CN114702396A - Preparation method of PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt - Google Patents
Preparation method of PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt Download PDFInfo
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- CN114702396A CN114702396A CN202210501767.7A CN202210501767A CN114702396A CN 114702396 A CN114702396 A CN 114702396A CN 202210501767 A CN202210501767 A CN 202210501767A CN 114702396 A CN114702396 A CN 114702396A
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- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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Abstract
The invention discloses a preparation method of PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt, belonging to the technical field of chemical synthesis. A preparation method of PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt comprises the following steps: s1, taking PEG-6 glycerol polyoxyethylene ether and epichlorohydrin as raw materials, adding a catalyst sulfuric acid, and reacting at 50-100 ℃ for 1-5 hours to obtain PEG-6 chloroglycerol polyoxyethylene ether; s2, mixing the PEG-6 chloro-glycerol polyoxyethylene ether obtained in the step S1 with hexadecyl/octadecyl dimethyl tertiary amine, and reacting for 3-9 hours at 50-100 ℃ by taking water as a solvent to obtain a mixture containing PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt; the method can realize the synthesis of the PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt, and has the advantages of simple operation, high yield and high selectivity.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt.
Background
The quaternary ammonium salt cationic surfactant has the advantages of high surface activity, strong synergistic effect, good antibacterial and antistatic capabilities and the like, is used in high and new technical fields of daily chemical industry, new material manufacturing, life science, biotechnology, nano materials and the like, and is widely used as an effective emulsifier, a bactericide, an antistatic agent, a dispersing agent, a defoaming agent and the like.
When the concentration of a mixed system exceeds cmc when a cationic surfactant and an anionic surfactant are compounded, the mixed system can generate precipitation or phase separation due to strong electrostatic interaction between anions and cations, and the concentration of the phase separation of some systems is even lower than the cmc, so that various application performances of sterilization, antistatic property, emulsification and the like of the mixed system are lost, which is a problem that the industry of the surfactants is difficult to solve. More Ethylene Oxide (EO) groups are introduced into the molecules of the anionic or cationic surfactant, so that the problems can be effectively solved, and the surfactant for realizing the cationic characteristic can be compounded with the anionic surfactant for use, so that the surface activity of the surfactant is improved. The insertion of polyoxyethylene chains (EO chains) into the surfactant molecule can also significantly improve water solubility, for example, typical anionic surfactants alkyl polyoxyethylene ether sulfates (AES), alkyl polyoxyethylene ether carboxylates (AEC). And the addition of ionic groups to the nonionic surfactant molecules can increase the surfactant's surface activity and cloud point temperature. The glycerol polyoxyethylene ether quaternary ammonium salt has the excellent properties of nonionic and cationic surfactants, and has the following structural formula:
wherein the average number of the sum of the EO numbers m, n and p is 6, and R is hexadecyl dimethyl tertiary amine or octadecyl dimethyl tertiary amine. However, it is complicated to introduce an EO group into a cationic surfactant molecule, and particularly a cationic surfactant having an EO number exceeding 3 is more difficult to synthesize. Meanwhile, the glycerol polyoxyethylene ether has three polyoxyethylene chains, and the chain number of the ring-opening reaction between the polyoxyethylene ether chain and the epichlorohydrin is more difficult to control.
Disclosure of Invention
The invention aims to solve the technical problem of providing a preparation method of PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt, which can realize simple operation, high yield and high selectivity when synthesizing the PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt.
The synthetic route of the invention is as follows:
the synthesis preparation method of the PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt comprises the following steps:
s1, taking PEG-6 glycerol polyoxyethylene ether and epichlorohydrin as raw materials, adding a catalyst sulfuric acid, and reacting at 50-100 ℃ for 1-5 hours to obtain PEG-6 chloroglycerol polyoxyethylene ether;
s2, mixing the PEG-6 chloro-glycerol polyoxyethylene ether obtained in the step S1 with hexadecyl/octadecyl dimethyl tertiary amine, and reacting for 3-9 hours at 50-100 ℃ by taking water as a solvent to obtain a mixture containing PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt;
further, in step S1, the molar ratio of the PEG-6 glycerol polyoxyethylene ether to the epichlorohydrin is 1-5: 1.
Further, in step S1, the molar ratio of the catalyst sulfuric acid to the PEG-6 glycerol polyoxyethylene ether is 1: 100 to 500.
Further, in step S2, the molar ratio of the PEG-6 chlorohydrin polyoxyethylene ether to the hexadecyl/octadecyl dimethyl tertiary amine is 1 to 2: 1.
Further, in step S2, the amount of solvent water is 1 to 5 ml/g PEG-6 chlorohydrin polyoxyethylene ether.
The invention has the beneficial effects that: compared with the prior art, the PEG-6 glycerol polyoxyethylene ether reacts with epichlorohydrin under the action of a catalyst to obtain PEG-6 chloroglycerol polyoxyethylene ether (the yield is more than 85%), and then the PEG-6 chloroglycerol polyoxyethylene ether and hexadecyl/octadecyl dimethyl tertiary amine are dissolved in water and react to obtain the PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt (the tertiary amine conversion rate is more than 95%). Therefore, the total yield of the PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt synthesized by the method is over 75 percent. Therefore, the method has the advantages of convenient operation, high yield and low cost.
Drawings
FIG. 1 is a flow chart of the architecture of the present invention;
FIG. 2 is an infrared spectrum of PEG-6 glyceryl polyoxyethylene ether quaternary ammonium salt prepared in the example of the present invention;
FIG. 3 is a mass spectrum of PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt prepared in the example of the present invention; where M/z 682 is the highest point, and the difference of 44 is used to spread toward the lower part, which is [ M + H ]]+The peak of (2) is a product peak.
Detailed Description
In order to more clearly illustrate the technical solution of the present invention, the following detailed description is made with reference to the accompanying drawings:
a preparation method for synthesizing PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt comprises the following specific operation steps:
s1, taking PEG-6 glycerol polyoxyethylene ether and epichlorohydrin as raw materials, adding a catalyst sulfuric acid, and reacting at 60-90 ℃ for 2-4 hours to obtain PEG-6 chloroglycerol polyoxyethylene ether;
s2, mixing the PEG-6 chloro-glycerol polyoxyethylene ether obtained in the step S1 with hexadecyl/octadecyl dimethyl tertiary amine, and reacting for 4-8 hours at 80-100 ℃ by using water as a solvent to obtain a mixture containing PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt;
further, in step S1, the molar ratio of the PEG-6 glycerol polyoxyethylene ether to the epichlorohydrin is 1-3: 1.
Further, in step S1, the molar ratio of the catalyst sulfuric acid to the PEG-6 glycerol polyoxyethylene ether is 1: 100-300.
Further, in step S2, the molar ratio of the PEG-6-chloroglycerol polyoxyethylene ether to the hexadecyl/octadecyl dimethyl tertiary amine is 1-1.5: 1.
Further, in step S2, the amount of the solvent water is 1 to 3 ml/g PEG-6 chlorohydrin polyoxyethylene ether.
Example 1:
mixing PEG-6 glycerol polyoxyethylene ether (33.64g, 0.15mol) and epichlorohydrin (4.63g, 0.05mol), adding sulfuric acid (0.0054mL, 0.0001mol), stirring at 60 ℃ for reaction for 4 hours to obtain a light yellow transparent viscous liquid, and distilling the light yellow reaction liquid under reduced pressure to obtain 13.70g of PEG-6 glycerol polyoxyethylene ether (light yellow liquid) with the yield of 86.52%.
The PEG-6 chloro-glycerol polyoxyethylene ether (23.76g, 0.075mol) obtained above and hexadecyl/octadecyl dimethyl tertiary amine (14.18g, 0.05mol) are mixed, dissolved in 40 ml of water, and stirred and reacted for 8 hours at 80 ℃ to obtain a light yellow transparent viscous liquid, thus obtaining 28.58g of PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt and 96.83% of tertiary amine conversion rate.
Example 2:
PEG-6 glycerol polyoxyethylene ether (22.43g, 0.1mol) and epichlorohydrin (4.63g, 0.05mol) are mixed, sulfuric acid (0.0054mL, 0.0001mol) is added, stirring is carried out at 75 ℃ for reaction for 3 hours, the system is light yellow transparent viscous liquid, the light yellow reaction liquid is subjected to reduced pressure distillation, 14.21g of PEG-6 glycerol polyoxyethylene ether (light yellow liquid) is obtained, and the yield is 89.72%.
Mixing the PEG-6 chloro-glycerol polyoxyethylene ether (19.79g, 0.0625mol) obtained above with hexadecyl/octadecyl dimethyl tertiary amine (14.18g, 0.05mol), dissolving in 40 ml of water, stirring and reacting at 90 ℃ for 6 hours, wherein the system is a light yellow transparent viscous liquid, and the PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt is obtained, wherein the conversion rate of the tertiary amine is 97.31%.
Example 3:
PEG-6 glycerol polyoxyethylene ether (11.21g, 0.105mol) and epichlorohydrin (4.63g, 0.05mol) are mixed, sulfuric acid (0.0054mL, 0.0001mol) is added, the mixture is stirred and reacted for 2 hours at 90 ℃, the system is light yellow transparent viscous liquid, the light yellow reaction liquid is subjected to reduced pressure distillation to obtain 14.69g of PEG-6 glycerol polyoxyethylene ether (light yellow liquid), and the yield is 92.75%.
The PEG-6 chloro-glycerol polyoxyethylene ether (15.84g, 0.05mol) obtained above and hexadecyl/octadecyl dimethyl tertiary amine (14.18g, 0.05mol) are mixed, dissolved in 40 ml of water, stirred and reacted for 4 hours at 100 ℃, and the system is light yellow transparent viscous liquid, thus obtaining 29.41g of PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt and the conversion rate of the tertiary amine is 98.56%.
Finally, it should be understood that the embodiments described herein are merely illustrative of the principles of embodiments of the present invention; other variations are possible within the scope of the invention; thus, by way of example, and not limitation, alternative configurations of embodiments of the invention may be considered consistent with the teachings of the present invention; accordingly, the embodiments of the invention are not limited to the embodiments explicitly described and depicted.
Claims (5)
1. A preparation method of PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt is characterized by comprising the following specific operation steps:
s1, taking PEG-6 glycerol polyoxyethylene ether and epichlorohydrin as raw materials, adding a catalyst sulfuric acid, and reacting at 50-100 ℃ for 1-5 hours to obtain PEG-6 chloroglycerol polyoxyethylene ether;
s2, mixing the PEG-6 chloro-glycerol polyoxyethylene ether obtained in the step S1 with hexadecyl/octadecyl dimethyl tertiary amine, and reacting for 3-9 hours at 50-100 ℃ by taking water as a solvent to obtain a mixture containing PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt.
2. The method for preparing the PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt according to the claim 1, wherein in the step S1, the molar ratio of the PEG-6 glycerol polyoxyethylene ether to the epichlorohydrin is 1-5: 1.
3. The method for preparing PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt according to claim 1, wherein in step S1, the molar ratio of the catalyst sulfuric acid to PEG-6 glycerol polyoxyethylene ether is 1: 100 to 500.
4. The method for preparing the PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt according to the claim 1, wherein in the step S2, the molar ratio of the PEG-6 chloroglycerol polyoxyethylene ether to the hexadecyl/octadecyl dimethyl tertiary amine is 2-1: 1.
5. The method for preparing the PEG-6 glycerol polyoxyethylene ether quaternary ammonium salt according to the claim 1, wherein in the step S2, the amount of the solvent water is 1-5 ml/g PEG-6 chloro glycerol polyoxyethylene ether.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115354417A (en) * | 2022-09-23 | 2022-11-18 | 浙江鹿达科技有限公司 | Preparation method of chemical fiber spinning oil containing antistatic agent |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1296351A (en) * | 1968-06-25 | 1972-11-15 | ||
| US5681643A (en) * | 1994-10-13 | 1997-10-28 | Canon Kabushiki Kaisha | Active energy ray-curable composition, recording medium and image-forming method employing the same |
| CN1903419A (en) * | 2006-07-07 | 2007-01-31 | 太原理工大学 | Polyoxyethylene chain three cation quaternary ammonium salt type surfactant and its sysnthesis method |
| CN102935343A (en) * | 2012-11-08 | 2013-02-20 | 中国林业科学研究院林产化学工业研究所 | Abietate alcohol ether type quaternary ammonium salt surface active agent and preparation method thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1296351A (en) * | 1968-06-25 | 1972-11-15 | ||
| US5681643A (en) * | 1994-10-13 | 1997-10-28 | Canon Kabushiki Kaisha | Active energy ray-curable composition, recording medium and image-forming method employing the same |
| CN1903419A (en) * | 2006-07-07 | 2007-01-31 | 太原理工大学 | Polyoxyethylene chain three cation quaternary ammonium salt type surfactant and its sysnthesis method |
| CN102935343A (en) * | 2012-11-08 | 2013-02-20 | 中国林业科学研究院林产化学工业研究所 | Abietate alcohol ether type quaternary ammonium salt surface active agent and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115354417A (en) * | 2022-09-23 | 2022-11-18 | 浙江鹿达科技有限公司 | Preparation method of chemical fiber spinning oil containing antistatic agent |
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