CN106496162A - 2, 3-butanediol diglycidyl ether and preparation method thereof - Google Patents
2, 3-butanediol diglycidyl ether and preparation method thereof Download PDFInfo
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- CN106496162A CN106496162A CN201610804230.2A CN201610804230A CN106496162A CN 106496162 A CN106496162 A CN 106496162A CN 201610804230 A CN201610804230 A CN 201610804230A CN 106496162 A CN106496162 A CN 106496162A
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- Prior art keywords
- butanediol
- butanediol diglycidyl
- diglycidyl ether
- mass fraction
- ether
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- PKLOCHBLBMUEFT-UHFFFAOYSA-N 2-[3-(oxiran-2-ylmethoxy)butan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)C(C)OCC1CO1 PKLOCHBLBMUEFT-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 29
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003822 epoxy resin Substances 0.000 claims abstract description 18
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 18
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims abstract description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000004593 Epoxy Substances 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 18
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000005292 vacuum distillation Methods 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 6
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- -1 ether compound Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- VIRPUNZTLGQDDV-UHFFFAOYSA-N chloro propanoate Chemical compound CCC(=O)OCl VIRPUNZTLGQDDV-UHFFFAOYSA-N 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
- 238000007142 ring opening reaction Methods 0.000 abstract description 9
- 238000010521 absorption reaction Methods 0.000 abstract description 6
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 abstract 2
- 239000012043 crude product Substances 0.000 abstract 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 150000002118 epoxides Chemical class 0.000 description 9
- 238000006266 etherification reaction Methods 0.000 description 8
- 238000007363 ring formation reaction Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000001514 detection method Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
- C07D301/28—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with hydroxyl radicals
-
- 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
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
Abstract
The invention provides 2, 3-butanediol diglycidyl ether and a preparation method thereof. The preparation method comprises the steps of carrying out ring-opening reaction on 2, 3-butanediol and epoxy chloropropane to generate an intermediate product chlorohydrin ether, reacting the chlorohydrin ether with alkali to synthesize a crude product of 2, 3-butanediol diglycidyl ether, and purifying the crude product to obtain a pure product of the 2, 3-butanediol diglycidyl ether. The epoxy value of the product obtained by the method is 9.28-9.92%, the viscosity at room temperature of 25 ℃ is 28-35 mPa.S, and the water absorption of the mixture after the epoxy resin E-44 is mixed and cured is reduced by 16-22% compared with that of the epoxy resin raw material.
Description
Technical field
The invention belongs to the field of chemical synthesis, is related to compound 2,3-butanediol diglycidyl ether, and its utilizes 2,3-
The method that butanediol prepares the compound.
Background technology
Epoxy resin is a kind of wide variety of thermoset macromolecule material.
Substantial amounts of epoxy resin adhesive is widely used in the electric control field of wet environment, such as conversion terminal case
Or the connection of telephone connection case, submarine optical fiber cable, the control electricity at the solenoid valve joint position, oil tanker and tank connections road of control water pipe
Cable joint position, railroad track electrical connection position etc., these crucial controlling positions are throughout the year in harsh working condition, Chang Yin
Dewing corrosion etc. causes electric fault, affects safety in production and equipment normally to run, it is therefore necessary to epoxy adhesive
Carry out performance Study of Lifting.
Epoxy resin in traditional application needs to add the diluent of (+)-2,3-Epoxy-1-propanol ethers using process to reduce which
In viscosity；In existing (+)-2,3-Epoxy-1-propanol ether product, how to be synthesized as initiator by different alcohol compounds.Common starting synthesis
Agent includes the linear diols such as ethylene glycol, diethylene glycol, 1,4- butanediols, 1,6-HD.For example, Chinese patent
" a kind of method of epoxy synthesis of bisphenol A diglycidyl ether " disclosed in CN103242264, is to be with quaternary ammonium salt phosphor-tungstic heteropoly acid
Catalyst, using one-step synthesis synthesizing glycidol ether.
Although existing glycidyl ether can reduce the operating viscosity of epoxy resin, in Properties of Epoxy Resin lifting side
Face effect is little, is not especially obviously improved in terms of wet environment and resistance to dewing corrosion to improving epoxy resin.Therefore,
It is highly desirable to develop new (+)-2,3-Epoxy-1-propanol ether product, lifts the performance of epoxy resin harsh conditions.
Content of the invention
The technical problem to be solved in the invention is the defect in order to solve prior art epoxy resin diluent, there is provided
A kind of new glycidyl ether diluent 2,3- butanediol diglycidyl ethers.In order to obtain the product, the present invention is also carried
The method for having supplied to synthesize the glycidyl ether.
Specifically, the technical scheme is that：
2,3-butanediol diglycidyl ether, wherein, the ether compound has following structural formula：.
The method for preparing 2,3-butanediol diglycidyl ether, wherein, the method includes step in detail below,
（1）Boron trifluoride diethyl etherate is added in 2,3-butanediol, then with excess epoxy chloropropane at 65 ~ 85 DEG C, is reacted 3 ~ 6 hours
Afterwards, vacuum distillation goes out excessive epoxychloropropane；
（2）2.0 ~ 3.0 times of 2,3-butanediol amount of substance of 25 ~ 50 DEG C of aqueous slkali is added in the system after vacuum distillation, instead
Answer 3 ~ 6 hours, obtain the mixture containing 2,3-butanediol diglycidyl ether；
（3）Removal inorganic salt is washed with deionized, acquisition 2,3-butanediol diglycidyl ether is isolated and purified.
Method of the present invention, wherein, the 2,3-butanediol：Boron trifluoride diethyl etherate：The mol ratio of epoxychloropropane
For 1:0.004~0.0015:2.0~2.8.
Method of the present invention, wherein, the alkali of the aqueous slkali is the one kind in sodium hydroxide and potassium hydroxide.
Method of the present invention, wherein, the alkali mass fraction of the aqueous slkali is 35 ~ 50%,
Method of the present invention, wherein, the step（1）When middle reaction terminates, the mass fraction of raw material 2,3-butanediol
No more than mass fraction 0.5%.
Application of the 2,3- butanediol diglycidyl ethers of the present invention in as epoxy resin diluent.
The beneficial effects of the present invention is
（1）The compound presents more excellent performance in the application as epoxy resin diluent, and its epoxide number is
9.28% ~ 9.92%, the viscosity that 25 DEG C of room temperature is 28 ~ 35mPa S..
（2）For from know-why, the compound initiator of present invention synthesis is 2,3-butanediol;2,3- butanediols
Containing hydrophobicity branched chain methyl in molecular structure, therefore, there is excellent hydrophobic performance with its compound for synthesizing.Which synthesizes product
Thing 2,3-butanediol diglycidyl ether is after mixing cured with epoxy resin E-44, plus synthetic product is not than adding synthetic product
Water absorption rate reduces 16 ~ 22%.
（3）The invention provides the preparation method of 2,3-butanediol diglycidyl ether, the method has easy to operate, reaction
Process is easily controlled, and product viscosity is low, the low advantage of colourity.
Description of the drawings
The infrared spectrum collection of illustrative plates of Fig. 1 2,3- butanediol diglycidyl ethers.Knowable to infrared spectrum analysiss：2976cm-1Place
For-CH3Stretching vibration peak；2874cm-1Locate as-CH2- stretching vibration peak；1125cm-1,1106cm-1Locate as-C-O-C-'s
Stretching vibration peak；1253cm-1Locate the symmetrical stretching vibration for epoxy radicals；911.89cm-1,854.43cm-1Locate as epoxy radicals not
Symmetrical stretching vibration.
Specific embodiment
Embodiment 1：This example demonstrates that the method for 2,3- butanediol diglycidyl ethers synthesis
Ring opening etherification reaction process：By 18 grams of 2,3-butanediol, the 0.22 gram of mixing of catalyst boron trifluoride diethyl etherate, then to system
37 grams of epoxychloropropane of middle Deca, carry out ring opening etherification reaction at 65 DEG C, after reacting 4 hours, former with gas chromatographic detection reaction
The mass fraction of material 2,3-butanediol is not more than the 0.5% of mass fraction, and vacuum distillation goes out excessive epoxychloropropane.
Ring-closure reaction process：24 grams of sodium hydroxide are added in above-mentioned reaction system, mass fraction is 40%, enters at 25 DEG C
Row ring-closure reaction, after reacting 5 hours, stopped reaction, the inorganic salt and other material being washed with deionized out in reaction system, rotation
Evaporation obtains final product 2,3- butanediol diglycidyl ethers.After testing, product yield 78.39%（With 2,3- butanediol diglycidyl ethers
Meter）, viscosity is 29mPa S（25℃）, according to GB/T1677-2008, it is 9.65% to measure epoxide number to epoxide number measure.
It is 1 according to mass ratio:Synthetic product is mixed by 10 with epoxy resin E-44, and system viscosity reduces by 42%, is inhaled after solidification
Water rate is determined according to GB1738-79, plus synthetic product is not than adding the water absorption rate of synthetic product to reduce by 21%.
Embodiment 2：This example demonstrates that the other method of 2,3- butanediol diglycidyl ethers synthesis
Ring opening etherification reaction process：By 27.04 grams of 2,3-butanediol, the 0.21 gram of mixing of catalyst boron trifluoride diethyl etherate, Ran Houxiang
77.7 grams of epoxychloropropane of Deca in system, carry out ring opening etherification reaction at 85 DEG C, after reacting 3 hours, use gas chromatographic detection
The mass fraction of reaction raw materials 2,3-butanediol is not more than the 0.5% of mass fraction, and vacuum distillation goes out excessive epoxychloropropane.
Ring-closure reaction process：33.6 grams of potassium hydroxide are added in above-mentioned reaction system, mass fraction is 50%, at 45 DEG C
Ring-closure reaction is carried out, after reacting 6 hours, stopped reaction, the inorganic salt and other material being washed with deionized out in reaction system, rotation
Turn evaporation and obtain final product 2,3- butanediol diglycidyl ethers.Product yield 85.87%（In terms of 2,3- butanediol diglycidyl ethers）,
Viscosity is 33mPa S（25℃）, according to GB/T1677-2008, it is 9.89% to measure epoxide number to epoxide number measure.
It is 1 according to mass ratio:Synthetic product is mixed by 10 with epoxy resin E-44, and system viscosity reduces by 39%, is inhaled after solidification
Water rate is determined according to GB1738-79, plus synthetic product is not than adding the water absorption rate of synthetic product to reduce by 20%.
Embodiment 3：This example demonstrates that the other method of 2,3- butanediol diglycidyl ethers synthesis
Ring opening etherification reaction process：By 9 grams of 2,3-butanediol, the 0.18 gram of mixing of catalyst boron trifluoride diethyl etherate, then to system
20.35 grams of epoxychloropropane of middle Deca, carry out ring opening etherification reaction at 75 DEG C, after reacting 5 hours, are reacted with gas chromatographic detection
The mass fraction of raw material 2,3-butanediol is not more than the 0.5% of mass fraction, and vacuum distillation goes out excessive epoxychloropropane.
Ring-closure reaction process：10 grams of sodium hydroxide are added in above-mentioned reaction system, mass fraction is 40%, enters at 35 DEG C
Row ring-closure reaction, after reacting 3 hours, stopped reaction, the inorganic salt and other material being washed with deionized out in reaction system, rotation
Evaporation obtains final product 2,3- butanediol diglycidyl ethers.Product yield 80.87%（In terms of 2,3- butanediol diglycidyl ethers）, stick
Spend for 30mPa S（25℃）, according to GB/T1677-2008, it is 9.58% to measure epoxide number to epoxide number measure.
It is 1 according to mass ratio:Synthetic product is mixed by 10 with epoxy resin E-44, and system viscosity reduces by 40%, is inhaled after solidification
Water rate is determined according to GB1738-79, plus synthetic product is not than adding the water absorption rate of synthetic product to reduce by 18%.
Embodiment 4：
Ring opening etherification reaction process：By 13.5 grams of 2,3-butanediol, the 0.24 gram of mixing of catalyst boron trifluoride diethyl etherate, then to body
34.68 grams of epoxychloropropane of Deca in system, carry out ring opening etherification reaction at 70 DEG C, after reacting 6 hours, anti-with gas chromatographic detection
The mass fraction of raw material 2,3-butanediol is answered to be not more than the 0.5% of mass fraction, vacuum distillation goes out excessive epoxychloropropane.
Ring-closure reaction process：23.52 grams of potassium hydroxide are added in above-mentioned reaction system, mass fraction is 50%, at 30 DEG C
Ring-closure reaction is carried out, after reacting 5 hours, stopped reaction, the inorganic salt and other material being washed with deionized out in reaction system, rotation
Turn evaporation and obtain final product 2,3- butanediol diglycidyl ethers.Product yield 80.25%（In terms of 2,3- butanediol diglycidyl ethers）,
Viscosity is 33mPa S（25℃）, according to GB/T1677-2008, it is 9.72% to measure epoxide number to epoxide number measure.
It is 1 according to mass ratio:Synthetic product is mixed by 10 with epoxy resin E-44, and system viscosity reduces by 37%, is inhaled after solidification
Water rate is determined according to GB1738-79, plus synthetic product is not than adding the water absorption rate of synthetic product to reduce by 22%.
Claims (7)
1.2,3- butanediol diglycidyl ethers, it is characterised in that the ether compound has following structural formula：
.
2. the method for preparing 2,3-butanediol diglycidyl ether, it is characterised in that the method includes step in detail below,
（1）Boron trifluoride diethyl etherate is added in 2,3-butanediol, then with excess epoxy chloropropane at 65 ~ 85 DEG C, is reacted 3 ~ 6 hours
Afterwards, vacuum distillation goes out excessive epoxychloropropane；
（2）2.0 ~ 3.0 times of 2,3-butanediol amount of substance of 25 ~ 45 DEG C of aqueous slkali is added in the system after vacuum distillation, instead
Answer 3 ~ 6 hours, obtain the mixture containing 2,3-butanediol diglycidyl ether；
（3）Removal inorganic salt is washed with deionized, acquisition 2,3-butanediol diglycidyl ether is isolated and purified.
3. method according to claim 2, it is characterised in that the 2,3-butanediol：Boron trifluoride diethyl etherate：Epoxy chloropropionate
The mol ratio of alkane is 1:0.004~0.0015:2.0~2.8.
4. method according to claim 2, it is characterised in that the alkali of the aqueous slkali is in sodium hydroxide and potassium hydroxide
One kind.
5. method according to claim 2, it is characterised in that the alkali mass fraction of the aqueous slkali is 35 ~ 50%.
6. method according to claim 2, it is characterised in that the step（1）When middle reaction terminates, raw material 2,3- fourths
The mass fraction of glycol is not more than the 0.5% of mass fraction.
7. application of the 2,3- butanediol diglycidyl ethers described in claim 1 in as epoxy resin diluent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201610804230.2A CN106496162A (en) | 2016-09-05 | 2016-09-05 | 2, 3-butanediol diglycidyl ether and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106995421A (en) * | 2017-04-02 | 2017-08-01 | 湖北绿色家园材料技术股份有限公司 | A kind of production method of the butanediol diglycidyl ether of low in hydrolysis chlorine 1,4 |
| CN116063248A (en) * | 2022-12-07 | 2023-05-05 | 山东尚正新材料科技股份有限公司 | Method for continuously producing biomass glycidyl ether |
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