IP Library Granted Patent US 7,008,914
Granted Patent B2
US 7,008,914 · App. 10/263,547 · Granted Mar 7, 2006

Alkylbenzene detergents with high 2-isomer content

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Quick Facts
Patent No.
US 7,008,914
App. No.
10/263,547
Granted
Mar 7, 2006
Kind
B2
Abstract

This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of alkylbenzene (LAB) by alkylation of benzene with an olefin. The olefin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation. This invention is also directed to a process for production of LAB having a high 2-phenyl isomer content by use of the fluorine-containing mordenite in conjunction with a conventional solid LAB alkylation catalyst. The two catalysts may be used in a mixed catalyst bed or may be packed in series, with the relative proportions being adjusted to provide a desired 2-phenyl isomer content of in the final product.

Claims (137)

1. A composition of matter comprising alkylbenzenes, which are prepared according to a process comprising:

a) contacting benzene and an olefin having about 8 to about 30 carbons in the presence of a mixed catalyst bed to form alkylbenzenes, wherein the mixed catalyst bed comprises fluorine-containing mordenite and a second, solid alkylbenzene alkylation catalyst, wherein the second alkylation catalyst has a selectivity to the 2-phenyl isomer of the alkylbenzenes less than the selectivity of the fluorine-containing mordenite; and

b) wherein the mordenite has been treated by contacting the mordenite with an aqueous hydrogen fluoride solution, wherein the hydrogen fluoride in the aqueous solution has a concentration in the range from about 0.1 percent to about 1 percent by weight.

2. A process for producing an alkylbenzene sulfonic acid comprising the steps of:

a) providing a composition according to claim 1 ; and

b) sulfonating a composition according to claim 1 to form an alkylbenzene sulfonic acid product.

3. The alkylbenzene sulfonic acid product produced by a process according to claim 2 .

4. A process according to claim 2 further comprising: c) neutralizing the product of b) with a suitable alkaline substance containing one or more cations selected from the group consisting of: sodium, potassium, ammonium, magnesium and substituted ammonium alkalis, thus providing an alkylbenzene sulfonate surfactant.

5. The alkylbenzene sulfonate surfactant produced by the process of claim 4 .

6. A composition useful as a detergent for cleaning laundry, dishes, hard surfaces, and other substrates that is formed from components comprising:

a) an alkylbenzene sulfonate surfactant component produced by a process according to claim 4 present in any amount between 0.25% and 99.50% by weight based upon the total weight of the composition, said component characterized as comprising any amount between 30.00% and 82.00% by weight based upon the total weight of the component, including every hundredth percentage therebetween, of water-soluble sulfonates of the 2-phenyl isomers of alkylbenzenes described by the general formula:

wherein n is equal to any integer between 4 and 16; and

b) any amount between 99.75% and 0.50% of a second component that comprises at least one other component known to be useful in formulating soaps, detergents, and the like, wherein at least one of said other components is selected from the group consisting of: fatty acids, alkyl sulfates, an ethanolamine, an amine oxide, alkali carbonates, water, ethanol, isopropanol, pine oil, sodium chloride, sodium silicate, polymers, alcohol alkoxylates, zeolites, perborate salts, alkali sulfates, enzymes, hydrotropes, dyes, fragrances, preservatives, brighteners, builders, polyacrylates, essential oils, alkali hydroxides, water-soluble branched alkylbenzene sulfonates, ether sulfates, alkylphenol alkoxylates, fatty acid amides, alpha olefin sulfonates, paraffin sulfonates, betaines, chelating agents, tallowamine ethoxylates, polyetheramine ethoxylates, ethylene oxide/propylene oxide block copolymers, alcohol ethylene oxide/propylene oxide low foam surfactants, methyl ester sulfonates, alkyl polysaccharides, N-methyl glucamides, alkylated sulfonated diphenyl oxide, polyethylene glycol, and water soluble alkylbenzene sulfonates having a 2-phenyl isomer content of less than 40.00%.

7. A composition of matter comprising alkylbenzenes, which are prepared according to a process comprising:

a) dehydrogenating a paraffin to form an olefin;

b) sending a feed stream of benzene and the olefin through a conduit to an alkylbenzenes alkylation reactor containing a fluorine-containing mordenite and a second alkylation catalyst, wherein the second alkylation catalyst has a selectivity to the 2-phenyl isomer of the alkylbenzenes less than the selectivity of the fluorine-containing mordenite;

c) reacting the benzene and olefin in the reactor to form a crude alkylbenzenes stream;

d) distilling the crude alkylbenzenes stream in a first distillation column to separate benzene that did not react and to form a benzene-free alkylbenzenes stream;

e) distilling the benzene-free alkylbenzenes stream in a second distillation column to separate any paraffin present and to form a paraffin-free alkylbenzenes stream;

f) distilling the paraffin-free alkylbenzene stream in a third distillation column to provide an overhead of a purified alkylbenzene stream and removing a bottoms stream containing heavies.

8. A process for producing an alkylbenzene sulfonic acid comprising the steps of:

a) providing a composition according to claim 7 ; and

b) sulfonating a composition according to claim 7 to form an alkylbenzene sulfonic acid product.

9. The alkylbenzene sulfonic acid product produced by a process according to claim 8 .

10. A process according to claim 8 further comprising: c) neutralizing the product of b) with a suitable alkaline substance containing one or more cations selected from the group consisting of: sodium, potassium, ammonium, magnesium and substituted ammonium alkalis, thus providing an alkylbenzene sulfonate surfactant.

11. The alkylbenzene sulfonate surfactant produced by the process of claim 10 .

12. A composition useful as a detergent for cleaning laundry, dishes, hard surfaces, and other substrates that is formed from components comprising:

a) an alkylbenzene sulfonate surfactant component produced by a process according to claim 10 present in any amount between 0.25% and 99.50% by weight based upon the total weight of the composition, said component characterized as comprising any amount between 30.00% and 82.00% by weight based upon the total weight of the component, including every hundredth percentage therebetween, of water-soluble sulfonates of the 2-phenyl isomers of alkylbenzenes described by the general formula:

wherein n is equal to any integer between 4 and 16; and

b) any amount between 99.75% and 0.50% of a second component that comprises at least one other component known to be useful in formulating soaps, detergents, and the like, wherein at least one of said other components is selected from the group consisting of: fatty acids, alkyl sulfates, an ethanolamine, an amine oxide, alkali carbonates, water, ethanol, isopropanol, pine oil, sodium chloride, sodium silicate, polymers, alcohol alkoxylates, zeolites, perborate salts, alkali sulfates, enzymes, hydrotropes, dyes, fragrances, preservatives, brighteners, builders, polyacrylates, essential oils, alkali hydroxides, water-soluble branched alkylbenzene sulfonates, ether sulfates, alkylphenol alkoxylates, fatty acid amides, alpha olefin sulfonates, paraffin sulfonates, betaines, chelating agents, tallowamine ethoxylates, polyetheramine ethoxylates, ethylene oxide/propylene oxide block copolymers, alcohol ethylene oxide/propylene oxide low foam surfactants, methyl ester sulfonates, alkyl polysaccharides, N-methyl glucamides, alkylated sulfonated diphenyl oxide, polyethylene glycol, and water soluble alkylbenzene sulfonates having a 2-phenyl isomer content of less than 40.00%.

13. A composition of matter comprising alkylbenzenes, which are prepared according to a process comprising:

a) contacting benzene and an olefin having about 8 to about 30 carbon atoms in the presence of a fluorine-containing mordenite to form a first alkylbenzene stream;

b) contacting benzene and an olefin having about 8 to about 30 carbon atoms in the presence of an alkylation catalyst other than the fluorine-containing mordenite to form a second alkylbenzene stream;

c) combining the first alkylbenzene stream and the second alkylbenzene stream to form a third alkylbenzene stream,

wherein the mordenite has been treated by contacting the mordenite with an aqueous hydrogen fluoride solution, wherein the hydrogen fluoride in the aqueous solution has a concentration in the range from about 0.1 percent to about 1 percent by weight.

14. A process for producing an alkylbenzene sulfonic acid comprising the steps of:

a) providing a composition according to claim 13 ; and

b) sulfonating a composition according to claim 13 to form an alkylbenzene sulfonic acid product.

15. The alkylbenzene sulfonic acid product produced by a process according to claim 14 .

16. A process according to claim 14 further comprising: c) neutralizing the product of b) with a suitable alkaline substance containing one or more cations selected from the group consisting of: sodium, potassium, ammonium, magnesium and substituted ammonium alkalis, thus providing an alkylbenzene sulfonate surfactant.

17. The alkylbenzene sulfonate surfactant produced by the process of claim 16 .

18. A composition useful as a detergent for cleaning laundry, dishes, hard surfaces, and other substrates that is formed from components comprising:

a) an alkylbenzene sulfonate surfactant component produced by a process according to claim 16 present in any amount between 0.25% and 99.50% by weight based upon the total weight of the composition, said component characterized as comprising any amount between 30.00% and 82.00% by weight based upon the total weight of the component, including every hundredth percentage therebetween, of water-soluble sulfonates of the 2-phenyl isomers of alkylbenzenes described by the general formula:

wherein n is equal to any integer between 4 and 16; and

b) any amount between 99.75% and 0.50% of a second component that comprises at least one other component known to be useful in formulating soaps, detergents, and the like, wherein at least one of said other components is selected from the group consisting of: fatty acids, alkyl sulfates, an ethanolamine, an amine oxide, alkali carbonates, water, ethanol, isopropanol, pine oil, sodium chloride, sodium silicate, polymers, alcohol alkoxylates, zeolites, perborate salts, alkali sulfates, enzymes, hydrotropes, dyes, fragrances, preservatives, brighteners, builders, polyacrylates, essential oils, alkali hydroxides, water-soluble branched alkylbenzene sulfonates, ether sulfates, alkylphenol alkoxylates, fatty acid amides, alpha olefin sulfonates, paraffin sulfonates, betaines, chelating agents, tallowamine ethoxylates, polyetheramine ethoxylates, ethylene oxide/propylene oxide block copolymers, alcohol ethylene oxide/propylene oxide low foam surfactants, methyl ester sulfonates, alkyl polysaccharides, N-methyl glucamides, alkylated sulfonated diphenyl oxide, polyethylene glycol, and water soluble alkylbenzene sulfonates having a 2-phenyl isomer content of less than 40.00%.

19. A composition of matter comprising alkylbenzenes, which are prepared according to a process comprising:

a) introducing an aromatic compound having from about 6 to about 30 carbon atoms and an olefin having from about 8 to about 30 carbon atoms above a catalyst bed containing an alkylation catalyst;

b) contacting the olefin and the aromatic compound in the presence of the alkylation catalyst under conditions such that the olefin and the aromatic compound react to form an alkylated aromatic compound;

c) allowing the alkylated aromatic compound an any unreacted aromatic compound to descend into a reboiler from the catalyst bed;

d) withdrawing the alkylated aromatic compound from the reboiler; and

e) heating the contents of the reboiler such that the aromatic compound refluxes to contact the catalyst bed.

20. A process for producing an alkylbenzene sulfonic acid comprising the steps of:

a) providing a composition according to claim 19 ; and

b) sulfonating a composition according to claim 19 to form an alkylbenzene sulfonic acid product.

21. The alkylbenzene sulfonic acid product produced by a process according to claim 20 .

22. A process according to claim 20 further comprising: c) neutralizing the product of b) with a suitable alkaline substance containing one or more cations selected from the group consisting of sodium, potassium, ammonium, magnesium and substituted ammonium alkalis, thus providing an alkylbenzene sulfonate surfactant.

23. The alkylbenzene sulfonate surfactant produced by the process of claim 22 .

24. A composition useful as a detergent for cleaning laundry, dishes, hard surfaces, and other substrates that is formed from components comprising:

a) an alkylbenzene sulfonate surfactant component produced by a process according to claim 22 present in any amount between 0.25% and 99.50% by weight based upon the total weight of the composition, said component characterized as comprising any amount between 30.00% and 82.00% by weight based upon the total weight of the component, including every hundredth percentage therebetween, of water-soluble sulfonates of the 2-phenyl isomers of alkylbenzenes described by the general formula:

wherein n is equal to any integer between 4 and 16; and

b) any amount between 99.75% and 0.50% of a second component that comprises at least one other component known to be useful in formulating soaps, detergents, and the like, wherein at least one of said other components is selected from the group consisting of: fatty acids, alkyl sulfates, an ethanolamine, an amine oxide, alkali carbonates, water, ethanol, isopropanol, pine oil, sodium chloride, sodium silicate, polymers, alcohol alkoxylates, zeolites, perborate salts, alkali sulfates, enzymes, hydrotropes, dyes, fragrances, preservatives, brighteners, builders, polyacrylates, essential oils, alkali hydroxides, water-soluble branched alkylbenzene sulfonates, ether sulfates, alkylphenol alkoxylates, fatty acid amides, alpha olefin sulfonates, paraffin sulfonates, betaines, chelating agents, tallowamine ethoxylates, polyetheramine ethoxylates, ethylene oxide/propylene oxide block copolymers, alcohol ethylene oxide/propylene oxide low foam surfactants, methyl ester sulfonates, alkyl polysaccharides, N-methyl glucamides, alkylated sulfonated diphenyl oxide, polyethylene glycol, and water soluble alkylbenzene sulfonates having a 2-phenyl isomer content of less than 40.00%.

25. A composition of matter comprising alkylbenzenes, which are prepared according to a process comprising:

a) introducing an aromatic compound having from about 6 to about 30 carbon atoms and an olefin having from about 8 to about 30 carbon atoms above a catalyst bed containing an alkylation catalyst;

b) contacting the olefin and the aromatic compound in the presence of the alkylation catalyst under conditions such that the olefin and the aromatic compound react to form an alkylated aromatic compound;

c) allowing the alkylated aromatic compound an any unreacted aromatic compound to descend into a reboiler from the catalyst bed;

d) withdrawing the alkylated aromatic compound from the reboiler; and

e) heating the contents of the reboiler such that the aromatic compound refluxes to contact the catalyst bed,

wherein the process produces a selectivity to a 2-phenyl isomer in the alkylated aromatic compound of at least about 70 mole percent.

26. A process for producing an alkylated benzene sulfonic acid comprising the steps of:

a) providing a composition according to claim 25 ; and

b) sulfonating a composition according to claim 25 to form an alkylbenzene sulfonic acid product.

27. The alkylbenzene sulfonic acid product produced by a process according to claim 26 .

28. A process according to claim 26 further comprising: c) neutralizing the product of b) with a suitable alkaline substance containing one or more cations selected from the group consisting of: sodium, potassium, ammonium, magnesium and substituted ammonium alkalis, thus providing an alkylbenzene sulfonate surfactant.

29. The alkylbenzene sulfonate surfactant produced by the process of claim 28 .

30. A composition useful as a detergent for cleaning laundry, dishes, hard surfaces, and other substrates that is formed from components comprising:

a) an alkylbenzene sulfonate surfactant component produced by a process according to claim 28 present in any amount between 0.25% and 99.50% by weight based upon the total weight of the composition, said component characterized as comprising any amount between 30.00% and 82.00% by weight based upon the total weight of the component, including every hundredth percentage therebetween, of water-soluble sulfonates of the 2-phenyl isomers of alkylbenzenes described by the general formula:

wherein n is equal to any integer between 4 and 16; and

b) any amount between 99.75% and 0.50% of a second component that comprises at least one other component known to be useful in formulating soaps, detergents, and the like, wherein at least one of said other components is selected from the group consisting of: fatty acids, alkyl sulfates, an ethanolamine, an amine oxide, alkali carbonates, water, ethanol, isopropanol, pine oil, sodium chloride, sodium silicate, polymers, alcohol alkoxylates, zeolites, perborate salts, alkali sulfates, enzymes, hydrotropes, dyes, fragrances, preservatives, brighteners, builders, polyacrylates, essential oils, alkali hydroxides, water-soluble branched alkylbenzene sulfonates, ether sulfates, alkylphenol alkoxylates, fatty acid amides, alpha olefin sulfonates, paraffin sulfonates, betaines, chelating agents, tallowamine ethoxylates, polyetheramine ethoxylates, ethylene oxide/propylene oxide block copolymers, alcohol ethylene oxide/propylene oxide low foam surfactants, methyl ester sulfonates, alkyl polysaccharides, N-methyl glucamides, alkylated sulfonated diphenyl oxide, polyethylene glycol, and water soluble alkylbenzene sulfonates having a 2-phenyl isomer content of less than 40.00%.

31. A composition of matter comprising alkylbenzenes, which are prepared according to a process comprising:

contacting benzene with an olefin of from about 8 to about 30 carbon atoms in the presence of a catalyst consisting essentially of fluorine-containing mordenite under conditions such that monoalkylated benzene is formed,

wherein the mordenite has been treated by contacting mordenite with an aqueous hydrogen fluoride solution, wherein the hydrogen fluoride in the aqueous solution has a concentration in the range from about 0.1 to about 1 percent by weight.

32. A process for producing an alkylbenzene sulfonic acid comprising the steps of:

a) providing a composition according to claim 31 ; and

b) sulfonating a composition according to claim 31 to form an alkylbenzene sulfonic acid product.

33. The alkylbenzene sulfonic acid product produced by a process according to claim 32 .

34. A process according to claim 32 further comprising: c) neutralizing the product of b) with a suitable alkaline substance containing one or more cations selected from the group consisting of: sodium, potassium, ammonium, magnesium and substituted ammonium alkalis, thus providing an alkylbenzene sulfonate surfactant.

35. The alkylbenzene sulfonate surfactant produced by the process of claim 34 .

36. A composition useful as a detergent for cleaning laundry, dishes, hard surfaces, and other substrates that is formed from components comprising:

a) an alkylbenzene sulfonate surfactant component produced by a process according to claim 34 present in any amount between 0.25% and 99.50% by weight based upon the total weight of the composition, said component characterized as comprising any amount between 30.00% and 82.00% by weight based upon the total weight of the component, including every hundredth percentage therebetween, of water-soluble sulfonates of the 2-phenyl isomers of alkylbenzenes described by the general formula:

wherein n is equal to any integer between 4 and 16; and

b) any amount between 99.75% and 0.50% of a second component that comprises at least one other component known to be useful in formulating soaps, detergents, and the like, wherein at least one of said other components is selected from the group consisting of: fatty acids, alkyl sulfates, an ethanolamine, an amine oxide, alkali carbonates, water, ethanol, isopropanol, pine oil, sodium chloride, sodium silicate, polymers, alcohol alkoxylates, zeolites, perborate salts, alkali sulfates, enzymes, hydrotropes, dyes, fragrances, preservatives, brighteners, builders, polyacrylates, essential oils, alkali hydroxides, water-soluble branched alkylbenzene sulfonates, ether sulfates, alkylphenol alkoxylates, fatty acid amides, alpha olefin sulfonates, paraffin sulfonates, betaines, chelating agents, tallowamine ethoxylates, polyetheramine ethoxylates, ethylene oxide/propylene oxide block copolymers, alcohol ethylene oxide/propylene oxide low foam surfactants, methyl ester sulfonates, alkyl polysaccharides, N-methyl glucamides, alkylated sulfonated diphenyl oxide, polyethylene glycol, and water soluble alkylbenzene sulfonates having a 2-phenyl isomer content of less than 40.00%.

37. A composition of matter comprising alkylbenzenes, which are prepared according to a process comprising:

a) introducing a feed comprising olefin having about 8 to about 30 carbon atoms and benzene into a catalyst consisting essentially of fluorine-containing mordenite catalyst bed under conditions such that monoalkylated benzene is produced;

b) allowing benzene, olefin, and monoalkylated benzene to descend into a reboiler from the catalyst bed;

c) removing monoalkylated benzene from the reboiler; and

d) heating the contents of the reboiler such that benzene refluxes to further contact the fluorine-containing mordenite,

wherein the mordenite has been treated by contacting mordenite with an aqueous hydrogen fluoride solution, wherein the hydrogen fluoride in the aqueous solution has a concentration in the range from about 0.1 to about 1 percent by weight.

38. A process for producing an alkylbenzene sulfonic acid comprising the steps of:

a) providing a composition according to claim 37 ; and

b) sulfonating a composition according to claim 37 to form an alkylbenzene sulfonic acid product.

39. The alkylbenzene sulfonic acid product produced by a process according to claim 38 .

40. A process according to claim 38 further comprising: c) neutralizing the product of b) with a suitable alkaline substance containing one or more cations selected from the group consisting of: sodium, potassium, ammonium, magnesium and substituted ammonium alkalis, thus providing an alkylbenzene sulfonate surfactant.

41. The alkylbenzene sulfonate surfactant produced by the process of claim 40 .

42. A composition useful as a detergent for cleaning laundry, dishes, hard surfaces, and other substrates that is formed from components comprising:

a) an alkylbenzene sulfonate surfactant component produced by a process according to claim 40 present in any amount between 0.25% and 99.50% by weight based upon the total weight of the composition, said component characterized as comprising any amount between 30.00% and 82.00% by weight based upon the total weight of the component, including every hundredth percentage therebetween, of water-soluble sulfonates of the 2-phenyl isomers of alkylbenzenes described by the general formula:

wherein n is equal to any integer between 4 and 16; and

b) any amount between 99.75% and 0.50% of a second component that comprises at least one other component known to be useful in formulating soaps, detergents, and the like, wherein at least one of said other components is selected from the group consisting of: fatty acids, alkyl sulfates, an ethanolamine, an amine oxide, alkali carbonates, water, ethanol, isopropanol, pine oil, sodium chloride, sodium silicate, polymers, alcohol alkoxylates, zeolites, perborate salts, alkali sulfates, enzymes, hydrotropes, dyes, fragrances, preservatives, brighteners, builders, polyacrylates, essential oils, alkali hydroxides, water-soluble branched alkylbenzene sulfonates, ether sulfates, alkylphenol alkoxylates, fatty acid amides, alpha olefin sulfonates, paraffin sulfonates, betaines, chelating agents, tallowamine ethoxylates, polyetheramine ethoxylates, ethylene oxide/propylene oxide block copolymers, alcohol ethylene oxide/propylene oxide low foam surfactants, methyl ester sulfonates, alkyl polysaccharides, N-methyl glucamides, alkylated sulfonated diphenyl oxide, polyethylene glycol, and water soluble alkylbenzene sulfonates having a 2-phenyl isomer content of less than 40.00%.

43. A composition of matter comprising alkylbenzenes, which are prepared according to a process comprising:

a) contacting benzene with an olefin of from about 5 to about 30 carbons in the presence of fluorine-containing mordenite under conditions such that monoalkylated benzene is formed; and

b) contacting the effluent from step a) with benzene in the presence of a fluorine-containing clay catalyst,

such that the product of step b) has a bromine number less than the bromine number of the product of step a).

44. A process for producing an alkylbenzene sulfonic acid comprising the steps of:

a) providing a composition according to claim 43 ; and

b) sulfonating a composition according to claim 43 to form an alkylated benzene sulfonic acid product.

45. The alkylbenzene sulfonic acid product produced by a process according to claim 44 .

46. A process according to claim 44 further comprising: c) neutralizing the product of b) with a suitable alkaline substance containing one or more cations selected from the group consisting of: sodium, potassium, ammonium, magnesium and substituted ammonium alkalis, thus providing an alkylbenzene sulfonate surfactant.

47. The alkylbenzene sulfonate surfactant produced by the process of claim 46 .

48. A composition useful as a detergent for cleaning laundry, dishes, hard surfaces, and other substrates that is formed from components comprising:

a) an alkylbenzene sulfonate surfactant component produced by a process according to claim 46 present in any amount between 0.25% and 99.50% by weight based upon the total weight of the composition, said component characterized as comprising any amount between 30.00% and 82.00% by weight based upon the total weight of the component, including every hundredth percentage therebetween, of water-soluble sulfonates of the 2-phenyl isomers of alkylbenzenes described by the general formula:

wherein n is equal to any integer between 4 and 16; and

b) any amount between 99.75% and 0.50% of a second component that comprises at least one other component known to be useful in formulating soaps, detergents, and the like, wherein at least one of said other components is selected from the group consisting of: fatty acids, alkyl sulfates, an ethanolamine, an amine oxide, alkali carbonates, water, ethanol, isopropanol, pine oil, sodium chloride, sodium silicate, polymers, alcohol alkoxylates, zeolites, perborate salts, alkali sulfates, enzymes, hydrotropes, dyes, fragrances, preservatives, brighteners, builders, polyacrylates, essential oils, alkali hydroxides, water-soluble branched alkylbenzene sulfonates, ether sulfates, alkylphenol alkoxylates, fatty acid amides, alpha olefin sulfonates, paraffin sulfonates, betaines, chelating agents, tallowamine ethoxylates, polyetheramine ethoxylates, ethylene oxide/propylene oxide block copolymers, alcohol ethylene oxide/propylene oxide low foam surfactants, methyl ester sulfonates, alkyl polysaccharides, N-methyl glucamides, alkylated sulfonated diphenyl oxide, polyethylene glycol, and water soluble alkylbenzene sulfonates having a 2-phenyl isomer content of less than 40.00%.

49. A composition of matter comprising alkylbenzenes, which are prepared according to a process comprising:

a) introducing a feed comprising olefin having about 5 to about 30 carbons and benzene into fluorine-containing mordenite catalyst bed under conditions such that monoalkylated benzene is produced;

b) collecting benzene, olefin, and monoalkylated benzene that descends from the catalyst bed in a reboiler;

c) heating the contents of the reboiler such that benzene refluxes to further contact the fluorine-containing mordenite;

d) removing monoalkylated benzene having a bromine number from the reboiler; and

e) contacting the monoalkylated benzene removed from the reboiler with benzene in the presence of a fluorine-containing clay catalyst such that the bromine number of the monoalkylated benzene removed from the reboiler is reduced.

50. A process for producing an alkylbenzene sulfonic acid comprising the steps of:

a) providing a composition according to claim 49 ; and

b) sulfonating a composition according to claim 49 to form an alkylbenzene sulfonic acid product.

51. The alkylbenzene sulfonic acid product produced by a process according to claim 50 .

52. A process according to claim 50 further comprising: c) neutralizing the product of b) with a suitable alkaline substance containing one or more cations selected from the group consisting of: sodium, potassium, ammonium, magnesium and substituted ammonium alkalis, thus providing an alkylbenzene sulfonate surfactant.

53. The alkylbenzene sulfonate surfactant produced by the process of claim 52 .

54. A composition useful as a detergent for cleaning laundry, dishes, hard surfaces, and other substrates that is formed from components comprising:

a) an alkylbenzene sulfonate surfactant component produced by a process according to claim 52 present in any amount between 0.25% and 99.50% by weight based upon the total weight of the composition, said component characterized as comprising any amount between 30.00% and 82.00% by weight based upon the total weight of the component, including every hundredth percentage therebetween, of water-soluble sulfonates of the 2-phenyl isomers of alkylbenzenes described by the general formula:

wherein n is equal to any integer between 4 and 16; and

b) any amount between 99.75% and 0.50% of a second component that comprises at least one other component known to be useful in formulating soaps, detergents, and the like, wherein at least one of said other components is selected from the group consisting of: fatty acids, alkyl sulfates, an ethanolamine, an amine oxide, alkali carbonates, water, ethanol, isopropanol, pine oil, sodium chloride, sodium silicate, polymers, alcohol alkoxylates, zeolites, perborate salts, alkali sulfates, enzymes, hydrotropes, dyes, fragrances, preservatives, brighteners, builders, polyacrylates, essential oils, alkali hydroxides, water-soluble branched alkylbenzene sulfonates, ether sulfates, alkylphenol alkoxylates, fatty acid amides, alpha olefin sulfonates, paraffin sulfonates, betaines, chelating agents, tallowamine ethoxylates, polyetheramine ethoxylates, ethylene oxide/propylene oxide block copolymers, alcohol ethylene oxide/propylene oxide low foam surfactants, methyl ester sulfonates, alkyl polysaccharides, N-methyl glucamides, alkylated sulfonated diphenyl oxide, polyethylene glycol, and water soluble alkylbenzene sulfonates having a 2-phenyl isomer content of less than 40.00%.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 20, 2020
From: HUNTSMAN PETROCHEMICAL LLC
To: INDORAMA VENTURES OXIDES LLC
Reel/Frame 051649/0173 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN UNITED STATES TRADEMARKS AND PATENTS Recorded Jun 13, 2018
From: JPMORGAN CHASE BANK, N.A.
To: HUNTSMAN PETROCHEMICAL CORPORATION (N/K/A HUNTSMAN PETROCHEMICAL LLC)
Reel/Frame 046356/0616 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE FROM AN ASSIGNMENT TO A SECURITY AGREEMENT PREVIOUSLY RECORDED ON REEL 025857 FRAME 0137. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 28, 2011
From: DEUTSCHE BANK TRUST AG NEW YORK BRANCH, AS RESIGNING ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 026515/0641 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 28, 2011
From: DEUTSCHE BANK TRUST AG NEW YORK BRANCH, AS RESIGNING ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 025857/0137 →
RELEASE OF SECURITY INTEREST Recorded Feb 8, 2011
From: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT (F/K/A BANKERS TRUST COMPANY, AS COLLATERAL AGENT)
To: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN ETHYLEMEAMINES LLC; HUNTSMAN PETROCHEMICAL LLC
Reel/Frame 025765/0853 →
SECURITY INTEREST Recorded Nov 17, 2005
From: HUNTSMAN PETROCHEMICAL CORPORATION
To: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
Reel/Frame 016987/0496 →
SECURITY AGREEMENT Recorded Jan 28, 2005
From: HUNSTMAN PETROCHEMICAL CORPORATION
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS AGENT
Reel/Frame 015661/0547 →
GRANT OF SECURITY INTEREST IN U.S. TRADEMARKS AND PATENTS Recorded Dec 4, 2003
From: HUNTSMAN PETROCHEMICAL CORPORATION
To: DEUTSCHE BANK TRUST COMPANY AMERICAS (FORMERLY KNOWN AS BANKER TRUST COMPANY), AS COLLATERAL AGENT
Reel/Frame 014782/0186 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 15, 2002
From: SMITH, GEORGE A.; ANANTANENI, PRAKASA R.; ASHRAWI, SAMIR S.; SMADI, RAEDA M.; KNIFTON, JOHN F.; STOCKTON, MELVIN
To: HUNTSMAN PETROCHEMICAL CORPORATION
Reel/Frame 013554/0043 →