CN107353218B - Method for preparing vinyl bis-stearamide by using hydrogenated oil - Google Patents
Method for preparing vinyl bis-stearamide by using hydrogenated oil Download PDFInfo
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Abstract
The invention belongs to the technical field of chemical industry, and particularly relates to a method for preparing vinyl bis-stearamide by using hydrogenated oil. The invention provides a method for preparing vinyl bis-stearamide by using hydrogenated oil, which comprises the steps of taking hydrogenated palm oil as a raw material, reacting stearic acid obtained by saponification with ethylenediamine, taking T501 as an antioxidant, and compounding phosphoric acid and tert-butoxy lithium as a catalyst to obtain the vinyl bis-stearamide. The preparation process is simple, the reaction conditions are not harsh, and three wastes are avoided; the reaction temperature of the saponification reaction of the hydrogenated palm oil is low, the time is short, and the saponification rate is high; the ethylene bis-stearamide prepared by the method has high purity, low chroma, narrow melting range and high yield.
Description
Technical Field
The invention belongs to the technical field of chemical industry, and particularly relates to a method for preparing vinyl bis-stearamide by using hydrogenated oil.
Background
Vinyl bis stearamide, also known AS ethylene bis stearamide (EBS for short), is a representative species of fatty bis amide compounds AS a plastic lubricant, and plays a major role in processing rigid thermoplastic resins such AS PVC, ABS, AS, PC, POM, and the like. Currently, EBS synthesis methods can be generally divided into 4 routes: 1) reacting stearic acid with an amine compound; 2) reacting stearate with amine compounds; 3) reacting stearoyl chloride with an amine compound; 4) and (4) hydrolyzing nitrile compounds. The first method has simple process, mild reaction conditions, no three wastes and low purity; the latter three methods can obtain high-purity products, but have the disadvantages of high energy consumption, complex process and long working procedure. From the perspective of large-scale process, although the first method is easy to implement and the obtained product has low cost, the ammonium salt intermediate generated in the salt forming stage is easy to color, so that the color value of the product is higher, and other side reactions occur in the ammonium salt in the dehydration stage, so that the purity of the product is reduced, and the melting range is widened.
Stearic acid which is a raw material for preparing EBS is usually prepared from palm oil through hydrogenation, saponification and acidolysis, and the saponification reaction of the hydrogenated palm oil has the problems of overlong saponification time, incomplete saponification and even difficult saponification due to the insolubility of the hydrogenated palm oil and an alkali solution, and the stearic acid can be completely saponified generally at the reaction temperature of 90-100 ℃ for 3-4 hours under conventional conditions. Therefore, how to increase the saponification rate and shorten the reaction time is a problem which needs to be solved urgently.
Chinese patent application CN105777568A discloses a preparation method of vinyl bis stearamide,
The preparation method takes stearic acid and ethylenediamine as raw materials, takes a composite oxidant compounded by an antioxidant 1076, an antioxidant DLTDP and an antioxidant T501 as a reaction antioxidant, and takes methylbenzenesulfonic acid/SAPO-34 supported solid super acidic catalyst and phosphoric acid/SiO2-Al2O3The composite catalyst compounded by the supported solid super acidic catalyst is a reaction catalyst. Although the vinyl bis-stearamide prepared by the method has high yield and purity, low chroma and narrow melting range, the effect of the vinyl bis-stearamide needs to be improved.
Chinese patent application CN105753698A discloses a method for preparing pentaerythritol stearate by using hydrogenated oil, comprising the following steps: s1, adding a sodium hydroxide solution into the hydrogenated palm oil, performing microwave treatment, and reacting under stirring to obtain a saponified substance; s2, adding a sulfuric acid solution into the saponified substance until the pH value is 1-2, transferring the material into a distillation tower, and distilling to obtain stearic acid; s3, adding stearic acid, pentaerythritol and a catalyst, heating the materials, controlling negative pressure, and reacting; s4, increasing the vacuum degree to 0.07-0.09 MPa, heating the material to 155-165 ℃, and reacting for 130-150 minutes under the condition of heat preservation and constant pressure; and S5, cooling after the esterification condensation reaction is finished, adding diatomite for decoloring and deodorizing, entering a plate-and-frame filter press, discarding a filter cake, spraying powder, spraying beads, slicing, packaging and warehousing. In the invention, the saponification rate of the saponification reaction of the hydrogenated palm oil is low and needs to be improved.
Disclosure of Invention
In order to solve the problems in the prior art, the invention aims to provide a method for preparing vinyl bis-stearamide by using hydrogenated oil. The method for preparing the vinyl bis-stearamide by using the hydrogenated oil has the advantages of simple process, mild reaction conditions and no three wastes; the saponification rate of the hydrogenated oil is high; the prepared vinyl bis-stearamide has high purity, low chroma, narrow melting range and high yield.
The invention provides a method for preparing vinyl bis-stearamide by using hydrogenated oil, which comprises the following steps:
S1 adding hydrogenated palm oil into a reactor, stirring and adding 30-40% sodium hydroxide solution and heteropoly acid-SbF5The solid super acidic catalyst, the ultrasonic power is controlled to be 280-360W, the reaction temperature is 70-80 ℃, the stirring speed is 200-300r/min, and the reaction time is 5-7h, so as to obtain a saponified substance;
S2, adding a sulfuric acid solution with the volume concentration of 15-25% into the saponified substance obtained in the step S1 while stirring until the pH value is 1-2, stopping acidification, cooling to room temperature, standing for 1-2h, taking the lower layer liquid, placing the lower layer liquid in a distillation tower, and distilling under the pressure of 0.08-0.09MPa and the temperature of 230-250 ℃ to obtain stearic acid;
S3, adding the stearic acid obtained in the step S2 and an antioxidant T501 into a reaction kettle, heating the mixture under the protection of nitrogen until the stearic acid is melted, adding a catalyst while stirring, dropwise adding ethylenediamine by using a constant-pressure dropping funnel when the temperature reaches 70-120 ℃, and keeping the dropwise adding for 35-45 min; after the dropwise addition of the ethylenediamine is finished, heating to 130 ℃, keeping the temperature for 1h, then heating to 160-200 ℃, keeping the temperature for 3-5h to perform dehydration reaction, carrying out the reaction with the generated water out by nitrogen, stopping the reaction when the acid value is less than 10mgKOH/g, cooling to 160 ℃, and discharging the material to obtain the ethylene diamine.
wherein the hydrogenated palm oil is purchased from the extremely hydrogenated palm oil of Guangzhou Huang Ri Biotech Co., Ltd, and the antioxidant T501 is purchased from Guangdong Plastic Medium chemical technology Co., Ltd.
Further, the mass ratio of the hydrogenated palm oil to the sodium hydroxide solution in the step S1 is 5 (1-2).
Further, heteropoly acid-SbF in the step S15The addition amount of the solid super acidic catalyst is 1-3% of the mass of the hydrogenated palm oil.
Further, heteropoly acid-SbF in the step S15the solid super acidic catalyst is H3SiW12O40-SbF5In which H is3SiW12O40-SbF5The preparation method of the catalyst comprises the following steps: h is to be3SiW12O40Loading on silica gel with a loading capacity of 20%, oven drying 4g of supported heteropolyacid at 110 deg.C, placing in an operation box, and adding 0.1mL of SbF5stirring, transferring into a dryer for full adsorption, and purging excessive SbF with 90 deg.C dry nitrogen gas5and (5) obtaining the product.
In the saponification reaction of hydrogenated palm oil, the hydrogenated palm oil and an alkali solution are not mutually soluble, so the saponification reaction has the problems of overlong saponification time, incomplete saponification and even difficult saponification, and the like, and the inventor finds that the addition of a PEG-600 phase transfer catalyst can promote the two-phase solubility and promote the reaction in the previous research, but the saponification rate is not ideal, so the inventor researches the phase transfer catalyst through a large amount of experiments, and occasionally uses heteropoly acid-SbF5Solid superacid, preferably H, as catalyst for the saponification reaction3SiW12O40-SbF5The saponification rate of the saponification reaction can be effectively improved by using ultrasonic treatment, and the saponification rate is more than or equal to 93.7%.
Further, the addition amount of the antioxidant T501 in the step S3 is 0.3-0.5% of the mass of the stearic acid, and the addition amount of the catalyst is 0.1-0.3% of the mass of the stearic acid.
Further, the catalyst in the step S3 is composed of phosphoric acid and lithium tert-butoxide in a mass ratio of 1: 3.
Further, the molar ratio of stearic acid to ethylenediamine in the step S3 is 2 (0.6-1.0).
In a molten state, stearic acid reacts with ethylenediamine to generate intermediate amine salt, and the amine salt is decomposed at the temperature of more than 140 ℃ and dehydrated to prepare the vinyl bis stearamide. The amine salt of the intermediate is very colored and aminolysis affects the color, so it is important to control the reaction temperature and to select the catalyst and antioxidant. The invention adopts phosphoric acid and tert-butoxy lithium as catalysts, improves the yield and purity of the product and reduces the product chroma by controlling the temperature and selecting an antioxidant.
Compared with the prior art, the invention has the following advantages:
(1) The method for preparing the vinyl bis-stearamide by using the hydrogenated oil has the advantages of simple process, mild reaction conditions and no three wastes;
(2) In the method for preparing the vinyl bis-stearamide by using the hydrogenated oil, the reaction temperature of the saponification reaction of the hydrogenated palm oil is low, the time is short, and the saponification rate is high and can reach as high as 97.2%;
(3) the vinyl bis-stearamide prepared by using the hydrogenated oil has high purity, low chroma, narrow melting range and high yield, and the purity can reach as high as 98.3 percent, and the yield can reach as high as 99.1 percent.
Detailed Description
The present invention is further illustrated by the following specific examples, which are provided for illustrative purposes only and do not limit the scope of the present invention.
Example 1A method for preparing vinyl bis-stearamide using hydrogenated oil
The method for preparing the vinyl bis-stearamide by using the hydrogenated oil comprises the following steps:
S1 adding hydrogenated palm oil into a reactor, stirring and adding 30% sodium hydroxide solution and 1% H3SiW12O40-SbF5Controlling the ultrasonic power to be 280W, the reaction temperature to be 70 ℃, the stirring speed to be 200r/min and the reaction time to be 5h to obtain a saponified substance;
S2, adding a sulfuric acid solution with the volume concentration of 15% into the saponified substance obtained in the step S1 while stirring until the pH value is 1, stopping acidification, cooling to room temperature, standing for 1h, taking the lower layer liquid, placing the lower layer liquid into a distillation tower, and distilling at the pressure of 0.08MPa and the temperature of 230 ℃ to obtain stearic acid;
S3, adding stearic acid obtained in the step S2 and an antioxidant T501 accounting for 0.3 percent of the mass of the stearic acid into a reaction kettle, heating the mixture under the protection of nitrogen until the stearic acid is melted, adding a catalyst accounting for 0.1 percent of the mass of the stearic acid while stirring, dropwise adding ethylenediamine by using a constant-pressure dropping funnel when the temperature reaches 70 ℃, and keeping the dropwise adding for 35 min; after the dropwise addition of the ethylenediamine is finished, heating to 130 ℃, keeping the temperature for 1h, then heating to 160 ℃, keeping the temperature for 3h to perform dehydration reaction, bringing out generated water by nitrogen along with the reaction, stopping the reaction when the acid value is less than 10mgKOH/g, and discharging to obtain the ethylene diamine.
wherein the mass ratio of the hydrogenated palm oil to the sodium hydroxide solution is 5:1, the molar ratio of stearic acid to ethylenediamine is 2:0.6, and the catalyst consists of phosphoric acid and tert-butoxy lithium in a mass ratio of 1: 3.
Example 2A method for preparing vinyl bis-stearamide using hydrogenated oil
The method for preparing the vinyl bis-stearamide by using the hydrogenated oil comprises the following steps:
S1 adding hydrogenated palm oil into a reactor, stirring and adding 35% sodium hydroxide solution and 2% H3SiW12O40-SbF5Controlling the ultrasonic power to be 320W, the reaction temperature to be 75 ℃, the stirring speed to be 250r/min and the reaction time to be 6h to obtain a saponified substance;
s2, adding a sulfuric acid solution with the volume concentration of 20% into the saponified substance obtained in the step S1 while stirring until the pH value is 1.5, stopping acidification, cooling to room temperature, standing for 1.5h, taking the lower layer liquid, placing the lower layer liquid into a distillation tower, and distilling at the pressure of 0.08MPa and the temperature of 240 ℃ to obtain stearic acid;
s3, adding stearic acid obtained in the step S2 and an antioxidant T501 with the mass of 0.4% of that of the stearic acid into a reaction kettle, heating the mixture under the protection of nitrogen until the stearic acid is melted, adding a catalyst with the mass of 0.2% of that of the stearic acid while stirring, dropwise adding ethylenediamine by using a constant-pressure dropping funnel when the temperature reaches 95 ℃, and keeping the dropwise adding completion for 40 min; after the dropwise addition of ethylenediamine is finished, heating to 130 ℃, keeping the temperature for 1h, then heating to 180 ℃, keeping the temperature for 4h to perform dehydration reaction, bringing out generated water with the progress of the reaction by nitrogen, stopping the reaction when the acid value is less than 10mgKOH/g, and cooling to 160 ℃, and discharging the material to obtain the catalyst.
Wherein the mass ratio of the hydrogenated palm oil to the sodium hydroxide solution is 5:1.5, the molar ratio of stearic acid to ethylenediamine is 2:0.8, and the catalyst consists of phosphoric acid and tert-butoxy lithium in a mass ratio of 1: 3.
example 3A method for preparing vinyl bis-stearamide using hydrogenated oil
The method for preparing the vinyl bis-stearamide by using the hydrogenated oil comprises the following steps:
S1 adding hydrogenated palm oil into a reactor, stirring and adding sodium hydroxide solution with the mass concentration of 40% and H with the mass concentration of 3% of the hydrogenated palm oil3SiW12O40-SbF5Controlling the ultrasonic power to be 360W, the reaction temperature to be 80 ℃, the stirring speed to be 300r/min and the reaction time to be 7h to obtain the saponificationAn agent;
S2, adding a sulfuric acid solution with the volume concentration of 25% into the saponified substance obtained in the step S1 while stirring until the pH value is 2, stopping acidification, cooling to room temperature, standing for 2 hours, taking the lower layer liquid, placing the lower layer liquid into a distillation tower, and distilling at the pressure of 0.09MPa and the temperature of 250 ℃ to obtain stearic acid;
S3, adding stearic acid obtained in the step S2 and an antioxidant T501 with the mass of 0.5% of that of the stearic acid into a reaction kettle, heating the mixture under the protection of nitrogen until the stearic acid is melted, adding a catalyst with the mass of 0.3% of that of the stearic acid while stirring, dropwise adding ethylenediamine by using a constant-pressure dropping funnel when the temperature reaches 120 ℃, and keeping the dropwise adding completion for 45 min; after the dropwise addition of ethylenediamine is finished, heating to 130 ℃, keeping the temperature for 1h, then heating to 200 ℃, keeping the temperature for 5h to perform dehydration reaction, bringing out generated water with the progress of the reaction by nitrogen, stopping the reaction when the acid value is less than 10mgKOH/g, and cooling to 160 ℃, and discharging the material to obtain the catalyst.
Wherein the mass ratio of the hydrogenated palm oil to the sodium hydroxide solution is 5:2, the molar ratio of stearic acid to ethylenediamine is 2:1.0, and the catalyst consists of phosphoric acid and tert-butoxy lithium in a mass ratio of 1: 3.
Comparative example 1A method for preparing vinyl bis-stearamide using hydrogenated oil
In the preparation method, H in step S13SiW12O40-SbF5The procedure was followed in example 2 except that polyethylene glycol-600 was used instead.
Comparative example 2A method for preparing Vinylbisamide from hydrogenated oil
The preparation method was the same as that of example 2 except that the catalyst in step S3 was replaced with a composition of phosphoric acid and tert-butoxylithium in a mass ratio of phosphoric acid to phosphorous acid.
Comparative example 3A method for preparing Vinylbis-stearamide using hydrogenated oil
In the preparation method, the catalyst in step S3 was replaced by one composed of phosphoric acid and t-butoxylithium in a mass ratio of 1:3 instead of one composed of phosphoric acid and t-butoxylithium in a mass ratio of 1:1, as in example 2.
test example one saponification rate of hydrogenated palm oil saponification reaction
The saponification rate of the hydrogenated palm oil saponification reaction in examples 1-3 and comparative example 1 was calculated. Setting a blank test, sampling after the saponification reaction is finished, respectively adding appropriate phenolphthalein indicators, titrating by using a hydrochloric acid standard solution with a calibrated concentration, and recording the volume of the required hydrochloric acid. The saponification rate was calculated according to the following formula:
Wherein in the formula V0The volume of hydrochloric acid consumed for titration of the blank set, mL; c is the concentration of the hydrochloric acid standard solution, mol/L; m is the mass of hydrogenated palm oil, g; s is the saponification value (KOH) of palm oil, mg/g; 56.11 is the molar mass of KOH, g/mol. The results of the saponification rate calculation are shown in Table 1.
TABLE 1 saponification rate results for hydrogenated palm oil saponification reactions
| Item | Example 1 | example 2 | Example 3 | comparative example 1 |
| Saponification ratio (%) | 95.5 | 97.2 | 93.7 | 78.5 |
From Table 1, it can be seen thatIn comparison with ratio 1, the saponification rate of the hydrogenated palm oil saponification reaction in examples 1 to 3 of the present invention was higher. The invention adopts H3SiW12O40-SbF5As a catalyst, the progress of the saponification reaction is promoted, and the saponification rate is improved.
Test example II detection of index of vinyl bis stearamide
the vinyl bis-stearamides prepared in examples 1-3 and comparative examples 2-3 of the present invention were tested for their relevant indices according to industry standard HG/T4784-2014N, N' -ethylene bis-stearamide (EBS), and the test results are shown in table 2.
TABLE 2 index test results for vinyl bis stearamide
As shown in Table 2, all indexes of the vinyl bis-stearamide prepared by the invention all meet the relevant standards of HG/T4784-2014, and the product has high purity, low chroma and narrow melting range. Compared with comparative examples 2-3, the vinyl bis-stearamide prepared by compounding phosphoric acid and lithium tert-butoxide as a catalyst in examples 1-3 of the invention has better indexes and better effect when the mass ratio is 1: 3.
Test example III determination of yield and purity of vinyl bis stearamide
the vinyl bis-stearamides prepared in examples 1-3 and comparative examples 2-3 were examined for yield and purity, and the results are shown in Table 3.
TABLE 3 results of yield and purity measurements of vinyl bis stearamide
| Item | example 1 | Example 2 | Example 3 | Comparative example 2 | Comparative example 3 |
| yield/%) | 97.5 | 99.1 | 95.8 | 81.3 | 85.9 |
| Purity/%) | 94.9 | 98.3 | 96.6 | 80.2 | 85.4 |
As shown in Table 3, the vinyl bis-stearamide prepared by the method is high in yield and purity. Compared with comparative examples 2-3, in the method for preparing the vinyl bis-stearamide according to the embodiments 1-3 of the present invention, phosphoric acid and tert-butoxylithium are compounded as a catalyst, and T501 is used as an antioxidant, so that the temperature is controlled, the occurrence of side reactions is reduced, and the chromaticity of the product is reduced, thereby increasing the yield and purity of the product vinyl bis-stearamide.
Claims (6)
1. A method for preparing vinyl bis stearamide by using hydrogenated oil is characterized by comprising the following steps:
S1 adding hydrogenated palm oil into the reactor, stirring and adding the mixture with the mass concentration of 30-40% sodium hydroxide solution and heteropolyacid-SbF5The solid super acidic catalyst, the ultrasonic power is controlled to be 280-360W, the reaction temperature is 70-80 ℃, the stirring speed is 200-300r/min, and the reaction time is 5-7h, so as to obtain a saponified substance;
S2, adding a sulfuric acid solution with the volume concentration of 15-25% into the saponified substance obtained in the step S1 while stirring until the pH value is 1-2, stopping acidification, cooling to room temperature, standing for 1-2h, taking the lower layer liquid, placing the lower layer liquid in a distillation tower, and distilling under the pressure of 0.08-0.09MPa and the temperature of 230-250 ℃ to obtain stearic acid;
s3, adding the stearic acid obtained in the step S2 and an antioxidant T501 into a reaction kettle, heating the mixture under the protection of nitrogen until the stearic acid is melted, adding a catalyst while stirring, dropwise adding ethylenediamine by using a constant-pressure dropping funnel when the temperature reaches 70-120 ℃, and keeping the dropwise adding for 35-45 min; after the dropwise addition of ethylenediamine is finished, heating to 130 ℃, keeping the temperature for 1h, then heating to 160-200 ℃, keeping the temperature for 3-5h to perform dehydration reaction, carrying out the reaction with the generated water out by nitrogen, stopping the reaction when the acid value is less than 10mgKOH/g, and cooling to 160 ℃ to discharge the material to obtain the ethylene diamine aqueous solution;
the catalyst in the step S3 consists of phosphoric acid and lithium tert-butoxide in a mass ratio of 1: 3.
2. The method for preparing vinyl bis-stearamide using hydrogenated oil according to claim 1, wherein the mass ratio of hydrogenated palm oil to sodium hydroxide solution in step S1 is 5 (1-2).
3. The method for preparing vinyl bis-stearamide using hydrogenated oil according to claim 1, wherein the heteropoly acid-SbF in step S15The addition amount of the solid super acidic catalyst is 1-3% of the mass of the hydrogenated palm oil.
4. the method for preparing vinyl bis-stearamide using hydrogenated oil according to claim 1, wherein the heteropoly acid-SbF in step S15The solid super acidic catalyst is H3SiW12O40-SbF5。
5. the method for preparing vinyl bis-stearamide using hydrogenated oil according to claim 1, wherein the antioxidant T501 is added in an amount of 0.3 to 0.5% by mass of stearic acid and the catalyst is added in an amount of 0.1 to 0.3% by mass of stearic acid in step S3.
6. the method for preparing vinyl bisstearamide using hydrogenated oil according to claim 1, wherein the molar ratio of stearic acid to ethylenediamine in the step S3 is 2 (0.6-1.0).
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105753698A (en) * | 2016-04-26 | 2016-07-13 | 广州煌垅生物科技有限公司 | Method for preparing pentaerythritol stearate from hydrogenated oil |
| CN105777568A (en) * | 2016-04-08 | 2016-07-20 | 广州煌垅生物科技有限公司 | Preparation method of vinyl distearamide |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777568A (en) * | 2016-04-08 | 2016-07-20 | 广州煌垅生物科技有限公司 | Preparation method of vinyl distearamide |
| CN105753698A (en) * | 2016-04-26 | 2016-07-13 | 广州煌垅生物科技有限公司 | Method for preparing pentaerythritol stearate from hydrogenated oil |
Non-Patent Citations (1)
| Title |
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| 用于制备生物柴油的固体酸催化剂的研究进展;刘亚录等;《石油学报》;20150630;第31卷(第3期);第629页第1.2节 * |
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