[go: up one dir, main page]

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

Info

Publication number
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
Authority
CN
China
Prior art keywords
dimethyl
propyl
propanediamine
sugar
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.)
Granted
Application number
CN201210341915XA
Other languages
Chinese (zh)
Other versions
CN102875410B (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

Images

Landscapes

  • Saccharide Compounds (AREA)

Abstract

一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的结构通式如下:

Figure 201210341915X100004DEST_PATH_IMAGE002
其中:R为C8-C14的长链烃基,糖基为单糖基或二糖基。本发明具有合成工艺简单,设备要求低,适合工业化,反应温度低、无需压力和催化剂,糖基上的反应位置确定,反应均衡,不会出现多取代产物,产率高的优点。

Figure 201210341915

A kind of N,N-dimethyl-N [3-(sugar amido)] propyl-N-alkylammonium bromide has a general structural formula as follows:

Figure 201210341915X100004DEST_PATH_IMAGE002
Wherein: R is a C 8 -C 14 long-chain hydrocarbon group, and the sugar group is a monosaccharide group or a disaccharide group. The invention has the advantages of simple synthesis process, low equipment requirements, suitability for industrialization, low reaction temperature, no need for pressure and catalyst, definite reaction position on sugar groups, balanced reaction, no multi-substituted products and high yield.

Figure 201210341915

Description

N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵及其合成方法N,N-dimethyl-N[3-(sugaramido)]propyl-N-alkyl ammonium bromide and its synthesis method

技术领域 technical field

本发明涉及一种糖基酰胺季铵盐表面活性剂及其合成方法,具体地说涉及一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵及其合成方法。 The invention relates to a sugar-based amide quaternary ammonium salt surfactant and a synthesis method thereof, in particular to a N,N-dimethyl-N[3-(sugar amido)]propyl-N-alkyl Ammonium bromide and its synthesis method.

背景技术 Background technique

近年来,随着人们对环境问题的日益重视,制备环境友好型表面活性剂也越来越引起人们关注。用碳水化合物生产表面活性剂不仅原料价格低廉、资源丰富,而且所得产品温和、无毒、性能优良、环境兼容性好,是21世纪人们关注的热点之一。葡萄糖酸内酯和乳糖酸是由可再生资源淀粉制备而来的,具有价格便宜、绿色环保、易于与烷基胺进行胺酯反应等优点,且该反应无需对糖上的羟基进行繁琐、昂贵的保护,反应具有温度低,反应转化率高,无副反应发生等优点,很符合原子经济性反应的特点。因而,以葡萄糖酸内酯和乳糖酸为原料生产的糖基酰胺型表面活性剂,具有良好的发展空间。 In recent years, with people's increasing attention to environmental issues, the preparation of environmentally friendly surfactants has attracted more and more attention. The production of surfactants from carbohydrates is not only cheap in raw materials and rich in resources, but also mild, non-toxic, excellent in performance and good in environmental compatibility. It is one of the hot spots that people pay attention to in the 21st century. Gluconolactone and lactobionic acid are prepared from renewable resource starch, which have the advantages of low price, environmental protection, and easy amine ester reaction with alkylamines, and the reaction does not require cumbersome and expensive reactions on the hydroxyl groups on sugars. The protection of the reaction has the advantages of low temperature, high reaction conversion rate, no side reaction, etc., which is in line with the characteristics of atom-economical reaction. Therefore, the glycosylamide type surfactant produced from gluconolactone and lactobionic acid has a good development space.

糖基季铵盐表面活性剂结合了糖基表面活性剂的温和性与季铵盐型表面活性剂的高效性,使其具有非离子表面活性剂的温和性、低毒性、低刺激性,兼有阳离子表面活性剂的杀菌性、抗静电性和抗硬水性,还有一般阳离子表面活性剂所不具备的能和阴离子表面活性剂良好的配伍性能,是一种多功能型表面活性剂。 The sugar-based quaternary ammonium salt surfactant combines the mildness of the sugar-based surfactant and the high efficiency of the quaternary ammonium salt surfactant, making it have the mildness, low toxicity, and low irritation of the non-ionic surfactant, and also It has the bactericidal, antistatic and anti-hard water properties of cationic surfactants, as well as good compatibility with anionic surfactants that general cationic surfactants do not have. It is a multifunctional surfactant.

糖基季铵盐表面活性剂目前的合成方法主要是用葡萄糖或烷基糖苷为原料,先季铵化再糖苷化或先糖苷化再季铵化的方法来合成。Kenneth B. Moser等人用低级叔胺(三甲胺、三乙胺、三丙胺)与环氧氯丙烷反应生成阳离子化试剂,然后再与烷基糖苷反应生成糖苷基季铵盐。Manfred Weuthen等人开发出先将烷基糖苷与环氧氯丙烷反应,生成氯代糖苷中间体,然后再与叔胺反应生成糖苷基季铵盐。这两种方法的主要不足在于烷基糖苷中各羟基的活性差别不大,反应在什么位置不确定,反应不均衡,常出现多取代;John J. Tsai等人用葡萄糖先与氯代醇反应,得到氯代糖苷,再与高级叔胺进行季铵化反应,得到目标产物。此反应中不仅需要催化剂,而且季铵化反应过程中由于氯代糖苷和高级叔胺的相溶性不好,加之葡萄糖的位阻很大,反应速率很慢。且在目前报道的糖基季铵盐表面活性剂中大多都是以醚键相结合的产物,以酰胺键相结合的糖基季铵盐表面活性剂未见报道。酰胺键类似于蛋白质中的肽键,可以与皮肤具有更好的相容性,可赋予毛、皮肤自然光泽,并使之柔润。 The current synthesis method of sugar-based quaternary ammonium salt surfactant is mainly to use glucose or alkyl glycoside as raw material, first quaternized and then glycosidized or first glycosidized and then quaternized to synthesize. Kenneth B. Moser et al. used lower tertiary amines (trimethylamine, triethylamine, tripropylamine) to react with epichlorohydrin to generate cationization reagents, and then reacted with alkyl glycosides to generate glycoside-based quaternary ammonium salts. Manfred Weuthen and others developed the reaction of alkyl glycosides with epichlorohydrin to generate chloroglycoside intermediates, and then reacted with tertiary amines to generate glycoside-based quaternary ammonium salts. The main disadvantage of these two methods is that the activity of each hydroxyl group in the alkyl glycoside is not very different, the position of the reaction is uncertain, the reaction is unbalanced, and multiple substitutions often occur; John J. Tsai and others use glucose to react with chlorohydrins first. , to obtain chloroglucoside, and then carry out quaternization reaction with higher tertiary amine to obtain the target product. Not only need catalyzer in this reaction, and because the intermiscibility of chloroglucoside and advanced tertiary amine is bad in the quaternization reaction process, the steric hindrance of glucose is very big in addition, and reaction rate is very slow. And most of the sugar-based quaternary ammonium salt surfactants reported at present are products combined with ether bonds, and the sugar-based quaternary ammonium salt surfactants combined with amide bonds have not been reported. The amide bond is similar to the peptide bond in the protein, which can have better compatibility with the skin, and can give the hair and skin a natural luster and make it soft and moist.

用葡萄糖酸内酯或乳糖酸与N,N-二甲基-1,3-丙二胺反应,再与溴代烷发生季铵化反应生成N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵这类新型表面活性剂的合成方法和产物结构尚未见报道。 Use gluconolactone or lactobionic acid to react with N,N-dimethyl-1,3-propanediamine, and then react with brominated alkyl to generate N,N-dimethyl-N[3-( Sugar amido)] propyl-N-alkylammonium bromide synthesis method and product structure of this new class of surfactants have not been reported yet.

发明内容 Contents of the invention

本发明的目的是提供一种利用葡萄糖酸内酯或乳糖酸先与N,N-二甲基-1,3-丙二胺反应生成N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体,再与溴代烷发生季铵化反应制备的N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵及其合成方法。 The object of the present invention is to provide a method of utilizing gluconolactone or lactobionic acid to react with N,N-dimethyl-1,3-propanediamine to generate N,N-dimethyl-N'-sugar acyl-1 , 3-propanediamine intermediate, and N,N-dimethyl-N[3-(sugaramido)]propyl-N-alkyl ammonium bromide prepared by quaternization reaction with alkyl bromide and its synthesis method.

本发明提供的N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的结构通式如下: The general structural formula of N,N-dimethyl-N [3-(sugar amido)] propyl-N-alkylammonium bromide provided by the invention is as follows:

其中:R为C8-C14的长链烃基,糖基为单糖基或二糖基。 Wherein: R is a C 8 -C 14 long-chain hydrocarbon group, and the sugar group is a monosaccharide group or a disaccharide group.

反应路线如下(以葡萄糖酸内酯为例): The reaction scheme is as follows (taking gluconolactone as an example):

Figure 121975DEST_PATH_IMAGE002
Figure 121975DEST_PATH_IMAGE002

本发明的合成方法: Synthetic method of the present invention:

(1) 按糖和N,N-二甲基-1,3-丙二胺的摩尔配比为1.0:1.0-1.2,最好是1:1,,用甲醇做溶剂,将糖和N,N-二甲基-1,3-丙二胺混合,最好是甲醇回流的情况下反应,于反应温度为45-65 ℃,反应时间为6-10 h;反应完成后,蒸掉溶剂,用乙醚洗涤,得到N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体; (1) According to the molar ratio of sugar and N,N-dimethyl-1,3-propanediamine is 1.0:1.0-1.2, preferably 1:1, using methanol as solvent, sugar and N, N-dimethyl-1,3-propanediamine is mixed, preferably under the condition of methanol reflux, the reaction temperature is 45-65 ℃, and the reaction time is 6-10 h; after the reaction is completed, evaporate the solvent, Wash with ether to obtain N,N-dimethyl-N'-sugaryl-1,3-propanediamine intermediate;

(2)将N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体和溴代烷,用低碳醇作溶剂,反应温度为60-80 ℃,反应时间为15-20 h,其中N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体和溴代烷的摩尔配比为1.0:1.0-1.3,最好为1.0: 1.1,反应完成后,蒸掉溶剂,用乙醚洗涤,得到N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵。 (2) Mix N,N-dimethyl-N′-sugaryl-1,3-propanediamine intermediate and bromoalkane with lower alcohol as solvent, the reaction temperature is 60-80 ℃, and the reaction time is 15-20 h, wherein the molar ratio of N,N-dimethyl-N′-sugaryl-1,3-propanediamine intermediate and bromoalkane is 1.0:1.0-1.3, preferably 1.0:1.1 , After the reaction was completed, the solvent was distilled off and washed with ether to obtain N,N-dimethyl-N[3-(sugaramido)]propyl-N-alkylammonium bromide.

如上所述的糖为葡萄糖酸内酯和乳糖酸。 Sugars mentioned above are gluconolactone and lactobionic acid.

如上所述的溴代烷为长链C8-C14直链烷基溴代烷。 The brominated alkanes mentioned above are long chain C 8 -C 14 linear alkyl brominated alkanes.

如上所述的低碳醇溶剂为甲醇、无水乙醇或95%乙醇。 The above-mentioned low-carbon alcohol solvent is methanol, absolute ethanol or 95% ethanol.

如上所述的N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵经改良的佛尔哈特法方法测定,纯度大于98%。用IR和1H NMR进行结构表征确认所分析的N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵是目标产物。 The N,N-dimethyl-N[3-(sugaramido)]propyl-N-alkylammonium bromide as mentioned above was determined by the improved Volhart method, and the purity was greater than 98%. Structural characterization by IR and 1 H NMR confirmed that the analyzed N,N-dimethyl-N[3-(sugaramido)]propyl-N-alkylammonium bromide was the target product.

本发明所制备的产品为糖基酰胺季铵盐表面活性剂,在结构上不仅具有非离子型的糖基亲水基,而且具有阳离子型季铵盐的特性,还有酰胺键的特性。因此此产品性能温和、低毒、低刺激,兼有阳离子表面活性剂的杀菌性、抗静电性和抗硬水性,还和皮肤有更好的相容性,及其与阴离子表面活性剂的良好配伍性能,是一种多功能型表面活性剂。可广泛应用于纺织、造纸、化妆品、洗涤用品、采矿业和钻井液等行业,具有良好的应用前景。 The product prepared by the present invention is a sugar-based amide quaternary ammonium salt surfactant, which not only has a non-ionic sugar-based hydrophilic group, but also has the characteristics of a cationic quaternary ammonium salt and an amide bond. Therefore, this product has mild performance, low toxicity, and low irritation. It has both the bactericidal, antistatic and hard water resistance of cationic surfactants, and has better compatibility with skin and good compatibility with anionic surfactants. Compatibility, is a multifunctional surfactant. It can be widely used in industries such as textiles, papermaking, cosmetics, washing supplies, mining and drilling fluid, and has a good application prospect.

本发明与现有的糖基季铵盐的技术相比具有如下优点: Compared with the technology of existing glycosyl quaternary ammonium salt, the present invention has the following advantages:

1.本发明合成工艺简单,设备要求低,适合工业化。 1. The synthesis process of the present invention is simple, requires low equipment, and is suitable for industrialization.

2.反应温度低、无需压力和催化剂。 2. Low reaction temperature, no need for pressure and catalyst.

3.糖基上的反应位置确定,反应均衡,不会出现多取代产物,产率高。 3. The reaction position on the sugar group is determined, the reaction is balanced, there will be no multiple substitution products, and the yield is high.

附图说明 Description of drawings

图 1 N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的红外谱图; Figure 1 The infrared spectrum of N,N-dimethyl-N′-glucosyl-1,3-propanediamine;

图 2 N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的1HNMR谱图; Figure 2 1 H NMR spectrum of N,N-dimethyl-N′-glucosyl-1,3-propanediamine;

图 3 N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-辛烷基溴化铵的1HNMR谱图; Figure 3 1 HNMR spectrum of N,N-dimethyl-N[3-(glucosamido)]propyl-N-octyl ammonium bromide;

图 4 N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-癸烷基溴化铵的1HNMR谱图; Figure 4 1 HNMR spectrum of N,N-dimethyl-N[3-(glucosamido)]propyl-N-decyl ammonium bromide;

图 5 N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十二烷基溴化铵的1HNMR谱图; Figure 5 1 HNMR spectrum of N,N-dimethyl-N[3-(glucosamido)]propyl-N-dodecylammonium bromide;

图 6 N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十四烷基溴化铵的1HNMR谱图; Figure 6 1 HNMR spectrum of N,N-dimethyl-N[3-(glucosamido)]propyl-N-tetradecylammonium bromide;

图 7 N,N-二甲基-N′-乳糖酰基-1,3-丙二胺的1HNMR谱图; Figure 7 1 HNMR spectrum of N,N-dimethyl-N′-lactoyl-1,3-propanediamine;

图 8 N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十二烷基溴化铵的1HNMR谱图; Figure 8 1 HNMR spectrum of N,N-dimethyl-N[3-(lactosamido)]propyl-N-dodecylammonium bromide;

图 9 N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十四烷基溴化铵的1HNMR谱图。 Figure 9 1 H NMR spectrum of N,N-dimethyl-N[3-(lactosamido)]propyl-N-tetradecylammonium bromide.

具体实施方式 Detailed ways

实施例 1 Example 1

1、N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的合成 1. Synthesis of N,N-dimethyl-N'-glucosyl-1,3-propanediamine

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入12.2 g (120 mmol) N,N-二甲基-1,3-丙二胺,葡萄糖酸内酯21.4 g (120 mmol),甲醇80 mL。在搅拌的条件下,保持温度55 ℃,反应8 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到白色粉末固体(N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺)32.2 g,产率95.8 %。 In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 21.4 g (120 mmol) gluconolactone ), methanol 80 mL. Under the condition of stirring, keep the temperature at 55 ℃, and react for 8 h. Remove from heat and let cool. The solvent was distilled off with a rotary evaporator, and the resulting product was washed twice with ether to remove residual N,N-dimethyl-1,3-propanediamine to obtain a white powder solid (N,N-dimethyl-N '-glucosyl-1,3-propanediamine) 32.2 g, yield 95.8%.

IR(KBr): 3368 cm-1 (ν(O–H)), 2941-2819 cm-1 (ν(C–H) in –CH2– or -CH3 ), ( 1651 cm-1 (ν(C=O) in amide), 1542 cm-1 (δ(N–H) in amide), 1461 cm-1(ν(C–H) in –CH2– ), 1091-1036 cm-1(ν(O–H)), 718 cm-1(δ(C-C) in >4CH2). 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(CC) in >4CH 2 ).

1H-NMR (CDCl3, ppm) δ: 1.618 (m, 2H, CH2 CH 2 CH2), 2.223 (s, 6H, N(CH 3 )2), 2.298 (t, 2H, NHCH2CH2 CH 2 ), 2.765 (t, 2H, NHCH 2 CH2CH2), 3.307-4.274 (6H, protons of sugar ), 7.794 (s, 1H, CONH).  1 H-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 2 CH 2 CH 2 ), 2.765 (t, 2H, NH CH 2 CH 2 CH 2 ), 3.307-4.274 (6H, protons of sugar ), 7.794 (s, 1H, CO NH ).

2、N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-辛烷基溴化铵的合成 2. Synthesis of N,N-dimethyl-N[3-(glucosamido)]propyl-N-octyl ammonium bromide

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺15 g (53.6 mmol),溴代辛烷10.3 g (53.6 mmol), 无水乙醇80 mL。在搅拌的条件下,保持温度60℃,反应20 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到棕色糖浆(N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-辛烷基溴化铵)。最后测得产品中季铵盐活性物含量为98.3%。 In a 250 mL three-necked round-bottomed flask equipped with a thermometer and a spherical condenser, add 15 g (53.6 mmol) of N,N-dimethyl-N′-glucosyl-1,3-propanediamine, octyl bromide Alkanes 10.3 g (53.6 mmol), absolute ethanol 80 mL. Under the condition of stirring, keep the temperature at 60°C and react for 20 h. Remove from heat and let cool. The solvent was evaporated with a rotary evaporator, and the product was washed three times with ether to obtain a brown syrup (N,N-dimethyl-N[3-(glucosamido)]propyl-N-octylammonium bromide). It is 98.3% to measure the quaternary ammonium salt active substance content in the product at last.

1H-NMR (CDCl3, ppm) δ: 0.890 (t, 3H, (CH2)5 CH 3 ), 1.268 (m, 10H, (CH 2 ) 5 CH3), 1.729 (m, 2H, CH 2 (CH2)5CH3), 2.108 (m, 2H, NHCH2 CH 2 CH2), 3.230 (s, 6H, N(CH 3 )2), 3.394 (t, 2H, NCH 2 CH2), 3.570 (t, 2H, NHCH2CH2 CH 2 ), 3.781 (t, 2H, NHCH 2 CH2CH2), 4.137-5.516 (6H, protons of sugar ), 8.089 (s, 1H, CONH). 1 H-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 ) 5 CH 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 2 CH 2 CH 2 ), 3.781 (t, 2H, NH CH 2 CH 2 CH 2 ), 4.137-5.516 (6H, protons of sugar ), 8.089 (s, 1H, CO NH ).

实施例 2 Example 2

N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的合成 Synthesis of N,N-Dimethyl-N'-glucosyl-1,3-propanediamine

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入12.2 g (120 mmol) N,N-二甲基-1,3-丙二胺,葡萄糖酸内酯20.5 g (115 mmol),甲醇80 mL。在搅拌的条件下,保持温度60 ℃,反应7 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到白色粉末固体(N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺)30.2g,产率92.4 %。 In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 20.5 g (115 mmol) gluconolactone ), methanol 80 mL. Under the condition of stirring, keep the temperature at 60 ℃, and react for 7 h. Remove from heat and let cool. Evaporate the solvent with a rotary evaporator, wash the resulting product twice with ether to remove residual N,N-dimethyl-1,3-propanediamine, and obtain a white powder solid (N,N-dimethyl-N '-glucosyl-1,3-propanediamine) 30.2g, yield 92.4%.

N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-癸烷基溴化铵的合成 Synthesis of N,N-Dimethyl-N[3-(glucosamido)]propyl-N-decylammonium bromide

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺15 g (53.6 mmol),溴代癸烷13 g (59 mmol), 无水乙醇80 mL。在搅拌的条件下,保持温度80℃,反应18 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到白色粉末固体(N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-癸烷基溴化铵)。最后测得产品中季铵盐活性物含量为99%。 In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 15 g (53.6 mmol) of N,N-dimethyl-N′-glucosyl-1,3-propanediamine, bromodecyl Alkanes 13 g (59 mmol), absolute ethanol 80 mL. Under the condition of stirring, keep the temperature at 80°C, and react for 18 h. Remove from heat and let cool. Evaporate the solvent with a rotary evaporator, and wash the product with ether three times to obtain a white powder solid (N,N-dimethyl-N[3-(glucosamido)]propyl-N-decyl ammonium bromide) . It is 99% to measure the quaternary ammonium salt active substance content in the product at last.

1H-NMR (CDCl3, ppm) δ: 0.890 (t, 3H, (CH2)7 CH 3 ), 1.267 (m, 14H, (CH 2 ) 7 CH3), 1.731 (m, 2H, CH 2 (CH2)7CH3), 2.112 (m, 2H, NHCH2 CH 2 CH2), 3.234 (s, 6H, N(CH 3 )2), 3.395 (t, 2H, NCH 2 CH2), 3.591 (t, 2H, NHCH2CH2 CH 2 ), 3.782 (t, 2H, NHCH 2 CH2CH2), 4.146-5.518 (6H, protons of sugar ), 8.091 (s, 1H, CONH). 1 H-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 ) 7 CH 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 2 CH 2 CH 2 ), 3.782 (t, 2H, NH CH 2 CH 2 CH 2 ), 4.146-5.518 (6H, protons of sugar ), 8.091 (s, 1H, CO NH ).

实施例 3 Example 3

N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的合成 Synthesis of N,N-Dimethyl-N'-glucosyl-1,3-propanediamine

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入12.2 g (120 mmol) N,N-二甲基-1,3-丙二胺,葡萄糖酸内酯19.6 g (110 mmol),甲醇80 mL。在搅拌的条件下,保持温度65 ℃,反应6 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到白色粉末固体(N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺)30 g,产率94.3 %。 In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 19.6 g (110 mmol) gluconolactone ), methanol 80 mL. Under the condition of stirring, keep the temperature at 65 ℃, and react for 6 h. Remove from heat and let cool. Evaporate the solvent with a rotary evaporator, wash the resulting product twice with ether to remove residual N,N-dimethyl-1,3-propanediamine, and obtain a white powder solid (N,N-dimethyl-N '-glucosyl-1,3-propanediamine) 30 g, yield 94.3%.

N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十二烷基溴化铵的合成 Synthesis of N,N-Dimethyl-N[3-(glucosamido)]propyl-N-dodecylammonium bromide

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺15 g (53.6 mmol),溴代十二烷15.9 g (64 mmol), 95%乙醇80 mL。在搅拌的条件下,保持温度70℃,反应17 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到白色粉末固体(N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十二烷基溴化铵)。最后测得产品中季铵盐活性物含量为98.8%。 In a 250 mL three-necked round-bottomed flask equipped with a thermometer and a spherical condenser, add 15 g (53.6 mmol) of N,N-dimethyl-N′-glucosyl-1,3-propanediamine, decabromide Dioxane 15.9 g (64 mmol), 95% ethanol 80 mL. Under the condition of stirring, the temperature was kept at 70°C, and the reaction was carried out for 17 h. Remove from heat and let cool. The solvent was distilled off with a rotary evaporator, and the product was washed 3 times with ether to obtain a white powder solid (N,N-dimethyl-N[3-(glucosamido)]propyl-N-dodecylammonium bromide ). Finally, the content of quaternary ammonium salt active matter in the product is 98.8%.

1H-NMR(CDCl3, ppm) δ: 0.893(t, 3H, (CH2)9 CH 3 ), 1.268 (m, 18H, (CH 2 ) 9 CH3), 1.733 (m, 2H, CH 2 (CH2)9CH3), 2.088 (m, 2H, NHCH2 CH 2 CH2), 3.237 (s, 6H, N(CH 3 )2), 3.420 (t, 2H, NCH 2 CH2), 3.605 (t, 2H, NHCH2CH2 CH 2 ), 3.787 (t, 2H, NHCH 2 CH2CH2), 4.154-5.598 (6H, protons of sugar ), 8.093 (s, 1H, CONH) 1 H-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 ) 9 CH 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 2 CH 2 CH 2 ), 3.787 (t, 2H, NH CH 2 CH 2 CH 2 ), 4.154-5.598 (6H, protons of sugar ), 8.093 (s, 1H, CO NH )

实施例 4 Example 4

N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的合成 Synthesis of N,N-Dimethyl-N'-glucosyl-1,3-propanediamine

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入12.2 g (120 mmol) N,N-二甲基-1,3-丙二胺,葡萄糖酸内酯17.8 g (100 mmol),甲醇80 mL。在搅拌的条件下,保持温度45 ℃,反应10 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到白色粉末固体(N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺)27.5 g,产率91.7 %。 In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 17.8 g (100 mmol) gluconolactone ), methanol 80 mL. Under the condition of stirring, keep the temperature at 45 ℃, and react for 10 h. Remove from heat and let cool. Evaporate the solvent with a rotary evaporator, wash the resulting product twice with ether to remove residual N,N-dimethyl-1,3-propanediamine, and obtain a white powder solid (N,N-dimethyl-N '-glucosyl-1,3-propanediamine) 27.5 g, yield 91.7%.

N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十四烷基溴化铵的合成 Synthesis of N,N-Dimethyl-N[3-(glucosamido)]propyl-N-tetradecylammonium bromide

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺15 g (53.6 mmol),溴代十四烷19.3 g (69.7 mmol), 95%乙醇80 mL。在搅拌的条件下,保持温度77℃,反应15 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到白色粉末固体(N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十四烷基溴化铵)。最后测得产品中季铵盐活性物含量为98.6%。 In a 250 mL three-necked round-bottomed flask equipped with a thermometer and a spherical condenser, add 15 g (53.6 mmol) of N,N-dimethyl-N′-glucosyl-1,3-propanediamine, decabromide Tetraxane 19.3 g (69.7 mmol), 95% ethanol 80 mL. Under the condition of stirring, keep the temperature at 77°C and react for 15 h. Remove from heat and let cool. The solvent was distilled off with a rotary evaporator, and the product was washed 3 times with ether to obtain a white powder solid (N,N-dimethyl-N[3-(glucosamidyl)]propyl-N-tetradecylammonium bromide ). It is 98.6% to measure the quaternary ammonium salt active substance content in the product at last.

1H-NMR(CDCl3, ppm) δ: 0.883(t, 3H, (CH2)11 CH 3 ), 1.268 (m, 22H, (CH 2 ) 11 CH3), 1.726 (m, 2H, CH 2 (CH2)11CH3), 2.088 (m, 2H, NHCH2 CH 2 CH2), 3.235 (s, 6H, N(CH 3 )2), 3.393 (t, 2H, NCH 2 CH2), 3.583 (t, 2H, NHCH2CH2 CH 2 ), 3.786 (t, 2H, NHCH 2 CH2CH2), 4.154-5.537 (6H, protons of sugar ), 8.065 (s, 1H, CONH) 1 H-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 ) 11 CH 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 2 CH 2 CH 2 ), 3.786 (t, 2H, NH CH 2 CH 2 CH 2 ), 4.154-5.537 (6H, protons of sugar ), 8.065 (s, 1H, CO NH )

实施例 5 Example 5

N,N-二甲基-N′-乳糖酰基-1,3-丙二胺的合成 Synthesis of N,N-Dimethyl-N'-lactoyl-1,3-propanediamine

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入6.1 g (60 mmol) N,N-二甲基-1,3-丙二胺,乳糖酸21.5 g (60 mmol),甲醇80 mL。在搅拌的条件下,保持温度65 ℃,反应8 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到浅棕色粉末固体(N,N-二甲基-N′-乳糖酰基-1,3-丙二胺)26 g,产率94.2 %。 In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 6.1 g (60 mmol) of N,N-dimethyl-1,3-propanediamine, 21.5 g (60 mmol) of lactobionic acid, Methanol 80 mL. Under the condition of stirring, keep the temperature at 65 ℃, and react for 8 h. Remove from heat and let cool. Evaporate the solvent with a rotary evaporator, wash the resulting product twice with ether to remove residual N,N-dimethyl-1,3-propanediamine, and obtain a light brown powder solid (N,N-dimethyl-1,3- N′-lactoyl-1,3-propanediamine) 26 g, yield 94.2%.

IR(KBr): 3384 cm-1 (ν(O–H)), 2938-2828 cm-1 (ν(C–H) in –CH2– or -CH3 ), ( 1653 cm-1 (ν(C=O) in amide), 1541 cm-1 (δ(N–H) in amide), 1457 cm-1(ν(C–H) in –CH2– ), 1078-1048 cm-1(ν(O–H)), 705 cm-1(δ(C-C) in >4CH2) 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(CC) in >4CH 2 )

1H-NMR (D2O, ppm) δ: 1.17 (m, 2H, CH2 CH 2 CH2), 1.73 (t, 2H, NHCH2CH2 CH 2 ), 2.27 (s, 6H, N(CH 3 )2), 2.43 (t, 2H, NHCH 2 CH2CH2), 3.27-4.57 (13H, protons of sugar ) 1 H-NMR (D 2 O, ppm) δ: 1.17 (m, 2H, CH 2 CH 2 CH 2 ), 1.73 (t, 2H, NHCH 2 CH 2 CH 2 ), 2.27 (s, 6H, N( CH 3 ) 2 ), 2.43 (t, 2H, NH CH 2 CH 2 CH 2 ), 3.27-4.57 (13H, protons of sugar )

N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十二烷基溴化铵的合成 Synthesis of N,N-Dimethyl-N[3-(lactosamido)]propyl-N-dodecylammonium bromide

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-乳糖酰基-1,3-丙二胺6.9 g (15 mmol),溴代十二烷4 g (16 mmol), 甲醇80 mL。在搅拌的条件下,保持温度65℃,反应20 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到棕黄色固体(N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十二烷基溴化铵)。最后测得产品中季铵盐活性物含量为98.3%。 In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 6.9 g (15 mmol) of N,N-dimethyl-N′-lactoyl-1,3-propanediamine, decabromide Dioxane 4 g (16 mmol), methanol 80 mL. Under the condition of stirring, keep the temperature at 65°C, and react for 20 h. Remove from heat and let cool. The solvent was distilled off with a rotary evaporator, and the product was washed 3 times with ether to obtain a brownish-yellow solid (N,N-dimethyl-N[3-(lactosamido)]propyl-N-dodecylammonium bromide ). It is 98.3% to measure the quaternary ammonium salt active substance content in the product at last.

1H-NMR(D2O, ppm) δ: 0.82(t, 3H, (CH2)9 CH 3 ), 1.23 (m, 18H, (CH 2 ) 9 CH3), 1.69 (m, 2H, CH 2 (CH2)9CH3), 1.98 (m, 2H, NHCH2 CH 2 CH2), 2.78 (t, 2H, NCH 2 CH2), 3.01 (s, 6H, N(CH 3 )2), 3.27 (m, 4H, NHCH 2 CH2 CH 2 ), 3.53-4.52 (13H, protons of sugar ) 1 H-NMR(D 2 O, 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 ) 9 CH 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 )

实施例 6 Example 6

N,N-二甲基-N′-乳糖酰基-1,3-丙二胺的合成 Synthesis of N,N-Dimethyl-N'-lactoyl-1,3-propanediamine

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入6.1 g (60 mmol) N,N-二甲基-1,3-丙二胺,乳糖酸21.5 g (60 mmol),甲醇80 mL。在搅拌的条件下,保持温度60 ℃,反应8 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到浅棕色粉末固体(N,N-二甲基-N′-乳糖酰基-1,3-丙二胺)26 g,产率93.2 %。 In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 6.1 g (60 mmol) of N,N-dimethyl-1,3-propanediamine, 21.5 g (60 mmol) of lactobionic acid, Methanol 80 mL. Under the condition of stirring, keep the temperature at 60 ℃, and react for 8 h. Remove from heat and let cool. Evaporate the solvent with a rotary evaporator, wash the resulting product twice with ether to remove residual N,N-dimethyl-1,3-propanediamine, and obtain a light brown powder solid (N,N-dimethyl-1,3- N′-lactoyl-1,3-propanediamine) 26 g, yield 93.2%.

N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十四烷基溴化铵的合成 Synthesis of N,N-Dimethyl-N[3-(lactosamido)]propyl-N-tetradecylammonium bromide

在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-乳糖酰基-1,3-丙二胺6.9 g (15 mmol),溴代十四烷4 g (17 mmol), 甲醇80 mL。在搅拌的条件下,保持温度60℃,反应20 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到棕黄色固体(N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十四烷基溴化铵)。最后测得产品中季铵盐活性物含量为98.4%。 In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 6.9 g (15 mmol) of N,N-dimethyl-N′-lactoyl-1,3-propanediamine, decabromide Tetraxane 4 g (17 mmol), methanol 80 mL. Under the condition of stirring, keep the temperature at 60°C and react for 20 h. Remove from heat and let cool. The solvent was distilled off with a rotary evaporator, and the product was washed 3 times with ether to obtain a brownish yellow solid (N,N-dimethyl-N[3-(lactosamido)]propyl-N-tetradecyl ammonium bromide ). It is 98.4% to measure the quaternary ammonium salt active matter content in the product at last.

1H-NMR(D2O, ppm) δ: 0.81(t, 3H, (CH2)11 CH 3 ), 1.24 (m, 22H, (CH 2 ) 11 CH3), 1.70 (m, 2H, CH 2 (CH2)11CH3), 1.98 (m, 2H, NHCH2 CH 2 CH2), 2.81 (t, 2H, NCH 2 CH2), 3.04 (s, 6H, N(CH 3 )2), 3.30 (m, 4H, NHCH 2 CH 2 CH 2 ), 3.48-4.50 (13H, protons of sugar)。 1 H-NMR(D 2 O, 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 ) 11 CH 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)

1.一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵,,其特征在于N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的结构通式如下: 1. A N,N-dimethyl-N[3-(sugar amido)]propyl-N-alkyl ammonium bromide, characterized in that N,N-dimethyl-N[3-( Sugar amido)] propyl group-N-alkyl ammonium bromide structural general formula is as follows:
Figure 201210341915X100001DEST_PATH_IMAGE002
Figure 201210341915X100001DEST_PATH_IMAGE002
其中:R为C8-C14的长链烃基,糖基为单糖基或二糖基。 Wherein: R is a C 8 -C 14 long-chain hydrocarbon group, and the sugar group is a monosaccharide group or a disaccharide group.
2.如权利要求1所述的一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的合成方法,,其特征在于包括如下步骤: 2. a kind of N as claimed in claim 1, the synthetic method of N-dimethyl-N [3-(sugar amido)] propyl group-N-alkyl ammonium bromide, is characterized in that comprising the following steps : (1) 按糖和N,N-二甲基-1,3-丙二胺的摩尔配比为1.0:1.0-1.2,用甲醇做溶剂,将糖和N,N-二甲基-1,3-丙二胺混合,最好是甲醇回流的情况下反应,于反应温度为45-65 ℃,反应时间为6-10 h;反应完成后,蒸掉溶剂,用乙醚洗涤,得到N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体; (1) According to the molar ratio of sugar and N,N-dimethyl-1,3-propanediamine as 1.0:1.0-1.2, using methanol as solvent, sugar and N,N-dimethyl-1, Mix 3-propanediamine, it is best to react under the condition of methanol reflux, the reaction temperature is 45-65 ℃, and the reaction time is 6-10 h; after the reaction is completed, evaporate the solvent and wash with ether to obtain N,N -Dimethyl-N'-sugaryl-1,3-propanediamine intermediate; (2)将N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体和溴代烷,用低碳醇作溶剂,反应温度为60-80 ℃,反应时间为15-20 h,其中N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体和溴代烷的摩尔配比为1.0:1.0-1.3,反应完成后,蒸掉溶剂,用乙醚洗涤,得到N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵。 (2) Mix N,N-dimethyl-N′-sugaryl-1,3-propanediamine intermediate and bromoalkane with lower alcohol as solvent, the reaction temperature is 60-80 ℃, and the reaction time is 15-20 h, wherein the molar ratio of N,N-dimethyl-N′-sugaryl-1,3-propanediamine intermediate and bromoalkane is 1.0:1.0-1.3, after the reaction is completed, evaporate The solvent was washed with ether to obtain N,N-dimethyl-N[3-(sugaramido)]propyl-N-alkylammonium bromide. 3.如权利要求2所述的一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的合成方法,,其特征在于所述的糖为葡萄糖酸内酯和乳糖酸。 3. a kind of N as claimed in claim 2, the synthetic method of N-dimethyl-N [3-(sugaramido)] propyl-N-alkyl ammonium bromide, is characterized in that described The sugars are gluconolactone and lactobionic acid. 4.如权利要求2所述的一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的合成方法,,其特征在于所述的溴代烷为长链C8-C14直链烷基溴代烷。 4. a kind of N as claimed in claim 2, the synthetic method of N-dimethyl-N [3-(sugaramido)] propyl-N-alkyl ammonium bromide, is characterized in that described Brominated alkanes are long chain C 8 -C 14 linear alkyl brominated alkanes. 5.如权利要求2所述的一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的合成方法,,其特征在于所述的低碳醇溶剂为甲醇、无水乙醇或95%乙醇。 5. a kind of N as claimed in claim 2, the synthetic method of N-dimethyl-N [3-(sugaramido)] propyl-N-alkylammonium bromide, is characterized in that described The low-carbon alcohol solvent is methanol, absolute ethanol or 95% ethanol. 6.如权利要求2所述的一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的合成方法,,其特征在于糖和N,N-二甲基-1,3-丙二胺的摩尔配比为1:1。 6. a kind of N as claimed in claim 2, the synthetic method of N-dimethyl-N [3-(sugar amido)] propyl-N-alkyl ammonium bromide, it is characterized in that sugar and N , The molar ratio of N-dimethyl-1,3-propanediamine is 1:1. 7.如权利要求2所述的一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的合成方法,,其特征在于,N-二甲基-N′-糖酰基-1,3-丙二胺中间体和溴代烷的摩尔配比为1.0: 1.1。 7. A kind of N, N-dimethyl-N [3-(sugar amido)] propyl-N-alkyl ammonium bromide synthetic method as claimed in claim 2, it is characterized in that, N- The molar ratio of dimethyl-N'-sugaryl-1,3-propanediamine intermediate and brominated alkyl 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)

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 true CN102875410A (en) 2013-01-16
CN102875410B 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)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104069773A (en) * 2014-07-15 2014-10-01 北京工商大学 Alkyl sugar amide dimeric surfactant and preparation method
CN104084085A (en) * 2014-07-15 2014-10-08 北京工商大学 Ethyoxyl modified alkyl glucosamide surfactant and preparation method thereof
CN104084084A (en) * 2014-07-15 2014-10-08 北京工商大学 Surfactant containing alkyl glucosamide and preparation method of surfactant
CN104610092A (en) * 2015-02-10 2015-05-13 齐齐哈尔大学 Quaternary ammonium salt cationic surfactant and preparation method thereof
JP2016516021A (en) * 2013-03-14 2016-06-02 アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップAkzo Nobel Chemicals International B.V. Nitrogen-containing surfactants having alkoxylation on the hydroxyl group of the fatty chain
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
CN114230481A (en) * 2021-12-29 2022-03-25 太原科技大学 A kind of low toxicity bactericidal glycosyl amide ionic liquid and its preparation method and application

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 (1)

* Cited by examiner, † Cited by third party
Title
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》 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016516021A (en) * 2013-03-14 2016-06-02 アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップAkzo Nobel Chemicals International B.V. Nitrogen-containing surfactants having alkoxylation on the hydroxyl group of the fatty chain
CN104069773A (en) * 2014-07-15 2014-10-01 北京工商大学 Alkyl sugar amide dimeric surfactant and preparation method
CN104084085A (en) * 2014-07-15 2014-10-08 北京工商大学 Ethyoxyl modified alkyl glucosamide surfactant and preparation method thereof
CN104084084A (en) * 2014-07-15 2014-10-08 北京工商大学 Surfactant containing alkyl glucosamide and preparation method of surfactant
CN104610092A (en) * 2015-02-10 2015-05-13 齐齐哈尔大学 Quaternary ammonium salt cationic surfactant and preparation method thereof
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 A kind of low toxicity bactericidal glycosyl amide ionic liquid and its preparation method and application
CN114230481B (en) * 2021-12-29 2023-09-22 太原科技大学 A low-toxicity bactericidal glycosyl amide ionic liquid and its preparation method and application

Also Published As

Publication number Publication date
CN102875410B (en) 2014-11-26

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
CN101972612A (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
CN101703905B (en) A kind of double quaternary ammonium salt disulfonate surfactant and its synthetic method
CN107673987A (en) Glucosyl group Shuangzi nonionic surfactant and its synthetic method
CN107670583A (en) A kind of glucosyl group Shuangzi nonionic surfactant, amphoteric surfactant and its synthetic method
CN105964185B (en) A kind of asymmetric Cationic Gemini Surfactant of coupling link hydroxyl group
CN107652203A (en) A kind of glucose amide type gemini cationic surfactant and its synthetic method
Kumar et al. d-Glucose derived novel gemini surfactants: synthesis and study of their surface properties, interaction with DNA, and cytotoxicity
CN101475498A (en) Preparation method of 3-dehydroabietylamine-2-hydroxypropyl trimethyl ammonium chloride
CN105126905B (en) A kind of ionic liquid and preparation method and application of synthesizing long-chain alkyl glucosides
CN108409811A (en) The cis- polyglucoside surfactants of 1,2- and preparation method
Ibatullin et al. Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors
CN101792427A (en) Method for combining polysubstituted furan
Nowicki et al. Synthesis and surface active properties of novel carbohydrate-based cationic surfactants
CN103539827B (en) The method of a kind of synthesis to methoxyl group triphenyl α-S-(1 → 6)-D-glucobiose
CN108276461B (en) A kind of cheap synthetic method of ethyl vanillin-β-D-glucopyranoside
CN103553889B (en) A kind of synthetic method of paradol
CN102030803B (en) A kind of tea saponin derivative and its preparation method and application
CN104086608A (en) High-efficiency synthesis method of natural product glucan pentasaccharide
CN109894050A (en) A kind of aryl ether sulfobetaine surfactant and preparation method thereof
CN102513023B (en) Trimeric surfactant and synthetic method thereof
CN104387426A (en) Method for regioselective synthesis of 6-O-acryloylsaccharide derivatives
Karuna et al. Synthesis of sulfated sodium salts of 1‐alkylamino‐3‐alkyloxy‐2‐propanols and N, N‐di‐(2‐hydroxy‐3‐alkyloxy propyl) alkylamines as potential surfactants
CN106518935B (en) A kind of synthetic method of bis- deoxidation -3- amino-L- idose of 3,6- and its derivative

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