5-Ethylidene-2-Norbornene Process Recycling Solvent

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

The existing preparation process of 5-ethylidene-2-norbomene faces inefficiencies in separation and purification, leading to raw material loss and increased economic costs.

Innovation Solution

A multi-step process involving the thermal decomposition of dicyclopentadiene, purification of cyclopentadiene, Diels-Alder reaction with 1,3-butadiene, recovery of solvents and unreacted materials, and subsequent isomerization of 5-vinyl-2-norbornene to produce 5-ethylidene-2-norbornene, with optimized recycling and separation techniques to enhance process efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of substance

If conventional separation and purification methods are used in the 5-ethylidene-2-norbornene preparation process, then the process can be completed, but separation and purification efficiency is low leading to raw material loss

Engineering Contradiction:
Improveraw material lossVSAvoidseparation and purification efficiency
Core Design Contradiction:
Loss of substanceVSProductivity

Solution Approach 1:

The patent implements a recycling system where unreacted 1,3-butadiene and solvent are recovered from the reaction mixture through distillation and returned to the Diels-Alder reactor. This prevents raw material loss by recovering and reusing valuable components that would otherwise be discarded, directly addressing the contradiction between reducing substance loss and maintaining productivity.

Inventive Principle:
Principle #34Discarding and recovering

Solution Approach 2:

The process incorporates a feedback mechanism where the separation and purification units continuously monitor and return unreacted materials to the reaction stage. This closed-loop system ensures that raw materials are not lost but fed back into the process, improving both substance retention and overall process efficiency.

Inventive Principle:
Principle #23Feedback

2Ease of manufacture

If conventional preparation process is used, then 5-ethylidene-2-norbornene can be produced, but economic feasibility is reduced due to increased costs and utility usage

Engineering Contradiction:
Improveeconomic feasibilityVSAvoidutility usage
Core Design Contradiction:
Ease of manufactureVSLoss of energy

Solution Approach 1:

The patent combines multiple functions into integrated units: the separation tower simultaneously performs distillation and purification, while the recycling system merges solvent recovery with unreacted material return. This consolidation reduces the number of separate operations and utility requirements, improving economic feasibility while reducing energy loss.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

By recovering and recycling solvent and unreacted 1,3-butadiene instead of discarding them, the process reduces material waste and the need for continuous fresh material input. This decreases both operational costs and utility consumption, directly improving economic feasibility while reducing energy loss.

Inventive Principle:
Principle #34Discarding and recovering

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 proposed process achieves improved separation and purification efficiencies, reduces raw material loss, and enhances the economic feasibility of the 5-ethylidene-2-norbornene production by minimizing utility usage and process troubles.

Implementation Method 1

step a-1 of introducing dicyclopentadiene (DCPD) into a DCPD decomposition reactor (110) to thermally decompose the DCPD

Methodology Applied
Scientific EffectThermal decomposition: Pyrolysis

Implementation Method 2

step b-1 of introducing 1,3-butadiene (BD), a solvent, and cyclopentadiene separated from the top of the CPD purification tower (120) into a Diels-Alder reactor (210) to react the same

Methodology Applied
Scientific EffectDiels-Alder reaction: Chemical Bonding

Implementation Method 3

step d of introducing the 5-vinyl-2-norbornene into an isomerization reactor (410) to react the same

Methodology Applied
Scientific EffectIsomerization: Chemical Bonding

Implementation Method 4

step a-2 of introducing a product of step a-1 into a cyclopentadiene (CPD) purification tower (120)

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS12297159B2Preparation process of 5-ethylidene-2-norbornene
Publication Date: 2025.05.13 KOREA KUMHO PETROCHEMICAL CO LTD
  • US12297159B2 patent drawing
  • US12297159B2 patent drawing
  • US12297159B2 patent drawing

AI summary

A preparation process of 5-ethylidene-2-norbornene, including: introducing dicyclopentadiene into a dicyclopentadiene decomposition reactor to thermally decompose the dicyclopentadiene; introducing a product of the above step into a cyclopentadiene purification tower; introducing 1,3-butadiene, a solvent, and cyclopentadiene separated from the top of the cyclopentadiene purification tower into a Diels-Alder reactor to react the same; introducing a product of the immediate above step into a 1,3-butadiene removal tower to recover 1,3-butadiene from the top; introducing a mixture at the bottom of the 1,3-butadiene removal tower into a desolvation tower, and recycling a solvent and unreacted raw materials recovered from the top of the desolvation tower to the dicyclopentadiene decomposition reactor; introducing a mixture at the bottom of the desolvation tower into a 5-vinyl-2-norbornene separation tower to separate 5-vinyl-2-norbornene; and introducing the 5-vinyl-2-norbornene into an isomerization reactor to react the same.