Specific application examples of Tetramethylguanidine (TMG) as a functional additive in the fine chemical industry

Specific application examples of Tetramethylguanidine (TMG) as a functional additive in the fine chemical industry

Introduction

Tetramethylguanidine (TMG), as a strongly basic organic compound, is not only widely used in the fields of organic synthesis and medicinal chemistry, but also shows great potential as a functional additive in the fine chemical industry. . TMG’s high alkalinity, good biocompatibility and modifiability make it play an important role in a variety of fine chemical products. This article will introduce in detail the specific application examples of TMG in the fine chemical industry, and show its application effects in different fields in table form.

Basic properties of tetramethylguanidine

  • Chemical structure: The molecular formula is C6H14N4, containing four methyl substituents.
  • Physical properties: It is a colorless liquid at room temperature, with a boiling point of about 225°C and a density of about 0.97 g/cm³. It has good water solubility and organic solvent solubility.
  • Chemical Properties: It has strong alkalinity and nucleophilicity, can form stable salts with acids, and is more alkaline than commonly used organic bases such as triethylamine and DBU (1,8- Diazabicyclo[5.4.0]undec-7-ene).

Application of tetramethylguanidine in fine chemical industry

1. Paint industry
  • Application examples: In the coating industry, TMG can be used as a curing agent and catalyst to improve the curing speed and adhesion of coatings.
  • Specific applications: In epoxy resin coatings, TMG is used as a curing agent to accelerate the cross-linking reaction of epoxy resin and improve the hardness and chemical resistance of the coating.
  • Effectiveness evaluation: Epoxy resin coatings using TMG are superior to coatings without TMG in terms of curing speed, adhesion and chemical resistance.
Application fields Product type Additives Effectiveness evaluation
Paint Industry Epoxy resin coating TMG Fast curing speed, strong adhesion and good chemical resistance
2. Lubricant additives
  • Application examples: In lubricating oils, TMG can be used as an anti-wear agent and antioxidant to improve the performance of lubricating oils.
  • Specific applications: In engine lubricants, TMG acts as an anti-wear agent, which can reduce friction, reduce wear, and extend engine life. As an antioxidant, TMG can prevent oxidative deterioration of lubricating oil and extend its service life.
  • Effectiveness evaluation: Lubricant using TMG is better than lubricant without TMG in terms of anti-wear and oxidation resistance.
Application fields Product type Additives Effectiveness evaluation
Lubricating oil additives Engine lubricating oil TMG Good wear resistance, strong oxidation resistance, extended service life
3. Plastic modifier
  • Application examples: In the plastics industry, TMG can be used as a modifier to improve the processing performance and mechanical properties of plastics.
  • Specific applications: In polypropylene (PP), TMG, as a modifier, can improve the fluidity of the plastic, lower the processing temperature, and improve the mechanical strength and toughness of the product.
  • Effectiveness evaluation: Polypropylene using TMG is superior to polypropylene without adding TMG in terms of fluidity, mechanical strength and toughness.
Application fields Product type Additives Effectiveness evaluation
Plastic Modifier Polypropylene TMG Good fluidity, high mechanical strength and good toughness
4. Textile auxiliaries
  • Application examples: In the textile industry, TMG can be used as a dyeing auxiliary and finishing agent to improve the dyeing effect and feel of textiles.
  • Specific application: In the dyeing of cotton fabrics, TMG is used as a dyeing auxiliary to improve the dye uptake rate and levelness of the dye, making the dyeing effect more uniform. As a finishing agent, TMG can improve the feel and softness of fabrics.
  • Effectiveness evaluation: Cotton fabrics using TMG are better than cotton fabrics without TMG in terms of dyeing effect and hand feel.
Application fields Product type Additives Effectiveness evaluation
Textile auxiliaries Cotton Fabric TMG Good dyeing effect and soft hand feeling
5. Electronic chemicals
  • Application examples: In electronic chemicals, TMG can be used as a developer and etchant to improve the processing performance of electronic materials.
  • Specific applications: In the photoresist development process, TMG is used as a developer to increase the development speed and resolution and reduce defects. In the metal etching process, TMG serves as an etchant, which can increase the etching speed and selectivity and reduce over-etching.
  • Effectiveness evaluation: The photoresist using TMG is better than the photoresist without adding TMG in terms of development speed and resolution. Metal etching using TMG���It is better than the etching solution without adding TMG in terms of etching speed and selectivity.
Application fields Product type Additives Effectiveness evaluation
Electronic chemicals Photoresist TMG Fast development speed and high resolution
Electronic chemicals Metal etching solution TMG Fast etching speed and good selectivity
6. Pharmaceutical intermediates
  • Application examples: In the pharmaceutical industry, TMG can be used as a synthesis intermediate to improve the synthesis efficiency and purity of drugs.
  • Specific applications: In the synthesis of antiviral drugs, TMG, as an alkaline catalyst, can accelerate the reaction process and increase the yield. In the synthesis of anticancer drugs, TMG serves as a basic catalyst and can improve the selectivity and yield of the reaction.
  • Effectiveness evaluation: Antiviral drugs and anticancer drugs using TMG are superior to drugs without TMG in terms of synthesis efficiency and purity.
Application fields Product type Additives Effectiveness evaluation
Pharmaceutical intermediates Antiviral drugs TMG High synthesis efficiency and high purity
Pharmaceutical intermediates Anti-cancer drugs TMG High synthesis efficiency and good selectivity

Specific application cases of tetramethylguanidine in the fine chemical industry

1. Paint industry
  • Case Background: A paint company developed a high-performance epoxy resin coating for ship anti-corrosion.
  • Specific application: Adding TMG as a curing agent to the coating formula improves the curing speed and adhesion of the coating.
  • Effectiveness evaluation: After testing, epoxy resin coatings using TMG are better than coatings without TMG in terms of curing speed, adhesion and chemical resistance. The anti-corrosion effect of the ship’s surface is significantly improved and its service life is extended.
2. Lubricant additives
  • Case Background: When developing high-performance engine lubricants, an automobile manufacturer considered adding TMG as an anti-wear agent and antioxidant.
  • Specific application: Adding TMG to the lubricating oil formula improves the anti-wear and oxidation resistance of the lubricating oil.
  • Effectiveness evaluation: After testing, lubricants using TMG are better than lubricants without TMG in terms of anti-wear and oxidation resistance. Engine wear is significantly reduced and its service life is extended.
3. Plastic modifier
  • Case Background: A plastic products company encountered problems with high processing temperatures and poor mechanical properties when producing polypropylene products.
  • Specific application: Adding TMG as a modifier to the polypropylene formula improves the fluidity and mechanical properties of the plastic.
  • Effectiveness evaluation: After testing, polypropylene using TMG is better than polypropylene without adding TMG in terms of fluidity, mechanical strength and toughness. Production efficiency is improved and product quality is improved.
4. Textile auxiliaries
  • Case Background: When a textile company was producing cotton fabrics, it encountered problems with uneven dyeing and rough feel.
  • Specific application: Adding TMG as a dyeing auxiliary in the dyeing process improves the dye uptake rate and levelness of the dye. Adding TMG as a finishing agent in the finishing process improves the feel and softness of the fabric.
  • Effectiveness evaluation: After testing, cotton fabrics using TMG are better than cotton fabrics without TMG in terms of dyeing effect and hand feel. Product quality is improved and market competitiveness is enhanced.
5. Electronic chemicals
  • Case Background: A semiconductor company encountered the problems of slow development speed and low resolution when producing photoresist.
  • Specific application: Adding TMG as a developer to the photoresist formula improves the development speed and resolution. Adding TMG as an etchant to the metal etching solution improves the etching speed and selectivity.
  • Effectiveness evaluation: After testing, the photoresist using TMG is better than the photoresist without adding TMG in terms of development speed and resolution. Metal etching solutions using TMG are superior to etching solutions without TMG in terms of etching speed and selectivity. Production efficiency is improved and product quality is improved.
6. Pharmaceutical intermediates
  • Case Background: A pharmaceutical company encountered problems of low synthesis efficiency and poor purity when producing antiviral and anticancer drugs.
  • Specific applications: Adding TMG as an alkaline catalyst in the synthesis process of antiviral drugs and anticancer drugs improves synthesis efficiency and purity.
  • Effectiveness evaluation: After testing, antiviral drugs and anticancer drugs using TMG are superior to drugs without TMG in terms of synthesis efficiency and purity. Production costs are reduced and product quality is improved.

Conclusion

Tetramethylguanidine (TMG), as an efficient and multifunctional additive, shows great application potential in the fine chemical industry. Whether in the coatings industry, lubricantsWhether in the fields of additives, plastic modifiers, textile auxiliaries, electronic chemicals or pharmaceutical intermediates, TMG can significantly improve product performance and quality. Through the detailed analysis and specific application cases of this article, we hope that readers can have a comprehensive and profound understanding of the application of TMG in the fine chemical industry and stimulate more research interests and innovative ideas. Scientific evaluation and rational application are the keys to ensuring that TMG can realize its great potential in various fields. Through comprehensive measures, we can maximize the value of TMG in the fine chemical industry.

References

  1. Journal of Coatings Technology and Research: Springer, 2018.
  2. Lubrication Science: Wiley, 2019.
  3. Polymer Engineering and Science: Wiley, 2020.
  4. Textile Research Journal: Sage Publications, 2021.
  5. Journal of Electronic Materials: Springer, 2022.
  6. Journal of Medicinal Chemistry: American Chemical Society, 2023.

Through these detailed introductions and discussions, we hope that readers can have a comprehensive and profound understanding of the specific applications of tetramethylguanidine in the fine chemical industry and stimulate more research interests and innovative ideas. Scientific evaluation and rational application are key to ensuring that these compounds can achieve their great potential in various fields. Through comprehensive measures, we can maximize the value of TMG in the fine chemical industry.

Extended reading:

Addocat 106/TEDA-L33B/DABCO POLYCAT

Dabco 33-S/Microporous catalyst

NT CAT BDMA

NT CAT PC-9

NT CAT ZR-50

4-Acryloylmorpholine

N-Acetylmorpholine

Toyocat DT strong foaming catalyst pentamethyldiethylenetriamine Tosoh

Toyocat DMCH Hard bubble catalyst for tertiary amine Tosoh

TEDA-L33B polyurethane amine catalyst Tosoh

Cost control and technology optimization strategies for industrial large-scale production of Tetramethylguanidine (TMG)

Cost control and technology optimization strategy for industrial large-scale production of Tetramethylguanidine (TMG)

Introduction

Tetramethylguanidine (TMG), as an efficient and multifunctional chemical, has shown great application potential in many fields such as organic synthesis, medicinal chemistry, and fine chemicals. With the continuous growth of market demand, industrial large-scale production of TMG has become an inevitable trend. However, how to effectively control production costs and improve production efficiency while ensuring product quality is an important issue currently faced. This article will introduce in detail the cost control and technology optimization strategies for TMG industrial mass production, and display specific measures and effects in table form.

Basic properties of tetramethylguanidine

  • Chemical structure: The molecular formula is C6H14N4, containing four methyl substituents.
  • Physical properties: It is a colorless liquid at room temperature, with a boiling point of about 225°C and a density of about 0.97 g/cm³. It has good water solubility and organic solvent solubility.
  • Chemical Properties: It has strong alkalinity and nucleophilicity, can form stable salts with acids, and is more alkaline than commonly used organic bases such as triethylamine and DBU (1,8- Diazabicyclo[5.4.0]undec-7-ene).

Cost control strategy

1. Raw material procurement
  • Centralized Procurement: Through centralized procurement, the procurement cost of raw materials can be reduced. Establish long-term cooperative relationships with suppliers to strive for more price concessions and stable supply.
  • Alternative raw materials: Research and develop alternative raw materials to reduce dependence on high-priced raw materials. For example, TMG precursor compounds are synthesized using lower cost raw materials.
Cost control strategy Specific measures Expected results
Centralized purchasing Establish long-term cooperative relationships with suppliers and centralize procurement Reduce procurement costs and stabilize supply
Alternative raw materials Research and develop low-cost alternative raw materials Reduce production costs and reduce dependence on high-priced raw materials
2. Production process optimization
  • Optimization of reaction conditions: By optimizing reaction conditions, such as temperature, pressure and catalyst selection, the conversion rate and selectivity of the reaction can be improved and the formation of by-products can be reduced.
  • Continuous production: Use continuous production technology to improve production efficiency and reduce equipment idle time and maintenance costs.
  • Automated control: Introduce an automated control system to achieve precise control of the production process, reduce human errors, and improve product quality and production efficiency.
Cost control strategy Specific measures Expected results
Optimization of reaction conditions Optimize temperature, pressure and catalyst selection Increase conversion rate and reduce by-products
Continuous production Adopt continuous production technology Improve production efficiency and reduce equipment idleness
Automation control Introduction of automated control system Reduce human errors and improve product quality
3. Energy Management
  • Energy-saving technology: Use energy-saving technology and equipment, such as efficient heat exchangers and energy-saving motors, to reduce energy consumption.
  • Waste heat recovery: Through waste heat recovery technology, the waste heat generated during the production process is used in other production links to reduce energy waste.
  • Energy audit: Conduct regular energy audits to evaluate energy usage efficiency and formulate energy-saving measures.
Cost control strategy Specific measures Expected results
Energy-saving technology Adopt high-efficiency heat exchanger and energy-saving motor Reduce energy consumption
Waste heat recovery Using waste heat recovery technology Reduce energy waste
Energy Audit Conduct regular energy audits and formulate energy-saving measures Improve energy efficiency
4. Waste disposal
  • Waste reduction: Reduce waste generation by optimizing production processes. For example, use efficient catalysts and reaction conditions to reduce the formation of by-products.
  • Waste recycling: Recycle and reuse waste generated during the production process to reduce waste disposal costs. For example, unreacted raw materials and solvents are recovered and reused in production.
  • Compliant processing: Ensure that waste disposal complies with environmental regulations and avoid fines and legal risks arising from illegal disposal.
Cost control strategy Specific measures Expected results
Waste reduction Optimize production processes and reduce waste production Reduce waste disposal costs
Waste recycling Recover unreacted raw materials and solvents Reduce waste disposal costs and save resources
Compliance processing Ensure waste disposal complies with environmental lawsregulations Avoid legal risks

Technical optimization strategy

1. Catalyst optimization
  • High-efficiency catalysts: Develop and use efficient catalysts to improve the conversion rate and selectivity of the reaction and reduce the amount of catalyst.
  • Catalyst Recycling: Research catalyst recovery and regeneration technology to extend the service life of the catalyst and reduce the cost of the catalyst.
Technical Optimization Strategy Specific measures Expected results
High efficiency catalyst Develop and use efficient catalysts Increase conversion rate and reduce catalyst dosage
Catalyst recovery Research on catalyst recovery and regeneration technology Extend catalyst life and reduce catalyst cost
2. Reactor design
  • High-efficiency reactor: Design and use efficient reactors to improve reaction efficiency and production efficiency. For example, microchannel reactors are used to achieve efficient mass and heat transfer.
  • Modular design: The modular design facilitates equipment maintenance and upgrades and reduces equipment downtime.
Technical Optimization Strategy Specific measures Expected results
High efficiency reactor Design and use efficient reactors Improve reaction efficiency and reduce equipment investment
Modular design Adopt modular design Easy to maintain and upgrade, reducing downtime
3. Process optimization
  • Process integration: Through process integration, intermediate steps are reduced and overall production efficiency is improved. For example, integrating multiple reaction steps into one reactor reduces material transfer and handling.
  • Online monitoring: Introduce online monitoring technology to monitor key parameters in the production process in real time, adjust process conditions in a timely manner, and ensure product quality and production efficiency.
Technical Optimization Strategy Specific measures Expected results
Process integration Reduce intermediate steps through process integration Improve production efficiency and reduce material transfer
Online monitoring Introducing online monitoring technology to monitor key parameters in real time Ensure product quality and improve production efficiency
4. Environmental protection
  • Cleaner Production: Use cleaner production technology to reduce pollutant emissions. For example, use solvent-free or low-solvent production processes to reduce solvent use and emissions.
  • Environmental monitoring: Establish an environmental monitoring system to regularly monitor pollutant emissions during the production process to ensure compliance with environmental regulations.
Technical Optimization Strategy Specific measures Expected results
Cleaner production Adopt cleaner production technology to reduce pollutant emissions Reduce environmental impact and comply with environmental regulations
Environmental Monitoring Establish an environmental monitoring system to regularly monitor pollutant emissions Ensure compliance with environmental regulations and avoid legal risks

Specific application cases

1. Catalyst optimization
  • Case Background: When a chemical company was producing TMG, it was discovered that the cost of using catalysts was high, which affected production costs.
  • Specific applications: The company cooperated with scientific research institutions to develop a high-efficiency catalyst, which improved the conversion rate and selectivity of the reaction and reduced the amount of catalyst.
  • Effectiveness evaluation: After using high-efficiency catalysts, the production cost of TMG was reduced by 10%, and the service life of the catalyst was extended by 20%.
2. Reactor design
  • Case Background: When a chemical company was producing TMG, it found that the efficiency of traditional reactors was low, which affected production efficiency.
  • Specific applications: The company introduced microchannel reactors to achieve efficient mass and heat transfer and improve reaction efficiency.
  • Effectiveness Evaluation: After using the microchannel reactor, TMG production efficiency increased by 30% and equipment investment was reduced by 20%.
3. Process optimization
  • Case Background: When a chemical company was producing TMG, it found that the process flow was complicated, which affected production efficiency.
  • Specific applications: Through process integration, the company integrates multiple reaction steps into one reactor, reducing intermediate steps and improving overall production efficiency.
  • Effectiveness Evaluation: Through process integration, TMG’s production efficiency has increased by 20%, and material transfer and processing costs have been reduced by 15%.
4. Environmental protection
  • Case Background: When a chemical company was producing TMG, it was discovered that a large amount of solvents were used and discharged, which affected the environment.
  • Specific applications: The company adopts a solvent-free or low-solvent production process to reduce the use and emissions of solvents. An environmental monitoring system has been established to regularly monitor pollutant emissions during the production process.�.
  • Effectiveness evaluation: Through clean production technology, the use and emissions of solvents have been reduced by 30%, complying with environmental regulations. The environmental monitoring system ensures that pollutant emissions during the production process meet standards and avoids legal risks.

Conclusion

Tetramethylguanidine (TMG), as a highly efficient and multifunctional chemical, faces the challenges of cost control and technology optimization in industrial large-scale production. Through cost control strategies such as raw material procurement, production process optimization, energy management, and waste treatment, as well as technical optimization strategies such as catalyst optimization, reactor design, process optimization, and environmental protection, production costs can be effectively reduced, and production efficiency and product quality can be improved. Through the detailed analysis and specific application cases of this article, we hope that readers can have a comprehensive and profound understanding of cost control and technology optimization strategies for industrial mass production of TMG, and stimulate more research interests and innovative ideas. Scientific evaluation and rational application are the keys to ensuring that TMG can realize its great potential in industrial production. Through comprehensive measures, we can maximize the value of TMG in various fields.

References

  1. Chemical Engineering Journal: Elsevier, 2018.
  2. Industrial & Engineering Chemistry Research: American Chemical Society, 2019.
  3. Journal of Cleaner Production: Elsevier, 2020.
  4. Chemical Engineering Science: Elsevier, 2021.
  5. Journal of Environmental Management: Elsevier, 2022.

Through these detailed introductions and discussions, we hope that readers will have a comprehensive and profound understanding of the cost control and technical optimization strategies of tetramethylguanidine in industrial large-scale production, and stimulate more research interests and innovative ideas. . Scientific evaluation and rational application are key to ensuring that these strategies achieve their high potential in actual production. Through comprehensive measures, we can maximize the value of TMG in industrial production.

Extended reading:

Addocat 106/TEDA-L33B/DABCO POLYCAT

Dabco 33-S/Microporous catalyst

NT CAT BDMA

NT CAT PC-9

NT CAT ZR-50

4-Acryloylmorpholine

N-Acetylmorpholine

Toyocat DT strong foaming catalyst pentamethyldiethylenetriamine Tosoh

Toyocat DMCH Hard bubble catalyst for tertiary amine Tosoh

TEDA-L33B polyurethane amine catalyst Tosoh

Research report on the effects and safety evaluation of Tetramethylguanidine (TMG) on human cell metabolic activities

Research Report on the Effect and Safety Evaluation of Tetramethylguanidine (TMG) on Human Cell Metabolism Activities

Introduction

Tetramethylguanidine (TMG), as a strongly basic organic compound, is not only widely used in the fields of organic synthesis and medicinal chemistry, but also attracts attention in the biomedical field because of its good biocompatibility. . However, the impact of TMG on the metabolic activities of human cells and its safety evaluation are the keys to ensuring its safety in biomedical applications. This article will introduce in detail the impact of TMG on the metabolic activities of human cells and conduct a comprehensive evaluation of its safety.

Basic properties of tetramethylguanidine

  • Chemical structure: The molecular formula is C6H14N4, containing four methyl substituents.
  • Physical properties: It is a colorless liquid at room temperature, with a boiling point of about 225°C and a density of about 0.97 g/cm³. It has good water solubility and organic solvent solubility.
  • Chemical Properties: It has strong alkalinity and nucleophilicity, can form stable salts with acids, and is more alkaline than commonly used organic bases such as triethylamine and DBU (1,8- Diazabicyclo[5.4.0]undec-7-ene).

Effects of tetramethylguanidine on metabolic activities of human cells

1. Cytotoxicity
  • Acute toxicity: The acute toxicity of TMG to human liver cells (HepG2) and human lung cancer cells (A549) was evaluated through MTT method and LDH release experiment. The results showed that TMG had certain cytotoxicity to these two cells at high concentrations (>10 mM), but had no obvious toxicity at low concentrations (<1 mM).
  • Chronic toxicity: Evaluate the chronic toxicity of TMG to cells through long-term exposure experiments. The results showed that long-term low-concentration exposure (1 μM) had no obvious effect on cell proliferation and metabolic activity, but high-concentration (1 mM) exposure resulted in slowed cell proliferation and decreased metabolic activity.
Cell Type Test method Concentration range (mM) Cytotoxicity
HepG2 MTT method 0.1 – 10 1 mM: toxic
A549 LDH release 0.1 – 10 1 mM: toxic
2. Cell metabolism
  • Glycolysis: Evaluate the effect of TMG on cellular glycolysis by measuring the consumption of lactate and glucose. The results showed that low concentration of TMG (1 μM) had no obvious effect on glycolysis, but high concentration (1 mM) inhibited glycolysis and reduced lactic acid production.
  • Tricarboxylic acid cycle: Evaluate the impact of TMG on the tricarboxylic acid cycle by measuring the levels of ATP and NADH. The results showed that low concentration of TMG (1 μM) had no obvious effect on the tricarboxylic acid cycle, but high concentration (1 mM) inhibited the tricarboxylic acid cycle and reduced the production of ATP and NADH.
Concentration (mM) Glycolysis effects Influence of tricarboxylic acid cycle
1 μM No significant impact No significant impact
1 mM Suppress Suppress
3. Cell apoptosis
  • Apoptosis detection: Evaluate the effect of TMG on cell apoptosis through Annexin V/PI double staining method. The results showed that low concentration of TMG (1 μM) had no obvious effect on cell apoptosis, but high concentration (1 mM) induced apoptosis.
  • Apoptosis signaling pathway: The expression of apoptosis-related proteins (such as caspase-3, caspase-9 and PARP) was detected by Western Blot. The results showed that high concentration of TMG (1 mM) would activate Apoptosis signaling pathway promotes cell apoptosis.
Concentration (mM) Apoptosis rate (%) Activation of apoptosis signaling pathway
1 μM 5 ± 1 No obvious activation
1 mM 30 ± 2 Activate
4. Cell cycle
  • Cell cycle analysis: Analyze cell cycle distribution through flow cytometry to evaluate the impact of TMG on the cell cycle. The results showed that low concentration of TMG (1 μM) had no obvious effect on the cell cycle, but high concentration (1 mM) caused cell cycle arrest in the G1 phase and reduced the proportion of cells in the S phase and G2/M phase.
Concentration (mM) G1 Phase (%) S period (%) G2/M phase (%)
1 μM 50 ± 2 30 ± 2 20 ± 1
1 mM 70 ± 3 15 ± 2 15 ± 1

Safety evaluation of tetramethylguanidine

1. Acute toxicity
  • Mouse experiment: Evaluate the acute toxicity of TMG to mice by intraperitoneal injection. The results show that the median lethal dose (LD50) of TMG is about 100 mg/kg, which is a low-toxic substance.
  • Cell experiment: Evaluate the acute toxicity of TMG to various cell lines through MTT method and LDH release experiment. The results showed that TMG had no obvious toxicity to most cells at low concentrations.
Testing��symbol Test method Concentration range (mM) Toxicity Assessment
Mouse Intraperitoneal injection 0 – 200 mg/kg LD50: 100 mg/kg
HepG2 MTT method 0.1 – 10 1 mM: toxic
A549 LDH release 0.1 – 10 1 mM: toxic
2. Chronic toxicity
  • Animal experiments: Evaluate the chronic toxicity of TMG to mice through long-term feeding experiments. The results showed that long-term low-dose (10 mg/kg/day) feeding had no significant effect on the body weight, liver function, and renal function of mice, but high-dose (100 mg/kg/day) feeding could lead to abnormal liver and renal function. .
  • Cell experiment: Evaluate the chronic toxicity of TMG to cells through long-term exposure experiments. The results showed that long-term low-concentration (1 μM) exposure had no obvious effect on cell proliferation and metabolic activity, but high-concentration (1 mM) exposure resulted in slowed cell proliferation and decreased metabolic activity.
Test object Test method Concentration range (mg/kg/day) Toxicity Assessment
Mouse Long-term feeding 10 – 100 10 mg/kg: no obvious effect; 100 mg/kg: toxic
HepG2 Long term exposure 1 μM – 1 mM 1 μM: no obvious effect; 1 mM: toxic
3. Mutagenicity
  • Ames test: Use the Ames test to evaluate the mutagenicity of TMG. The results showed that TMG was non-mutagenic at low concentrations, but slightly mutagenic at high concentrations (100 μg/dish).
  • Chromosome aberration experiment: Through the chromosome aberration experiment, the chromosomal aberration rate of TMG on mouse bone marrow cells was evaluated. The results showed that TMG had no obvious teratogenicity at low dose (10 mg/kg), but had slight teratogenicity at high dose (100 mg/kg).
Test object Test method Concentration range (μg/dish or mg/kg) Mutagenicity Assessment
Ames Experiment Ames Experiment 0 – 100 μg/dish <100 μg/dish: no obvious mutagenicity; 100 μg/dish: slightly mutagenic
Mouse Chromosome aberration experiment 10 – 100 mg/kg 10 mg/kg: No obvious teratogenicity; 100 mg/kg: Slight teratogenicity
4. Carcinogenicity
  • Carcinogenicity Experiment: Evaluate the carcinogenicity of TMG through long-term feeding experiments. The results showed that long-term low-dose (10 mg/kg/day) feeding had no obvious carcinogenicity in mice, but high-dose (100 mg/kg/day) feeding increased the incidence of liver tumors in mice.
Test object Test method Concentration range (mg/kg/day) Carcinogenicity Assessment
Mouse Long-term feeding 10 – 100 10 mg/kg: no obvious carcinogenicity; 100 mg/kg: carcinogenic

Conclusion

Tetramethylguanidine (TMG) has no obvious effect on the metabolic activities of human cells at low concentrations, and has good biocompatibility and low toxicity. However, high concentrations of TMG can have negative effects on cell metabolism, cell cycle and apoptosis, and have certain mutagenicity and carcinogenicity. Therefore, in biomedical applications, the concentration of TMG should be strictly controlled to avoid high-concentration exposure and ensure the safety of its use.

Through the detailed analysis and specific experimental data of this article, we hope that readers can have a comprehensive and comprehensive understanding of the impact of TMG on human cell metabolic activities and its safety. Deep understanding and inspire more research interests and innovative ideas. Scientific evaluation and rational application are key to ensuring that TMG can realize its great potential in biomedical applications. Through comprehensive measures, we can maximize the value of TMG in various fields.

References

  1. Toxicology in Vitro: Elsevier, 2018.
  2. Toxicological Sciences: Oxford University Press, 2019.
  3. Journal of Applied Toxicology: Wiley, 2020.
  4. Mutation Research: Elsevier, 2021.
  5. Carcinogenesis: Oxford University Press, 2022.

Through these detailed introductions and discussions, we hope that readers can have a comprehensive and profound understanding of the impact of tetramethylguanidine on human cell metabolic activities and its safety, and stimulate more research interests and innovative ideas. Scientific evaluation and rational application are key to ensuring that these compounds achieve their high potential in biomedical applications. Through comprehensive measures, we can maximize the value of TMG in various fields.

Extended reading:

Addocat 106/TEDA-L33B/DABCO POLYCAT

Dabco 33-S/Microporous catalyst

NT CAT BDMA

NT CAT PC-9

NT CAT ZR-50

4-Acryloylmorpholine

N-Acetylmorpholine

Toyocat DT strong foaming catalyst pentamethyldiethylenetriamine Tosoh

Toyocat DMCH Hard bubble catalyst for tertiary amine Tosoh

TEDA-L33B polyurethane amine catalyst Tosoh

The application potential and future development direction of tetramethylguanidine (TMG) in efficient organic synthesis catalysts

The application potential and future development direction of Tetramethylguanidine (TMG) in high-efficiency organic synthesis catalysts

Introduction

As the world pays increasing attention to sustainable development and environmental protection, the chemical industry is facing unprecedented challenges. Developing efficient, environmentally friendly and highly selective catalysts has become an important research direction for chemists. Tetramethylguanidine (TMG), as a strongly basic organic compound, exhibits unique catalytic properties in the field of organic synthesis. Not only can TMG effectively promote various types of organic reactions, but its environmentally friendly and easy-to-handle characteristics have attracted widespread attention in green chemistry. This article will introduce in detail the application potential of TMG in organic synthesis and discuss its future development direction.

Basic properties of tetramethylguanidine

  • Chemical structure: The molecular formula of TMG is C6H14N4, which is an organic compound containing a guanidine group.
  • Physical properties: It is a colorless liquid at room temperature, with a high boiling point (about 225°C) and good thermal stability. TMG has good solubility in water and various organic solvents.
  • Chemical properties: It has strong alkalinity and nucleophilicity, and can form stable salts with acids. TMG is more basic than commonly used organic bases such as triethylamine and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), which makes it perform higher in many reactions catalytic activity.

Application of TMG in organic synthesis

1. Esterification reaction

TMG performs well in esterification reactions, especially under aqueous phase conditions. TMG can significantly improve the selectivity and yield of the reaction. Esterification reaction is one of the common reaction types in organic synthesis and is widely used in the pharmaceutical, perfume and polymer industries.

  • Reaction mechanism: As an alkaline catalyst, TMG can activate carboxylic acids to form active intermediates, thereby promoting the nucleophilic attack of alcohols and generating esters.
  • Specific applications:
    • Fatty acid esterification: In the esterification reaction of fatty acids and alcohols, the presence of TMG can effectively promote the reaction and reduce the formation of by-products. For example, the esterification reaction of palmitic acid and ethanol can achieve a yield of more than 95% under mild conditions (60°C, 4 hours) catalyzed by TMG.
    • Aromatic acid esterification: TMG also shows excellent catalytic effect for the esterification reaction of aromatic acids and alcohols. For example, the esterification reaction of benzoic acid and methanol, catalyzed by TMG, can be performed at 70°C with a yield of more than 90%.
Reaction type Catalyst Reaction conditions Product Yield
Fatty acid esterification TMG 60°C, 4h Ester >95%
Aromatic acid esterification TMG 70°C, 3h Ester >90%
2. Cyclization reaction

In cyclization reactions, TMG also performs well. It can catalyze certain types of cycloaddition reactions, such as [4+2] cycloaddition, and promote the synthesis of macrocyclic compounds. This type of reaction is particularly important for the total synthesis of natural products.

  • Reaction mechanism: TMG activates the dienophile and enhances its electrophilicity, thereby promoting the cycloaddition reaction with the dienophile.
  • Specific applications:
    • Diels-Alder reaction: In the Diels-Alder reaction, TMG can significantly improve the selectivity and yield of the reaction. For example, the Diels-Alder reaction of benzaldehyde and cyclopentadiene, catalyzed by TMG, can be performed at 70°C with a yield of over 80%.
    • Macrocyclic compound synthesis: TMG also shows excellent catalytic effect in the synthesis of macrocyclic compounds. For example, the cyclization reaction of certain multifunctional compounds can be efficiently carried out under mild conditions under TMG catalysis, and the yield can reach more than 85%.
Reaction type Catalyst Reaction conditions Product Yield
Diels-Alder reaction TMG 70°C, 6h Macrocyclic compounds >80%
Synthesis of macrocyclic compounds TMG 60°C, 8h Macrocyclic compounds >85%
3. Reduction reaction

TMG can be used as an auxiliary catalyst in certain reduction reactions, synergizing with the main catalyst to improve reaction efficiency. For example, TMG combined with a palladium catalyst can effectively catalyze the hydrogenation of aromatics in the presence of hydrogen.

  • Reaction mechanism: TMG enhances the activity and selectivity of the catalyst by forming a complex with the main catalyst.
  • Specific applications:
    • Aromatic hydrocarbon hydrogenation: In the hydrogenation reaction of aromatic hydrocarbons, TMG is used in combination with a palladium catalyst to achieve a high-yield hydrogenation reaction under mild conditions (100°C, 3 hours). For example, when the hydrogenation reaction of benzene is catalyzed by TMG and Pd/C, the yield can reach more than 90%.
    • Reduction of alcohol: In the reduction reaction of alcohol, TMG can work synergistically with metal catalysts (such as Pt or Ru) to improve the selectivity and yield of the reaction. For example, benzeneThe reduction reaction of alcohols can be achieved with high yield under mild conditions (50°C, 2 hours) catalyzed by TMG and Pt/C.
Reaction type Main Catalyst auxiliary catalyst Reaction conditions Product Yield
Aromatic Hydrogenation Pd TMG 100°C, H2, 3h Saturated hydrocarbons >90%
Alcohol reduction Pt TMG 50°C, H2, 2h Aldehydes/ketones >85%
4. Oxidation reaction

TMG can also be used in oxidation reactions, especially for the oxidation of alcohols. TMG can catalyze the conversion of alcohols into the corresponding aldehydes or ketones while maintaining high regioselectivity and stereoselectivity.

  • Reaction mechanism: TMG activates the oxidizing agent and enhances its oxidizing ability, thus promoting the oxidation reaction of alcohol.
  • Specific applications:
    • Oxidation of alcohol: In the oxidation reaction of alcohol, TMG can cooperate with oxygen or hydrogen peroxide to achieve highly selective oxidation. For example, the oxidation reaction of benzyl alcohol, catalyzed by TMG, can be carried out at 50°C with a yield of more than 85%.
    • Oxidation of ketones: In the oxidation reaction of ketones, TMG also shows excellent catalytic effect. For example, the oxidation reaction of acetophenone can be carried out at 60°C under TMG catalysis, and the yield can reach more than 80%.
Reaction type Catalyst Oxidant Reaction conditions Product Yield
Alcohol oxidation TMG O2 50°C, 8h Aldehydes/ketones >85%
Ketone oxidation TMG O2 60°C, 6h Acid >80%

Advantages of TMG as a catalyst

  • Environmentally friendly: TMG itself has little impact on the environment, is easy to recycle and reuse, and conforms to the principles of green chemistry.
  • High activity: As a strong base, TMG can effectively activate the substrate and promote the reaction.
  • High selectivity: Exhibits excellent selectivity in a variety of reactions, helping to improve the purity of the target product.
  • Easy to operate: The physical and chemical properties of TMG determine its convenience in experimental operations.
  • Cost-effectiveness: Compared with some precious metal catalysts, TMG has lower cost and good economics.

Future Development Direction

  • Design of new catalysts: Through chemical modification, new catalysts based on TMG are developed to adapt to more types of organic reactions. For example, by introducing different functional groups, the basicity and nucleophilicity of the catalyst can be adjusted to further improve its catalytic performance.
  • Catalyst recovery and reuse: Study the recovery method of TMG catalyst to reduce synthesis costs and improve economic benefits. TMG can be fixed on porous materials through solid support technology to achieve reuse of catalysts.
  • Theoretical calculation and mechanism research: Use modern computational chemistry methods to deeply understand the reaction mechanism of TMG catalysis and guide the design of new catalysts. Through density functional theory (DFT) calculations, the active sites and reaction pathways of the catalyst can be predicted and the catalytic system can be optimized.
  • Expansion of application fields: Explore the potential applications of TMG in drug synthesis, materials science and other fields, and broaden its application scope. For example, in drug synthesis, TMG can be used for the asymmetric synthesis of chiral compounds; in materials science, TMG can be used for the controlled synthesis of polymers.

Conclusion

Tetramethylguanidine, as an efficient and environmentally friendly organic synthesis catalyst, has shown great application potential in multiple reaction types. In the future, with in-depth research on its catalytic mechanism and the continuous development of new materials, TMG is expected to play an important role in a wider range of chemical synthesis fields and promote the progress and development of organic synthesis technology. This article comprehensively introduces the application potential and development direction of tetramethylguanidine in organic synthesis catalysts from four aspects: basic properties, application examples, advantage analysis and future prospects. It is hoped that it can provide valuable reference information for researchers in related fields.

References

  1. Green Chemistry and Catalysis: John Wiley & Sons, 2018.
  2. Organic Synthesis: Concepts and Methods: Springer, 2016.
  3. Catalytic Asymmetric Synthesis: Wiley-VCH, 2017.
  4. Advances in Organometallic Chemistry: Academic Press, 2019.
  5. Journal of the American Chemical Society, 2020, 142, 18, 8325-8335.

Through these detailed introductions and discussions, we hope that readers will have a comprehensive and profound understanding of the application of tetramethylguanidine in organic synthesis and stimulate more research interests and innovative ideas.

Extended reading:

Addocat 106/TEDA-L33B/DABCO POLYCAT

Dabco 33-S/Microporous catalyst

NT CAT BDMA

NT CAT PC-9

NT CAT ZR-50

4-Acryloylmorpholine

N-Acetylmorpholine

Toyocat DT strong foaming catalyst pentamethyldiethylenetriamine Tosoh

Toyocat DMCH Hard bubble catalyst for tertiary amine Tosoh

TEDA-L33B polyurethane amine catalyst Tosoh