CN115785025A - Preparation method of dodecyl glycidyl ether - Google Patents
Preparation method of dodecyl glycidyl ether Download PDFInfo
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- CN115785025A CN115785025A CN202211599575.0A CN202211599575A CN115785025A CN 115785025 A CN115785025 A CN 115785025A CN 202211599575 A CN202211599575 A CN 202211599575A CN 115785025 A CN115785025 A CN 115785025A
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Abstract
The invention provides a preparation method of dodecyl glycidyl ether, belonging to the technical field of organic synthesis. According to the invention, excessive 1-dodecanol is adopted to react with epoxy chloropropane, so that side reaction is avoided, and after pre-reaction, residual 1-dodecanol and epoxy chloropropane are recovered through reduced pressure distillation and stripping, so that the product purity is effectively improved, and the content of hydrolytic chlorine is reduced; the invention uses acid catalyst and phase transfer catalyst, which ensures higher reaction activity and selectivity of etherification and ring-closure reaction, and the intermediate product chlorohydrin ether is added with alkali to carry out ring-closure reaction in the presence of phase transfer catalyst, thus improving product purity and yield and shortening reaction time. The results of the examples show that the content of the hydrolyzed chlorine of the dodecyl glycidyl ether obtained by the method of the invention is 476-561 ppm, and the purity is 94-96%.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of dodecyl glycidyl ether.
Background
Dodecyl glycidyl ether is an epoxy reactive diluent, is a colorless transparent liquid, and has the advantages of high boiling point, difficult volatilization, low toxicity and good chemical stability. Structurally, the 1-dodecanol has a longer carbon chain, a higher boiling point and good thermal stability. The dodecyl glycidyl ether has good dilution effect, small volatility, low viscosity and good flexibility, and has unique application in the aspects of fabric finishing agents, epoxy diluents, chloride stabilizers, epoxy curing agents and the like.
For the synthesis of dodecyl glycidyl ether, a two-step process is usually adopted, epoxy chloropropane and dodecanol are subjected to a ring opening reaction under the action of an acid catalyst to generate a chlorohydrin ether intermediate, then chlorohydrin ether and sodium hydroxide are subjected to a ring closing reaction, and the product is subjected to solid-liquid separation, water washing, refining and other processes to obtain the product. The reaction equation is as follows:
etherification:
the problems of low reaction activity, high hydrolysis chlorine and the like generally exist in the preparation of the existing dodecyl glycidyl ether. In the synthesis method of dodecyl glycidyl ether, secondary hydroxyl of chlorohydrin ether which is an intermediate product of a Lewis acid catalytic method competitively participates in ring-opening addition reaction of an epoxy group to generate a chain growth byproduct. When 1-dodecanol with equivalent weight is used for reacting with epichlorohydrin, a large amount of raw material 1-dodecanol remains in the product due to the generation of chain growth by-products and the low reactivity of 1-dodecanol, even if excessive epoxide is used for the reaction, the residual of raw material 1-dodecanol cannot be completely eliminated, the purity of the product is low, and the epoxide number of the product is further reduced.
Disclosure of Invention
In view of this, the present invention aims to provide a method for preparing dodecyl glycidyl ether, and the method provided by the present invention has the advantages of high reaction activity, high purity of the obtained dodecyl glycidyl ether, and low content of hydrolysis chlorine.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a preparation method of dodecyl glycidyl ether, which comprises the following steps:
mixing 1-dodecanol, epichlorohydrin and Lewis acid catalyst, carrying out etherification ring-opening reaction, carrying out reduced pressure distillation on the obtained etherification ring-opening reaction liquid, and recovering unreacted epichlorohydrin and 1-dodecanol to obtain intermediate epichlorohydrin dodecyl ether; the mol ratio of the 1-dodecanol to the epichlorohydrin is 1.05-1.4;
and mixing the intermediate epichlorohydrin dodecyl ether with a phase transfer catalyst and an inorganic alkali liquor, and carrying out a ring-closing reaction under a vacuum condition to obtain dodecyl glycidyl ether.
Preferably, the Lewis acid catalyst is one or more of stannic chloride, zinc perchlorate, boron trifluoride diethyl etherate, ferric trichloride and aluminum trichloride;
the mass of the Lewis acid catalyst is 0.5-2% of that of the 1-dodecanol.
Preferably, the temperature of the etherification ring-opening reaction is 60-110 ℃ and the time is 1-7 h.
Preferably, the temperature of the reduced pressure distillation is 90-110 ℃, and the vacuum degree is 90-95 kPa.
Preferably, the phase transfer catalyst is a quaternary ammonium salt;
the mass of the phase transfer catalyst is 0.5-2% of that of the 1-dodecanol.
Preferably, the quaternary ammonium salt is one or more of tetraethylammonium bromide, benzyltrimethylammonium bromide, benzyltriethylammonium chloride, benzyltriethylammonium bromide and tetrabutylammonium bromide.
Preferably, the molar ratio of the inorganic base to the epichlorohydrin in the inorganic alkali liquid is 0.8-1.5.
Preferably, the inorganic alkali solution is NaOH solution and/or KOH solution;
the mass concentration of the inorganic alkali liquor is 30-50%.
Preferably, the temperature of the ring closure reaction is 60-90 ℃, the time is 3-6 h, and the vacuum degree is 81-98 kPa.
Preferably, after the ring-closure reaction, the method further comprises performing post-treatment on the obtained ring-closure reaction solution, wherein the post-treatment comprises:
and (3) washing, neutralizing and dehydrating the closed-loop reaction solution to obtain a pure dodecyl glycidyl ether product.
The invention provides a preparation method of dodecyl glycidyl ether, which comprises the following steps: mixing 1-dodecanol, epichlorohydrin and Lewis acid catalyst, carrying out etherification ring-opening reaction, carrying out reduced pressure distillation on the obtained etherification ring-opening reaction liquid, and recovering unreacted epichlorohydrin and 1-dodecanol to obtain intermediate epichlorohydrin dodecyl ether; the molar ratio of the 1-dodecanol to the epichlorohydrin is 1.05-1.4; and mixing the intermediate epichlorohydrin dodecyl ether with a phase transfer catalyst and an inorganic alkali liquor, and carrying out a ring-closing reaction under a vacuum condition to obtain dodecyl glycidyl ether. According to the invention, excessive 1-dodecanol is adopted to react with epichlorohydrin, so that side reaction is avoided, and after pre-reaction, residual 1-dodecanol and epichlorohydrin are recovered through reduced pressure distillation and stripping, so that the product purity is effectively improved, and the content of hydrolysis chlorine is reduced; the invention uses acid catalyst and phase transfer catalyst, which ensures higher reaction activity and selectivity of etherification and ring-closure reaction, and the intermediate product chlorohydrin ether is added with alkali to carry out ring-closure reaction in the presence of phase transfer catalyst, thus improving product purity and yield and shortening reaction time. The results of the examples show that the content of the hydrolyzed chlorine of the dodecyl glycidyl ether obtained by the method of the invention is 476-561 ppm, and the purity is 94-96%.
Detailed Description
The invention provides a preparation method of dodecyl glycidyl ether, which comprises the following steps:
mixing 1-dodecanol, epichlorohydrin and Lewis acid catalyst, carrying out etherification ring-opening reaction, carrying out reduced pressure distillation on the obtained etherification ring-opening reaction liquid, and recovering unreacted epichlorohydrin and 1-dodecanol to obtain intermediate epichlorohydrin dodecyl ether; the mol ratio of the 1-dodecanol to the epichlorohydrin is 1:1.05 to 1.4;
and mixing the intermediate epichlorohydrin dodecyl ether with a phase transfer catalyst and an inorganic alkali liquor, and carrying out a ring-closing reaction under a vacuum condition to obtain dodecyl glycidyl ether.
The invention mixes 1-dodecanol, epichlorohydrin and Lewis acid catalyst to carry out etherification ring-opening reaction. In the present invention, the molar ratio of the 1-dodecanol to the epichlorohydrin is preferably 1.05 to 1.4, preferably 1.1 to 1.3.
In the invention, the Lewis acid catalyst is preferably one or more of tin tetrachloride, zinc perchlorate, boron trifluoride diethyl etherate, ferric trichloride and aluminum trichloride; the mass of the Lewis acid catalyst is 0.5-2% of that of the 1-dodecanol.
In the present invention, the mixing is preferably performed in the following manner: mixing 1-dodecanol with Lewis acid catalyst, heating to etherifying ring-opening reaction temp, and dropping epoxy chloropropane. In the present invention, the dripping time of the epichlorohydrin is preferably 1 to 4 hours, and more preferably 2 to 3 hours. The invention starts to calculate the time of etherification ring-opening reaction after the addition of the epichlorohydrin is finished.
In the present invention, the temperature of the etherification ring-opening reaction is preferably 60 to 110 ℃, more preferably 80 to 100 ℃, and the time is preferably 1 to 7 hours, more preferably 2 to 5 hours.
After the etherification ring-opening reaction, the obtained etherification ring-opening reaction liquid is subjected to reduced pressure distillation, and unreacted epichlorohydrin and 1-dodecanol are recovered to obtain intermediate epichlorohydrin dodecyl ether. In the present invention, the temperature of the reduced pressure distillation is preferably 90 to 110 ℃, more preferably 100 ℃, and the degree of vacuum is preferably 90 to 95kPa, more preferably 92 to 94kPa. The invention carries out the reduced pressure distillation until the temperature reaches 90 to 110 ℃, and the epichlorohydrin and the 1-dodecanol are not evaporated under the vacuum degree of 90 to 95kPa, thereby obtaining the intermediate epichlorohydrin dodecyl ether.
The invention mixes the intermediate epichlorohydrin dodecyl ether with a phase transfer catalyst and an inorganic alkali liquor, and carries out a ring-closing reaction under a vacuum condition to obtain the dodecyl glycidyl ether. In the present invention, the phase transfer catalyst is preferably a quaternary ammonium salt, and more preferably one or more of tetraethylammonium bromide, benzyltrimethylammonium bromide, benzyltriethylammonium chloride, benzyltriethylammonium bromide and tetrabutylammonium bromide. In the present invention, the mass of the phase transfer catalyst is preferably 0.5 to 2%, more preferably 1 to 1.5% of the mass of 1-dodecanol.
In the present invention, the molar ratio of the inorganic base to the epichlorohydrin in the inorganic alkaline solution is preferably 0.8 to 1.5, and more preferably 1 to 1.2. In the invention, the inorganic alkali solution is preferably NaOH solution and/or KOH solution; the mass concentration of the inorganic alkali liquor is preferably 30-50%, and more preferably 35-45%. In the present invention, the inorganic alkali solution is preferably added dropwise, and the dropwise addition time is preferably 1 to 3.5 hours, and more preferably 2 to 3 hours.
In the present invention, the temperature of the ring closure reaction is preferably 60 to 90 ℃, more preferably 70 to 80 ℃; the time is preferably 3 to 6 hours, and more preferably 4 to 5 hours; the degree of vacuum is preferably 81 to 98kPa, more preferably 85 to 95kPa.
In the present invention, after the ring-closure reaction, the method further comprises performing post-treatment on the obtained ring-closure reaction solution, wherein the post-treatment comprises:
and (3) washing, neutralizing and dehydrating the closed-loop reaction solution to obtain a pure dodecyl glycidyl ether product.
In the present invention, the temperature of water used for the water washing is preferably 80 ℃.
In the present invention, the acidic reagent used for the neutralization is preferably sodium dihydrogen phosphate. In the present invention, after the neutralization, the pH of the resulting neutralized solution is preferably 6 to 7.
The invention preferably carries out dehydration under vacuum condition; the degree of vacuum for the dehydration is preferably 20Torr, and the temperature is preferably 120 ℃.
The preparation method of dodecyl glycidyl ether provided by the present invention is described in detail with reference to the following examples, but they should not be construed as limiting the scope of the present invention.
Example 1
240 g of 1-dodecanol and 3.2g of stannic chloride are added into a 1L reaction flask, stirred and heated to 60 ℃. Maintaining the reaction temperature at 60 ℃, dropwise adding 152 g of epichlorohydrin within 4 hours, after the dropwise adding is completed, continuously stirring at the temperature for reaction for 7 hours, and after the reaction is finished, carrying out reduced pressure distillation and steam stripping to recover the epichlorohydrin and 1-dodecanol which do not participate in the reaction until the temperature reaches 90-110 ℃, and the vacuum degree reaches 90-95 kPa until no epichlorohydrin and no 1-dodecanol are evaporated out, thereby obtaining intermediate epichlorohydrin dodecyl ether; after the temperature was raised to 90 ℃ and 1.5 g of tetraethylammonium bromide as a phase transfer catalyst was added, 180 g of 32.0% NaOH was added dropwise over 3 hours, and the reaction was continued at the same temperature for 3 hours. Then, 100 g of hot water at 80 ℃ is added, stirring and standing are carried out, the lower layer brine is separated, 200 g of deionized water at 80 ℃ is added, stirring is carried out, 3.2g of sodium dihydrogen phosphate is added to neutralize until the pH value is equal to 6-7, and standing and the lower layer water is separated. Then 200 g of deionized water with the temperature of 80 ℃ is added, stirred and stood, and the lower layer water is removed. Dehydrating and desolventizing under vacuum of 20Torr at 120 ℃ until the water-containing solvent content is less than 1000ppm, and filtering to obtain the dodecyl glycidyl ether product.
Example 2
240 g of 1-dodecanol, 2g of stannic chloride and 2g of zinc perchlorate are added into a 1L reaction bottle, stirred and heated to 110 ℃. Maintaining the reaction temperature at 110 ℃, dropwise adding 130 g of epoxy chloropropane within 3 hours, after the dropwise adding is completed, continuously stirring at the temperature for reaction for 7 hours, and after the reaction is finished, carrying out reduced pressure distillation and steam stripping to recover epoxy chloropropane and 1-dodecanol which do not participate in the reaction until the temperature reaches 90-110 ℃, and the vacuum degree is 90-95 kPa, and no epoxy chloropropane and 1-dodecanol are evaporated out, so as to obtain intermediate surface chlorohydrin ether; after cooling to 80 ℃ and adding 2.4 g of benzyltrimethylammonium bromide as a phase transfer catalyst, 115 g of 50.0% NaOH was added dropwise over 2 hours, and the reaction was continued at the same temperature for 4 hours. Then, 100 g of 80 ℃ hot water is added, stirred and stood to remove the lower layer brine, 200 g of 80 ℃ deionized water is added, stirred, 3.2g of sodium dihydrogen phosphate is added to neutralize until the pH value is equal to 6-7, and the lower layer water is removed after standing. Then 200 g of deionized water with the temperature of 80 ℃ is added, stirred and stood, and the lower layer water is removed. Dehydrating and desolventizing at the temperature of 120 ℃ under the vacuum of 20Torr until the water-containing solvent is less than 1000ppm, and filtering to obtain the dodecyl glycidyl ether product.
Example 3
240 g of 1-dodecanol, 2g of stannic chloride and 2g of boron trifluoride etherate were put into a 1L reaction flask, stirred, and heated to 110 ℃. Maintaining the reaction temperature at 110 ℃, dripping 161 g of epoxy chloropropane within 1 hour, continuing stirring at the temperature for reaction for 1 hour after finishing dripping, performing reduced pressure distillation and steam stripping to recover the epoxy chloropropane and 1-dodecanol which do not participate in the reaction until the temperature reaches 90-110 ℃, and distilling out no epoxy chloropropane and 1-dodecanol under the vacuum degree of 90-95 kPa to obtain the intermediate surface chlorohydrin ether. After cooling to 60 ℃ and adding 3.2g of benzyltriethylammonium bromide as a phase transfer catalyst, 195 g of 48.0% NaOH was added dropwise over 3 hours, and the reaction was continued at the same temperature for 6 hours. Then, 100 g of 80 ℃ hot water is added, stirred and stood to remove the lower layer brine, 200 g of 80 ℃ deionized water is added, stirred, 3.2g of sodium dihydrogen phosphate is added to neutralize until the pH value is equal to 6-7, and the lower layer water is removed after standing. Then 200 g of deionized water with the temperature of 80 ℃ is added, stirred and stood, and the lower layer water is removed. Dehydrating and desolventizing at the temperature of 120 ℃ under the vacuum of 20Torr until the water-containing solvent is less than 1000ppm, and filtering to obtain the dodecyl glycidyl ether product.
Comparative example 1
240 g of 1-dodecanol, 2g of boron trifluoride etherate and 2g of stannic chloride were added into a 1L reaction flask, stirred and heated to 70 ℃. Maintaining the reaction temperature at 70 ℃, dropwise adding 140 g of epoxy chloropropane within 3 hours, and after the dropwise adding is completed, continuously stirring and reacting for 4 hours at 80 ℃ to obtain intermediate body surface chlorohydrin ether. After cooling to 60 ℃ and addition of 2g of tetrabutylammonium bromide as phase transfer catalyst, 198 g of 32.0% NaOH was added dropwise over 3 hours, and the reaction was continued at the same temperature for 3 hours. Then, 100 g of 80 ℃ hot water is added, stirred and stood to remove the lower layer brine, 200 g of 80 ℃ deionized water is added, stirred, 3.2g of sodium dihydrogen phosphate is added to neutralize until the pH value is equal to 6-7, and the lower layer water is removed after standing. Then 200 g of deionized water with the temperature of 80 ℃ is added, stirred and stood, and the lower layer water is removed. Dehydrating and desolventizing at the temperature of 120 ℃ under the vacuum of 20Torr until the water-containing solvent is less than 1000ppm, and filtering to obtain the dodecyl glycidyl ether product.
Comparative example 2
240 g of 1-dodecanol, 2.8g of ferric trichloride and 1.2g of aluminum trichloride are added into a 1L reaction bottle, stirred and heated to 60 ℃. Maintaining the reaction temperature at 75 ℃, dropwise adding 152 g of epichlorohydrin within 3 hours, after the dropwise adding is completed, continuously stirring and reacting for 6 hours at the temperature, carrying out reduced pressure distillation and steam stripping after the reaction is completed, recovering the epichlorohydrin and 1-dodecanol which do not participate in the reaction until the temperature reaches 90-110 ℃, and obtaining intermediate epichlorohydrin dodecyl ether under the vacuum degree of 90-95 kPa until no epichlorohydrin and 1-dodecanol are evaporated; after the temperature was raised to 90 ℃ and 3.5g of zinc perchlorate as a Lewis acid catalyst was added, 165g of 40.0% NaOH was added dropwise over 3 hours, and the reaction was carried out at the same temperature for 5 hours. Then, 100 g of 80 ℃ hot water is added, stirred and stood to remove the lower layer brine, 200 g of 80 ℃ deionized water is added, stirred, 3.2g of sodium dihydrogen phosphate is added to neutralize until the pH value is equal to 6-7, and the lower layer water is removed after standing. Then 200 g of deionized water with the temperature of 80 ℃ is added, stirred and stood, and the lower layer water is removed. Dehydrating and desolventizing at the temperature of 120 ℃ under the vacuum of 20Torr until the water-containing solvent is less than 1000ppm, and filtering to obtain the dodecyl glycidyl ether product.
The color number, epoxy equivalent, hydrolyzed chlorine content, total chlorine content and purity of the dodecyl glycidyl ethers obtained in examples 1 to 3 and comparative examples 1 to 2 were measured, and the results are shown in Table 1. The relevant test methods are as follows:
ISO 21627-3 method for measuring total chlorine;
ASTM D1209-2005 liquid chemical color determination (Hazen units, platinum-cobalt color number);
determination of epoxy equivalent of ASTM D1652-2004 epoxy compounds;
ASTM D1726-2003 determination of epoxy resins and glycidyl ester hydrolysis chlorine.
TABLE 1 results of quality test of products of examples 1 to 3 and comparative examples 1 to 2
As can be seen from Table 1, the dodecyl glycidyl ether obtained by the invention has high purity and low content of hydrolytic chlorine. While the comparative example 1 does not carry out reduced pressure distillation and stripping to recover epoxy chloropropane and 1-dodecanol which do not participate in the reaction, the obtained dodecyl glycidyl ether has low purity and high content of hydrolytic chlorine and total chlorine; comparative example 2 adopts a lewis acid as a ring-closing catalyst, the effect is not obvious, and the ring closure is not sufficient, so that the epoxy equivalent and the hydrolysis chlorine are both higher.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and amendments can be made without departing from the principle of the present invention, and these modifications and amendments should also be considered as the protection scope of the present invention.
Claims (10)
1. A preparation method of dodecyl glycidyl ether comprises the following steps:
mixing 1-dodecanol, epichlorohydrin and Lewis acid catalyst, carrying out etherification ring-opening reaction, carrying out reduced pressure distillation on the obtained etherification ring-opening reaction liquid, and recovering unreacted epichlorohydrin and 1-dodecanol to obtain intermediate epichlorohydrin dodecyl ether; the mol ratio of the 1-dodecanol to the epichlorohydrin is 1.05-1.4;
and mixing the intermediate epichlorohydrin dodecyl ether with a phase transfer catalyst and an inorganic alkali liquor, and carrying out a ring-closing reaction under a vacuum condition to obtain dodecyl glycidyl ether.
2. The preparation method according to claim 1, wherein the Lewis acid catalyst is one or more of tin tetrachloride, zinc perchlorate, boron trifluoride diethyl etherate, ferric trichloride and aluminum trichloride;
the mass of the Lewis acid catalyst is 0.5-2% of that of the 1-dodecanol.
3. The preparation method according to claim 1, wherein the temperature of the etherification ring-opening reaction is 60 to 110 ℃ and the time is 1 to 7 hours.
4. The process according to claim 1 or 3, wherein the temperature of the reduced pressure distillation is 90 to 110 ℃ and the degree of vacuum is 90 to 95kPa.
5. The production method according to claim 1, wherein the phase transfer catalyst is a quaternary ammonium salt;
the mass of the phase transfer catalyst is 0.5-2% of that of the 1-dodecanol.
6. The preparation method according to claim 5, wherein the quaternary ammonium salt is one or more of tetraethylammonium bromide, benzyltrimethylammonium bromide, benzyltriethylammonium chloride, benzyltriethylammonium bromide and tetrabutylammonium bromide.
7. The preparation method according to claim 1, characterized in that the molar ratio of inorganic base to epichlorohydrin in the inorganic alkaline solution is 0.8 to 1.5.
8. The preparation method according to claim 1 or 7, characterized in that the inorganic alkali solution is NaOH solution and/or KOH solution;
the mass concentration of the inorganic alkali liquor is 30-50%.
9. The preparation method according to claim 1, wherein the temperature of the ring closure reaction is 60-90 ℃, the time is 3-6 h, and the vacuum degree is 81-98 kPa.
10. The preparation method according to claim 1, wherein after the ring-closure reaction, the method further comprises performing post-treatment on the obtained ring-closure reaction solution, wherein the post-treatment comprises:
and (3) washing, neutralizing and dehydrating the closed-loop reaction solution to obtain a pure dodecyl glycidyl ether product.
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| CN117777060A (en) * | 2023-12-26 | 2024-03-29 | 同宇新材料(广东)股份有限公司 | Preparation method of linoleic acid glycidyl ester |
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| US6437196B1 (en) * | 1999-01-25 | 2002-08-20 | Kao Corporation | Process for producing glyceryl ether |
| CN101440074A (en) * | 2008-12-19 | 2009-05-27 | 大连齐化化工有限公司 | Synthesizing method of C12/14 alkyl glycidyl ether |
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| CN117777060A (en) * | 2023-12-26 | 2024-03-29 | 同宇新材料(广东)股份有限公司 | Preparation method of linoleic acid glycidyl ester |
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