CN113372301A - Preparation process of alkyl glycidyl ether serving as active epoxy resin diluent - Google Patents
Preparation process of alkyl glycidyl ether serving as active epoxy resin diluent Download PDFInfo
- Publication number
- CN113372301A CN113372301A CN202110540486.8A CN202110540486A CN113372301A CN 113372301 A CN113372301 A CN 113372301A CN 202110540486 A CN202110540486 A CN 202110540486A CN 113372301 A CN113372301 A CN 113372301A
- Authority
- CN
- China
- Prior art keywords
- fatty alcohol
- epoxy resin
- glycidyl ether
- resin diluent
- alkyl glycidyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003085 diluting agent Substances 0.000 title claims abstract description 29
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 27
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 27
- -1 alkyl glycidyl ether Chemical compound 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000047 product Substances 0.000 claims abstract description 17
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 claims abstract description 12
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 11
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012043 crude product Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 238000006266 etherification reaction Methods 0.000 claims abstract description 6
- 230000018044 dehydration Effects 0.000 claims abstract description 4
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 4
- 238000011033 desalting Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 230000007935 neutral effect Effects 0.000 claims abstract description 4
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 238000007670 refining Methods 0.000 claims abstract description 4
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- 238000011084 recovery Methods 0.000 claims description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical group FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 abstract description 5
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
Abstract
The application discloses a preparation process of an alkyl glycidyl ether serving as an active epoxy resin diluent, which sequentially comprises the following steps: s1, firstly, pretreating excessive fatty alcohol and epoxy chloropropane, then adding a ring-opening catalyst and epoxy chloropropane, and carrying out etherification ring-opening reaction at 50-70 ℃ to obtain an intermediate chlorohydrin ether and excessive fatty alcohol mixture; s2, rectifying and recovering the mixture obtained in the step S1 to obtain fatty alcohol and an intermediate chlorohydrin ether; s3, adding an alkali solution into the intermediate chlorohydrin ether obtained in the step S2, performing ring-closure reaction for 3-6 hours at 40-60 ℃, neutralizing excessive alkali to be neutral, and washing for desalting to obtain an epoxy resin diluent alkyl glycidyl ether crude product; s4, heating the crude product obtained in the step S3, introducing nitrogen, carrying out vacuum stripping, refining and dehydration under the vacuum degree of-0.09 MPa, and removing water and small molecular substances of the front cut fraction to obtain the product. The invention reduces the by-products and improves the yield of the product and the yield of the superior product.
Description
Technical Field
The invention belongs to the technical field of preparation of epoxy resin reactive diluents, and particularly relates to a preparation process of an alkyl glycidyl ether reactive epoxy resin diluent.
Background
The epoxy resin diluent is used by being mixed with the base resin, so that the viscosity of a curing system can be reduced, the fluidity is increased, the service life is prolonged, and large-area construction is facilitated; improves the operability and does not influence the basic performance of a cured product. The method is convenient for casting, pouring, bonding, sealing, dipping and other applications.
Disclosure of Invention
The invention aims to provide a preparation process of an alkyl glycidyl ether serving as an active epoxy resin diluent.
In order to achieve the above object, the present invention provides the following technical solutions.
The embodiment of the application discloses a preparation process of an alkyl glycidyl ether serving as an active epoxy resin diluent, which sequentially comprises the following steps:
s1, firstly, pretreating excessive fatty alcohol and epoxy chloropropane, then adding a ring-opening catalyst and epoxy chloropropane, and carrying out etherification ring-opening reaction at 50-70 ℃ to obtain an intermediate chlorohydrin ether and excessive fatty alcohol mixture;
s2, rectifying and recovering the mixture obtained in the step S1 to obtain fatty alcohol and an intermediate chlorohydrin ether;
s3, adding an alkali solution into the intermediate chlorohydrin ether obtained in the step S2, performing ring-closure reaction for 3-6 hours at 40-60 ℃, neutralizing excessive alkali to be neutral, and washing for desalting to obtain an epoxy resin diluent alkyl glycidyl ether crude product;
s4, heating the crude product obtained in the step S3, introducing nitrogen, carrying out vacuum stripping, refining and dehydration under the vacuum degree of-0.09 MPa, and removing water and small molecular substances of the front cut fraction to obtain the product.
Preferably, in the above process for preparing an alkyl glycidyl ether as a reactive epoxy resin diluent, in step S1, the fatty alcohol is a C3-C14 alkyl alcohol.
Preferably, in the above process for preparing an alkyl glycidyl ether as a reactive epoxy resin diluent, in step S1, the catalyst is boron trifluoride diethyl etherate.
Preferably, in the above preparation process of the reactive epoxy resin diluent alkyl glycidyl ether, in step S1, the amount of the catalyst added is 0.5-1.5% by weight of the fatty alcohol.
Preferably, in the above process for preparing an alkyl glycidyl ether as an active epoxy resin diluent, in step S1, the molar ratio of the fatty alcohol to the total amount of the epichlorohydrin is 1.6 to 2.
Preferably, in the preparation process of the alkyl glycidyl ether as the reactive epoxy resin diluent, in step S2, the rectification recovery refers to vacuum stripping recovery at a vacuum degree of-0.09 MPa and a temperature of 50 to 160 ℃.
Preferably, in the preparation process of the alkyl glycidyl ether as the reactive epoxy resin diluent, in step S3, the molar ratio of the addition amount of the alkali solution to the total amount of the epichlorohydrin is 1.05 to 1.2.
Preferably, in the above process for preparing alkyl glycidyl ether as reactive epoxy resin diluent, the total chlorine content of the product obtained in step S4 is less than 2000ppm, the content of hydrolyzable chlorine is less than 500ppm, and the product is rectified to obtain high-purity reactive epoxy resin diluent with the total chlorine content of less than 700ppm and the content of hydrolyzable chlorine of less than 100 ppm.
The invention has the advantages that the novel process of fatty alcohol excess and recovery is adopted in the etherification ring-opening reaction, the by-products in the ring-opening reaction process of the fatty alcohol and the epichlorohydrin are reduced, the product yield and the superior product yield are improved, and meanwhile, the fatty alcohol recovered by rectification has high purity and less impurities, can be recycled, reduces the preparation cost, reduces the discharge of the generated by-products, and is more economic and environment-friendly.
The invention has stable and reliable process, stable product, low hydrolytic chlorine and light chroma, and the total chlorine content of the prepared epoxy diluent is lower than 2000ppm and the hydrolytic chlorine content is lower than 500 ppm.
Detailed Description
Technical solutions in the embodiments of the present invention will be described in detail below, and it is apparent that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
The new preparation process of alkyl glycidyl ether as active epoxy resin diluent comprises the following steps:
(1) taking excessive fatty alcohol and epoxy chloropropane as raw materials, firstly pretreating the fatty alcohol, then adding a ring-opening catalyst and epoxy chloropropane, and carrying out etherification ring-opening reaction at 50-70 ℃ to obtain a mixture of intermediate chlorohydrin ether and the excessive fatty alcohol, wherein the catalyst is boron trifluoride diethyl etherate, the addition amount of the catalyst is 0.5-1.5% of the weight of the fatty alcohol, and the molar ratio of the fatty alcohol to the epoxy chloropropane is 1.6-2: 1;
(2) rectifying the mixture obtained in the step (1) at-0.09 MPa and 50-160 ℃ to recover excessive fatty alcohol, and respectively obtaining recovered fatty alcohol and intermediate chlorohydrin ether, wherein the recovered fatty alcohol can be used as a raw material of the next batch;
(3) continuously adding an alkali solution into the reaction system of the intermediate chlorohydrin ether obtained in the step (2), wherein the molar ratio of the addition amount to the epoxy chloropropane is 1.05-1.2: 1, carrying out ring-closing reaction for 3-6 h at 40-60 ℃, neutralizing excessive alkali to be neutral, and then washing and desalting the alkali to obtain an epoxy resin diluent alkyl glycidyl ether crude product;
(4) and (3) introducing nitrogen into the crude product of the epoxy resin diluent alkyl glycidyl ether obtained in the step (3) in the process of heating, carrying out vacuum stripping refining dehydration under the vacuum degree of-0.09 MPa, and removing water and small molecular substances of front fraction to obtain the alkyl glycidyl ether product, wherein the total chlorine content is less than 2000ppm, and the hydrolysable chlorine content is less than 500 ppm. The high-purity reactive epoxy resin diluent with the total chlorine content of less than 700ppm and the hydrolysable chlorine content of less than 100ppm can be obtained by rectification.
Further, a new process of fatty alcohol excess and recovery is adopted in the step (2), the fatty alcohol is C3-C14 alkyl alcohol (such as propanol, butanol, octanol and the like), and the excess fatty alcohol is rectified and recovered by vacuum stripping at-0.09 MPa and 50-160 ℃.
The invention has the advantages that the novel process of fatty alcohol excess and recovery is adopted in the etherification ring-opening reaction, the by-products in the ring-opening reaction process of the fatty alcohol and the epichlorohydrin are reduced, the product yield and the superior product yield are improved, and meanwhile, the fatty alcohol recovered by rectification has high purity and less impurities, can be recycled, reduces the preparation cost, reduces the discharge of the generated by-products, and is more economic and environment-friendly.
The invention has stable and reliable process, stable product, low hydrolytic chlorine and light chroma, and the total chlorine content of the prepared epoxy diluent is lower than 2000ppm and the hydrolytic chlorine content is lower than 500 ppm.
The present embodiments are to be considered as illustrative and not restrictive, and the scope of the patent is to be determined by the appended claims.
Claims (8)
1. A preparation process of an alkyl glycidyl ether serving as an active epoxy resin diluent is characterized by sequentially comprising the following steps of:
s1, firstly, pretreating excessive fatty alcohol and epoxy chloropropane, then adding a ring-opening catalyst and epoxy chloropropane, and carrying out etherification ring-opening reaction at 50-70 ℃ to obtain an intermediate chlorohydrin ether and excessive fatty alcohol mixture;
s2, rectifying and recovering the mixture obtained in the step S1 to obtain fatty alcohol and an intermediate chlorohydrin ether;
s3, adding an alkali solution into the intermediate chlorohydrin ether obtained in the step S2, performing ring-closure reaction for 3-6 hours at 40-60 ℃, neutralizing excessive alkali to be neutral, and washing for desalting to obtain an epoxy resin diluent alkyl glycidyl ether crude product;
s4, heating the crude product obtained in the step S3, introducing nitrogen, carrying out vacuum stripping, refining and dehydration under the vacuum degree of-0.09 MPa, and removing water and small molecular substances of the front cut fraction to obtain the product.
2. The process of claim 1, wherein the fatty alcohol is a C3-C14 alkyl alcohol in step S1.
3. The process of claim 1, wherein in step S1, the catalyst is boron trifluoride etherate.
4. The process according to claim 1, wherein the amount of the catalyst added in step S1 is 0.5-1.5% by weight of the fatty alcohol.
5. The process of claim 1, wherein in step S1, the molar ratio of the fatty alcohol to the total amount of epichlorohydrin is 1.6-2.
6. The process for preparing alkyl glycidyl ether as an active epoxy resin diluent in claim 1, wherein in the step S2, the rectification recovery is vacuum stripping recovery at a vacuum degree of-0.09 MPa and a temperature of 50-160 ℃.
7. The process for preparing alkyl glycidyl ether as a reactive epoxy resin diluent in claim 1, wherein in step S3, the molar ratio of the addition amount of the alkali solution to the total amount of the epichlorohydrin is 1.05-1.2.
8. The process of claim 1, wherein the product obtained in step S4 has a total chlorine content of <2000ppm, a hydrolysable chlorine content of <500ppm, and the product is rectified to obtain a high purity reactive epoxy resin diluent having a total chlorine content of <700ppm and a hydrolysable chlorine content of <100 ppm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110540486.8A CN113372301A (en) | 2021-05-18 | 2021-05-18 | Preparation process of alkyl glycidyl ether serving as active epoxy resin diluent |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110540486.8A CN113372301A (en) | 2021-05-18 | 2021-05-18 | Preparation process of alkyl glycidyl ether serving as active epoxy resin diluent |
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| CN113372301A true CN113372301A (en) | 2021-09-10 |
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| CN202110540486.8A Pending CN113372301A (en) | 2021-05-18 | 2021-05-18 | Preparation process of alkyl glycidyl ether serving as active epoxy resin diluent |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115028606A (en) * | 2022-05-26 | 2022-09-09 | 江苏扬农锦湖化工有限公司 | Preparation method of benzyl glycidyl ether |
| CN115960057A (en) * | 2022-12-29 | 2023-04-14 | 苏州元素集化学工业有限公司 | Method for preparing alkyl glycidyl ether by novel catalyst |
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| 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 |
| CN102766114A (en) * | 2012-06-25 | 2012-11-07 | 上海树脂厂有限公司 | Production method of epoxy active diluent |
| CN103191761A (en) * | 2013-03-13 | 2013-07-10 | 南京林业大学 | Catalyst, preparation method thereof and method for preparing aliphatic glycidyl ether by using catalyst |
| CN103333137A (en) * | 2013-06-25 | 2013-10-02 | 湖北恒鑫化工有限公司 | Method for synthesizing allyl glycidyl ether |
| CN106220828A (en) * | 2016-07-23 | 2016-12-14 | 辽阳鑫宇化工有限公司 | A kind of preparation method of the reactive epoxies diluent of low total chlorine content |
| CN112279823A (en) * | 2020-10-22 | 2021-01-29 | 江苏扬农化工集团有限公司 | Method for preparing methyl glycidyl ether from epichlorohydrin by-product |
-
2021
- 2021-05-18 CN CN202110540486.8A patent/CN113372301A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1944487A (en) * | 2006-09-26 | 2007-04-11 | 蓝星化工新材料股份有限公司无锡树脂厂 | Preparing method for epoxy resin active diluent of low organic chlorine content |
| 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 |
| CN102766114A (en) * | 2012-06-25 | 2012-11-07 | 上海树脂厂有限公司 | Production method of epoxy active diluent |
| CN103191761A (en) * | 2013-03-13 | 2013-07-10 | 南京林业大学 | Catalyst, preparation method thereof and method for preparing aliphatic glycidyl ether by using catalyst |
| CN103333137A (en) * | 2013-06-25 | 2013-10-02 | 湖北恒鑫化工有限公司 | Method for synthesizing allyl glycidyl ether |
| CN106220828A (en) * | 2016-07-23 | 2016-12-14 | 辽阳鑫宇化工有限公司 | A kind of preparation method of the reactive epoxies diluent of low total chlorine content |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115028606A (en) * | 2022-05-26 | 2022-09-09 | 江苏扬农锦湖化工有限公司 | Preparation method of benzyl glycidyl ether |
| CN115960057A (en) * | 2022-12-29 | 2023-04-14 | 苏州元素集化学工业有限公司 | Method for preparing alkyl glycidyl ether by novel catalyst |
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