CN101254440B - Dicarboxy hexadecoic acid acidamide surfactant and synthetic method - Google Patents
Dicarboxy hexadecoic acid acidamide surfactant and synthetic method Download PDFInfo
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- CN101254440B CN101254440B CN200710150755XA CN200710150755A CN101254440B CN 101254440 B CN101254440 B CN 101254440B CN 200710150755X A CN200710150755X A CN 200710150755XA CN 200710150755 A CN200710150755 A CN 200710150755A CN 101254440 B CN101254440 B CN 101254440B
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Abstract
A dicarboxyl hexadecanamide surfactant and a synthetic method thereof are provided. The inventive dicarboxyl hexadecanamide surfactant has the structural formula as 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 hexadecanamide surfactantintermediate from hexadecanoic acid and hydroxyethylethylene diamine as raw materials, and then performing amphoteric reaction by 'chloroacetic acid process' to obtain the dicarboxyl hexadecanamide surfactant, wherein the mole ratio of intermediate to chloroacetic acid to NaOH is 1: (2-2.6):(4-5.2). The inventive dicarboxyl hexadecanamide surfactant has low forming performance and low irritation,and good compounding, washing, wetting and penetrating performance; and can be widely used as a cleaning agent in daily chemical industry, as well as an emulsifier, a dispersant and a industrial surface cleaning agent.
Description
[technical field]: the invention belongs to surfactant and preparing technical field thereof.
[background technology]: Dicarboxy hexadecoic 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 hexadecoic acid acidamide surfactant and synthetic method thereof.
The present invention is on the basis of summing up former achievements, and with hexadecylic 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 hexadecoic acid acidamide surfactant, and its structural formula is:
The synthetic route of Dicarboxy hexadecoic 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 hexadecoic acid acidamide surfactant
With hexadecylic acid and AEEA is raw material, and preparation is used for the intermediate of synthetic Dicarboxy hexadecoic acid acidamide surfactant, concrete steps:
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 hexadecylic 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, cooling, obtain being used for the intermediate of synthetic Dicarboxy hexadecoic acid acidamide surfactant, structural formula is:
For the structure of Dicarboxy hexadecoic 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 hexadecoic acid acidamide 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 hexadecoic 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 gradually then and drip NaOH solution, Dicarboxy hexadecoic 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 hexadecoic acid acidamide surfactant.
Advantage of the present invention and good effect:
The present invention is an acidamide surfactant, has low bubble property, low irritant, and compatibility, washing, wetting, permeance property preferably.
Dicarboxy hexadecoic acid acidamide surfactant provided by the invention is widely used in daily use chemicals industry cleaning agent; And as emulsifying agent, dispersant and industrial surface cleaning 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 hexadecylic acid 153.6g (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 3.5 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 hexadecoic acid acidamide surfactant.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, intermediate 20.6g (0.06mol) heating that is used for synthetic Dicarboxy hexadecoic 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 hexadecoic 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 hexadecoic acid acidamide surfactant.Surface tension σ (20 ℃, 20.00mNm
-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 hexadecylic acid 153.6g (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 hexadecoic acid acidamide surfactant.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, intermediate 20.6g (0.06mol) heating that is used for synthetic Dicarboxy hexadecoic 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 hexadecoic 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 hexadecoic acid acidamide surfactant.
Embodiment 3:
Mechanical agitation is housed, temperature is taken into account in the four-hole bottle of vacuum distillation apparatus, add hexadecylic acid 153.6g (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 hexadecoic acid acidamide surfactant.
In the four-hole bottle that stirring, thermometer, reflux condenser and dropping funel are housed, intermediate 20.6g (0.06mol) heating that is used for synthetic Dicarboxy hexadecoic 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 hexadecoic 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 hexadecoic 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，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 hexadecoic acid acidamide surfactant, it consists of:
2. the synthetic method of the described Dicarboxy hexadecoic 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 hexadecoic 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 hexadecylic acid and AEEA, begin heating and stirring, 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 ℃, complete to water outlet, stop heating, cooling, obtain being used for the intermediate of synthetic Dicarboxy hexadecoic acid acidamide surfactant, it consists of:
C
15H
31CONHCH
2CH
2NHCH
2CH
2OH and
The second, adopt " chloroactic acid method " to carry out amphoterisation and obtain Dicarboxy hexadecoic 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 hexadecoic 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 hexadecoic 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 hexadecoic acid acidamide surfactant.
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Assignee: Tianjin Alta Technology Co. Ltd. Assignor: Tianjin University of Technology Contract record no.: 2012120000033 Denomination of invention: Dicarboxy hexadecoic acid acidamide surfactant and synthetic method Granted publication date: 20100811 License type: Exclusive License Open date: 20080903 Record date: 20120531 |
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Address after: 215000 room 7b, Jinshi building, Shishan Road, high tech Zone, Suzhou, Jiangsu 054 Patentee after: Junhejin (Suzhou) Technology Co.,Ltd. Address before: 300300 revitalization of 5-2-302 in Dongli District, Tianjin Patentee before: Junhe Jin (Tianjin) Technology Co.,Ltd. |
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