CN103752209A - Cashew nut based amide surfactant and preparation method thereof - Google Patents
Cashew nut based amide surfactant and preparation method thereof Download PDFInfo
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- CN103752209A CN103752209A CN201410031037.0A CN201410031037A CN103752209A CN 103752209 A CN103752209 A CN 103752209A CN 201410031037 A CN201410031037 A CN 201410031037A CN 103752209 A CN103752209 A CN 103752209A
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- cashew nut
- pentadecyl
- hydroxyl
- chlorobenzoyl chloride
- diamine
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- 0 C*c1c(*)cccc1* Chemical compound C*c1c(*)cccc1* 0.000 description 7
- IDRWNQYRZFIRHN-UHFFFAOYSA-N Cc1c(C(Cl)=O)c(O)ccc1 Chemical compound Cc1c(C(Cl)=O)c(O)ccc1 IDRWNQYRZFIRHN-UHFFFAOYSA-N 0.000 description 1
- HCJMNOSIAGSZBM-UHFFFAOYSA-N Cc1c(C(O)=O)c(O)ccc1 Chemical compound Cc1c(C(O)=O)c(O)ccc1 HCJMNOSIAGSZBM-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a cashew nut based amide surfactant and a preparation method thereof. The cashew nut based amide surfactant is prepared by the following steps: (1) carrying out reaction on cashew nut acid and an acylation agent to obtain (2-hydroxy-5-pentadecyl) benzoyl chloride; (2) carrying out reaction on the (2-hydroxy-5-pentadecyl) benzoyl chloride and ethylene oxide, and introducing an ethylene oxide hydrophilic group on hydroxyl to obtain (2-hydroxy ether-5-pentadecyl) benzoyl chloride; and (3) carrying out reaction on the product obtained in the step (2) and diamine to obtain the cashew nut based amide surfactant. The cashew nut based amide surfactant has the action of well lowering the surface tension of a water phase system, does not have cloud points, is excellent in salt resistance, emulsifying performance and detergency ability and can be widely applied to the industry and daily use chemical fields as a detergent, an emulsifier and the like. The preparation method disclosed by the invention is simple in the process, high in the yield and easy to operate.
Description
Technical field
The present invention relates to surfactant field, particularly a kind of cashew nut base acidamide surfactant and preparation method thereof.
Background technology
The sepia liquid of vicidity that squeezes in the shell of cashew nut shell liquid Shi Cong tropical finish section plant cashew nut tree fruit and obtain, by pyrolysis or supercritical carbon dioxide step-down, obtains the cashew nut shell liquid of high yield.Stadeler has reported in natural cashew nut shell liquid containing 90% cashew nut acid and 10% card phenol.Because its source is abundant, cheap, industrial using cashew nut acid decarboxylation obtain anacardol for the synthesis of resin and many industrial circles as raw material.Research and application and development as surfactant aspect start from recent years, and currently reported is almost to take after decarboxylation anacardol to obtain cashew nut phenolic group sulfonate and cashew nut phenolic ether etc. as raw material, and kind and application need to be further developed.
Summary of the invention
The object of the present invention is to provide a kind of cashew nut base acidamide surfactant and preparation method thereof, described this cashew nut base acidamide surfactant and preparation method thereof, the not cashew nut acid of decarboxylation of take in cashew nut shell liquid is raw material, obtains that a kind of surface tension is low, emulsibility, soil release performance and the good cashew nut base acidamide surfactant of biological degradability.
A kind of cashew nut base acidamide surfactant provided by the invention, the general molecular formula of this cashew nut base acidamide surfactant is:
In formula: m is 2-10; N is 3-20.
The method of preparing cashew nut base acidamide surfactant provided by the invention, comprises the steps:
1) cashew nut acid is reacted with acylting agent and obtained (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride;
2) by (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride and reacting ethylene oxide, on hydroxyl, introduce hydrophilic ethylene oxide group, obtain (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride;
3) by 2) product and diamine reactant obtain cashew nut base acidamide surfactant provided by the invention.
Above-mentioned preparation method's step 1), in, acylting agent is any one in phosphorus trichloride, phosphorus pentachloride, thionyl chloride, is preferably thionyl chloride.Unnecessary thionyl chloride is steamed rear decompression distillation and obtain product (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride.In this step, reaction temperature is controlled at 50-80 ℃, and the reaction time is 3-8 hour.Step 2) in, catalyst and (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride are joined in reactor, and employing vacuumizes, inflated with nitrogen, at 130-200 ℃ of temperature, fully stirs, then open reactor and pass into oxirane, polymerization reaction time is 2-10 hour.Catalyst is alkali, and consumption is the 0.1-0.3% of raw material gross mass.Step 3) in, diamines is dropwise joined in (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride, reaction temperature is 1-20 ℃, reaction time 0.5-2 hour.Diamines is ethylenediamine, 1,3-propane diamine, Putriscine, 1,5-pentanediamine, 1,6-hexamethylene diamine, 1,7-heptamethylene diamine, 1,8-octamethylenediamine, 1,9-nonamethylene diamine and 1,10-decamethylene diamine.
Above-mentioned preparation method's step 1)-3) in, the consumption of each reactant is as follows: cashew nut acid is 0.8-1: 0.9-1.2 with the mol ratio of acylting agent; The mol ratio of (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride and oxirane is for O.95-1: 0.9-1.6, the mol ratio of (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride and diamines is 0.95-1.5: 0.9-1.0.
With reactant, select cashew nut acid, thionyl chloride, oxirane, 1,3-propane diamine is example, above-mentioned preparation method's step 1), step 2) and step 3) chemical equation, distinguish as follows:
Cashew nut base acidamide surfactant provided by the invention, has alkyl chain, the hydrophilic ethylene oxide group of two some degree of polymerization and two amido links of two 15 carbon.
Cashew nut base acidamide surfactant provided by the invention, has following feature: have the good capillary effect of reduction aqueous phase system, critical micelle concentration is 2.5 * 10
-4-4.2 * 10
-4mol/L, surface tension is 28.95-35mN/m; There is no cloud point and have an excellent anti-salt property, being less than under the salinity of 10g/L, performance change is very little.Preparation method provided by the invention, technique is simple, and productive rate is high, easy operating.This cashew nut base acidamide surfactant, emulsification and detergency ability are good, can be used as washing agent, emulsifying agent etc. and are used widely in industry and household chemicals field.
The specific embodiment
Below in conjunction with embodiment, the present invention is further illustrated, but the present invention is not limited to following examples.
Embodiment 1
1) acid of 42.26g cashew nut is joined in four-hole bottle, slowly be warmed up to 60 ℃ (2, drip while stirring 21.54g thionyl chloride, dropwise rear reaction 4 hours, decompression distillation after unnecessary thionyl chloride distillation is obtained to 36.01g (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride.2) 36.01g (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride and 8g alkali are joined in reactor, with after vacuumized nitrogen 3 times, being warmed up to 140 ℃ adds 40.10g oxirane fully to stir, polymerisation 4 hours, obtains 41.07g (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride (EO=3).3) in four-hole bottle, add 41.07g (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride, fully stir the lower 6.84g1 of dropping, 3-propane diamine, controls reaction temperature and at 5 ℃, reacts 0.5 hour, purifies and obtains 24.24g cashew nut base acidamide surfactant.The critical micelle concentration of this cashew nut based surfactants is 3.67 * 10
-4mol/L, surface tension is 34.27mN/m.
Embodiment 2
1) acid of 30.17g cashew nut is joined in four-hole bottle, slowly be warmed up to 50 ℃, drip while stirring 11.04g thionyl chloride, dropwise rear reaction 3 hours, decompression distillation after unnecessary thionyl chloride distillation is obtained to 32.76g (2-hydroxyl-4-pentadecyl) chlorobenzoyl chloride.2) 32.76g (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride and 4.13g alkali are joined in reactor, with after vacuumized nitrogen 3 times, being warmed up to 135 ℃ adds 41.26g oxirane fully to stir, polymerisation 3 hours, obtains 51.20g (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride (EO=5).3) in four-hole bottle, add 51.20g (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride, fully stir the lower 5.74g of dropping ethylenediamine, control reaction temperature and at 8 ℃, react 1 hour, purify and obtain 29.42g cashew nut base acidamide surfactant.The critical micelle concentration of this cashew nut based surfactants is 2.77 * 10
-4mol/L, surface tension is 29.26mN/m.
Embodiment 3
1) acid of 34.25g cashew nut is joined in four-hole bottle, slowly be warmed up to 45 ℃, drip while stirring 10.97g thionyl chloride, dropwise rear reaction 5 hours, decompression distillation after unnecessary thionyl chloride distillation is obtained to 35.10g (2-hydroxyl-4-pentadecyl) chlorobenzoyl chloride.2) 35.10g (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride and 4.26g alkali are joined in reactor, with after vacuumized nitrogen 3 times, being warmed up to 145 ℃ adds 43.98g oxirane fully to stir, polymerisation 5 hours, obtains 59.46g (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride (EO=7).3) in four-hole bottle, add 59.46g (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride, fully stir the lower 8.17g1 of dropping, 4-butanediamine, controls reaction temperature and at 10 ℃, reacts 1.5 hours, purifies and obtains 34.59g cashew nut base acidamide surfactant.The critical micelle concentration of this cashew nut based surfactants is 3.56 * 10
-4mol/L, surface tension is 30.15mN/m.
Embodiment 4
1) acid of 33.76g cashew nut is joined in four-hole bottle, slowly be warmed up to 45 ℃, drip while stirring 19.98g phosphorus pentachloride, dropwise rear reaction 4 hours, remove unreacted phosphorus pentachloride, decompression distillation obtains 33.92g (2-hydroxyl-4-pentadecyl) chlorobenzoyl chloride.2) 33.92g (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride and 5.78g alkali are joined in reactor, with after vacuumized nitrogen 3 times, being warmed up to 150 ℃ adds 41.25g oxirane fully to stir, polymerisation 5 hours, obtains 60.37g (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride (EO=7).3) in four-hole bottle, add 60.37g (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride, fully stir the lower 9.08g1 of dropping, 5-pentanediamine, controls reaction temperature and at 8 ℃, reacts 1.5 hours, purifies and obtains 30.25g cashew nut base acidamide surfactant.The critical micelle concentration of this cashew nut based surfactants is 4.02 * 10
-4mol/L, surface tension is 29.46mN/m.
Embodiment 5
1) acid of 32.15g cashew nut is joined in four-hole bottle, slowly be warmed up to 50 ℃, drip while stirring 24.03g phosphorus pentachloride, dropwise rear reaction 6 hours, remove unreacted phosphorus pentachloride, decompression distillation obtains 33.17g (2-hydroxyl-4-pentadecyl) chlorobenzoyl chloride.2) 33.17g (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride and 9.46g alkali are joined in reactor, with after vacuumized nitrogen 3 times, being warmed up to 155 ℃ adds 40.39g oxirane fully to stir, polymerisation 6 hours, obtains 76.23g (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride (EO=9).3) in four-hole bottle, add 76.23g (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride, fully stir the lower 8.34g1 of dropping, 4-butanediamine, controls reaction temperature and at 10 ℃, reacts 1 hour, purifies and obtains 38.78g cashew nut base acidamide surfactant.The critical micelle concentration of this cashew nut based surfactants is 3.76 * 10
-4mol/L, surface tension is 32.17mN/m.
Claims (4)
1. a cashew nut base acidamide surfactant, is characterized in that: have following general structure
In formula: m is 2-10, n is 3-20.
2. the preparation method of cashew nut base acidamide surfactant claimed in claim 1, is characterized in that: take cashew nut acid as the synthetic cashew nut base acidamide surfactant of raw material, comprise the following steps:
1) cashew nut acid is reacted with acylting agent and obtained (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride;
2) by (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride and reacting ethylene oxide, on hydroxyl, introduce hydrophilic ethylene oxide group, obtain (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride;
3) by 2) product and diamine reactant obtain cashew nut base acidamide surfactant provided by the invention;
Described step 1) in, cashew nut acid is 0.8-1: 0.9-1.2 with the mol ratio of acylting agent, and reaction temperature is controlled at 50-80 ℃, and reflux time is 3-8 hour,
Described step 2) in, the mol ratio of (2-hydroxyl-5-pentadecyl) chlorobenzoyl chloride and oxirane is 0.95-1: 0.9-1.6, at 130-200 ℃ of temperature, fully stirs, and the reaction time is 2-10 hour,
Described step 3) in, the mol ratio of (2-hydroxy ether-5-pentadecyl) chlorobenzoyl chloride and diamines is 0.95-1.5: 0.9-1.0, and reaction temperature is 1-20 ℃, reaction time 0.5-2 hour.
3. the preparation method of cashew nut base acidamide surfactant according to claim 2, is characterized in that acylting agent is any one in phosphorus trichloride, phosphorus pentachloride, thionyl chloride, is preferably thionyl chloride.
4. the preparation method of cashew nut base acidamide surfactant according to claim 2, is characterized in that diamines is ethylenediamine, 1,3-propane diamine, Putriscine, 1,5-pentanediamine, 1,6-hexamethylene diamine, 1,7-heptamethylene diamine, 1,8-octamethylenediamine, 1,9-nonamethylene diamine and 1,10-decamethylene diamine.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496842A (en) * | 2014-12-30 | 2015-04-08 | 天津利安隆新材料股份有限公司 | Preparation method of hindered phenol antioxidant 1019 |
| CN105435707A (en) * | 2015-12-16 | 2016-03-30 | 江南大学 | Cationic gemini surfactant with analogue cloud temperature phenomenon, and construction method thereof |
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| WO2004053140A2 (en) * | 2002-12-12 | 2004-06-24 | Jawaharlal Nehru Centre For Advanced Scientific Research | Modulators (inhibitors/activators) of histone acetyltransferases |
| CN101941926A (en) * | 2009-07-09 | 2011-01-12 | 滨州美东树脂有限公司 | Cardanol polyoxyethylene ether ammonium sulfate and preparation method thereof |
| CN102716693A (en) * | 2012-06-26 | 2012-10-10 | 郑州大学 | Cashew base nonionic surfactant and preparation method of cashew base nonionic surfactant |
| KR101234699B1 (en) * | 2010-04-16 | 2013-02-19 | 재단법인 한국건자재시험연구원 | Low temperature curing agent for epoxy resin, and manufacturing method for the same |
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2014
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004053140A2 (en) * | 2002-12-12 | 2004-06-24 | Jawaharlal Nehru Centre For Advanced Scientific Research | Modulators (inhibitors/activators) of histone acetyltransferases |
| CN101941926A (en) * | 2009-07-09 | 2011-01-12 | 滨州美东树脂有限公司 | Cardanol polyoxyethylene ether ammonium sulfate and preparation method thereof |
| KR101234699B1 (en) * | 2010-04-16 | 2013-02-19 | 재단법인 한국건자재시험연구원 | Low temperature curing agent for epoxy resin, and manufacturing method for the same |
| CN102716693A (en) * | 2012-06-26 | 2012-10-10 | 郑州大学 | Cashew base nonionic surfactant and preparation method of cashew base nonionic surfactant |
Non-Patent Citations (1)
| Title |
|---|
| 周雅文等: "生物质腰果酚基表面活性剂研究进展", 《化工新型材料》, vol. 41, no. 11, 30 November 2013 (2013-11-30), pages 10 - 12 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496842A (en) * | 2014-12-30 | 2015-04-08 | 天津利安隆新材料股份有限公司 | Preparation method of hindered phenol antioxidant 1019 |
| CN104496842B (en) * | 2014-12-30 | 2017-01-25 | 天津利安隆新材料股份有限公司 | preparation method of hindered phenol antioxidant 1019 |
| CN105435707A (en) * | 2015-12-16 | 2016-03-30 | 江南大学 | Cationic gemini surfactant with analogue cloud temperature phenomenon, and construction method thereof |
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