A method for synthesizing long-chain alkyl glycol compounds
By using specific dodecano chain length and methyl epoxy propionate as raw materials in the synthesis of long-chain alkylglycol compounds, loop opening and chain-enhancing reactions are carried out, and the mildness and texture problems of existing products are solved through alkaline hydrolysis and pH adjustment, high yield and high-quality product preparation are achieved, and production costs are reduced.
Patent Information
- Application Number
- CN202411965885.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-12-30
- Publication Date
- 2025-04-04
AI Technical Summary
The existing long-chain alkylglycol compound surfactants have structural and technical problems, resulting in poor mildness and poor skin conditioning and moisturizing properties, poor appearance texture, complex process routes and low conversion yields, which increase production and consumption costs.
By using the twelve carbon chain length as the starting material, the ring opening and chain extension reaction is carried out, combined with the hydrolysis reaction under alkaline conditions, the pH value is adjusted, and high-yield and high-quality long-chain alkylglycol compounds are obtained.
It has achieved optimization of product structure, improved color and purity, simplified process routes, improved yield and quality stability, reduced production costs, and enhanced the gentleness of the product and skin conditioning effect.
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Figure BDA0005218337750000021
Abstract
Description
Technical Field
[0001] The invention belongs to the field of cosmetics industry and mainly relates to a method for synthesizing a novel surfactant long-chain alkyl glycol compound. Technical Background
[0002] In recent years, with the continuous development and progress of the cosmetics industry, surfactant products have been widely used. Initially, surfactants were mainly used in the textile industry in the 1930s and 1940s. They were used in the cosmetics industry in the 1950s. After entering the 1980s, due to the change in mass consumption concepts, traditional surfactants could no longer meet people's growing needs. People began to prefer surfactant products with milder properties, better skin feel, foam quality, conditioning properties and environmental effects as alternatives.
[0003] Studies have shown that long-chain alkyl glycol compounds do not interfere with the skin's water metabolism and resistance, and have strong foaming and washing properties. This makes this type of surfactant a high-quality surfactant that combines mildness, safety, biodegradability and versatility in application, and is an ideal cosmetic component.
[0004] Currently, this type of related series of products are being mass-produced in developed countries such as Europe and the United States. However, most of the product molecular chain lengths are alkyl products with less than twelve carbon atoms, which have poor mildness and skin conditioning and moisturizing properties. At the same time, most products are yellow or dark yellow in appearance and have poor texture. The process route is relatively complicated and the product conversion yield is low, which increases the production and manufacturing costs of the enterprise and indirectly increases the purchase cost of consumers, which is not conducive to long-term stable market development.
[0005] Therefore, in view of the above problems, the present invention provides a new technical solution. Summary of the invention
[0006] In order to solve some problems existing in the structure and technology of the above-mentioned products, the present invention proposes a method for synthesizing a novel long-chain alkyl glycol compound, which uses a specific twelve-carbon chain length as a starting material, and carries out a ring-opening reaction with a methyl epoxypropionate structure under the action of a catalyst, and cleverly carries out a chain extension reaction on the structure, and further obtains a product acid structure through a hydrolysis reaction under alkaline conditions, and then adjusts the pH value through an alkali, so as to obtain the target compound of the present application with high yield and high quality.
[0007] The process route method of the present application is simple and controllable, with high yield and stable quality, which is conducive to the synthesis and preparation of products with the same structure and is easy to realize industrial production. At the same time, the color and purity of the product have been greatly improved.
[0008] The specific steps of the method for preparing the target compound of long-chain alkyl glycol in this application are as follows:
[0009] S1: adding dodecyl alcohol and methyl 2,3-epoxypropionate to a first reaction bottle containing a solvent, and heating the reaction under the action of a catalyst to obtain methyl lauryl hydroxypropionate;
[0010] S2: adding the lauryl hydroxypropionic acid methyl ester product obtained in step S1 to a second reaction bottle containing ethanol, then adding a base to the second reaction bottle, heating and refluxing to react, and after the reaction is completed, adjusting the pH value of the reaction solution with an acid to be acidic, thereby preparing lauryl hydroxypropionic acid;
[0011] S3: putting the lauryl hydroxypropionic acid obtained in step S2 into a third reaction bottle containing water, and then adjusting the pH value to a range of 8.5-11.5 with a certain amount of sodium hydroxide solution to obtain sodium lauryl glycol propionate, i.e., the target long-chain alkyl glycol compound;
[0012] Wherein, in step S1, the solvent is chloroform; the catalyst is ferric chloride;
[0013] In step S2, the base is one or more of potassium hydroxide and sodium hydroxide;
[0014] The acid is one or more of hydrochloric acid and sulfuric acid.
[0015] Reaction equation of the present invention is as follows:
[0016]
[0017] As a preferred embodiment of the present invention, in step S1, the molar ratio of dodecyl alcohol, methyl 2,3-epoxypropionate and catalyst is 1:(1-1.2):0.001.
[0018] As a preferred embodiment of the present invention, in step S2, the molar ratio of methyl lauryl hydroxypropionate, base and acid is 1:1.5:2.
[0019] As a preferred embodiment of the present invention, in step S3, the molar ratio of lauryl hydroxypropionic acid to sodium hydroxide is 1:1.1.
[0020] As a preferred embodiment of the present invention, in step S1, the temperature range of the heating is 70°C to 90°C.
[0021] As a preferred embodiment of the present invention, in step S1, after the reaction is completed, the temperature is lowered, a proper amount of water is added, stirred and separated, the organic phase is washed with water, and concentrated to remove the solvent to obtain methyl lauryl hydroxypropionate.
[0022] As a preferred embodiment of the present invention, in step S2, after the heating reflux reaction is completed, the temperature is lowered, ethanol is distilled off, a certain amount of water is added and the temperature is raised to 70°C to 90°C, acidified with acid, allowed to stand for stratification, the oil layer is washed with an appropriate amount of water, and the temperature is lowered to obtain the product lauryl hydroxypropionic acid. More preferably, a certain amount of water is added and the temperature is raised to 80°C.
[0023] As a preferred embodiment of the present invention, in step S3, after lauryl hydroxypropionic acid is added to the third reaction bottle, the temperature is raised to 70°C to 90°C, and the pH value is adjusted to a range of 8.5-11.5 with sodium hydroxide to obtain a long-chain alkyl glycol target compound. Further preferably, after lauryl hydroxypropionic acid is added to the third reaction bottle, the temperature is raised to 80°C. DETAILED DESCRIPTION
[0024] The present invention is further described below in conjunction with the embodiments, and the technical solutions in the embodiments of the present invention are clearly and completely described. Obviously, the described embodiments are only part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.
[0025] Example 1 Synthesis of Sodium Lauryl Glycol Propionate
[0026] 1. Add 10g (53.7mmol) of dodecyl alcohol to a 250mL three-necked flask, then add 100mL of chloroform, heat until dissolved, then add 6.57g (64.44mmol) of methyl 2,3-epoxypropionate and 0.5g (0.054mmol) of ferric chloride, stir evenly, heat to 80°C, and monitor the reaction in liquid phase until it is finished. Cool down, add appropriate amount of water, stir and layer, wash the organic phase with water twice, concentrate and remove the solvent, and obtain 14.7g (50.01mmol) of solid, with a molar yield of 95%. The solid does not need to be purified and is directly used in the next step of the reaction.
[0027] 2. Add 14.7 g (50.01 mmol) of solid lauryl hydroxypropionic acid methyl ester obtained in the first step into a second reaction bottle containing a certain amount of ethanol aqueous solution (25% vol), and then add 3 g (75.01 mmol) of sodium hydroxide, heat to reflux, maintain reflux for 1-2 hours, cool, distill to remove ethanol, add a certain amount of water and raise the temperature to 80°C, acidify with 9.88 g (100.02 mmol) of hydrochloric acid, stand and separate, wash the oil layer twice with an appropriate amount of water, cool to obtain 12.62 g (46.01 mmol) of lauryl hydroxypropionic acid, and the molar yield is 92%.
[0028] 1H-NMR (CDCl3): δ4.82 (t, J = 6.1, 1H), 4.02 (m, 2H), 3.89 (t, J = 6.3, 2H), 1.65-1.42 (m, 2H), 1.28-1.26 (m, 18H), 0.89 (t, J = 6.3, 3H).
[0029] 3. Add 12.62 g (46.01 mmol) of the reactant lauryl hydroxypropionic acid in step 2 into a third reaction bottle containing an appropriate amount of water, heat to 80°C, adjust the pH value to 8.5-11.5 with 2.02 g (50.6 mmol) of sodium hydroxide, and after the pH value stabilizes, add a certain amount of water to prepare a 30% aqueous solution. The inventive compound sodium lauryl glycol propionate solution is obtained.
[0030] Example 2 Synthesis of Sodium Lauryl Glycol Propionate
[0031] 1. Add 10g (53.7mmol) of dodecyl alcohol to a 250mL three-necked flask, then add 100mL of chloroform, heat until dissolved, then add 5.48g (53.7mmol) of methyl 2,3-epoxypropionate and 0.5g (0.054mmol) of ferric chloride, stir evenly, heat to 80°C, and monitor the reaction in liquid phase until it is finished. Cool down, add appropriate amount of water, stir and layer, wash the organic phase with water twice, concentrate and remove the solvent, and obtain 14.25g (49.4mmol) of solid, with a molar yield of 92%. The solid does not need to be purified and is directly used in the next step of the reaction.
[0032] 2. Add 14.7 g (50.01 mmol) of solid lauryl hydroxypropionic acid methyl ester obtained in the first step into a second reaction bottle containing a certain amount of ethanol aqueous solution (25% vol), and then add 4.2 g (75.01 mmol) of potassium hydroxide, heat to reflux, maintain reflux for 1-2 hours, cool, distill to remove ethanol, add a certain amount of water and raise the temperature to 80°C, acidify with 5.0 g (50.01 mmol) of sulfuric acid, stand and separate, wash the oil layer twice with an appropriate amount of water, cool to obtain 13.03 g (47.5 mmol) of product lauryl hydroxypropionic acid, and the molar yield is 95%.
[0033] 1H-NMR (CDCl3): δ4.82 (t, J = 6.1, 1H), 4.02 (m, 2H), 3.89 (t, J = 6.3, 2H), 1.65-1.42 (m, 2H), 1.28-1.26 (m, 18H), 0.89 (t, J = 6.3, 3H).
[0034] 3. Add 13.03 g (47.5 mmol) of the reactant lauryl hydroxypropionic acid in step 2 into a third reaction bottle containing an appropriate amount of water, heat to 80°C, adjust the pH value to 8.5-11.5 with 2.09 g (52.2 mmol) of sodium hydroxide, and after the pH value stabilizes, add a certain amount of water to prepare a 30% aqueous solution. This is to obtain the inventive compound sodium lauryl glycol propionate solution.
[0035] Although the embodiments of the present invention have been shown and described above, it will be understood that the above embodiments are exemplary and are not to be construed as limitations on the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention shall be included in the scope of protection of the present invention.
Claims
1. A method for synthesizing a long-chain alkyl glycol compound, characterized in that: The steps include: S1: adding dodecyl alcohol and methyl 2,3-epoxypropionate to a first reaction bottle containing a solvent, and heating the reaction under the action of a catalyst to obtain methyl lauryl hydroxypropionate; S2: adding the lauryl hydroxypropionic acid methyl ester product obtained in step S1 to a second reaction bottle containing ethanol, then adding a base to the second reaction bottle, heating and refluxing to react, and after the reaction is completed, adjusting the pH value of the reaction solution with an acid to be acidic, thereby preparing lauryl hydroxypropionic acid; S3: putting the lauryl hydroxypropionic acid obtained in step S2 into a third reaction bottle containing water, and then adjusting the pH value to a range of 8.5-11.5 with a certain amount of sodium hydroxide solution to obtain sodium lauryl glycol propionate, i.e., the target long-chain alkyl glycol compound; Wherein, in step S1, the solvent is chloroform; the catalyst is ferric chloride; In step S2, the base is one or more of potassium hydroxide and sodium hydroxide; The acid is one or more of hydrochloric acid and sulfuric acid.
2. The synthesis method according to claim 1, characterized in that In step S1, the molar ratio of dodecyl alcohol, methyl 2,3-epoxypropionate and catalyst is 1:(1-1.2):0.
001.
3. The synthesis method according to claim 1, characterized in that In step S2, the molar ratio of methyl lauryl hydroxypropionate, base and acid is 1:1.5:
2.
4. The synthesis method according to claim 1, characterized in that In step S3, the molar ratio of lauryl hydroxypropionic acid to sodium hydroxide is 1:1.
1.
5. The synthesis method according to claim 1, characterized in that In step S1, the temperature range of the heating is 70°C to 90°C.
6. The synthesis method according to claim 1 or 5, characterized in that: In step S1, after the reaction is completed, the temperature is lowered, an appropriate amount of water is added, stirred and separated, the organic phase is washed with water, and concentrated to remove the solvent to obtain methyl lauryl hydroxypropionate.
7. The synthesis method according to claim 1, characterized in that In step S2, after the heating reflux reaction is completed, the temperature is lowered, ethanol is distilled off, a certain amount of water is added and the temperature is raised to 70° C. to 90° C., the mixture is acidified with an acid, and the mixture is allowed to stand for stratification, the oil layer is washed with an appropriate amount of water, and the temperature is lowered to obtain the product lauryl hydroxypropionic acid.
8. The synthesis method according to claim 1, characterized in that In step S3, after lauryl hydroxypropionic acid is added to the third reaction bottle, the temperature is raised to 70° C. to 90° C., and the pH value is adjusted to the range of 8.5-11.5 with sodium hydroxide to obtain the target long-chain alkyl glycol compound.