Alkyl Lactyllactate Solvent Production via Catalytic Transesterification

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Solution Overview

Problem

Existing processes for producing alkyl lactyllactates require solvents, high temperatures, and do not account for chirality or the effects of alkoxylation on product yield and properties, leading to suboptimal yields and purities.

Innovation Solution

A solvent-free process at lower temperatures using a catalyst to produce alkyl lactyllactates with controlled chirality, achieving high yields and purities by reacting lactide with a hydroxyl-containing compound, and utilizing lactic acid with a higher ratio of lactyllactate to lactate.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional Claborn process is used to produce alkyl lactyllactate, then the reaction can proceed, but it requires solvents, high temperatures (above 70°C), and produces suboptimal yields and purities

Engineering Contradiction:
Improveyield and purity of alkyl lactyllactateVSAvoidreaction temperature
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent changes the reaction parameters by using a catalyst system (metal complex with ligands) that enables the reaction to proceed at lower temperatures while achieving higher yields and purities. The catalyst facilitates the transesterification reaction between lactide and alcohol without requiring excessive thermal energy, thus resolving the contradiction between temperature and productivity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a catalyst as an intermediary substance that mediates the reaction between lactide and alcohol. This catalyst (metal complex with specific ligands) provides an alternative reaction pathway with lower activation energy, allowing the reaction to proceed efficiently at lower temperatures without requiring solvents, thereby improving both yield and purity while reducing temperature requirements.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If conventional Claborn process is used, then alkyl lactyllactate can be produced, but it requires additional solvents and inert organic liquids, increasing process complexity

Engineering Contradiction:
Improveyield of alkyl lactyllactateVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent extracts and eliminates the need for solvents and inert organic liquids from the reaction system. By using a catalytic system that facilitates the reaction without requiring solvent media, the process becomes simpler and more direct, achieving high yields while reducing process complexity and eliminating unnecessary components from the reaction mixture.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent employs a self-sufficient catalytic system that enables the reaction to proceed without external assistance from solvents or inert substances. The catalyst system facilitates the transesterification reaction directly between lactide and alcohol, making the process autonomous and eliminating the need for additional process components, thus improving productivity while simplifying the overall process.

Inventive Principle:
Principle #25Self-service

3Manufacturing precision

If conventional process is used, then reaction can proceed, but it does not account for chirality or alkoxylation effects, leading to suboptimal product properties

Engineering Contradiction:
Improvepurity of alkyl lactyllactateVSAvoidprocess simplicity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent applies local quality control by using chiral catalysts or chiral ligands that selectively promote the formation of specific enantiomers or diastereomers of alkyl lactyllactate. This allows precise control over the chiral properties of the product while maintaining process simplicity, achieving high manufacturing precision for products with specific stereochemical configurations.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent changes the chemical parameters of the catalyst system to account for chirality and alkoxylation effects. By selecting specific metal complexes with chiral ligands or modifying the catalyst structure, the process can selectively produce alkyl lactyllactate with desired chiral properties and improved purity, while the catalytic mechanism remains relatively simple and easy to manufacture.

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 significantly increases the yield and purity of alkyl lactyllactates, allowing for improved performance in applications such as oil field and cleaning agents without the need for additional volatile components.

Implementation Method 1

A solvent-free process at lower temperatures using a catalyst to produce alkyl lactyllactates with controlled chirality

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

reacting lactide with a hydroxyl-containing compound

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentUS9174923B2Alkyl lactyllactate solvent compositions
Publication Date: 2015.11.03 STEPAN COMPANY
  • US9174923B2 patent drawing
  • US9174923B2 patent drawing
  • US9174923B2 patent drawing

AI summary

Alkyl lactyllactate and alkoxylated alkyl lactyllactate compounds that are useful as solvents in a variety of applications are disclosed. The compounds are derived from a hydroxyl containing compound and a lactide or lactic acid source that has a specific chirality. The alkyl lactyllactate and alkoxylated alkyl lactyllactate compounds are particularly suitable for use as solvents in applications requiring cold tolerance performance without inclusion of additional volatile components.