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CN107915578B - Method for producing ethylene glycol by ethylene carbonate hydrolysis - Google Patents

Method for producing ethylene glycol by ethylene carbonate hydrolysis Download PDF

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CN107915578B
CN107915578B CN201610878299.XA CN201610878299A CN107915578B CN 107915578 B CN107915578 B CN 107915578B CN 201610878299 A CN201610878299 A CN 201610878299A CN 107915578 B CN107915578 B CN 107915578B
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ethylene carbonate
silica
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alumina gel
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CN107915578A (en
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陈梁锋
何文军
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China Petroleum and Chemical Corp
Sinopec Shanghai Research Institute of Petrochemical Technology
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Sinopec Shanghai Research Institute of Petrochemical Technology
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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
    • C07C29/12—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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/20—Vanadium, niobium or tantalum
    • 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
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • 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

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention relates to a method for producing 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 catalyst comprises the following components in parts by weight: a) 1-50 parts of niobium pentoxide; and b) 50-99 parts of silica-alumina gel carrier SiO2‑Al2O3(ii) a Al in the silica-alumina gel carrier2O35-50 parts of SiO2The technical scheme of 50-95 parts by weight better solves the problem and can be used in the industrial production of preparing ethylene glycol by hydrolyzing ethylene carbonate.

Description

Method for producing ethylene glycol by ethylene carbonate hydrolysis
Technical Field
The invention relates to a method for producing 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 water ratio of the direct catalytic hydration method is relatively low (About 5 or so), but still requires evaporation to remove a large amount of water, whereas the EC route first utilizes 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 producing 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 producing ethylene glycol by hydrolyzing ethylene carbonate comprises the steps of contacting ethylene carbonate and water with a catalyst under reaction conditions; the catalyst comprises the following components in parts by weight: a) 1-50 parts of niobium pentoxide; and b) 50-99 parts of silica-alumina gel carrier SiO2-Al2O3(ii) a Al in the silica-alumina gel carrier2O35-50 parts of SiO2The weight part of the composition is 50-95 parts.
In the above technical solution, the content of niobium pentoxide is preferably 2-40 parts, more preferably 5 &30 parts of (1); silica alumina gel carrier SiO2-Al2O3The content of (b) is preferably 60 to 98 parts, more preferably 70 to 95 parts.
In the above technical scheme, Al in the silica-alumina gel carrier2O3The weight part of (b) is preferably 5 to 40 parts, and more preferably 10 to 30 parts; SiO 22The weight part of (b) is preferably 60 to 95 parts, more preferably 70 to 90 parts.
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 preparation method of the catalyst comprises the following steps: the niobic acid was dissolved in an aqueous solution of oxalic acid to obtain a dipping solution. Mixing silica alumina gel SiO2-Al2O3Adding the mixture into the impregnation liquid, and drying and roasting the obtained mixture to obtain the silica-alumina gel supported niobium pentoxide catalyst. 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 silica-alumina gel can adopt a commercial product and can also be synthesized by the following method: 1) aluminum nitrate (Al (NO) was added at room temperature3)3·9H2O) is dissolved in alkanol, stirred for 20min and dissolved to obtain a solution A; 2) dissolving Tetraethoxysilane (TEOS) in alkanol at room temperature, adding water and nitric acid, and stirring for 20min to prehydrolyze tetraethoxysilane to obtain a mixture B; 3) and pouring the solution A into the mixture B, stirring at room temperature for a period of time, and then dropwise adding concentrated ammonia water until the pH value is 8. And aging the obtained mixture at a certain temperature for a period of time, filtering, washing for a plurality of times by using alkanol, and drying at 120 ℃ to obtain the silica-alumina gel SA. The alkanol used in step 1) and step 2) may be at least one of methanol, ethanol, n-propanol, isopropanol, butanol, isobutanol and tert-butanol; the stirring time of the A, B mixture in the step 3) is0.5-2 hours, the aging temperature is 40-90 ℃, and the aging time is 6-24 hours.
The carrier used by the invention is silica alumina gel SiO2-Al2O3Compared with ion exchange resin, the heat resistance is greatly improved; the used active component niobium pentoxide has stable property and proper acidity, and solves the problems of poor catalyst stability and easy loss of the active component in the prior art. By adopting the method, at the reaction temperature of 100 ℃, 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 98.5 percent, the selectivity of the ethylene glycol is 99.4 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 silica alumina gel SA 1: dissolving 22.1g of aluminum nitrate in 200ml of absolute ethyl alcohol at room temperature, and stirring for 20min to dissolve the aluminum nitrate to obtain a solution A1; dissolving 58.9g of tetraethoxysilane in 200ml of absolute ethyl alcohol, adding 200ml of deionized water and 5ml of concentrated nitric acid, and stirring for 20min to obtain a prehydrolysis mixture B1; the solution A1 was poured into the mixture B1 and after stirring at room temperature for 1 hour, concentrated aqueous ammonia was added dropwise until the pH was 8. Then standing and aging at 60 deg.C for 12h, filtering, washing precipitate with anhydrous ethanol for 3 times, and oven standing overnight at 120 deg.C to obtain silica-alumina gel SA1, and measuring by ICP-AES to obtain Al2O3The mass percentage of (B) is 14.9%.
[ example 2 ]
Preparation of silica alumina gel SA 2: dissolving 7.3g of aluminum nitrate in 200ml of anhydrous methanol at room temperature, and stirring for 20min to dissolve the aluminum nitrate to obtain a solution A2; dissolving 65.9g of tetraethoxysilane in 200ml of anhydrous methanol, adding 200ml of deionized water and 5ml of concentrated nitric acid, and stirring for 20min to obtain a prehydrolysis mixture B2; the solution A2 was poured into the mixture B2 and after stirring at room temperature for 1 hour, concentrated aqueous ammonia was added dropwise until the pH was 8. Then standing at 80 deg.C for aging for 20 hr, filtering, washing with anhydrous methanolPrecipitating for 3 times, oven standing at 120 deg.C overnight to obtain silica-alumina gel SA2, and measuring Al by ICP-AES2O3The mass percentage of (B) is 5.1%.
[ example 3 ]
Preparation of silica alumina gel SA 3: the preparation procedure was identical to [ example 1 ] except that 36.8g and 52.0g of aluminum nitrate and 52.0g of ethyl orthosilicate, respectively, were used to obtain a silica-alumina gel SA3, Al measured by ICP-AES2O3The mass percentage of (B) is 24.8%.
[ example 4 ]
Preparation of silica alumina gel SA 4: the preparation procedure was identical to [ example 1 ] except that 51.5g and 45.1g of aluminum nitrate and ethyl orthosilicate, respectively, were used to give a silica-alumina gel SA4, Al determined by ICP-AES2O3The mass percentage of (B) is 35.3%.
[ example 5 ]
Preparation of silica alumina gel SA 5: the preparation procedure was identical to [ example 1 ] except that 66.2g and 33.1g of aluminum nitrate and ethyl orthosilicate, respectively, were used to give a silica-alumina gel SA5, Al determined by ICP-AES2O3The mass percentage of (B) is 44.6%.
[ example 6 ]
Weighing 2.67g of niobic acid, dissolving the niobic acid in 50ml of oxalic acid solution with the concentration of 1.8mol/L, adding 10g of silica-alumina gel SA1, drying the obtained mixture at 120 ℃ overnight, and then roasting the dried mixture at 500 ℃ for 2 hours to obtain a silica-alumina gel-loaded niobium pentoxide catalyst Cat-1, wherein the weight parts of niobium pentoxide is 20.0 parts, and the weight parts of silica-alumina gel SA1 is 80.0 parts.
[ example 7 ]
The catalyst preparation method was the same as [ example 6 ] except that the mass of the niobic acid used was 0.56g, to give a silica-alumina gel-supported niobium pentoxide catalyst Cat-2, wherein the weight parts of niobium pentoxide were 5.1 parts, and the weight parts of silica-alumina gel SA1 were 94.9 parts.
[ example 8 ]
The catalyst preparation method was the same as [ example 6 ] except that the mass of the niobic acid used was 1.19g, to give a silica-alumina gel-supported niobium pentoxide catalyst Cat-3, in which the weight part of niobium pentoxide was 10.0 parts, and the weight part of silica-alumina gel SA1 was 90.0 parts.
[ example 9 ]
The catalyst preparation method was the same as [ example 6 ] except that the mass of the niobic acid used was 0.22g, to give a silica-alumina gel-supported niobium pentoxide catalyst Cat-4, in which the weight part of niobium pentoxide was 2.1 parts and the weight part of silica-alumina gel SA1 was 97.9 parts.
[ example 10 ]
The catalyst preparation method was the same as [ example 6 ] except that the mass of the niobic acid used was 4.58g, to give a silica-alumina gel-supported niobium pentoxide catalyst Cat-5, in which the weight parts of niobium pentoxide were 31.0 parts, and the weight parts of silica-alumina gel SA1 were 69.0 parts.
[ example 11 ]
The catalyst preparation method was the same as [ example 6 ] except that the mass of the niobic acid used was 7.12g, to give a silica-alumina gel-supported niobium pentoxide catalyst Cat-6, in which the weight part of niobium pentoxide was 39.0 parts and the weight part of silica-alumina gel SA1 was 61.0 parts.
[ example 12 ]
The preparation method of the catalyst is the same as that of example 6, except that the carrier used is SA2, and the niobium pentoxide catalyst Cat-7 loaded by silica alumina gel is obtained.
[ example 13 ]
The preparation method of the catalyst is the same as that of example 6, except that the carrier used is SA3, and the niobium pentoxide catalyst Cat-8 loaded by silica-alumina gel is obtained.
[ example 14 ]
The preparation method of the catalyst is the same as that of example 6, except that the carrier used is SA4, and the niobium pentoxide catalyst Cat-9 loaded by silica alumina gel is obtained.
[ example 15 ]
The preparation method of the catalyst is the same as that of example 6, except that the carrier used is SA5, and the niobium pentoxide catalyst Cat-10 loaded by silica-alumina gel is obtained.
[ example 16 ]
The catalyst Cat-1 prepared in example 6 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 Cat-1 were placed in a 100 ml autoclave (molar ratio of water to ethylene carbonate: 1, mass ratio of catalyst to ethylene carbonate: 0.05: 1) and reacted at 100 ℃ 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 the ethylene carbonate with the conversion rate of 98.5%, the selectivity of the ethylene glycol of 99.4% and the balance of the polyethylene glycol.
[ examples 17 to 25 ]
The catalysts Cat-2 to Cat-10 prepared in examples 7 to 15 were used in the reaction for preparing ethylene glycol by hydrolyzing ethylene carbonate, the reaction conditions were the same as in example 16, and the obtained reaction results are shown in Table 1.
TABLE 1
Figure BDA0001126120850000061
[ example 26 ]
The same as [ example 16 ] except that the reaction temperature was 120 ℃. The conversion rate of the ethylene carbonate obtained was 99.2%, the selectivity of ethylene glycol was 99.2%, and the selectivity of polyethylene glycol was 0.8%.
[ example 27 ]
The same as [ example 16 ] except that the reaction temperature was 140 ℃. The conversion of ethylene carbonate obtained was 99.5%, the selectivity for ethylene glycol was 98.2% and the selectivity for polyethylene glycol was 1.8%.
[ example 28 ]
The same as [ example 16 ] except that the reaction temperature was 80 ℃. The conversion of ethylene carbonate obtained was 53.6%, the selectivity to ethylene glycol was 99.2% and the selectivity to polyethylene glycol was 0.8%.
[ example 29 ]
The same as in example 16 except that the mass of the deionized water was 27.0 g (molar ratio of water to ethylene carbonate was 3: 1). The conversion rate of the obtained ethylene carbonate is 99.5%, the selectivity of the ethylene glycol is 99.2%, and the selectivity of the polyethylene glycol is 0.8%.
[ example 30 ]
The same as in example 16 except that the mass of the deionized water was 72.0 g (molar ratio of water to ethylene carbonate was 8: 1). The conversion rate of the obtained ethylene carbonate is 99.6%, the selectivity of the ethylene glycol is 99.1%, and the selectivity of the polyethylene glycol is 0.9%.
[ example 31 ]
The same as in example 16 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 69.8%, the selectivity of the ethylene glycol is 99.3%, and the selectivity of the polyethylene glycol is 0.7%.
[ example 32 ]
The same as in example 16 except that the amount of catalyst was 8.8 g (the ratio of catalyst to ethylene carbonate was 0.2: 1). The conversion rate of the obtained ethylene carbonate is 99.7%, the selectivity of the ethylene glycol is 98.8%, and the selectivity of the polyethylene glycol is 1.2%.
[ example 33 ]
The same as in example 16 except that the mass of the catalyst was 17.6 g (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 97.5%, and the selectivity of the polyethylene glycol is 2.5%.
[ example 34 ]
The catalyst after the reaction was separated and used for 5 times under the same reaction conditions as in example 16, and the activity was not significantly decreased. The reaction results are shown in Table 2.
TABLE 2
Figure BDA0001126120850000081

Claims (9)

1. A method for producing ethylene glycol by hydrolyzing ethylene carbonate comprises the steps of contacting ethylene carbonate and water with a catalyst under reaction conditions; the catalyst comprises the following components in parts by weight: a) 5 to 50 parts ofNiobium pentoxide of (4); and b) 50-95 parts of silica-alumina gel carrier SiO2-Al2O3(ii) a Al in the silica-alumina gel carrier2O35-50 parts of SiO250-95 parts by weight;
wherein the reaction temperature is 80-160 ℃.
2. The method for producing ethylene glycol by hydrolyzing ethylene carbonate according to claim 1, wherein the content of niobium pentoxide is 5-40 parts, and the silica alumina gel carrier SiO is2-Al2O3The content of (B) is 60-95 parts.
3. The method for producing ethylene glycol by hydrolyzing ethylene carbonate according to claim 2, wherein the content of niobium pentoxide is 5-30 parts, and the silica alumina gel carrier SiO is2-Al2O3The content of (B) is 70-95 parts.
4. The method for producing ethylene glycol by hydrolyzing ethylene carbonate according to claim 2, wherein the content of niobium pentoxide is 20 to 30 parts.
5. The method for producing ethylene glycol by hydrolyzing ethylene carbonate according to claim 1, wherein Al in the silica-alumina gel carrier2O35-40 parts of SiO2The weight portion of the composition is 60-95 parts.
6. The method for producing ethylene glycol by hydrolyzing ethylene carbonate according to claim 5, wherein Al in the silica-alumina gel carrier2O310-30 parts of SiO2The weight portion of the composition is 70-90 parts.
7. The method for producing ethylene glycol by hydrolyzing ethylene carbonate according to claim 1, wherein the reaction temperature is 80-160 ℃, the molar ratio of water to ethylene carbonate is (1-10): 1, and the weight ratio of the catalyst to ethylene carbonate is (0.005-1): 1.
8. The method for producing ethylene glycol by hydrolyzing ethylene carbonate according to claim 7, wherein the molar ratio of water to ethylene carbonate is (1-8): 1, and the weight ratio of the catalyst to ethylene carbonate is (0.01-0.5): 1.
9. The method for producing ethylene glycol by hydrolyzing the ethylene carbonate according to claim 8, wherein the reaction temperature is 100-140 ℃, the molar ratio of 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.
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