CN100566807C - Oleic acid acidamide surfactant and synthetic method thereof - Google Patents
Oleic acid acidamide surfactant and synthetic method thereof Download PDFInfo
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- CN100566807C CN100566807C CNB2007101507526A CN200710150752A CN100566807C CN 100566807 C CN100566807 C CN 100566807C CN B2007101507526 A CNB2007101507526 A CN B2007101507526A CN 200710150752 A CN200710150752 A CN 200710150752A CN 100566807 C CN100566807 C CN 100566807C
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- oleic acid
- acidamide surfactant
- surfactant
- acid acidamide
- oil
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Abstract
Oleic acid acidamide surfactant and synthetic method thereof.The structural formula of oleic acid acidamide surfactant of the present invention is as follows.Synthetic method of the present invention is: be raw material with oleic acid and AEEA at first, synthetic oleic acid acidamide surfactant intermediate adopts " chloroactic acid method " to carry out amphoterisation then and obtains oleic acid acidamide surfactant.The present invention without the ring process that reaches a standard, adopts the vacuum-direct synthesizing amide type of amphoterisation method surfactant innovatively on the basis of summing up former achievements.Oleic acid acidamide surfactant provided by the invention has the function of better emulsification, dispersion, suspension greasy dirt to mineral oil and vegetable oil, and helps to stop the deposition again of greasy dirt, and metals such as iron and steel, cast iron are had good rustless property.It can promote the stability of anion and non-ionic emulsion and the lubricating capacity of oil emulsion in addition.Can be widely used in metal cleaner, boring oil, cutting oil, products such as the heavy crude thinner in the oil exploitation.
Description
[technical field]:
The invention belongs to surfactant and preparing technical field thereof.
[background technology]:
Oleic acid acidamide 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 Adolf Schmitz 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 oleic acid acidamide surfactant and synthetic method thereof.
The present invention is on the basis of summing up former achievements, and with oleic 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.
Oleic acid acidamide surfactant of the present invention, it consists of:
The synthetic route of oleic acid acidamide surfactant of the present invention is:
Concrete synthetic method is as follows:
The first, the oleic acid acidamide surfactant intermediate is synthetic:
With oleic acid and AEEA is raw material, synthetic oleic acid acidamide 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 oleic 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 oleic acid acidamide surfactant intermediate, consists of:
For the structure of oleic acid acidamide 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 oleic acid acidamide 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 oleic acid acidamide 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, oleic acid acidamide 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 oleic acid acidamide surfactant.
Advantage of the present invention and good effect:
The present invention is an acidamide surfactant, and it has the function of better emulsification, dispersion, suspension greasy dirt to mineral oil and vegetable oil, and helps to stop the deposition again of greasy dirt, and metals such as iron and steel, cast iron are had good rustless property.It can promote the stability of anion and non-ionic emulsion and the lubricating capacity of oil emulsion in addition.
Oleic acid acidamide surfactant provided by the invention is widely used in metal cleaner, boring oil, cutting oil, products such as the heavy crude thinner in the oil exploitation.
[specific embodiment]:
Embodiment 1:
Mechanical agitation is housed, temperature is taken into account in the four-hole bottle of vacuum distillation apparatus, add oleic acid 173.0g (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 oleic acid acidamide surfactant intermediate.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, add oleic acid acidamide surfactant intermediate 22.2g (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, oleic acid acidamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 1: 2, and then reacts 1 hour, stop reaction, obtain yellow supernatant liquid and be oleic acid acidamide surfactant.Surface tension σ (20 ℃, 41.64mNm
-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 oleic acid 173.0g (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 3.5 hours, make reaction temperature rise to 150 ℃ gradually, complete to water outlet.Stop heating, cooling obtains the oleic acid acidamide surfactant intermediate.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, add oleic acid acidamide surfactant intermediate 22.2g (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, oleic acid acidamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 1.3: 2.6, and then reacts 1.5 hours, stop reaction, obtain yellow supernatant liquid and be oleic acid acidamide surfactant.
Embodiment 3:
Mechanical agitation is housed, temperature is taken into account in the four-hole bottle of vacuum distillation apparatus, add oleic acid 173.0g (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 4 hours, make reaction temperature rise to 150 ℃ gradually, complete to water outlet.Stop heating, cooling obtains the oleic acid acidamide surfactant intermediate.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, add oleic acid acidamide surfactant intermediate 22.2g (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, oleic acid acidamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 1.2: 2.4, and then reacts 1.5 hours, stop reaction, obtain yellow supernatant liquid and be oleic acid acidamide surfactant.
List of references
[1]Mannheimer?H.S，John?JM.Surface-avtive?agents[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，MiyamotoM，Kimura?Y，et?al.Zwitterions?of?1-poly(oxyethylene)-2-imidazolinederivativesanti-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, oleic acid acidamide surfactant, it consists of:
2, the synthetic method of the described oleic acid acidamide surfactant of claim 1 is characterized in that this method comprises:
Synthetic route:
Building-up process:
The first, the oleic acid acidamide 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 oleic acid and AEEA, begin heating and stir, 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 ℃, complete to water outlet, stop heating, cooling, obtain the oleic acid acidamide surfactant intermediate, it consists of:
The second, adopt " chloroactic acid method " to carry out amphoterisation and obtain oleic acid acidamide surfactant
Building-up process:
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, the oleic acid acidamide 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 then and drip NaOH solution, oleic acid acidamide 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 oleic acid acidamide surfactant.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2007101507526A CN100566807C (en) | 2007-12-05 | 2007-12-05 | Oleic acid acidamide surfactant and synthetic method thereof |
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| CN100566807C true CN100566807C (en) | 2009-12-09 |
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| 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 |
| CN109504355A (en) * | 2019-01-14 | 2019-03-22 | 天津市海罗兰科技发展股份有限公司 | Highly-efficient lubricant for drilling fluid and its preparation method and application |
| CN110746953B (en) * | 2019-11-07 | 2022-05-10 | 西安石油大学 | Viscosity-reducing and asphalt-stabilizing agent for thickened oil and preparation method thereof |
| CN111363523A (en) * | 2020-03-16 | 2020-07-03 | 中国石油天然气集团有限公司 | Viscosity reducing cutting agent for oil-based drilling fluid, preparation method thereof and method for improving fluidity |
| CN112940873B (en) * | 2021-01-14 | 2022-07-12 | 浙江传化华洋化工有限公司 | Stripping agent kit for removing deposits on edge of drying cylinder for papermaking, use method and stripping agent |
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