CN101254435B - Dicarboxy dodecoic acid amide surfactant and synthetic method - Google Patents
Dicarboxy dodecoic acid amide surfactant and synthetic method Download PDFInfo
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- CN101254435B CN101254435B CN2007101507507A CN200710150750A CN101254435B CN 101254435 B CN101254435 B CN 101254435B CN 2007101507507 A CN2007101507507 A CN 2007101507507A CN 200710150750 A CN200710150750 A CN 200710150750A CN 101254435 B CN101254435 B CN 101254435B
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- acid amide
- amide surfactant
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- dodecoic acid
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Abstract
A dicarboxyl lauric amide surfactant and a synthetic method are provided. The inventive dicarboxyl lauric amide surfactant has the structural formula mentioned above. The synthetic method is novel in the direct synthesis of amide surfactants by vacuum-amphoteric method without ring closing reactions. The method includes the following steps: synthesizing a dicarboxyl lauric amide surfactant intermediate from lauric acid and hydroxyethylethylene diamine as raw materials, and then performing amphoteric reaction by 'chloroacetic acid process' to obtain the dicarboxyl stearic amide surfactant, wherein the mole ratio of dicarboxyl lauric amide intermediate to chloroacetic acid to NaOH is 1: 2-2.6:4-5.2. The inventive dicarboxyl lauric amide surfactant has good foaming performance, low irritation, and excellent compounding, washing, wetting and penetrating performance; and is used in infant and adult shampoos, synthetic fibers, antistatic agents in plastic processing, softening agents like lanolin amidate, dye levelers in textile industry, corrosion inhibitors and foaming agents.
Description
[technical field]: the invention belongs to surfactant and preparing technical field thereof.
[background technology]: Dicarboxy dodecoic acid amide 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 dodecoic acid amide surfactant and synthetic method thereof.
The present invention is on the basis of summing up former achievements, and with laurate, 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 dodecoic acid amide surfactant, and it consists of:
The synthetic route of Dicarboxy dodecoic acid amide 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 dodecoic acid amide surfactant:
With laurate and AEEA is raw material, the synthetic intermediate that is used for synthetic Dicarboxy dodecoic acid amide 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 laurate 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 dodecoic acid amide surfactant, consist of:
For the structure of Dicarboxy dodecoic acid amide 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 dodecoic acid amide surfactant, concrete synthetic method is as follows:
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, the intermediate that is used for synthetic Dicarboxy dodecoic acid amide 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 gradually then and drip NaOH solution, Dicarboxy dodecoic acid amide 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 dodecoic acid amide surfactant.
Advantage of the present invention and good effect:
The present invention is an acidamide surfactant, has high bubble property, low irritant, excellent compatibility, washing, wetting, permeance property.
Dicarboxy dodecoic acid amide surfactant provided by the invention can be used for all kinds of babies and adult's shampoo, synthetic fibers, and the antistatic agent of plastic processing, softening agents such as wool acid amides, the fabric levelling agent, and can be used as corrosion inhibiter, blowing agent etc.
[specific embodiment]:
Embodiment 1:
Mechanical agitation is housed, temperature is taken into account in the four-hole bottle of vacuum distillation apparatus, add laurate 120g (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 dodecoic acid amide surfactant.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, add Dicarboxy dodecoic acid amide surfactant intermediate 17.2g (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, Dicarboxy dodecoic acid amide 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 dodecoic acid amide surfactant.Surface tension σ (20 ℃, 23.81mNm
-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 laurate 120g (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 dodecoic acid amide surfactant.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, add Dicarboxy dodecoic acid amide surfactant intermediate 17.2g (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, Dicarboxy dodecoic acid amide 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 dodecoic acid amide surfactant.
Embodiment 3:
Mechanical agitation is housed, temperature is taken into account in the four-hole bottle of vacuum distillation apparatus, add laurate 120g (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, lower the temperature, obtain being used for the intermediate of synthetic Dicarboxy dodecoic acid amide surfactant.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, add Dicarboxy dodecoic acid amide surfactant intermediate 17.2g (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, Dicarboxy dodecoic acid amide 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 dodecoic acid amide 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，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 dodecoic acid amide surfactant, it consists of:
Described surfactant is to be prepared from through following steps:
The first, be used for the preparation of the intermediate of synthetic Dicarboxy dodecoic acid amide 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 laurate 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, cooling, obtain being used for the intermediate of synthetic Dicarboxy dodecoic acid amide surfactant, it consists of:
The second, adopt " chloroactic acid method " to carry out amphoterisation and obtain Dicarboxy dodecoic acid amide surfactant
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, the intermediate that is used for synthetic Dicarboxy dodecoic acid amide 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 gradually then and drip NaOH solution, Dicarboxy dodecoic acid amide 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 dodecoic acid amide surfactant.
2. the synthetic method of the described Dicarboxy dodecoic acid amide 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 dodecoic acid amide 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 laurate 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, cooling, obtain being used for the intermediate of synthetic Dicarboxy dodecoic acid amide surfactant, it consists of:
The second, adopt " chloroactic acid method " to carry out amphoterisation and obtain Dicarboxy dodecoic acid amide surfactant
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, the intermediate that is used for synthetic Dicarboxy dodecoic acid amide 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 gradually then and drip NaOH solution, Dicarboxy dodecoic acid amide 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 dodecoic acid amide surfactant.
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| CN111517992B (en) * | 2020-05-28 | 2021-10-01 | 陕西科技大学 | Symmetrical long-chain carboxyl surfactant and preparation method and application thereof |
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| 孙立成等.咪唑啉型两性表面活性剂的研究---烷基咪唑啉的两性化及产品的物化性能.精细化工5 3.1988,5(3),第1-5页. |
| 孙立成等.咪唑啉型两性表面活性剂的研究——烷基咪唑啉的两性化及产品的物化性能.精细化工5 3.1988,5(3),第1-5页. * |
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