Normal Paraffin Production via Epoxidation and Deoxygenation

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Solution Overview

Problem

Existing methods for producing normal paraffins from unsaturated feeds, such as vegetable and animal oils, often require severe cracking conditions to convert C17 and C18 paraffins into the desired C9 to C15 range, resulting in excessive production of low-octane naphtha and degrading the yield of desired paraffins.

Innovation Solution

The method involves epoxidizing unsaturated feeds with alkenyl groups to form epoxide compounds, which are then converted to hydroxyl-functional compounds and subsequently deoxygenated to produce normal paraffins, avoiding severe cracking conditions and minimizing the production of low-octane naphtha.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If severe cracking conditions are applied to convert C17 and C18 normal paraffins into C9 to C15 normal paraffins, then the desired carbon chain length range is achieved, but excessive amounts of low-octane naphtha (C4 to C8 normal paraffins) are produced, degrading the potential yield

Engineering Contradiction:
Improvecarbon chain length distributionVSAvoidyield of desired C9 to C15 normal paraffins
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The invention changes the chemical parameters of the feedstock by using epoxidized and hydroxyl-functionalized compounds instead of directly cracking normal paraffins. This parameter change allows deoxygenation to produce C9 to C15 normal paraffins directly without requiring severe cracking conditions, thereby avoiding over-cracking to low-octane naphtha while achieving the desired carbon chain length distribution

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention performs preliminary chemical modifications (epoxidation and hydroxyl functionalization) on the unsaturated feed before deoxygenation. This preliminary action creates compounds that, upon deoxygenation, directly yield C9 to C15 normal paraffins in the desired range, eliminating the need for subsequent severe cracking operations that would cause over-cracking and loss of desired product

Inventive Principle:
Principle #10Preliminary action

2Productivity

If hydrogenation/deoxygenation processes are used on vegetable and animal oils, then normal paraffins are produced, but the carbon chain length is limited to diesel range (C17 and C18), requiring additional cracking

Engineering Contradiction:
Improveproduction of normal paraffinsVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention changes the chemical structure parameters of the feedstock by selecting unsaturated compounds with specific carbon chain lengths (corresponding to C9 to C15 after deoxygenation) and applying epoxidation and hydroxyl functionalization. This parameter change enables direct production of jet fuel-range normal paraffins in a single deoxygenation step, avoiding the need for additional cracking processes and reducing overall process complexity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention performs preliminary selection and chemical modification of the feedstock to ensure that deoxygenation directly produces the desired carbon chain length range. By choosing appropriate unsaturated compounds and applying epoxidation/hydroxyl functionalization beforehand, the process eliminates the need for subsequent cracking operations, thereby reducing device complexity while maintaining high productivity

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 approach yields a wider range of normal paraffins, including those with 9 to 15 carbon atoms, reducing the need for severe cracking and minimizing the production of low-octane naphtha, while enabling the production of renewable jet fuel and linear alkyl benzene.

Implementation Method 1

The unsaturated feed is epoxidized to convert the at least one alkenyl group in the unsaturated compound to an epoxide functional group

Methodology Applied
Scientific EffectEpoxidation: Oxidation

Implementation Method 2

The at least one epoxide functional group in the epoxide compound is converted to at least one secondary hydroxyl functional group

Methodology Applied
Scientific EffectHydration of epoxide: Hydrolysis

Implementation Method 3

The hydroxyl-functional compound is deoxygenated to form normal paraffins

Methodology Applied
Scientific EffectDeoxygenation: Hydrogenation

Data Source

PatentUS8916739B2Methods and apparatuses for preparing normal paraffins and hydrocarbon product streams
Publication Date: 2014.12.23 UOP LLC
  • US8916739B2 patent drawing
  • US8916739B2 patent drawing
  • US8916739B2 patent drawing

AI summary

Methods and apparatuses for preparing normal paraffins and hydrocarbon product streams are provided herein. A method of preparing normal paraffins includes providing an unsaturated feed that includes an unsaturated compound that has at least one alkenyl group. The unsaturated feed is epoxidized to convert the at least one alkenyl group in the unsaturated compound to an epoxide functional group, thereby converting the unsaturated compound to an epoxide compound that has at least one epoxide functional group. The at least one epoxide functional group in the epoxide compound is converted to at least one secondary hydroxyl functional group, thereby converting the epoxide compound to a hydroxyl-functional compound that has at least one hydroxyl functional group. The hydroxyl-functional compound is deoxygenated to form normal paraffins.