Phenyl Mercaptocarbamate Purification via Crystallization
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Solution Overview
Problem
Existing methods for producing mercaptophenol compounds on an industrial scale face challenges due to the use of chlorosulfonylation reactions, which require strongly acidic reagents, leading to corrosion and odor control issues, and lack efficient purification methods for sulfur-containing intermediates.
Innovation Solution
A method involving the reaction of a phenyl carbamate compound with sulfur monochloride to introduce a sulfur atom selectively, producing a phenyl mercaptocarbamate compound as an intermediate, which allows for high-quality mercaptophenol production without chlorosulfonylation and provides high crystallinity for easier purification.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If chlorosulfonylation reaction is used to introduce sulfur atom, then sulfur atom introduction is achieved, but strongly acidic reagents cause corrosion and odor control issues
Solution Approach 1:
The patent extracts and removes the harmful strongly acidic reagents (fuming sulfuric acid, thionyl chloride, chlorosulfonic acid) from the chlorosulfonylation reaction process, replacing them with milder reagents that achieve the same sulfur atom introduction without causing corrosion or offensive odors
Solution Approach 2:
The patent converts the harmful acidic conditions into beneficial milder reaction conditions by using alternative reagents that maintain the effectiveness of sulfur atom introduction while eliminating the harmful effects of strong acidity, thereby transforming a harmful process into a safe and environmentally friendly one
2Manufacturing precision
If distillation is used to purify sulfur-containing intermediate, then purification is achieved, but special equipment and complicated operation are required to prevent odor diffusion
Solution Approach 1:
The patent extracts the problematic sulfur-containing intermediate from the liquid state and transforms it into a solid crystalline form, which eliminates the need for distillation and its associated complex odor-control equipment and operations
Solution Approach 2:
The patent utilizes phase transition by promoting crystallization of the sulfur-containing intermediate from liquid to solid state, which simplifies the purification process from distillation to filtration or recrystallization, thereby reducing equipment complexity and operational difficulty while maintaining high purification quality
3Manufacturing precision
If intermediate compound is liquid, then only distillation is available for purification, but this requires special equipment and complicated operation
Solution Approach 1:
The patent induces phase transition of the intermediate compound from liquid to solid crystalline form, which fundamentally changes the available purification methods from distillation (complex) to filtration or recrystallization (simple), thereby dramatically improving ease of operation while maintaining high purification capability
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 eliminates the need for acidic reagents, reduces odor issues, and enables effective purification through filtration or recrystallization, improving the production efficiency and quality of mercaptophenol compounds on an industrial scale.
Implementation Method 1
a sulfur atom is position-selectively introduced by a reaction with sulfur monochloride
Implementation Method 2
followed by a hydrolysis reaction to produce the target mercaptophenol compound
Data Source
AI summary
A production method in which a mercaptophenol compound is obtained using an industrially preferred sulfur atom introduction reaction, and intermediate compounds of the mercaptophenol compound are provided. A method for producing a mercaptophenol compound in which a phenyl carbamate compound is produced using a phenol compound as a raw material, and then a sulfur atom is regioselectively introduced by a reaction with sulfur monochloride, and a phenyl mercaptocarbamate compound is produced as an intermediate.