CN102875410A - N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof - Google Patents

N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof Download PDF

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CN102875410A
CN102875410A CN201210341915XA CN201210341915A CN102875410A CN 102875410 A CN102875410 A CN 102875410A CN 201210341915X A CN201210341915X A CN 201210341915XA CN 201210341915 A CN201210341915 A CN 201210341915A CN 102875410 A CN102875410 A CN 102875410A
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propyl group
propylene diamine
sugared
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CN102875410B (en
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智丽飞
李秋小
李运玲
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China Daily Chemical Industry Research Institute
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China Daily Chemical Industry Research Institute
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Abstract

The invention relates to N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide of which the general formula of structure is as follows: wherein the R is a long chain alkyl of the C8-C14; and the glycosyl is a single-glycosyl or a dual-glycosyl. The synthetic method provided by the invention has the advantages that the synthetic process is simple, the requirement to equipment is low, the method is suitable for industrialization, the required reaction temperature is low, pressure and catalyst are not required, the reaction positions on the glycosyl are certain, the reaction is balanced, the amount of generated substitution products is not large, and the productivity is high.

Description

N, N-dimethyl-N[3-(sugared amide group)] propyl group-N-alkyl brometo de amonio and synthetic method thereof
Technical field
The present invention relates to a kind of glycosyl amide quaternary surfactant and synthetic method thereof, relate in particular to a kind of N, N-dimethyl-N[3-(sugared amide group)] propyl group-N-alkyl brometo de amonio and synthetic method thereof.
Background technology
In recent years, along with the pay attention to day by day of people to environmental problem, the preparation environmentally-friendly surfactant causes more and more that also people pay close attention to.Not only cost of material is cheap, aboundresources to produce tensio-active agent with carbohydrate, and products obtained therefrom is gentle, nontoxic, excellent property, environment compatibility are good, is one of focus of 21 century people concern.Gluconolactone and lactobionic acid are prepared by renewable resources starch; have low price, environmental protection, be easy to carry out with alkylamine the advantages such as amine ester reaction; and this reaction need not the hydroxyl on the sugar is carried out loaded down with trivial details, expensive protection; it is low that reaction has temperature; reaction conversion ratio is high; without advantages such as side reaction generations, meet very much the characteristics of atom economic reaction.Thereby, take Gluconolactone and lactobionic acid as the glycosyl amide type tensio-active agent of raw material production, have good development space.
Sugar-based Quaternary Ammonium Salt Surfactants combines the high efficiency of mildness and the quaternary ammonium salt cationic surfactant of glycosyl surfactant active, make its mildness with nonionogenic tenside, hypotoxicity, low irritant, have bactericidal properties, static resistance and the anti-hard water of cats product concurrently, also having the not available energy of general cats product and the good compatibility of anion surfactant, is a kind of multifunctional type tensio-active agent.
The present synthetic method of Sugar-based Quaternary Ammonium Salt Surfactants mainly is to be raw material with glucose or alkyl glycoside, first quaternized again glucosides or first glucosidesization more quaternised method synthesize.The human low-grade tertiary amines (Trimethylamine 99, triethylamine, tripropyl amine) such as Kenneth B. Moser generate cationic reagent with epichlorohydrin reaction, and then generate the glycosyl quaternary ammonium salt with the alkyl glycoside reaction.The people such as Manfred Weuthen develop first alkyl glycoside and epichlorohydrin reaction, generate chloro glucosides intermediate, and then generate the glycosyl quaternary ammonium salt with reactive tertiary amine.The main deficiency of these two kinds of methods is that the active difference of each hydroxyl is little in the alkyl glycoside, reacts uncertain where, reacts unbalanced, often occurs polysubstituted; The human glucose such as John J. Tsai react with chloro-hydrin(e) first, obtain the chloro glucosides, carry out quaterisation with senior tertiary amine again, obtain target product.Not only need catalyzer in this reaction, and in the quaterisation process because the intermiscibility of chloro glucosides and senior tertiary amine is bad, and the steric hindrance of glucose is very large in addition, speed of reaction is very slow.And all be the product that combines with ehter bond mostly in the Sugar-based Quaternary Ammonium Salt Surfactants of reporting at present, the Sugar-based Quaternary Ammonium Salt Surfactants that combines with amido linkage has no report.Amido linkage is similar to the peptide bond in the protein, can have better consistency with skin, can give hair, skin natural gloss, and make it soft and moist.
With Gluconolactone or lactobionic acid and N, N-dimethyl-1,3-propylene diamine reaction generates N, N-dimethyl-N[3-(sugared amide group) with bromoalkane generation quaterisation again] synthetic method and the product structure of propyl group-this class novel surfactant of N-alkyl brometo de amonio there is not yet report.
Summary of the invention
The purpose of this invention is to provide a kind of Gluconolactone or lactobionic acid elder generation and N of utilizing; N-dimethyl-1; the reaction of 3-propylene diamine generates N; N-dimethyl-N '-sugared acyl group-1; 3-propylene diamine intermediate; again with the N of bromoalkane generation quaterisation preparation, N-dimethyl-N[3-(sugared amide group)] propyl group-N-alkyl brometo de amonio and synthetic method thereof.
N provided by the invention, N-dimethyl-N[3-(sugared amide group)] general structure of propyl group-N-alkyl brometo de amonio is as follows:
Wherein: R is C 8-C 14Long chain hydrocarbon groups, glycosyl is monosaccharide groups or diglycosyl.
Reaction scheme following (take Gluconolactone as example):
Figure 121975DEST_PATH_IMAGE002
Synthetic method of the present invention:
(1) press sugar and N, N-dimethyl-1, the mole proportioning of 3-propylene diamine is 1.0:1.0-1.2, preferably 1:1,, make solvent with methyl alcohol, with sugar and N, N-dimethyl-1, the 3-propylene diamine mixes, preferably reacts in the situation of methanol eddy, and be 45-65 ℃ in temperature of reaction, the reaction times is 6-10 h; After reaction is finished, evaporate solvent, with the ether washing, obtain N, N-dimethyl-N '-sugared acyl group-1,3-propylene diamine intermediate;
(2) with N, N-dimethyl-N '-sugared acyl group-1,3-propylene diamine intermediate and bromoalkane; make solvent with low-carbon alcohol, temperature of reaction is 60-80 ℃, and the reaction times is 15-20 h; N wherein, N-dimethyl-N '-sugared acyl group-1, the mole proportioning of 3-propylene diamine intermediate and bromoalkane is 1.0:1.0-1.3; be preferably 1.0:1.1; after reaction is finished, evaporate solvent, wash with ether; obtain N, N-dimethyl-N[3-(sugared amide group)] propyl group-N-alkyl brometo de amonio.
Aforesaid sugar is Gluconolactone and lactobionic acid.
Aforesaid bromoalkane is long-chain C 8-C 14The straight chained alkyl bromoalkane.
Aforesaid low-carbon alcohol solvent is methyl alcohol, dehydrated alcohol or 95% ethanol.
Aforesaid N, N-dimethyl-N[3-(sugared amide group)] the Fo Er Harter Act method mensuration of propyl group-N-alkyl brometo de amonio through improveing, purity is greater than 98%.With IR and 1H NMR carries out structural characterization and confirms the N analyze, N-dimethyl-N[3-(sugared amide group)] propyl group-N-alkyl brometo de amonio is target product.
The prepared product of the present invention is the glycosyl amide quaternary surfactant, structurally not only has the glycosyl hydrophilic group of non-ionic type, and has the characteristic of cationic quaternary ammonium salt, also has the characteristic of amido linkage.Therefore this product performance gentleness, low toxicity, low stimulation, have bactericidal properties, static resistance and the anti-hard water of cats product concurrently, also with skin better consistency is arranged, and with the good compatibility of anion surfactant, be a kind of multifunctional type tensio-active agent.Can be widely used in the industries such as weaving, papermaking, makeup, articles for washing, mining industry and drilling fluid, have a good application prospect.
The present invention compares with the technology of existing sugar-based quaternary ammonium salt has following advantage:
1. synthesis technique of the present invention is simple, and equipment requirements is low, is fit to industrialization.
Temperature of reaction low, need not pressure and catalyzer.
3. the response location on the glycosyl is determined, reaction is balanced, polysubstituted product can not occur, and productive rate is high.
Description of drawings
Fig. 1 N, N-dimethyl-N '-glucose acyl group-1, the infrared spectrum of 3-propylene diamine;
Fig. 2 N, N-dimethyl-N '-glucose acyl group-1, the 3-propylene diamine 1The HNMR spectrogram;
Fig. 3 N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-octyl brometo de amonio 1The HNMR spectrogram;
Fig. 4 N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-decyl brometo de amonio 1The HNMR spectrogram;
Fig. 5 N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-dodecyl bromination ammonium 1The HNMR spectrogram;
Fig. 6 N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-Tetradecylammonium bromide 1The HNMR spectrogram;
Fig. 7 N, N-dimethyl-N '-lactose acyl group-1, the 3-propylene diamine 1The HNMR spectrogram;
Fig. 8 N, N-dimethyl-N[3-(lactose amide base)] propyl group-N-dodecyl bromination ammonium 1The HNMR spectrogram;
Fig. 9 N, N-dimethyl-N[3-(lactose amide base)] propyl group-N-Tetradecylammonium bromide 1The HNMR spectrogram.
Embodiment
Embodiment 1
1, N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add 12.2 g (120 mmol) N, N-dimethyl-1,3-propylene diamine, Gluconolactone 21.4 g (120 mmol), methyl alcohol 80 mL.Under the condition that stirs, keep 55 ℃ of temperature, react 8 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, products obtained therefrom with ether washing 2 times, is removed remaining N, N-dimethyl-1, the 3-propylene diamine obtains white powder solid (N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine) 32.2 g, productive rate 95.8 %.
IR(KBr):?3368?cm -1?( ν(O–H)),?2941-2819?cm -1?( ν(C–H)?in?–CH 2–?or?-CH 3?),?(?1651?cm -1?( ν(C=O)?in?amide),?1542?cm -1?(δ(N–H)?in?amide),?1461?cm -1( ν(C–H)?in?–CH 2–?),?1091-1036?cm -1( ν(O–H)),?718?cm -1(δ(C-C)?in?>4CH 2).
1H-NMR?(CDCl 3,?ppm)?δ:?1.618?(m,?2H,?CH 2 CH 2 CH 2),?2.223?(s,?6H,?N( CH 3 ) 2),?2.298?(t,?2H,?NHCH 2CH 2 CH 2 ),?2.765?(t,?2H,?NH CH 2 CH 2CH 2),?3.307-4.274?(6H,?protons?of?sugar?),?7.794?(s,?1H,?CO NH).
2, N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-octyl brometo de amonio synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine 15 g (53.6 mmol), bromooctane 10.3 g (53.6 mmol), dehydrated alcohol 80 mL.Under the condition that stirs, keep temperature 60 C, react 20 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, product is with ether washing 3 times, obtains brown syrup (N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-octyl brometo de amonio).Record at last that the quaternary ammonium salt active matter content is 98.3% in the product.
1H-NMR?(CDCl 3,?ppm)?δ:?0.890?(t,?3H,?(CH 2) 5 CH 3 ),?1.268?(m,?10H, ?(CH 2 ) 5 CH 3),?1.729?(m,?2H,? CH 2 (CH 2) 5CH 3),?2.108?(m,?2H,?NHCH 2 CH 2 CH 2),?3.230?(s,?6H,?N( CH 3 ) 2),?3.394?(t,?2H,?N CH 2 CH 2),?3.570?(t,?2H,?NHCH 2CH 2 CH 2 ),?3.781?(t,?2H,?NH CH 2 CH 2CH 2),?4.137-5.516?(6H,?protons?of?sugar?),?8.089?(s,?1H,?CO NH).
Embodiment 2
N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add 12.2 g (120 mmol) N, N-dimethyl-1,3-propylene diamine, Gluconolactone 20.5 g (115 mmol), methyl alcohol 80 mL.Under the condition that stirs, keep 60 ℃ of temperature, react 7 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, products obtained therefrom with ether washing 2 times, is removed remaining N, N-dimethyl-1, the 3-propylene diamine obtains white powder solid (N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine) 30.2g, productive rate 92.4 %.
N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-decyl brometo de amonio synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine 15 g (53.6 mmol), bromodecane 13 g (59 mmol), dehydrated alcohol 80 mL.Under the condition that stirs, keep 80 ℃ of temperature, react 18 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, product is with ether washing 3 times, obtains white powder solid (N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-decyl brometo de amonio).Record at last that the quaternary ammonium salt active matter content is 99% in the product.
1H-NMR?(CDCl 3,?ppm)?δ:?0.890?(t,?3H,?(CH 2) 7 CH 3 ),?1.267?(m,?14H, ?(CH 2 ) 7 CH 3),?1.731?(m,?2H,? CH 2 (CH 2) 7CH 3),?2.112?(m,?2H,?NHCH 2 CH 2 CH 2),?3.234?(s,?6H,?N( CH 3 ) 2),?3.395?(t,?2H,?N CH 2 CH 2),?3.591?(t,?2H,?NHCH 2CH 2 CH 2 ),?3.782?(t,?2H,?NH CH 2 CH 2CH 2),?4.146-5.518?(6H,?protons?of?sugar?),?8.091?(s,?1H,?CO NH).
Embodiment 3
N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add 12.2 g (120 mmol) N, N-dimethyl-1,3-propylene diamine, Gluconolactone 19.6 g (110 mmol), methyl alcohol 80 mL.Under the condition that stirs, keep 65 ℃ of temperature, react 6 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, products obtained therefrom with ether washing 2 times, is removed remaining N, N-dimethyl-1, the 3-propylene diamine obtains white powder solid (N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine) 30 g, productive rate 94.3 %.
N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-dodecyl bromination ammonium synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine 15 g (53.6 mmol), bromododecane 15.9 g (64 mmol), 95% ethanol, 80 mL.Under the condition that stirs, keep temperature 70 C, react 17 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, product is with ether washing 3 times, obtains white powder solid (N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-dodecyl bromination ammonium).Record at last that the quaternary ammonium salt active matter content is 98.8% in the product.
1H-NMR(CDCl 3,?ppm)?δ:?0.893(t,?3H,?(CH 2) 9 CH 3 ),?1.268?(m,?18H, ?(CH 2 ) 9 CH 3),?1.733?(m,?2H,? CH 2 (CH 2) 9CH 3),?2.088?(m,?2H,?NHCH 2 CH 2 CH 2),?3.237?(s,?6H,?N( CH 3 ) 2),?3.420?(t,?2H,?N CH 2 CH 2),?3.605?(t,?2H,?NHCH 2CH 2 CH 2 ),?3.787?(t,?2H,?NH CH 2 CH 2CH 2),?4.154-5.598?(6H,?protons?of?sugar?),?8.093?(s,?1H,?CO NH)
Embodiment 4
N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add 12.2 g (120 mmol) N, N-dimethyl-1,3-propylene diamine, Gluconolactone 17.8 g (100 mmol), methyl alcohol 80 mL.Under the condition that stirs, keep 45 ℃ of temperature, react 10 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, products obtained therefrom with ether washing 2 times, is removed remaining N, N-dimethyl-1, the 3-propylene diamine obtains white powder solid (N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine) 27.5 g, productive rate 91.7 %.
N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-Tetradecylammonium bromide synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine 15 g (53.6 mmol), bromotetradecane 19.3 g (69.7 mmol), 95% ethanol, 80 mL.Under the condition that stirs, keep 77 ℃ of temperature, react 15 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, product is with ether washing 3 times, obtains white powder solid (N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-Tetradecylammonium bromide).Record at last that the quaternary ammonium salt active matter content is 98.6% in the product.
1H-NMR(CDCl 3,?ppm)?δ:?0.883(t,?3H,?(CH 2) 11 CH 3 ),?1.268?(m,?22H, ?(CH 2 ) 11 CH 3),?1.726?(m,?2H,? CH 2 (CH 2) 11CH 3),?2.088?(m,?2H,?NHCH 2 CH 2 CH 2),?3.235?(s,?6H,?N( CH 3 ) 2),?3.393?(t,?2H,?N CH 2 CH 2),?3.583?(t,?2H,?NHCH 2CH 2 CH 2 ),?3.786?(t,?2H,?NH CH 2 CH 2CH 2),?4.154-5.537?(6H,?protons?of?sugar?),?8.065?(s,?1H,?CO NH)
Embodiment 5
N, N-dimethyl-N '-lactose acyl group-1,3-propylene diamine synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add 6.1 g (60 mmol) N, N-dimethyl-1,3-propylene diamine, lactobionic acid 21.5 g (60 mmol), methyl alcohol 80 mL.Under the condition that stirs, keep 65 ℃ of temperature, react 8 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, products obtained therefrom with ether washing 2 times, is removed remaining N, N-dimethyl-1, the 3-propylene diamine obtains light brown powder solid (N, N-dimethyl-N '-lactose acyl group-1,3-propylene diamine) 26 g, productive rate 94.2 %.
IR(KBr):?3384?cm -1?( ν(O–H)),?2938-2828?cm -1?( ν(C–H)?in?–CH 2–?or?-CH 3?),?(?1653?cm -1?( ν(C=O)?in?amide),?1541?cm -1?(δ(N–H)?in?amide),?1457?cm -1( ν(C–H)?in?–CH 2–?),?1078-1048?cm -1( ν(O–H)),?705?cm -1(δ(C-C)?in?>4CH 2)
1H-NMR?(D 2O,?ppm)?δ:?1.17?(m,?2H,?CH 2 CH 2 CH 2),?1.73?(t,?2H,?NHCH 2CH 2 CH 2 ),?2.27?(s,?6H,?N( CH 3 ) 2),?2.43?(t,?2H,?NH CH 2 CH 2CH 2),?3.27-4.57?(13H,?protons?of?sugar?)
N, N-dimethyl-N[3-(lactose amide base)] propyl group-N-dodecyl bromination ammonium synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add N, N-dimethyl-N '-lactose acyl group-1,3-propylene diamine 6.9 g (15 mmol), bromododecane 4 g (16 mmol), methyl alcohol 80 mL.Under the condition that stirs, keep 65 ℃ of temperature, react 20 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, product is with ether washing 3 times, obtains brown color solid (N, N-dimethyl-N[3-(lactose amide base)] propyl group-N-dodecyl bromination ammonium).Record at last that the quaternary ammonium salt active matter content is 98.3% in the product.
1H-NMR(D 2O,?ppm)?δ:?0.82(t,?3H,?(CH 2) 9 CH 3 ),?1.23?(m,?18H, ?(CH 2 ) 9 CH 3),?1.69?(m,?2H,? CH 2 (CH 2) 9CH 3),?1.98?(m,?2H,?NHCH 2 CH 2 CH 2),?2.78?(t,?2H,?N CH 2 CH 2),?3.01?(s,?6H,?N( CH 3 ) 2),?3.27?(m,?4H,?NH CH 2 CH 2 CH 2 ),?3.53-4.52?(13H,?protons?of?sugar?)
Embodiment 6
N, N-dimethyl-N '-lactose acyl group-1,3-propylene diamine synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add 6.1 g (60 mmol) N, N-dimethyl-1,3-propylene diamine, lactobionic acid 21.5 g (60 mmol), methyl alcohol 80 mL.Under the condition that stirs, keep 60 ℃ of temperature, react 8 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, products obtained therefrom with ether washing 2 times, is removed remaining N, N-dimethyl-1, the 3-propylene diamine obtains light brown powder solid (N, N-dimethyl-N '-lactose acyl group-1,3-propylene diamine) 26 g, productive rate 93.2 %.
N, N-dimethyl-N[3-(lactose amide base)] propyl group-N-Tetradecylammonium bromide synthetic
In 250 mL, the three neck round-bottomed flasks of thermometer and spherical condensation tube are housed, add N, N-dimethyl-N '-lactose acyl group-1,3-propylene diamine 6.9 g (15 mmol), bromotetradecane 4 g (17 mmol), methyl alcohol 80 mL.Under the condition that stirs, keep temperature 60 C, react 20 h.Stopped heating leaves standstill cooling.Evaporate solvent with Rotary Evaporators, product is with ether washing 3 times, obtains brown color solid (N, N-dimethyl-N[3-(lactose amide base)] propyl group-N-Tetradecylammonium bromide).Record at last that the quaternary ammonium salt active matter content is 98.4% in the product.
1H-NMR(D 2O,?ppm)?δ:?0.81(t,?3H,?(CH 2) 11 CH 3 ),?1.24?(m,?22H, ?(CH 2 ) 11 CH 3),?1.70?(m,?2H,? CH 2 (CH 2) 11CH 3),?1.98?(m,?2H,?NHCH 2 CH 2 CH 2),?2.81?(t,?2H,?N CH 2 CH 2),?3.04?(s,?6H,?N( CH 3 ) 2),?3.30?(m,?4H,?NH CH 2 CH 2 CH 2 ),?3.48-4.50?(13H,?protons?of?sugar)。

Claims (7)

1. N, N-dimethyl-N[3-(sugared amide group)] propyl group-N-alkyl brometo de amonio,, it is characterized in that N, N-dimethyl-N[3-(sugared amide group)] and the general structure of propyl group-N-alkyl brometo de amonio is as follows:
Figure 201210341915X100001DEST_PATH_IMAGE002
Wherein: R is C 8-C 14Long chain hydrocarbon groups, glycosyl is monosaccharide groups or diglycosyl.
2. a kind of N as claimed in claim 1, N-dimethyl-N[3-(sugared amide group)] synthetic method of propyl group-N-alkyl brometo de amonio,, it is characterized in that comprising the steps:
(1) press sugar and N, N-dimethyl-1, the mole proportioning of 3-propylene diamine is 1.0:1.0-1.2, makees solvent with methyl alcohol, with sugar and N, N-dimethyl-1, the 3-propylene diamine mixes, preferably reacting in the situation of methanol eddy, is 45-65 ℃ in temperature of reaction, and the reaction times is 6-10 h; After reaction is finished, evaporate solvent, with the ether washing, obtain N, N-dimethyl-N '-sugared acyl group-1,3-propylene diamine intermediate;
(2) with N, N-dimethyl-N '-sugared acyl group-1,3-propylene diamine intermediate and bromoalkane; make solvent with low-carbon alcohol, temperature of reaction is 60-80 ℃, and the reaction times is 15-20 h; N wherein; N-dimethyl-N '-sugared acyl group-1, the mole proportioning of 3-propylene diamine intermediate and bromoalkane is 1.0:1.0-1.3, after reaction is finished; evaporate solvent; with the ether washing, obtain N, N-dimethyl-N[3-(sugared amide group)] propyl group-N-alkyl brometo de amonio.
3. a kind of N as claimed in claim 2, N-dimethyl-N[3-(sugared amide group)] synthetic method of propyl group-N-alkyl brometo de amonio,, it is characterized in that described sugar is Gluconolactone and lactobionic acid.
4. a kind of N as claimed in claim 2, N-dimethyl-N[3-(sugared amide group)] synthetic method of propyl group-N-alkyl brometo de amonio,, it is characterized in that described bromoalkane is long-chain C 8-C 14The straight chained alkyl bromoalkane.
5. a kind of N as claimed in claim 2, N-dimethyl-N[3-(sugared amide group)] synthetic method of propyl group-N-alkyl brometo de amonio,, it is characterized in that described low-carbon alcohol solvent is methyl alcohol, dehydrated alcohol or 95% ethanol.
6. a kind of N as claimed in claim 2, N-dimethyl-N[3-(sugared amide group)] synthetic method of propyl group-N-alkyl brometo de amonio,, it is characterized in that sugar and N, N-dimethyl-1, the mole proportioning of 3-propylene diamine is 1:1.
7. a kind of N as claimed in claim 2; N-dimethyl-N[3-(sugared amide group)] synthetic method of propyl group-N-alkyl brometo de amonio,, it is characterized in that; N-dimethyl-N '-sugared acyl group-1, the mole proportioning of 3-propylene diamine intermediate and bromoalkane is 1.0:1.1.
CN201210341915.XA 2012-09-17 2012-09-17 N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof Expired - Fee Related CN102875410B (en)

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CN108246042A (en) * 2018-02-07 2018-07-06 太原科技大学 A kind of chemical agglomeration agent for reducing coal-fired superfine particulate matters and preparation method
CN108452630A (en) * 2018-02-07 2018-08-28 太原科技大学 Reduce chemical agglomeration agent and the preparation method of waste incineration superfine particulate matter
CN108452630B (en) * 2018-02-07 2020-06-02 太原科技大学 Chemical aggregating agent for reducing waste incineration ultrafine particles and preparation method thereof
CN114230481A (en) * 2021-12-29 2022-03-25 太原科技大学 Low-toxicity bactericidal glycosyl amide ionic liquid and preparation method and application thereof
CN114230481B (en) * 2021-12-29 2023-09-22 太原科技大学 Low-toxicity sterilizing glycosylamide ionic liquid and preparation method and application thereof

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