Highly branched primary alcohol compositions and biodegradable detergents made therefrom

• US 6,150,322 A
• Filed: 08/12/1998
• Issued: 11/21/2000
• Est. Priority Date: 08/12/1998
• Status: Expired due to Term

• Current Assignee: Shell Oil Company (Shell Plc)
• Original Assignee: Shell Oil Company (Shell Plc)
• Inventors: Kravetz, Louis, Singleton, David M., Murray, Brendan Dermot
• Primary Examiner(s): OGDEN JR, NECHOLUS
• Application Number:
  US09/133,303
• Time in Patent Office: 832 Days
• Field of Search: 510/424, 510/426, 510/428, 568/909, 585/512, 252/182.11
• US Class Current: 510/426
• CPC Class Codes: C11D 1/146 Sulfuric acid esters
• CPC Class Codes: C11D 1/72 Ethers of polyoxyalkylene glycols

Abstract

There is provided a new branched primary alcohol composition and the sulfates thereof exhibiting good cold water detergency and biodegradability. The branched primary alcohol composition has an average number of branches per chain of at least 0.7, having at least 8 carbon atoms and contianing both methyl and ethyl branches. The primary alcohol composition may also contain less than 0.5 atom % of quaternary carbon atoms, and a significant number ethyl branches, terminal isopropyl branches, and branching at the C₃ position relative to the hydroxyl carbon. The process for its manufacture is by skeletally isomerizing an olefin feed having at least 7 carbon atoms followed by conversion to an alcohol, as by way of hydroformylation, and ultimately, sulfation to obtain a detergent surfactant. Useful catalysts include the zeolites having at least one channel with a crystallographic free diameter along the x and/or y planes of the [001] view ranging from greater than 4.2 Å and less than 7 Å. but allows one to skeletally isomerize the olefin to produce a variety of branches, while retaining ready biodegradability and good cold water detergency.

Claims

1. A detergent composition comprising:

a) a surfactant comprising a biodegradable sulfate composition comprising sulfates of an alkyl branched primary alcohol composition having at least 8 carbon atoms, wherein said alcohol composition has an average number of branches per molecule chain of at least 0.7, said branching comprising methyl and ethyl branches;

b) a builder;

c) and optionally foam controlling agents, enzymes, bleaching agents, bleach activators, optical brighteners, cobuilders, hydrotropes, stabilizers, or mixtures thereof.

2. The detergent composition of claim 1, comprising a granular laundry detergent.

3. The detergent composition of claim 1, comprising a liquid laundry detergent.

4. The detergent composition of claim 1, comprising a liquid dishwashing detergent.

5. The detergent composition of claim 1, comprising a liquid soaps, a shampoo, or a scouring agent.

6. The detergent composition of claim 1, wherein the composition contains from 5 and 35% by weight of the builder.

7. The detergent composition of claim 1, wherein said composition is free of phosphate containing builder.

8. The detergent composition of claim 7, wherein said builder comprises alkali metal carbonates, silicates, sulfates, polycarboxylates, aminocarboxylates, nitrilotriacetates, hydroxycarboxylates, citrates, succinates, substituted and unsubstituted alkanedi- and polycarboxylic acids, complex aluminosilicates, or mixtures thereof.

9. The detergent composition of claim 1, containing a bleaching agent comprising a perborates, percarbonates, persulfates, organic peroxy acids, or a mixture thereof.

10. The detergent composition of claim 1, containing a bleach activator comprising carboxylic acid amides, substituted carboxylic acids, or mixtures thereof.

11. The detergent composition of claim 1, containing a hydrotrope comprising an alkali metal salts of aromatic sulfonic acids or alkyl carboxylic acids, alkali metal chlorides, urea, mono- or polyalkanolamines, or mixtures thereof.

12. The detergent composition of claim 1, wherein said surfactant contains less than 0.5 atom % of quarternary carbon atoms.

13. The detergent composition of claim 1, wherein said surfactant contains at least 5% isopropyl termination.

14. The detergent composition of claim 1, wherein said surfactant contains at least 40% methyl branching, based on the overall branching present.

15. The detergent composition of claim 1, wherein said surfactant contains ethyl branching in an amount of at 5% to 30%.

16. The detergent composition of claim 1, wherein the surfactant contains 5 to 30% of branching at the C₃ position.

17. The detergent composition of claim 1, wherein the surfactant contains a higher concentration of branches at the C₂ and C₃ ends of the carbon molecule than the number of branches found at the C₄ or longer positions from both ends of the molecule proceeding inward towards the center.

18. A detergent composition comprising:

(a) a surfactant comprising a biodegradable sulfate composition comprising sulfates of an alkyl branched primary alcohol composition, said alkyl branched primary alcohol composition obtained by skeletally isomerizing olefins under skeletal isomerization conditions and converting said olefins to primary alcohols having an average carbon number ranging from 8 to 36 carbon atoms and an average number of branches per molecule ranging from 0.7 to 2.1; and

(b) a builder.

19. The detergent composition of claim 18, comprising a granular laundry detergent.

20. The detergent composition of claim 18, comprising a liquid laundry detergent.

21. The detergent composition of claim 18, comprising a liquid dishwashing detergent.

22. The detergent composition of claim 18, comprising a liquid soap, a shampoo, or a scouring agent.

23. The detergent composition of claim 18, wherein the composition contains from 5 to 35 weight percent builder.

24. The detergent composition of claim 18, wherein said composition is free of phosphate containing builders.

25. The detergent composition of claim 18, wherein said builder comprises an alkali metal carbonate, a silicate, a sulfate, a polycarboxylic, an amino carboxylic, a nitrilo triacetate, a hydroxy carboxylic, a citrate, a succinate, substituted and unsubstituted alkane di- and polycarboxylic acids, complex amino silicates, or mixtures thereof.

26. The detergent composition of claim 18, further comprising a bleaching agent comprising a perborate, percarbonate, persulfate, organic peroxy acid, or a mixture thereof.

27. The detergent composition of claim 18, further comprising a bleach activator comprising carboxylic acid amides, substituted carboxylic acids, or mixtures thereof.

28. The detergent composition of claim 18, further comprising a hydrotrope comprising an alkali metal salt of aromatic sulfonic acids or alkyl carboxylic acids, an alkali metal chloride, a urea, a mono- or polyalkanol amine, or mixtures thereof.

29. The detergent composition of claim 18, wherein said alkyl branched primary alcohol composition contains less than 0.5 atom percent of quaternary carbon atoms.

30. The detergent composition of claim 18, wherein said alkyl branched primary alcohol composition contains at least 5 percent isopropyl termination.

31. The detergent composition of claim 18, wherein said alkyl branched primary alcohol composition contains at least 40 percent methyl branching, based on the overall branching present.

32. The detergent composition of claim 18, wherein said alkyl branched primary alcohol composition contains ethyl branching in an amount ranging from 5 percent to 30 percent.

33. The detergent composition of claim 18, wherein said alkyl branched primary alcohol composition contains 5 to 30 percent of branching at the C₃ position.

34. The detergent composition of claim 18, wherein said alkyl branched primary alcohol composition contains a higher concentration of branches at the C₂ and C₃ ends of the carbon molecule than the number of branches found at the C₄ or longer positions from both ends of the molecule proceeding inward towards the center.

35. The detergent composition of claim 18, wherein said olefins are contacted with a catalyst at a temperature ranging from 200°

C. to the lesser of 500°

C. or the temperature at which the olefin cracks.

36. The detergent composition of claim 18, wherein said olefins are contacted with a catalyst at an olefin partial pressure ranging from 0.1 atmospheres to 10 atmospheres and at a temperature ranging from 200°

C. to the lesser of 500°

C. or the temperature at which the olefin cracks.

37. The detergent composition of claim 18, wherein said olefins contain greater than 50 percent of linear olefins having an average carbon number ranging from C₁₁ to C₁₉.

38. The detergent of claim 18, wherein said olefins contain greater than 50 percent linear olefins and are converted to skeletal isomerized olefins, and subsequently converted to a said primary alcohol composition, wherein less than 5 percent of the alcohol molecules in the primary alcohol composition are linear alcohols.

39. A detergent composition comprising:

(a) a biodegradable sulfate composition comprising sulfates of an alkyl branched primary alcohol composition, wherein said alcohol composition has an average number of branches per molecule of at least 0.7, and wherein from 5-25 percent of the number of branches of the alcohol composition are located at the C₂ atom position, and wherein from 10 to 50 percent of the number of branches of the alcohol composition are located at the C₃ atoms of the molecules in the alcohol composition; and

(b) a builder.

40. A detergent composition comprising:

(a) a surfactant comprising a biodegradable sulfate composition comprising sulfates of an alkyl branched primary alcohol composition, said alkyl branched primary alcohol composition obtained by skeletally isomerizing olefins under skeletal isomerization conditions and converting said olefins to primary alcohols having an average carbon number ranging from 8 to 36 carbon atoms and an average number of branches per molecule ranging from 0.7 to 2.1 and containing at least 5 percent isopropyl termination; and

(b) a builder.

41. A detergent composition comprising:

(a) a surfactant comprising a biodegradable sulfate composition comprising sulfates of an alkyl branched primary alcohol composition, said alkyl branched primary alcohol composition obtained by skeletally isomerizing olefins under skeletal isomerization conditions and converting said olefins to primary alcohols having an average carbon number ranging from 8 to 36 carbon atoms and an average number of branches per molecule ranging from 0.7 to 2.1 and having from 5 percent to 30 percent of ethyl branching; and

(b) a builder.

42. A detergent composition comprising:

(a) a surfactant comprising a biodegradable sulfate composition comprising sulfates of an alkyl branched primary alcohol composition, said alkyl branched primary alcohol composition obtained by skeletally isomerizing olefins under skeletal isomerization conditions and converting said olefins to primary alcohols having an average carbon number ranging from 8 to 36 carbon atoms and an average number of branches per molecule ranging from 0.7 to 2.1 and having from 5 to 30 percent branching at the C₃ position; and

(b) a builder.

43. A detergent composition comprising:

(a) a surfactant comprising a biodegradable sulfate composition comprising sulfates of an alkyl branched primary alcohol composition, said alkyl branched primary alcohol composition obtained by skeletally isomerizing olefins under skeletal isomerization conditions and converting said olefins to primary alcohols having an average carbon number ranging from 8 to 36 carbon atoms and an average number of branches per molecule ranging from 0.7 to 2.1 and wherein the primary alcohol composition contains a higher concentration of branches at the C₂ and C₃ ends of the carbon molecule than the number of branches found at the C₄ or longer positions from both ends of the molecule proceeding inward towards the center; and

(b) a builder.

44. A detergent composition comprising:

(a) a surfactant comprising a biodegradable sulfate composition comprising sulfates of an alkyl branched primary alcohol composition having at least 8 carbon atoms, wherein said alcohol composition has an average number of branches per molecule chain of at least 0.7, said branching comprising methyl and ethyl branches and wherein said surfactant contains 5 to 30 percent of branching at the C₃ position;

(b) a builder;

(c) and optionally foam controlling agents, enzymes, bleaching agents, bleach activators, optical brighteners, cobuilders, hydrotropes, stabilizers, or mixtures thereof.

45. A detergent composition comprising:

(a) a surfactant comprising a biodegradable sulfate composition comprising sulfates of an alkyl branched primary alcohol composition having at least 8 carbon atoms, wherein said alcohol composition has an average number of branches per molecule chain of at least 0.7, said branching comprising methyl and ethyl branches, wherein said surfactant contains ethyl branching in an amount ranging from 5 to 30 percent;

(b) a builder;

(c) and optionally foam controlling agents, enzymes, bleaching agents, bleach activators, optical brighteners, cobuilders, hydrotropes, stabilizers, or mixtures thereof.

46. A detergent composition comprising:

(a) a surfactant comprising a biodegradable sulfate composition comprising sulfates of an alkyl branched primary alcohol composition having at least 8 carbon atoms, wherein said alcohol composition has an average number of branches per molecule chain of at least 0.7, said branching comprising methyl and ethyl branches, wherein said surfactant contains a higher concentration of branches at the C₂ and C₃ ends of the carbon molecule than the number of branches found at the C₄ or longer position from both ends of the molecule proceeding inward towards the center;

(b) a builder;

(c) and optionally foam controlling agents, enzymes, bleaching agents, bleach activators, optical brighteners, cobuilders, hydrotropes, stabilizers, or mixtures thereof.