Levulinic Acid Purification via Melt Crystallization

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Solution Overview

Problem

Current methods for purifying levulinic acid, such as distillation and crystallization, often result in impurities like angelica lactone, formic acid, and low shelf stability, and are inefficient due to unpredictable melt crystallization processes and the need for solvents or low temperature cooling, which complicates the purification of levulinic acid to the desired 95-99% purity required for pharmaceutical and cosmetic applications.

Innovation Solution

A melt crystallization process involving a composition with at least 75% levulinic acid, cooled to a specific temperature range, and contacted with levulinic acid crystal seeds to crystallize, followed by optional sweating and repeated cycles to achieve a purity of at least 98% without occluding impurities, reducing energy consumption and ensuring clear, stable product.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If distillation is used to purify levulinic acid, then concentration is improved, but impurities like angelica lactone are formed causing coloration and low shelf stability

Engineering Contradiction:
Improvelevulinic acid concentrationVSAvoidangelica lactone formation
Core Design Contradiction:
Quantity of substanceVSObject-generated harmful factors

Solution Approach 1:

The patent applies melt crystallization, a phase transition process, to purify levulinic acid. The crude levulinic acid composition is cooled to crystallize pure levulinic acid while leaving impurities in the liquid phase. This resolves the contradiction by achieving high concentration through crystallization rather than distillation, thereby avoiding angelica lactone formation while obtaining pure product.

Inventive Principle:
Principle #36Phase transitions

2Manufacturing precision

If crystallization is used to purify levulinic acid, then purity is improved, but the process becomes unpredictable and complex

Engineering Contradiction:
Improvelevulinic acid purityVSAvoidcrystallization process complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent applies preliminary action by pre-cooling the crude levulinic acid composition to a temperature below its melting point before adding crystal seeds. This preliminary cooling step ensures that the subsequent crystallization process proceeds predictably and efficiently, reducing process complexity while achieving high purity.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses crystal seeds as an intermediary to initiate and control the crystallization process. By adding pre-formed levulinic acid crystals to the cooled crude composition, the process becomes predictable and controllable, eliminating the unpredictability associated with spontaneous crystallization while maintaining high purity.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Manufacturing precision

If crystallization from diluted levulinic acid is used, then purity is improved, but low temperatures and solvents are required increasing complexity

Engineering Contradiction:
Improvelevulinic acid purityVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by working with concentrated levulinic acid composition (at least 75 wt% purity) rather than diluted solutions. The process uses cooling to a specific temperature range (0°C to 20°C below melting point) without requiring solvents, thereby achieving high purity while simplifying the process by eliminating solvent recovery steps and extreme temperature requirements.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The process effectively reduces impurities, achieves high purity levulinic acid with trace amounts of formic acid and no angelica lactone, ensuring long shelf life and clear composition, while simplifying the operation by avoiding strong undercooling and solvent use, thus meeting the purity requirements for pharmaceutical and cosmetic applications.

Implementation Method 1

Cooling composition 1 to at least one temperature Tc, wherein Tc is a temperature in the range 1.23*(W1) -104.5 ≤ Tc (°C) ≤ 1.23*(W1) - 89.5, wherein W1 is the weight% of levulinic acid in composition 1

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 2

Cooling composition 1 to at least one temperature Tc to obtain a cooled composition 1

Methodology Applied
Scientific EffectFreezing: Freezing

Implementation Method 3

Bringing the cooled composition 1 into contact with levulinic acid crystal seeds

Methodology Applied
Scientific EffectNucleation: Nucleation

Implementation Method 4

Draining of liquid 1

Methodology Applied
Scientific EffectSedimentation: Sedimentation

Implementation Method 5

Heating the crystals 1 at a temperature between 5 and 40 °C to obtain crystals 2 and liquid 2

Methodology Applied
Scientific EffectMelting: Melting

Data Source

PatentEP3362430B1Process for the purification of levulinic acid
Publication Date: 2020.11.25 GFBIOCHEM IP ASSETS BV
  • EP3362430B1 patent drawingFigure 1~2

AI summary

The invention is directed to a process for the purification of levulinic acid comprising the following steps: a. Providing a composition 1, comprising at least 75 wt% of levulinic acid; b. Cooling composition 1 to at least one temperature Tc, wherein Tc is a temperature in the range 1.23*(W1) -104.5‰¤ Tc (ºC) ‰¤ 1.23*(W1) - 89.5, wherein W1 is the weight% of levulinic acid in composition 1, to obtain a cooled composition 1; c. Performing melt crystallization of composition 1 comprising the steps of: i. Bringing the cooled composition 1 into contact with levulinic acid crystal seeds, ii. Allowing the levulinic acid in composition 1 to crystallize at at least one temperature Tc to obtain crystals 1 and liquid 1, and iii. Draining of liquid 1; d. Optionally, treating crystals 1, after draining of liquid 1, by sweating, according to the following steps: i. Heating the crystals 1 at a temperature between 5 and 40 ºC to obtain crystals 2 and liquid 2, and ii. Draining of liquid 2; e. Melting the crystals 1 or 2, after draining of liquid 1 or 2, to obtain composition 2, f. Determining the levulinic acid concentration in composition 2 and, in case the levulinic acid concentration is below a predetermined value, repeating steps b, c, optionally d, and e, as many times as necessary to obtain a final composition with a predetermined levulinic acid concentration.