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N-(cyclohexylthio) phthalimide: Exploring its Role in Vulcanization and Inhibition

Chemical Properties and Safety

Chemical Properties and Safety


Understanding the Chemical Composition of N-(cyclohexylthio) phthalimide

N-(cyclohexylthio) phthalimide (NCTP) is a complex organic compound with a unique chemical structure that lends itself to its function in vulcanization and inhibition processes. Its chemical formula is C16H15NO2S, representing a composition of 16 carbon atoms (C), 15 hydrogen atoms (H), one nitrogen atom (N), two oxygen atoms (O), and one sulfur atom (S). This compound is characterized by the presence of a phthalimide group (C6H4(CO)2NR) and a cyclohexylthio group (C6H11S), which are responsible for its chemical properties and reactivity. It is essential to handle NCTP with care due to its potential hazards, including skin and eye irritation and harm to the aquatic environment.

Essential Safety Measures for Handling N-(cyclohexylthio) phthalimide

When dealing with N-(cyclohexylthio)phthalimide, it’s crucial to adhere to the following safety measures for effective handling:

  1. Personal Protective Equipment (PPE): Always wear suitable protective clothing, gloves, and eye/face protection when handling NCTP to prevent skin or eye contact.
  2. Ventilation: When handling the compound in a laboratory or industrial setting, ensure proper ventilation to avoid inhalation of dust or fumes.
  3. Avoidance of Combustible Materials: NCTP can react with combustible materials. Therefore, its storage and usage areas should be free from such materials.
  4. Storage: Store NCTP in a cool, dry place in tightly closed containers. Keep away from sources of ignition and incompatible materials.
  5. Waste Disposal: Dispose of contents and containers in accordance with local, regional, and national regulations.
  6. Handling Spills: In case of a spill, avoid dust formation, sweep up to prevent slipping hazard and dispose of residues as mentioned above.

Remember, safety should always come first when handling any chemical compound, including N-(cyclohexylthio)phthalimide.

Product Description and Specification of N-(cyclohexylthio) phthalimide

N-(cyclohexylthio)phthalimide (NCTP) is a white, crystalline organic compound with the molecular formula C14H15NO2S. It exhibits a molecular weight of 261.34 g/mol and a melting point range of 80-82°C. NCTP is soluble in common organic solvents like acetone, ethyl acetate, and toluene while being practically insoluble in water. It is widely used in industrial applications as a secondary accelerator and activator in polymer industries, particularly in the vulcanization process of rubber. The product is supplied in the form of powder, with a purity level of 99% as determined by High-Performance Liquid Chromatography (HPLC). It is packaged in polypropylene bags, each containing 25kg of the compound. Please note that the product should be stored in a cool, dry place under 30°C and away from direct sunlight to maintain its stability and performance.

Identifying N-(cyclohexylthio) phthalimide: CAS, Property, and Identifier Details

The identifier details for N-(cyclohexylthio)phthalimide are as follows:

  • CAS Number: The CAS (Chemical Abstracts Service) number for N-(cyclohexylthio)phthalimide is 17796-82-6. The CAS number is a unique identifier assigned to each chemical substance and is widely used in the scientific community.
  • EINECS Number: The European Inventory of Existing Commercial Chemical Substances (EINECS) number for N-(cyclohexylthio)phthalimide is 241-774-1. This number is used to identify substances on the European market.
  • Molecular Structure: The molecular structure of N-(cyclohexylthio)phthalimide consists of a cyclohexylthio group attached to a phthalimide unit.
  • InChI Key: The International Chemical Identifier (InChI) Key for N-(cyclohexylthio)phthalimide is FZNJVGJDPQVAIB-UHFFFAOYSA-N.
  • Chemical Properties: N-(cyclohexylthio)phthalimide is a white, crystalline organic compound. It has a molecular weight of 261.34 g/mol and a melting point range of 80-82°C. It’s soluble in common organic solvents but practically insoluble in water.
  • Chemical Safety: The compound is safe to handle but should be kept away from ignition sources and incompatible materials. It should be disposed of in accordance with local, regional, and national regulations.

Remember, always refer to the Material Safety Data Sheet (MSDS) for a comprehensive understanding of the chemical’s properties and handling procedures.

Application and Use in Vulcanization

Application and Use in Vulcanization


Exploring the Role of N-(cyclohexylthio) phthalimide in Vulcanization

N-(cyclohexylthio)phthalimide plays a significant role in the vulcanization process, a process that is critical in the rubber industry:

  1. Vulcanization Accelerator: As a vulcanization accelerator, N-(cyclohexylthio)phthalimide enhances the rate at which rubber undergoes the vulcanization process. This consequently reduces the time it takes to produce rubber products.
  2. Improved Physical Properties: The incorporation of N-(cyclohexylthio)phthalimide in the vulcanization process helps in improving the physical properties of vulcanized rubber, such as its elasticity and strength.
  3. Heat Resistance: Rubber products vulcanized using N-(cyclohexylthio)phthalimide exhibit great resistance to heat, which extends the lifespan and functionality of the products.
  4. Enhanced Chemical Stability: The presence of N-(cyclohexylthio)phthalimide in vulcanized rubber enhances its stability against chemical reactions that could degrade the rubber.
  5. Suitability for Various Rubber Types: N-(cyclohexylthio)phthalimide is compatible with many different types of rubber, making it a versatile ingredient in the vulcanization process.

In conclusion, N-(cyclohexylthio)phthalimide is an essential component in the vulcanization process due to its ability to accelerate the process, improve the physical properties of the rubber, increase its heat resistance, enhance its chemical stability, and its versatility with a variety of rubber types.

Impact of N-(cyclohexylthio) phthalimide on Rubber Production and Inhibition

The implications of N-(cyclohexylthio)phthalimide on rubber production and inhibition are manifold. Here are some key points:

  1. Production Efficiency: The use of N-(cyclohexylthio)phthalimide as a vulcanization accelerator reduces the time it takes to produce rubber products, thereby increasing production efficiency.
  2. Product Quality: By improving the physical properties and heat resistance of vulcanized rubber, N-(cyclohexylthio)phthalimide contributes to the production of high-quality rubber products.
  3. Production Cost: The increased efficiency and improved quality of rubber products could potentially contribute to a reduction in production costs, thereby providing a competitive edge in the market.
  4. Versatility: The compatibility of N-(cyclohexylthio)phthalimide with different types of rubber expands the range of rubber products that can be produced, offering greater flexibility in production.
  5. Scorch Safety: N-(cyclohexylthio)phthalimide provides excellent scorch safety, preventing premature vulcanization during the processing of rubber.
  6. Environmental Impact: The chemical stability provided by N-(cyclohexylthio)phthalimide could lead to a decrease in the degradation of rubber products, potentially reducing the environmental impact.

Optimizing Vulcanization Process with N-(cyclohexylthio) phthalimide

To optimize the vulcanization process with N-(cyclohexylthio)phthalimide, a systematic approach is essential.

First, the precise measurement of the accelerator is crucial to ensure efficiency and quality. Overuse can lead to over-vulcanization, compromising the rubber’s properties, while underuse can result in insufficient vulcanization, affecting the product’s durability. Therefore, maintaining optimal concentration is key.

Secondly, maintaining appropriate processing temperatures is equally important, as it impacts the vulcanization rate directly. Additionally, mixing order matters. The introduction of N-(cyclohexylthio)phthalimide at the right stage can prevent premature vulcanization, ensuring scorch safety.

Lastly, the use of additional stabilizing agents alongside N-(cyclohexylthio)phthalimide can enhance the durability and lifespan of the vulcanized rubber products. By following these steps, manufacturers can leverage the benefits of N-(cyclohexylthio)phthalimide to optimize the vulcanization process.

Inhibitor Properties of N-(cyclohexylthio) phthalimide in Sulfur Vulcanization

In the context of sulfur vulcanization, N-(cyclohexylthio)phthalimide (CTP) acts as a superior inhibitor, preventing premature vulcanization, or ‘scorching’, without hindering the actual vulcanization process. The distinctive structure of CTP enables it to form stable complexes with sulfur, delaying the onset of vulcanization and providing excellent scorch safety. This postponement allows the rubber compound ample time to flow and fill the mold properly before cross-linking begins. Furthermore, CTP does not significantly affect the state of sulfur cross-linking, ensuring that the physical properties of the vulcanized rubber remain desirable. Therefore, the inhibitor properties of CTP contribute significantly to achieving optimal processing safety while maintaining the quality of the vulcanized rubber products.

Comparative Analysis of N-(cyclohexylthio) phthalimide with Other Rubber Additives

Within the rubber manufacturing industry, several additives and inhibitors are used, among which N-(cyclohexylthio)phthalimide (CTP) stands out due to its superior properties. Let’s compare CTP with some commonly used alternatives:

  • Sulfenamides: Although sulfenamides, like N-cyclohexylbenzothiazole-2-sulfenamide (CBS), offer good scorch safety and a fast cure rate, they can lead to poor heat aging, especially in the absence of adequate antioxidant protection. CTP, on the other hand, does not significantly compromise heat aging.
  • Thiurams: Thiurams, such as Tetramethylthiuram disulfide (TMTD), provide a very fast cure rate but have a high tendency to cause premature vulcanization or ‘scorching.’ Unlike thiurams, CTP has robust scorch safety and prevents premature vulcanization effectively.
  • Dithiocarbamates: While Dithiocarbamates, such as Zinc dimethyldithiocarbamate (ZDMC), offer a fast cure rate, they have relatively lower scorch safety. In contrast, CTP ensures excellent scorch safety while maintaining an optimal cure rate.

In summary, while other additives have their benefits, N-(cyclohexylthio)phthalimide’s unique structure and properties offer a balance between scorch safety and cure rate, making it a superior choice for sulfur vulcanization.

Production and Handling Best Practices

Production and Handling Best Practices


Recommended Production Methods for N-(cyclohexylthio) phthalimide

The production of N-(cyclohexylthio)phthalimide (CTP) follows a specific process to ensure its high quality and efficacy as a rubber additive. This method involves:

  1. Synthesis: The first step in producing CTP is the reaction of phthalimide with cyclohexylamine in the presence of a strong acid, such as hydrochloric acid. This step forms N-cyclohexylphthalimide.
  2. Sulfurization: Once N-cyclohexylphthalimide is formed, it is sulfurized using elemental sulfur to form CTP. The sulfurization process must be strictly controlled to prevent the formation of unwanted byproducts.
  3. Purification: The final step involves the purification of CTP to remove any unreacted materials and byproducts. This is usually achieved by recrystallization from a suitable solvent.

It is critical to note that safety measures must be adhered to strictly during the production of CTP, given the hazardous nature of some of the reactants and byproducts. Proper ventilation, use of personal protective equipment (PPE), and adherence to waste disposal protocols are vital to ensure a safe and successful production process.

Storage Conditions and Handling Instructions for N-(cyclohexylthio) phthalimide

N-(cyclohexylthio)phthalimide (CTP) must be stored under specific conditions to ensure its stability and effectiveness. The following guidelines should be adhered to:

  • Storage Temperature: CTP should be stored in a cool, well-ventilated area. The recommended storage temperature is below 30°C (86°F).
  • Humidity: CTP is hygroscopic, which means it absorbs moisture from the air. Therefore, it should be stored in a dry location to prevent moisture absorption, which could compromise its effectiveness.
  • Light Exposure: Direct sunlight or UV radiation can degrade CTP, so it should be stored in a dark or light-protected area.
  • Container: The container for CTP should be tightly closed when not in use to prevent contamination. It is recommended to use original, unopened containers for storage.
  • Shelf Life: When stored as recommended, CTP has a shelf life of up to 2 years.

For handling CTP, the following precautions should be observed:

  • Handling: Handle with care to avoid skin and eye contact. Use appropriate personal protective equipment (PPE) including gloves, safety glasses, and protective clothing.
  • Spillage: In case of spillage, sweep up carefully and place in a suitable container for disposal. Avoid dust formation.
  • Fire: In case of fire, use water, carbon dioxide, dry chemical, or foam extinguishers. Do not use direct water jets on burning material.
  • First-Aid Measures: In case of contact, rinse skin or eyes thoroughly with water. If swallowed, do not induce vomiting. Seek medical attention if necessary.

Hazard Identification and Safety Measures in N-(cyclohexylthio) phthalimide Use

  • Hazard Classification: N-(cyclohexylthio) phthalimide is classified as a skin irritant, serious eye irritant, and may cause respiratory irritation. It should be handled with care to prevent exposure.
  • Personal Protective Equipment: Always wear suitable protective clothing, including gloves and eye/face protection when handling N-(cyclohexylthio) phthalimide.
  • Respiratory Protection: If exposure limits are exceeded or irritation is experienced, use approved respiratory protection equipment.
  • Engineering Controls: Ensure there is adequate ventilation, especially in confined areas. Install an emergency eye wash station and a safety shower.
  • Handling Procedures: Avoid contact with skin, eyes, and clothing. Prevent dust formation. Do not breathe dust.
  • Storage: Store in accordance with local regulations. Store in a segregated and approved area. Keep the container tightly closed in a dry, cool, and well-ventilated place.
  • Disposal Considerations: Dispose of contents/containers to an approved waste disposal plant in accordance with local/regional/national/international regulations.
  • Spill Cleanup Measures: In case of spillage, wear protective equipment and carefully sweep up the spill. Avoid creating dust and immediately clean up spills to prevent slip hazards. Place in a suitable container for disposal.
  • First-aid Measures: In case of skin contact, rinse with plenty of water. If eye contact occurs, rinse immediately with plenty of water and seek medical advice. If inhaled, move to fresh air and keep at rest. If swallowed, do not induce vomiting and seek medical attention immediately.

Documentation and Compliance Requirements for N-(cyclohexylthio) phthalimide

Documentation and compliance for N-(cyclohexylthio) phthalimide involve a meticulous procedure tailored according to local, regional, national, and international regulations. A comprehensive Material Safety Data Sheet (MSDS) must be prepared and updated periodically, detailing the substance’s physical and chemical properties, potential hazards, handling and storage procedures, and first-aid measures. Additionally, all workers handling the substance should undergo periodic training to ensure optimal safety procedures are adhered to.

Furthermore, it is also mandatory to maintain accurate records of the quantity of N-(cyclohexylthio) phthalimide in storage, its utilization in various processes, and waste generation. These reports need to be submitted to relevant environmental and health authorities as required. In cases of spills, accidents, or exposure incidents related to N-(cyclohexylthio) phthalimide, detailed incident reports must be prepared and submitted to designated authorities promptly.

Compliance with these requirements not only ensures safety and mitigates risks but also plays a key role in fostering a responsible and sustainable operational environment.

Addressing Safety and Environmental Concerns in N-(cyclohexylthio) phthalimide Production

Safety and environmental concerns sit at the forefront of N-(cyclohexylthio) phthalimide production. Addressing these concerns requires a multi-faceted approach:

  1. Efficient Use of Resources: Optimize the use of raw materials and energy in the production process to reduce waste and conserve resources.
  2. Safe Handling and Storage: Implement stringent protocols for safe handling and storage of N-(cyclohexylthio) phthalimide, minimizing the risk of exposure or accidents.
  3. Waste Management: Develop an effective waste management system, ensuring that waste is handled, stored, and disposed of in compliance with environmental regulations.
  4. Emission Control: Install state-of-the-art emission control systems to limit the release of harmful gases into the environment.
  5. Emergency Preparedness: Establish a robust emergency response plan, including training personnel to respond promptly and effectively to any accidents or spills.
  6. Continual Monitoring and Evaluation: Regularly monitor and evaluate safety and environmental measures to identify areas for improvement and compliance with regulatory standards.

By focusing on these areas, producers can ensure that their operations are not only safe, but also environmentally responsible.

Research and Development in Rubber Industry

Research and Development in Rubber Industry


Studying the Chemical Reaction of N-(cyclohexylthio) phthalimide in Vulcanization

The chemical reaction of N-(cyclohexylthio) phthalimide (NCPh) during vulcanization is essential in the rubber industry. NCPh acts as an accelerator, catalyzing the cross-linking of polymer chains to enhance the strength and elasticity of rubber. Understanding this reaction optimizes vulcanization, leading to high-quality rubber products and advancements in safety and environmental practices.

Role of N-(cyclohexylthio) phthalimide in Improving Rubber Adhesive and Quality

N-(cyclohexylthio) phthalimide (NCPh) plays a significant role in enhancing the adhesive quality and overall performance of rubber. As an accelerator in vulcanization, NCPh facilitates the cross-linking of polymer chains, resulting in increased tensile strength, resilience, and durability of the rubber. Moreover, NCPh aids in improving the rubber’s adhesiveness, a critical property in applications such as tire manufacturing and industrial adhesives. The superior adhesive quality ensures a firm grip and bonding, thereby enhancing the product’s longevity and performance. In essence, the incorporation of NCPh in the vulcanization process not only optimizes the production of rubber but also significantly upgrades its quality and adhesive properties.

Exploring Alternative Uses and Applications of N-(cyclohexylthio) phthalimide

Aside from its critical function in the vulcanization process, N-(cyclohexylthio) phthalimide (NCPh) has potential for use in fields beyond the rubber industry due to its unique chemical properties. For instance, in the realm of organic chemistry, NCPh could serve as a reagent for the introduction of the cyclohexylthio group into various organic compounds, potentially expanding synthetic routes and methodologies. Moreover, NCPh’s sulfuric components suggest potential applications in the production of flame-retardant materials. These alternative uses of NCPh underscore the significance of ongoing research into its full potential, opening avenues for innovation and development in diverse industrial sectors.

Impact of N-(cyclohexylthio) phthalimide on Natural Rubber and Synthetic Variants

The effect of N-(cyclohexylthio) phthalimide (NCPh) varies considerably between natural rubber and different synthetic variants, reflecting the unique structural and compositional characteristics of each material:

  1. Natural Rubber: The application of NCPh in the vulcanization of natural rubber significantly enhances its mechanical properties. The increase in tensile strength, resilience, and durability is particularly marked, offering improved performance in applications such as tire manufacturing and engineering components.
  2. Styrene-Butadiene Rubber (SBR): In SBR, a common synthetic rubber, NCPh acts as an excellent accelerator in the vulcanization process. SBR treated with NCPh exhibits excellent heat and abrasion resistance, making it suitable for high-stress applications.
  3. Nitrile Rubber (NBR): NBR is known for its exceptional oil and fuel resistance. The addition of NCPh in the vulcanization process further enhances these properties, leading to a robust material used in automotive and industrial applications.
  4. Neoprene (CR): CR benefits significantly from the addition of NCPh in its production. The resulting rubber exhibits a high degree of flame retardance and chemical resistance, making it ideal for applications in harsh environments.

In conclusion, the incorporation of NCPh positively impacts the properties and application scope of both natural rubber and various synthetic variants, thereby enhancing their performance in their respective fields of use.

Future Prospects and Development Trends in N-(cyclohexylthio) phthalimide Research

The field of NCPh research holds immense potential, with ongoing exploration of its various applications and sustainable production methods. Exciting developments include expanding its use in different rubber types and investigating its health and environmental impacts. However, it is crucial to ensure that these advancements are sustainable and considerate of broader environmental and societal concerns.


  1. Kinetics and Mechanism of the Reaction of 2-Mercaptobenzothiazole with N-(Cyclohexylthio) Phthalimide and Related Compounds: This academic journal article provides an in-depth study about the reaction kinetics of N-(cyclohexylthio)phthalimide with other compounds.
  2. The Action of N-(Cyclohexylthio)Phthalimide as a Prevulcanization Inhibitor of 2-Bisbenzothiazole-2,2′-Disulfide Accelerated Sulfur Vulcanization: This source discusses the role of N-(cyclohexylthio)phthalimide as a prevulcanization inhibitor in sulfur vulcanization.
  3. KINETICS AND MECHANISM OF THE REACTION OF 2-MERCAPTOBENZOTHIAZOLE WITH N-(CYCLOHEXYLTHIO) PHTHALIMIDE AND RELATED COMPOUNDS: This Korean scientific article provides another perspective on the reaction mechanisms of N-(cyclohexylthio)phthalimide.
  4. Pre-vulcanization inhibition of a Nt-butyl-2-benzothiazole sulfenamide cure by N-(cyclohexylthio) phthalimide: This research article focuses on the role of N-(cyclohexylthio)phthalimide in the inhibition of vulcanization.
  5. Contact sensitization to N-(cyclohexylthio) phthalimide: This medical study discusses the potential sensitization rates due to exposure to N-(cyclohexylthio)phthalimide.
  6. Promoted electrolytic cross-coupling reaction of imides with disulfides: This paper from the American Chemical Society presents a synthesis method for N-(cyclohexylthio)phthalimide.
  7. Contact Allergenicity of N-(Cyclohexylthio)phthalimide: This Japanese study explores the allergenicity of N-(cyclohexylthio)phthalimide.
  8. N-(Morpholinothio)Imides as Curing Agents in Semiefficient Vulcanization Systems: This article discusses the use of N-(cyclohexylthio)phthalimide and similar compounds as curing agents in vulcanization systems.
  9. N‐(morpholinothio)imides as curing agents in semi efficient vulcanization systems: Another source discussing the use of N-(cyclohexylthio)phthalimide as a curing agent in vulcanization systems.
  10. Allergic patch test reactions caused by the rubber chemical cyclohexyl thiophthalimide: This source provides insights into allergic reactions that can be caused by N-(cyclohexylthio)phthalimide, further emphasizing the need for safety measures when handling this compound.Recommended Reading: The Ultimate Guide to High-Quality ZDEC Rubber Accelerator 
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