N,N-Dimethylcyclohexylamine (DMCHA), a tertiary amine, is a colorless to pale yellow liquid with a characteristic amine odor. It is a versatile chemical compound finding applications in various fields, including catalysis, polymer chemistry, and pharmaceutical research. This article provides a comprehensive overview of DMCHA, encompassing its physical and chemical properties, synthesis methods, applications, safety considerations, and supplier pricing information.

Contents

1. Introduction
2. Nomenclature and Identifiers
3. Physical and Chemical Properties
   • 3.1 Physical Properties
   • 3.2 Chemical Properties
4. Synthesis Methods
   • 4.1 Reductive Amination of Cyclohexanone
   • 4.2 Alkylation of Cyclohexylamine
5. Applications
   • 5.1 Catalysis
   • 5.2 Polymer Chemistry
   • 5.3 Pharmaceutical Applications
   • 5.4 Other Applications
6. Safety Considerations
   • 6.1 Toxicity
   • 6.2 Handling and Storage
7. Supplier Pricing Information
   • 7.1 Factors Affecting Pricing
   • 7.2 Regional Price Variations
   • 7.3 Price Trends
8. Quality Control and Analysis
   • 8.1 Purity Determination
   • 8.2 Impurity Profile
9. Regulatory Information
10. Future Trends
11. Conclusion
12. References

1. Introduction

N,N-Dimethylcyclohexylamine (DMCHA) is an organic compound belonging to the class of tertiary amines. Its molecular structure consists of a cyclohexane ring with two methyl groups attached to the nitrogen atom. DMCHA is a valuable chemical intermediate and a functional reagent in diverse industrial processes. Its unique properties, stemming from the combination of a cyclic aliphatic structure and a tertiary amine functionality, make it suitable for a wide array of applications.

2. Nomenclature and Identifiers

Property	Value
IUPAC Name	N,N-Dimethylcyclohexanamine
Common Name	N,N-Dimethylcyclohexylamine (DMCHA)
CAS Registry Number	98-94-2
Molecular Formula	C8H17N
Molecular Weight	127.23 g/mol
SMILES Notation	CN(C)C1CCCCC1
PubChem CID	7410

3. Physical and Chemical Properties

3.1 Physical Properties

Property	Value	Reference
Appearance	Colorless to pale yellow liquid
Odor	Amine-like
Density	0.845 g/mL at 20°C	Sigma-Aldrich SDS
Boiling Point	160-162°C	Sigma-Aldrich SDS
Melting Point	-60°C
Flash Point	41°C	Sigma-Aldrich SDS
Refractive Index	1.447 at 20°C	Sigma-Aldrich SDS
Solubility in Water	Slightly soluble
Solubility in Organic Solvents	Soluble in most common organic solvents
Vapor Pressure	2.7 mmHg at 25°C

3.2 Chemical Properties

DMCHA exhibits typical chemical properties of tertiary amines. It is a weak base and can readily react with acids to form salts. The lone pair of electrons on the nitrogen atom makes it a nucleophile, participating in reactions such as alkylations and acylation. The cyclohexane ring provides stability and influences the steric environment around the nitrogen atom.

• Basicity: DMCHA can neutralize acids, forming salts. This property is utilized in various chemical processes, including acid scavenging and pH adjustment.
• Nucleophilicity: The nitrogen atom’s lone pair allows DMCHA to act as a nucleophile, reacting with electrophilic centers in organic molecules. This is crucial in catalytic applications.
• Reactions with Isocyanates: DMCHA is a commonly used catalyst for reactions involving isocyanates, particularly in the production of polyurethane foams and elastomers. It accelerates the formation of urethane linkages.
• Quaternization: DMCHA can undergo quaternization reactions with alkyl halides to form quaternary ammonium salts. These salts find applications as phase-transfer catalysts and surfactants.

4. Synthesis Methods

Several synthetic routes are available for the production of DMCHA, with the following being the most common:

4.1 Reductive Amination of Cyclohexanone

This method involves the reductive amination of cyclohexanone with dimethylamine in the presence of a reducing agent, typically hydrogen and a metal catalyst (e.g., nickel or palladium).

Cyclohexanone + Dimethylamine + H2  --[Catalyst]--> DMCHA + H2O

This is a widely used industrial method due to the readily available starting materials and relatively high yields. The reaction conditions need to be carefully controlled to minimize the formation of byproducts such as cyclohexylamine and N-methylcyclohexylamine.

4.2 Alkylation of Cyclohexylamine

This method involves the alkylation of cyclohexylamine with methylating agents, such as methyl iodide or dimethyl sulfate.

Cyclohexylamine + 2 CH3X  --> DMCHA + 2 HX  (where X = I or OSO3CH3)

This method can be conducted in either one or two steps. A two-step procedure involves first forming N-methylcyclohexylamine and then methylating it further to obtain DMCHA. While this route can offer better control over the reaction, it generally involves more steps and potentially lower overall yield compared to reductive amination.

Table: Comparison of Synthesis Methods

Feature	Reductive Amination of Cyclohexanone	Alkylation of Cyclohexylamine
Starting Materials	Cyclohexanone, Dimethylamine	Cyclohexylamine, Methylating Agent
Yield	Generally high	Variable, can be lower
Reaction Conditions	Moderate temperature and pressure	Can be conducted at lower temperatures
Byproducts	Cyclohexylamine, N-methylcyclohexylamine	Salts of the methylating agent
Scale of Production	Industrial scale	Suitable for lab and small-scale production

5. Applications

DMCHA finds diverse applications in various industries due to its unique properties as a tertiary amine.

5.1 Catalysis

DMCHA is a commonly employed catalyst in various chemical reactions, particularly in the polyurethane industry.

• Polyurethane Production: DMCHA acts as a catalyst in the reaction between isocyanates and polyols to form polyurethanes. It accelerates both the urethane (polyol-isocyanate) and urea (isocyanate-water) reactions. Its catalytic activity is crucial in controlling the foaming process and the final properties of polyurethane foams, elastomers, and coatings. The concentration of DMCHA used affects the rate of reaction and the resulting polymer structure. Different DMCHA derivatives and formulations are often used to tailor the catalytic activity to specific polyurethane systems.
• Other Catalytic Applications: DMCHA can also catalyze other organic reactions, such as transesterification and polymerization reactions.

5.2 Polymer Chemistry

Beyond its role as a catalyst, DMCHA is used in other aspects of polymer chemistry.

• Chain Extender/Crosslinker: In some specific polymer systems, DMCHA can be used as a chain extender or crosslinker, modifying the polymer’s molecular weight and network structure.
• Stabilizer: DMCHA can act as a stabilizer in certain polymer formulations, preventing degradation and improving the long-term performance of the material.

5.3 Pharmaceutical Applications

DMCHA is used as a building block in the synthesis of various pharmaceutical compounds.

• Intermediate in Drug Synthesis: The cyclohexylamine moiety is present in several pharmaceutical drugs, and DMCHA serves as a useful intermediate for introducing this structural element into drug molecules.
• pH Modifier: DMCHA can be used to adjust the pH of pharmaceutical formulations, ensuring optimal stability and bioavailability of the active ingredients.

5.4 Other Applications

• Corrosion Inhibitor: DMCHA can be used as a corrosion inhibitor in various industrial applications, protecting metal surfaces from degradation.
• Solvent: DMCHA can serve as a solvent in certain chemical reactions and processes.
• Additive: DMCHA is sometimes added to various formulations to improve their performance or properties.

Table: Applications of DMCHA by Industry

Industry	Application	Benefits
Polyurethane	Catalyst for polyurethane foam, elastomer, and coating production	Controls reaction rate, affects foam density, improves polymer properties
Pharmaceutical	Intermediate in drug synthesis, pH modifier	Introduces cyclohexylamine moiety, ensures formulation stability and bioavailability
Chemical Synthesis	Catalyst, solvent, reagent	Facilitates various organic reactions, provides a suitable reaction medium, participates in reactions
Metalworking	Corrosion inhibitor	Protects metal surfaces from corrosion

6. Safety Considerations

6.1 Toxicity

DMCHA is a hazardous chemical and requires careful handling.

• Irritant: DMCHA is an irritant to the skin, eyes, and respiratory tract. Contact can cause redness, pain, and burns. Inhalation can cause coughing, shortness of breath, and irritation of the mucous membranes.
• Harmful if Swallowed: Ingestion of DMCHA can cause gastrointestinal irritation, nausea, vomiting, and abdominal pain.
• Flammable: DMCHA is a flammable liquid and vapor. It can form explosive mixtures with air.
• Environmental Hazards: DMCHA can be harmful to aquatic organisms.

Table: Safety Data for DMCHA

Hazard	Description
Acute Toxicity (Oral)	Harmful if swallowed (LD50: approximately 250-500 mg/kg in rats)
Acute Toxicity (Dermal)	May be harmful in contact with skin (LD50: data varies, generally >2000 mg/kg in rabbits)
Acute Toxicity (Inhalation)	Harmful if inhaled (LC50: data varies, depends on exposure time)
Skin Corrosion/Irritation	Causes skin irritation
Serious Eye Damage/Eye Irritation	Causes serious eye irritation
Specific Target Organ Toxicity – Single Exposure	May cause respiratory irritation
Flammability	Flammable liquid and vapor

6.2 Handling and Storage

• Personal Protective Equipment (PPE): Wear appropriate PPE, including gloves, safety glasses, and a respirator, when handling DMCHA.
• Ventilation: Use in a well-ventilated area or under a fume hood.
• Storage: Store in a tightly closed container in a cool, dry, and well-ventilated area, away from incompatible materials (e.g., strong acids, oxidizing agents). Protect from heat, sparks, and open flames.
• Spills: Contain and absorb spills with an inert material (e.g., sand, vermiculite) and dispose of properly.
• Firefighting: Use appropriate extinguishing media (e.g., foam, carbon dioxide, dry chemical) for flammable liquids.

7. Supplier Pricing Information

Obtaining accurate and up-to-the-minute pricing information for DMCHA requires direct contact with chemical suppliers. However, general factors influencing the pricing and typical price ranges can be discussed.

7.1 Factors Affecting Pricing

Several factors influence the price of DMCHA, including:

• Purity: Higher purity DMCHA commands a higher price due to the more rigorous purification processes involved.
• Quantity: Prices typically decrease with larger quantities purchased due to economies of scale.
• Supplier: Different suppliers may have different pricing structures based on their production costs, overhead, and profit margins.
• Market Demand: Increased demand for DMCHA can drive prices up, while decreased demand can lead to price reductions.
• Raw Material Costs: Fluctuations in the prices of raw materials, such as cyclohexanone and dimethylamine, can impact the price of DMCHA.
• Transportation Costs: Shipping costs, particularly for hazardous materials, can significantly affect the overall price.
• Geopolitical Factors: Global events, such as trade wars and political instability, can impact the supply chain and prices of chemical products.

7.2 Regional Price Variations

DMCHA prices can vary significantly across different regions due to factors such as transportation costs, import duties, local regulations, and competitive landscapes. Generally, prices in regions with established chemical manufacturing industries (e.g., China, Europe, North America) may be more competitive compared to regions with limited chemical production capacity.

7.3 Price Trends

Monitoring price trends for DMCHA requires access to market reports and industry publications. Prices can fluctuate due to changes in supply and demand, raw material costs, and other economic factors. Contacting suppliers directly and requesting quotes is the best way to obtain current pricing information.

Indicative Price Range (Disclaimer: This is a general estimate and subject to change):

• Small quantities (e.g., 1-5 liters): $50-$150 per liter
• Bulk quantities (e.g., 200-liter drums): $20-$80 per liter
• Large quantities (e.g., ISO tanks): Prices are negotiated directly with the supplier and can be significantly lower.

Note: These are rough estimates and should not be considered definitive pricing. Always consult with chemical suppliers for current and accurate pricing.

8. Quality Control and Analysis

Ensuring the quality of DMCHA is crucial for its intended applications. Various analytical techniques are employed to determine its purity and identify any impurities.

8.1 Purity Determination

• Gas Chromatography (GC): GC is a widely used technique for determining the purity of DMCHA. It separates the components of the sample based on their boiling points and allows for quantification of the DMCHA content.
• Titration: Acid-base titration can be used to determine the amine content of DMCHA, providing an indication of its purity.
• Refractive Index Measurement: The refractive index of DMCHA is a characteristic property that can be used to assess its purity.
• Karl Fischer Titration: This technique is used to determine the water content of DMCHA, which is an important quality parameter.

8.2 Impurity Profile

Common impurities that may be present in DMCHA include:

• Cyclohexylamine
• N-Methylcyclohexylamine
• Cyclohexanone
• Water
• Other organic compounds

The levels of these impurities need to be carefully controlled to ensure that the DMCHA meets the required specifications for its intended application.

Table: Typical Analytical Techniques for DMCHA Quality Control

Analytical Technique	Parameter Measured	Information Provided
Gas Chromatography (GC)	Purity, Impurity Profile	Percentage of DMCHA, identification and quantification of impurities
Titration	Amine Content	Determination of basicity and purity
Refractive Index	Refractive Index	Confirmation of identity and indication of purity
Karl Fischer Titration	Water Content	Determination of water content, which can affect reactivity and stability

9. Regulatory Information

The regulatory status of DMCHA varies depending on the country and region. It is the responsibility of the user to ensure compliance with all applicable regulations regarding the handling, storage, and disposal of DMCHA.

• Transportation: DMCHA is typically classified as a hazardous material for transportation purposes and requires proper labeling and packaging.
• Environmental Regulations: Regulations may govern the release of DMCHA into the environment.
• Occupational Safety and Health (OSH) Regulations: OSH regulations specify requirements for workplace safety when handling DMCHA, including the use of PPE and ventilation.

10. Future Trends

Future trends in the DMCHA market are likely to be driven by the growing demand for polyurethanes in various applications, as well as by the increasing focus on sustainable and environmentally friendly chemical processes.

• Development of New Catalytic Applications: Research efforts may focus on exploring new catalytic applications of DMCHA in other chemical reactions.
• Development of More Sustainable Synthesis Methods: Efforts may be directed towards developing more sustainable and environmentally friendly synthesis methods for DMCHA, such as using bio-based raw materials or developing more efficient catalytic processes.
• Development of Modified DMCHA Derivatives: Development of DMCHA derivatives with improved catalytic activity, selectivity, or compatibility with specific polymer systems.

11. Conclusion

N,N-Dimethylcyclohexylamine (DMCHA) is a versatile tertiary amine with diverse applications in catalysis, polymer chemistry, and pharmaceutical research. Its unique properties, stemming from the combination of a cyclic aliphatic structure and a tertiary amine functionality, make it a valuable chemical intermediate and a functional reagent in diverse industrial processes. While DMCHA is a hazardous chemical and requires careful handling, its widespread applications and continued research efforts ensure its continued importance in various industries. Understanding its properties, synthesis, applications, and safety considerations is crucial for its safe and effective use. Obtaining accurate pricing information requires direct communication with chemical suppliers, as prices are influenced by various factors and can vary significantly across regions.

12. References

• Sheldon, R. A., & van Bekkum, H. (2007). Fine chemicals through heterogeneous catalysis. John Wiley & Sons.
• Oertel, G. (Ed.). (1993). Polyurethane handbook. Hanser Gardner Publications.
• Vogel, A. I. (1989). Vogel’s textbook of practical organic chemistry. Longman Scientific & Technical.
• Sigma-Aldrich Safety Data Sheet (SDS) for N,N-Dimethylcyclohexylamine.
• Specific chemical supplier catalogs and technical datasheets (references omitted due to restriction on external links).
• Relevant academic literature databases (e.g., Scopus, Web of Science) for research articles on DMCHA synthesis, applications, and properties (specific citations omitted to avoid external links).

Disclaimer: This article provides general information about N,N-Dimethylcyclohexylamine and should not be considered a substitute for professional advice. Always consult with qualified professionals and refer to relevant safety data sheets and regulations before handling or using this chemical. Pricing information is indicative and subject to change; contact chemical suppliers for current and accurate pricing.

Sales Contact：sales@newtopchem.com