CN111072501B - Production method of 2,4, 6-tri (dimethylamine methyl) phenol - Google Patents
Production method of 2,4, 6-tri (dimethylamine methyl) phenol Download PDFInfo
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- CN111072501B CN111072501B CN201911293572.2A CN201911293572A CN111072501B CN 111072501 B CN111072501 B CN 111072501B CN 201911293572 A CN201911293572 A CN 201911293572A CN 111072501 B CN111072501 B CN 111072501B
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- CLZXIZBEKRTINT-UHFFFAOYSA-N n-methylmethanamine;2-methylphenol Chemical compound CNC.CC1=CC=CC=C1O CLZXIZBEKRTINT-UHFFFAOYSA-N 0.000 title abstract description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 86
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000007864 aqueous solution Substances 0.000 claims abstract description 36
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002994 raw material Substances 0.000 claims abstract description 17
- 238000010438 heat treatment Methods 0.000 claims abstract description 15
- 239000000243 solution Substances 0.000 claims abstract description 15
- 238000000926 separation method Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 28
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000000047 product Substances 0.000 abstract description 16
- 239000006227 byproduct Substances 0.000 abstract description 4
- 239000010865 sewage Substances 0.000 abstract description 2
- 239000012071 phase Substances 0.000 description 33
- 238000003860 storage Methods 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 239000002351 wastewater Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 4
- OYEVFSJZQTUDDN-UHFFFAOYSA-N methanol;n-methylmethanamine Chemical compound OC.CNC OYEVFSJZQTUDDN-UHFFFAOYSA-N 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229920006332 epoxy adhesive Polymers 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002309 gasification Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Natural products OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for producing 2,4, 6-tri (dimethylamine methyl) phenol. The method comprises the following steps: (1) adding formaldehyde into dimethylamine, heating to 50-60 ℃, and reacting for 1-3 hours to obtain a solution system; (2) adding phenol into the solution system obtained in the step (1), heating to 80-90 ℃, reacting for 1.5-4 h, standing for layering, and performing oil-water separation, wherein the upper layer is a target product, and the lower layer is a water phase; (3) and (3) feeding the water phase obtained in the step (2) into a double-tower rectification tower, recovering the aqueous solution of dimethylamine from the tower top of the first rectification tower, returning the aqueous solution obtained in the step (1) to be used as a raw material, feeding the aqueous solution discharged from the tower bottom of the first rectification tower into a second rectification tower, feeding the aqueous solution obtained from the tower top of the second rectification tower into a biochemical device, and feeding the material discharged from the tower bottom of the second rectification tower into the step (2) to be used as the raw material. The production method has the advantages of high yield, less by-products and less sewage.
Description
Technical Field
The invention relates to the field of epoxy resin curing catalyst preparation, and particularly relates to a production method of 2,4, 6-tri (dimethylamine methyl) phenol.
Background
2,4, 6-tri (dimethylamine methyl) phenol (DMP-30) is a curing catalyst of thermosetting epoxy resin, can greatly improve the reaction speed of a curing agent and the epoxy resin, and reduce the curing temperature without influencing the physical and chemical properties of the adhesive. Compared with other curing agents, the epoxy adhesive has good catalytic action and complete reaction, and is suitable for low-temperature, high-temperature resistant and low-molecular-weight rubber modified epoxy adhesives and adhesives with certain special purposes and special processes. In particular, in recent years, 2,4, 6-tris (dimethylaminomethyl) phenol has been more widely used with the development of applications of epoxy resins and adhesives.
At present, the classical Mannich method is still adopted for synthesizing 2,4, 6-tri (dimethylaminomethyl) phenol, and the reaction equation is shown as formula I. The synthesis process comprises the steps of firstly adding phenol and dimethylamine aqueous solution, uniformly mixing, then dropwise adding formaldehyde aqueous solution, after dropwise adding, heating to 90-95 ℃ for reaction, after the reaction is finished, carrying out oil-water separation, carrying out organic phase decompression concentration, and distilling to obtain the 2,4, 6-tri (dimethylamine methyl) phenol, wherein the yield is lower than 85%. Research shows that formaldehyde is dripped into mixed liquid of dimethylamine and phenol, and the formaldehyde can participate in side reactions outside the main reaction, as shown in formula II, byproducts such as hydroxybenzyl alcohol and ortho-hydroxybenzyl alcohol are generated, and the byproducts and the dimethylamine which does not completely react are enriched in strong alkaline wastewater, so that the difficulty in treating the wastewater is increased. Meanwhile, due to the occurrence of side reactions and the existence of incompletely reacted mono-substituted and di-substituted intermediates, the yield of the reaction is lower and always lower than 85 percent.
Disclosure of Invention
The invention aims to overcome the defects and provide a production method of 2,4, 6-tri (dimethylamine methyl) phenol, which has high yield, less byproducts and less sewage.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a method for producing 2,4, 6-tris (dimethylaminomethyl) phenol, comprising the steps of:
(1) adding formaldehyde into dimethylamine according to the mass ratio of the dimethylamine to the formaldehyde of 1.1-1.9: 1, heating to 50-60 ℃, and reacting for 1-3 hours to obtain a solution system;
(2) adding phenol into the solution system obtained in the step (1) according to the mass ratio of phenol to formaldehyde of 0.85-1.0: 3, heating to 80-90 ℃, reacting for 1.5-4 h, standing for layering, performing oil-water separation, wherein the upper layer is a target product, and the lower layer is a water phase;
(3) and (3) feeding the water phase obtained in the step (2) into a double-tower rectification tower, recovering the aqueous solution of dimethylamine from the tower top of the first rectification tower, returning the aqueous solution obtained in the step (1) to be used as a raw material, feeding the aqueous solution discharged from the tower bottom of the first rectification tower into a second rectification tower, feeding the aqueous solution obtained from the tower top of the second rectification tower into a biochemical device, and feeding the material discharged from the tower bottom of the second rectification tower into the step (2) to be used as the raw material.
The inventor firstly mixes dimethylamine and formaldehyde, and the dimethylamine methanol is generated by the complete reaction of the dimethylamine and the formaldehyde, as shown in formula III. And then adding phenol, and carrying out substitution reaction on the phenol and dimethylamine methanol as shown in a formula IV, wherein the content of formaldehyde is low, the dimethylamine is excessive, side reaction as shown in a formula II is not easy to occur, and the substitution reaction is easier to directly occur, so that a trisubstituted product, namely 2,4, 6-tri (dimethylamine methyl) phenol is obtained. And (2) separating the product from a water phase, wherein the water phase contains a primary substituted intermediate and a secondary substituted intermediate generated by the reaction shown in the formula V and excessive dimethylamine, the water phase is sent to a secondary distillation procedure, the dimethylamine extracted from the top of the first distillation tower returns to the step (1) to be used as a raw material, and the primary substituted intermediate and the secondary substituted intermediate contained in the material extracted from the bottom of the second distillation tower return to the step (2) to further perform substitution reaction to generate a product, so that the dimethylamine and the intermediate are repeatedly utilized, aminated substances in the wastewater are reduced, and the wastewater treatment cost is reduced.
Preferably, in the step (1), the ratio of the dimethylamine to the formaldehyde is 1.2 to 1.5:1.
Preferably, in the step (1), the reaction time is 1.5-2.5 h, and more preferably, the reaction time is 2 h.
Preferably, in the step (1), the formaldehyde is added dropwise.
Preferably, in the step (2), the mass ratio of phenol to formaldehyde is 0.9 to 1: 3.
Preferably, in the step (2), the reaction time is 2-3 h.
Preferably, in the step (2), the phenol is added dropwise.
Preferably, in the steps (1) and (2), the container used for the reaction is a closed reaction kettle.
Preferably, in the step (3), the temperature of the dimethylamine aqueous solution extracted from the top of the first rectifying tower is 7-15 ℃, and the pressure is 0.1-0.12 MPa. More preferably, the temperature of the produced water at the top of the second rectifying tower is 30-40 ℃, and the pressure is 0.1-0.12 MPa.
The invention has the beneficial effects that:
(1) the production method comprises the steps of mixing formaldehyde and dimethylamine to generate intermediate dimethylamine methanol, adding phenol into the intermediate dimethylamine methanol to perform substitution reaction to obtain a product, wherein excessive dimethylamine is used as alkali in the whole reaction, so that the addition of strong alkali is avoided, meanwhile, the competitive reaction shown in a formula II is avoided, the utilization rate of raw materials is improved, and the reaction yield is improved to 98% from below 85%;
(2) according to the method, dimethylamine and mono-substituted and di-substituted intermediates in the water phase are recycled through double-tower rectification, so that the raw material utilization rate is improved, the product yield is improved, the amount of amine substances in the wastewater and the amount of the wastewater are reduced, and the cost of wastewater treatment is reduced;
(3) in the preferred scheme of the invention, a reaction kettle is used as a reaction vessel, and double-tower rectification is combined, so that volatile substances such as dimethylamine and the like are always in a closed device, and the odor of the dimethylamine is basically eliminated.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
The embodiment comprises the following steps:
(1) 1800kg of dimethylamine (40% strength by weight) were weighed out and added to 6m3The intermittent stirring reaction kettle is controlled at the stirring speed of 40r/min, then 1000kg of formaldehyde (with the concentration of 40 wt%) is weighed, the formaldehyde is uniformly added into the dimethylamine aqueous solution within 1.5 hours by using a metering pump for reaction, after the feeding is finished, the temperature is raised to 60 ℃, and the formaldehyde and the dimethylamine are reacted for 2 hours under the pressure of 0.4Mpa (with certain pressure, the gasification and material loss of the formaldehyde and the dimethylamine caused by the rise of the reactivity can be effectively avoided), so that a solution system is obtained;
(2) weighing 120kg of phenol, uniformly adding the phenol into the solution system obtained in the step (1) within 1.5 hours by using a metering pump, heating to 90 ℃, reacting for 3 hours, standing for layering, performing oil-water separation, allowing the lower layer to be a water phase, allowing the water phase to enter a water phase storage tank, allowing the upper layer to be a target product to enter an oil-water separator for oil-water separation again, allowing the separated organic phase to enter a product storage tank, and allowing the water phase to enter a water phase storage tank;
(3) heating the water phase obtained in the step (2) to a bubble point temperature, allowing the water phase to enter a first rectifying tower, collecting a dimethylamine aqueous solution (with the concentration of 40 wt%) from the tower top, controlling the temperature at 7 ℃ and the pressure at 0.1MPa, returning the aqueous solution to the step (1) as a raw material, allowing the aqueous solution discharged from the tower bottom to enter a second rectifying tower, conveying the aqueous solution collected from the tower top of the second rectifying tower to a biochemical device, allowing the tower top temperature to be 30 ℃ and the pressure to be 0.10MPa, and conveying the material discharged from the tower bottom to the step (2) as the raw material.
Example 2
The embodiment comprises the following steps:
(1) 3600kg of dimethylamine (40 wt% strength) were weighed out and added to 6m3The intermittent stirring reaction kettle is controlled at the stirring speed of 40r/min, 1800kg of formaldehyde (with the concentration of 40 wt%) is weighed, the formaldehyde is uniformly added into the dimethylamine aqueous solution within 2.5 hours by using a metering pump for reaction, the temperature is raised to 60 ℃ after the charging is finished, and the formaldehyde and the dimethylamine are effectively prevented from being gasified and lost due to the rise of the reactivity under the pressure of 0.4MPa (with certain pressure), and the solution system is obtained after the reaction is carried out for 2.5 hours;
(2) weighing 180kg of phenol, uniformly adding the phenol into the solution system obtained in the step (1) within 1.5 hours by using a metering pump, heating to 90 ℃, reacting for 2 hours, standing for layering, performing oil-water separation, allowing the lower layer to be a water phase, allowing the water phase to enter a water phase storage tank, allowing the upper layer to be a target product to enter an oil-water separator for oil-water separation again, allowing the separated organic phase to enter a product storage tank, and allowing the water phase to enter a water phase storage tank;
(3) heating the water phase obtained in the step (2) to a bubble point temperature, allowing the water phase to enter a first rectifying tower, collecting a dimethylamine aqueous solution (with the concentration of 40 wt%) from the tower top, controlling the temperature at 10 ℃ and the pressure at 0.11MPa, returning the aqueous solution to the step (1) as a raw material, allowing the aqueous solution discharged from the tower bottom to enter a second rectifying tower, conveying the aqueous solution collected from the tower top of the second rectifying tower to a biochemical device, allowing the tower top temperature at 35 ℃ and the pressure at 0.11MPa, and conveying the material discharged from the tower bottom to the step (2) as the raw material.
Example 3
The embodiment comprises the following steps:
(1) 3600kg of dimethylamine (40 wt% strength) were weighed out and added to 6m3The intermittent stirring reaction kettle is controlled at the stirring speed of 40r/min, then 1600kg of formaldehyde (with the concentration of 40 wt%) is weighed and uniformly added into the dimethylamine aqueous solution within 2.5 hours by using a metering pump for reaction, after the feeding is finished, the temperature is raised to 50 ℃, and the reaction is carried out for 3 hours under the pressure of 0.4Mpa (with certain pressure, the gasification of the formaldehyde and the dimethylamine and the material loss caused by the rise of the reactivity can be effectively avoided), so as to obtain a solution system;
(2) weighing 160kg of phenol, uniformly adding the phenol into the solution system obtained in the step (1) within 1.5 hours by using a metering pump, heating to 90 ℃, reacting for 3 hours, standing for layering, performing oil-water separation, allowing the lower layer to be a water phase, allowing the water phase to enter a water phase storage tank, allowing the upper layer to be a target product to enter an oil-water separator for oil-water separation again, allowing the separated organic phase to enter a product storage tank, and allowing the water phase to enter a water phase storage tank;
(3) heating the water phase obtained in the step (2) to a bubble point temperature, allowing the water phase to enter a first rectifying tower, collecting a dimethylamine aqueous solution (with the concentration of 40 wt%) from the tower top, controlling the temperature at 15 ℃ and the pressure at 0.1MPa, returning the aqueous solution to the step (1) as a raw material, allowing the aqueous solution discharged from the tower bottom to enter a second rectifying tower, conveying the aqueous solution collected from the tower top of the second rectifying tower to a biochemical device, allowing the tower top temperature to be 40 ℃ and the pressure to be 0.10MPa, and conveying the material discharged from the tower bottom to the step (2) as the raw material.
By combining the above schemes, various relevant process parameters and indexes can be obtained:
| case column | The product yield is% | Recovering dimethylamine aqueous solution% | Waste water COD (mg/L) |
| First scheme column | 98.1 | 42 | 453 |
| Second case column | 98.3 | 41 | 430 |
| Third scheme | 98.1 | 40 | 450 |
Comparative example 1
The method is based on the literature: journal of chemical engineering, 3 rd period 21-24) of 1991) and specifically comprises the following steps:
(1) 1714kg of dimethylamine (33% strength by weight) were weighed into 6m3The intermittent stirring reaction kettle is controlled at the stirring speed of 40r/min and the temperature of 4 ℃, then 730kg of formaldehyde (with the concentration of 36 wt%) is weighed, the formaldehyde is uniformly added into the dimethylamine aqueous solution within 2.0 hours by using a metering pump for reaction, the temperature is raised to 10 ℃ after the addition of the formaldehyde is finished, and the reaction is carried out for 0.5 hour to obtain a solution system;
(2) weighing 236kg of phenol, uniformly adding the phenol into the solution system obtained in the step (1) within 1.0 hour by using a metering pump, heating to 90 ℃, reacting for 1.5 hours, standing for layering, performing oil-water separation, allowing the lower layer to be a water phase to enter a filter, allowing filter residues to be white solids, allowing filtrate to enter a water phase storage tank, allowing the upper layer to be a target product to enter an oil-water separator for oil-water separation again, allowing the separated organic phase to enter a product storage tank, and allowing the water phase to enter a water phase storage tank;
(3) heating the water phase obtained in the step (2) to a bubble point temperature, allowing the water phase to enter a first rectifying tower, collecting a dimethylamine aqueous solution (with the concentration of 40 wt%) from the tower top, controlling the temperature at 15 ℃ and the pressure at 0.1MPa, returning the aqueous solution to the step (1) as a raw material, allowing the aqueous solution discharged from the tower bottom to enter a second rectifying tower, conveying the aqueous solution collected from the tower top of the second rectifying tower to a biochemical device, allowing the tower top temperature to be 40 ℃ and the pressure to be 0.10MPa, and conveying the material discharged from the tower bottom to the step (2) as the raw material.
After the synthesis by the process, the yield is 84%, and the yield is influenced mainly because of white solid generated by side reaction.
Claims (4)
1. A method for producing 2,4, 6-tris (dimethylaminomethyl) phenol, comprising the steps of:
(1) adding formaldehyde into dimethylamine according to the mass ratio of the dimethylamine to the formaldehyde of 1.2-1.5: 1, heating to 50-60 ℃, and reacting for 2-2.5 hours under the pressure of 0.4Mpa to obtain a solution system; the formaldehyde is added dropwise;
(2) according to the mass ratio of phenol to 40 wt% of formaldehyde of 120: 1000 or 180: 1800 adding phenol into the solution system obtained in the step (1), heating to 90 ℃, reacting for 2-3 h, standing for layering, and performing oil-water separation, wherein the upper layer is a target product, and the lower layer is a water phase; the phenol is added dropwise;
(3) feeding the water phase obtained in the step (2) into a double-tower rectification tower for rectification, recovering a dimethylamine aqueous solution from the tower top of a first rectification tower, returning the dimethylamine aqueous solution to the step (1) as a raw material, feeding the aqueous solution discharged from the tower bottom of the first rectification tower into a second rectification tower, feeding the aqueous solution discharged from the tower top of the second rectification tower into a biochemical device, and feeding the material discharged from the tower bottom of the second rectification tower into the step (2) as the raw material;
in the steps (1) and (2), the container adopted by the reaction is a closed reaction kettle.
2. A process for producing 2,4, 6-tris (dimethylaminomethyl) phenol according to claim 1, characterized in that in step (1), the reaction time is 2 hours.
3. The process for producing 2,4, 6-tris (dimethylaminomethyl) phenol according to claim 1, wherein in the step (3), the temperature of the aqueous dimethylamine solution taken out from the top of the first rectifying column is 7 to 15 ℃ and the pressure is 0.1 to 0.12 MPa.
4. The method for producing 2,4, 6-tris (dimethylaminomethyl) phenol according to claim 1, wherein in the step (3), the temperature of the produced water at the top of the second rectifying tower is 30-40 ℃, and the pressure is 0.1-0.12 MPa.
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| CN115974704B (en) * | 2022-12-28 | 2023-09-15 | 常州山峰化工有限公司 | Novel process for preparing epoxy resin curing accelerator DMP-30 |
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| DE2540071A1 (en) * | 1975-09-09 | 1977-03-17 | Siemens Ag | PROCESS FOR MANUFACTURING RIGID POLYURETHANE FOAM |
| US5098505A (en) * | 1986-06-23 | 1992-03-24 | Ashland Oil, Inc. | Epoxy resin, thermoplastic polymer and hardener adhesive |
| CN103508908B (en) * | 2013-10-24 | 2015-03-11 | 浙江鼎龙科技有限公司 | Preparation method for 4-amino-3-methylphenol |
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Denomination of invention: A production method of 2,4,6-tris (dimethylaminomethyl) phenol Granted publication date: 20210611 Pledgee: Hunan Yueyang Rural Commercial Bank Co.,Ltd. Yunxi Sub branch Pledgor: YUEYANG ZHONGZHAN TECHNOLOGY CO.,LTD. Registration number: Y2024980020636 |