4-Amino-2-Halobenzonitrile Sulfonate Salt Separation by Solubility
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Solution Overview
Problem
Existing processes for producing 4-amino-2-halobenzonitrile compounds using halogen-containing solvents and gaseous hydrochloric acid are not industrially advantageous and lack efficiency in producing high-purity acid addition salts.
Innovation Solution
A process involving amination and salt formation steps using organic sulfonic acids to exploit the difference in solubility of isomeric acid addition salts in solvents, allowing for the efficient separation and production of high-purity organic sulfonic acid salts of 4-amino-2-halobenzonitrile compounds.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If halogen-containing solvents and gaseous hydrochloric acid are used in the production process, then the acid addition salt can be formed, but the process becomes difficult to handle and not industrially advantageous
Solution Approach 1:
The patent changes the physical state parameters of the reagents from gaseous (HCl gas) to liquid form (organic sulfonic acid solutions), making the process easier to handle and control industrially while maintaining the salt formation capability
Solution Approach 2:
The patent replaces expensive and difficult-to-handle gaseous HCl with readily available liquid organic sulfonic acids that can be easily dosed and controlled, reducing operational complexity and safety requirements
2Manufacturing precision
If conventional separation methods are used for isomeric mixtures, then separation can be achieved, but the production efficiency and purity are insufficient
Solution Approach 1:
The patent changes the chemical parameter by using organic sulfonic acids instead of conventional acids, which creates acid addition salts with significantly different solubility characteristics, enabling efficient separation through precipitation or extraction while achieving high purity and maintaining productivity
Solution Approach 2:
The patent replaces complex mechanical separation systems with a chemical approach where organic sulfonic acid salts of different isomers exhibit different solubilities, allowing separation through simple precipitation or extraction processes
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 enables the industrial production of high-purity organic sulfonic acid salts of 4-amino-2-halobenzonitrile compounds with improved efficiency and improved separation efficiency.
Implementation Method 1
use of an organic sulfonic acid as the acid allows industrially advantageous production of an organic sulfonic acid salt of a 4-amino-2-halobenzonitrile compound, the salt having a significantly different solubility in a solvent compared with other acid addition salts
Implementation Method 2
the separation using the difference in solubility between acid addition salts of isomers in the solvent includes precipitation and/or extraction
Data Source
AI summary
Provided is a process for industrially advantageously producing an acid addition salt of a 4-amino-2-halobenzonitrile compound with an organic sulfonic acid. An acid addition salt of a 4-amino-2-halobenzonitrile compound represented by the following formula (2) with an organic sulfonic acid is produced. The production process comprises a separation step of separating an acid addition salt of a compound represented by the formula (2) with an organic sulfonic acid, from an acid addition salt of an isomeric mixture of a compound, represented by the following formula (1) and at least containing the compound represented by the formula (2), with an organic sulfonic acid, using a difference in solubility between acid addition salts of isomers in a solvent: wherein X represents a halogen atom, R1 represents a reactively inactive substituent, and n denotes an integer of 0 to 3.