18464-23-8

Basic information

• Product Name: N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium
• Synonyms: N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium;N1,N2-Didodecyl-N1,N1,N2,N2-tetramethylethane-1,2-diaminium bromide
• CAS NO: 18464-23-8
• Molecular Formula: 2Br*C₃₀H₆₆N₂
• Molecular Weight: 0
• Mol File: 18464-23-8.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium(18464-23-8)
• EPA Substance Registry System: N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium(18464-23-8)

Safety Data

• Hazardous Substances Data: 18464-23-8(Hazardous Substances Data)

Usage

Uses

Used in Industrial Cleaning Products:
N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium is used as a cationic surfactant for enhancing the cleaning efficiency of industrial cleaning products. Its ability to lower the surface tension of water allows for better penetration and removal of dirt and grease, making it an effective component in these formulations.
Used in Water Treatment:
In the water treatment industry, N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium is used as a disinfectant agent. Its antimicrobial properties help in controlling the growth of microorganisms, ensuring the safety and quality of water supplies.
Used as a Preservative in Personal Care Products:
N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium is used as a preservative in personal care products to prevent microbial contamination. Its ability to inhibit the growth of bacteria, fungi, and viruses extends the shelf life of these products and ensures their safety for consumer use.
Used in the Synthesis of Other Cationic Surfactants:
N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium is also used as a raw material in the synthesis of other cationic surfactants. Its unique structure allows for the creation of surfactants with specific properties tailored to various applications.
Used in Microemulsions and Emulsion Polymerization Processes:
N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium is used as a component in microemulsions and emulsion polymerization processes. Its cationic nature aids in stabilizing the emulsions and improving the overall performance of these processes.
However, it is important to exercise caution when using N,N'-bis(dodecyldimethyl)-1,2-ethanediammonium, as it can be toxic to aquatic organisms and may cause irritation to the skin and eyes. Proper handling and disposal methods should be followed to minimize potential environmental and health risks.

Upstream product

• 106303-35-9 C₁₈H₄₁N₂⁽¹⁺⁾*Br^(1-) 
• 143-15-7 1-dodecylbromide 
• 74-83-9 methyl bromide 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 

Downstream Products

• 74-83-9 methyl bromide 

Relevant articles and documents

Aggregation and thermodynamic properties of some cationic gemini surfactants

In this study, the gemini surfactants of the alkanediyl-α-ω- bis(alkyl dimethyl ammonium) dibromide type, on the one hand, with different alkyl groups containing m carbon atoms and an ethanediyl spacer, referred to as ''m-2-m'' (m = 10, 12 and 16) and, on

Surface-active properties and antimicrobial study of conventional cationic and synthesized symmetrical gemini surfactants

Symmetrical gemini surfactants of cationic series α,ω- alkanediyl bis (dimethyl ammonium bromide) commonly referred as ''m-s-m'' have been synthesized. Spectral analysis was performed to confirm compound structures and purity. Conductivity and surface tension measurements provide better understanding of the micellization process. Their self-assembly behavior in aqueous solution is also discussed in detail. The antimicrobial efficacy was measured by bacterial and fungal growth inhibition expressed as minimal inhibitory concentration values against five strains of a representative group of microorganisms viz. Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumonia, Salmonella paratyphi B and Aspergillus niger. All of the synthesized surfactants showed antimicrobial activity against them, but at different levels depending on their structures. The surfactants possessing longer alkyl chains (more hydrophobic environment) demonstrated better antimicrobial functionality. The antimicrobial potency was found to be dependent on the representative target microorganism (Gram-positive bacteria > fungi >Gram-negative bacteria), as well as on the ionic nature of the surfactant (cationic), alkyl chain length (m = 12, 16) and spacer length (s = 2, 4, 6) of the synthesized compounds. Gemini surfactants such as 12-2-12 and 12-4-12 were found to be weakly active whereas 16-2- 16 and 16-4-16 compounds proved to be the most potent antimicrobial surface-active agents among the synthesized gemini homologues. AOCS 2011.

Synthesis, molecular structure, spectral properties and antifungal activity of polymethylene-α,ω-bis(n,n-dimethyl-n-dodecyloammonium bromides)

Hexamethylene-1,6-bis-(N,N-dimethyl-N-dodecylammonium bromide) (1), pentamethylene-1,5-bis(N,N-dimethyl-N-dodecylammonium bromide) (2), tetramethylene-1,4-bis(N,N-dimethyl-N-dodecylammonium bromide) (3), trimethylene-1,3-bis(N,N-dimethyl-N-dodecylammonium bromide) (4) and ethylene-1,2-bis(N,N-dimethyl-N-dodecylammonium bromide) (5) have been obtained and characterized by FTIR and NMR spectroscopy. DFT calculations have also been carried out. The optimized bond lengths, bond angles and torsion angles calculated by Hartree-Fock/3-21G(d,p) approach have been presented. MIC values for A. niger, P. chrysogenum, C. albicans have been determined and the relationship between MIC and spacer length has been discussed.

Gemini surfactant electrospun membranes

Our research demonstrates electrospun nonwoven fibrous scaffolds from a low molar mass gemini ammonium surfactant, N,N'-didodecyl-N,N,N',N'-tetramethyl-N, N'-ethanediyldiammonium dibromide (12-2-12). Cryogenic transmission electron microscopy (cryo-TEM) and solution rheological experiments revealed micellar morphological transitions of 12-2-12 in water and watenmethanol (1:1 vol). The microstructure of 12-2-12 in water transitioned from entangled, cylindrical, threadlike micelles to branched threadlike micelles, and a viscoelastic, entangled, highly branched network of threadlike micelles with increasing concentration finally formed. In sharp contrast, the solution behavior of 12-2-12 in watenmethanol produced a drastically different micellar microstructure compared to that in water, and the morphology transitioned from partitioned, globular micelles to overlapped micelles at an overlap concentration (C*) of 11 wt %. Electrospinning 12-2-12 from water did not produce fibers at any concentration; however, electrospinning 122-12 in watenmethanol at concentrations greater than 2C* produced hydrophilic continuous fibers with diameters ranging from 0.9 to 7 μm. High surface area scaffolds with hydrophilic surfaces offer potential as charged controlledrelease membranes, tissue engineering scaffolds, and coatings for biologically compatible devices.

Nonaqueous lyotropic liquid-crystalline phases formed by gemini surfactants in a protic ionic liquid

The aggregation behaviors of three Gemini surfactants [(CsH 2s-α,ω-(Me2N+CmH 2m+1Br-)2, s = 2, m = 10, 12, 14] in a protic ionic liquid, ethylammonium nitrate (EAN), have been investigated. The polarized optical microscopy and small-angle X-ray scattering (SAXS) measurements are used to explore the lyotropic liquid crystal (LLC) formation. Compared to the LLCs formed in aqueous environment, the normal hexagonal and lamellar phases disappear. However, with increasing the surfactant concentration, a new reverse hexagonal phase (HII) can be mapped over a large temperature range except for other ordered aggregates including the isotropic solution phase and a two-phase coexistence region. The structural parameters of the HII are calculated from the corresponding SAXS patterns, showing the influence of surfactant amount, alkyl chain length, and temperature. Meanwhile, the rheological profiles indicate a typical Maxwell behavior of the LLC phases formed in EAN.

Micellization studies of dicationic gemini surfactants (m-2-m Type) in the presence of various counter- and Co-ions

Salts have the ability to influence the water activity and self-association of ionic micelles. In the present case, gemini surfactants; ethanediyl-α,ω-bis(dimethyl alkyl ammonium bromide) (referred to as m-2-m, m = 10, 12, 14) are synthesized and their micellization study in aqueous medium in presence of monovalent inorganic (NaBr, NaNO3, NaCl, KCl, LiCl) and organic salts (NaTos, NaBenz, NaSal) at 303 K is systematically investigated by conductometric and tensiometric methods. All the salts have the tendency to lower the critical micelle concentration of the surfactants. The effect of inorganic salts on the micellization properties has been found to obey the Hofmeister series. Organic salts reduce the CMC more effectively as compared to inorganic salts. The theoretical models of Rubingh and Rosen have been used to compare the results and obtain the interaction parameters, minimum area per molecule, surface excess, mixed micelle composition, activity coefficients and free energies of micellization/adsorption.

Phase Transfer Catalysis with Quaternary Ammonium Type Gemini Surfactants: O-Alkylation of Isovanillin

In this paper, O-alkylation of isovanillin with unusual phase transfer catalysts alkandiyl-α,ω-bis(dimethylalkylammonium bromide) dimeric surfactants (also known as gemini surfactants) is described. Some dimeric surfactants with simple hydrophobic alkyl chains and others with hydrophobic alkyl chains containing ester functionalities with different lengths were synthesized and characterized in our laboratory. The alkylation of isovanillin with alkyl halide was successively carried out in the presence of potassium carbonate and a phase transfer catalyst in tetrahydrofuran. The same reactions were also performed with both the traditional phase transfer catalyst tetrabutylammonium bromide and without any catalyst. The results were compared with those of dimeric surfactants. Consequently, it was expressed that alkandiyl-α,ω-bis(dimethylalkylammonium bromide) dimeric surfactants successively exhibit the character of phase transfer catalysts through environmentally friendly procedures under mild conditions. The most significant feature of this work is that dimeric surfactants have been determined to act as phase transfer agents.

Adsorption of cationic gemini surfactants at solid surfaces studied by QCM-D and SPR: Effect of the rigidity of the spacer

Two small series of cationic gemini surfactants with dodecyl tails have been synthesized and evaluated with respect to self-assembly in bulk water and at different solid surfaces. The first series contained a flexible alkane spacer and is denoted 12-n-12,

Tuning the surface activity of gemini amphiphile by the host-guest interaction of cucurbit[7]uril

This research is aimed to develop an effective supramolecular route for tuning the surface activity of the surfactant. To this end, cationic gemini amphiphiles and cucurbit[7]uril (CB[7]) were complexed in water, and each hydrophobic chain of the gemini amphiphiles was bound with a CB[7]. The steric hindrance of CB[7] prevented the two hydrophobic chains from getting closed to each other, leading a significant change of surface activity. Before supramolecular complexation, the surface activity of the gemini amphiphile is relatively high, which can generate the foams easily. However, the foam generated by gemini amphiphile can be destructed by adding CB[7], suggesting that the suface activity is lowed after the supramolecular complexation. The surface activity can recover after adding 1-adamantanamine hydrochloride, which has a stronger ability to bind CB[7]. Therefore, a controllable foaming and defoaming process can be realized. It is highly anticipated that supramolecular chemistry for tuning amphiphilicity of surfactants may find application in the fields that fast foaming and defoaming are needed.

A relative study on the micellization behavior of 12–2–12 Gemini surfactant with lactose and maltodextrin in aqueous medium: Spectroscopic and conductometric analysis

The present work reports the micellization mechanism and physico–chemical properties of synthesized 12–2–12 Gemini surfactant in aqueous solution of carbohydrates (lactose and maltodextrin) (0.0, 0.5, 1.0) % (w/v) at varying temperatures in the range (293.15–313.15) K. For this purpose, conductometric as well as spectroscopic measurements have been engaged to analyze the micellar modulation of Gemini surfactant in terms of its critical micelle concentration (CMC). The carbohydrates (lactose/maltodextrin) have been found to decrease the CMC of 12-2-12 Gemini surfactant, however, the effect is much more pronounced in maltodextrin as compared to lactose which is in compliance with the hydrophobic region present in the molecules. Further, temperature dependence of CMC has been employed to compute thermodynamic parameters of micellization in order to procure a better knowledge about the behavior of surfactant and intermolecular interactions present in such systems. The study of aqueous Gemini–carbohydrate systems may be helpful in working towards a healthier world from both personal as well as environmental aspects of life.