CN101254436A - Octadecanamide surfactant and synthetic method - Google Patents
Octadecanamide surfactant and synthetic method Download PDFInfo
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- CN101254436A CN101254436A CNA2007101507511A CN200710150751A CN101254436A CN 101254436 A CN101254436 A CN 101254436A CN A2007101507511 A CNA2007101507511 A CN A2007101507511A CN 200710150751 A CN200710150751 A CN 200710150751A CN 101254436 A CN101254436 A CN 101254436A
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Abstract
An octadecanamide surfactant and a synthetic method are provided. The inventive octadecanamide surfactant has the structural formula mentioned as above. The synthetic method includes the following steps: synthesizing the octadecanamide surfactant intermediate by using stearic acid and hydroxyethylethylene diamine as raw materials, and then performing amphoteric reaction by 'chloroacetic acid process' to obtain the octadecanamide surfactant. Based on the prior art, the invention utilizes stearic acid, hydroxyethylethylene diamine and chloroacetic acid as raw materials, to directly synthesize amide surfactants by a novel vacuum-amphoteric method without ring closing reaction. The inventive octadecanamide surfactant has low foaming and wetting performance and is widely used as a monomer of a textile finish agent.
Description
[technical field]:
The invention belongs to surfactant and preparing technical field thereof.
[background technology]:
Octadecanamide surfactant involved in the present invention is a kind of novel surfactant, and its performance and carboxylic acid type imidazoline amophoteric surface active agent compare favourably.
The imidazoline type amphoteric surfactant of aliphatic group has performances such as excellent washing, wetting, foaming and dispersion
[1,2], excitant is very low
[3], low toxicity or nontoxic
[4], antistatic
[5], antibiotic
[6], environmentally friendly.
Amphoteric surfactant is pressed its textural classification: (1) imidazoline amophoteric surface active agent (2) beet alkali ampholytic surface active agent (3) amino acid surfactant (4) lecithin class surfactant.Wherein lecithin class surfactant is natural surfactant, and remaining is artificial synthetic
[7]
Amphoteric surfactant is the later class of exploitation in surfactant.Nineteen thirty-seven, United States Patent (USP) just had report.Du pont company had been developed this compounds in 1940, and reported first betaine be amphoteric surfactant.It is amphoteric surfactant that German AdolfSchmitz in 1948 has studied amino acid, and begins to use.The U.S. has just produced more than 20 kind of amphoteric surfactant commodity in the eighties in 20th century.Phase late 1980s, the amphoteric surfactant of the U.S. increases with the annual growth of 5%-6%, considerably beyond the annual average rate of increase of industrial surface activity agent 2% at that time.Entered since the nineties in 20th century, the amphoteric surfactant of developed country is still in steady development, and the output of the amphoteric surfactant of developed country accounts for the 2%-3% of surfactant total output, and the kind number of present Japanese amphoteric surfactant is about 200
[8]
Domesticly after the seventies in 20th century, begin amphoteric surfactant is conducted a research, have few products to throw people market at present, but kind and quantity are all few, so in amphoteric surface the live research and the application facet of agent, China still is in the starting stage.In China's amphoteric surfactant kind, the still non-betaine type of output maximum does not belong to, and what occupy next is amphoteric imidazoline.The ascendant trend of amido propyl betaine type is very fast in the betaine, and alkyl betaine is the atrophy gesture.Amphoteric imidazoline is not smooth in the development of China, by the leading position of the eighties in 20th century, drops to the subordinate status of the nineties in 20th century, and it is also descending to ratio of cation imidazoline, is to be lower than 50% weak tendency
[9]
[summary of the invention]:
The object of the invention provides a kind of acid amide type surfactant, particularly Octadecanamide surfactant and synthetic method thereof.
The present invention is on the basis of summing up former achievements, and with stearic acid, AEEA and monoxone are raw material, without the ring process that reaches a standard, adopt the vacuum-direct synthesizing amide type of amphoterisation method surfactant innovatively.
Octadecanamide surfactant of the present invention, its structural formula is:
The synthetic route of Octadecanamide surfactant of the present invention is:
Concrete synthetic method is as follows:
The first, the Octadecanamide surfactant intermediate is synthetic:
With stearic acid and AEEA is raw material, synthetic Octadecanamide surfactant intermediate, and concrete synthetic method is as follows:
Mechanical agitation is housed, temperature is taken into account in the four-hole bottle of vacuum distillation apparatus, add stearic acid and AEEA (mol ratio is 1: 1～1.5) and begin heating and stirring, slowly reaction temperature is risen to 100 ℃ ± 10 ℃, till when starting vavuum pump conditioned reaction system vacuum to water outlet, in 3-5 hour, make reaction temperature rise to 150 ℃ ± 10 ℃ gradually, complete to water outlet.Stop heating, cooling obtains the Octadecanamide surfactant intermediate, and structural formula is:
For the structure of Octadecanamide surfactant intermediate, utilize infrared tracking, can from infrared spectrum, observe, at 1640cm
-1And 1560cm
-1Near the very strong acid amides characteristic absorption peak of appearance is at 3300cm
-1About occur bimodal, at 3100cm
-1Occur unimodally, illustrate that intermediate is the mixture of secondary amide and teritary amide.Instrument: NICOLET-205 infrared spectrometer.
The second, adopt " chloroactic acid method " to carry out amphoterisation and obtain Octadecanamide surfactant
Concrete synthetic method is as follows:
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, add heating of Octadecanamide surfactant intermediate and stirring, between 50～90 ℃ of temperature, low temperature drips chloroacetic acid solution in 4 hours, heat up gradually then and drip NaOH solution, Octadecanamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 1～1.3: 2～2.6, and then reacts 1-2 hour, stop reaction, obtain yellow supernatant liquid and be Octadecanamide surfactant.
Advantage of the present invention and good effect:
The present invention is an acidamide surfactant, has low bubble property, low wetability.
Octadecanamide surfactant provided by the invention is widely used in the monomer of textile finish oil.
[specific embodiment]:
Embodiment 1:
Mechanical agitation is housed, temperature is taken into account in the four-hole bottle of vacuum distillation apparatus, add stearic acid 174.2g (0.6mol) and AEEA (mol ratio is 1: 1) and begin heating and stirring, slowly reaction temperature is risen to 100 ℃, till when starting vavuum pump conditioned reaction system vacuum to water outlet, in 3 hours, make reaction temperature rise to 150 ℃ gradually, complete to water outlet.Stop heating, cooling obtains the Octadecanamide surfactant intermediate.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, add Octadecanamide surfactant intermediate 22.3g (0.06mol) heating and stirring, between 50～90 ℃ of temperature, low temperature drips chloroacetic acid solution in 4 hours, heat up gradually then and drip NaOH solution, Octadecanamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 1: 2, and then reacts 1 hour, stop reaction, obtain yellow supernatant liquid and be Octadecanamide surfactant.Surface tension σ (20 ℃, 49.84mNm
-1) instrument: DP-AW type surface tension instrument.
Embodiment 2:
Mechanical agitation is housed, temperature is taken into account in the four-hole bottle of vacuum distillation apparatus, add stearic acid 174.2g (0.6mol) and AEEA (mol ratio is 1: 1.1) and begin heating and stirring, slowly reaction temperature is risen to 110 ℃, till when starting vavuum pump conditioned reaction system vacuum to water outlet, in 4 hours, make reaction temperature rise to 150 ℃ gradually, complete to water outlet.Stop heating, cooling obtains the Octadecanamide surfactant intermediate.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, add Octadecanamide surfactant intermediate 22.3g (0.06mol) heating and stirring, between 50～90 ℃ of temperature, low temperature drips chloroacetic acid solution in 4 hours, heat up gradually then and drip NaOH solution, Octadecanamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 1.3: 2.6, and then reacted 1.5 hours, stop reaction, obtain yellow supernatant liquid and be Octadecanamide surfactant.
Embodiment 3:
Mechanical agitation is housed, temperature is taken into account in the four-hole bottle of vacuum distillation apparatus, add stearic acid 174.2g (0.6mol) and AEEA (mol ratio is 1: 1.2) and begin heating and stirring, slowly reaction temperature is risen to 100 ℃, till when starting vavuum pump conditioned reaction system vacuum to water outlet, in 5 hours, make reaction temperature rise to 150 ℃ gradually, complete to water outlet.Stop heating, cooling obtains the Octadecanamide surfactant intermediate.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, add Octadecanamide surfactant intermediate 22.3g (0.06mol) heating and stirring, between 50～90 ℃ of temperature, low temperature drips chloroacetic acid solution in 4 hours, heat up gradually then and drip NaOH solution, Octadecanamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 1.2: 2.4, and then reacted 1.5 hours, stop reaction, obtain yellow supernatant liquid and be Octadecanamide surfactant.
. list of references
[1]MannheimerH.S，John?JM.Surface-avtiveagents[P].Brit.853441，1960.
[2]Wechsler，Joseph?R，Baber，Tomas?G，Battaglini，George?T，et?al.Imidazolines[P].US?4189593，1980.
[3]Phillips?B.M.，Lambie?A.J.，Thompson?M.E.Aliphatic?Amidoamines[P].Brit.UK?Pat.Appl.2003867，1979.
[4]Mannheimer?H.S.Cycloimidine?detivatives[P].US?2773068，1956.
[5]Sano?Y，Miyamoto?M，Kimura?Y，et?al.Zwitterions?of?1-poly(oxyethylene)-2-imidazoline?derivatives?anti-electrostaticagent?for?polyamide?fiber[J].Polym.Ball.(Berlin)，1982，6(5，6)：343～349.
[6]Ploog?U，Retzold?M，Vphues?G.New?imidazolines?and?their?derivatives?from?fatty?acids?and?hydroxyalkylamines[J].Fette，Seifen，Ansrichm.，1980，82(2)：57～59.
[7] Lan Yunjun, Bao Lihong, Li Yan. the type of amphoteric surfactant, application performance and general situation of development. Chinese leather, 2003,32 (13): 20～24
[8] Wang Jun, Ge Hong, Zou Wenyuan. the synthetic route general introduction of amphoteric surfactant. daily chemical industry, 2005,35 (1): 45～48
[9] Liang Menglan. the synthetic and application of amphoteric imidazoline surfactant. Speciality Petrochemicals, 1986,2 (5): 14～27
Claims (2)
1, Octadecanamide surfactant, its structural formula is:
2, the synthetic method of the described Octadecanamide surfactant of claim 1 is characterized in that this method comprises:
Synthetic route:
Building-up process:
The first, the Octadecanamide surfactant intermediate is synthetic
Building-up process:
Mechanical agitation is housed, temperature is taken into account in the four-hole bottle of vacuum distillation apparatus, according to mol ratio is that 1: 1～1.5 ratio adds stearic acid and AEEA, begin heating and stir, slowly reaction temperature is risen to 100 ℃ ± 10 ℃, when starting vavuum pump conditioned reaction system vacuum to water outlet till, in 3-5 hour, make reaction temperature rise to 150 ℃ ± 10 ℃ gradually, complete to water outlet, stop heating, cooling, obtain the Octadecanamide surfactant intermediate, structural formula is:
The second, adopt " chloroactic acid method " to carry out amphoterisation and obtain Octadecanamide surfactant
Building-up process:
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, the Octadecanamide surfactant intermediate heating that the step obtains in the adding is also stirred, between 50～90 ℃ of temperature, low temperature drips chloroacetic acid solution in 4 hours, heat up gradually then and drip NaOH solution, Octadecanamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 1～1.3: 2～2.6, and then reacted 1-2 hour, stop reaction, obtain yellow supernatant liquid and be Octadecanamide surfactant.
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| CN2007101507511A CN101254436B (en) | 2007-12-05 | 2007-12-05 | Octadecanamide surfactant and synthetic method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101972615A (en) * | 2010-10-19 | 2011-02-16 | 中国林业科学研究院林产化学工业研究所 | Glycosyl-contained surface active agent as well as preparation method and measuring method thereof |
| CN102503848A (en) * | 2011-10-28 | 2012-06-20 | 广州花语精细化工有限公司 | Synthesis method of amphoteric sodium acetate surfactant |
-
2007
- 2007-12-05 CN CN2007101507511A patent/CN101254436B/en active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101972615A (en) * | 2010-10-19 | 2011-02-16 | 中国林业科学研究院林产化学工业研究所 | Glycosyl-contained surface active agent as well as preparation method and measuring method thereof |
| CN101972615B (en) * | 2010-10-19 | 2013-01-02 | 中国林业科学研究院林产化学工业研究所 | Glycosyl-contained surface active agent as well as preparation method and measuring method thereof |
| CN102503848A (en) * | 2011-10-28 | 2012-06-20 | 广州花语精细化工有限公司 | Synthesis method of amphoteric sodium acetate surfactant |
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