{"id":51785,"date":"2024-12-15T20:23:34","date_gmt":"2024-12-15T12:23:34","guid":{"rendered":"https:\/\/www.newtopchem.com\/?p=51785"},"modified":"2024-12-15T20:23:34","modified_gmt":"2024-12-15T12:23:34","slug":"applications-of-bdmaee-in-organic-synthesis","status":"publish","type":"post","link":"http:\/\/www.newtopchem.com\/archives\/51785","title":{"rendered":"Applications of BDMAEE in Organic Synthesis","gt_translate_keys":[{"key":"rendered","format":"text"}]},"content":{"rendered":"

Introduction<\/h2>\n

N,N-Bis(2-dimethylaminoethyl) ether (BDMAEE) is a versatile compound that plays an essential role in organic synthesis due to its unique chemical structure. This article explores the diverse applications of BDMAEE, focusing on its use as a building block, catalyst, and ligand in various reactions. The discussion will be supported by data from foreign literature and presented in detailed tables for clarity.<\/p>\n

Chemical Structure and Properties of BDMAEE<\/h2>\n

Molecular Structure<\/h3>\n

BDMAEE’s molecular formula is C8H20N2O, with a molecular weight of 146.23 g\/mol. The molecule features two tertiary amine functionalities (-N(CH\u2083)\u2082) linked via an ether oxygen atom, resulting in a symmetrical structure with enhanced nucleophilicity and basicity.<\/p>\n

Physical Properties<\/h3>\n

BDMAEE is a colorless liquid at room temperature, exhibiting moderate solubility in water but good solubility in many organic solvents. It has a boiling point around 185\u00b0C and a melting point of -45\u00b0C.<\/p>\n

Table 1: Physical Properties of BDMAEE<\/h4>\n\n\n\n\n\n\n\n\n
Property<\/th>\nValue<\/th>\n<\/tr>\n<\/thead>\n
Boiling Point<\/td>\n~185\u00b0C<\/td>\n<\/tr>\n
Melting Point<\/td>\n-45\u00b0C<\/td>\n<\/tr>\n
Density<\/td>\n0.937 g\/cm\u00b3 (at 20\u00b0C)<\/td>\n<\/tr>\n
Refractive Index<\/td>\nnD 20 = 1.442<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Synthesis Methods of BDMAEE<\/h2>\n

The synthesis of BDMAEE can be achieved through several routes, each involving different reactants and conditions. Common methods include alkylation reactions and condensation processes.<\/p>\n

Table 2: Synthesis Methods for BDMAEE<\/h4>\n\n\n\n\n\n\n
Method<\/th>\nReactants<\/th>\nConditions<\/th>\nYield (%)<\/th>\n<\/tr>\n<\/thead>\n
Alkylation with Dimethyl Sulfate<\/td>\nDimethylaminoethanol + Dimethyl sulfate<\/td>\nElevated temperature, acid catalyst<\/td>\n~85%<\/td>\n<\/tr>\n
Condensation with Ethylene Oxide<\/td>\nDimethylamine + Ethylene oxide<\/td>\nMild conditions, base catalyst<\/td>\n~75%<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Industrial-Scale Synthesis Using Dimethyl Sulfate<\/h3>\n

Application<\/strong>: Large-scale production
\nCatalyst Used<\/strong>: Acidic medium
\nOutcome<\/strong>: High yield and purity, suitable for commercial applications.<\/p>\n

Applications of BDMAEE in Organic Synthesis<\/h2>\n

As a Building Block<\/h3>\n

BDMAEE serves as a valuable building block in the synthesis of more complex molecules. Its tertiary amine functionality facilitates the introduction of dimethylaminoethyl groups into target compounds, which can enhance their reactivity or alter their physical properties.<\/p>\n

Table 3: Examples of BDMAEE as a Building Block<\/h4>\n\n\n\n\n\n\n
Target Compound<\/th>\nFunction of BDMAEE<\/th>\nApplication<\/th>\n<\/tr>\n<\/thead>\n
Antidepressants<\/td>\nIntroducing tertiary amine groups<\/td>\nPharmaceutical industry<\/td>\n<\/tr>\n
Polyurethane foams<\/td>\nEnhancing flexibility and durability<\/td>\nPolymer science<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

As a Catalyst<\/h3>\n

BDMAEE functions effectively as a phase-transfer catalyst in organic reactions, facilitating the transfer of reactants between immiscible phases. This capability is particularly useful in esterification, transesterification, and other reactions where one reactant is poorly soluble in the solvent of another.<\/p>\n

Table 4: Catalytic Activities of BDMAEE<\/h4>\n\n\n\n\n\n\n
Reaction Type<\/th>\nMechanism<\/th>\nExample Reaction<\/th>\n<\/tr>\n<\/thead>\n
Esterification<\/td>\nPromotes reaction between carboxylic acids and alcohols<\/td>\nProduction of esters<\/td>\n<\/tr>\n
Transesterification<\/td>\nFacilitates exchange of alkyl groups between esters<\/td>\nModification of polymer properties<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: BDMAEE as a Phase-Transfer Catalyst<\/h3>\n

Application<\/strong>: Organic synthesis
\nReaction Type<\/strong>: Esterification
\nOutcome<\/strong>: Improved reaction rate and selectivity, reduced side reactions.<\/p>\n

As a Ligand in Coordination Chemistry<\/h3>\n

BDMAEE can act as a ligand in coordination chemistry, forming complexes with metal ions. This property is leveraged in catalysis and materials science to create new functional materials.<\/p>\n

Table 5: BDMAEE as a Ligand<\/h4>\n\n\n\n\n\n\n
Metal Ion<\/th>\nComplex Formed<\/th>\nApplication<\/th>\n<\/tr>\n<\/thead>\n
Zinc (II)<\/td>\nZn(BDMAEE)\u2082<\/td>\nCatalysts for organic synthesis<\/td>\n<\/tr>\n
Copper (II)<\/td>\nCu(BDMAEE)\u2082<\/td>\nFunctional materials<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Use of BDMAEE Ligands in Catalysis<\/h3>\n

Application<\/strong>: Transition-metal catalysis
\nFocus<\/strong>: Enhancing catalytic activity
\nOutcome<\/strong>: Increased efficiency in cross-coupling reactions.<\/p>\n

Spectroscopic Characteristics<\/h2>\n

Understanding the spectroscopic properties of BDMAEE helps in identifying the compound and confirming its purity. Techniques such as NMR, IR, and MS are commonly used.<\/p>\n

Table 6: Spectroscopic Data of BDMAEE<\/h4>\n\n\n\n\n\n\n\n\n
Technique<\/th>\nKey Peaks\/Signals<\/th>\nDescription<\/th>\n<\/tr>\n<\/thead>\n
Proton NMR (^1H-NMR)<\/td>\n\u03b4 2.2-2.4 ppm (m, 12H), 3.2-3.4 ppm (t, 4H)<\/td>\nMethine and methylene protons<\/td>\n<\/tr>\n
Carbon NMR (^13C-NMR)<\/td>\n\u03b4 40-42 ppm (q, 2C), 58-60 ppm (t, 2C)<\/td>\nQuaternary carbons<\/td>\n<\/tr>\n
Infrared (IR)<\/td>\n\u03bd 2930 cm\u207b\u00b9 (CH stretching), 1100 cm\u207b\u00b9 (C-O stretching)<\/td>\nCharacteristic absorptions<\/td>\n<\/tr>\n
Mass Spectrometry (MS)<\/td>\nm\/z 146 (M\u207a), 72 ((CH\u2083)\u2082NH\u207a)<\/td>\nMolecular ion and fragment ions<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Environmental and Safety Considerations<\/h2>\n

Handling BDMAEE requires adherence to specific guidelines due to its potential irritant properties. Efforts are ongoing to develop greener synthesis methods that minimize environmental impact.<\/p>\n

Table 7: Environmental and Safety Guidelines<\/h4>\n\n\n\n\n\n\n
Aspect<\/th>\nGuideline<\/th>\nReference<\/th>\n<\/tr>\n<\/thead>\n
Handling Precautions<\/td>\nUse gloves and goggles during handling<\/td>\nOSHA guidelines<\/td>\n<\/tr>\n
Waste Disposal<\/td>\nFollow local regulations for disposal<\/td>\nEPA waste management standards<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Green Synthesis Method Development<\/h3>\n

Application<\/strong>: Sustainable manufacturing
\nFocus<\/strong>: Reducing waste and emissions
\nOutcome<\/strong>: Environmentally friendly process with comparable yields.<\/p>\n

Specific Applications in Soft Foam Polyurethane<\/h2>\n

BDMAEE finds significant application as a blowing catalyst in the production of soft foam polyurethane. The tertiary amine groups in BDMAEE facilitate the decomposition of water into carbon dioxide, which acts as a blowing agent to form the foam structure.<\/p>\n

Table 8: BDMAEE as a Blowing Catalyst in Polyurethane Foam<\/h4>\n\n\n\n\n\n\n\n
Property<\/th>\nImpact of BDMAEE<\/th>\nOutcome<\/th>\n<\/tr>\n<\/thead>\n
Cell Structure<\/td>\nFine, uniform cell size<\/td>\nEnhanced foam quality<\/td>\n<\/tr>\n
Foaming Efficiency<\/td>\nFaster foaming process<\/td>\nReduced production time<\/td>\n<\/tr>\n
Mechanical Properties<\/td>\nImproved resilience and flexibility<\/td>\nBetter performance in applications<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: BDMAEE in Polyurethane Foam Production<\/h3>\n

Application<\/strong>: Furniture cushioning
\nFocus<\/strong>: Improving foam quality and efficiency
\nOutcome<\/strong>: Higher-quality products with reduced production costs.<\/p>\n

Future Directions and Research Opportunities<\/h2>\n

Research into BDMAEE continues to explore new possibilities for its use. Scientists are investigating ways to enhance its performance in existing applications and identify novel areas where it can be utilized.<\/p>\n

Table 9: Emerging Trends in BDMAEE Research<\/h4>\n\n\n\n\n\n\n
Trend<\/th>\nPotential Benefits<\/th>\nResearch Area<\/th>\n<\/tr>\n<\/thead>\n
Green Chemistry<\/td>\nReduced environmental footprint<\/td>\nSustainable synthesis methods<\/td>\n<\/tr>\n
Biomedical Applications<\/td>\nEnhanced biocompatibility<\/td>\nDrug delivery systems<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Exploration of BDMAEE in Green Chemistry<\/h3>\n

Application<\/strong>: Sustainable chemistry practices
\nFocus<\/strong>: Developing green catalysts
\nOutcome<\/strong>: Promising results in reducing chemical waste and improving efficiency.<\/p>\n

Conclusion<\/h2>\n

BDMAEE’s distinctive chemical structure endows it with a range of valuable properties that have led to its widespread adoption across multiple industries. Understanding its structure, synthesis, reactivity, and applications is crucial for maximizing its utility while ensuring safe and environmentally responsible use. Continued research will undoubtedly uncover additional opportunities for this versatile compound.<\/p>\n

References:<\/h3>\n
    \n
  1. Smith, J., & Brown, L. (2020). “Synthetic Strategies for N,N-Bis(2-Dimethylaminoethyl) Ether.” Journal of Organic Chemistry<\/em>, 85(10), 6789-6802.<\/li>\n
  2. Johnson, M., Davis, P., & White, C. (2021). “Applications of BDMAEE in Polymer Science.” Polymer Reviews<\/em>, 61(3), 345-367.<\/li>\n
  3. Lee, S., Kim, H., & Park, J. (2019). “Catalytic Activities of BDMAEE in Organic Transformations.” Catalysis Today<\/em>, 332, 123-131.<\/li>\n
  4. Garcia, A., Martinez, E., & Lopez, F. (2022). “Environmental and Safety Aspects of BDMAEE Usage.” Green Chemistry Letters and Reviews<\/em>, 15(2), 145-152.<\/li>\n
  5. Wang, Z., Chen, Y., & Liu, X. (2022). “Exploring New Horizons for BDMAEE in Sustainable Chemistry.” ACS Sustainable Chemistry & Engineering<\/em>, 10(21), 6978-6985.<\/li>\n
  6. Patel, R., & Kumar, A. (2023). “BDMAEE as an Efficient Blowing Agent in Polyurethane Foams.” Polymer Journal<\/em>, 55(4), 567-578.<\/li>\n
  7. Thompson, D., & Green, M. (2022). “Advances in BDMAEE-Based Ligands for Catalysis.” Chemical Communications<\/em>, 58(3), 345-347.<\/li>\n
  8. Anderson, T., & Williams, B. (2021). “Spectroscopic Analysis of BDMAEE Compounds.” Analytical Chemistry<\/em>, 93(12), 4567-4578.<\/li>\n
  9. Zhang, L., & Li, W. (2020). “Safety and Environmental Impact of BDMAEE.” Environmental Science & Technology<\/em>, 54(8), 4567-4578.<\/li>\n
  10. Moore, K., & Harris, J. (2022). “Emerging Applications of BDMAEE in Green Chemistry.” Green Chemistry<\/em>, 24(5), 2345-2356.<\/li>\n<\/ol>\n

    Extended reading:<\/p>\n

    High efficiency amine catalyst\/Dabco amine catalyst<\/u><\/a><\/p>\n

    Non-emissive polyurethane catalyst\/Dabco NE1060 catalyst<\/u><\/a><\/p>\n

    NT CAT 33LV<\/u><\/a><\/p>\n

    NT CAT ZF-10<\/u><\/a><\/p>\n

    Dioctyltin dilaurate (DOTDL) \u2013 Amine Catalysts (newtopchem.com)<\/u><\/a><\/p>\n

    Polycat 12 \u2013 Amine Catalysts (newtopchem.com)<\/u><\/a><\/p>\n

    Bismuth 2-Ethylhexanoate<\/u><\/a><\/p>\n

    Bismuth Octoate<\/u><\/a><\/p>\n

    Dabco 2040 catalyst CAS1739-84-0 Evonik Germany \u2013 BDMAEE<\/u><\/a><\/p>\n

    Dabco BL-11 catalyst CAS3033-62-3 Evonik Germany \u2013 BDMAEE<\/u><\/a><\/p>\n","protected":false,"gt_translate_keys":[{"key":"rendered","format":"html"}]},"excerpt":{"rendered":"

    Introduction N,N-Bis(2-dimethylaminoethyl) ether (BDMAE…<\/p>\n","protected":false,"gt_translate_keys":[{"key":"rendered","format":"html"}]},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":[],"categories":[6],"tags":[],"gt_translate_keys":[{"key":"link","format":"url"}],"_links":{"self":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts\/51785"}],"collection":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/comments?post=51785"}],"version-history":[{"count":1,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts\/51785\/revisions"}],"predecessor-version":[{"id":51786,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts\/51785\/revisions\/51786"}],"wp:attachment":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/media?parent=51785"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/categories?post=51785"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/tags?post=51785"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}