CN115925653B - Synthesis method of epoxy reactive diluent o-cresol glycidyl ether - Google Patents
Synthesis method of epoxy reactive diluent o-cresol glycidyl ether Download PDFInfo
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- CN115925653B CN115925653B CN202211184073.1A CN202211184073A CN115925653B CN 115925653 B CN115925653 B CN 115925653B CN 202211184073 A CN202211184073 A CN 202211184073A CN 115925653 B CN115925653 B CN 115925653B
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- 239000004593 Epoxy Substances 0.000 title claims abstract description 68
- 239000003085 diluting agent Substances 0.000 title claims abstract description 61
- KFUSXMDYOPXKKT-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OCC1OC1 KFUSXMDYOPXKKT-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000001308 synthesis method Methods 0.000 title description 7
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000007788 liquid Substances 0.000 claims abstract description 34
- 239000003513 alkali Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 22
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 19
- 230000006837 decompression Effects 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 230000018044 dehydration Effects 0.000 claims abstract description 6
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 6
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 84
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 230000007935 neutral effect Effects 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 2
- 238000007142 ring opening reaction Methods 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 abstract description 11
- 229920000647 polyepoxide Polymers 0.000 abstract description 11
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 7
- 238000005260 corrosion Methods 0.000 abstract description 3
- 230000007797 corrosion Effects 0.000 abstract description 3
- 125000003700 epoxy group Chemical group 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 abstract description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 24
- 238000000926 separation method Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007888 film coating Substances 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000005028 tinplate Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Epoxy Compounds (AREA)
Abstract
The invention discloses a method for synthesizing epoxy reactive diluent o-cresol glycidyl ether, which comprises the steps of firstly generating chlorohydrin ether by o-cresol and epoxy chloropropane under the action of liquid alkali, then generating epoxy reactive diluent o-cresol glycidyl ether by ring closure reaction under the actions of decompression alkali addition and dehydration reflux, removing redundant epoxy chloropropane in a decompression rotary evaporator, and finally obtaining the epoxy reactive diluent o-cresol glycidyl ether. The prepared epoxy reactive diluent o-cresol glycidyl ether can be used as an epoxy reactive diluent, belongs to a monofunctional reactive diluent, contains benzene rings, ether bonds and epoxy groups, has certain rigidity, heat resistance and corrosion resistance, and is used as a diluent of epoxy resin to reduce the viscosity of an epoxy system and improve the mechanical properties of an epoxy cured product.
Description
Technical Field
The invention relates to a method for synthesizing an epoxy reactive diluent o-cresol glycidyl ether, belonging to the technical field of high polymer materials.
Background
The epoxy reactive diluent o-cresol glycidyl ether is an important organic chemical intermediate, is widely applied to the fields of paint industry and synthetic chemical industry, can be used as an epoxy reactive diluent, belongs to a monofunctional reactive diluent, contains benzene rings, ether bonds and epoxy groups, has certain rigidity, heat resistance and corrosion resistance, and is used as a diluent of epoxy resin to reduce the viscosity of an epoxy system and improve the mechanical properties of epoxy condensate. At present, a related synthesis method of the o-cresol glycidyl ether serving as an epoxy reactive diluent is not searched temporarily, so that the synthesis method of the o-cresol glycidyl ether serving as the epoxy reactive diluent is needed to be provided.
Disclosure of Invention
The invention aims to: at present, no relevant synthesis method of the epoxy reactive diluent o-cresol glycidyl ether is searched temporarily, so the invention provides the synthesis method of the epoxy reactive diluent o-cresol glycidyl ether, which has the advantages of high raw material conversion rate, mild condition, high yield, simple and convenient operation and suitability for industrial production.
The technical scheme adopted by the invention for realizing the purposes is as follows:
A method for synthesizing an epoxy reactive diluent o-cresol glycidyl ether comprises the following steps:
(1) Ring opening reaction: adding o-cresol and epichlorohydrin into a reactor, uniformly stirring, adding liquid alkali, maintaining at 50-70 ℃ and keeping for a period of time;
(2) Ring closure reaction: stirring is started, alkali is added in a decompression dehydration reflux state, and after the completion of the alkali adding, the stirring is maintained for a period of time;
(3) De-epichlorohydrin: after the reaction is finished, adding water to dissolve the generated salt, separating out an organic phase, washing with water to be neutral, and removing redundant epichlorohydrin to obtain the epoxy reactive diluent o-cresol glycidyl ether.
In the method for synthesizing the epoxy reactive diluent o-cresol glycidyl ether, in the step 1, the molar ratio of the epoxy chloropropane to the o-cresol is 2:1-4:1; the liquid alkali is sodium hydroxide solution with the mass concentration of 50%, and the molar ratio of sodium hydroxide to o-cresol is 0.1:1-0.16:1.
In the method for synthesizing the o-cresol glycidyl ether serving as the epoxy reactive diluent, in the step 1, the molar ratio of epoxy chloropropane to o-cresol is 2:1, 3:1 and 4:1; the molar ratio of sodium hydroxide to o-cresol is 0.1:1, 0.12:1, 0.14:1, 0.16:1.
As a preferable scheme, in the method for synthesizing the epoxy reactive diluent o-cresol glycidyl ether, in the step 1, the molar ratio of epoxy chloropropane to o-cresol is 3:1, and the molar ratio of sodium hydroxide to o-cresol is 0.14:1.
As a preferred embodiment, the above-mentioned method for synthesizing o-cresol glycidyl ether as an epoxy reactive diluent is characterized in that the liquid alkali is added and maintained at 60 ℃ for 4 hours.
As a preferable scheme, in the method for synthesizing the o-cresol glycidyl ether serving as the epoxy reactive diluent, in the step 2, the liquid alkali is sodium hydroxide solution with the mass concentration of 50%; the molar ratio of the sodium hydroxide to the o-cresol is 0.8:1-1:1.
As a preferable scheme, in the method for synthesizing the o-cresol glycidyl ether serving as the epoxy reactive diluent, in the step 2, the molar ratio of sodium hydroxide to o-cresol is 0.8:1, 0.9:1 and 1:1. More preferably, the molar ratio of sodium hydroxide to o-cresol is 0.8:1, 0.9:1, 1:1, particularly preferably 0.9:1.
As a preferable scheme, in the method for synthesizing the o-cresol glycidyl ether serving as the epoxy reactive diluent, in the step 2, alkali is added for 3 hours under the conditions of 21KPa and 63 ℃ reduced pressure dehydration reflux, and after the completion, the reaction is maintained for 0.5 hour. Condensing and refluxing epichlorohydrin and separating water under the conditions of 21KPa and 63 ℃ in a decompression dehydration reflux state, and timely separating water to minimize the hydrolysis of epichlorohydrin.
The water added in the step 3 of the step 2 is pure water, laboratory liquid separation is carried out by adopting a separating funnel, redundant epichlorohydrin in the resin is removed by adopting vacuumizing and a rotary evaporator, and the separated epichlorohydrin is recycled.
The epoxy reactive diluent o-cresol glycidyl ether prepared by the method can be applied to preparation of epoxy reactive diluents.
The beneficial effects are that: the invention obtains the optimal raw material proportion through a large number of experiments and optimizes the optimal synthesis process through a large number of experiments. The preparation process is reasonable in design, chlorohydrin ether is generated by o-cresol and epoxy chloropropane under the action of liquid alkali, a small amount of o-cresol glycidyl ether serving as an epoxy reactive diluent possibly exists, then the o-cresol glycidyl ether serving as the epoxy reactive diluent is generated by ring closure reaction under the actions of decompression alkali addition and dehydration reflux, the redundant epoxy chloropropane is removed in a decompression rotary evaporator, and finally the o-cresol glycidyl ether serving as the epoxy reactive diluent is obtained, and the o-cresol glycidyl ether serving as the epoxy reactive diluent contains benzene rings, ether bonds and epoxy groups, has certain rigidity, heat resistance and corrosion resistance, and is used as the diluent of epoxy resin to reduce the viscosity of an epoxy system and improve the mechanical property of epoxy condensate. The yield of the synthesis method can reach 98.3 percent.
Detailed Description
Example 1
A method for synthesizing o-cresol glycidyl ether as an epoxy reactive diluent comprises the following steps:
540g of o-cresol, 925g of epichlorohydrin, 48g of liquid alkali (sodium hydroxide solution with the mass concentration of 50%) and the like are added into a 3000ml four-neck flask, and the mixture is kept at 50 ℃ for 4 hours; the temperature is raised to 63 ℃, 360g of caustic soda is added dropwise under the vacuum degree of 21Kpa, 3 hours are added, the reaction is kept for 0.5 hour, water is added to dissolve salt after the reaction is finished, then the salt is transferred to a separating funnel to separate filtrate, water washing is carried out to neutral liquid separation, and after liquid separation, the redundant epichlorohydrin is removed to obtain 738g of o-cresol glycidyl ether serving as an epoxy reactive diluent, the yield is 90%, and the detected epoxy value is 0.49eq/100g.
Example 2
A method for synthesizing o-cresol glycidyl ether as an epoxy reactive diluent comprises the following steps:
540g of o-cresol, 1387.5g of epichlorohydrin and 56g of liquid alkali (sodium hydroxide solution with the mass concentration of 50%) are added into a 3000ml four-neck flask, and the mixture is kept at 60 ℃ for 4 hours; the temperature is raised to 63 ℃, 360g of caustic soda is added dropwise under the vacuum degree of 21Kpa, 3 hours are added, the reaction is kept for 0.5 hour, water is added to dissolve salt after the reaction is finished, then the salt is transferred to a separating funnel to separate filtrate, water washing is carried out to neutral liquid separation, and after the liquid separation, the redundant epichlorohydrin is removed to obtain 806g of o-cresol glycidyl ether serving as an epoxy reactive diluent, the yield is 98.3%, and the detected epoxy value is 0.589eq/100g.
Example 3
A method for synthesizing o-cresol glycidyl ether as an epoxy reactive diluent comprises the following steps:
540g of o-cresol, 1850g of epichlorohydrin and 64g of liquid alkali (sodium hydroxide solution with the mass concentration of 50%) are added into a 3000ml four-neck flask, and the mixture is kept at 70 ℃ for 4 hours; the temperature is raised to 63 ℃, 400g of caustic soda is added dropwise under the vacuum degree of 21Kpa, 3 hours are added, the reaction is kept for 0.5 hour, water is added to dissolve salt after the reaction is finished, then the salt is transferred to a separating funnel to separate filtrate, water washing is carried out to neutral liquid separation, and after liquid separation, the redundant epichlorohydrin is removed to obtain 798g of o-cresol glycidyl ether serving as an epoxy reactive diluent, the yield is 97.3%, and the detected epoxy value is 0.588eq/100g.
Example 4
A method for synthesizing o-cresol glycidyl ether as an epoxy reactive diluent comprises the following steps:
540g of o-cresol, 925g of epichlorohydrin, and 56g of liquid alkali (sodium hydroxide solution with the mass concentration of 50%) are added into a 3000ml four-neck flask, and the mixture is kept at 50 ℃ for 4 hours; the temperature is raised to 63 ℃, 320g of caustic soda is added dropwise under the vacuum degree of 21Kpa, the reaction time is 3 hours, the reaction time is 0.5 hour, water is added to dissolve salt after the reaction is finished, the salt is transferred to a separating funnel to separate filtrate, water washing is carried out to neutral liquid separation, redundant epichlorohydrin is removed after liquid separation, 764g of o-cresol glycidyl ether serving as an epoxy reactive diluent is obtained, the yield is 93.2%, and the detected epoxy value is 0.48eq/100g.
Example 5
A method for synthesizing o-cresol glycidyl ether as an epoxy reactive diluent comprises the following steps:
540g of o-cresol, 1387.5g of epichlorohydrin and 64g of liquid alkali (sodium hydroxide solution with the mass concentration of 50%) are added into a 3000ml four-neck flask, and the mixture is kept at 50 ℃ for 4 hours; the temperature is raised to 63 ℃, 400g of caustic soda is added dropwise under the vacuum degree of 21Kpa, the reaction time is 3 hours, the reaction time is 0.5 hour, water is added to dissolve salt after the reaction is finished, the salt is transferred to a separating funnel to separate filtrate, water washing is carried out to neutral liquid separation, and after the liquid separation, the redundant epichlorohydrin is removed to obtain 803g of o-cresol glycidyl ether serving as an epoxy reactive diluent, the yield is 97.9%, and the detected epoxy value is 0.57eq/100g.
Example 6
A method for synthesizing o-cresol glycidyl ether as an epoxy reactive diluent comprises the following steps:
540g of o-cresol, 1387.5g of epichlorohydrin and 56g of liquid alkali (sodium hydroxide solution with the mass concentration of 50%) are added into a 3000ml four-neck flask, and the mixture is kept at 70 ℃ for 4 hours; the temperature is raised to 63 ℃, 360g of caustic soda is added dropwise under the vacuum degree of 21Kpa, 3 hours are added, the reaction is kept for 0.5 hour, water is added to dissolve salt after the reaction is finished, then the salt is transferred to a separating funnel to separate filtrate, water washing is carried out to neutral liquid separation, and after liquid separation, the redundant epichlorohydrin is removed to obtain 800g of o-cresol glycidyl ether serving as an epoxy reactive diluent, the yield is 97.5%, and the detected epoxy value is 0.568eq/100g.
Example 7
A method for synthesizing o-cresol glycidyl ether as an epoxy reactive diluent comprises the following steps:
540g of o-cresol, 1387.5g of epichlorohydrin and 56g of liquid alkali (sodium hydroxide solution with the mass concentration of 50%) are added into a 3000ml four-neck flask, and the mixture is kept at 60 ℃ for 4 hours; the temperature is raised to 63 ℃, 400g of caustic soda is added dropwise under the vacuum degree of 21Kpa, the reaction time is 3 hours, the reaction time is 0.5 hour, water is added to dissolve salt after the reaction is finished, the salt is transferred to a separating funnel to separate filtrate, water washing is carried out to neutral liquid separation, and redundant epichlorohydrin is removed after liquid separation to obtain 802g of o-cresol glycidyl ether serving as an epoxy reactive diluent, the yield is 97.8%, and the detected epoxy value is 0.57eq/100g.
Example 8
A method for synthesizing o-cresol glycidyl ether as an epoxy reactive diluent comprises the following steps:
540g of o-cresol, 1387.5g of epichlorohydrin and 48g of liquid alkali (sodium hydroxide solution with the mass concentration of 50%) are added into a 3000ml four-neck flask, and the mixture is kept at 60 ℃ for 4 hours; the temperature is raised to 63 ℃, 360g of caustic soda is added dropwise under the vacuum degree of 21Kpa, 3 hours are added, the reaction is kept for 0.5 hour, water is added to dissolve salt after the reaction is finished, then the salt is transferred to a separating funnel to separate filtrate, water washing is carried out to neutral liquid separation, and after liquid separation, the redundant epichlorohydrin is removed to obtain 796g of o-cresol glycidyl ether serving as an epoxy reactive diluent, the yield is 97%, and the detected epoxy value is 0.502eq/100g.
Example 9
Epoxy reactive Diluent o-cresol glycidyl Ether and conventional Diluent AGE (carbon dodecatetradecyl glycidyl Ether) dilution base epoxy resin (E-51) comparative experiment
Sample 1: the epoxy reactive diluent o-cresol glycidyl ether prepared in example 2 and the basic epoxy resin (E-51) are prepared according to a mass ratio of 1:4, and after being matched with a polyamide curing agent, the epoxy reactive diluent o-cresol glycidyl ether and the basic epoxy resin are subjected to film formation (specification of 50 um) on a tinplate by using a four-sided film coating preparation device, are subjected to normal temperature curing for 20 hours, and the test film thickness is about 50um.
Sample 2: AGE and basic epoxy resin (E-51) are prepared according to a mass ratio of 1:4, and are matched with a polyamide curing agent, and then film formation (specification 50 um) is carried out on a tinplate by using a four-side film coating preparation device, normal temperature curing is carried out for 20 hours, and the thickness of the film is tested to be about 50um.
The test performance for samples 1 and 2 is shown in table 1.
TABLE 1
| Sample 1 | Sample 2 | |
| The diluent accounts for the mass percent (%) | 20 | 20 |
| Viscosity (mpa.s/25 ℃ C.) | 850 | 1000 |
| Paint film hardness of epoxy cured product | 2-3H | 1-2H |
| Butanone rub resistance times of paint film of epoxy cured product | 76 Times | 65 Times |
The hardness of the paint film of the epoxy cured product was tested by a manual method, and the paint film was prepared by using Chinese pencils, wherein the paint film has different hardness from 9H to 6B, and the paint film has the hardness of 9H and the hardness of 6B.
The viscosity of the epoxy reactive diluent o-cresol glycidyl ether synthesized by the invention and the basic epoxy resin diluted by the conventional diluent is lower than that of the basic epoxy resin diluted by the conventional diluent when the mass ratio of the o-cresol glycidyl ether to the basic epoxy resin is 1:4, and the hardness and solvent resistance of a paint film of a cured product are better than those of the epoxy resin diluted by the conventional diluent.
The foregoing is merely a preferred embodiment of the present invention and it should be noted that modifications and adaptations to those skilled in the art may be made without departing from the principles of the present invention, which are intended to be comprehended within the scope of the present invention.
Claims (1)
1. The method for synthesizing the o-cresol glycidyl ether serving as the epoxy reactive diluent is characterized by comprising the following steps of:
(1) Ring opening reaction: adding o-cresol and epichlorohydrin into a reactor, uniformly stirring, adding liquid alkali, maintaining at 60 ℃ and keeping for 4 hours;
(2) Ring closure reaction: stirring is started, alkali is added for 3 hours under the conditions of 21KPa and 63 ℃ decompression dehydration reflux, and after the completion, the solution is kept for 0.5 hour;
(3) De-epichlorohydrin: adding water to dissolve the generated salt after the reaction is finished, separating out an organic phase, washing with water to be neutral, and removing redundant epichlorohydrin to obtain an epoxy reactive diluent o-cresol glycidyl ether;
in the step (1), the molar ratio of the epichlorohydrin to the o-cresol is 3:1; the liquid alkali is sodium hydroxide solution with the mass concentration of 50%, and the molar ratio of sodium hydroxide to o-cresol is 0.14:1;
In the step (2), the liquid alkali is sodium hydroxide solution with the mass concentration of 50%, and the molar ratio of sodium hydroxide to o-cresol is 0.9:1.
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