CN100566808C - Dicarboxy oleic acid acidamide surfactant and synthetic method thereof - Google Patents
Dicarboxy oleic acid acidamide surfactant and synthetic method thereof Download PDFInfo
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- CN100566808C CN100566808C CNB2007101507530A CN200710150753A CN100566808C CN 100566808 C CN100566808 C CN 100566808C CN B2007101507530 A CNB2007101507530 A CN B2007101507530A CN 200710150753 A CN200710150753 A CN 200710150753A CN 100566808 C CN100566808 C CN 100566808C
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- oleic acid
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- acidamide surfactant
- acid acidamide
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Abstract
Dicarboxy oleic acid acidamide surfactant and synthetic method thereof.The structural formula of Dicarboxy oleic acid acidamide surfactant provided by the invention is as follows.The inventive method adopts the vacuum-direct synthesizing amide type of amphoterisation method surfactant innovatively without the ring process that reaches a standard.Concrete synthetic method is: at first be to be raw material with oleic acid and AEEA, synthetic Dicarboxy oleic acid acidamide surfactant intermediate, then, adopt " chloroactic acid method " to carry out amphoterisation and obtain Dicarboxy oleic acid acidamide surfactant, wherein the Dicarboxy oleic acid acidamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 2～2.6: 4～5.2.Dicarboxy 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]:
Dicarboxy 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 Dicarboxy capric 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.
Acid amide type surfactant of the present invention is meant Dicarboxy oleic acid acidamide surfactant, and it consists of:
The synthetic route of Dicarboxy oleic acid acidamide surfactant of the present invention is:
Concrete synthetic method is as follows:
The first, be used for the preparation of the intermediate of synthetic Dicarboxy oleic acid acidamide surfactant
With oleic acid and AEEA is raw material, and preparation is used for the intermediate of synthetic Dicarboxy oleic acid acidamide surfactant, and synthetic method is as follows:
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 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, lower the temperature, obtain being used for the intermediate of synthetic Dicarboxy oleic acid acidamide surfactant, consist of:
For the structure of Dicarboxy 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 Dicarboxy oleic acid acidamide surfactant
Synthetic method is as follows:
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, the intermediate heating that is used for synthetic Dicarboxy oleic acid acidamide surfactant that makes more than 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, Dicarboxy oleic acid acidamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 2～2.6: 4～5.2, and then reacted 1-2 hour, stop reaction, obtain yellow supernatant liquid and be Dicarboxy oleic acid acidamide surfactant.
Advantage of the present invention and good effect:
The present invention is an acidamide surfactant, mineral oil and vegetable oil is had the function of better emulsification, dispersion, suspension greasy dirt, and help 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.
Dicarboxy oleic acid acidamide surfactant provided by the invention can be 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, lower the temperature, obtain being used for the intermediate of synthetic Dicarboxy oleic acid acidamide surfactant.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, intermediate 22.2g (0.06mol) heating that is used for synthetic Dicarboxy oleic acid acidamide surfactant that makes more than 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, Dicarboxy oleic acid acidamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 2: 4, and then reacted 1 hour, stop reaction, obtain yellow supernatant liquid and be Dicarboxy oleic acid acidamide surfactant.Surface tension σ (20 ℃, 38.83mNm
-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 4 hours, make reaction temperature rise to 150 ℃ gradually, complete to water outlet.Stop heating, lower the temperature, obtain being used for the intermediate of synthetic Dicarboxy oleic acid acidamide surfactant.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, intermediate 22.2g (0.06mol) heating that is used for synthetic Dicarboxy oleic acid acidamide that makes more than 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, Dicarboxy oleic acid acidamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 2.6: 5.2, and then reacted 1.5 hours, stop reaction, obtain yellow supernatant liquid and be Dicarboxy 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 4.5 hours, make reaction temperature rise to 150 ℃ gradually, complete to water outlet.Stop heating, lower the temperature, obtain being used for the intermediate of synthetic Dicarboxy oleic acid acidamide surfactant.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, intermediate 22.2g (0.06mol) heating that is used for synthetic Dicarboxy oleic acid acidamide surfactant that makes more than 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, Dicarboxy oleic acid acidamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 2.5: 5, and then reacted 1.5 hours, stop reaction, obtain yellow supernatant liquid and be Dicarboxy 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.UKPat.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, Dicarboxy oleic acid acidamide surfactant, it consists of:
2, the synthetic method of the described Dicarboxy oleic acid acidamide surfactant of claim 1 is characterized in that this method comprises:
Synthetic route:
Building-up process:
The first, be used for the preparation of the intermediate of synthetic Dicarboxy oleic acid acidamide surfactant
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 being used for the intermediate of synthetic Dicarboxy oleic acid acidamide surfactant, it consists of:
The second, adopt " chloroactic acid method " to carry out amphoterisation and obtain Dicarboxy oleic acid acidamide surfactant
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, the intermediate that is used for synthetic Dicarboxy oleic acid acidamide surfactant that makes more than the adding, heating is also stirred, between 50～90 ℃ of temperature, low temperature drips chloroacetic acid solution in 4 hours, heat up then and drip NaOH solution, Dicarboxy oleic acid acidamide surfactant intermediate: monoxone: the NaOH mol ratio is 1: 2～2.6: 4～5.2, and then reacted 1-2 hour, stop reaction, obtain yellow supernatant liquid and be Dicarboxy oleic acid acidamide surfactant.
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| CNB2007101507530A CN100566808C (en) | 2007-12-05 | 2007-12-05 | Dicarboxy oleic acid acidamide surfactant and synthetic method thereof |
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| CNB2007101507530A CN100566808C (en) | 2007-12-05 | 2007-12-05 | Dicarboxy oleic acid acidamide surfactant and synthetic method thereof |
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| CN100566808C true CN100566808C (en) | 2009-12-09 |
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| CN101613291B (en) * | 2009-07-31 | 2012-06-27 | 中国石油化工股份有限公司胜利油田分公司采油工艺研究院 | Water-soluble phase-permeable viscosity reducer and preparation 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 |
| CN111234965A (en) * | 2020-01-15 | 2020-06-05 | 东莞市四辉表面处理科技有限公司 | Novel oleic soap for efficient industrial wax removal and preparation method thereof |
| CN113512460B (en) * | 2021-08-13 | 2022-10-21 | 福建科恩优路润滑油有限公司 | Anti-wear clean type vehicle lubricating oil and preparation process thereof |
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