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DESCRIPTION
Dicyclohexylamine (DCHA) is an organic compound with the chemical formula C12H23N.
Dicyclohexylamine (DCHA) is a tertiary amine derived from cyclohexane and is typically used as a chemical intermediate or a reagent in various industrial applications.
Cas Number
101-83-7
Synonyms
1,1'-Dicyclohexylamine,N,N-Dicyclohexylamine, DCHA,N-Cyclohexylcyclohexanamine,Cyclohexylamine, N-cyclohexyl-
Dicyclohexylamine (DCHA) is an organic compound derived from cyclohexylamine, featuring a cyclohexyl group attached to a nitrogen atom.
Dicyclohexylamine (DCHA) is used in various industrial applications, including as a corrosion inhibitor, surfactant, and intermediate in organic synthesis.
Due to its broad applicability and specific reactivity, DCHA plays a critical role in sectors such as pharmaceuticals, agriculture, and rubber manufacturing.
This article provides a comprehensive overview of DCHA, covering its chemical structure and properties, methods of synthesis, key applications, economic impact, toxicology, environmental effects, and analytical techniques for detection.
The article concludes with a discussion on future trends and innovations in DCHA usage.
Dicyclohexylamine (C₁₂H₂₃N), often abbreviated as DCHA, is a nitrogen-containing organic compound.
It is part of a broader class of amines, which are derived from ammonia, where the hydrogen atoms are substituted by hydrocarbon groups.
DCHA is synthesized by reacting cyclohexylamine with cyclohexyl chloride or other compounds containing a cyclohexyl group.
This compound is colorless to pale yellow in its pure form and has an aromatic odor.
Its industrial relevance comes from its diverse applications, including in the manufacturing of rubber, as a surfactant, in corrosion inhibition, and as a precursor for pharmaceuticals.
DCHA is also used in several research domains, such as the synthesis of complex organic molecules and materials.
Despite its usefulness, DCHA poses certain environmental and health risks, which necessitate a comprehensive understanding of its properties and effects.
Chemical Structure and Properties
Dicyclohexylamine consists of two cyclohexyl groups (C₆H₁₁) attached to a nitrogen atom.
The molecular structure of DCHA can be represented as (C₆H₁₁)₂NH, where the nitrogen atom is bonded to two cyclohexyl rings.
The compound belongs to the class of secondary amines, where the nitrogen atom is bound to two carbon atoms, making it different from primary amines.
In terms of physical properties, DCHA has a high boiling point of around 267°C, indicating its stability at high temperatures.
It is slightly soluble in water but readily soluble in organic solvents like ethanol, acetone, and chloroform.
DCHA has a faint, somewhat sweet, and pungent odor due to the cyclohexyl groups.
Its stability can be attributed to the steric hindrance created by the bulky cyclohexyl groups, which prevent the compound from reacting easily with other chemicals.
Synthesis of Dicyclohexylamine
Dicyclohexylamine can be synthesized through various methods, with the most common process involving the reaction between cyclohexylamine and cyclohexyl chloride.
This method yields a high purity of DCHA but requires careful temperature control and excess reagents to optimize yield.
Another method involves the catalytic hydrogenation of N-cyclohexyl imines in the presence of hydrogen and a suitable catalyst.
Both processes allow for scalable production suitable for industrial use, though optimization is necessary to reduce by-products and enhance yield.
Applications
Dicyclohexylamine's versatility is evident in its wide range of applications.
In the rubber industry, it is commonly used as a curing agent and a component in the production of vulcanizing agents, which crosslink rubber polymers, making the material more durable.
It also serves as an emulsifier in the manufacturing of latex products.
In the oil and gas industry, DCHA is utilized as a dispersant and corrosion inhibitor, protecting equipment from damage caused by the acidic conditions of oil drilling operations.
Furthermore, DCHA acts as a catalyst or reagent in the synthesis of pharmaceuticals, where it is used in the production of various active pharmaceutical ingredients (APIs) by facilitating nucleophilic substitutions.
In agriculture, DCHA is used as a precursor in the synthesis of certain pesticides and herbicides.
It has also found uses in polymer synthesis, where it acts as a stabilizer or cross-linking agent, providing materials with enhanced mechanical properties.
Industrial Uses and Economic Impact
Dicyclohexylamine plays a pivotal role in several industries, especially in the production of rubber, chemicals, and pharmaceuticals.
The rubber industry uses DCHA in the production of accelerators, anti-aging agents, and vulcanizing agents, contributing to the creation of more durable rubber products like tires and seals.
The surfactant industry benefits from DCHA’s properties in the formulation of detergents and cleaners, where it aids in emulsifying oils and dirt.
The corrosion inhibitor application of DCHA has gained traction in industries reliant on metalworking and oil production, as it helps prevent the degradation of metals in contact with harsh chemicals.
Economically, DCHA is produced by major chemical manufacturers around the world, with a large portion of production directed toward the rubber industry.
The demand for DCHA is tied to global industrial growth, particularly in sectors like automotive, oil, and consumer goods. The compound is also essential in maintaining efficiency and longevity in machinery, which adds to its overall market value.
Analytical Techniques for Detection and Quantification
The detection and quantification of Dicyclohexylamine in various matrices (e.g., water, air, soil, and biological tissues) require precise analytical techniques.
Gas chromatography (GC) coupled with flame ionization detection (FID) is one of the most commonly used methods for separating and identifying DCHA in complex mixtures.
High-performance liquid chromatography (HPLC) is another effective method, often used for quantifying DCHA in pharmaceutical preparations.
Spectroscopic techniques such as nuclear magnetic resonance (NMR) spectroscopy provide valuable information about the molecular structure of DCHA and can detect impurities or by-products in a sample.
Infrared (IR) spectroscopy can also identify functional groups present in the compound.
Mass spectrometry (MS), often combined with GC or HPLC, allows for the high sensitivity detection of DCHA and its breakdown products in trace amounts.
Research Trends and Future Directions
Current research on Dicyclohexylamine is focused on enhancing its synthesis methods and discovering more sustainable and cost-effective approaches.
One key area of interest is the development of green chemistry methods for the production of DCHA, reducing the need for harmful reagents and solvents while improving yields.
Moreover, the safe handling of DCHA remains a priority in industrial settings, leading to studies aimed at minimizing exposure risks to workers.
Researchers are also exploring new applications for DCHA in materials science, such as in the synthesis of advanced polymers and nanomaterials, which could benefit from the unique properties of the compound.
Additionally, there is growing interest in the use of DCHA derivatives in the development of new drug molecules, as its reactivity with various functional groups allows for the creation of diverse medicinal compounds.
Dicyclohexylamine is a versatile compound with significant importance across a variety of industrial applications.
Its chemical structure imparts stability and unique reactivity, making it invaluable in fields such as rubber manufacturing, pharmaceuticals, and chemical synthesis.
However, the potential environmental and health risks associated with its use demand careful management and adherence to safety protocols.
As research continues, the development of greener, safer alternatives and new applications promises to enhance the future prospects of DCHA, ensuring its continued relevance in the industrial and scientific sectors.
SAFETY INFORMATION ABOUT DICYCLOHEXYLAMINE (DCHA)
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product.
