Cellulose Conversion via Ylide Catalysis and CMC Intermediary

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Solution Overview

Problem

Current methods for converting cellulose into simple sugars, such as glucose, are inefficient, particularly for crystalline cellulose which is not soluble in water, hindering large-scale biofuel production.

Innovation Solution

Contacting cellulose with compounds containing ylide functionality, such as vitamins, porphyrins, and flavins, under specific pH and temperature conditions to catalytically cleave ether bonds and produce glucose, including the use of carboxymethyl cellulose made by reacting crystalline cellulose with chloroacetic acid and a base, enhancing water solubility and reaction efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If strong acid is used to break up amorphous regions of cellulose, then crystalline cellulose can be produced, but the hydrolysis step becomes particularly slow due to insolubility of crystalline cellulose in water

Engineering Contradiction:
Improvecrystalline structure of celluloseVSAvoidhydrolysis rate
Core Design Contradiction:
Stability of the object's compositionVSProductivity

Solution Approach 1:

The patent uses carboxymethyl cellulose (CMC) as an intermediary substance to facilitate the conversion of crystalline cellulose to glucose. CMC acts as a mediator that can be hydrolyzed more readily than crystalline cellulose itself, providing a pathway around the insolubility problem. The CMC is produced by reacting crystalline cellulose with chloroacetic acid and base, creating a water-soluble intermediate that can then be efficiently hydrolyzed to glucose.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Quantity of substance

If crystalline cellulose is used for biofuel production, then natural resource utilization is improved, but the conversion efficiency is reduced due to slow hydrolysis

Engineering Contradiction:
Improvecellulose availabilityVSAvoidconversion efficiency
Core Design Contradiction:
Quantity of substanceVSProductivity

Solution Approach 1:

The patent changes the chemical parameters of cellulose by converting it to carboxymethyl cellulose through etherification with chloroacetic acid. This chemical modification alters the solubility and reactivity parameters of cellulose, making it suitable for efficient hydrolysis while maintaining the ability to utilize abundant natural cellulose resources.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If continuous large scale processes are implemented for cellulose conversion, then production capacity is improved, but process complexity and cost increase

Engineering Contradiction:
Improveproduction scaleVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent performs preliminary action by pre-converting crystalline cellulose to carboxymethyl cellulose before the hydrolysis step. This preliminary etherification step simplifies the subsequent hydrolysis process, enabling more straightforward continuous processing at large scale without requiring complex equipment to handle the recalcitrant crystalline cellulose directly.

Inventive Principle:
Principle #10Preliminary action

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

This method effectively breaks down cellulose into glucose, improving the solubility and hydrolysis of crystalline cellulose, enabling more efficient production of biofuels by producing glucose under both acidic and alkaline conditions, with elevated temperatures and enzyme breakers aiding in the process.

Implementation Method 1

contacting cellulose with a compound effective to catalytically cleave the ether bonds of the cellulose to give at least one simple sugar

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

The slow step in converting cellulose to fuel is the hydrolysis

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 3

treating the fibers or sheet materials containing the remainder of the aqueous alkaline reaction mixture with heat energy

Methodology Applied
Scientific EffectHeating: Heating

Data Source

PatentUS9790251B2Conversion of cellulose into simple sugars
Publication Date: 2017.10.17 BAKER HUGHES CO
  • US9790251B2 patent drawing

AI summary

Cellulose may be converted into simple sugars such as glucose by contacting the cellulose with a compound effective to catalytically cleave the ether bonds of the cellulose. The compound may be a vitamin, a porphyrin, flavins, pyridoxal-containing molecules, and/or a compound containing at least one ylide functional group. The cellulose may be carboxymethyl cellulose (CMC), which may be made by reacting cellulose with chloroacetic acid and a base such as NaOH. The compound may be vitamins (B1, B2, B6, or B12), phosphonium ylides, sulfonium ylides, sulfoxonium ylides, carbonyl ylides, oxonium ylides, asomethine ylides, iminium ylides, halonium ylides, and combinations thereof. The free glucose may be used for fermentation, converted to a biofuel and for other applications.