CN116023645B - A kind of synthesis method of high molecular weight stearic acid polyoxyethylene ester - Google Patents
A kind of synthesis method of high molecular weight stearic acid polyoxyethylene ester Download PDFInfo
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Abstract
本发明公开了一种高分子量硬脂酸聚氧乙烯酯的合成方法，属于高分子化合物合成技术领域。该合成方法先将硬脂酸和负载型固体酸催化剂加入到高压反应釜中，密闭反应釜，开启搅拌并抽真空，置氮后抽真空，在真空条件下升温，脱水，加入环氧乙烷进行反应，放料、过滤，得乙二醇单硬脂酸酯；再将乙二醇单硬脂酸酯和碱金属催化剂加入到高压反应釜中，密闭反应釜，开启搅拌并抽真空，置氮后抽真空，在真空条件下升温、脱水，加入环氧乙烷，熟化、降温、脱气、中和、放料，得到硬脂酸聚氧乙烯酯。通过本发明的方法制得的硬脂酸聚氧乙烯酯产品质量稳定、色泽浅，能够有效降低硬脂酸聚氧乙烯酯中二恶烷和聚乙二醇的含量。
The invention discloses a synthesis method of high molecular weight stearic acid polyoxyethylene ester, and belongs to the technical field of polymer compound synthesis. The synthesis method first adds stearic acid and a supported solid acid catalyst to an autoclave, closes the autoclave, opens stirring and evacuates, evacuates after nitrogen is placed, heats up under vacuum conditions, dehydrates, adds ethylene oxide to react, discharges, filters, and obtains ethylene glycol monostearate; then adds ethylene glycol monostearate and an alkali metal catalyst to an autoclave, closes the autoclave, opens stirring and evacuates, evacuates after nitrogen is placed, heats up under vacuum conditions, dehydrates, adds ethylene oxide, matures, cools, degasses, neutralizes, discharges, and obtains stearic acid polyoxyethylene ester. The stearic acid polyoxyethylene ester product obtained by the method of the present invention has stable product quality and light color, and can effectively reduce the content of dioxane and polyethylene glycol in stearic acid polyoxyethylene ester.
Description
Technical Field
The invention relates to the technical field of high molecular compound synthesis, in particular to a method for synthesizing high molecular weight polyoxyethylene stearate.
Background
The polyoxyethylene stearate is an important surfactant, has good emulsifying, wetting and thickening properties, and is widely applied in various fields. For example, it is used in the pharmaceutical industry as an emulsifier, solubilizer, suppository base, ointment base, as an emulsifier, detergent, softener, antistatic agent in the textile industry, emulsifying additive in the food industry, etc. Therefore, the polyoxyethylene stearate has wide industrial application prospect and great development value.
The current industrial methods for preparing polyoxyethylene stearate mainly comprise an esterification method and an ethoxylation method. The reaction end point is difficult to determine when the polyoxyethylene stearate is prepared by the esterification method, so that the prepared product has deep color and luster, and the method has complex process and higher cost. Therefore, an ethoxylation method is generally used in industry to prepare polyoxyethylene stearate. The ethoxylation method is to add stearic acid and an alkaline catalyst into a reaction kettle to react with ethylene oxide at a certain temperature to obtain polyoxyethylene stearate. The ethoxylation method has the advantages of easy control of the end point, stable product quality, good color and the like, but the polyoxyethylene stearate prepared by the method has higher dioxane and polyethylene glycol high polymer content, and the dioxane and polyethylene glycol high polymer content greatly influence the use of the product.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a method for synthesizing high molecular weight polyoxyethylene stearate, and the polyoxyethylene stearate product prepared by the method has stable quality and light color and can effectively reduce the content of dioxane and polyethylene glycol in the polyoxyethylene stearate.
In order to solve the problems, the technical scheme adopted by the invention is as follows:
a method for synthesizing high molecular weight polyoxyethylene stearate, which comprises the following steps:
S1, adding stearic acid and a supported solid acid catalyst FeCl 3/γ-Al2O3 into a high-pressure reaction kettle, sealing the reaction kettle, starting stirring and vacuumizing, vacuumizing after replacing nitrogen for a plurality of times, heating to 60-90 ℃ under the vacuum condition, dehydrating for 1-2h, adding ethylene oxide for reaction for 1-3h, discharging after the reaction is finished, and filtering to obtain ethylene glycol monostearate;
S2, adding glycol monostearate and an alkali metal catalyst into a high-pressure reaction kettle, sealing the reaction kettle, starting stirring and vacuumizing, vacuumizing after replacing nitrogen for a plurality of times, heating to 90-110 ℃ under the vacuum condition, heating to 100-140 ℃ after dehydration for 1-2h, adding ethylene oxide, curing until the pressure is unchanged under the condition of keeping the internal pressure of the reaction kettle, cooling, degassing, neutralizing, and discharging to obtain the polyoxyethylene stearate.
As a preferred embodiment of the invention, the weight of the supported solid acid catalyst FeCl 3/γ-Al2O3 is 0.05% -0.1% of the theoretical weight of ethylene glycol monostearate.
As a preferred embodiment of the invention, the weight of the alkali metal catalyst is 0.1% -0.2% of the theoretical weight of polyoxyethylene stearate.
As a preferred embodiment of the present invention, the alkali metal catalyst is selected from one of KOH, naOH, CH 3 OK or CH 3 ONa.
In a preferred embodiment of the present invention, the number of times of nitrogen placement in the steps S1 and S2 is 2 to 5.
As a preferred embodiment of the present invention, the molar ratio of stearic acid to ethylene oxide in the step S1 is 1:1.1.
In a preferred embodiment of the present invention, the molar ratio of ethylene glycol monostearate to ethylene oxide in the step S2 is 1:39-99.
In a preferred embodiment of the present invention, the polymerization time in the step S1 is 1 to 2 hours.
As a preferred embodiment of the invention, the ethylene oxide in the step S2 is added in 1-4 hours, and the reaction pressure is kept below 0.4 MPa.
In a preferred embodiment of the present invention, the molecular weight of the high molecular weight polyoxyethylene stearate is 2027 to 4667g/mol.
Compared with the prior art, the invention has the beneficial effects that:
The invention adopts a two-step method to prepare the polyoxyethylene stearate, and uses a supported solid acid catalyst FeCl 3/γ-Al2O3 to catalyze the reaction, the catalyst can directly activate epoxy monomers, the activated monomers react with an initiator, no moisture is generated in the process, the reaction reacts in pore channels of the catalyst, the epoxy monomers are effectively prevented from generating tail biting reaction, and the content of dioxane is reduced. Therefore, the catalyst can effectively prevent the generation of dioxane and water in the reaction, so that the content of dioxane and polyethylene glycol in the product can be obviously reduced, the prepared polyoxyethylene stearate product has stable quality and light color, has good emulsifying, wetting and thickening properties, and can be widely applied to the fields of pharmacy, textile and the like.
Drawings
FIG. 1 is a photograph (60 ℃) of a polyoxyethylene stearate prepared in example 6 of the present invention;
FIG. 2 is a photograph (60 ℃) of the polyoxyethylene stearate produced in comparative example 6 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to the following embodiments.
Example 1
A method for synthesizing high molecular weight polyoxyethylene stearate, which comprises the following steps:
S1, synthesizing glycol monostearate, namely firstly adding 534g of stearic acid and 0.32g of FeCl 3/γ-Al2O3 catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring, vacuumizing, and replacing the gas in the kettle with nitrogen for 3 times. Heating to 90 ℃ after nitrogen placement, dropwise adding 106g of ethylene oxide, controlling the reaction temperature to 90+/-2 ℃ and the reaction pressure to 0-0.05 MPa, curing for 0.5h after adding, degassing, cooling to 60 ℃ and discharging, and filtering to remove the catalyst.
S2, synthesizing polyoxyethylene stearate 2027, namely firstly adding 240g of glycol monostearate and 1.52g of KOH catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring, vacuumizing, replacing gas in the kettle with nitrogen for 3 times, heating to 140 ℃, dropwise adding 1280g of ethylene oxide, controlling the reaction temperature to 140+/-2 ℃ and the reaction pressure to 0-0.4 MPa, curing for 0.5h after adding, degassing, neutralizing with acetic acid, and cooling to 80 ℃ for discharging to obtain polyoxyethylene stearate.
Example 2
A method for synthesizing high molecular weight polyoxyethylene stearate, which comprises the following steps:
S1, synthesizing glycol monostearate, namely firstly adding 534g of stearic acid and 0.51g of FeCl 3/γ-Al2O3 catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring, vacuumizing, and replacing the gas in the kettle with nitrogen for 3 times. Heating to 75 ℃ after nitrogen placement, dropwise adding 106g of ethylene oxide, controlling the reaction temperature to 75+/-2 ℃, controlling the reaction pressure to 0-0.05 MPa, curing for 0.5h after adding, degassing, cooling to 60 ℃ and discharging, and filtering to remove the catalyst.
S2, synthesizing polyoxyethylene stearate 2027, namely firstly adding 240g of glycol monostearate and 2.74g of KOH catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring, vacuumizing, replacing gas in the kettle with nitrogen for 3 times, heating to 120 ℃, dropwise adding 1280g of ethylene oxide, controlling the reaction temperature to 120+/-2 ℃, controlling the reaction pressure to 0-0.4 MPa, curing for 0.5h after adding, degassing, neutralizing with acetic acid, and cooling to 80 ℃ for discharging to obtain polyoxyethylene stearate.
Example 3
A method for synthesizing high molecular weight polyoxyethylene stearate, which comprises the following steps:
S1, synthesizing glycol monostearate, namely firstly adding 534g of stearic acid and 0.64g of FeCl 3/γ-Al2O3 catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring, vacuumizing, and replacing the gas in the kettle with nitrogen for 3 times. Heating to 60 ℃ after nitrogen placement, dropwise adding 106g of ethylene oxide, controlling the reaction temperature to be 60+/-2 ℃, controlling the reaction pressure to be 0-0.05 MPa, curing for 0.5h after adding, degassing, discharging, and filtering to remove the catalyst.
S2, synthesizing polyoxyethylene stearate 2027, namely firstly adding 240g of glycol monostearate and 3.04g of KOH catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring, vacuumizing, replacing gas in the kettle with nitrogen for 3 times, heating to 100 ℃, dropwise adding 1280g of ethylene oxide, controlling the reaction temperature to 100+/-2 ℃ and the reaction pressure to 0-0.4 MPa, curing for 0.5h after adding, degassing, neutralizing with acetic acid, and cooling to 80 ℃ for discharging to obtain polyoxyethylene stearate.
Example 4
A method for synthesizing high molecular weight polyoxyethylene stearate, which comprises the following steps:
S1, synthesizing glycol monostearate, namely firstly adding 534g of stearic acid and 0.32g of FeCl 3/γ-Al2O3 catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring, vacuumizing, and replacing the gas in the kettle with nitrogen for 3 times. Heating to 60 ℃ after nitrogen placement, dropwise adding 106g of ethylene oxide, controlling the reaction temperature to 90 ℃, controlling the reaction pressure to 0-0.05 MPa, curing for 0.5h after adding, degassing, cooling to 60 ℃ and discharging, and filtering to remove the catalyst.
S2, synthesizing polyoxyethylene stearate 2907, namely firstly adding 160g of glycol monostearate and 1.45g of KOH catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring, vacuumizing, replacing gas in the kettle with nitrogen for 3 times, heating to 140 ℃, dropwise adding 1293g of ethylene oxide, controlling the reaction temperature to 140 ℃, controlling the reaction pressure to 0-0.4 MPa, curing for 0.5h after adding, degassing, neutralizing with acetic acid, and finally cooling to 80 ℃ for discharging to obtain polyoxyethylene stearate.
Example 5
A method for synthesizing high molecular weight polyoxyethylene stearate, which comprises the following steps:
S1, synthesizing glycol monostearate, wherein the steps and conditions are the same as those in example 4.
S2, synthesizing polyoxyethylene stearate 3787, namely firstly adding 160g of glycol monostearate and 1.89g of KOH catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring, vacuumizing, replacing gas in the kettle with nitrogen for 3 times, heating to 140 ℃, dropwise adding 1733g of ethylene oxide, controlling the reaction temperature to 140 ℃, controlling the reaction pressure to 0-0.4 MPa, curing for 0.5h after adding, degassing, neutralizing with acetic acid, and finally cooling to 80 ℃ for discharging to obtain polyoxyethylene stearate.
Example 6
A method for synthesizing high molecular weight polyoxyethylene stearate, which comprises the following steps:
S1, synthesizing glycol monostearate, wherein the steps and conditions are the same as those in example 4.
S2, synthesizing polyoxyethylene stearate 4667, namely firstly adding 104g of glycol monostearate and 1.56g of KOH catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring, vacuumizing, replacing gas in the kettle with nitrogen for 3 times, heating to 140 ℃, dropwise adding 1452g of ethylene oxide, controlling the reaction temperature to 140 ℃, controlling the reaction pressure to 0-0.4 MPa, curing for 0.5h after the addition, degassing, neutralizing with acetic acid, and finally cooling to 80 ℃ for discharging to obtain polyoxyethylene stearate.
The process parameters for examples 1-6 are set forth in Table 1:
Table 1 process parameters of examples 1 to 6
Comparative examples 1 to 6
Comparative examples 1 to 6 are different from examples 1 to 6 in that the supported solid catalyst FeCl 3/γ-Al2O3 in S1 in examples 1 to 6 is replaced by an alkaline metal catalyst KOH, and the catalyst amount, the reaction temperature and the pressure are the same as those in examples 1 to 6, and other conditions are unchanged.
The process parameter pairs for comparative examples 1 to 6 are shown in table 2:
Table 2 Process parameters for comparative examples 1 to 6
Comparative example 7
A method for synthesizing polyoxyethylene stearate 2027 comprises the following steps of firstly adding 200g of stearic acid and 1.52g of KOH catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring and vacuumizing, then replacing gas in the kettle with nitrogen for 3 times, heating to 140 ℃, dropwise adding 1318g of ethylene oxide, controlling the reaction temperature to 140+/-2 ℃, controlling the reaction pressure to 0-0.4 MPa, curing for 0.5h after the addition, degassing, neutralizing with acetic acid, and cooling to 80 ℃ for discharging to obtain polyoxyethylene stearate.
Comparative examples 8 to 9
Comparative examples 8 to 9 are different from comparative example 7 in that the reaction temperatures are 120℃and 100℃respectively, the catalyst amounts are 0.18% and 0.2% respectively, and other conditions are the same as those of comparative example 7.
Comparative example 10
A method for synthesizing polyoxyethylene stearate 2907 comprises the following steps of firstly adding 140g of stearic acid and 1.52g of KOH catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring and vacuumizing, then replacing gas in the kettle with nitrogen for 3 times, heating to 140 ℃, dropwise adding 1384g of ethylene oxide, controlling the reaction temperature to 140 ℃, controlling the reaction pressure to 0-0.4 MPa, curing for 0.5h after the addition, degassing, neutralizing with acetic acid, and finally cooling to 80 ℃ for discharging to obtain polyoxyethylene stearate.
Comparative example 11
A method for synthesizing polyoxyethylene stearate 2907 comprises the following steps of firstly adding 134g of stearic acid and 1.9g of KOH catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring and vacuumizing, then replacing gas in the kettle with nitrogen for 3 times, heating to 140 ℃, dropwise adding 1767g of ethylene oxide, controlling the reaction temperature to 140 ℃, controlling the reaction pressure to 0-0.4 MPa, curing for 0.5h after adding, degassing, neutralizing with acetic acid, and finally cooling to 80 ℃ for discharging to obtain polyoxyethylene stearate.
Comparative example 12
A method for synthesizing polyoxyethylene stearate 4667 comprises the following steps of firstly adding 89g of stearic acid and 1.46g of KOH catalyst into a 2.5L high-pressure reaction kettle, sealing the reaction kettle, starting stirring and vacuumizing, then replacing gas in the kettle with nitrogen for 3 times, heating to 140 ℃, dropwise adding 1367g of ethylene oxide, controlling the reaction temperature to 140 ℃, reacting at 0-0.4 MPa, curing for 0.5h after adding, degassing, neutralizing with acetic acid, and finally cooling to 80 ℃ for discharging to obtain polyoxyethylene stearate.
The process parameter pairs for comparative examples 7-12 are shown in Table 3:
Table 3 Process parameters of comparative examples 7 to 12
| Comparative example | Catalyst amount% | Reaction temperature °c | EO mole number in product molecule |
| 7 | 0.10 | 140 | 40 |
| 8 | 0.18 | 120 | 40 |
| 9 | 0.20 | 100 | 40 |
| 10 | 0.10 | 140 | 60 |
| 11 | 0.10 | 140 | 80 |
| 12 | 0.10 | 140 | 100 |
Effect verification experiment:
The appearance, dioxane content and high molecular content of the polyoxyethylene stearates obtained in examples 1 to 6 and comparative examples 1 to 12 were examined, and the examination results are shown in Table 4 and FIG. 1 to FIG. 2.
Table 4 comparison of the properties of the products obtained in examples 1 to 6 and comparative examples 1 to 12
| Project | Dioxane content/ppm | Polyethylene glycol content/% |
| Example 1 | 12 | 0.6 |
| Comparative example 1 | 87 | 3.7 |
| Comparative example 7 | 153 | 6.9 |
| Example 2 | 8 | 0.5 |
| Comparative example 2 | 65 | 3.1 |
| Comparative example 8 | 129 | 5.8 |
| Example 3 | 3 | 0.4 |
| Comparative example 3 | 42 | 2.6 |
| Comparative example 9 | 95 | 4.9 |
| Example 4 | 11 | 0.7 |
| Comparative example 4 | 86 | 4.0 |
| Comparative example 10 | 162 | 7.2 |
| Example 5 | 13 | 0.9 |
| Comparative example 5 | 85 | 4.8 |
| Comparative example 11 | 149 | 7.7 |
| Example 6 | 12 | 1.0 |
| Comparative example 6 | 88 | 5.3 |
| Comparative example 12 | 151 | 8.2 |
As can be seen from Table 4, the polyoxyethylene stearate prepared by the two-step method of the present invention has a clear appearance (60 ℃) and a low dioxane content and a low polymer content, and the polyoxyethylene stearate prepared at a low temperature has a clear appearance (60 ℃) and a low dioxane content and a low polymer content, and the polyoxyethylene stearate prepared by the two-step method and the first step using the supported catalyst FeCl 3/gamma-Al 2O3 has a clear appearance (60 ℃) and a low dioxane content and a low polymer content. Fig. 1 and 2 are external views of the products of example 6 and comparative example 6, respectively, and it can be seen from fig. 1 and 2 that example 6 using the supported solid acid catalyst FeCl 3/γ-Al2O3 greatly improves the clarity of the product compared to comparative example 6 using the conventional basic metal catalyst KOH.
Therefore, the invention adopts a two-step method, and the stearic acid polyoxyethylene ether prepared by using the supported catalyst FeCl 3/γ-Al2O3 in the first step is qualified in index and stable in quality.
The above embodiments are only preferred embodiments of the present invention, and the scope of the present invention is not limited thereto, but any insubstantial changes and substitutions made by those skilled in the art on the basis of the present invention are intended to be within the scope of the present invention as claimed.
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| CN108102083A (en) * | 2016-11-24 | 2018-06-01 | 上海东大化学有限公司 | A kind of cithrol and preparation method thereof |
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| CN109628232B (en) * | 2019-01-09 | 2022-04-29 | 广州美晨科技实业有限公司 | Preparation method of polyglycerol fatty acid ester |
| CN110156978B (en) * | 2019-05-24 | 2021-08-27 | 上海多纶化工有限公司 | Synthetic method of polyoxyethylene fatty acid ester |
| CN113735707B (en) * | 2021-10-18 | 2023-06-13 | 浙江皇马科技股份有限公司 | Synthesis method of (methyl) acrylic acid alkyl ester |
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| CN108102083A (en) * | 2016-11-24 | 2018-06-01 | 上海东大化学有限公司 | A kind of cithrol and preparation method thereof |
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