IP Library Patent Application 14890433
Patent Application
App. No. 14/890,433

PROCESS TO PREPARE LEVULINIC ACID

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Quick Facts
Patent No.
US None
App. No.
14/890,433
Abstract

The invention describes processes to prepare levulinic acid, formic acid and/or hydroxymethyl furfural from various biomass materials.

Claims (22)

1 - 39 . (canceled)

40 . A composition comprising a material derived from a polysaccharide, fructose, glucose and/or sucrose having a carbonyl stretch, C═O, at 1704 cm −1 , unsaturated and/or aromatic C═C stretches at 1617 cm −1 and 1514 cm −1 , an absorption peak at 1023 cm −1 , related to a C—O stretch, measured by ATR-IR, wherein IR absorption ratios are less than 1.6, preferably less than 1.4, and more preferable less than 1.2 ratio for C═O 1704 cm −1 /C═C 1617 cm −1 , and/or less than 3, preferably less than 2, and more preferable less than 1.5 for C═O 1704 cm −1 /C═C 1514 cm −1 , and/or less than 1.8, preferably less than 1.6, and more preferable less than 1.4 ratio for C═O 1704 cm −1 /C—O 1023 cm −1 .

41 . The composition of claim 40 , wherein the composition is non-sticky to metal, plastic, or glass.

42 . The composition of claim 40 , wherein the composition is granular or a powder.

43 . A reactive distillation process comprising the steps of:

combining levulinic acid, optionally water and a monohydroxy alcohol in a reactive distillation column comprising a suspended or packed bed of catalyst to form a mixture;

heating the mixture in the reactive distillation column to effect esterification of the levulinic acid to afford the levulinic ester; and

separating the levulinic ester from the mixture and byproducts.

44 . The process of claim 43 , further comprising removing removal metal ions from the reaction mixture components prior to the reactive distillation process.

45 . The process of claim 44 , wherein the metal ions are removed prior to the reactive distillation process by cation exchange resins.

46 . The process of claim 43 , further comprising removing oligomers and solvents by adsorption or adsorption via carbon bed from the reaction mixture components prior to the reactive distillation process.

47 . The process of claim 43 , further comprising removing strong acid impurities using anion exchange resins, weak bases, or molecular sieves from the reaction mixture components prior to the reactive distillation process.

48 . The process of claim 43 , further comprising treating the levulinic acid or ester with molecular sieves or an alkali or alkaline metal base to remove any strong acid impurities from the levulinic ester.

49 . The process of claim 43 , further comprising the step of washing the levulinic acid with water prior to reactive distillation and/or washing the levulinic ester with water, to remove water soluble impurities, such as strong acids.

50 . The process of claim 49 , wherein the strong acid is sulfuric acid, hydrochloric acid, perchloric acid, triflic acid, para-toluene sulfonic acid, naphthalene sulfonic acid, or hydrobromic acid.

51 . The process of claim 43 , further comprising the step of removing alpha and beta angelica lactone and/or a 4-alkoxy-gamma valerolactone impurities by distillation or by conversion to other compounds followed by distillation, or by adsorption with a suitable absorption media.

52 . A method to reduce the concentration of sulfuric acid in an organic extraction solvent containing levulinic acid comprising the steps:

treating a mixture comprising an organic solvent containing levulinic acid and sulfuric acid with an aqueous solution of dilute sulfuric acid, wherein the dilute sulfuric acid is present in the aqueous solution between 0.01-15 weight percent;

separating the organic solvent portion containing the levulinic acid from the aqueous portion to provide a final levulinic acid solution comprising a reduced amount of sulfuric acid contained in the organic solvent.

53 . The method of claim 52 , wherein the final concentration of sulfuric acid in the organic solvent portion is from about 0.001 to about 0.25 weight percent.

54 . The method of claim 52 , wherein the mixture further comprises formic acid.

55 . The method of claim 52 further comprising treating the extract stream containing levulinic acid with an anion exchange resin, weak base, or buffer.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2016
From: SEGETIS, INC.
To: GFBIOCHEMICALS LIMITED
Reel/Frame 038380/0148 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 18, 2016
From: BADARINARAYANA, VIVEK; RODWOGIN, MARC D.; MULLEN, BRIAN D.; PURTLE, IAN; MOLITOR, ERICH J.
To: SEGETIS, INC.
Reel/Frame 038303/0580 →