CN1241888C - Synthetic method for propylend glycol dimethyl ether - Google Patents
Synthetic method for propylend glycol dimethyl ether Download PDFInfo
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- CN1241888C CN1241888C CN 200310112773 CN200310112773A CN1241888C CN 1241888 C CN1241888 C CN 1241888C CN 200310112773 CN200310112773 CN 200310112773 CN 200310112773 A CN200310112773 A CN 200310112773A CN 1241888 C CN1241888 C CN 1241888C
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- propylene glycol
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- ether
- alkylating agent
- alkali
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- 238000010189 synthetic method Methods 0.000 title claims abstract 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 title abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 66
- 238000006243 chemical reaction Methods 0.000 claims abstract description 63
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims abstract description 52
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 42
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000002168 alkylating agent Substances 0.000 claims abstract description 20
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 20
- 239000003513 alkali Substances 0.000 claims abstract description 16
- 229940050176 methyl chloride Drugs 0.000 claims abstract description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 12
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims abstract description 11
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 9
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims abstract description 5
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims description 17
- 150000001983 dialkylethers Chemical class 0.000 claims description 11
- 229920001281 polyalkylene Polymers 0.000 claims description 11
- 238000001308 synthesis method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- 239000000047 product Substances 0.000 abstract description 9
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 238000007086 side reaction Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000006266 etherification reaction Methods 0.000 description 11
- 239000012043 crude product Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004321 preservation Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IEVFIRYNECRBRK-UHFFFAOYSA-N [Na].COCC(C)O Chemical compound [Na].COCC(C)O IEVFIRYNECRBRK-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- -1 compound compounds Chemical class 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000012658 bimolecular nucleophilic substitution Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention relates to a synthetic method of propylend glycol dimethyl ether, which is characterized in that propylene glycol methyl ether, alkali and an alkylating agent are used as raw materials and react at the reaction temperature of 40 to 90 DEG C to obtain the propylene glycol dimethyl ether, wherein the alkali can be sodium hydroxide, sodium methylate, potassium hydroxide or potassium methoxide, and the alkylating agent can be methyl chloride, dimethyl sulphate or dimethyl carbonate. When the alkylating agent is methyl chloride or dimethyl sulphate, the charge ratio of the raw materials of propylene glycol methyl ether to alkali to alkylating agent is 1:1.0 to 2.0:1.0 to 1.3(molar ratio) in the reaction; when the alkylating agent is dimethyl carbonate, the charge ratio of the raw materials of propylene glycol methyl ether to alkali to alkylating agent is 1:1.0 to 2.0:0.5 to 0.65(molar ratio) in the reaction. The synthetic method has the advantages of mild reaction condition, high production safety, high selectivity of the reaction product, fewer side reactions, high product purity, simple technological process and easy industrialization.
Description
The technical field is as follows:
the invention relates to a synthesis method of propylene glycol dimethyl ether, belonging to the technical field of organic chemical industry.
Secondly, background art:
the chemical name of the propylene glycol dimethyl ether is 1, 2-dimethoxypropane, and the structural formula is as follows: CH (CH)3OCH2CH(CH3)OCH3. The propylene glycol dimethyl ether is used as a novel low-toxicity aprotic polar solvent which is easy to solvate cationic substances, and can be used in the chemical process fields of electrochemistry, polar organic reaction, anion polymerization, coordination ion polymerization and the like; the method is used in the physical processing fields of extraction, stabilization and the like; can also be used for industrial products such as lubricant, fabric, medicine, pesticide and the like; but also can be widely applied to cleaning agents, extracting agents, stabilizing agents, cosolvent, organic synthesis reaction solvents, additives, wetting solvents and the like.
The research on the synthesis of propylene glycol dimethyl ether is less reported. According to theclassical etherification synthesis method, the following three methods are mainly summarized for the synthesis of the well-known propylene glycol dimethyl ether: 1. propylene glycol methyl ether and methanol are subjected to intermolecular dehydration, and the same intermolecular dehydration is easy to occur in the reaction process, so that a series of by-product ethers are generated, and the purity of the product is influenced. 2. The ring opening reaction of propylene oxide and methyl ether is carried out under the condition of pressurization, and the polymerization of propylene oxide is easy to occur when an epoxy bond is opened, so that a series of higher molecular homologous compound compounds are formed. 3. Williamson (Williamson) etherification synthesis. The traditional Williamson etherification synthesis method is to firstly prepare propylene glycol methyl ether and metallic sodium (or NaNH)2) The reaction is carried out to generate propylene glycol methyl ether sodium, and then the propylene glycol methyl ether sodium reacts with methyl halide to generate propylene glycol dimethyl ether:
Thirdly, the invention content:
the invention aims to provide a method for synthesizing propylene glycol dimethyl ether with high safety, high conversion rate and less byproducts.
The technical content of the invention is a method for synthesizing propylene glycol dimethyl ether, which is characterized in that propylene glycol methyl ether, alkali and alkylating agent are used as raw materials, polyalkylene dialkyl ether is used as a catalyst, and the reaction is carried out at the reaction temperature of 40-90 ℃ to prepare the propylene glycol dimethyl ether product, wherein the alkali is sodium hydroxide, sodium methoxide, potassium hydroxide or potassium methoxide, and the alkylating agent is methyl chloride, dimethyl sulfate or dimethyl carbonate; wherein when the alkylating agent is methyl chloride or dimethyl sulfate, the feeding proportion of the raw materials in the reaction is 1: 1.0-2.0: 1.0-1.3 (molar ratio) of propylene glycol methyl ether, alkali and alkylating agent; when the alkylating agent is dimethyl carbonate, the feeding proportion of the raw materials in the reaction is that propylene glycol methyl ether, alkali and the alkylating agent are 1: 1.0-2.0: 0.5-0.65 (molar ratio); the structural formula of the catalyst polyalkylene dialkyl ether is R1O[CH2CH(R2)O]nCH3Wherein R is1＝C1～4Alkyl radical, R2＝H、CH3N is 4-10; the dosage of the catalyst is 20-100% of propylene glycol methyl ether by mass. The invention is suitable for reaction under normal pressure because of low requirements on equipment and less side reactions under normal pressure.
The alkali used in the present invention is preferably sodium hydroxide because sodium hydroxide is relatively inexpensive.
The alkylating agent used in the invention is high in toxicity of dimethyl sulfate and high in price of dimethyl carbonate, and is best in chloromethane.
A typical reaction is as follows:
The proper feeding ratio of propylene glycol methyl ether, sodium hydroxide and chloromethane is 1: 1.2-1.6: 1.05-1.15 (molar ratio), and the optimal feeding ratio is 1: 1.3: 1.1 (molar ratio).
The reaction temperature suitable for preparing the propylene glycol dimethyl ether is 50-80 ℃; the optimal reaction temperature is 60-70 ℃.
The invention adopts sodium hydroxide to replace metal sodium; because solid sodium hydroxide or sodium hydroxide solution is not dissolved in an organic phase, the conversion rate of propylene glycol methyl ether is relatively reduced, and a phase transfer catalyst is gradually introduced in the chemical synthesis process. The catalyst used in the reaction can make the reaction have better effect. The mechanism of the phase transfer catalytic reaction is as follows: in the organic reaction of a multiphase system, the reaction among multiple phases can be transferred into an organic phase to be carried out, so that the reaction is accelerated, and the reaction process comprises the following steps:
Q+Y-+X-＝＝＝Q+X-+Y-aqueous phase
-x-c interface
Q+Y-+RX→Q+X-+ RY organic phase
In the formula: QX- -surfactant, RX- -reactant, RY- -reaction product.
The catalyst polyalkylene dialkyl ether adopted by the invention is an aprotic polar solvent, has a solubilizing effect on sodium hydroxide, and simultaneously plays a role of a diluent, so that solid and gas materials are dispersed and dissolved in a solution in the reaction process, the contact between reactants is increased, and the effect of improving the reaction conversion rate is achieved.
The catalyst polyalkylene dialkyl ether can be purchased from the market or prepared by adopting the known preparation technology, and is prepared by reacting lower alcohol with ethylene oxide and propylene oxide to prepare polyalkylene monoalkyl ether and then carrying out etherification and end capping reaction with alkali and chloromethane.
The proper dosage of the polyalkylene dialkyl ether catalyst is 30-70% (mass percent) of propylene glycol methyl ether, and the optimal dosage of the catalyst is 40-60% (mass percent) of propylene glycol methyl ether.
The propylene glycol dimethyl ether prepared by the invention is subjected to solid-liquid separation such as filtration or extraction to remove solid byproduct salt, and then is subjected to rectification and dehydration refining to prepare a high-purity propylene glycol dimethyl ether product. Rectifying in a rectifying tower with more than 20 tower plates to obtain propylene glycol dimethyl ether product with purity of more than 99.8% by gas chromatographic analysis.
The polyalkylene dialkyl ether catalyst and the product propylene glycol dimethyl ether used in the invention are separated by rectification in a rectifying still and can be recycled.
The invention has the advantages that: the reaction condition is mild, and the production safetyis good; the reaction product has high selectivity, less side reaction and high product purity; the process flow is simple and easy to realize industrialization.
Fourthly, the specific embodiment:
the invention is further described below by way of examples, but without being limited thereto.
The raw material used by the invention is propylene glycol monomethyl ether with industrial grade, the purity is more than 99 percent, and the Jiangyin Yida chemical industry company is produced; sodium hydroxide is of industrial grade, the purity is more than 96 percent, and the sodium hydroxide is produced in a combined fertilizer chemical plant; sodium methoxide is of industrial grade, the purity is more than 96 percent, and the sodium methoxide is imported from Japan; the monochloromethane is of industrial grade, the purity is more than 99.5 percent, and the product is produced by Zhejiang sublimation group chemical company Limited; dimethyl sulfate is industrial grade, the purity is more than 99 percent, and the dimethyl sulfate is produced by the chemical industry Limited company in the market of tin-free poplar; dimethyl carbonate is industrial grade, the purity is more than 99 percent, and the dimethyl carbonate is produced in a chemical plant of Tangshan and Chaoyang; the polyalkylene dialkyl ether catalysts are prepared by known preparative techniques.
Example 1
Adding 225g of propylene glycol monomethyl ether and 130g of sodium hydroxide into a 1000ml four-neck flask provided with a mechanical stirrer with a mechanical seal, a reflux condenser and a thermometer respectively, starting the stirrer, heating to 60 ℃ for reaction for 1h, introducing 139g of methyl chloride gas for etherification reaction, controlling the reaction temperature to be 60-70 ℃, completing the addition within 6h, stopping introducing chloromethane, continuing the heat preservation reaction for 1h, and finishing the reaction. Cooling to room temperature, filtering to obtain 237g of crude product, and analyzing the content of propylene glycol dimethyl ether by gas chromatography to obtain 81.3 percent.
Example 2
Adding 225g of propylene glycol monomethyl ether and 145g of sodium methoxide into a 1000ml four-neck flask provided with a mechanical stirrer with a mechanical seal, a reflux condenser and a thermometer respectively, starting the stirrer, heating to 50 ℃ for reaction for 1h, introducing 139g of methyl chloride gas for etherification reaction, controlling the reaction temperature to be 50-60 ℃, completing the addition within 6h, stopping introducing methyl chloride, continuing the heat preservation reaction for 1h, and finishing the reaction. Cooling to room temperature, filtering to obtain 301g of crude product, and analyzing the content of propylene glycol dimethyl ether by gas chromatography to obtain 62.7 percent.
Example 3
Adding 225g of propylene glycol monomethyl ether and 150g of sodium hydroxide into a 1000ml four-neck flask provided with a mechanical stirrer with a mechanical seal, a reflux condenser and a thermometer respectively, starting the stirrer, heating to 70 ℃ for reaction for 1h, dropwise adding 315g of dimethyl sulfate for etherification reaction, controlling the reaction temperature to be 70-80 ℃, completing the addition within 6h, stopping dropwise adding the dimethyl sulfate, continuing the heat preservation reaction for 1h, and finishing the reaction. Cooling to room temperature, filtering to obtain crude product 227g, and analyzing the content of propylene glycol dimethyl ether by gas chromatography for 76.5%.
Example 4
Adding 225g ofpropylene glycol monomethyl ether and 130g of sodium hydroxide into a 1000ml four-neck flask provided with a mechanical stirrer with mechanical seal, a reflux condenser and a thermometer respectively, starting the stirrer, heating to 50 ℃ for reaction for 1h, dropwise adding 118g of dimethyl carbonate for etherification reaction, controlling the reaction temperature to be 50-60 ℃, completing the addition within 6h, stopping dropwise adding the dimethyl carbonate, continuing the heat preservation reaction for 1h, and finishing the reaction. Cooling to room temperature, filtering to obtain crude product 231g, and analyzing the content of propylene glycol dimethyl ether by gas chromatography to obtain 77.5 percent.
Example 5
Adding 225g of propylene glycol monomethyl ether, 200g of propylene glycol dimethyl ether (with the purity of 99.8%) and 150g of sodium hydroxide into a 1000ml four-neck flask provided with a mechanical stirrer with a mechanical seal, a reflux condenser and a thermometer respectively, starting the stirrer, heating to 60 ℃, reacting for 1h, introducing 155g of methyl chloride gas for etherification reaction, controlling the reaction temperature to be 60-70 ℃, completing the addition within 6h, stopping introducing chloromethane, continuing to perform heat preservation reaction for 1h, and finishing the reaction. Cooling to room temperature, filtering to obtain 427g of crude product, and analyzing the content of propylene glycol dimethyl ether by gas chromatography to obtain 81.1% of propylene glycol monomethyl ether.
Example 7
Adding 225g of propylene glycol monomethyl ether, 150g of sodium hydroxide and 225g of polyalkylene dialkyl ether into a 1000ml four-neck flask provided with a mechanical stirrer with a mechanical seal, a reflux condenser and a thermometer respectively, starting the stirrer, heating to 70 ℃ for reaction for 1h, introducing 150g of methyl chloride gas for etherification reaction, controlling the reaction temperature to be 70-80 ℃, finishing the addition within 6h, continuing the heat preservation reaction for 1h after stopping introducing the methyl chloride, and finishing the reaction. Cooling to room temperature, filtering to obtain 478g of crude product, distilling to obtain 257g of propylene glycol dimethyl ether crude product, wherein the content of the propylene glycol dimethyl ether is 91.0 percent, and recovering 221g of the catalyst.
Example 8
Adding 225g of propylene glycol monomethyl ether, 130g of sodium hydroxide and 113g of polyalkylene glycol dialkyl ether into a 1000ml four-neck flask provided with a mechanical stirrer with a mechanical seal, a reflux condenser and a thermometer respectively, starting the stirrer, heating to 60 ℃ for reaction for 1h, introducing 139g of methyl chloride gas for etherification reaction, controlling the reaction temperature to be 60-70 ℃, finishing the addition within 6h, continuing the heat preservation reaction for 1h after stopping introducing the chloromethane, and finishing the reaction. Cooling to room temperature, filtering to obtain 310g of crude product, distilling to obtain 255g of crude product of propylene glycol dimethyl ether with the content of 95.0 percent of propylene glycol dimethyl ether, and recovering 111g of catalyst.
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| CN 200310112773 CN1241888C (en) | 2003-12-26 | 2003-12-26 | Synthetic method for propylend glycol dimethyl ether |
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|---|---|---|---|
| CN 200310112773 CN1241888C (en) | 2003-12-26 | 2003-12-26 | Synthetic method for propylend glycol dimethyl ether |
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| WO2015094716A1 (en) * | 2013-12-20 | 2015-06-25 | Archer Daniels Midland Company | Synthesis of isohexide ethers and carbonates |
| CN103641694B (en) * | 2013-12-20 | 2015-08-12 | 安徽立兴化工有限公司 | A kind of preparation method of dipropylene glycol dipropyl ether |
| CN110452102A (en) * | 2019-08-30 | 2019-11-15 | 苏州汉德创宏生化科技有限公司 | A kind of synthetic method of 3- methoxyl group -3- methyl butyne |
| CN112246279B (en) * | 2020-07-09 | 2021-10-01 | 上海芾楠企业服务中心 | Catalyst and preparation method of ethylene glycol dimethyl ether |
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