Vegetable Oil Polyol Synthesis via Microchannel Ring-Opening

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Solution Overview

Problem

Vegetable oil polyols face challenges due to high functionality and uncontrollable reaction processes, leading to poor molecular uniformity, high viscosity, and performance deficiencies, making it difficult to replace traditional petrochemical polyols effectively in bio-based polyurethane coating materials.

Innovation Solution

A method involving a polyfunctional ring-opening reagent with mercapto and hydroxyl groups for controlled ring-opening reactions in a microchannel reaction device, using β-mercaptoalcohol and cyclohydrocarbyl methanol as reagents to retain epoxy groups and introduce antioxidant sulfur-containing fragments, ensuring controlled reaction conditions and improved molecular structure.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If conventional ring-opening reaction methods are used on epoxidized vegetable oil, then the reaction process is simple and easy to operate, but the reaction process becomes uncontrollable, leading to poor molecular uniformity and high viscosity

Engineering Contradiction:
Improveease of operationVSAvoidmolecular uniformity
Core Design Contradiction:
Ease of operationVSManufacturing precision

Solution Approach 1:

The patent applies parameter changes by precisely controlling reaction conditions including temperature (60-80°C), residence time (5-15 minutes), and molar ratios of reactants. The microchannel reaction device enables precise parameter control that transforms the uncontrollable conventional process into a controlled process, achieving uniform molecular structure while maintaining ease of operation through automated precision control.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a catalyst as an intermediary substance to mediate the ring-opening reaction. The catalyst enables selective and controlled reaction between epoxidized vegetable oil and ring-opening agents, improving molecular uniformity without complicating the operational process. The catalyst acts as a mediator that facilitates the desired chemical transformation while maintaining process simplicity.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If multiple functional groups are introduced to improve antioxidant properties, then oxidation resistance is enhanced, but the reaction selectivity decreases and process controllability deteriorates

Engineering Contradiction:
Improveoxidation resistanceVSAvoidprocess controllability
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent applies preliminary action by pre-introducing antioxidant functional groups (sulfur-containing groups) into the polyol molecular structure through controlled ring-opening reactions before polyurethane synthesis. This preliminary incorporation of antioxidant groups ensures oxidation resistance in the final product while maintaining process controllability through the use of microchannel reaction technology that prevents unwanted side reactions.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent applies local quality by introducing sulfur-containing antioxidant groups at specific locations within the polyol molecular structure through selective ring-opening reactions. Rather than uniformly modifying all functional groups, the method selectively introduces antioxidant groups where needed, maintaining both oxidation resistance and process controllability through localized functional group modification.

Inventive Principle:
Principle #3Local quality

3Ease of manufacture

If traditional chemical methods are used for polyol synthesis, then the process is straightforward, but side reactions occur frequently, making it difficult to construct the desired molecular structure

Engineering Contradiction:
Improveease of manufactureVSAvoidmolecular structure construction
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent replaces conventional mechanical mixing and heating methods with a microchannel reaction device that uses controlled fluid flow and heat transfer. This substitution enables precise control over reaction conditions, reducing side reactions and improving molecular structure construction while maintaining ease of manufacture through automated flow control and efficient heat exchange.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

Solution Approach 2:

The patent applies periodic action through controlled residence time in the microchannel reactor (5-15 minutes). The reactants are continuously fed and reacted for a precise duration, then discharged. This periodic control of reaction time prevents over-reaction and side reactions, enabling accurate molecular structure construction while maintaining continuous production and ease of manufacture.

Inventive Principle:
Principle #19Periodic 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

The method results in vegetable oil polyols with improved uniformity, reduced viscosity, and enhanced antioxidant and anticorrosion properties, enabling the production of high-performance polyurethane coating materials that can replace traditional petrochemical-based products.

Implementation Method 1

using microreaction technology to intensify the chemical reaction process and achieve continuous and precise control

Methodology Applied
Scientific EffectHeat transfer: Conduction (thermal)

Implementation Method 2

the main reason is the poor miscibility between the oil ester and the reaction reagents, along with relatively low reactivity

Methodology Applied
Scientific EffectMass transfer: Diffusion

Implementation Method 3

a polyfunctional ring-opening reagent having groups such as mercapto and hydroxyl groups is used as a first ring-opening reagent to complete a ring-opening reaction of epoxy groups

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentUS20240417504A1Vegetable oil polyol, preparation method therefor, and use thereof
Publication Date: 2024.12.19 CHINA CONSTRUCTION INDUSTRIAL & ENERGY ENGINEERING GROUP CO LTD
  • US20240417504A1 patent drawing
  • US20240417504A1 patent drawing
  • US20240417504A1 patent drawing

AI summary

An epoxidized vegetable oil is subjected to a first ring-opening reaction with an acidic catalyst and a β-mercaptoalcohol compound to obtain a first reaction solution, and then the first reaction solution is subjected to a second ring-opening reaction with a cyclohydrocarbyl methanol compound to obtain the vegetable oil polyol, which adopts novel ring-opening reagents to introduce an antioxidant sulfur-containing fragment into the molecular structure of the vegetable oil polyol in a covalent manner, while also introducing a cyclohydrocarbyl group and retaining a small portion of epoxy groups, thereby ensuring that a polyurethane product has a certain degree of toughness, in addition to relatively good corrosion resistance and oxidation resistance, while guaranteeing the mechanical properties of the polyurethane material.