CN102875410B - 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

Info

Publication number
CN102875410B
CN102875410B CN201210341915.XA CN201210341915A CN102875410B CN 102875410 B CN102875410 B CN 102875410B CN 201210341915 A CN201210341915 A CN 201210341915A CN 102875410 B CN102875410 B CN 102875410B
Authority
CN
China
Prior art keywords
dimethyl
propylene diamine
group
sugared
propyl group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CN201210341915.XA
Other languages
Chinese (zh)
Other versions
CN102875410A (en
Inventor
智丽飞
李秋小
李运玲
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
China Daily Chemical Industry Research Institute
Original Assignee
China Daily Chemical Industry Research Institute
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by China Daily Chemical Industry Research Institute filed Critical China Daily Chemical Industry Research Institute
Priority to CN201210341915.XA priority Critical patent/CN102875410B/en
Publication of CN102875410A publication Critical patent/CN102875410A/en
Application granted granted Critical
Publication of CN102875410B publication Critical patent/CN102875410B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Abstract

A kind of general structure of N, N- dimethyl-N [3- (sugared amide groups)] propyl-N- alkyl bromination ammonium is as follows: Wherein: R is the long chain hydrocarbon groups of C8-C14, and glycosyl is monosaccharide groups or diglycosyl. The present invention has synthesis technology simple, and equipment requirement is low, is suitble to industrialization, and reaction temperature is low, is not necessarily to pressure and catalyst, and the response location on glycosyl determines that it is not in polysubstituted product, the high advantage of yield that reaction is balanced.

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, prepare environmentally-friendly surfactant and also more and more cause that people pay close attention to.Not only cost of material is cheap, aboundresources to produce tensio-active agent with carbohydrate, and products obtained therefrom gentleness, nontoxic, excellent property, environment compatibility are good, is one of focus of paying close attention to of 21 century people.Gluconolactone and lactobionic acid are prepared by renewable resources starch; there is low price, environmental protection, be easy to carry out the advantages such as amine ester reacts with alkylamine; and this reaction is carried out loaded down with trivial details, expensive protection without the hydroxyl on sugar; it is low that reaction has temperature; reaction conversion ratio is high; without advantages such as side reaction generations, meet very much the feature of atom economic reaction.Thereby, taking Gluconolactone and lactobionic acid as the glycosyl amide type tensio-active agent of raw material production, there is 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 it have mildness, hypotoxicity, the low irritant of nonionogenic tenside, 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 current synthetic method of Sugar-based Quaternary Ammonium Salt Surfactants be mainly with glucose or alkyl glycoside be raw material, first quaternized glucosides again or first glucosidesization more quaternised method synthesize.The people such as Kenneth B. Moser generate cationic reagent with low-grade tertiary amine (Trimethylamine 99, triethylamine, tripropyl amine) and epichlorohydrin reaction, and then react generation glycosyl quaternary ammonium salt with alkyl glycoside.The people such as Manfred Weuthen develop first alkyl glycoside and epichlorohydrin reaction, generate chloro glucosides intermediate, and then generate glycosyl quaternary ammonium salt with reactive tertiary amine.The main deficiency of these two kinds of methods is that in alkyl glycoside, the active difference of each hydroxyl is little, reacts uncertain where, reacts unbalanced, often occurs polysubstituted; The people such as John J. Tsai first react with chloro-hydrin(e) with glucose, obtain chloro glucosides, then carry out quaterisation with senior tertiary amine, obtain target product.This reaction in not only need catalyzer, and in quaterisation process because the intermiscibility of chloro glucosides and senior tertiary amine is bad, the steric hindrance of glucose is very large in addition, speed of reaction is very slow.And in the Sugar-based Quaternary Ammonium Salt Surfactants of reporting at present, be all the product combining with ehter bond mostly, the Sugar-based Quaternary Ammonium Salt Surfactants combining with amido linkage has no report.Amido linkage is similar to the peptide bond in 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, the reaction of 3-propylene diamine, generating N, N-dimethyl-N[3-(sugared amide group) with bromoalkane generation quaterisation again] synthetic method and the product structure of this class novel surfactant of propyl group-N-alkyl brometo de amonio there is not yet report.
Summary of the invention
The object of this invention is to provide one and utilize Gluconolactone or lactobionic acid elder generation and N; N-dimethyl-1; the reaction of 3-propylene diamine generates N; N-dimethyl-N '-sugared acyl group-1; 3-propylene diamine intermediate; the N preparing with bromoalkane generation quaterisation again, 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 (taking Gluconolactone as example):
Synthetic method of the present invention:
(1) press sugar and N, N-dimethyl-1, mole proportioning of 3-propylene diamine is 1.0:1.0-1.2, preferably 1:1,, make solvent with methyl alcohol, by sugar and N, N-dimethyl-1,3-propylene diamine mixes, preferably in the situation of methanol eddy, reacts, and be 45-65 DEG C in temperature of reaction, the reaction times is 6-10 h; After having reacted, evaporate solvent, with ether washing, obtain N, N-dimethyl-N '-sugared acyl group-1,3-propylene diamine intermediate;
(2) by N, N-dimethyl-N '-sugared acyl group-1,3-propylene diamine intermediate and bromoalkane; make solvent by low-carbon alcohol, temperature of reaction is 60-80 DEG C, and the reaction times is 15-20 h; wherein N, N-dimethyl-N '-sugared acyl group-1, mole proportioning of 3-propylene diamine intermediate and bromoalkane is 1.0:1.0-1.3; be preferably 1.0:1.1; after having reacted, evaporate solvent, wash with ether; obtain N, N-dimethyl-N[3-(sugared amide group)] propyl group-N-alkyl brometo de amonio.
Sugar as above is Gluconolactone and lactobionic acid.
Bromoalkane as above is long-chain C 8-C 14straight chained alkyl bromoalkane.
Low-carbon alcohol solvent as above is methyl alcohol, dehydrated alcohol or 95% ethanol.
N as above, 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 the N that structural characterization confirmation is analyzed, 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 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 have better consistency with skin, 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.
Compared with the technology of the present invention and existing sugar-based quaternary ammonium salt, tool has the following advantages:
1. synthesis technique of the present invention is simple, and equipment requirements is low, is applicable to industrialization.
Temperature of reaction low, without pressure and catalyzer.
3. the response location on glycosyl is determined, reaction is balanced, there will not be polysubstituted product, and productive rate is high.
Brief description of the 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-1,3-propylene diamine 1hNMR spectrogram;
Fig. 3 N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-octyl brometo de amonio 1hNMR spectrogram;
Fig. 4 N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-decyl brometo de amonio 1hNMR spectrogram;
Fig. 5 N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-dodecyl bromination ammonium 1hNMR spectrogram;
Fig. 6 N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-Tetradecylammonium bromide 1hNMR spectrogram;
Fig. 7 N, N-dimethyl-N '-lactose acyl group-1,3-propylene diamine 1hNMR spectrogram;
Fig. 8 N, N-dimethyl-N[3-(lactose amide base)] propyl group-N-dodecyl bromination ammonium 1hNMR spectrogram;
Fig. 9 N, N-dimethyl-N[3-(lactose amide base)] propyl group-N-Tetradecylammonium bromide 1hNMR spectrogram.
Embodiment
Embodiment 1
1, N, N-dimethyl-N '-glucose acyl group-1,3-propylene diamine synthetic
In the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep 55 DEG C of temperature, reaction 8 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, to ether washing for products obtained therefrom 2 times, remove remaining N, N-dimethyl-1,3-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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep temperature 60 C, reaction 20 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, ether washing 3 times for product, obtains brown syrup (N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-octyl brometo de amonio).Finally recording quaternary ammonium salt active matter content in product is 98.3%.
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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep 60 DEG C of temperature, reaction 7 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, to ether washing for products obtained therefrom 2 times, remove remaining N, N-dimethyl-1,3-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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep 80 DEG C of temperature, reaction 18 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, ether washing 3 times for product, obtains white powder solid (N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-decyl brometo de amonio).Finally recording quaternary ammonium salt active matter content in product is 99%.
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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep 65 DEG C of temperature, reaction 6 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, to ether washing for products obtained therefrom 2 times, remove remaining N, N-dimethyl-1,3-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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep temperature 70 C, reaction 17 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, ether washing 3 times for product, obtains white powder solid (N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-dodecyl bromination ammonium).Finally recording quaternary ammonium salt active matter content in product is 98.8%.
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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep 45 DEG C of temperature, reaction 10 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, to ether washing for products obtained therefrom 2 times, remove remaining N, N-dimethyl-1,3-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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep 77 DEG C of temperature, reaction 15 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, ether washing 3 times for product, obtains white powder solid (N, N-dimethyl-N[3-(glucose amide base)] propyl group-N-Tetradecylammonium bromide).Finally recording quaternary ammonium salt active matter content in product is 98.6%.
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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep 65 DEG C of temperature, reaction 8 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, to ether washing for products obtained therefrom 2 times, remove remaining N, N-dimethyl-1,3-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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep 65 DEG C of temperature, reaction 20 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, ether washing 3 times for product, obtains brown color solid (N, N-dimethyl-N[3-(lactose amide base)] propyl group-N-dodecyl bromination ammonium).Finally recording quaternary ammonium salt active matter content in product is 98.3%.
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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep 60 DEG C of temperature, reaction 8 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, to ether washing for products obtained therefrom 2 times, remove remaining N, N-dimethyl-1,3-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 the 250 mL tri-neck round-bottomed flasks that 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 stirring, keep temperature 60 C, reaction 20 h.Stop heating, leave standstill cooling.Evaporate solvent with Rotary Evaporators, ether washing 3 times for product, obtains brown color solid (N, N-dimethyl-N[3-(lactose amide base)] propyl group-N-Tetradecylammonium bromide).Finally recording quaternary ammonium salt active matter content in product is 98.4%.
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 (6)

1. a N, 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, mole proportioning of 3-propylene diamine is 1.0:1.0-1.2, makees solvent with methyl alcohol, by sugar and N, N-dimethyl-1,3-propylene diamine mixes, and is 45-65 DEG C in temperature of reaction, and the reaction times is 6-10h; After having reacted, evaporate solvent, with ether washing, obtain N, N-dimethyl-N '-sugared acyl group-1,3-propylene diamine intermediate;
(2) by N, N-dimethyl-N '-sugared acyl group-1,3-propylene diamine intermediate and bromoalkane, make solvent by low-carbon alcohol, temperature of reaction is 60-80 DEG C, and the reaction times is 15-20h, wherein N, N-dimethyl-N '-sugared acyl group-1, mole proportioning of 3-propylene diamine intermediate and bromoalkane is 1.0:1.0-1.3, after having reacted, evaporate solvent, with ether washing, obtain N, N-dimethyl-N[3-(sugared amide group)] propyl group-N-alkyl brometo de amonio;
Described sugar is Gluconolactone and lactobionic acid;
Described N, 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.
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 described bromoalkane is long-chain C 8-C 14straight chained alkyl bromoalkane.
3. 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 described low-carbon alcohol solvent is methyl alcohol, dehydrated alcohol or 95% ethanol.
4. 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 sugar and N, N-dimethyl-1, mole proportioning of 3-propylene diamine is 1:1.
5. 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 N, N-dimethyl-N '-sugared acyl group-1, mole proportioning of 3-propylene diamine intermediate and bromoalkane is 1.0:1.1.
6. 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 by sugar and N, N-dimethyl-1, mole proportioning of 3-propylene diamine is 1.0:1.0-1.2, makees solvent with methyl alcohol, by sugar and N, N-dimethyl-1,3-propylene diamine mixes, and is to react the in the situation that of methanol eddy.
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)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201210341915.XA CN102875410B (en) 2012-09-17 2012-09-17 N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201210341915.XA CN102875410B (en) 2012-09-17 2012-09-17 N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof

Publications (2)

Publication Number Publication Date
CN102875410A CN102875410A (en) 2013-01-16
CN102875410B true CN102875410B (en) 2014-11-26

Family

ID=47476969

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201210341915.XA Expired - Fee Related CN102875410B (en) 2012-09-17 2012-09-17 N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof

Country Status (1)

Country Link
CN (1) CN102875410B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2903978A1 (en) * 2013-03-14 2014-09-18 Akzo Nobel Chemicals International B.V. Nitrogen containing surfactants with alkoxylation on the hydroxyl group of fatty chains
CN104084085A (en) * 2014-07-15 2014-10-08 北京工商大学 Ethyoxyl modified alkyl glucosamide surfactant and preparation method thereof
CN104069773A (en) * 2014-07-15 2014-10-01 北京工商大学 Alkyl sugar amide dimeric surfactant and preparation method
CN104084084A (en) * 2014-07-15 2014-10-08 北京工商大学 Surfactant containing alkyl glucosamide and preparation method of surfactant
CN104610092B (en) * 2015-02-10 2016-08-17 齐齐哈尔大学 A kind of quaternary cationics and preparation method thereof
CN108246042B (en) * 2018-02-07 2020-05-15 太原科技大学 Chemical agglomeration agent for reducing superfine particulate matters of fire coal and preparation method
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
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

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0559748B1 (en) * 1990-11-30 1994-07-27 Richardson-Vicks, Inc. Gel type compositions having improved oil control
US5753245A (en) * 1994-08-26 1998-05-19 The Procter & Gamble Company Personal cleansing compositions
CN1562960A (en) * 2004-03-29 2005-01-12 中国日用化学工业研究院 Quaternary ammonium salt in ester-amines and synthetic method
CN1951908A (en) * 2006-11-10 2007-04-25 中国日用化学工业研究院 Preparation process for synthesizing AGA using loop reactor
CN101972612A (en) * 2010-11-10 2011-02-16 郑州轻工业学院 Sugar-based quaternary ammonium salt gemini surfactant and synthesis method thereof
CN102492146A (en) * 2011-12-07 2012-06-13 北京工商大学 Method for preparing polysiloxane containing alkyl and glucosamide
CN102503841A (en) * 2011-10-08 2012-06-20 中国日用化学工业研究院 Ethoxylate ester quaternary ammonium salt and its preparation method

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0559748B1 (en) * 1990-11-30 1994-07-27 Richardson-Vicks, Inc. Gel type compositions having improved oil control
US5753245A (en) * 1994-08-26 1998-05-19 The Procter & Gamble Company Personal cleansing compositions
CN1562960A (en) * 2004-03-29 2005-01-12 中国日用化学工业研究院 Quaternary ammonium salt in ester-amines and synthetic method
CN1951908A (en) * 2006-11-10 2007-04-25 中国日用化学工业研究院 Preparation process for synthesizing AGA using loop reactor
CN101972612A (en) * 2010-11-10 2011-02-16 郑州轻工业学院 Sugar-based quaternary ammonium salt gemini surfactant and synthesis method thereof
CN102503841A (en) * 2011-10-08 2012-06-20 中国日用化学工业研究院 Ethoxylate ester quaternary ammonium salt and its preparation method
CN102492146A (en) * 2011-12-07 2012-06-13 北京工商大学 Method for preparing polysiloxane containing alkyl and glucosamide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
一种非对称双尾阳离子表面活性剂的合成及表面活性;姜小明等;《精细化工》;20111231;第28卷(第12期);第1159-1163页 *
姜小明等.一种非对称双尾阳离子表面活性剂的合成及表面活性.《精细化工》.2011,第28卷(第12期), *

Also Published As

Publication number Publication date
CN102875410A (en) 2013-01-16

Similar Documents

Publication Publication Date Title
CN102875410B (en) N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof
CN101972612B (en) Sugar-based quaternary ammonium salt gemini surfactant and synthesis method thereof
CN102764609B (en) Glucose ester group quaternary ammonium salt cationic surfactant and synthesizing method thereof
CN106563385B (en) A kind of preparation method and application of alkyl glucoside quaternary ammonium surfactant
CN107670583B (en) A kind of glucosyl group Shuangzi nonionic surfactant, amphoteric surfactant and its synthetic method
CN107652203B (en) Glucose amide type gemini cationic surfactant and synthesis method thereof
CN107673987B (en) Glucosyl group Shuangzi nonionic surfactant and its synthetic method
CN103436570A (en) Preparation method for octenyl succinic starch ester
CN108409811A (en) The cis- polyglucoside surfactants of 1,2- and preparation method
CN101475498B (en) Preparation method of 3-dehydroabietylamine-2-hydroxypropyl trimethyl ammonium chloride
CN101928306A (en) Preparation method of glucoside cationic surfactant
CN102895913A (en) Cation type dimeric surfactant containing polyoxyethylene ether and synthetizing method of cation type dimeric surfactant
CN102179201A (en) Method for preparing cationic alkyl polyglycoside surfactant
CN102513023B (en) Trimeric surfactant and synthetic method thereof
CN103553889B (en) A kind of synthetic method of paradol
CN108892740A (en) A kind of synthetic method of 3,6 branching glucohexaoses
CN106518935B (en) A kind of synthetic method of bis- deoxidation -3- amino-L- idose of 3,6- and its derivative
CN104387426A (en) Method for regioselective synthesis of 6-O-acryloylsaccharide derivatives
CN108276461A (en) A kind of cheap synthetic method of Ethyl vanillin-β-D- glucopyranosides
CN101863777B (en) Preparation method for solvent-free 2, 4-dimethylaniline and 2, 6-dimethylaniline
CN104326949B (en) A kind of alternative functionalized ion liquid of amino acid separation, preparation method and application thereof
CN104725437A (en) Method for preparation of laminaribiose and rebaudiodside B by basic hydrolysis of rebaudiodside I
CN105214557A (en) A kind of N-alkyl aminopropionic acid type Gemini surface active agent and method for making
CN104001449B (en) Quaternary Ammonium Gemini Surfactants containing biphenyl group and preparation method thereof
CN106008617A (en) Tn antigen and synthesis process thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20141126

Termination date: 20190917

CF01 Termination of patent right due to non-payment of annual fee