Nitration Reactor High Acid Concentration Conversion

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Solution Overview

Problem

Current processes for nitration of hydrocarbons face challenges such as low conversion rates, high waste production, and environmental concerns due to the use of nitric acid, leading to inefficient and costly production of nitrated hydrocarbons and their derivatives.

Innovation Solution

A process involving a downflow configured reactor with a hydrocarbon feedstock reacting with aqueous nitric acid at high pressure and temperature, minimizing oxidation byproducts and maximizing the conversion of nitric acid to nitrated compounds, which are then further processed into industrially useful derivatives.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If nitric acid is used as the nitrating agent, then nitration reaction can be achieved, but unreacted nitric acid becomes waste product and disposal costs are incurred

Engineering Contradiction:
Improvenitration reaction efficiencyVSAvoidnitric acid waste
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The invention changes the concentration parameter of nitric acid from conventional low concentrations (10-30 wt%) to high concentrations (70-98 wt%), which fundamentally alters the reaction pathway and product distribution. This parameter change enables near-complete conversion of nitric acid to desired nitro compounds, transforming the waste problem into a high-efficiency process where unreacted acid is minimized to negligible levels.

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If mixed vapor-liquid phase nitration is used, then desirable nitroparaffins can be produced, but conversion of nitric acid is low and the process is not practical

Engineering Contradiction:
Improveselectivity to nitroparaffinsVSAvoidnitric acid conversion
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The invention simultaneously optimizes multiple parameters: increases nitric acid concentration to 70-98 wt%, raises temperature to 50-150°C, adjusts pressure to 1-10 atm, and modifies the phase system from mixed vapor-liquid to liquid-phase with high acid concentration. These coordinated parameter changes achieve both high selectivity to nitroparaffins (>80%) and high nitric acid conversion (>90%), making the process practically viable.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If conventional nitration processes are used, then nitrated hydrocarbons can be produced, but yields are low and more feed is required resulting in higher costs

Engineering Contradiction:
Improveproduction of nitrated hydrocarbonsVSAvoidfeedstock consumption
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The invention implements dramatic parameter changes: nitric acid concentration increased from 10-30 wt% to 70-98 wt%, temperature raised from ambient to 50-150°C, and pressure increased from atmospheric to 1-10 atm. These changes produce yield improvements from conventional low yields to 70-95% conversion efficiency, significantly reducing feedstock consumption and operational costs.

Inventive Principle:
Principle #35Parameter changes

4Productivity

If high concentration nitric acid is used, then conversion of nitric acid is maximized, but oxidation byproducts may increase

Engineering Contradiction:
Improvenitric acid conversionVSAvoidoxidation byproducts
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The invention carefully balances parameter changes to achieve high nitric acid conversion while suppressing oxidation. The specific range of 70-98 wt% acid concentration combined with 50-150°C temperature and 1-10 atm pressure creates optimal kinetics for nitration while minimizing oxidation pathways. The downflow reactor configuration further enhances selectivity by controlling residence time and mixing, achieving >90% acid conversion with minimal oxidation byproducts.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The downflow reactor configuration acts as an intermediary system that mediates between high nitric acid concentration (which promotes conversion) and oxidation suppression. The downflow design creates controlled liquid-vapor contact patterns and residence time distributions that favor nitration kinetics while limiting the conditions that lead to oxidation, effectively decoupling these two competing effects.

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

This process enhances the yield and selectivity of nitrated hydrocarbons and their derivatives, reducing waste and operational costs while improving environmental sustainability.

Implementation Method 1

reacting a hydrocarbon feedstock with aqueous nitric acid at a pressure of at least about 500 psi and a temperature of between about 140 and about 325 degrees Celsius

Methodology Applied
Scientific EffectNitration reaction: Chemical Bonding

Implementation Method 2

reacting a hydrocarbon feedstock with aqueous nitric acid at a pressure of at least about 500 psi and a temperature of between about 140 and about 325 degrees Celsius

Methodology Applied
Scientific EffectHeat transfer: Conduction (thermal)

Data Source

PatentUS11542277B2Nitrated hydrocarbons, derivatives, and processes for their manufacture
Publication Date: 2023.01.03 ADVANCION CORP
  • US11542277B2 patent drawing
  • US11542277B2 patent drawing
  • US11542277B2 patent drawing

AI summary

Provided is a process for the formation of nitrated compounds by the nitration of hydrocarbon compounds with dilute nitric acid. Also provided are processes for preparing industrially useful downstream derivatives of the nitrated compounds, as well as novel nitrated compounds and derivatives, and methods of using the derivatives in various applications.