# US 10,369,492 B2 · Process for the isolation of levulinic acid

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- Number: US 10,369,492 B2
- Document ID: US10369492B2
- Status: Granted
- Kind: B2
- Application number: 15/743,115
- Filed: 2016-07-08
- Published: 2019-04-04
- Granted: 2019-08-06
- Earliest claimed: 2015-07-10
- Assignees: Gfbiochemicals IP Assets B.V.
- Applicants: Gfbiochemicals IP Assets B.V.
- Inventors: Aris De Rijke; Rudy Francois Maria Jozef Parton; Donato Santoro
- Web page: https://patentgrep.com/patent/US10369492B2

## CPC

- B01D 3/009: {in combination with chemical reactions}
- B01D 1/26: Multiple-effect evaporating
- C07C 51/44: by distillation
- B01D 2257/70: Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
- C07C 59/185: Saturated compounds having only one carboxyl group and containing keto groups
- Y02P 20/10: Process efficiency
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A process for the isolation of levulinic acid obtained by acid catalyzed hydrolysis of a C6-carbohydrate-containing feedstock, including the following steps: a) providing a solution 1 comprising at least 5 wt. % of levulinic acid, at least 0.1 wt. % of formic acid and at most 94.9 wt. % of solvent, relative to the total weight of solution 1, b) feeding solution 1 to a first evaporation step to treat solution 1 and to obtain solution 2, comprising at least 25 wt. % of levulinic acid, less than 20 wt. % of solvent and at least 1 wt. % of formic acid, relative to the total weight of solution 2, c) feeding solution 2 to a second evaporation step to treat solution 2 and to obtain solution 3, comprising at least 30 wt. % of levulinic acid and less than 1.0 wt. % of formic acid, relative to the total weight of solution 3, d) feeding solution 3 to a third evaporation step to treat solution 3 and to obtain levulinic acid with a purity of at least 90 wt. % and containing less than 1000 wppm angelica lactone.

## Claims

### Claim 1

A process for the isolation of levulinic acid obtained by acid catalyzed hydrolysis of a C6-carbohydrate-containing feedstock, comprising the following steps:
a) providing a solution 1 comprising at least 5 wt. % of levulinic acid, at least 0.1 wt. % of formic acid and at most 94.9 wt % of solvent, relative to the total weight of solution 1,
b) feeding solution 1 to a first evaporation step to treat solution 1 and to obtain solution 2, comprising at least 25 wt. % of levulinic acid, less than 20 wt. % of solvent and at least 1 wt. % of formic acid, relative to the total weight of solution 2,
c) feeding solution 2 to a second evaporation step to treat solution 2 and to obtain solution 3, comprising at least 30 wt. % of levulinic acid and less than 1.0 wt. % of formic acid the total weight of solution 3,
d) feeding solution 3 to a third evaporation step to treat solution 3 and to obtain levulinic acid with a purity of at least 90 wt. % and containing less than 1000 wppm angelica lactone.

### Claim 2 (depends on 1)

The process according to claim 1, wherein each of steps c and d is performed in 1 evaporator or 2 evaporators.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the evaporator or evaporators in the evaporation steps are operated at a liquid temperature between 100 and 200° C.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the evaporator or evaporators in step b are operated at a pressure between 5-500 kPa.

### Claim 5 (depends on 1)

The process according to claim 1, wherein the evaporator or evaporators in step c are operated at a pressure between 1-20 kPa.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the evaporator or evaporators in step d are operated at a pressure between 0.1-7.5 kPa.

### Claim 7 (depends on 1)

The process according to claim 1, wherein one evaporator is present in each evaporation step and the evaporator in the first evaporation step is a forced circulation evaporator, the evaporator in the second evaporation step is a first agitated film evaporator and the evaporator in the third evaporation step is a second agitated thin film evaporator.

### Claim 8 (depends on 1)

The process according to claim 1, wherein levulinic acid in solution 1 is present in an amount of at least 10 wt. %, relative to the total weight of solution 1.

### Claim 9 (depends on 1)

The process according to claim 1, wherein the isolation process is a continuous process.

### Claim 10 (depends on 1)

The process according to claim 1, wherein the solvent is water.

### Claim 11 (depends on 1)

The process according to claim 1, wherein in solution 1 the levulinic acid is present in an amount of at most 60 wt. %.

### Claim 12 (depends on 1)

The process according to claim 1, wherein during purification of reaction product X in step a no liquid-liquid extraction is used.

### Claim 13 (depends on 12)

The process according to claim 12, wherein
a) solution 1 is fed to a forced circulation operated at a pressure between 5-500 kPa and at a liquid temperature between 100 and 200° C.,
b) solution 2 is fed to a first agitated thin film evaporator operated at a pressure between 1-20 kPa and at a liquid temperature between 100 and 200° C. and
c) solution 3 is fed to a second agitated thin film evaporator operated at a pressure between 0.1-7.5 kPa and at a liquid temperature between 100 and 200° C.

### Claim 14 (depends on 3)

The process according to claim 3, wherein the evaporator or evaporators in step b are operated at a pressure between 5-500 kPa, wherein the evaporator or evaporators in step c are operated at a pressure between 1-20 kPa, wherein the evaporator or evaporators in step d are operated at a pressure between 0.1-7.5 kPa, and wherein one evaporator is present in each evaporation step and the evaporator in the first evaporation step is a forced circulation evaporator, the evaporator in the second evaporation step is a first agitated film evaporator and the evaporator in the third evaporation step is a second agitated thin film evaporator.

### Claim 15 (depends on 14)

The process according to claim 14, wherein levulinic acid in solution 1 is present in an amount of at least 10 wt. %, relative to the total weight of solution 1, wherein the isolation process is a continuous process, wherein the solvent is water, wherein in solution 1 the levulinic acid is present in an amount of at most 60 wt. %, and wherein during purification of reaction product X in step a no liquid-liquid extraction is used.