68796-78-1

Basic information

• Product Name: N-tetradecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide
• Synonyms: N-tetradecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide
• CAS NO: 68796-78-1
• Molecular Weight: 366.426
• Mol File: 68796-78-1.mol

Chemical Properties

• CAS DataBase Reference: N-tetradecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: N-tetradecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide(68796-78-1)
• EPA Substance Registry System: N-tetradecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide(68796-78-1)

Safety Data

• Hazardous Substances Data: 68796-78-1(Hazardous Substances Data)

Upstream product

• 14002-21-2 dimethylaminomethanol 
• 112-71-0 1-Bromotetradecane 
• 108-01-0 2-(N,N-dimethylamino)ethanol 

Relevant articles and documents

Synthesis, characterization and conductivity of quaternary nitrogen surfactants modified by the addition of a hydroxymethyl substructure on the head group

Two novel series of hydroxymethyl group-appended quaternary nitrogen surfactants (QNSs) based on the aliphatic N-alkyl-trimethylammonium and aromatic N-alkylpyridinium head groups were synthesized from the appropriate nitrogen head group precursor and 1-bromoalkane. The QNSs were characterized using 1H and 13C nuclear magnetic resonance and infrared spectroscopy, and their purity confirmed using elemental analysis. The solution behavior of the QNSs was investigated by conductivity, assessing both the aggregation concentration as well as the amount of counter-ion dissociation. The results showed a general decrease in the aggregation concentration for the compounds with the hydroxymethyl addition, where the pyridinium compounds were more affected than the ammonium QNSs. In contrast, the extent of counter-ion dissociation (α) from the aggregate was slightly increased for the ammonium compounds but that of the pyridinium compounds was not generally affected by the structural modification.

The Effect of Polar Head and Chain Length on the Physicochemical Properties of Micellization and Adsorption of Amino Alcohol-Based Surfactants

In this work, we have synthesized a series of quaternary ammonium from amino alcohols and n-bromoalkanes. The compounds are referred to as CnEtOH, CnPrOH, and CniPrOH (where n = 12 and 14 carbons, EtOH = ethanol, PrOH = propanol, iPrOH = iso-propanol). Their structures were checked using the usual spectroscopic methods [1H, 13C nuclear magnetic resonance (NMR) and infrared (IR)]. Their physicochemical properties in aqueous solution were studied using conductivity, surface tension, and ultra violet (UV)–visible absorption spectroscopy measurements. This study was conducted to show the effect of the linear hydrophobic chain and the location of the OH polar group with respect to the N+ quaternary ammonium on the physicochemical properties of the surfactants. The comparison between the physicochemical properties of the surfactants studied shows a distinct effect of the position of the OH group on the critical micelle concentration (CMC), the ionization degree (a), the area occupied at the interface (Amin), the free energy of adsorption (ΔG0ad), and the free energy of micellization (ΔG0M). The intermolecular interaction between the synthetic surfactants and the methyl orange (OM) dye is related to the degree of hydration of the micelle, proven by the hypsochromic displacement of OM wavelength (?max) and ionization (a) of the micelles. The CMC, the degree of ionization, and the degree of hydration of the micelle follow the same trend.

Enthalpies of transfer of amino acids from water to aqueous cationic surfactants solutions at 298.15 K

Enthalpies of solution of five amino acids, glycine, l-alanine, l-valine, l-serine, and l-threonine in aqueous solutions of three quarternary ammonium surfactants, [CnH2n+1(CH3)2NCH 2CH2OH]Br (n = 12, 14, 16), (n = 12, 14, 16), have been measured at 298.15 K with a microcalorimeter. Enthalpies of transfer of amino acids from water to aqueous surfactant solutions have been derived. It has been observed that, at relatively low concentrations of the surfactant solutions, amino acids are still in the water phase and mainly interact with the hydrophilic head groups of the surfactant molecules. With an increase of the concentration of the surfactant solutions, the microenvironment of amino acids changes, and the molecules might insert into the micelles and interact with the hydrophobic tail groups of the surfactant molecules. The results are discussed in terms of a delicate balance of hydrophobic and hydrophilic interactions and differences in the molecular structure of amino acids.

Anticorrosive effects and antimicrobial properties of alkyldimethyl(hydroxyalkyl)ammonium bromides

Quaternary ammonium compounds containing the hydroxyalkyl moiety in the head group have been synthesized. These compounds exhibit a micelle-forming ability, high anticorrosive activity, and antimicrobial action. The compounds of the formula R(CH3)2N+(CH2CH 2CH2OH)Br- with R = C14H 29-C18H37 are characterized by a protective effect higher than 90-99% at 10 mg/l with respect to hydrogen sulfide corrosion, inhibiting properties against carbon dioxide corrosion (84-98% at 10-25 mg/l), and bactericidal action on sulfate-reducing bacteria (10-50 mg/l).

Carbamate-bearing surfactants: Micellization, solubilization, and biological activity

Herein novel cationic carbamate-bearing surfactants have been synthesized and characterized as effective building blocks for the development of polyfunctional nanosystems showing solubilizing, antimicrobial and membrane-tropic activity. For this purpose aggregation behavior of the surfactants has been evaluated, with the structure of head group and hydrophobicity varied. Their concentration and temperature ranges of micelle formation have been determined through tensiometry and conductometry: critical micelle concentration, Krafft point and adsorption parameters at the interface have been quantified. Solubilization of hydrophobic probes (Orange OT and pyrene) has been employed to determine aggregation numbers, evaluate solubilization capacity of micelles, and characterize micropolarity in the localization site of the probe. The value of LD50 of the carbamate-bearing surfactants has been determined (mice, intraperitoneal administration). It has been shown that the surfactants can be related to the class of moderately toxic compounds. Investigation of antimicrobial properties of carbamate-bearing surfactants has determined their significant antibacterial and antifungal activity against Staphylococcus aureus, Escherichia coli, Bacillus cereus, Trichophyton mentagrophytes, and Candida albicans.

Critical micellar concentrations of quaternary ammonium surfactants with hydroxyethyl substituents on headgroups determined by isothermal titration calorimetry

The micelle formations in aqueous solutions of a set of quaternary ammonium surfactants, N-alkyl-N-2-hydroxyethyl-N,N-dimethyl ammonium bromide (C nHDAB, n = 12, 14, and 16), N-alkyl-N,N-2-dihydroxyethyl-N-methyl ammonium bromide (CnDHAB, n = 12, 14, and 16), along with N-dodecyl-N,N,N-trimethyl ammonium bromide (DTAB), and N-cetyl-N,N,N-trimethyl ammonium bromide (CTAB), were investigated by the isothermal titration calorimetry (ITC). The critical micellar concentrations (CMCs) and the enthalpies of micellization at six different temperatures were determined. The entropies and Gibbs free energies of micellization were then calculated by using the pseudophase separation model. The effects on the thermodynamic data of the temperature, the length of the alkane chain, and the number of hydroxyethyl substituents on the surfactant headgroup were discussed. The CMC value of each surfactant increases slightly with the temperature increase. At a given temperature, both the increases of the length of the alkane chain and the number of hydroxyethyl substituents lead to the decreases of the CMC values.

Dependence of in vitro enzymic hydrolysis of alkyl(2-benzoyl-oxyethyl)dimethylammonium bromides on the alkyl length

Microsomal esterases were used in (he study of the m vitro enzymic hydrolysis of the ester bond in alkyl(2-benzoyloxyethyl)dimethylammonium bromides. These compounds are potential "soft" disinfectants, easily biodegradable to nontoxic biologically inactive hydrolytic products, namely substituted choline and benzoic acid. Formation of the latter product was used to monitor the kinetics of the reaction. It has been found that the rate of enzymic hydrolysis is substantially influenced by different length of the alkyl chain on the ammonium nitrogen. At the same time, interspecies (rat-mouse) and interorgan (liver-kidney) variability has been observed.

Quaternary ammonium compounds

Quaternary ammonium compounds have the formula R1 R2 R3 N+ (CH2)m Y X- wherein R1 is an alkyl containing 8-20 carbon atoms, R2 is an alkyl containing 8-20 carbon atoms or methyl or ethyl, R3 is methyl or ethyl, m is an integer from 1-6, X is an anion and Y is a group having the structure --Z, --OH, --OR4, --OC(O)R5, --CN, --O--S(O) (O)--OQ, --C(O)OR6, --C=CH, --SR7, --S(O)(O)R8, --S(O)R9, --NR10 R11 and --CH=CH2 wherein R4, R5, R6, R7, R8, R9, R10, R11 are alkyls containing 1-12 carbon atoms or are phenyl and Z is halogen and Q is hydrogen or a cation having been found to be very effective bactericides.

Quaternary ammonium compounds

Quarternary ammonium compounds have the formula R1 R2 R3 N+ (CH2)m Y X- wherein R1 is an alkyl containing 8-20 carbon atoms, R2 is an alkyl containing 8-20