CN114989030B - Preparation method of N-lauroyl sarcosine sodium - Google Patents
Preparation method of N-lauroyl sarcosine sodium Download PDFInfo
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- CN114989030B CN114989030B CN202210797984.5A CN202210797984A CN114989030B CN 114989030 B CN114989030 B CN 114989030B CN 202210797984 A CN202210797984 A CN 202210797984A CN 114989030 B CN114989030 B CN 114989030B
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- methyl laurate
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- 108700004121 sarkosyl Proteins 0.000 title claims abstract description 37
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 title claims abstract description 32
- 239000011734 sodium Substances 0.000 title claims abstract description 32
- 229910052708 sodium Inorganic materials 0.000 title claims abstract description 32
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 109
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 99
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 claims abstract description 88
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims abstract description 48
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 38
- 108010077895 Sarcosine Proteins 0.000 claims abstract description 25
- 239000005639 Lauric acid Substances 0.000 claims abstract description 24
- 229940048098 sodium sarcosinate Drugs 0.000 claims abstract description 23
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 claims abstract description 18
- JXHZRQHZVYDRGX-UHFFFAOYSA-M sodium;hydrogen sulfate;hydrate Chemical compound [OH-].[Na+].OS(O)(=O)=O JXHZRQHZVYDRGX-UHFFFAOYSA-M 0.000 claims abstract description 17
- 238000006482 condensation reaction Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 7
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 30
- 239000003054 catalyst Substances 0.000 abstract description 17
- 238000000034 method Methods 0.000 abstract description 17
- 239000013067 intermediate product Substances 0.000 abstract description 15
- 238000007086 side reaction Methods 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000000344 soap Substances 0.000 abstract description 5
- 229910017053 inorganic salt Inorganic materials 0.000 abstract description 4
- 231100000331 toxic Toxicity 0.000 abstract description 4
- 230000002588 toxic effect Effects 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 20
- 238000003756 stirring Methods 0.000 description 17
- 239000007795 chemical reaction product Substances 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 235000011187 glycerol Nutrition 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229910021536 Zeolite Inorganic materials 0.000 description 7
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000010457 zeolite Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002190 fatty acyls Chemical group 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 229940043230 sarcosine Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RMJNSNPPAZENDA-UHFFFAOYSA-M C(C)(=O)[O-].[Na+].C(CCCCCCCCCCC)(=O)NC Chemical compound C(C)(=O)[O-].[Na+].C(CCCCCCCCCCC)(=O)NC RMJNSNPPAZENDA-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of N-lauroyl sarcosine sodium, which takes lauric acid and methanol as raw materials, sodium bisulfate monohydrate as a catalyst to prepare an intermediate product methyl laurate, does not need to add a solvent, avoids using extremely toxic reaction materials, and has mild reaction conditions and less side reaction; the intermediate product is subjected to condensation reaction with sodium sarcosinate and sodium methoxide serving as a catalyst to obtain the product N-lauroyl sodium sarcosinate, no inorganic salt is generated in the whole reaction process, the soap content in the product is reduced, the possibility of side reaction is reduced, the yield and purity of the product are high, the yield of each step reaches about 90%, the viscosity of a reaction system is moderate, the difficulty of a post-treatment process is reduced, and the current situation that the reaction rate is greatly reduced due to overlarge viscosity in the reaction process is overcome; the whole reaction process only needs two steps, the reaction condition is mild, the reaction steps are few, and the preparation method is simple.
Description
Technical Field
The invention belongs to the technical field of surfactants, and particularly relates to a preparation method of N-lauroyl sarcosine sodium.
Background
N-lauroyl sarcosine sodium is also called lauroyl methylamine sodium acetate, is a good scale remover and foaming agent, can be used as the foaming agent of cosmetics and toothpaste, has small irritation to skin, is used as a detergent, has weak degreasing property and is valued.
Both Chinese patent CN 113651714A and CN 111333531A report the preparation method of N-lauroyl sarcosine sodium, but both patents use fatty acyl chloride as reaction raw materials, a large amount of NaCl cannot be introduced into the product, accumulation of NaCl in the later period of the reaction and increase of the concentration of a surfactant cause the viscosity increase in the whole later period of the reaction, and the N-lauroyl sarcosine sodium has excellent foaming performance, so that mass transfer and heat transfer in the whole later period of the reaction are difficult comprehensively caused, thereby further increasing the hydrolysis probability of the fatty acyl chloride, increasing the soap content in the product and reducing the yield. Meanwhile, the phosphorus trichloride and thionyl chloride are used, so that the pollution caused by the reaction is also relatively large.
Therefore, a new preparation method is needed, the yield is continuously improved, the difficulty of post-treatment is reduced, and the pollution of the reaction is minimized.
Disclosure of Invention
The invention aims to provide a preparation method of N-lauroyl sodium sarcosinate, which takes lauric acid and methanol as raw materials, sodium bisulfate monohydrate as a catalyst to prepare an intermediate product methyl laurate, and then the intermediate product methyl laurate is subjected to condensation reaction with sodium sarcosinate and sodium methoxide as a catalyst to obtain the product N-lauroyl sodium sarcosinate, so that the use of extremely toxic reaction materials is avoided, the reaction condition is mild, no inorganic salt is generated in the whole reaction process, the soap content in the product is reduced, the possibility of side reaction is reduced, the yield and purity of the product are high, the yield of each step reaches about 90 percent, the viscosity of a reaction system is moderate, the difficulty of a post-treatment process is reduced, and the current situation that the reaction rate is greatly reduced due to overlarge viscosity in the reaction process is overcome.
The technical scheme of the invention is as follows:
The preparation process of N-lauroyl sarcosine sodium includes the following steps:
(1) Uniformly mixing lauric acid, methanol and sodium bisulfate monohydrate, and then reacting at 75-85 ℃ to prepare methyl laurate;
(2) Under the protection of nitrogen, carrying out condensation reaction on methyl laurate, sodium sarcosinate and sodium methoxide prepared in the step (1) at the temperature of 130-140 ℃ to prepare N-lauroyl sodium sarcosinate;
the specific synthetic route is as follows:
In the step (1), when methyl laurate is prepared from lauric acid and methanol, the reaction temperature needs to be strictly controlled, and the reaction temperature is too low, so that the reaction is incomplete, the smooth progress of the reaction is not facilitated, and the yield of an intermediate product is low; the reaction temperature is too high, side reactions are easy to occur, and the yield and purity of the intermediate product are reduced. For the present invention, the reaction temperature is 75 to 85℃and may be, but not limited to, 75℃78 ℃,80 ℃, 82 ℃, 85 ℃, 88 ℃ or 90℃and, for a better effect, 80 ℃.
Further, the reaction time is 4 to 10 hours, which may be, but is not limited to, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours or 10 hours, preferably 5 hours.
In the process of preparing methyl laurate from lauric acid and methanol in the step (1), even if the reaction temperature during the reaction is strictly controlled, the addition amount of methanol needs to be strictly controlled, and too high or too low can reduce the yield and purity of the intermediate product methyl laurate. Specifically, the molar ratio of lauric acid to methanol is 1:8-10, and can be, but is not limited to, 1:8, 1:8.2, 1:8.5, 1:8.7, 1:9, 1:9.2, 1:9.5, 1:9.7 or 1:10, preferably, the molar ratio of lauric acid to methanol is 1:8.5-9.5; more preferably, the molar ratio of lauric acid to methanol is 1:9.
In the process of preparing methyl laurate from lauric acid and methanol in the step (1), even if the reaction temperature and the addition amount of methanol in the reaction process are strictly controlled, the addition amount of sodium bisulfate monohydrate serving as a catalyst needs to be strictly controlled, and the addition amount is lower, so that the smooth progress of the reaction is not facilitated, and the yield of an intermediate product is lower; the addition amount is higher, other side reactions are easy to catalyze, so that the content of byproducts is higher, and the yield and purity of the intermediate product are reduced. Specifically, the molar ratio of lauric acid to sodium bisulfate monohydrate is 1:0.1 to 0.2, and may be, but is not limited to, 1:0.1, 1:0.11, 1:0.12, 1:0.13, 1:0.14, 1:0.15, 1:0.1, 1:0.17, 1:0.18, 1:0.19 or 1:0.2, preferably, the molar ratio of lauric acid to sodium bisulfate monohydrate is 1:0.13 to 0.17, more preferably, the molar ratio of lauric acid to sodium bisulfate monohydrate is 1:0.15.
In the step (1), a water separator is arranged in the reaction process, so that the water in the reaction process is reduced.
In the step (1), methanol is used as a raw material in the process of preparing the intermediate product methyl laurate, a solvent is not required to be added, so that the use of extremely toxic reaction materials is avoided, the reaction condition is mild, the side reaction is less, the yield and the purity are high, the harm to human and the environment is less, and the method is suitable for industrialized scale-up production.
In the step (2), methyl laurate is used as a reaction material, and in the process of preparing N-lauroyl sarcosine sodium, the reaction temperature needs to be strictly controlled, and is too low, so that the reaction is incomplete, the smooth progress of the reaction is not facilitated, and the yield of an intermediate product is low; the reaction temperature is too high, side reactions are easy to occur, and the yield and purity of the intermediate product are reduced. For the present invention, the reaction temperature is 130 to 140℃and may be, but not limited to 130℃132℃135℃137℃or 140℃and 135℃for better effect.
Further, the reaction time is 3 to 8 hours, and may be, but not limited to, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours or 8 hours, preferably 4 hours.
In the process of preparing the product N-lauroyl sarcosine sodium from methyl laurate in the step (2), even if the reaction temperature in the reaction process is strictly controlled, the addition amount of the sarcosine sodium needs to be strictly controlled, and the yield and purity of the product N-lauroyl sarcosine sodium can be reduced when the addition amount of the sarcosine sodium is too high or too low. Specifically, the molar ratio of methyl laurate to sodium sarcosinate is 1:2.3-2.8, which can be, but is not limited to, 1:2.3, 1:2.4, 1:2.5, 1:2.6, 1:2.7 or 1:2.8, preferably, the molar ratio of methyl laurate to sodium sarcosinate is 1:2.5.
In the step (2), during the process of preparing the product N-lauroyl sarcosine sodium from methyl laurate, a specific catalyst is required to be selected so as to improve the yield and purity of the product N-lauroyl sarcosine sodium. In the experimental process of exploring the catalyst, the application discovers that the sodium methoxide is adopted as the catalyst, and the adding amount of the sodium methoxide is strictly controlled, so that the reaction rate can be improved, the possibility of side reaction is reduced, the yield and purity of the product are high, and the yield is more than 90%. And other similar catalysts, such as calcium oxide, sodium hydroxide and potassium hydroxide, are adopted, and under the same reaction conditions, the yield and purity of the product N-lauroyl sarcosine sodium are lower.
Even if sodium methoxide is selected as the catalyst in step (2), the amount of sodium methoxide to be added needs to be strictly controlled. The addition amount is low, which is unfavorable for the smooth progress of the reaction, resulting in low yield of the product; the addition amount is higher, other side reactions are easy to catalyze, the content of byproducts is higher, and the yield and purity of the product are reduced. Specifically, the molar ratio of methyl laurate to sodium methoxide is 1:0.015-0.025, which may be, but is not limited to, 1:0.015, 1:0.016, 1:0.017, 1:0.018, 1:0.019, 1:0.02, 1:0.021, 1:0.022, 1:0.023, 1:0.024 or 1:0.025, preferably, the molar ratio of methyl laurate to sodium methoxide is 1:0.02.
In the step (2), in the process of preparing the product N-lauroyl sarcosine sodium from methyl laurate, no inorganic salt is generated in the whole reaction process, so that the soap content in the product is reduced, the possibility of side reaction is reduced, the yield and purity of the product are high, and the yield of each step reaches about 90 percent.
Further, methyl laurate is used as an intermediate product, and in the process of preparing N-lauroyl sarcosine sodium, the viscosity of a reaction system is moderate, so that the difficulty of a post-treatment process is reduced, and the current situation that the reaction rate is greatly reduced due to overlarge viscosity in the reaction process is overcome.
By adopting the technical scheme of the invention, the advantages are as follows:
(1) In the process of preparing the intermediate product methyl laurate, methanol is used as a raw material, a solvent is not required to be added, the use of extremely toxic reaction materials is avoided, the reaction condition is mild, the side reaction is less, the harm to human and environment is less, and the method is suitable for industrial large-scale production.
(2) No inorganic salt is generated in the whole reaction process, so that the soap content in the product is reduced, the possibility of side reaction is reduced, the yield and purity of the product are high, and the yield of each step reaches about 90%.
(3) In the process of preparing N-lauroyl sarcosine sodium by taking methyl laurate as an intermediate product, the viscosity of a reaction system is moderate, the difficulty of the post-treatment process is reduced, and the current situation that the reaction rate is greatly reduced due to overlarge viscosity in the reaction process is overcome.
(4) The whole reaction process only needs two steps, the reaction condition is mild, the reaction steps are few, and the preparation method is simple.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of N-lauroyl sarcosine sodium which is the product of example 1.
FIG. 2 is a MS spectrum of the product N-lauroyl sarcosine sodium in example 1.
Detailed Description
The present invention will be described in further detail by way of examples, which are illustrative of the present invention and are not intended to limit the present invention thereto.
EXAMPLE 1 preparation of sodium N-lauroyl sarcosinate
(1) Preparation of methyl laurate:
In a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1 mol) of lauric acid, 36ml (0.9 mol) of absolute methanol and 2.07g (0.015 mol) of sodium bisulfate monohydrate were charged as catalysts, and after sufficiently stirring uniformly, zeolite was added, and the mixture was charged with a water separator and heated in a water bath at 80℃for reaction for 5 hours. After the reaction, the organic layers were combined, left to stand, the reaction solution was poured out, the reaction solution was distilled at normal pressure, washed once with water, neutralized to neutrality with an aqueous sodium carbonate solution, washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to give 19.28g of colorless transparent liquid in 89.95% yield.
(2) Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1 mol) of methyl laurate, 27.75g (0.25 mol) of sodium sarcosinate, 92g (1 mol) of glycerol and 0.108g (0.002 mol) of sodium methoxide prepared in the step (1) were charged into a four-necked flask equipped with a mechanical stirrer, a thermometer, a bulb-shaped condenser and a water separator, and after stirring uniformly, the temperature was raised to 135℃and the reaction was stirred under nitrogen for 4 hours. After the reaction, ethyl acetate was added to the obtained reaction mixture to extract an upper white solid, which was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 27.09g of a pale yellow solid, with a yield of 92.34%.
Comparative example 1
Preparation of methyl laurate:
In a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1 mol) of lauric acid, 20ml (0.5 mol) of absolute methanol and 2.07g (0.015 mol) of sodium bisulfate monohydrate were charged as catalysts, and after sufficiently stirring uniformly, zeolite was added, and the mixture was charged with a water separator and heated in a water bath at 80℃for reaction for 5 hours. After the reaction, the organic layers were combined, left to stand, the reaction solution was poured out, the reaction solution was distilled at normal pressure, washed once with water, neutralized to neutrality with an aqueous sodium carbonate solution, washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to give 7.89g of a colorless transparent liquid with a yield of 36.81%.
Comparative example 2
Preparation of methyl laurate:
In a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1 mol) of lauric acid, 61ml (1.5 mol) of absolute methanol and 2.07g (0.015 mol) of sodium bisulfate monohydrate were charged as catalysts, and after sufficiently stirring uniformly, zeolite was added, and the mixture was charged with a water separator and heated in a water bath at 80℃for reaction for 5 hours. After the reaction, the organic layers were combined, left to stand, the reaction solution was poured out, the reaction solution was distilled at normal pressure, washed once with water, neutralized to neutrality with an aqueous sodium carbonate solution, washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to give 14.28g of colorless transparent liquid in a yield of 66.62%.
Comparative example 3
Preparation of methyl laurate:
In a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1 mol) of lauric acid, 36ml (0.9 mol) of absolute methanol and 0.69g (0.005 mol) of sodium bisulfate monohydrate were charged as catalysts, and after sufficiently stirring uniformly, zeolite was added, and the mixture was charged with a water separator to heat it in a water bath at 80℃for reaction for 5 hours. After the reaction, the organic layers were combined, left to stand, the reaction solution was poured out, the reaction solution was distilled at normal pressure, washed once with water, neutralized to neutrality with an aqueous sodium carbonate solution, washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to give 11.22g of a colorless transparent liquid in a yield of 52.35%.
Comparative example 4
Preparation of methyl laurate:
In a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1 mol) of lauric acid, 36ml (0.9 mol) of absolute methanol and 4.14g (0.03 mol) of sodium bisulfate monohydrate were charged as catalysts, and after sufficiently stirring uniformly, zeolite was added, and the mixture was charged with a water separator and heated in a water bath at 80℃for reaction for 5 hours. After the reaction, the organic layers were combined, left to stand, the reaction solution was poured out, the reaction solution was distilled at normal pressure, washed once with water, neutralized to neutrality with an aqueous sodium carbonate solution, washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to give 13.58g of a colorless transparent liquid with a yield of 63.36%.
Comparative example 5
Preparation of methyl laurate:
in a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1 mol) of lauric acid, 36ml (0.9 mol) of absolute methanol and 2.07g (0.015 mol) of sodium bisulfate monohydrate were charged as catalysts, and after sufficiently stirring uniformly, zeolite was added, and the mixture was charged with a water separator and heated in a water bath at 70℃for reaction for 5 hours. After the reaction, the organic layers were combined, left to stand, the reaction solution was poured out, the reaction solution was distilled at normal pressure, washed once with water, neutralized to neutrality with an aqueous sodium carbonate solution, washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to give 16.22g of a colorless transparent liquid in a yield of 75.67%.
Comparative example 6
Preparation of methyl laurate:
In a four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a spherical condenser, 20.4g (0.1 mol) of lauric acid, 36ml (0.9 mol) of absolute methanol and 2.07g (0.015 mol) of sodium bisulfate monohydrate were charged as catalysts, and after sufficiently stirring uniformly, zeolite was added, and the mixture was charged with a water separator and heated in a water bath at 90℃for reaction for 5 hours. After the reaction, the organic layers were combined, left to stand, the reaction solution was poured out, the reaction solution was distilled at normal pressure, washed once with water, neutralized to neutrality with an aqueous sodium carbonate solution, washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and the washed product was distilled under reduced pressure to give 15.89g of a colorless transparent liquid in a yield of 74.13%.
Comparative example 7
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1 mol) of methyl laurate, 16.65g (0.15 mol) of sodium sarcosinate, 92g (1 mol) of glycerol and 0.108g (0.002 mol) of sodium methoxide prepared in the step (1) were charged into a four-necked flask equipped with a mechanical stirrer, a thermometer, a bulb-shaped condenser and a water separator, and after stirring uniformly, the temperature was raised to 135℃and the reaction was stirred under nitrogen for 4 hours. After the reaction, ethyl acetate was added to the obtained reaction mixture to extract an upper white solid, which was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 16.32g of a pale yellow solid, with a yield of 55.63%.
Comparative example 8
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1 mol) of methyl laurate, 38.85g (0.35 mol) of sodium sarcosinate, 92g (1 mol) of glycerol and 0.108g (0.002 mol) of sodium methoxide prepared in the step (1) were charged into a four-necked flask equipped with a mechanical stirrer, a thermometer, a bulb-shaped condenser and a water separator, and after stirring uniformly, the temperature was raised to 135℃and the reaction was stirred under nitrogen for 4 hours. After the reaction, ethyl acetate is added into the obtained reaction liquid to extract the upper white solid, the reaction liquid is concentrated under reduced pressure to obtain a crude reaction product, and the crude reaction product is recrystallized by absolute methanol to obtain 20.89g of pale yellow solid, and the yield is 71.20%.
Comparative example 9
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1 mol) of methyl laurate, 27.75g (0.25 mol) of sodium sarcosinate, 92g (1 mol) of glycerol and 0.108g (0.002 mol) of sodium methoxide prepared in the step (1) were charged into a four-necked flask equipped with a mechanical stirrer, a thermometer, a bulb-shaped condenser and a water separator, and after stirring uniformly, the temperature was raised to 120℃and the reaction was stirred under nitrogen for 4 hours. After the reaction, ethyl acetate was added to the obtained reaction mixture to extract an upper white solid, which was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 21.22g of a pale yellow solid, with a yield of 72.33%.
Comparative example 10
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1 mol) of methyl laurate, 27.75g (0.25 mol) of sodium sarcosinate, 92g (1 mol) of glycerin and 0.108g (0.002 mol) of sodium methoxide prepared in the step (1) were charged into a four-necked flask equipped with a mechanical stirrer, a thermometer, a bulb-shaped condenser and a water separator, and after stirring uniformly, the temperature was raised to 150℃and the reaction was stirred under nitrogen for 4 hours. After the reaction, ethyl acetate is added into the obtained reaction liquid to extract the upper white solid, the reaction liquid is concentrated under reduced pressure to obtain a crude reaction product, and the crude reaction product is recrystallized by absolute methanol to obtain 20.26g of pale yellow solid, and the yield is 69.06%.
Comparative example 11
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1 mol) of methyl laurate, 27.75g (0.25 mol) of sodium sarcosinate, 92g (1 mol) of glycerin and 0.112g (0.002 mol) of calcium oxide prepared in the step (1) were added to a four-necked flask equipped with a mechanical stirrer, a thermometer, a bulb-shaped condenser and a water separator, and after stirring uniformly, the temperature was raised to 135℃and the reaction was stirred under nitrogen for 4 hours. After the reaction, ethyl acetate was added to the obtained reaction mixture to extract an upper white solid, the mixture was concentrated under reduced pressure to obtain a crude reaction product, and the crude reaction product was recrystallized from anhydrous methanol to obtain 18.45g of a pale yellow solid, with a yield of 62.89%.
Comparative example 12
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1 mol) of methyl laurate, 27.75g (0.25 mol) of sodium sarcosinate, 92g (1 mol) of glycerol and 0.08g (0.002 mol) of sodium hydroxide prepared in the step (1) were added to a four-necked flask equipped with a mechanical stirrer, a thermometer, a bulb-shaped condenser and a water separator, and after stirring uniformly, the temperature was raised to 135℃and the reaction was stirred under nitrogen for 4 hours. After the reaction, ethyl acetate was added to the obtained reaction solution to extract an upper white solid, the mixture was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from anhydrous methanol to obtain 23.46g of a pale yellow solid, and the yield was 79.96%.
Comparative example 13
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1 mol) of methyl laurate, 27.75g (0.25 mol) of sodium sarcosinate, 92g (1 mol) of glycerin and 0.12g (0.002 mol) of potassium hydroxide prepared in the step (1) were added to a four-necked flask equipped with a mechanical stirrer, a thermometer, a bulb-shaped condenser and a water separator, and after stirring uniformly, the temperature was raised to 135℃and the reaction was stirred under nitrogen for 4 hours. After the reaction, ethyl acetate was added to the obtained reaction solution to extract an upper white solid, the mixture was concentrated under reduced pressure to obtain a crude reaction product, and the crude reaction product was recrystallized from anhydrous methanol to obtain 21.53g of a pale yellow solid, with a yield of 73.39%.
Comparative example 14
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1 mol) of methyl laurate, 27.75g (0.25 mol) of sodium sarcosinate, 92g (1 mol) of glycerol and 0.054g (0.001 mol) of sodium methoxide prepared in the step (1) were charged into a four-necked flask equipped with a mechanical stirrer, a thermometer, a bulb-shaped condenser and a water separator, and after stirring uniformly, the temperature was raised to 135℃and the reaction was stirred under nitrogen for 4 hours. After the reaction, ethyl acetate was added to the obtained reaction mixture to extract an upper white solid, which was concentrated under reduced pressure to obtain a crude reaction product, which was recrystallized from absolute methanol to obtain 12.36g of a pale yellow solid, with a yield of 42.13%.
Comparative example 15
Preparation of N-lauroyl sarcosine sodium:
21.4g (0.1 mol) of methyl laurate, 27.75g (0.25 mol) of sodium sarcosinate, 92g (1 mol) of glycerol and 0.162g (0.003 mol) of sodium methoxide prepared in the step (1) were charged into a four-necked flask equipped with a mechanical stirrer, a thermometer, a bulb-shaped condenser and a water separator, and after stirring uniformly, the temperature was raised to 135℃and the reaction was stirred under nitrogen for 4 hours. After the reaction, ethyl acetate was added to the obtained reaction solution to extract an upper white solid, the mixture was concentrated under reduced pressure to obtain a crude reaction product, and the crude reaction product was recrystallized from anhydrous methanol to obtain 21.56g of a pale yellow solid, with a yield of 73.49%.
The above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments may be modified or some technical features may be replaced equivalently; such modifications and substitutions do not depart from the spirit of the invention.
Claims (7)
1. The preparation method of the N-lauroyl sarcosine sodium is characterized by comprising the following steps of:
(1) Uniformly mixing lauric acid, methanol and sodium bisulfate monohydrate, and then reacting at 80 ℃ for 4-10 hours to prepare methyl laurate, wherein a water separator is arranged in the reaction process to reduce the water content in the reaction process; wherein the molar ratio of lauric acid to methanol is 1:8.5-9.5; the molar ratio of the lauric acid to the sodium bisulfate monohydrate is 1:0.13-0.17;
(2) Under the protection of nitrogen, carrying out condensation reaction on methyl laurate, sodium sarcosinate and sodium methoxide prepared in the step (1) at 135 ℃ for 3-8 hours to prepare N-lauroyl sodium sarcosinate; wherein the molar ratio of the methyl laurate to the sodium sarcosinate is 1:2.3-2.8; the molar ratio of the methyl laurate to the sodium methoxide is 1:0.015-0.025;
the specific synthetic route is as follows:
2. the method for producing sodium N-lauroyl sarcosinate according to claim 1, wherein in the step (1), the reaction time is 5 hours.
3. The method for producing sodium N-lauroyl sarcosinate according to claim 1, wherein in the step (1), the molar ratio of lauric acid to methanol is 1:9.
4. The method for producing sodium N-lauroyl sarcosinate according to claim 1, wherein in the step (1), the molar ratio of lauric acid to sodium bisulfate monohydrate is 1:0.15.
5. The method for producing sodium N-lauroyl sarcosinate according to claim 1, wherein in the step (2), the reaction time is 4 hours.
6. The method for producing sodium N-lauroyl sarcosinate according to claim 1, wherein in the step (2), the molar ratio of methyl laurate to sodium sarcosinate is 1:2.5.
7. The method for producing sodium N-lauroyl sarcosinate according to claim 1, wherein in the step (2), the molar ratio of methyl laurate to sodium methoxide is 1:0.02.
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| CN102311359A (en) * | 2011-06-16 | 2012-01-11 | 北京工商大学 | Method for preparing N-fatty acyl amino acid surfactant from methyl ester |
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| CN105531256A (en) * | 2013-08-19 | 2016-04-27 | 斯泰潘公司 | Process for preparing N-acyl amino acid salts |
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| CN102816142A (en) * | 2012-08-22 | 2012-12-12 | 福建天富生物科技发展有限公司 | Synthesis method for pentadecanoicacid |
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