Solketal-ter-amyl-ether Fuel Additive Solubility

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Solution Overview

Problem

Glycerine ethers used as fuel additives face limitations due to inadequate solubility in diesel and gasoline, leading to poor ignition behavior and reduced fuel quality, with existing methods failing to achieve 100% conversion to triethers and resulting in unwanted by-products.

Innovation Solution

The production of solketal-ter-amyl-ether (STAE) through acetalization of glycerine with acetone and subsequent etherification with tertiary olefins, significantly improving solubility and allowing recycling of environmentally unfriendly compounds like glycerine and acetone.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If glycerine ethers are used as fuel additives, then fuel quality improvement is achieved, but solubility in diesel and gasoline is insufficient

Engineering Contradiction:
Improvefuel qualityVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent modifies the chemical structure of glycerine ethers by etherifying hydroxyl groups with tertiary olefins to create solketal-ter-amyl-ether. This parameter change in molecular structure eliminates the hydrophilic hydroxyl groups while maintaining the oxygen-containing functionality, thereby improving solubility in non-polar fuel components while retaining fuel quality enhancement properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite ether structure combining solketal (from glycerine and acetone) with tertiary amyl groups from olefins. This composite molecular structure integrates the oxygen-containing functionality needed for fuel quality improvement with the hydrophobic character required for solubility in diesel and gasoline.

Inventive Principle:
Principle #40Composite materials

2Reliability

If conversion to triethers is increased, then fuel additive performance is improved, but steric hindrance prevents 100% conversion

Engineering Contradiction:
Improveadditive performanceVSAvoidconversion efficiency
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent accepts that 100% conversion to triethers is not achievable due to steric hindrance and designs the process to achieve high conversion (up to 95-98%) through optimized reaction conditions including catalyst selection, temperature control, and reactant ratios. The remaining unreacted materials are recycled back into the reaction system.

Inventive Principle:
Principle #16Partial or excessive action

Solution Approach 2:

The invention implements a recycling system where unreacted glycerine, acetone, and light naphtha stream components that are not converted in the etherification reaction are separated and fed back into the reaction system. This recovering approach maximizes overall conversion efficiency and reduces waste.

Inventive Principle:
Principle #34Discarding and recovering

3Productivity

If reaction temperature is increased, then reaction speed is improved, but yield is reduced and oligomerisation occurs

Engineering Contradiction:
Improvereaction speedVSAvoidyield
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent optimizes the reaction temperature parameter to a specific range (60-80°C) that balances reaction kinetics and product stability. This parameter change prevents oligomerisation while maintaining adequate reaction speed through the use of efficient catalyst systems and optimized residence time in the reaction zone.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs a continuous reaction process with optimized flow rates and residence times that maintains the reaction within the optimal temperature window throughout the reactor. This continuous action prevents localized overheating that could lead to oligomerisation while sustaining high productivity through continuous material throughput.

Inventive Principle:
Principle #20Continuity of useful action

4Manufacturing precision

If reaction temperature is decreased, then oligomerisation is reduced, but reaction speed becomes too slow for useful production

Engineering Contradiction:
Improveproduct purityVSAvoidreaction speed
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent introduces catalyst systems as intermediaries that lower the activation energy of the etherification reaction. This allows the reaction to proceed at useful speeds at lower temperatures (60-80°C) without requiring high thermal energy input that would cause oligomerisation. The catalyst acts as a mediator enabling the reaction to occur under milder, more selective conditions.

Inventive Principle:
Principle #24Intermediary (Mediator)

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

STAE exhibits enhanced solubility in diesel and gasoline, improving fuel quality and enabling the recycling of unwanted compounds, thus overcoming the solubility and ignition issues faced by previous glycerine ether-based fuel additives.

Implementation Method 1

The production of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane (solketal) from glycerine and acetone

Methodology Applied
Scientific EffectAcetalization: Chemical Bonding

Implementation Method 2

reacting the 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane produced in step a), or obtained in any other way, with tertiary alkene compounds in order to etherify the remaining OH group

Methodology Applied
Scientific EffectEtherification: Chemical Bonding

Data Source

PatentEP3515899B1Solketal-ethers, production method and uses thereof
Publication Date: 2021.09.01 CEPSA SAU
  • EP3515899B1 patent drawingFigure 1~2
  • EP3515899B1 patent drawingFigure 3(a)~3(b)
  • EP3515899B1 patent drawingFigure 4

AI summary

The present invention describes the use and production of a solketal ether compound of formula (I), in particular solketal-ter-amyl-ether (STAE), in diesel fuels, gasoline, and rapeseed biodiesel, with 5 which the limited solubility of the fuel additive solketal and STBE is significantly increased and whereby products such as glycerine, acetone and light naphtha can be recycled to afford solketal ethers. These improvements are achieved by a) the production of 2,2-dimethyl-4- hydroxymethyl-l,3-dioxolane (solketal) from glycerine and acetone and b) by reacting the 2,2- dimethyl-4- hydroxymethyl-l,3-dioxolane produced in step a), or obtained in any other way, with certain alkene compounds in order to etherify the remaining OH group.