CN101041624A - Preparation method of 3- -(P-Nonyl)Phenoxy-2- Hydroxyproyl Trimethyl Ammonium Halide - Google Patents
Preparation method of 3- -(P-Nonyl)Phenoxy-2- Hydroxyproyl Trimethyl Ammonium Halide Download PDFInfo
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- CN101041624A CN101041624A CN 200710014429 CN200710014429A CN101041624A CN 101041624 A CN101041624 A CN 101041624A CN 200710014429 CN200710014429 CN 200710014429 CN 200710014429 A CN200710014429 A CN 200710014429A CN 101041624 A CN101041624 A CN 101041624A
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- trimethyl ammonium
- nonylphenoxy
- ammonium halide
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Abstract
The invention discloses a making method of 3-p-nonylphenoxyacetic-2-hydroxypropyl trimethyl ammonium halides, which comprises the following steps: adopting toluene as catalyst and tetra butyl ammonium chloride as phase-transmitting catalyst in the alkaline condition to react p-nonyl phenol and epichlorohydrin at 70+-1 deg.c for 4-5h; obtaining p-nonylphenyl glycidic ester; dissolving p-nonylphenyl glycidic ester through 95%; adding trimethyl halogen acid at 40+-5 deg.c for 2h-3h; recrystallizing through acetic ester; obtaining the product; improving productivity obviously to purify the product.
Description
Technical field:
The invention belongs to the preparation field of tensio-active agent in colloid and the interfacial chemistry, relate in particular to the preparation method of a kind of new quaternary cationics 3-Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide.
Background technology:
Cats product is succeeded in developing batch process from the thirties, has experienced the time in 30 years, and to the sixties, people have just had bigger progress to the research of cats product.In cationic long-run development process, main developing direction is the research and the application of nitrogenous cationoid tensio-active agent, and wherein, quaternary ammonium salt cationic surfactant is of a great variety, is widely used, and develops rapider.
Quaternary ammonium salt cationic surfactant is owing to have adsorption to the surface that has negative charge, and at surface formation film, so have important use, it also is widely used in fabric softener, static inhibitor, pigment dispersing agent, mines flotation agent and asphalt emulsifier etc. except being used for sterilization.
Important use in view of quaternary ammonium salt cationic surfactant, the kind of researching and developing novel cats product promptly has significance, by retrieval, the report that its surfactivity improves greatly though embedding hydroxypropyl in the molecule of anion surfactant AES is arranged, but in the cats product molecule, embed hydroxypropyl, the quaternary cationics that contains phenyl ring of synthesizing new improves surface-active method and does not but appear in the newspapers to reduce the synthetic cost.
Summary of the invention:
At the deficiencies in the prior art, the purpose of this invention is to provide the preparation method of a kind of new quaternary cationics 3-to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide.
The present invention with to nonyl phenol and epoxy chloropropane as raw material, with the synthetic novel quaternary cationics that contains phenyl ring of a class of phase transfer method, to reduce the synthetic cost, improve surfactivity, the family of cats product is increased the new kind of a class again.
3-of the present invention is as follows to the chemical structure of Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide:
Wherein: X is Cl, Br, one of I.
3-of the present invention comprises the steps: the preparation method of Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
(1) synthesizing nonylphenyl glycidyl ether
In four-hole bottle, add nonyl phenol, toluene, Tetrabutyl amonium bromide stirs and makes its dissolving; Take by weighing NaOH, be dissolved in the distilled water, splash in the four-hole bottle, heat with warm water after stirring 1min～5min, after temperature rises to 50 ℃ ± 1 ℃, drip epoxy chloropropane, 15min～16min adds, and is warming up to 70 ℃ ± 1 ℃ then, 4000～5000 rev/mins of stirring reaction 4h～5h; After reaction finished, product solution cooling was also washed in separating funnel 2～3 times with 50 ℃ warm water, takes out upper organic phase then, is transferred in the Erlenmeyer flask anhydrous sodium sulphate of adding organic phase volume weight 1/10～1/8, dried overnight; Liquid is transferred in the pears type bottle then, distills out toluene and epoxy chloropropane with rotatory evaporator, colourless to nonylphenyl glycidyl ether;
Wherein: in the above-mentioned reaction to nonyl phenol: toluene: sodium hydroxide: epoxy chloropropane: Tetrabutyl amonium bromide is 22～23: 44～45: 4～5: 14～15: 0.3～1 by quality ratio;
(2) 3-synthesizing to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
Above-mentioned synthetic is transferred in the four-hole bottle nonylphenyl glycidyl ether, adds 95% ethanol, add Trimethylamine 99 halogen acid salt solution again, stir, and in 40 ℃ ± 5 ℃ warm water baths, reaction 2h～3h; After reaction finishes, solution is moved in the pears type bottle, evaporate the second alcohol and water with Rotary Evaporators; The propyl carbinol that adds 5～15 times of its volumes again continues rotary evaporation and makes propyl carbinol take remaining moisture content out of, gets the heavy-gravity material, and promptly 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide;
Wherein: in the above-mentioned reaction to nonylphenyl glycidyl ether: the Trimethylamine 99 halate: 95% ethanol is 1: 1.1～1.2: 2～2.7 by quality ratio;
(3) 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide purifying
Above-mentioned heavy-gravity 3-is transferred in the four-hole bottle Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide, the ethyl acetate that adds 3～10 times of its volumes, stir, recrystallization, product is after vacuum-drying, get pure product 3-to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide (be abbreviated as NPX, wherein muriate, bromide and iodide are represented with NPC, NPB and NPI respectively).
Among the preparation method of above-mentioned 3-to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide: step (1) is described to nonyl phenol: toluene: sodium hydroxide: epoxy chloropropane: Tetrabutyl amonium bromide is preferably 22: 44: 4 by quality ratio: 14: 0.3～0.5.
Among the preparation method of above-mentioned 3-to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide: step (2) is described to nonylphenyl glycidyl ether: the Trimethylamine 99 halate: 95% ethanol is preferably 1: 1.1～1.2: 2～2.3 by quality ratio.
Wherein: step (2) is described to nonylphenyl glycidyl ether: the Trimethylamine 99 halate: 95% ethanol most preferably is 1: 1.1: 2 by quality ratio.
Among the preparation method of above-mentioned 3-to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide: the described ethyl acetate optimum amount of step (3) is heavy-gravity 3-5～7 times to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide volume.
The advantage that the present invention had is as follows:
1. use and easily purchase common raw material nonyl phenol and inexpensive epoxy chloropropane, will embed hydroxypropyl in the molecule, thereby improved the surfactivity of common quaternary cationics greatly.
Specifically see Table 1: between the comparable period, some data of the cats product of some other similar are listed in the lump for convenience.
2. the productive rate of institute of the present invention synthetic quaternary cationics is higher, is up to 85% after the purification.
3. synthetic method step of the present invention is simple and direct, the fine control of reaction conditions.
4. product is easy to purify.
Table 1:
| Tensio-active agent | CMC (mmol.L -1) | γ cmc (mN.m -1) |
| NPC NPB NBI C nH 2n+2N(CH 3) 3X n＝12 X＝Cl n＝14 n＝16 n＝10 n＝12 X＝Br n＝14 n＝16 | 5.20 6.61 5.62 16.0 4.00 1.30 61.0 15.0 3.50 0.92 | 27.5 27.9 25.7 40.6 39.5 38.0 37.0 |
Embodiment
Below in conjunction with embodiment content of the present invention is described in further detail, but is not limited only to this.
Raw materials used and reagent of the present invention:
To nonyl phenol (CP); Epoxy chloropropane (AR); Trimethylamine aqueous solution (CP); Sodium hydroxide (AR); Hydrochloric acid (AR); Ethyl acetate (AR); Toluene (AR); 95% ethanol (AR); Tetrabutylammonium chloride (GP); Anhydrous sodium sulphate (CP).
Is that the synthetic route of example is as follows with 3-to Nonylphenoxy-2-hydroxypropyl-trimethyl ammonium chloride:
Embodiment 1
3-comprises the steps: the preparation method of Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
(1) synthesizing nonylphenyl glycidyl ether
In 250 milliliters of four-hole bottles, add 0.1 mole of nonyl phenol (about 22g), toluene 50ml, the about 1g of Tetrabutyl amonium bromide stirs and makes its dissolving; Take by weighing NaOH 0.1mol (4.0g), be dissolved in about 4ml distilled water, splash in the four-hole bottle, heat with warm water after stirring 3min, after temperature rises to 50 ℃ ± 1 ℃, drip 0.2 mole of epoxy chloropropane (about 16ml), 15min～16min adds, be warming up to 70 ℃ ± 1 ℃ then, 5000 rev/mins of vigorous stirring reaction 4h; After reaction finished, product solution cooled off slightly and washs in separating funnel 2～3 times with 50 ℃ warm water, takes out upper organic phase then, was transferred in the Erlenmeyer flask adding anhydrous sodium sulphate 5g, dried overnight; Liquid is transferred in the pears type bottle then, distills out toluene and epoxy chloropropane with rotatory evaporator, colourless to nonylphenyl glycidyl ether 24.7g, yield is 80～90%;
(2) 3-synthesizing to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
Nonylphenyl glycidyl ether 24.7g is transferred to above-mentioned synthetic in the four-hole bottle of 500ml, the ethanol 50ml of adding 95%, be 1: 1.1 amount again by the ratio of glycidyl ether and the quality of Trimethylamine 99 halogen acid salt material, the Trimethylamine 99 halogen acid salt solution that adds 35.2ml, stir, and in 40 ℃ ± 1 ℃ warm water bath, reaction 3h; After reaction finishes, solution is moved in the pears type bottle, evaporate the second alcohol and water with Rotary Evaporators; The propyl carbinol that adds 20ml again continues rotary evaporation and makes propyl carbinol take remaining moisture content out of, gets the heavy-gravity material, and promptly 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide;
(3) 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide purifying
Above-mentioned heavy-gravity 3-is transferred in the four-hole bottle Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide, the ethyl acetate that adds 5 times of its volumes stirs recrystallization, product gets pure product 3-to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide after vacuum-drying.
Embodiment 2
3-comprises the steps: the preparation method of Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
(1) synthesizing nonylphenyl glycidyl ether
In four-hole bottle, add nonyl phenol, toluene, Tetrabutyl amonium bromide stirs and makes its dissolving; Take by weighing NaOH, be dissolved in the distilled water, splash in the four-hole bottle, with the warm water heating, after temperature rises to 50 ℃ ± 1 ℃, drip epoxy chloropropane behind the stirring 2min, 15min～16min adds, and is warming up to 70 ℃ ± 1 ℃ then, 4000 rev/mins of stirring reaction 5h; After reaction finished, product solution cooling was also washed in separating funnel 3 times with 50 ℃ warm water, takes out upper organic phase then, is transferred in the Erlenmeyer flask anhydrous sodium sulphate of adding organic phase volume weight 1/10, dried overnight; Liquid is transferred in the pears type bottle then, distills out toluene and epoxy chloropropane with rotatory evaporator, colourless to nonylphenyl glycidyl ether;
Wherein: in the above-mentioned reaction to nonyl phenol: toluene: sodium hydroxide: epoxy chloropropane: Tetrabutyl amonium bromide is 22: 44: 4 by quality ratio: 14: 0.3;
(2) 3-synthesizing to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
Above-mentioned synthetic is transferred in the four-hole bottle nonylphenyl glycidyl ether, adds 95% ethanol, add Trimethylamine 99 halogen acid salt solution again, stir, and in 45 ℃ of warm water baths, reaction 2h; After reaction finishes, solution is moved in the pears type bottle, evaporate the second alcohol and water with Rotary Evaporators; The propyl carbinol that adds 10 times of its volumes again continues rotary evaporation and makes propyl carbinol take remaining moisture content out of, gets the heavy-gravity material, and promptly 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide;
Wherein: in the above-mentioned reaction to nonylphenyl glycidyl ether: the Trimethylamine 99 halate: 95% ethanol is 1: 1.1: 2 by quality ratio;
(3) 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide purifying
Above-mentioned heavy-gravity 3-is transferred in the four-hole bottle Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide, the ethyl acetate that adds 7 times of its volumes stirs recrystallization, product gets pure product 3-to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide after vacuum-drying.
Embodiment 3
3-comprises the steps: the preparation method of Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
(1) synthesizing nonylphenyl glycidyl ether
In four-hole bottle, add nonyl phenol, toluene, Tetrabutyl amonium bromide stirs and makes its dissolving; Take by weighing NaOH, be dissolved in the distilled water, splash in the four-hole bottle, with the warm water heating, after temperature rises to 50 ℃ ± 1 ℃, drip epoxy chloropropane behind the stirring 5min, 15min～16min adds, and is warming up to 70 ℃ ± 1 ℃ then, 4500 rev/mins of stirring reaction 4.5h; After reaction finished, product solution cooling was also washed in separating funnel 2 times with 50 ℃ warm water, takes out upper organic phase then, is transferred in the Erlenmeyer flask anhydrous sodium sulphate of adding organic phase volume weight 1/9, dried overnight; Liquid is transferred in the pears type bottle then, distills out toluene and epoxy chloropropane with rotatory evaporator, colourless to nonylphenyl glycidyl ether;
Wherein: in the above-mentioned reaction to nonyl phenol: toluene: sodium hydroxide: epoxy chloropropane: Tetrabutyl amonium bromide is 23: 45: 5 by quality ratio: 15: 1;
(2) 3-synthesizing to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
Above-mentioned synthetic is transferred in the four-hole bottle nonylphenyl glycidyl ether, adds 95% ethanol, add Trimethylamine 99 halogen acid salt solution again, stir, and in 40 ℃ ± 2 ℃ warm water baths, reaction 2.5h; After reaction finishes, solution is moved in the pears type bottle, evaporate the second alcohol and water with Rotary Evaporators; The propyl carbinol that adds 8 times of its volumes again continues rotary evaporation and makes propyl carbinol take remaining moisture content out of, gets the heavy-gravity material, and promptly 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide;
Wherein: in the above-mentioned reaction to nonylphenyl glycidyl ether: the Trimethylamine 99 halate: 95% ethanol is 1: 1.2: 2 by quality ratio;
(3) 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide purifying
Above-mentioned heavy-gravity 3-is transferred in the four-hole bottle Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide, the ethyl acetate that adds 3～10 times of its volumes stirs recrystallization, product gets pure product 3-to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide after vacuum-drying.
Embodiment 4
3-comprises the steps: the preparation method of Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
(1) synthesizing nonylphenyl glycidyl ether
In four-hole bottle, add nonyl phenol, toluene, Tetrabutyl amonium bromide stirs and makes its dissolving; Take by weighing NaOH, be dissolved in the distilled water, splash in the four-hole bottle, with the warm water heating, after temperature rises to 50 ℃ ± 1 ℃, drip epoxy chloropropane behind the stirring 1min, 15min～16min adds, and is warming up to 70 ℃ ± 1 ℃ then, 5000 rev/mins of stirring reaction 4h; After reaction finished, product solution cooling was also washed in separating funnel 3 times with 50 ℃ warm water, takes out upper organic phase then, is transferred in the Erlenmeyer flask anhydrous sodium sulphate of adding organic phase volume weight 1/8, dried overnight; Liquid is transferred in the pears type bottle then, distills out toluene and epoxy chloropropane with rotatory evaporator, colourless to nonylphenyl glycidyl ether;
Wherein: in the above-mentioned reaction to nonyl phenol: toluene: sodium hydroxide: epoxy chloropropane: Tetrabutyl amonium bromide is 22: 44: 4 by quality ratio: 14: 0.5;
(2) 3-synthesizing to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
Above-mentioned synthetic is transferred in the four-hole bottle nonylphenyl glycidyl ether, adds 95% ethanol, add Trimethylamine 99 halogen acid salt solution again, stir, and in 40 ℃ ± 3 ℃ warm water baths, reaction 3h; After reaction finishes, solution is moved in the pears type bottle, evaporate the second alcohol and water with Rotary Evaporators; The propyl carbinol that adds 15 times of its volumes again continues rotary evaporation and makes propyl carbinol take remaining moisture content out of, gets the heavy-gravity material, and promptly 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide;
Wherein: in the above-mentioned reaction to nonylphenyl glycidyl ether: the Trimethylamine 99 halate: 95% ethanol is 1: 1.2: 2.7 by quality ratio;
(3) 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide purifying
Above-mentioned heavy-gravity 3-is transferred in the four-hole bottle Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide, the ethyl acetate that adds 3～10 times of its volumes stirs recrystallization, product gets pure product 3-to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide after vacuum-drying.
Claims (5)
1.3-the preparation method to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide comprises the steps:
(1) synthesizing nonylphenyl glycidyl ether
In four-hole bottle, add nonyl phenol, toluene, Tetrabutyl amonium bromide stirs and makes its dissolving; Take by weighing NaOH, be dissolved in the distilled water, splash in the four-hole bottle, heat with warm water after stirring 1min～5min, after temperature rises to 50 ℃ ± 1 ℃, drip epoxy chloropropane, 15min～16min adds, and is warming up to 70 ℃ ± 1 ℃ then, 4000～5000 rev/mins of stirring reaction 4h～5h; After reaction finished, product solution cooling was also washed in separating funnel 2～3 times with 50 ℃ warm water, takes out upper organic phase then, is transferred in the Erlenmeyer flask anhydrous sodium sulphate of adding organic phase volume weight 1/10～1/8, dried overnight; Liquid is transferred in the pears type bottle then, distills out toluene and epoxy chloropropane with rotatory evaporator, colourless to nonylphenyl glycidyl ether;
Wherein: in the above-mentioned reaction to nonyl phenol: toluene: sodium hydroxide: epoxy chloropropane: Tetrabutyl amonium bromide is 22～23: 44～45: 4～5: 14～15: 0.3～1 by quality ratio;
(2) 3-synthesizing to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide
Above-mentioned synthetic is transferred in the four-hole bottle nonylphenyl glycidyl ether, adds 95% ethanol, add Trimethylamine 99 halogen acid salt solution again, stir, and in 40 ℃ ± 5 ℃ warm water baths, reaction 2h～3h; After reaction finishes, solution is moved in the pears type bottle, evaporate the second alcohol and water with Rotary Evaporators; The propyl carbinol that adds 5～15 times of its volumes again continues rotary evaporation and makes propyl carbinol take remaining moisture content out of, gets the heavy-gravity material, and promptly 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide;
Wherein: in the above-mentioned reaction to nonylphenyl glycidyl ether: the Trimethylamine 99 halate: 95% ethanol is 1: 1.1～1.2: 2～2.7 by quality ratio;
(3) 3-is to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide purifying
Above-mentioned heavy-gravity 3-is transferred in the four-hole bottle Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide, the ethyl acetate that adds 3～10 times of its volumes stirs recrystallization, product gets pure product 3-to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide after vacuum-drying.
2. 3-is characterized in that the preparation method of Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide according to claim 1: step (1) is described to nonyl phenol: toluene: sodium hydroxide: epoxy chloropropane: Tetrabutyl amonium bromide is 22: 44: 4 by quality ratio: 14: 0.3～0.5.
3. 3-is characterized in that the preparation method of Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide according to claim 1: step (2) is described to nonylphenyl glycidyl ether: the Trimethylamine 99 halate: 95% ethanol is 1: 1.1～1.2: 2～2.3 by quality ratio.
4. as the preparation method of 3-as described in the claim 3 to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide, it is characterized in that: step (2) is described to nonylphenyl glycidyl ether: the Trimethylamine 99 halate: 95% ethanol is 1: 1.1: 2 by quality ratio.
5. 3-is characterized in that the preparation method of Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide according to claim 1: the described ethyl acetate consumption of step (3) is heavy-gravity 3-5～7 times to Nonylphenoxy-2-Hydroxyproyl Trimethyl Ammonium Halide volume.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102531931A (en) * | 2011-12-07 | 2012-07-04 | 江苏博特新材料有限公司 | Phenol quaternary ammonium salt emulsifier and preparation method thereof |
| WO2015090444A1 (en) * | 2013-12-20 | 2015-06-25 | Basf Coatings Gmbh | Formulations containing pigment and filler |
-
2007
- 2007-04-30 CN CN 200710014429 patent/CN101041624A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102531931A (en) * | 2011-12-07 | 2012-07-04 | 江苏博特新材料有限公司 | Phenol quaternary ammonium salt emulsifier and preparation method thereof |
| WO2015090444A1 (en) * | 2013-12-20 | 2015-06-25 | Basf Coatings Gmbh | Formulations containing pigment and filler |
| US9938417B2 (en) | 2013-12-20 | 2018-04-10 | Basf Coatings Gmbh | Formulations containing pigment and filler |
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