Water Concentration Reduction in Adipic Acid Production

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current methods for converting biorenewable resources like glucose into adipic acid face challenges in selectively removing oxygen atoms, leading to inefficiencies and high costs due to the production of excess water in hydrodeoxygenation reactions.

Innovation Solution

A process that involves converting glucose to a hydrodeoxygenation substrate with a reduced water concentration, typically below 15% by weight, using techniques such as chromatography, distillation, or pervaporation, followed by hydrodeoxygenation with a catalyst like Ru, Rh, or Pd to produce adipic acid, thereby reducing capital and operating costs.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional hydrodeoxygenation processes are used to convert glucose to adipic acid, then the conversion of biorenewable resources to chemical products is achieved, but excess water is produced leading to high purification costs and reduced process efficiency

Engineering Contradiction:
Improveadipic acid production efficiencyVSAvoidexcess water production
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent applies preliminary action by performing water removal operations (evaporation, distillation, or extraction) on the reaction mixture before the hydrodeoxygenation step. This pre-concentration of the glucaric acid substrate reduces the water content entering the hydrodeoxygenation reactor, thereby minimizing excess water production during the conversion to adipic acid and reducing downstream purification requirements

Inventive Principle:
Principle #10Preliminary action

2Ease of manufacture

If water concentration is reduced in the hydrodeoxygenation feedstock, then purification costs and capital expenses are reduced, but additional water removal steps are required adding process complexity

Engineering Contradiction:
Improvepurification costVSAvoidwater removal equipment
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent applies the extraction principle by using extraction techniques (such as liquid-liquid extraction with organic solvents) to remove water from the reaction mixture. This selectively extracts and separates water from the glucaric acid and other components, effectively reducing water concentration in the feedstock for subsequent hydrodeoxygenation while providing a relatively simple operational procedure

Inventive Principle:
Principle #2Taking out (Extraction)

3Productivity

If conventional oxidation processes are used to convert glucose to glucaric acid, then the conversion is achieved but 1 mole of water is produced per mole of glucaric acid stoichiometrically

Engineering Contradiction:
Improveglucaric acid conversion efficiencyVSAvoidstoichiometric water production
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent applies the 'blessing in disguise' principle by converting the harmful effect of stoichiometric water production into a benefit. The water produced during oxidation is deliberately utilized in the subsequent steps: it serves as the solvent medium for extraction operations and can be recovered and reused in the oxidation step, thereby transforming a waste product into a valuable resource that reduces the need for additional water input and minimizes overall water consumption in the process

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 process enhances the yield and selectivity of adipic acid production, reduces downstream purification costs, and improves the economic viability of adipic acid production from biorenewable sources.

Implementation Method 1

converting a feed comprising glucose to a reaction product comprising a hydrodeoxygenation substrate and water in a concentration on a weight basis equal to or less than about 15%, wherein the hydrodeoxygenation substrate comprises a compound of formula I: wherein X is independently hydroxyl, oxo, halo, acyloxy or hydrogen provided that at least one X is not hydrogen and R1 wherein R1

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

The step of reducing the concentration of water may be carried out using a technique selected from the group consisting of chromatography, distillation, evaporation, extraction, desiccation, membrane separation, pervaporation, and combinations thereof

Methodology Applied
Scientific EffectChromatography: Chromatography

Implementation Method 3

The step of reducing the concentration of water may be carried out using a technique selected from the group consisting of chromatography, distillation, evaporation, extraction, desiccation, membrane separation, pervaporation, and combinations thereof

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 4

The step of reducing the concentration of water may be carried out using a technique selected from the group consisting of chromatography, distillation, evaporation, extraction, desiccation, membrane separation, pervaporation, and combinations thereof

Methodology Applied
Scientific EffectPervaporation: Pervaporation

Implementation Method 5

Such processes include the steps of catalytic oxidation of the glucose-containing feed to glucaric acid and/or derivatives thereof followed by catalytic hydrodeoxygenation of glucaric acid and/or derivatives thereof to an adipic acid product

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentEP2791104B1Water concentration reduction process
Publication Date: 2018.01.10 ARCHER DANIELS MIDLAND CO
  • EP2791104B1 patent drawingFigure 1
  • EP2791104B1 patent drawingFigure 2
  • EP2791104B1 patent drawing

AI summary

The present disclosure relates generally to water concentration reduction processes within an adipic acid process. The present invention also includes process for converting a glucose-containing feed derived from a carbohydrate source to an adipic acid product wherein the process includes the steps of: converting glucose in the feed to a reaction product including a hydrodeoxygenation substrate and a first concentration of water; reducing the concentration of water in the reaction product to produce a feedstock including the hydrodeoxygenation substrate and second concentration of water, wherein the second concentration of water is less than the first concentration of water; and converting at least a portion of the hydrodeoxygenation substrate in the feedstock to an adipic acid product. Processes are also disclosed for producing hexamethylene diamine and caprolactam from the adipic acid product.