CN107814690B - Method for converting ethylene glycol monomethyl ether - Google Patents
Method for converting ethylene glycol monomethyl ether Download PDFInfo
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- CN107814690B CN107814690B CN201610826593.6A CN201610826593A CN107814690B CN 107814690 B CN107814690 B CN 107814690B CN 201610826593 A CN201610826593 A CN 201610826593A CN 107814690 B CN107814690 B CN 107814690B
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- molecular sieve
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
The invention provides a method for converting ethylene glycol monomethyl ether, in particular to a method for converting ethylene glycol monomethyl ether into ethylene glycol and ethylene glycol ether in a liquid phase or gas-liquid mixed state, which is characterized in that a catalyst containing one or more of a ZSM-11 molecular sieve, a ZSM-22 molecular sieve, a ZSM-23 molecular sieve, an MCM-22 molecular sieve with a silicon-aluminum molecular ratio of 15-50, an MCM-56 molecular sieve, an MCM-49 molecular sieve, an SAPO-5 molecular sieve, an SAPO-11 molecular sieve and an SAPO-34 molecular sieve is adopted. The method has the advantages of low reaction temperature, high selectivity and long service life of the catalyst.
Description
Technical Field
The invention relates to a method for converting ethylene glycol monomethyl ether into ethylene glycol and ethylene glycol ether in a liquid phase or gas-liquid mixed state, belonging to the field of chemical engineering.
Background
At present, ethylene glycol is produced mainly by an ethylene oxide hydration method, namely ethylene is used as a raw material, ethylene oxide is generated through an oxidation reaction, and ethylene glycol is obtained through the hydration reaction of the ethylene oxide.
Due to the decreasing petroleum resources, the technology for preparing ethylene glycol by non-ethylene oxide route has attracted much attention, including direct synthesis of ethylene glycol from synthesis gas, indirect synthesis via oxalate, indirect synthesis of methanol formaldehyde, and the like.
The methanol-formaldehyde route is a method that firstly methylal is synthesized by methanol and formaldehyde, the methylal and CO are subjected to carbonylation reaction to synthesize methyl methoxyacetate, then ethylene glycol monomethyl ether is obtained by hydrogenation, and ethylene glycol is obtained by hydrolysis reaction.
Chinese patent publication No. CN104119228A discloses a method for synthesizing methyl methoxyacetate by carbonylation of methylal and CO, which adopts MWW type molecular sieve as catalyst and a gas-solid phase fixed bed reactor.
However, the technology of converting ethylene glycol monomethyl ether into ethylene glycol or other products has not been reported.
Disclosure of Invention
The invention aims to provide a method for converting ethylene glycol monomethyl ether into ethylene glycol and ethylene glycol ether in a liquid phase or gas-liquid mixed state.
The method is characterized by comprising the step of contacting a material containing ethylene glycol monomethyl ether with a molecular sieve catalyst and carrying out reaction, wherein the molecular sieve catalyst contains one or more of a ZSM-11 molecular sieve, a ZSM-22 molecular sieve, a ZSM-23 molecular sieve, an MCM-22 molecular sieve with a silicon-aluminum molecular ratio of 15-50, an MCM-56 molecular sieve, an MCM-49 molecular sieve, an SAPO-5 molecular sieve, an SAPO-11 molecular sieve and an SAPO-34 molecular sieve.
The method has the advantages of low reaction temperature, high selectivity and long service life of the catalyst.
Detailed Description
The present inventors have conducted intensive studies and found that the conversion of ethylene glycol monomethyl ether into ethylene glycol and ethylene glycol ether can be promoted when a specific molecular sieve is used and the reaction conditions are controlled, thereby completing the present invention.
The method is characterized by comprising the step of contacting a material containing ethylene glycol monomethyl ether with a molecular sieve catalyst and carrying out reaction, wherein the molecular sieve catalyst contains one or more of a ZSM-11 molecular sieve, a ZSM-22 molecular sieve, a ZSM-23 molecular sieve, an MCM-22 molecular sieve with a silicon-aluminum molecular ratio of 15-50, an MCM-56 molecular sieve, an MCM-49 molecular sieve, an SAPO-5 molecular sieve, an SAPO-11 molecular sieve and an SAPO-34 molecular sieve.
In order to achieve the purpose, the catalyst provided by the invention is a molecular sieve catalyst.
The molecular sieve catalyst comprises 50-95% of a molecular sieve and 5-50% of a binder based on the dry weight of the molecular sieve catalyst. The molecular sieve catalyst contains one or more of a ZSM-11 molecular sieve, a ZSM-22 molecular sieve, a ZSM-23 molecular sieve, an MCM-22 molecular sieve with a silicon-aluminum molecular ratio of 15-50, an MCM-56 molecular sieve, an MCM-49 molecular sieve, an SAPO-5 molecular sieve, an SAPO-11 molecular sieve and an SAPO-34 molecular sieve. The cation in the molecular sieve is hydrogen ion. According to certain embodiments of the invention, the hydrogen ions in the molecular sieve are partially or fully substituted with one or more of Mg ions, Ca ions, La ions and Cu ions. Further, according to certain embodiments of the invention, the molecular sieve is impregnated with one or more of P, Ti, Zr, and La prior to use. Preferably, the molecular sieve is one or more of a ZSM-22 molecular sieve, a ZSM-23 molecular sieve and an MCM-22 molecular sieve with the silicon-aluminum molecular ratio of 15-50.
The molecular sieve raw powder can be obtained by a common hydrothermal method or other methods, and is subjected to ammonium ion exchange after being roasted to remove a template agent, then is mixed with a proper binder, is extruded into strips and is finally roasted to remove ammonia to obtain the corresponding catalyst containing the hydrogen type molecular sieve. Or mixing the molecular sieve raw powder with a binder, extruding into strips, and then carrying out the steps of roasting to remove the template agent, ammonium exchange and roasting to remove ammonia. The step of calcination to remove the templating agent can also be performed after the ammonium exchange along with calcination to remove ammonia. Other forming methods than extrusion may also be employed. The binder is usually one or more of alumina, silica and kaolin.
The catalyst containing the molecular sieve is subjected to steam treatment, so that the stability of the catalyst can be improved, and the service life of the catalyst can be prolonged. The temperature of the steam treatment is generally 350 to 650 ℃. For certain molecular sieves, steam treatment under appropriate conditions is also beneficial to increase the reactivity of the catalyst.
Under the condition of liquid phase or gas-liquid mixing and under the action of the above-mentioned catalyst,
ethylene glycol monomethyl ether can undergo the following reversible reactions:
similar reactions to those described above can also occur between the polyethylene glycol monomethyl ethers and ethylene glycol monomethyl ethers to produce the corresponding ethylene glycol or polyethylene glycol and longer-chain ethylene glycol ethers.
Intermolecular condensation dehydration reactions between ethylene glycol and poly (ethylene glycol) can also occur to produce poly (ethylene glycol) with longer vinylene chains, such as:
when water exists (the water can be added into the raw material of ethylene glycol monomethyl ether in advance or generated in the reaction), the ethylene glycol and the mono-methyl ether or dimethyl ether of the polyglycols can generate reversible hydrolysis reaction to generate corresponding mono-methyl ether or glycol and methanol:
n is 1, 2, 3, etc
When methanol exists (the methanol can be added into the ethylene glycol monomethyl ether raw material in advance or generated by the reaction), the reverse reactions of the reactions (5) and (6) are generated, namely the ethylene glycol and the polyglycols or the monomethyl ether thereof and the methanol generate the corresponding monomethyl ether or dimethyl ether and water by the reversible dehydration reaction.
In addition, methanol can undergo an intermolecular dehydration reaction to produce dimethyl ether and water, and diethylene glycol can undergo an intramolecular dehydration reaction to produce dioxane and water:
ethylene glycol and ethylene glycol monomethyl ether undergo decomposition reaction to produce a very small amount of ethylene oxide
The above reactions are reversible reactions and are limited by chemical equilibrium.
The method can be used for producing ethylene glycol and ethylene glycol dimethyl ether from ethylene glycol monomethyl ether.
If the main target product is glycol and methanol and dimethyl ether are byproducts simultaneously, a certain amount of water can be added into the reaction raw material of the glycol monomethyl ether to make the chemical equilibrium move towards the direction of generating the glycol. The molar ratio of water to ethylene glycol monomethyl ether added is in the range of 1 to 15, preferably 2 to 10, more preferably 2.5 to 6, and good effects can be obtained.
If the main target product is ethylene glycol dimethyl ether, a certain amount of methanol can be added into the ethylene glycol monomethyl ether reaction raw material to move the chemical equilibrium to the direction of generating ethylene glycol dimethyl ether. The molar ratio of methanol to ethylene glycol monomethyl ether added is in the range of 0.5 to 10, preferably 1 to 6, more preferably 1.5 to 3, and good effects can be obtained.
Thus, the ethylene glycol monomethyl ether-containing feed may contain water, methanol, or a portion of the reaction product recycled from the conversion reaction.
The reaction (8) for producing dioxane using the catalyst of the present invention is slow, and the amount of the product is usually small although the chemical equilibrium constant of the reaction is large.
In addition to the above reaction products, other by-products are produced in a small amount.
In practical application, after the mixture after reaction is separated as required to obtain the required target product ethylene glycol and/or ethylene glycol dimethyl ether, other products are circularly reacted, and finally the ethylene glycol monomethyl ether is completely converted into the required target product.
The process for the conversion of ethylene glycol monomethyl ether according to the present invention can be carried out in a fixed bed reactor, a tank reactor or a catalytic distillation reactor. The reaction temperature is 140-240 ℃, the pressure is 0.3-8.0 MPa, and the feeding volume space velocity of the ethylene glycol monomethyl ether is 0.1-10 ml/(ml catalyst. h). The preferable reaction temperature is 160-220 ℃, and the reaction pressure is 1.5-4.0 MPa.
Examples
The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
The symbols in the table have the following meanings:
x: ethylene glycol monomethyl ether conversion S: selectivity by carbon number
T: reaction temperature t: reaction time
DME: dimethyl ether MOH: methanol
EG: ethylene glycol EG-M: ethylene glycol monomethyl ether
EG-MM: ethylene glycol dimethyl ether DEG: diethylene glycol (diethylene glycol)
DEG-M: diethylene glycol monomethyl ether DEG-MM: diethylene glycol dimethyl ether
And (4) PEGE: other polyglycitol ethers, mainly triethylene glycol (triethylene glycol) and its monomethyl, dimethyl and ethylene oxides
DOX: dioxane x: other products
Example 1
Into a 160ml autoclave were charged 90 g of an aqueous solution of ethylene glycol monomethyl ether (molar ratio of water to ethylene glycol monomethyl ether: 5) and 4.5 g
The stripe-shaped ZSM-22 molecular sieve catalyst of (1%) comprising 70 wt% of HZSM-22 molecular sieve impregnated with 1% P (silica-alumina molecular ratio of 69) and 30 wt% of alumina binder. Heating the obtained mixture to 200 ℃ under stirring at the rotating speed of about 60 revolutions per minute, increasing the rotating speed to 210 revolutions per minute, reacting for 5 hours under autogenous pressure, then reducing the temperature to about 30 ℃, and opening the reaction kettle for sampling and analyzing. The contents of the respective components in the product were measured by a gas chromatograph, and the ethylene glycol monomethyl ether conversion (X) and the selectivities (S) of the respective components by carbon number were calculated. The reaction results are shown in Table 1.
Example 2
To a 160ml autoclave were charged 90 g of an aqueous solution of ethylene glycol monomethyl ether (molar ratio of water to ethylene glycol monomethyl ether: 4.9) and 4.5 g
The strip-shaped ZSM-23 molecular sieve catalyst contains 70 wt% of HZSM-23 molecular sieve (the ratio of silicon to aluminum is 110) and 30 wt% of alumina binder. Heating the obtained mixture to 190 ℃ under stirring at a rotating speed of about 60 revolutions per minute, increasing the rotating speed to about 210 revolutions per minute, reacting for 5 hours under autogenous pressure, then reducing the temperature to about 30 ℃, and opening the reaction kettle for sampling and analyzing. The contents of the respective components in the product were measured by gas chromatography, and the ethylene glycol monomethyl ether conversion (X) and the selectivity (S) by carbon number of the respective components were calculated. The reaction results are shown in Table 1.
Example 3
To a 160ml autoclave were added 90 g of ethylene glycol monomethyl ether and 4.5 g
The catalyst contains 80 wt% of CuMCM-22 molecular sieve (the ratio of silicon to aluminum is 20) and 20 wt% of alumina binder. Heating the obtained mixture to 200 ℃ under stirring at a rotating speed of about 60 revolutions per minute, increasing the rotating speed to about 210 revolutions per minute, reacting for 3 hours under autogenous pressure, then reducing the temperature to about 30 ℃, and opening the reaction kettle for sampling and analyzing. Measurement of product by gas chromatographThe contents of the various components, and the ethylene glycol monomethyl ether conversion (X) and the selectivity (S) by carbon number of the various components were calculated. The reaction results are shown in Table 1.
Example 4
Into a 160ml high-pressure reaction vessel were charged 90 g of an aqueous solution of ethylene glycol monomethyl ether (molar ratio of water to ethylene glycol monomethyl ether: 4.9) and 9.0 g
The SAPO-11 molecular sieve catalyst of (1), (75) wt% hydrogen type SAPO-11 molecular sieve impregnated with 0.5 wt% Zr (Al: P: Si: 1: 0.85: 0.26, atomic ratio) and 25 wt% alumina binder. Heating the obtained mixture to 200 ℃ under stirring at the rotating speed of about 60 revolutions per minute, increasing the rotating speed to 210 revolutions per minute, reacting for 5 hours under autogenous pressure, then reducing the temperature to about 30 ℃, and opening the reaction kettle for sampling and analyzing. The contents of the respective components in the product were measured by gas chromatography, and the ethylene glycol monomethyl ether conversion (X) and the selectivity (S) by carbon number of the respective components were calculated. The reaction results are shown in Table 1.
Example 5
To a 160ml autoclave were charged 90 g of an aqueous solution of ethylene glycol monomethyl ether (molar ratio of water to ethylene glycol monomethyl ether: 4.9) and 9.0 g
The SAPO-34 molecular sieve catalyst contains 80 wt% of calcium hydrogen type SAPO-34 molecular sieve (Al: P: Si: Ca is 1: 0.78: 0.45: 0.05, atomic ratio) and 20 wt% of alumina binder. The obtained mixture is heated to 240 ℃ under the stirring of the rotation speed of about 60 revolutions per minute, the rotation speed is increased to 210 revolutions per minute, the reaction is carried out for 5 hours under the autogenous pressure and then is cooled to about 30 ℃, and the reaction kettle is opened for sampling and analysis. The contents of the respective components in the product were measured by gas chromatography, and the ethylene glycol monomethyl ether conversion (X) and the selectivity (S) by carbon number of the respective components were calculated. The reaction results are shown in Table 1.
Example 6
90 g of ethylene glycol monomethyl ether aqueous solution (water and ethylene glycol monomethyl ether) is added into a 160ml high-pressure reaction kettleMolar ratio of ether 1) and 9.0 g
The SAPO-5 molecular sieve catalyst of (1) comprises 80 wt% of hydrogen type SAPO-5 molecular sieve (Al: P: Si: 1: 0.88: 0.12 in atomic ratio) impregnated with 1.2 wt% of La and 20 wt% of kaolin binder. The obtained mixture is heated to 240 ℃ under the stirring of the rotation speed of about 60 revolutions per minute, the rotation speed is increased to 210 revolutions per minute, the reaction is carried out for 5 hours under the autogenous pressure and then is cooled to about 30 ℃, and the reaction kettle is opened for sampling and analysis. The contents of the respective components in the product were measured by gas chromatography, and the ethylene glycol monomethyl ether conversion (X) and the selectivity (S) by carbon number of the respective components were calculated. The reaction results are shown in Table 1.
Example 7
6 g of the mixture is added into a fixed bed reactor with the inner diameter of 12mm
The catalyst of the strip molecular sieve is used for carrying out the conversion reaction of ethylene glycol monomethyl ether. The catalyst contained 80 wt% of H0.4Mg0.3ZSM-11 molecular sieve (silicon-aluminum molecular ratio of 38) and 20 wt% of alumina binder. When the reaction raw material is ethylene glycol monomethyl ether methanol solution (the molar ratio of methanol to ethylene glycol monomethyl ether is 5.0), the feeding airspeed is 5.8h-1(g/(g catalyst. multidot.hr)), 188 ℃ at a reaction temperature and 5MPa for 2 hours, and the reaction results obtained after stabilization are shown in Table 2.
Example 8
8 g of the mixture is added into a fixed bed reactor with the inner diameter of 12mm
The catalyst of the strip-shaped molecular sieve is used for carrying out the conversion reaction of ethylene glycol monomethyl ether. The catalyst contains 50 wt% of HMCM-22 molecular sieve (the ratio of silicon to aluminum is 27) and 50 wt% of alumina binder. When the reaction raw material is ethylene glycol monomethyl ether aqueous solution (the molar ratio of water to ethylene glycol monomethyl ether is 4.1), the feeding airspeed is 4.8h-1(g/(g catalyst. h)), reaction temperature 205 ℃ and reactionThe results of the reaction obtained after 2 hours of stabilization at a pressure of 5MPa are shown in Table 2.
Example 9
8 g of the mixture is added into a fixed bed reactor with the inner diameter of 12mm
The catalyst of the strip molecular sieve is used for carrying out the conversion reaction of ethylene glycol monomethyl ether. The catalyst contains 50 wt% of HMCM-49 molecular sieve (silicon-aluminum molecular ratio is 26) and 50 wt% of alumina binder. When the reaction raw material is ethylene glycol monomethyl ether aqueous solution (the molar ratio of water to ethylene glycol monomethyl ether is 3), the feeding airspeed is 2.0h-1(g/(g. CATALYST. multidot. hr)), the reaction temperature was 140 ℃ and the reaction pressure was 2MPa, and the reaction results obtained after 5 hours of stabilization are shown in Table 2.
Example 10
8 g of the mixture is added into a fixed bed reactor with the inner diameter of 12mm
The catalyst of the strip molecular sieve is used for carrying out the conversion reaction of ethylene glycol monomethyl ether. The catalyst contained 50 wt% of H0.7La0.1MCM-22 molecular sieve (27 Si/Al) and 50 wt% alumina binder. When the reaction raw material is ethylene glycol monomethyl ether aqueous solution (the molar ratio of water to ethylene glycol monomethyl ether is 15), the feeding airspeed is 4.8h-1(g/(g catalyst. multidot.hr)), the reaction temperature was 200 ℃ and the reaction pressure was 4MPa, and the reaction results obtained after 2 hours of stabilization are shown in Table 2.
Example 11
6 g of the mixture is added into a fixed bed reactor with the inner diameter of 12mm
The catalyst of the strip molecular sieve is used for carrying out the conversion reaction of ethylene glycol monomethyl ether. The catalyst contains 70 wt% of MCM-56 molecular sieve (silicon-aluminum molecular ratio of 28) which is impregnated with 2 wt% of Ti and 30 wt% of alumina binder, and is treated by water vapor for 3 hours at 350 ℃. The reaction raw material is glycol monomethyl ether methanol solution (methanol and glycol monomethyl ether)The molar ratio of dimethyl ether is 0.5), and the feed space velocity is 5.8h-1(g/(g catalyst. h)), the catalyst performance was substantially unchanged by a total reaction time of 102 hours under conditions of a reaction temperature of 208 ℃ and a reaction pressure of 5MPa, and the reaction results are shown in Table 3.
Example 12
6 g of the mixture is added into a fixed bed reactor with the inner diameter of 12mm
The catalyst of the strip molecular sieve is used for carrying out the conversion reaction of ethylene glycol monomethyl ether. The catalyst contains 85 wt% of HMCM-22 molecular sieve (silicon-aluminium molecular ratio is 15) and 15 wt% of silicon dioxide binder, and is treated by water vapor at 500 ℃ for 3 hours. When the reaction raw material is ethylene glycol monomethyl ether aqueous solution (the molar ratio of water to ethylene glycol monomethyl ether is 4.7), the feeding airspeed is 4.8h-1(g/(g catalyst. h)), the reaction temperature was 197 ℃ and the reaction pressure was 5MPa, and the catalyst performance was substantially unchanged by a total reaction time of 78 hours, and the reaction results are shown in Table 4.
Example 13
6 g of the mixture is added into a fixed bed reactor with the inner diameter of 12mm
The catalyst of the strip molecular sieve is used for carrying out the conversion reaction of ethylene glycol monomethyl ether. The catalyst contains 70 wt% of HMCM-22 molecular sieve (silicon-aluminium molecular ratio is 50) and 30 wt% of alumina binder, and is treated by water vapor at 650 ℃ for 0.5 hour. When the reaction raw material is ethylene glycol monomethyl ether aqueous solution (the molar ratio of water to ethylene glycol monomethyl ether is 4.9), the feeding airspeed is 2.2h-1(g/(g catalyst. hr)), the reaction temperature was 205 ℃ and the reaction pressure was 3MPa, the catalyst performance was almost unchanged for 172 hours, and the reaction results are shown in Table 5.
Table 1 examples 1-6
Table 2 examples 7-10
Table 3 example 11
Table 4 example 12
Table 5 example 13
Claims (12)
1. The method for converting the ethylene glycol monomethyl ether is characterized by comprising the steps of contacting a material containing the ethylene glycol monomethyl ether and water with a molecular sieve catalyst and reacting, wherein the molecular sieve catalyst contains one or more of a ZSM-23 molecular sieve, an MCM-49 molecular sieve, an SAPO-11 molecular sieve and an MCM-22 molecular sieve with a silicon-aluminum molecular ratio of 15-50; in the material containing the ethylene glycol monomethyl ether and the water, the molar ratio of the water to the ethylene glycol monomethyl ether is 2.5-6.
2. The method of claim 1, wherein the molecular sieve is one of a ZSM-23 molecular sieve, an MCM-22 molecular sieve having a silica to alumina molecular ratio of 15 to 50.
3. The method of claim 1 or 2, wherein the cation in the molecular sieve is a hydrogen ion.
4. The method of claim 3, wherein the hydrogen ions in the molecular sieve are partially or fully substituted with one or more of Mg ions, Ca ions, La ions, and Cu ions.
5. The method of claim 1 or 2, wherein the molecular sieve is impregnated with one or more of P, Ti, Zr, and La prior to use.
6. The process of claim 1 or 2, wherein the molecular sieve catalyst comprises 50 to 95% molecular sieve and 5 to 50% binder, based on the dry weight of the molecular sieve catalyst.
7. The method of claim 6, wherein the binder comprises one or more of alumina, silica, and kaolin.
8. The method of claim 1 or 2, wherein the molecular sieve catalyst has been subjected to steam treatment at 350 to 650 ℃ prior to use.
9. The process according to claim 1 or 2, wherein ethylene glycol monomethyl ether is reacted in a liquid phase or a gas-liquid mixed state at a temperature of 140 to 240 ℃ and a pressure of 0.3 to 8.0 MPa.
10. The method as set forth in claim 9, wherein the reaction temperature is 160 ℃ and 220 ℃ and the reaction pressure is 1.5-4.0 MPa.
11. The process of claim 1 or 2, wherein the reaction is carried out in a fixed bed reactor, a tank reactor, or a catalytic distillation reactor.
12. The process of claim 1 wherein the feed comprising ethylene glycol monomethyl ether and water further comprises reaction products of a recycle reaction.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55104221A (en) * | 1979-02-02 | 1980-08-09 | Sanko Kagaku Kogyo Kk | Production of ethylene glycol ether |
| JP2012149033A (en) * | 2010-12-27 | 2012-08-09 | Nippon Nyukazai Kk | Method for producing (poly)alkylene glycol diether |
| CN104119228A (en) * | 2013-04-26 | 2014-10-29 | 中国科学院大连化学物理研究所 | Methyl methoxyacetate (MMAC) synthesis method |
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2016
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55104221A (en) * | 1979-02-02 | 1980-08-09 | Sanko Kagaku Kogyo Kk | Production of ethylene glycol ether |
| JP2012149033A (en) * | 2010-12-27 | 2012-08-09 | Nippon Nyukazai Kk | Method for producing (poly)alkylene glycol diether |
| CN104119228A (en) * | 2013-04-26 | 2014-10-29 | 中国科学院大连化学物理研究所 | Methyl methoxyacetate (MMAC) synthesis method |
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