CN110882697B - Catalyst for preparing ethylamine by ethanol amination and preparation method and application thereof - Google Patents
Catalyst for preparing ethylamine by ethanol amination and preparation method and application thereof Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 34
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000005576 amination reaction Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000005470 impregnation Methods 0.000 claims abstract description 16
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 11
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 11
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 9
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims abstract description 7
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims abstract description 5
- 229930064664 L-arginine Natural products 0.000 claims abstract description 5
- 235000014852 L-arginine Nutrition 0.000 claims abstract description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 22
- 229910017052 cobalt Inorganic materials 0.000 claims description 21
- 239000010941 cobalt Substances 0.000 claims description 21
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 21
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 6
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 claims description 6
- 229910001981 cobalt nitrate Inorganic materials 0.000 claims description 6
- 229910017604 nitric acid Inorganic materials 0.000 claims description 6
- 235000006408 oxalic acid Nutrition 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 230000032683 aging Effects 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 238000009489 vacuum treatment Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 7
- 239000006185 dispersion Substances 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- 238000012423 maintenance Methods 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005913 hydroamination reaction Methods 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000010512 small scale reaction Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/75—Cobalt
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/391—Physical properties of the active metal ingredient
- B01J35/394—Metal dispersion value, e.g. percentage or fraction
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0203—Impregnation the impregnation liquid containing organic compounds
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0207—Pretreatment of the support
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
Abstract
The invention provides a catalyst for preparing ethylamine by ethanol amination, a preparation method and application thereof. During the impregnation process, L-arginine, Cetyl Trimethyl Ammonium Bromide (CTAB), polyvinylpyrrolidone (PVP) and the like are added to promote the dispersion of the metal. The catalyst of the invention overcomes the problems of low-temperature activity, poor stability, more side reactions in high-temperature reaction and the like of the existing industrial catalyst, and realizes the maintenance of high activity and stability of the catalyst under the reaction condition of 140 ℃, thereby realizing high selectivity of ethylamine.
Description
Technical Field
The invention relates to a catalyst for preparing ethylamine by hydroamination of ethanol, a preparation method and application thereof.
Background
Ethylamine is a derivative generated by substituting hydrogen atoms of ammonia molecules by ethyl, mainly comprises monoethylamine, diethylamine, triethylamine and the like, is an important fine chemical intermediate, can react with various compounds to form the derivative, and is widely used in the industries of medicines, pesticides, rubber auxiliaries, metal ore dressing and the like.
US2363721 provides a nickel alumina catalyst, but less active in ethanol amination.
Chinese patent CN02104202.0 provides a low-grade aliphatic amine catalyst, which comprises active components such as cobalt and calcium loaded on a carrier, wherein the active components account for 10-50% of the weight of the catalyst, and the catalyst has complex preparation process, low ethanol conversion rate and unsatisfactory selectivity.
Chinese patent CN101869836A provides a low-grade aliphatic amine catalyst, a preparation method and an application thereof, the catalyst takes alumina as a carrier, and active components comprise: (1) 10-50% of Co; (2) 0.01 to 5 percent of at least one of Ce, Nd, Pr and Gd; (3) 0.01-10% of at least one of Cr, Mo, Ba, Ag, Mn, Ti, Ge and Zr. The catalyst shows better ethanol amination performance at higher reaction temperature (170 ℃), but the low-temperature activity and stability are to be improved, and the selectivity of ethylamine is not favorable.
Disclosure of Invention
The invention aims to provide a novel catalyst for synthesizing ethanol and preparing ethylamine by hydroamination, a preparation method and application thereof.
The invention provides a catalyst for preparing ethylamine by ethanol amination, which takes cobalt as a main active component and modified alumina as a carrier, and adopts a conventional impregnation method to prepare a cobalt/alumina catalyst; the cobalt content is 10-35% by weight of the catalyst, preferably 15-30%. The modified alumina carrier is obtained by modifying silicon oxide and one or more of oxalic acid, nitric acid, sulfuric acid and hydrochloric acid.
The impregnation method is to add a surfactant in the process of impregnating cobalt nitrate. The surfactant is one or more of L-arginine, cetyl trimethyl ammonium bromide and polyvinylpyrrolidone.
The invention provides a preparation method of the catalyst, which comprises the following specific steps:
(1) treating the formed alumina carrier containing 0.1-5.0 wt% of silicon oxide by using 1-5 wt% of acid solution at 80 ℃, washing for 1-2 times, drying at 120 ℃, and roasting at 400-800 ℃ for 3-5 hours to obtain the modified alumina carrier; the acid solution is one or a mixture of oxalic acid, nitric acid, sulfuric acid and hydrochloric acid.
(2) Vacuumizing the modified alumina carrier in the step (1) for 1 hour;
(3) preparing cobalt nitrate solution, and adding a surfactant into the solution, wherein the cobalt content is 15-30% and the surfactant content is 1-5% in percentage by weight of the catalyst, so as to obtain an impregnation solution; the surfactant is one or more of L-arginine, Cetyl Trimethyl Ammonium Bromide (CTAB) and polyvinylpyrrolidone (PVP).
(4) Absorbing the prepared impregnation liquid into the modified alumina carrier subjected to vacuum treatment, aging for 1 hour at 80 ℃, drying for 4-8 hours at 80 ℃, drying for 6-12 hours at 120 ℃, and roasting for 3 hours at 500 ℃ at 300-;
(5) introducing hydrogen into the calcined catalyst to reduce the catalyst for 10 to 30 hours at the temperature of 200-550 ℃ to obtain the cobalt/alumina catalyst.
The catalyst is applied to the reaction of preparing ethylamine by hydroamination of ethanol, can keep high activity and excellent stability of the catalyst at a lower reaction temperature, effectively reduces the occurrence of side reactions, and improves the selectivity of ethylamine.
The invention has the advantages that: the catalyst has the characteristics of high cobalt dispersion as an active component, high low-temperature activity, good stability and the like in the ethanol hydroamination reaction process. The catalyst can keep higher activity and stability at lower reaction temperature in the ethanol amination reaction.
Drawings
FIG. 1 compares the performance of the catalyst of the present invention with that of a comparative and commercial catalyst.
Detailed Description
The following examples further illustrate the invention but are not intended to limit the invention thereto.
Example 1
Treating a spherical alumina carrier containing 3.0% of silicon oxide by one or more of 3% of oxalic acid, nitric acid, sulfuric acid and hydrochloric acid at 80 ℃, washing for 2 times, drying at 120 ℃, and roasting at 650 ℃ for 3 hours to obtain a catalyst carrier;
weighing cobalt nitrate and 5% polyvinylpyrrolidone according to the content of an active component cobalt, dissolving the cobalt nitrate and the 5% polyvinylpyrrolidone in water to prepare a solution, vacuumizing the modified alumina carrier, absorbing the impregnation solution into the carrier by adopting a conventional impregnation method, aging at 80 ℃ for 1 hour, drying at 80 ℃ for 6 hours, drying at 120 ℃ for 12 hours, and roasting at 450 ℃ for 3 hours; introducing hydrogen into the calcined catalyst to reduce the catalyst for 20 hours at 500 ℃.
Catalyst a prepared in this example contained 26% cobalt.
Example 2
Catalyst B was prepared in the same manner as in example 1, except that the cobalt content of the catalyst was 20%, and 1% CTAB and 4% PVP were added to the impregnation solution.
Example 3
Catalyst C was prepared in the same manner as in example 1, except that the cobalt content of the catalyst was 15% and 3% L-arginine was added to the impregnation solution.
Example 4
Catalyst D was prepared in the same manner as in example 1, except that the cobalt content of the catalyst was 30% and 5% PVP was added to the impregnation solution.
Comparative example 1
Catalyst E was prepared in the same manner as in example 1 except that the alumina support was not treated with one or more of oxalic acid, nitric acid, sulfuric acid and hydrochloric acid, the cobalt content of the catalyst was 26%, and 5% PVP was added to the impregnation solution.
Comparative example 2
Catalyst F was prepared in the same manner as in example 1, except that the alumina support was not treated with one or more of oxalic acid, nitric acid, sulfuric acid and hydrochloric acid, the cobalt content of the catalyst was 26%, and no surfactant was added to the impregnation solution.
Example 5
The catalyst performance test is carried out in a self-made small-scale reaction device. The diameter of the reactor is 14mm, the catalyst loading is 7g, the reaction pressure is 1.5MPa, the reaction temperature is 140 ℃, and the ethanol airspeed is 0.23h-1Alcohol-ammonia molar ratio of 2.0 and hydrogen-alcohol molar ratio of 5.
The product was analyzed on-line by Shimadzu GC-2014 chromatography, TCD detector, hydrogen as carrier gas. The data in the reaction results neglected water and ammonia in the product. The specific evaluation results are shown in Table 1.
Taking the catalyst A as a representative, the reaction conditions are the same as the catalyst performance test conditions compared with the activity and stability of the catalyst E in the comparative example 1, the catalyst G in domestic industry (containing 26% of cobalt) and the catalyst H in imported industry (containing 46% of cobalt), and the results are shown in FIG. 1. Table 2 shows the results of the 500-hour stability experiment of the catalyst A of the present invention, wherein the reaction temperature is 140 ℃ and the reaction pressure is 1.5 MPa.
TABLE 1 evaluation results of catalysts
Table 2 stability test results for catalyst a of the present invention
| Reaction time (h) | 2 | 100 | 270 | 391 | 500 |
| Ethanol conversion (%) | 97.41 | 95.94 | 95.44 | 95.19 | 94.19 |
| Monoethylamine (mol%) | 11.64 | 10.53 | 10.06 | 12.82 | 12.04 |
| Diethylamine (mol%) | 44.68 | 40.92 | 40.16 | 37.57 | 37.87 |
| Triethylamine (mol%) | 40.26 | 38.55 | 39.74 | 39.29 | 38.34 |
| Ethanol (mol%) | 5.73 | 8.82 | 10.03 | 10.31 | 11.75 |
Claims (2)
1. The application of the catalyst in the reaction of preparing ethylamine by ethanol amination is characterized in that the catalyst takes cobalt as a main active component, modified alumina as a carrier, and a conventional impregnation method is adopted to prepare the cobalt/alumina catalyst; the cobalt content is 15-30% by weight of the catalyst;
the modified alumina carrier is obtained by modifying silicon oxide and one or more of oxalic acid, nitric acid, sulfuric acid and hydrochloric acid;
the impregnation method is that a surfactant is added in the process of impregnating cobalt nitrate;
the surfactant is one or more of L-arginine, cetyl trimethyl ammonium bromide and polyvinylpyrrolidone.
2. The application of the catalyst of claim 1 in the reaction of preparing ethylamine by ethanol amination is characterized in that the preparation method of the catalyst comprises the following specific steps:
(1) treating the molded alumina carrier containing 0.1-5.0 wt% of silicon oxide by using 1-5 wt% of acid solution at 80 ℃, washing for 1-2 times, drying at 120 ℃, and roasting at 400-800 ℃ for 3-5 hours to obtain the modified alumina carrier;
(2) vacuumizing the modified alumina carrier in the step (1) for 1 hour;
(3) preparing cobalt nitrate solution, and adding a surfactant into the solution, wherein the cobalt content is 15-30% and the surfactant content is 1-5% in percentage by weight of the catalyst, so as to obtain an impregnation solution;
(4) absorbing the prepared impregnation liquid into the modified alumina carrier subjected to vacuum treatment, aging for 1 hour at 80 ℃, drying for 4-8 hours at 80 ℃, drying for 6-12 hours at 120 ℃, and roasting for 3 hours at 500 ℃ at 300-;
(5) introducing hydrogen into the calcined catalyst to reduce the catalyst for 10 to 30 hours at the temperature of 200-550 ℃ to obtain the cobalt/alumina catalyst.
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| CN114433088B (en) * | 2020-10-30 | 2023-07-21 | 中国石油化工股份有限公司 | Catalyst and carrier with function of catalyzing hydro-ammonification of alcohol to generate organic amine, and preparation method and application thereof |
| CN112517051B (en) * | 2021-01-18 | 2022-11-01 | 陕西延长石油（集团）有限责任公司 | Catalyst for preparing ethylamine by ethanol amination and preparation method and application thereof |
| CN113956164A (en) * | 2021-09-30 | 2022-01-21 | 华东理工大学 | Method for efficiently synthesizing primary amine |
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