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DESCRIPTION
Tetramethyldipropylenetriamine is a chemical compound that belongs to the class of organic amines.
Its chemical structure consists of a dipropylene triamine backbone with four methyl groups attached to nitrogen atoms.
This molecule is primarily used as a curing agent in epoxy resin formulations, and it can also function as a catalyst in various chemical reactions.
CAS NUMBER
6711-48-4 PC15
SYNONYMS
Tetramethyldipropylenetriamine,CW8R6R660G,6711-48-4, 1,3-Propanediamine, N'-(3-(dimethylamino)propyl)-N,N-dimethyl-,N'-(3-(Dimethylamino)propyl)-N,N-dimethylpropane-1,3-diamine,Dipropylenetriamine, N,N,N',N'-tetramethyl-,AI3-16566,Bis-(dimethylaminopropyl)amine,Bis(3dimethylaminopropyl)amine,Bis(3-dimethylamino-1-propyl)amine,BRN 0635876,N'-(3-(Dimethylamino)propyl)-N,N-dimethyl-1,3-propanediamine,EINECS 229-761-9,NSC 129937,N,N,N',N'-Tetramethyldipropylenetriamine,2,6,10-Triazaundecane, 2,10,dimethyl-3-04-00-00565 (Beilstein Handbook Reference),1,3-Propanediamine, N3-(3-(dimethylamino)propyl)-N1,N1-dimethyl-,UNII-CW8R6R660G,EC 229-761-9,Dipropylamine, 3,3'-bis(dimethylamino)-
1. INTRODUCTION
Background of TM-DPT:
Definition and Chemical Structure:
Tetramethyl Dipropylene Triamine (TM-DPT) is an organic compound containing nitrogen and carbon atoms, specifically a tri-functional amine structure.
The compound’s molecular formula is C10H23N3, and it features a dipropylene backbone with a tetramethyl substitution at the nitrogen atoms.
The unique chemical structure makes it highly versatile in various chemical reactions and industrial applications.
Historical Context and Development:
TM-DPT was first synthesized in the mid-20th century as part of research into specialized organic compounds used for industrial applications.
Over time, its chemical properties have been better understood, leading to its widespread usage, particularly in corrosion inhibition and polymerization processes.
Importance in Various Industries:
Industrial Uses:
TM-DPT has gained prominence for its applications in chemical synthesis, where its role as a crosslinking agent and catalyst is critical.
It is also used in metalworking fluids, where it acts as a corrosion inhibitor.
Relevance to Scientific Research:
Research into TM-DPT's behavior, particularly its reaction with metals and other molecules, continues to drive innovation in fields such as material science and chemical engineering.
2. CHEMICAL AND PHYSICAL PROPERTIES
Molecular Structure and Composition:
Analysis of the Chemical Formula:
TM-DPT consists of a dipropylene backbone (C6H12) with nitrogen atoms substituted at strategic locations, forming a tri-functional amine.
The methyl groups attached to the nitrogen atoms (tetramethyl) provide steric protection, making the compound more stable and reactive under specific conditions.
Bonding and Electronic Structure:
TM-DPT has a series of nitrogen-carbon bonds and displays electron-donating characteristics through its nitrogen atoms, which play a crucial role in coordination chemistry and interaction with metal ions.
Physical Properties:
Melting Point, Boiling Point, and Solubility:
The compound has a relatively high melting point, indicating its solid-state stability.
It is soluble in both polar and nonpolar solvents, which makes it versatile for different applications.
These properties are key to its behavior in industrial processes.
Color, Odor, and Appearance:
TM-DPT typically appears as a clear to light yellow liquid, with a mild, amine-like odor.
Its appearance can vary slightly depending on the purity and formulation.
Spectroscopic Properties:
IR (Infrared) Spectroscopy:
The infrared spectrum of TM-DPT reveals key functional groups, such as amines and methyl groups, and can be used to determine its purity and structural integrity.
NMR (Nuclear Magnetic Resonance):
Proton NMR and Carbon-13 NMR spectra provide insights into the molecule’s chemical environment, confirming the placement of the methyl groups and the tri-functional nitrogen atoms.
UV-Vis (Ultraviolet-Visible):
Absorption spectra can help identify the molecule’s potential for UV absorption, which is relevant in applications involving light exposure, such as coatings or polymers.
3. SYNTHESIS OF TETRAMETHYL DIPROPYLENE TRIAMINE
Synthetic Pathways:
Common Methods of Synthesis:
TM-DPT is typically synthesized via a multi-step process, involving the reaction of dipropylene triamine with methylating agents, such as methyl iodide or dimethyl sulfate.
These reagents introduce the methyl groups at the nitrogen positions.
Chemical Reactions Involved:
The primary reaction is the alkylation of the amine groups, where the dipropylene triamine (which has two reactive amine groups) undergoes nucleophilic substitution with a methyl donor, forming the tetramethyl-substituted triamine.
Precursors and Reagents:
Necessary Chemicals and Reagents:
The synthesis typically requires dipropylene triamine as the base material, with methylating agents like methyl iodide or dimethyl sulfate, along with solvents such as acetonitrile or ethanol to facilitate the reaction.
Yield and Purity:
Optimization of Yields and Purification Techniques:
Maximizing yield involves controlling the reaction temperature and time, as well as ensuring that the methylating agent is present in excess. After synthesis, TM-DPT can be purified by recrystallization or distillation to remove impurities, ensuring high purity for industrial or laboratory use.
4. MECHANISM OF ACTION
Reaction Mechanisms:
Mechanistic Steps in Primary Reactions:
In corrosion inhibition, TM-DPT acts by forming a protective film over the metal surface, reducing the rate of oxidation by interacting with metal ions.
It achieves this through coordination with metal surfaces, where its amine groups act as electron donors.
Interactions with Other Chemicals:
TM-DPT can participate in crosslinking reactions, where its amine groups react with other compounds, such as epoxies or polyurethanes, forming a network structure.
Role as a Ligand:
Binding Properties:
TM-DPT’s nitrogen atoms, with their lone pairs of electrons, allow it to bind with metal ions, forming complexes that are useful in catalytic processes or metal corrosion inhibition.
This ligand behavior is a key factor in its industrial applications.
Interactions with Metal Ions:
It forms stable complexes with transition metals such as copper, zinc, and iron, making it highly effective in preventing corrosion, especially in aqueous environments.
Catalytic Properties:
Application in Catalysis:
TM-DPT has been used as a ligand in catalytic processes, including reactions in the fine chemical industry.
It can help in the catalysis of polymerization reactions or in enhancing the reactivity of certain chemical processes through its interaction with metal catalysts.
5. INDUSTRIAL APPLICATIONS
Corrosion Inhibition:
Role in Corrosion Protection:
One of the primary industrial uses of TM-DPT is as a corrosion inhibitor in industries like oil and gas, automotive, and aerospace.
It forms a thin protective layer on metal surfaces, preventing the oxidative degradation of metals.
Comparison with Other Corrosion Inhibitors:
TM-DPT is compared to other corrosion inhibitors like amines and phosphates.
Studies show that it offers superior protection under specific conditions, such as high humidity or acidic environments.
Polymerization and Chemical Synthesis:
Use in Polymer Production:
TM-DPT is employed in polymer chemistry to control the crosslinking of polymer chains, especially in the production of thermosetting plastics.
Its triamine structure facilitates the formation of dense networks within polymer matrices.
Role as a Crosslinking Agent:
In the synthesis of certain resins and adhesives, TM-DPT’s amine groups act as crosslinking agents, improving the mechanical properties of the final polymer.
Oilfield Applications:
Use in Oil Recovery:
In the oil and gas industry, TM-DPT is used in drilling fluids to control corrosion and in the formulation of wellbore fluids that reduce the wear and tear on equipment.
It also helps in maintaining the integrity of pipelines and other equipment.
Other Applications:
Emerging Uses:
Researchers are exploring its use in areas such as agriculture (as a pesticide or fungicide), biomedicine (as a stabilizer or additive), and renewable energy technologies (e.g., in fuel cells or batteries).
6. ENVIRONMENTAL IMPACT AND SAFETY CONSIDERATIONS
Toxicology:
Toxicity Studies:
The toxicity of TM-DPT has been studied in both acute and chronic exposure scenarios.
It has shown low toxicity when used within the recommended concentrations, but excessive exposure may lead to skin irritation or respiratory issues.
Toxicological Data:
Studies suggest that TM-DPT is not significantly toxic to aquatic organisms, though care should be taken to prevent contamination of water sources.
Environmental Fate and Behavior:
Degradation in the Environment:
TM-DPT is biodegradable under aerobic conditions, though its rate of degradation can be influenced by environmental factors such as temperature and pH.
Persistence and Bioaccumulation:
It is not expected to bioaccumulate significantly in aquatic environments, but its persistence in soil or water may vary depending on local conditions.
Health and Safety Precautions:
Handling and Storage:
TM-DPT should be stored in a cool, dry place and handled in a well-ventilated area.
Personal protective equipment (PPE) such as gloves, goggles, and respiratory protection should be used when handling this chemical.
Regulatory Status and Guidelines:
TM-DPT is regulated by agencies like the EPA and OSHA, which set limits on exposure levels and require proper labeling for safety during transportation and use.
7. ANALYTICAL METHODS FOR DETECTION AND QUANTIFICATION
Chromatographic Techniques:
High-Performance Liquid Chromatography (HPLC):
TM-DPT can be separated and quantified using reverse-phase HPLC, with UV detection at specific wavelengths corresponding to its functional groups.
Gas Chromatography-Mass Spectrometry (GC-MS):
This method can be used to analyze the purity of TM-DPT or detect any degradation products in environmental or industrial samples.
Spectroscopic Methods:
NMR Spectroscopy:
NMR spectroscopy can be used for structural characterization, confirming the presence of key functional groups and verifying the purity of TM-DPT in synthesized samples.
UV-Vis Spectroscopy:
UV-Vis spectroscopy helps in identifying the light absorption characteristics of TM-DPT and its derivatives.
Other Detection Techniques:
Electrochemical Methods:
Electrochemical sensors can detect the concentration of TM-DPT in various mediums, particularly in corrosion studies.
8. RESEARCH AND DEVELOPMENT
Recent Advancements:
New Uses and Applications:
Recent studies have explored TM-DPT’s role in advanced materials, such as nanomaterials, and its potential as a stabilizer in new chemical reactions.
Potential Areas of Future Research:
Future Innovations:
Ongoing research aims to improve the synthesis methods of TM-DPT for higher yields, explore new applications in catalysis, and evaluate its long-term environmental impact.
9. CONCLUSION
Summary of Key Points:
TM-DPT’s unique chemical structure and functional properties make it invaluable in a variety of industrial and scientific applications, from corrosion inhibition to polymer production.
Outlook for the Future:
Continued advancements in TM-DPT’s synthesis and applications will drive further growth in industries like oil and gas, materials science, and chemical manufacturing, with increased focus on sustainability and safety.
SAFETY INFORMATION ABOUT TETRAMETHYLDIPROPYLENETRIAMINE
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
