IP Library Granted Patent US 9,617,608
Granted Patent B2
US 9,617,608 · App. 14/385,142 · Granted Apr 11, 2017

Sugar compositions

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,617,608
App. No.
14/385,142
Granted
Apr 11, 2017
Kind
B2
Abstract

A sugar composition comprising at least 40% dissolved solids in an aqueous solution having a viscosity at least 10% lower than a 42 DE (Dextrose Equivalents) reference solution with a same dissolved solids concentration at a given temperature. Another sugar composition comprising at least 30% glucose relative to total sugars, at least 10% mannose relative to total sugars, at least 5% xylose relative to total sugars, and less than 0.25% ash. Another sugar composition comprising at least 30% glucose relative to total sugars at least 10% mannose relative to total sugars, at least 5% xylose relative to total sugars, and at least 2% total furfurals.

Claims (149)

1. A composition comprising:

(a) at least one water-soluble monomeric hydrolyzate comprising a monomeric hemicellulose sugar hydrolyzate;

(b) at least one water-soluble dimeric or higher oligomeric hydrolyzate comprising a dimeric or higher oligomeric hemicellulose sugar hydrolyzate;

(c) ash in an amount up to 0.25% in total by weight, relative to the total solids in the composition; and

(d) furfural in an amount up to 10% by weight, based on the total weight of the total solids in the composition;

wherein the composition is provided as an aqueous solution.

2. The composition of claim 1 , wherein one or more of the water-soluble monomeric hydrolyzates is a pentose and one or more of the water-soluble dimeric or higher oligomeric hydrolyzate is a pentose.

3. The composition of claim 1 , wherein the ash comprises Ca, Cu, Fe, K, Mg, Mn, Na, P, S, and Si.

4. The composition of claim 3 , wherein:

the water-soluble monomeric hydrolyzate is selected from xylose, arabinose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from a dimer or higher oligomer of xylose, arabinose, or a combination thereof.

5. The composition of claim 1 , wherein the water-soluble monomeric hydrolyzate is derived from a lignocellulose substrate.

6. The composition of claim 1 , wherein the water-soluble monomeric hydrolyzate is present at a concentration of at least 90% in an aqueous solution.

7. The composition of claim 1 , wherein the water-soluble monomeric hydrolyzate is xylose, arabinose, or a mixture thereof.

8. The composition of claim 1 , further comprising less than 1 ppm by weight, based on the total weight of the total solids in the composition, of calcium.

9. The composition of claim 1 , further comprising less than 1 ppm by weight, based on the total weight of the total solids in the composition, of iron.

10. The composition of claim 1 , further comprising less than 50 ppm by weight, based on the total weight of the total solids in the composition, of sulfur.

11. The composition of claim 1 , wherein the weight ratio of the water-soluble monomeric hydrolyzate to the ash is greater than 360:1.

12. The composition of claim 1 , wherein one or more of the hydrolyzates is a hexose.

13. The composition of claim 1 , further comprising levulinic acid, wherein a molar ratio of levulinic acid to sugars is between 0.03 and 0.12.

14. A composition comprising:

(a) at least one water-soluble monomeric hydrolyzate comprising a monomeric hemicellulose sugar hydrolyzate;

(b) at least one water-soluble dimeric or higher oligomeric hydrolyzate comprising a dimeric or higher oligomeric hemicellulose sugar hydrolyzate;

(c) impurities, wherein the impurities comprise:

less than 1 ppm by weight, based on the total weight of the total solids in the composition, of calcium;

less than 1 ppm by weight, based on the total weight of the total solids in the composition, of iron;

less than 50 ppm by weight, based on the total weight of the total solids in the composition, of sulfur; and

ash in an amount up to 0.25% by weight, based on the total weight of the total solids in the composition; and

(d) furfural in an amount up to 10% by weight, based on the total weight of the total solids in the composition;

wherein the composition is provided as an aqueous solution.

15. The composition of claim 14 , wherein one or more of the water-soluble monomeric hydrolyzates is a pentose and one or more of the water-soluble dimeric or higher oligomeric hydrolyzate is a pentose.

16. The composition of claim 14 , wherein the impurities comprise Ca, Cu, Fe, K, Mg, Mn, Na, P, S, and Si.

17. The composition of claim 14 , wherein:

the water-soluble monomeric hydrolyzate is selected from xylose, arabinose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from a dimer or higher oligomer of xylose, arabinose, or a combination thereof.

18. The composition of claim 14 , wherein one or more of the hydrolyzates is a hexose.

19. A composition comprising:

(a) at least one water-soluble monomeric hydrolyzate comprising a monomeric hemicellulose sugar hydrolyzate;

(b) at least one water-soluble dimeric or higher oligomeric hydrolyzate comprising a dimeric or higher oligomeric hemicellulose sugar hydrolyzate;

(c) sulfur in an amount up to 50 ppm by weight, based on the total weight of the total solids in the composition; and

(d) furfural in an amount up to 10% by weight, based on the total weight of the total solids in the composition;

wherein the composition is provided as an aqueous solution.

20. The composition of claim 19 , wherein one or more of the water-soluble monomeric hydrolyzates is a pentose and one or more of the water-soluble dimeric or higher oligomeric hydrolyzate is a pentose.

21. The composition of claim 19 , wherein:

the water-soluble monomeric hydrolyzate is selected from xylose, arabinose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from a dimer or higher oligomer of xylose, arabinose, or a combination thereof.

22. The composition of claim 19 , comprising less than 0.25% in total by weight, relative to the total solids in the composition, of ash.

23. The composition of claim 22 , wherein the ash comprises Ca, Cu, Fe, K, Mg, Mn, Na, P, S, and Si.

24. A composition comprising:

at least one water-soluble monosaccharide hydrolyzate;

at least one water-soluble disaccharide hydrolyzate;

ash in an amount up to 0.25% in total by weight, relative to the total solids in the composition; and

furfural in an amount up to 10% by weight, based on the total weight of the total solids in the composition;

wherein the composition is provided as an aqueous solution comprising at least 40% dissolved solids, and

wherein one or more of the water-soluble monosaccharide hydrolyzates is a pentose and one or more of the water-soluble disaccharide hydrolyzates comprises a pentose.

25. The composition of claim 24 , wherein the ash comprises Ca, Cu, Fe, K, Mg, Mn, Na, P, S, and Si.

26. The composition of claim 24 , wherein the composition comprises at least 70% hemicellulose sugars and 20% to 60% cellulose sugars relative to total sugars.

27. A composition comprising:

at least one water-soluble C5 monosaccharide hydrolyzate;

at least one water-soluble C5 oligosaccharide hydrolyzate that is a dimer or higher oligomer;

ash in an amount up to 0.25% in total by weight, relative to the total solids in the composition; and

furfural in an amount up to 10% by weight, based on the total weight of the total solids in the composition;

wherein the composition is provided as an aqueous solution.

28. The composition of claim 27 , wherein the ash comprises Ca, Cu, Fe, K, Mg, Mn, Na, P, S, and Si.

29. A composition, comprising:

at least one water-soluble C5 monosaccharide hydrolyzate;

at least one water-soluble C5 disaccharide hydrolyzate;

impurities, wherein the impurities comprise:

less than 1 ppm by weight, based on the total weight of the total solids in the composition, of calcium;

less than 1 ppm by weight, based on the total weight of the total solids in the composition, of iron;

less than 50 ppm by weight, based on the total weight of the total solids in the composition, of sulfur; and

ash in an amount up to 0.25% by weight, based on the total weight of the total solids in the composition; and

furfural in an amount up to 10% by weight, based on the total weight of the total solids in the composition;

wherein the composition is provided as an aqueous solution.

30. A composition, comprising:

at least one water-soluble monomeric sugar hydrolyzate selected from xylose, arabinose, or a combination thereof;

at least one water-soluble dimeric or higher oligomeric sugar hydrolyzate selected from a dimer or higher oligomer of xylose, arabinose, or a combination thereof;

ash in an amount up to 0.25% in total by weight, relative to the total solids in the composition; and

furfural in an amount up to 10% by weight, based on the total weight of the total solids in the composition;

wherein the composition is provided as an aqueous solution.

31. A composition comprising:

(a) at least one water-soluble monomeric hydrolyzate selected from:

(i) a monomeric hemicellulose sugar hydrolyzate; or

(ii) a monomeric cellulose sugar hydrolyzate;

(b) at least one water-soluble dimeric or higher oligomeric hydrolyzate selected from:

(iii) a dimeric or higher oligomeric hemicellulose sugar hydrolyzate; or

(iv) a dimeric or higher oligomeric cellulose sugar hydrolyzate;

(c) ash in an amount up to 0.25% in total by weight, relative to the total solids in the composition; and

(d) furfural in an amount up to 10% by weight, based on the total weight of the total solids in the composition;

wherein the composition is provided as an aqueous solution comprising at least 40% dissolved solids,

and wherein the water-soluble monomeric hydrolyzate is derived from a lignocellulose substrate.

32. The composition of claim 31 , wherein the ash comprises Ca, Cu, Fe, K, Mg, Mn, Na, P, S, and Si.

33. The composition of claim 31 , wherein:

the water-soluble monomeric hydrolyzate is selected from glucose, mannose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from a dimer or higher oligomer of glucose, mannose, or a combination thereof.

34. The composition of claim 31 , wherein:

the water-soluble monomeric hydrolyzate is selected from glucose, mannose, galactose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from cellobiose, isomaltose, trehalose, or a combination thereof.

35. The composition of claim 31 , wherein:

the water-soluble monomeric hydrolyzate is selected from glucose, mannose, galactose, fructose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from cellobiose, isomaltose, trehalose, or a combination thereof.

36. The composition of claim 31 , wherein the water-soluble monomeric hydrolyzate is present at a concentration of at least 90% in an aqueous solution.

37. The composition of claim 31 , wherein the water-soluble monomeric hydrolyzate is glucose, galactose, mannose, fructose, or a mixture thereof.

38. The composition of claim 31 , further comprising ash in an amount up to 0.10% by weight, relative to the total solids in the composition.

39. The composition of claim 38 , wherein:

the water-soluble monomeric hydrolyzate is selected from xylose, arabinose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from a dimer or higher oligomer of xylose, arabinose, or a combination thereof.

40. The composition of claim 31 , further comprising less than 1 ppm by weight, based on the total weight of the total solids in the composition, of calcium.

41. The composition of claim 40 , wherein:

the water-soluble monomeric hydrolyzate is selected from xylose, arabinose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from a dimer or higher oligomer of xylose, arabinose, or a combination thereof.

42. The composition of claim 31 , further comprising less than 1 ppm by weight, based on the total weight of the total solids in the composition, of iron.

43. The composition of claim 42 , wherein:

the water-soluble monomeric hydrolyzate is selected from xylose, arabinose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from a dimer or higher oligomer of xylose, arabinose, or a combination thereof.

44. The composition of claim 31 , further comprising less than 50 ppm by weight, based on the total weight of the total solids in the composition, of sulfur.

45. The composition of claim 44 , wherein:

the water-soluble monomeric hydrolyzate is selected from xylose, arabinose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from a dimer or higher oligomer of xylose, arabinose, or a combination thereof.

46. The composition of claim 31 , wherein the weight ratio of the water-soluble monomeric hydrolyzate to the ash is greater than 360:1.

47. The composition of claim 31 , comprising at least one dimeric hydrolyzate.

48. The composition of claim 31 , wherein one or more of the hydrolyzates is a hexose.

49. The composition of claim 31 , wherein one or more of the hydrolyzates is a pentose.

50. The composition of claim 31 , wherein:

the water-soluble monomeric hydrolyzate is selected from xylose, arabinose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from a dimer or higher oligomer of xylose, arabinose, or a combination thereof.

51. A composition comprising:

(a) at least one water-soluble monomeric hydrolyzate selected from:

(i) a monomeric hemicellulose sugar hydrolyzate; or

(ii) a monomeric cellulose sugar hydrolyzate;

(b) at least one water-soluble dimeric or higher oligomeric hydrolyzate selected from:

(iii) a dimeric or higher oligomeric hemicellulose sugar hydrolyzate; or

(iv) a dimeric or higher oligomeric cellulose sugar hydrolyzate;

(c) impurities, wherein the impurities comprise:

less than 1 ppm by weight, based on the total weight of the total solids in the composition, of calcium;

less than 1 ppm by weight, based on the total weight of the total solids in the composition, of iron;

less than 50 ppm by weight, based on the total weight of the total solids in the composition, of sulfur; and

ash in an amount up to 0.10% by weight, based on the total weight of the total solids in the composition, wherein the ash comprises Ca, Cu, Fe, K, Mg, Mn, Na, P, S, and Si; and

(d) furfural in an amount up to 10% by weight, based on the total weight of the total solids in the composition;

wherein the composition is provided as an aqueous solution comprising at least 40% dissolved solids.

52. The composition of claim 51 , wherein:

the water-soluble monomeric hydrolyzate is selected from glucose, mannose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from a dimer or higher oligomer of glucose, mannose, or a combination thereof.

53. The composition of claim 51 , wherein:

the water-soluble monomeric hydrolyzate is selected from glucose, mannose, galactose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from cellobiose, isomaltose, trehalose, or a combination thereof.

54. The composition of claim 51 , wherein:

the water-soluble monomeric hydrolyzate is selected from glucose, mannose, galactose, fructose, or a combination thereof; and

the water-soluble dimeric or higher oligomeric hydrolyzate is selected from cellobiose, isomaltose, trehalose, or a combination thereof.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 4, 2024
From: VIRDIA LLC
To: INTERNATIONAL N&H DENMARK APS
Reel/Frame 069873/0615 →
CHANGE OF NAME Recorded Mar 18, 2021
From: VIRDIA, INC.
To: VIRDIA, LLC
Reel/Frame 055633/0305 →
RELEASE OF SECURITY INTEREST Recorded Mar 12, 2021
From: TRIPLEPOINT CAPITAL LLC
To: VIRDIA, INC.
Reel/Frame 055599/0793 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2015
From: EYAL, AHARON; JANSEN, ROBERT P.
To: VIRDIA, INC.
Reel/Frame 035757/0011 →