CN114478294A - Preparation method of hydroxyethyl stearic acid amide - Google Patents
Preparation method of hydroxyethyl stearic acid amide Download PDFInfo
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- CN114478294A CN114478294A CN202210072372.XA CN202210072372A CN114478294A CN 114478294 A CN114478294 A CN 114478294A CN 202210072372 A CN202210072372 A CN 202210072372A CN 114478294 A CN114478294 A CN 114478294A
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- China
- Prior art keywords
- stearic acid
- hydroxyethyl
- reaction
- weight
- inhibitor
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- NYEXLIJYTKEDLX-UHFFFAOYSA-N 2-(2-hydroxyethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCC(C(N)=O)CCO NYEXLIJYTKEDLX-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 235000021355 Stearic acid Nutrition 0.000 claims abstract description 30
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 30
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000008117 stearic acid Substances 0.000 claims abstract description 30
- 239000003112 inhibitor Substances 0.000 claims abstract description 12
- 238000002844 melting Methods 0.000 claims abstract description 12
- 230000008018 melting Effects 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 238000010438 heat treatment Methods 0.000 claims description 20
- 239000000047 product Substances 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 9
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical group C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 7
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 7
- 239000001488 sodium phosphate Substances 0.000 claims description 7
- 239000001119 stannous chloride Substances 0.000 claims description 7
- 235000011150 stannous chloride Nutrition 0.000 claims description 7
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical group [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 7
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims description 7
- 235000019801 trisodium phosphate Nutrition 0.000 claims description 7
- -1 amino ester Chemical class 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 230000035484 reaction time Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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 discloses a preparation method of hydroxyethyl stearamide, which is characterized in that stearic acid and monoacetamide directly react under the action of a catalyst and an inhibitor to prepare the hydroxyethyl stearamide product with low acid value, good color, high melting point and stable quality.
Description
Technical Field
The invention relates to the technical field of preparation of fatty acid amide, in particular to a preparation method of hydroxyethyl stearic acid amide.
Background
Hydroxyethyl stearic acid amide
Is a green surfactant, has good biodegradability, has excellent antistatic, lubricating, slipping, anti-sticking, dispersing, emulsifying, thickening, rust-resisting and anti-scraping effects and is widely used in the industries of plastics, rubber, textile, metal processing, medicine, daily chemical and the likeThe field of the technology.
With the continuous expansion of the application field, new higher requirements are provided for the quality of the hydroxyethyl stearamide product, and the hydroxyethyl stearamide product prepared by the prior art has high acid value, high amine value, deep color, low melting point and unstable quality, cannot be popularized and applied in the fields of high polymer materials, plastic-wood composite materials and the like, needs to be refined and purified, increases the cost and influences the popularization and application of the hydroxyethyl stearamide product.
The method for preparing hydroxyethyl stearic acid amide by directly reacting stearic acid with monoacetamide has the advantages of simple process and obvious cost advantage, but the key core is the addition and application of a high-activity high-selectivity synthesis catalyst and how to strictly control the formation of by-products such as amino ester, amido ester and the like, otherwise, high-quality products are difficult to obtain.
Disclosure of Invention
The invention aims to provide a preparation method of hydroxyethyl stearamide, which aims to solve the problems of high acid value, high amine value, dark color, low melting point and the like of products in the prior art.
The purpose of the invention is realized as follows:
a preparation method of hydroxyethyl stearic acid amide is characterized in that: under the action of a catalyst and an inhibitor, stearic acid and monoacetamide directly react to prepare hydroxyethyl stearic amide, and the method specifically comprises the following steps:
A. early-stage reaction: adding stearic acid into a reaction kettle, heating to 70-80 ℃ under a vacuum state, adding monoacetamide after the stearic acid is dissolved, starting stirring, adding an inhibitor, continuously heating to 148-168 ℃, reacting under the pressure of 0-0.15 MPa, and starting evacuation reaction for 2-4 hours; wherein: the weight ratio of stearic acid to monoacetamide is 1: 0.18 to 0.26; the addition weight of the inhibitor is 0.3-1.6% of that of stearic acid, and the inhibitor mainly has the effect of inhibiting the generation of byproducts such as amino ester, amido ester and the like;
B. middle and later stage reaction: vacuumizing, and adding a catalyst, wherein the adding weight of the catalyst is 0.03-0.3% of that of stearic acid; continuously heating to 168-180 ℃, keeping the vacuum degree in the kettle at-0.1-0 MPa, and continuously reacting for 2-4 hours;
C. after the reaction is finished, cooling to 120 ℃, and filtering to obtain a finished product of the hydroxyethyl stearamide, wherein the acid value of the hydroxyethyl stearamide is less than or equal to 3.0mgKOH/g, the amine value is less than or equal to 2.2mgKOH/g, the color is less than or equal to 2Gardner, and the melting point is 88-92 ℃.
Preferably, in the step A, the weight ratio of stearic acid to monoacetamide is 1: 0.20 to 0.22.
Preferably, in the step A, the inhibitor is trisodium phosphate, and the addition weight of the trisodium phosphate is 0.5-0.8% of the amount of stearic acid.
Preferably, in the step A, the temperature of the early reaction is 158-165 ℃.
Preferably, in the step B, the catalyst is stannous chloride, and the addition weight of the stannous chloride is 0.06-0.15% of the weight of the stearic acid.
Preferably, in the step B, the temperature of the middle and later stage reaction is 170-175 ℃.
The main reaction formula of the invention is as follows:
the invention is under the action of catalyst and inhibitor, stearic acid reacts with monoacetamide directly to make hydroxyethyl stearamide product with low acid value, good color, high melting point and stable quality, the obtained hydroxyethyl stearamide product has the advantages of omitting the working procedures of refining and purifying the product and reducing the cost, the problems of high acid value, high amine value, deep color, low melting point and the like of the product in the prior art are solved, and the product is suitable for the fields of high polymer materials and plastic-wood composite materials.
Detailed Description
The present invention will be better understood from the following examples, however, the description of the examples is only for the purpose of illustrating the present invention and should not be construed as limiting the invention as detailed in the claims.
Example 1
Adding 2.5kg of stearic acid into a 5L reaction kettle, heating to 70-80 ℃ in a vacuum state, adding 0.52kg of monoacetamide after the stearic acid is dissolved, starting stirring, adding 12.5g of trisodium phosphate, continuously heating to 160-165 ℃, keeping the pressure in the reaction kettle to be less than or equal to 0.15MPa, starting an emptying reaction, and keeping the emptying reaction time to be 3 hours;
vacuumizing, adding 1.5g of stannous chloride, continuously heating to 168-172 ℃, keeping the vacuum in the kettle at-0.1-0.085 MPa, continuously reacting for 3 hours, cooling to 120 ℃, and filtering to obtain a finished product of the hydroxyethyl stearamide, wherein the acid value of the finished product is 1.95mgKOH/g, the amine value is 1.22mgKOH/g, the color is 1.5Gardner, and the melting point is 90.3 ℃.
Example 2
Adding 2.5kg of stearic acid into a 5L reaction kettle, heating to 80-90 ℃ in a vacuum state, adding 0.55kg of monoacetamide after the stearic acid is melted, starting stirring, adding 25g of trisodium phosphate, continuously heating to 162-168 ℃, keeping the pressure in the reaction kettle to be less than or equal to 0.15MPa, starting an emptying reaction, wherein the emptying reaction time is 2 hours;
vacuumizing, adding 2.5g of stannous chloride, continuously heating to 170-175 ℃, keeping the vacuum degree in the kettle at-0.1-0.085 MPa, continuously reacting for 3.5h, cooling to 120 ℃, and filtering to obtain a finished hydroxyethyl stearamide product, wherein the acid value of the finished product is 2.32mgKOH/g, the amine value is 0.96mgKOH/g, the color is 2.0Gardner, and the melting point is 89.6 ℃.
Example 3
Adding 2.5kg of stearic acid into a 5L reaction kettle, heating to 90-100 ℃ in a vacuum state, adding 0.53kg of monoacetamide after the stearic acid is dissolved, starting stirring, adding 20g of trisodium phosphate, continuously heating to 155-160 ℃, keeping the pressure in the reaction kettle to be less than or equal to 0.15MPa, starting an emptying reaction, wherein the emptying reaction time is 4 hours;
vacuumizing, adding 3.75g of stannous chloride, continuously heating to 170-173 ℃, keeping the vacuum degree in the kettle at-0.1-0.085 MPa, continuously reacting for 3 hours, cooling to 120 ℃, and filtering to obtain a finished product of hydroxyethyl stearamide, wherein the acid value of the finished product is 1.46mgKOH/g, the amine value is 1.19mgKOH/g, the color is 1.0Gardner, and the melting point is 90.7 ℃.
Comparative example
Adding 2.5kg of stearic acid into a 5L reaction kettle, heating to about 60 ℃, starting to melt the stearic acid, starting stirring, continuously heating to about 80 ℃, completely melting the stearic acid, continuously heating to 95 ℃, starting to dropwise add 0.56kg of monoacetamide, automatically heating the materials, keeping the reaction temperature at 115-130 ℃, finishing dropwise adding within 0.5 hour, continuously keeping the temperature at 115-130 ℃ for reaction for 5 hours, keeping normal pressure for exhausting in the reaction period to take away water vapor generated in the reaction system, then continuously heating to 165-180 ℃, keeping the temperature for reaction for 2 hours, vacuumizing, after the reaction is finished, cooling and filtering to obtain a finished hydroxyethyl stearamide product, wherein the acid value is 6.32mgKOH/g, the amine value is 4.73mgKOH/g, the color is 3.0Gardner, and the melting point is 81.1 ℃.
Claims (6)
1. A preparation method of hydroxyethyl stearic acid amide is characterized in that: under the action of a catalyst and an inhibitor, stearic acid and monoacetamide directly react to prepare hydroxyethyl stearic amide, and the method specifically comprises the following steps:
A. early-stage reaction: adding stearic acid into a reaction kettle, heating to 70-80 ℃ in a vacuum state, adding monoacetamide after the stearic acid is dissolved, starting stirring, adding an inhibitor, continuously heating to 148-168 ℃, reacting under the pressure of 0-0.15 MPa, and starting emptying reaction for 2-4 hours; wherein: the weight ratio of stearic acid to monoacetamide is 1: 0.18 to 0.26; the addition weight of the inhibitor is 0.3-1.6% of that of stearic acid, and the inhibitor mainly has the effect of inhibiting the generation of byproducts such as amino ester and amido ester;
B. middle and later stage reaction: vacuumizing, and adding a catalyst, wherein the adding weight of the catalyst is 0.03-0.3% of that of stearic acid; continuously heating to 168-180 ℃, keeping the vacuum degree in the kettle at-0.1-0 MPa, and continuously reacting for 2-4 hours;
C. after the reaction is finished, cooling to 120 ℃, and filtering to obtain a finished product of the hydroxyethyl stearamide, wherein the acid value of the hydroxyethyl stearamide is less than or equal to 3.0mgKOH/g, the amine value is less than or equal to 2.2mgKOH/g, the color is less than or equal to 2Gardner, and the melting point is 88-92 ℃.
2. The method for producing hydroxyethyl stearic acid amide according to claim 1, characterized in that: in the step A, the weight ratio of stearic acid to monoacetamide is 1: 0.20 to 0.22.
3. The method for producing hydroxyethyl stearic acid amide according to claim 1, characterized in that: in the step A, the inhibitor is trisodium phosphate, and the addition weight of the trisodium phosphate is 0.5-0.8% of the weight of stearic acid.
4. The method for producing hydroxyethyl stearic acid amide according to claim 1, characterized in that: in the step A, the temperature of the early reaction is 158-165 ℃.
5. The method of preparing hydroxyethyl stearic acid amide according to claim 1, characterized in that: in the step B, the catalyst is stannous chloride, and the adding weight of the stannous chloride is 0.06-0.15% of the weight of the stearic acid.
6. The method for producing hydroxyethyl stearic acid amide according to claim 1, characterized in that: in the step B, the temperature of the middle and later stage reaction is 170-175 ℃.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210072372.XA CN114478294B (en) | 2022-01-21 | 2022-01-21 | Preparation method of hydroxyethyl stearic acid amide |
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| CN202210072372.XA CN114478294B (en) | 2022-01-21 | 2022-01-21 | Preparation method of hydroxyethyl stearic acid amide |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093240A (en) * | 2010-11-18 | 2011-06-15 | 浙江皇马科技股份有限公司 | Synthesis method of fatty acid monoethanal acid amide |
| CN102675138A (en) * | 2012-06-11 | 2012-09-19 | 科凯精细化工（上海）有限公司 | Synthetic method of fatty acid monoethanolamide |
| CN107445853A (en) * | 2017-07-06 | 2017-12-08 | 广州道明研究院有限公司 | A kind of synthetic method of fatty monoethanol amide |
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- 2022-01-21 CN CN202210072372.XA patent/CN114478294B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093240A (en) * | 2010-11-18 | 2011-06-15 | 浙江皇马科技股份有限公司 | Synthesis method of fatty acid monoethanal acid amide |
| CN102675138A (en) * | 2012-06-11 | 2012-09-19 | 科凯精细化工（上海）有限公司 | Synthetic method of fatty acid monoethanolamide |
| CN107445853A (en) * | 2017-07-06 | 2017-12-08 | 广州道明研究院有限公司 | A kind of synthetic method of fatty monoethanol amide |
Non-Patent Citations (1)
| Title |
|---|
| 化学工业部天津化工研究院 等 编: "《化工产品手册 无机化工产品》", 化学工业出版社, pages: 154 - 155 * |
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