101396-91-2Relevant articles and documents
Synthesis and Properties of Three N-Alkyl Bis-Quaternary Ammonium Salt Surfactants
Liu, Jiajia,Shen, Jun,Wang, Chen,Xu, Hujun
, p. 1017 - 1024 (2020)
Three N-alkyl bis-quaternary ammonium salt surfactants were synthesized by using epichlorohydrin, trimethylamine hydrochloride, and N,N-dimethylalkyl amine as raw materials in a two-step manner. The products were characterized by 1H NMR and MS, confirming the successful synthesis of 2-Hydroxy-N1,N1,N3,N3-tetramethyl-N3-dodecylpropane-1,3-diammonium chloride (HPDDC), 2-Hydroxy-N1,N1,N3,N3-tetramethyl-N3-tetradecylpropane-1,3-diammonium chloride (HPTDC), and 2-Hydroxy-N1, N1, N3, N3-tetramethyl-N3-hexadecylpropane-1,3-diammonium chloride (HPHDC). Moreover, the influence of carbon chain length on surface-active properties, foaming properties, and paraffin liquid emulsion stability was investigated. Results indicated that critical micelle concentrations (cmc) decreased with increasing carbon chain length from 12 to 16, and the cmc and γcmc were lower than those of Dodecyl trimethyl ammonium chloride (DTAC). The products exhibited better foam properties and worse emulsifying performance than those of DTAC. The Krafft points of all products were determined to be below 0 °C. Moreover, the products also demonstrated outstanding antibacterial properties.
Enantiomer separation of rac-2,2′-dihydroxy-1,1′-binaphthyl (BNO) by inclusion complexation with racemic or achiral ammonium salts and a novel transformation of a 1:1:1 racemic complex of BNO, Me4N +·Cl- and MeOH into a conglomerate complex in the solid state
Yoshizawa, Kazuhiro,Toyota, Shinji,Toda, Fumio
, p. 7767 - 7774 (2004)
The complete simultaneous and mutual enantiomer resolution of 2,2′-dihydroxy-1,1′-binaphthyl (BNO) and N-(3-chloro-2- hydroxypropyl)-N,N,N-trimethylammonium chloride, Me3N +CH2CH(OH)CH2Cl·Cl- into their enantiomers by inclusion complexation between their racemates in EtOH in the presence of a chiral seed crystal is reported. The enantiomer resolution of the rac-BNO was also accomplished easily by inclusion complexation with achiral ammonium salts, N-(2-hydroxyethyl)-N,N,N-trimethylammonium chloride, Me 3N+CH2CH2OH·Cl- and tetramethylammonium chloride, Me4N+·Cl -. Inclusion complexation of the rac-BNO with Me3N + CH2CH2OH·Cl- gave only a 1:1 conglomerate inclusion complex but not a racemic complex. Recrystallization of the rac-BNO and an equimolar amount of Me4N+· Cl- from MeOH (7 ml) and MeOH (15 ml) gave a 1:1:1 racemic complex, BNO·Me4N+·Cl-·MeOH and a 1:1 conglomerate complex, BNO·Me4N+·Cl -, respectively. Novel transformation of the former racemate into the latter conglomerate occurred by heating or by exposure to MeOH vapor in the solid state.
Cationic curdlan: Synthesis, characterization and application of quaternary ammonium salts of curdlan
Suflet, Dana M.,Popescu, Irina,Pelin, Irina M.,Nicolescu, Alina,Hitruc, Gabriela
, p. 396 - 405 (2015)
Water-soluble curdlan derivatives containing quaternary ammonium groups with a degree of substitution up to 0.15 were synthesized using different cationic agents in alkaline medium. The chemical structure of curdlan derivatives was confirmed by FTIR, 13C and 1H NMR spectroscopy. The influence of some reaction conditions (temperature, time, and molar ratio) on the degree of substitution and the viscosimetic behaviour were studied. The degree of substitution increased with the amount of the cationization agent per anhydroglucose unit and was higher when the glycidyl reagents were used, compared with the case when the reagents contained chloro-hydroxypropyl groups. The viscosity behaviour of these new derivatives of curdlan in aqueous solutions and the values of intrinsic viscosities calculated using different semi-empirical equations denote a high hydrodynamic dimension of the macromolecular coils. The interaction of these cationic curdlan derivatives with an anionic curdlan (monobasic curdlan phosphate) was studied in situ by turbidimetric measurements and after 24 h by optical density and dynamic light scattering. The formation of polyelectrolyte complexes was influenced by the degree of substitution, the nature of the quaternary substituent, and by the ionic strength of the aqueous solution. The morphology of the polyelectrolyte complexes particles in dry state was examined by atomic force microscopy.
Synthesis and physicochemical properties of low-substituted cationic ethers of starch
Butrim,Butrim,Bil'dyukevich,Yurkshtovich,Kaputskii
, p. 2026 - 2032 (2008)
The kinetics of the formation of cationic starch ethers under the action of 3-chloro-2-hydroxypropyltrimethylammonium chloride is studied in relation to the reactant molar ratio, temperature, and concentration of the starch suspension. Comparative data on
Synthesis, characterization, and antibacterial activity of N,O-quaternary ammonium chitosan
Xu, Tao,Xin, Meihua,Li, Mingchun,Huang, Huili,Zhou, Shengquan,Liu, Juezhao
, p. 2445 - 2450 (2011)
N,N,N-Trimethyl O-(2-hydroxy-3-trimethylammonium propyl) chitosans (TMHTMAPC) with different degrees of O-substitution were synthesized by reacting O-methyl-free N,N,N-trimethyl chitosan (TMC) with 3-chloro-2-hydroxy-propyl trimethyl ammonium chloride (CHPTMAC). The products were characterized by 1H NMR, FTIR and TGA, and investigated for antibacterial activity against Staphylococcus aureus and Escherichia coli under weakly acidic (pH 5.5) and weakly basic (pH 7.2) conditions. TMHTMAPC exhibited enhanced antibacterial activity compared with TMC, and the activity of TMHTMAPC increased with an increase in the degree of substitution. Divalent cations (Ba2+ and Ca2+) strongly reduced the antibacterial activity of chitosan, O-carboxymethyl chitosan and N,N,N-trimethyl-O-carboxymethyl chitosan, but the repression on the antibacterial activity of TMC and TMHTMAPC was weaker. This indicates that the free amino group on chitosan backbone is the main functional group interacting with divalent cations. The existence of 100 mM Na+ slightly reduced the antibacterial activity of both chitosan and its derivatives.
Synthetic method of biquaternary ammonium salt intermediate
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Paragraph 0015-0024, (2020/10/14)
The invention provides a synthetic method of a biquaternary ammonium salt intermediate. The synthetic method comprises the following step: in a water phase, reacting 1,3-dichloropropanol with trimethylamine at a low temperature to generate the biquaternary ammonium salt intermediate 3-chloro-2-hydroxypropyl trimethyl ammonium chloride. According to the invention, 1,3-dichloropropanol is used as aconnecting group, and the industrial chain and application of 1,3-dichloropropanol are expanded based on a 1,3-dichloropropanol production line; the reaction is performed in a water phase, so the useof an organic solvent is avoided, and safety and environmental protection are realized; and the method adopts a low-temperature reaction, and is safe and energy-saving.
Synthetic method of asymmetric bisquaternary ammonium salt bactericide
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Paragraph 0012; 0013; 0016, (2018/12/12)
The invention provides a synthetic method of asymmetric bisquaternary ammonium salt bactericide. The synthetic method comprises the specific steps of using water as a reaction solvent, putting a trimethylamine hydrochloride aqueous solution in a kettle, under the stirring condition, dropwise adding epichlorohydrin, controlling the temperature of a system to be 30-40 DEG C, wherein the molar ratioof trimethylamine hydrochloride to the epichlorohydrin is 1 to (0.8-1.2), and performing a reaction for 1-2 hours so as to obtain an intermediate product namely N-(3-chloro-2-hydroxypropyl)-N,N,N-trimethylammonium chloride; and then raising the temperature to be 80-100 DEG C, adding long chain alkyl tertiary amine to the reaction system at a time, wherein the molar ratio of the long chain alkyl tertiary amine to the trimethylamine hydrochloride is 1 to (1.0-1.5), performing a reaction under the condition of the pressure being 0.1-0.5Mpa for 4-10 hours, and performing synthesis so as to obtainthe asymmetric bisquaternary ammonium salt bactericide of which the molecular structural formula (I) is as shown in the description. The yield of the product namely the asymmetric bisquaternary ammonium salt bactericide can reach 90%, the reaction rate is high, the preparation process is safe and environmentally friendly, large-scale industrial production is easy to realize, and the bacteriocidalproperties of the product can be better than those of a traditional bactericide. (As shown in the description).
Preparation method of levocarnitine
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Paragraph 0026; 0027; 0028; 0029, (2017/08/29)
The invention provides a preparation method of levocarnitine. The preparation method comprises the following steps: taking epoxy chloropropane as a starting material, then carrying out amination, cyaniding and carrying out ester exchange under the action of lipase CALB to obtain corresponding chiral ester, then carrying out alkaline hydrolysis and acidification, and then removing chlorine ions under the action of strongly alkaline resin, so that the levocarnitine finished product is obtained. In the invention, acid resin is used in an ester exchange process, and recemization can be realized, so that yield and optical purity of the levocarnitine are improved.
PREPARATION METHOD OF HIGH-PURITY L-CARNITINE
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Page/Page column 4-5, (2011/11/06)
The present invention relate to a preparation method of high-purity L-carnitine which belongs to an important technique of quality control in different steps of chiral medicine production. The method comprises the following steps of: monitoring the content of the L-isomer impurity in chiral material S-epichlorohydrin by gas chromatography and chiral column and controlling the content of the L-isomer impurity in chiral raw material in the definite range; monitoring and controlling the specific optical rotation of the chiral intermediate L-3-chloro-2-hydroxy-N,N,N-trimethyl-propanaminium in the definite ranges using a polarimeter; monitoring the content of the R-isomer in the intermediate L-3-cyano-2-hydroxy-N,N,N-trimethyl-propanaminium using derivation agent (+)α-methyl-6-methoxy-2-naphthaleneaceyl chloride by HPLC and controlling the content of the isomer in the intermediate in the definite range; and measuring the final product L-carnitine using derviation agent (+)α-methyl-6-methoxy-2-naphthaleneaceyl chloride by HPLC. This method gives the high-purity L-carnitine in which the content of L-isomer may be more than 97% and that of R-isomerless than 2%.
A PREPARATION METHOD OF HIGH-PURITY L-CARNITINE
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Page/Page column 8, (2011/09/15)
The present invention relate to a preparation method of high-purity L-carnitine which belongs to an important technique of qulity control in different steps of chiral medicine production. The method comprises the following steps of :monitoring the content of the L-isomer impurity in chiral material S-epichlorohydrin by gas chromatography and chiral cilumn and controlling the content of the L-isomer impurity in chiral raw material in the definite range; monitoring and controlling the specific optical rotation of the chiral intermediate L-3-chloro-2-hydroxy-N,N,N-trimethyl-propanaminium in the definite ranges using a polarimeter; monitoring the content of the R-isomer in the intermediate L-3-cyano-2-hydroxy-N,N,N-trimethyl-propanaminium using derivation agent (+)α-methyl-6-methoxy-2-naphthaleneaceyl chloride by HPLC and controlling the content of the isomer in the intermediate in the definite range; and measuring the final product L-carnitine using derviation agent (+)α-methyl-6-methoxy-2-naphthaleneaceyl chloride by HPLC. This method gives the high-purity L-carnitine in which the content of L-isomer may be more than 97% and that of R-isomer less than 2%.
