentially of media having a boiling point between about 80 0C and 140 °C.
PCT/US2005/014562 2004-04-27 2005-04-27 Method of preparing alkoxylation catalysts and their use in alkoxylation processes WO2005104774A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP05740203.4A EP1747183B1 (en) 2004-04-27 2005-04-27 Method of preparing alkoxylation catalysts and their use in alkoxylation processes
CN200580021529.0A CN1976887B (en) 2004-04-27 2005-04-27 Method of preparing alkoxylation catalysts and their use in alkoxylation processes
PL05740203T PL1747183T3 (en) 2004-04-27 2005-04-27 Method of preparing alkoxylation catalysts and their use in alkoxylation processes

Applications Claiming Priority (2)

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US10/832,613 2004-04-27
US10/832,613 US7119236B2 (en) 2004-04-27 2004-04-27 Method of preparing alkoxylation catalysts and their use in alkoxylation processes

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WO2005104774A3 WO2005104774A3 (en) 2006-02-16
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