CN107915577B - Method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate - Google Patents
Method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate Download PDFInfo
- Publication number
- CN107915577B CN107915577B CN201610878296.6A CN201610878296A CN107915577B CN 107915577 B CN107915577 B CN 107915577B CN 201610878296 A CN201610878296 A CN 201610878296A CN 107915577 B CN107915577 B CN 107915577B
- Authority
- CN
- China
- Prior art keywords
- ethylene carbonate
- catalyst
- apo
- hydrolyzing
- ethylene
- 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.)
- Active
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 96
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 30
- 230000003301 hydrolyzing effect Effects 0.000 title claims abstract description 14
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- -1 phosphorus-aluminum-oxygen Chemical group 0.000 claims abstract description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052593 corundum Inorganic materials 0.000 claims description 8
- 229910001845 yogo sapphire Inorganic materials 0.000 claims description 8
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 229910001392 phosphorus oxide Inorganic materials 0.000 claims description 2
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 claims description 2
- UHAQRCJYQAKQEE-UHFFFAOYSA-M [O-2].[OH-].O.[Al+3].P Chemical compound [O-2].[OH-].O.[Al+3].P UHAQRCJYQAKQEE-UHFFFAOYSA-M 0.000 claims 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 description 9
- 229920001223 polyethylene glycol Polymers 0.000 description 9
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 7
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 7
- 235000019838 diammonium phosphate Nutrition 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000036571 hydration Effects 0.000 description 7
- 238000006703 hydration reaction Methods 0.000 description 7
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 101000611023 Homo sapiens Tumor necrosis factor receptor superfamily member 6 Proteins 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 102100040403 Tumor necrosis factor receptor superfamily member 6 Human genes 0.000 description 3
- 150000005676 cyclic carbonates Chemical class 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000005696 Diammonium phosphate Substances 0.000 description 2
- 101000679903 Homo sapiens Tumor necrosis factor receptor superfamily member 25 Proteins 0.000 description 2
- 102100022203 Tumor necrosis factor receptor superfamily member 25 Human genes 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- SJVIFVURCJFNAV-UHFFFAOYSA-M P(=O)([O-])(O)O.[O-2].[Al+3] Chemical compound P(=O)([O-])(O)O.[O-2].[Al+3] SJVIFVURCJFNAV-UHFFFAOYSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
Classifications
-
- 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
- C07C29/12—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 esters of mineral acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/82—Phosphates
- B01J29/83—Aluminophosphates [APO compounds]
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate, which mainly solves the problems of poor catalyst stability and easy loss of active components in the prior art. The invention adopts the steps of contacting ethylene carbonate and water with a catalyst under reaction conditions; the technical scheme that the catalyst is a phosphorus-aluminum-oxygen catalyst APO better solves the problem, and can be used in the industrial production of ethylene glycol prepared by hydrolyzing ethylene carbonate.
Description
Technical Field
The invention relates to a method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate.
Background
Hydrolysis of esters is an important chemical reaction and is widely applied to various fields of petrochemical production, wherein hydrolysis of cyclic carbonates such as Ethylene Carbonate (EC), propylene carbonate and the like is a very important basic position.
Hydrolysis of EC is an important step in the production of Ethylene Glycol (EG) from Ethylene Oxide (EO) catalytic hydration in a two-step process. EG is an important organic chemical raw material and is mainly used for producing polyester fibers, antifreezing agents, unsaturated polyester resins, nonionic surfactants, ethanolamine, explosives and the like. The production technology of EG is mainly divided into petrochemical route and non-petrochemical route. In the petrochemical route, an EO direct hydration method and an EO catalytic hydration method exist, the direct hydration method can ensure higher EG yield only by requiring higher water ratio (more than 20), and the energy consumption in the process of EG purification is higher. EO catalyzed hydration processes in turn include direct catalyzed hydration processes and EC routes. The direct catalytic hydration process has a relatively low water ratio (around 5), but still requires evaporation to remove a large amount of water, whereas the EC route first utilizes the CO emitted from ethylene oxidation to make EO2EC is generated by raw materials and EO under the action of a catalyst, then EG is generated by catalytic hydrolysis by taking EC as an intermediate product, the water ratio in the process is close to the stoichiometric ratio of 1, and the method is the industrialization direction of preparing EG from EO in the future.
The catalysts currently used for the hydrolysis of cyclic carbonates are mainly: alkali (earth) metal (bi) carbonates (US4524224, 1985), compounds of Mo and W (JP822106631, 1982; WO2009071651, 2009), quaternary ammonium salts and ion exchange resins (EP0133763, 1989; US6080897, 2000; US20090156867, 2009) and the like. However, these catalytic systems have problems of difficulty in separating the catalyst, low activity, low stability, and the like.
The strong alkali type ion exchange resin has good activity and selectivity when used for cyclic carbonate hydrolysis, but due to poor temperature resistance and swelling resistance, the activity is reduced rapidly in the catalytic reaction process (Yu FP, Cai H, He WJ, et al.J.appl.Polym.Sci.,2010,115: 2946-2954), which is the main reason for the failure of the catalyst to be industrialized.
Disclosure of Invention
The invention aims to solve the technical problems of poor catalyst stability and easy loss of active components in the prior art, and provides a novel method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate. The method has the characteristics of high catalyst activity and selectivity and low loss of active components.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows: a method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate comprises the steps of contacting ethylene carbonate and water with a catalyst under reaction conditions; the catalyst is a phosphorus-aluminum-oxygen catalyst APO.
In the technical scheme, the weight content of Al in the phosphorus-aluminum-oxygen APO is Al2O310-80%, preferably 20-60%, more preferably 30-50%; the content of P is as P2O5In an amount of 20 to 90%, preferably 40 to 80%, more preferably 50 to 70%.
In the technical scheme, the reaction temperature is 60-200 ℃, preferably 80-160 ℃, and more preferably 100-140 ℃.
In the technical scheme, the molar ratio of the water to the ethylene carbonate is (1-10): 1, preferably (1-8): 1, and more preferably (1-6): 1.
In the technical scheme, the weight ratio of the catalyst to the ethylene carbonate is (0.005-1): 1, preferably (0.01-0.5): 1, and more preferably (0.02-0.2): 1.
The aluminum-phosphorus oxide in the invention is a mixed oxide of aluminum oxide and phosphorus oxide. The preparation method is well known in the art and can be prepared by the following method: 1) aluminum nitrate (Al (NO) was added at room temperature3)3·9H2O) and diammonium hydrogen phosphate are dissolved in water, and then concentrated nitric acid is added to acidify the solution to obtain a solution A; 2) adding concentrated ammonia water into the solution A at room temperature to adjust the pH value to 8, filtering the formed precipitate, washing, drying and roasting to obtain the productAluminophospho APO. The drying temperature is 100-150 ℃, and the drying time is 5-24 hours. The roasting temperature is 550-650 ℃, and the roasting time is 1-24 hours. The adding amount of the concentrated nitric acid is 5-20% of the weight of the aluminum nitrate.
The catalyst used in the invention is phosphorus-aluminum-oxygen, compared with ion exchange resin, the catalyst has stable property and greatly improved heat resistance, and solves the problems of poor catalyst stability and easy loss of active components in the prior art. By adopting the method, at the reaction temperature of 120 ℃, the molar ratio of water to ethylene carbonate is 1.5:1, and the weight ratio of the catalyst to the ethylene carbonate is 0.05: under the condition of 1, the conversion rate of the ethylene carbonate is 97.2 percent, the selectivity of the ethylene glycol is 99.6 percent, and after the catalyst is repeatedly used for 5 times, the activity is reduced by less than 5 percent, thereby obtaining better technical effect.
The invention is further illustrated by the following examples.
Detailed Description
[ example 1 ]
Preparation of aluminophosphateoxy APO: dissolving 58.8g of aluminum nitrate and 22.3g of diammonium hydrogen phosphate in 500ml of deionized water at room temperature, stirring for 1h, adding 10ml of concentrated nitric acid for acidification, continuously dropwise adding concentrated ammonia water to adjust the pH value to 8, filtering the formed precipitate, washing with deionized water for 3 times, drying at 120 ℃ overnight, drying and roasting at 500 ℃ to obtain aluminum oxide phosphate APO-1, and determining the weight content of Al in the APO-1 by ICP-AES (inductively coupled plasma-atomic emission spectrometry)2O340% by weight of P, the content of P being expressed as P2O5The amount was 60%.
[ example 2 ]
The procedure for the preparation of aluminophosphate APO was the same as in example 1, except that 14.7g and 33.5g of aluminum nitrate and 33.5g of diammonium phosphate were used, respectively, to obtain aluminophosphate APO-2, and the weight content of Al in APO-2 was determined by ICP-AES as Al2O3Calculated as 10%, the weight content of P is calculated as P2O5The calculated value is 90%.
[ example 3 ]
The procedure for the preparation of Aluminoaluminophosphate APO was the same as in example 1, except that 36.8g of aluminum nitrate and 36.8g of diammonium phosphate were used27.9g of aluminumoxy APO-3, and the weight content of Al in the APO-3 was determined by ICP-AES as Al2O3Calculated as 25%, the weight content of P is calculated as P2O5The content was found to be 75%.
[ example 4 ]
The procedure for the preparation of aluminophosphate APO was the same as in example 1, except that 73.5g and 18.6g of aluminum nitrate and 18.6g of diammonium hydrogen phosphate were used, respectively, to obtain aluminophosphate APO-4, and the weight content of Al in APO-4 was determined by ICP-AES as Al2O3Calculated as 50%, the weight content of P is calculated as P2O5Calculated as 50%.
[ example 5 ]
The procedure for the preparation of aluminophosphate APO was the same as in example 1, except that 95.6g and 13.0g of aluminum nitrate and 13.0g of diammonium hydrogen phosphate were used, respectively, to obtain aluminophosphate APO-5, and the weight content of Al in APO-5 was determined by ICP-AES as Al2O3Calculated as 65%, the weight content of P is calculated as P2O5The weight is 35%.
[ example 6 ]
The procedure for the preparation of aluminophosphate APO was the same as in example 1, except that 117.6g and 7.4g of aluminum nitrate and diammonium hydrogen phosphate were used, respectively, to obtain aluminophosphate APO-6, and the weight content of Al in APO-6 was determined by ICP-AES as Al2O3Calculated as 80%, the weight content of P is calculated as P2O5Calculated as 20%.
[ example 7 ]
The catalyst APO-1 prepared in example 1 was used in the reaction for preparing ethylene glycol by hydrolyzing ethylene carbonate. 44.0 g of ethylene carbonate, 13.5 g of deionized water and 2.2 g of NAPO-1 were placed in a 100 ml autoclave (molar ratio of water to ethylene carbonate: 1, weight ratio of catalyst to ethylene carbonate: 0.05: 1) and reacted at 120 ℃ for 2 hours. After the reaction was complete, the autoclave was cooled to room temperature and vented. And (3) performing gas chromatography analysis on the liquid-phase product to obtain that the conversion rate of the ethylene carbonate is 97.2%, the selectivity of the ethylene glycol is 99.6%, and the balance is the polyethylene glycol.
[ examples 8 to 12 ]
The catalysts APO-2 to APO-6 prepared in the examples 2 to 6 are used in the reaction for preparing ethylene glycol by hydrolyzing ethylene carbonate, the reaction conditions are the same as those in the example 7, and the obtained reaction results are shown in Table 1.
TABLE 1
[ example 13 ]
The same as [ example 7 ] except that the reaction temperature was 140 ℃. The conversion of ethylene carbonate obtained was 99.1%, the selectivity for ethylene glycol was 98.5%, and the selectivity for polyethylene glycol was 1.5%.
[ example 14 ]
The same as [ example 7 ] except that the reaction temperature was 160 ℃. The conversion of ethylene carbonate obtained was 99.5%, the selectivity for ethylene glycol was 97.0%, and the selectivity for polyethylene glycol was 3.0%.
[ example 15 ]
The same as [ example 7 ] except that the reaction temperature was 100 ℃. The conversion of ethylene carbonate obtained was 61.3%, the selectivity for ethylene glycol was 99.4% and the selectivity for polyethylene glycol was 0.6%.
[ example 16 ]
The same as in example 7 except that the mass of deionized water was 27.0 grams (molar ratio of water to ethylene carbonate was 3: 1). The conversion rate of the obtained ethylene carbonate is 98.6%, the selectivity of the ethylene glycol is 99.4%, and the selectivity of the polyethylene glycol is 0.6%.
[ example 17 ]
The same as in example 7 except that the mass of deionized water was 72.0 grams (water to ethylene carbonate molar ratio was 8: 1). The conversion rate of the obtained ethylene carbonate is 99.8%, the selectivity of the ethylene glycol is 99.5%, and the selectivity of the polyethylene glycol is 0.5%.
[ example 18 ]
The same as in example 7 except that the amount of catalyst used was 1.1 g (the ratio of catalyst to ethylene carbonate was 0.025: 1). The conversion rate of the obtained ethylene carbonate is 71.6%, the selectivity of the ethylene glycol is 99.1%, and the selectivity of the polyethylene glycol is 0.9%.
[ example 19 ]
The same as in example 7 except that the amount of catalyst was 8.8g (the ratio of catalyst to ethylene carbonate was 0.2: 1). The conversion rate of the obtained ethylene carbonate is 99.9%, the selectivity of the ethylene glycol is 97.9%, and the selectivity of the polyethylene glycol is 2.1%.
[ example 20 ]
The same as in example 7 except that the mass of the catalyst was 17.6g (the mass ratio of the catalyst to the ethylene carbonate was 0.4: 1). The conversion rate of the obtained ethylene carbonate is 99.9%, the selectivity of the ethylene glycol is 96.3%, and the selectivity of the polyethylene glycol is 3.7%.
[ example 21 ]
The catalyst after the reaction was isolated and used for 5 times under the same reaction conditions as in example 18, without significant decrease in activity. The reaction results are shown in Table 2.
TABLE 2
Claims (5)
1. A method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate comprises the steps of contacting ethylene carbonate and water with a catalyst under reaction conditions; the catalyst is a phosphorus-aluminum-oxygen catalyst APO, and the weight content of Al in the phosphorus-aluminum-oxygen APO is Al2O3Calculated as 20-60%, the content of P is calculated as P2O540-80% of the total; the phosphorus aluminum oxygen APO is a mixed oxide of aluminum oxide and phosphorus oxide;
wherein the reaction temperature is 80-160 ℃.
2. The method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate according to claim 1, wherein the weight content of Al in the phosphorus aluminum oxide (APO) is Al2O330-50% of P, and the content of P is P2O5Calculated as 50-70%.
3. The method for synthesizing the ethylene glycol by hydrolyzing the ethylene carbonate according to claim 1, wherein the molar ratio of the water to the ethylene carbonate is (1-10): 1, and the weight ratio of the catalyst to the ethylene carbonate is (0.005-1): 1.
4. The method for synthesizing the ethylene glycol by hydrolyzing the ethylene carbonate according to claim 3, wherein the molar ratio of the water to the ethylene carbonate is (1-8): 1, and the weight ratio of the catalyst to the ethylene carbonate is (0.01-0.5): 1.
5. The method for synthesizing the ethylene glycol by hydrolyzing the ethylene carbonate according to claim 4, wherein the reaction temperature is 100-140 ℃, the molar ratio of the water to the ethylene carbonate is (1-6): 1, and the weight ratio of the catalyst to the ethylene carbonate is (0.02-0.2): 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610878296.6A CN107915577B (en) | 2016-10-08 | 2016-10-08 | Method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610878296.6A CN107915577B (en) | 2016-10-08 | 2016-10-08 | Method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107915577A CN107915577A (en) | 2018-04-17 |
| CN107915577B true CN107915577B (en) | 2020-12-29 |
Family
ID=61892159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610878296.6A Active CN107915577B (en) | 2016-10-08 | 2016-10-08 | Method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107915577B (en) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4400559A (en) * | 1982-06-14 | 1983-08-23 | The Halcon Sd Group, Inc. | Process for preparing ethylene glycol |
| CN1212192C (en) * | 2000-03-31 | 2005-07-27 | 意大利博雷加德有限公司 | Phosphorous-aluminium-mixed oxide catalyst, process for its preparation and use thereof |
| TW200503997A (en) * | 2002-12-20 | 2005-02-01 | Shell Int Research | Process for the preparation of alkylene glycol |
| CN100406419C (en) * | 2006-05-26 | 2008-07-30 | 华东理工大学 | Method for preparing dibasic alcohol |
| CN101121642A (en) * | 2006-08-10 | 2008-02-13 | 中国科学院过程工程研究所 | Catalytic method used for cyclic carbonates hydrolysis |
| CN102491876A (en) * | 2011-11-11 | 2012-06-13 | 中国科学院过程工程研究所 | Method for preparing vicinal diol by solid base catalyst |
-
2016
- 2016-10-08 CN CN201610878296.6A patent/CN107915577B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN107915577A (en) | 2018-04-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101768142B (en) | Method for catalysis-synthesizing 2,5-dicarbaldehyde by carbohydrate | |
| CN102786499B (en) | Method for preparing cyclohexene oxide | |
| EP4238957A1 (en) | System for manufacturing phthalonitrile-based compound and method for manufacturing phthalonitrile-based compound using same | |
| CN107915576B (en) | Method for producing ethylene glycol by ethylene carbonate hydrolysis | |
| CN107915577B (en) | Method for synthesizing ethylene glycol by hydrolyzing ethylene carbonate | |
| CN109438506B (en) | Method for preparing tris (1, 3-dichloropropyl) phosphate | |
| CN102146032A (en) | Method for preparing methyl methacrylate | |
| CN107915573B (en) | Method for synthesizing dimethyl carbonate | |
| CN103623848A (en) | Preparation method of mesoporous mixed metal oxide catalyst | |
| CN102786500B (en) | Preparation method of cyclohexene oxide | |
| KR20120114088A (en) | Synthesis of glycerol carbonate using high active catalysts | |
| CN112645840B (en) | Method for preparing salicylamide by salicylamide continuous method | |
| CN107915578B (en) | Method for producing ethylene glycol by ethylene carbonate hydrolysis | |
| CN111349008B (en) | Method for preparing glyoxylic acid | |
| CN111018823B (en) | Process for preparing epsilon-caprolactone and co-producing methacrylic acid by cyclohexanone | |
| CN109305898B (en) | Method for preparing acrolein by glycerol dehydration | |
| CN112851554A (en) | Preparation method of guanidine nitrate | |
| CN107915635B (en) | Method for preparing dimethyl carbonate | |
| CN111410636A (en) | Preparation process of pyrazinamide | |
| CN114031493B (en) | Method for preparing high-purity glycolic acid by selective oxidation of ethylene glycol | |
| CN109304190B (en) | Catalyst for preparing acrolein from glycerol | |
| CN107915713B (en) | Method for producing ethylene carbonate | |
| CN102786501B (en) | Method for preparing cyclohexene oxide by heterogeneous catalytic epoxidation | |
| CN107915712B (en) | Method for preparing ethylene carbonate | |
| CN102228833B (en) | Cobalt-containing porous material and application thereof in preparation of phenol through benzene hydroxylation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |