Caprolactamium Ionic Liquid Nitrogen Removal from Diesel

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Solution Overview

Problem

Current processes face challenges in effectively removing nitrogen compounds from vacuum gas oil (VGO) and diesel fuels, which interferes with the conversion of VGO and the removal of sulfur from diesel fuels, necessitating a more efficient method to reduce nitrogen content.

Innovation Solution

The process involves contacting VGO or diesel fuels with a caprolactamium ionic liquid, which is immiscible with the fuels, to extract and separate nitrogen compounds, thereby reducing the nitrogen content by at least 40 wt%, and potentially recycling the ionic liquid for further use.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If catalytic hydrogenation reactions are used to reduce nitrogen content of VGO, then nitrogen content is reduced, but process complexity and cost increase

Engineering Contradiction:
Improvenitrogen contentVSAvoidprocess complexity
Core Design Contradiction:
Quantity of substanceVSDevice complexity

Solution Approach 1:

The patent applies extraction by selectively dissolving nitrogen-containing compounds from VGO into an ionic liquid phase. The ionic liquid is contacted with the VGO feedstock, nitrogen compounds are extracted into the ionic liquid phase, and the treated VGO is separated. This extraction-based approach replaces complex catalytic hydrogenation processes while achieving effective nitrogen removal.

Inventive Principle:
Principle #2Taking out (Extraction)

2Quantity of substance

If catalytic hydrodesulfurization is used to remove sulfur from diesel fuel, then sulfur content is reduced, but nitrogen interferes with the effectiveness of sulfur removal

Engineering Contradiction:
Improvesulfur contentVSAvoidsulfur removal effectiveness
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent applies preliminary removal of nitrogen-containing compounds from diesel fuel before hydrodesulfurization. By extracting nitrogen compounds first using ionic liquid, the subsequent sulfur removal process is not interfered with, ensuring effective and reliable hydrodesulfurization can proceed without the detrimental effects of nitrogen presence on catalyst performance.

Inventive Principle:
Principle #10Preliminary action

3Quantity of substance

If conventional ionic liquids are used for nitrogen removal, then nitrogen compounds can be extracted, but the ionic liquids are expensive and not readily available

Engineering Contradiction:
Improvenitrogen removalVSAvoidionic liquid availability
Core Design Contradiction:
Quantity of substanceVSEase of manufacture

Solution Approach 1:

The patent applies self-service by using caprolactamium ionic liquid, which is produced as a waste byproduct in the caprolactam manufacturing industry. This waste ionic liquid is repurposed for nitrogen removal from fuels, turning a disposal problem into a valuable resource. The approach eliminates the need to purchase expensive specialized ionic liquids while providing effective nitrogen extraction.

Inventive Principle:
Principle #25Self-service

4Productivity

If nitrogen content of VGO is high, then conversion degree and product yields are adversely affected, but reducing nitrogen requires additional processing steps

Engineering Contradiction:
Improveconversion degreeVSAvoidprocessing steps
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent applies extraction to remove nitrogen-containing compounds from VGO before conversion processes. The ionic liquid is contacted with VGO, nitrogen compounds are selectively extracted into the ionic liquid phase, and the treated VGO with reduced nitrogen content proceeds to hydrocracking or other conversion processes, improving conversion degree and product yields without requiring complex multi-step nitrogen removal sequences.

Inventive Principle:
Principle #2Taking out (Extraction)

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 reduces nitrogen content in VGO and diesel fuels, improving their convertibility and enabling the reuse of caprolactamium ionic liquids, enhancing the production of higher value hydrocarbon fractions and reducing sulfur levels in diesel fuels.

Implementation Method 1

contacting the vacuum gas oil with a VGO-immiscible caprolactamium ionic liquid to produce a vacuum gas oil and VGO-immiscible caprolactamium ionic liquid mixture, and separating the mixture to produce a vacuum gas oil effluent and a VGO-immiscible caprolactamium ionic liquid effluent comprising the nitrogen compound

Methodology Applied
Scientific EffectLiquid-liquid extraction: Liquid-Liquid Extraction

Data Source

PatentEP2831202B1Process for removing nitrogen from fuel streams with caprolactamium ionic liquids
Publication Date: 2017.08.02 ADVANSIX RESINS & CHEMICALS LLC
  • EP2831202B1 patent drawingFigure 1
  • EP2831202B1 patent drawingFigure 2A~2B
  • EP2831202B1 patent drawing

AI summary

A process for removing a nitrogen compound from a fuel feed, such as vacuum gas oil or diesel fuel, wherein the process includes contacting the fuel feed comprising the nitrogen compound with a fuel-immiscible caprolactamium ionic liquid to produce a fuel and fuel-immiscible caprolactamium ionic liquid mixture, and separating the mixture to produce a vacuum gas oil or a diesel effluent having a reduced nitrogen content relative to the vacuum gas oil or diesel feed. The invention provides an alternate use for caprolactamium ionic liquid that is produced in large quantities for the manufacture of caprolactam.