CN101455963A - Catalyst for preparing C2-C3 lower aliphatic amine and production method thereof - Google Patents
Catalyst for preparing C2-C3 lower aliphatic amine and production method thereof Download PDFInfo
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- CN101455963A CN101455963A CNA2008101641708A CN200810164170A CN101455963A CN 101455963 A CN101455963 A CN 101455963A CN A2008101641708 A CNA2008101641708 A CN A2008101641708A CN 200810164170 A CN200810164170 A CN 200810164170A CN 101455963 A CN101455963 A CN 101455963A
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- catalyst
- carrier
- low
- aliphatic amine
- active constituent
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Abstract
The invention discloses a catalyst for preparing C2-C6 low-grade aliphatic amine. The catalyst comprises a carrier and an active component, wherein the active component accounts for 10 to 60 percent of the total weight of the catalyst, and the active component is Co or consists of Co, Ni and Fe. The invention also discloses a method for producing the catalyst, which comprises the steps of putting the carrier into an aqueous solution of the active component for impregnation, loading the active component onto the carrier, drying the impregnated carrier at a temperature between 100 and 180 DEG C and then decomposing the carrier at a temperature between 250 and 550 DEG C, using hydrogen to perform reduction treatment at a temperature between 250 and 650 DEG C and obtaining the catalyst. The catalyst adopted to prepare the C2-C6 low-grade aliphatic amine can be more beneficial to the generation of tertiary amine.
Description
Technical field
The present invention relates to a kind of C that is used to prepare
2～C
6The catalyst of low-grade aliphatic amine and production method thereof; Specifically, relating to a kind of being used for is facing lower aliphatic alcohols and corresponding aldehyde, ketone under hydrogen or the hydrogenated state, and ammonification prepares the Catalysts and its preparation method of amine.
Background technology
In chemical industry, aminated compounds generally includes primary amine, secondary amine, tertiary amine, and low-grade aliphatic amine is widely used in agricultural chemicals, medicine and other fields.They are usually by alcohol and corresponding aldehyde, ketone, facing under the situation that hydrogen or hydrogenated state and catalyst exist, carry out the aminating reaction preparation, and the mechanism of aminating reaction can be divided into for three steps: the first step, and the raw alcohol dehydrogenation generates aldehydes or ketones; In second step, aldehydes or ketones and ammonia addition generate imines; In the 3rd step, the further hydrogenation of imines generates amine.
U.S. Pat 4255357 provides a kind of and has been combined as carrier (preferred vector is diatomite and gama-alumina) with silica, natural tripoli ore deposit, synthetic cimita, aluminium oxide or its, the load cobalt is made catalyst, under the effect of facing hydrogen state and catalyst, make ethanol and ammonia react prepare the method for ethamine by the gas-solid bed.Because the restriction of carrier property, maximum conversion is 64.9% among the embodiment, and the triethylamine ratio is lower in the product.
Chinese patent CN1057831A has reported a kind of by C
2-C
9Fatty alcohol prepares the method for fatty amine, and this method divides two sections to carry out, two sections catalyst system therefor differences.The typical scenario of first section used catalyst of reaction is CuSi
1.5O
3, the typical scenario of second section used catalyst of reaction is CoZnSi
7.5O
8.5But the process reaction temperature is high 260 ℃.Because adopt two-stage method, technological process is longer, need higher equipment investment, and the preparation catalyst is also comparatively complicated.
Chinese patent CN1151984A has reported a kind of aminating reaction catalyst, by carrier loaded Ni, Zn, Fe isoreactivity component, wherein active constituent shared percentage by weight in catalyst is 30 1 70wt%, all the other are carrier. this catalyst can be applied to all kinds of aminating reactions, but reaction temperature is higher.Though generated primary, secondary, tertiary amine can regulate within the specific limits, adjustable range is less, and is especially relatively poor to the adjusting of tertiary amine.For example catalyst is used for the course of reaction of ethanol ammonification system ethamine, and the ethanol liquid air speed only is 0.24h
-1, the yield of tertiary amine is about 20%.
Chinese patent ZL02104202.0 has reported a kind of preparation C
2-C
4The Catalysts and its preparation method of low-grade aliphatic amine and application.SiO
2Carrier loaded Co
++The property component, the content of active component is at 10-50%.This catalyst carrier adopts the preparation of sodium metasilicate precipitation neutralisation.Catalyst is executed in the example at ethanol system ethamine, and catalyst loading is lower, and the ethanol liquid air speed is 0.3h
-1Preparation flow is long and technological parameter is wayward, amplifies poor repeatability, should not amplify popularization.
Chinese patent ZL00105224.1 has reported a kind of C
2--c
8Fatty alcohol amination catalyst and technology.Carrier is SiO
2Or SiO
2And Al
2O
3Mixture.Active component is the mixture of cobalt or cobalt and nickel.Catalyst loading is low, ethanol liquid air speed 0.15-0.4h
-1, ethanol conversion is about 90%.This patent method for preparing catalyst complexity, flow process is longer.
Chinese patent ZL95194467.3 has reported a kind of Co catalysts that is stated from the aluminium oxide.Active component is a carbonate, and the repeatedly mode (1-4 times) of dipping is adopted in ammonium carbonate and ammoniacal liquor preparation, and the amount of active ingredients of each dipping is 3-4%.Dipping process is more loaded down with trivial details.And this patent is not reported relevant Application Example aspect low-grade aliphatic amine.
Summary of the invention
The technical problem to be solved in the present invention provides a kind of C that is used to prepare
2～C
6The catalyst of low-grade aliphatic amine and production method thereof adopt Preparation of Catalyst C of the present invention
2～C
6Low-grade aliphatic amine not only can be simplified the Preparation of Catalyst flow process, reduce reaction temperature, can also make generated primary, secondary, tertiary amine has proportion adjustable in a big way, can more help the generation of tertiary amine.
In order to solve the problems of the technologies described above, the invention provides a kind of C that is used to prepare
2～C
6The catalyst of low-grade aliphatic amine, this catalyst comprises carrier and active constituent, active constituent accounts for 10～60% of catalyst gross weight; Active constituent is Co, and perhaps active constituent is made up of Co, Ni and Fe, atomic ratio=1:0.04 of Co:Ni～0.8, atomic ratio=1:0.02 of Co:Fe～0.2.
Improvement as catalyst of the present invention: catalyst also comprises auxiliary agent, and auxiliary agent accounts for 0.02～0.2% of catalyst gross weight; Auxiliary agent is at least a among Mg, K and the Mn.
Further improvement as catalyst of the present invention: carrier is at least a in silica, alumina support, diatomite and the active carbon.
Further improvement as catalyst of the present invention: carrier is the mixture of silica and aluminium oxide or is the mixture of alumina support and active carbon.
The present invention also provides the production method of above-mentioned catalyst simultaneously, may further comprise the steps: the aqueous solution of carrier being put into active constituent floods, and active constituent is loaded on the carrier; The aqueous solution of perhaps carrier being put into active constituent and auxiliary agent floods, and active constituent and auxiliary agent are loaded on the carrier; Then with the carrier after the above-mentioned impregnation process successively after 100～180 ℃ of dryings and 250～550 ℃ of decomposition, at last with hydrogen after 250～650 ℃ of reduction are handled, catalyst.
Improvement as the production method of catalyst of the present invention: the time of drying steps is 1～10 hour, and the time of decomposition step is 1～10 hour, and the reduction processing time is 12～20 hours.
Further improvement as the production method of catalyst of the present invention, the preparation method of alumina support is as follows: adopting the low silicon of carbonizatin method or sulfuric acid process preparation or the boehmite of high silicon is raw material, through the moulding and dry processing of routine, getting granularity is the initial oxidation alumina supporter of Φ 1.5-5mm * 3-8mm then; Then described initial oxidation alumina supporter is put into the high temperature furnace roast, 500～1200 ℃ of roasts 5～15 hours, alumina support.
The present invention also provides the purposes of above-mentioned catalyst simultaneously, is used to prepare C
2～C
6Low-grade aliphatic amine.
In the present invention, when containing auxiliary agent in the catalyst, Co: auxiliary agent (mol)=1:0.02～0.2.
In the present invention, the Al that selects for use
2O
3The carrier specific surface is 100～150m
2/ g, bulk density 0.5～0.9g/ml, crushing strength〉the 5N/ grain.
Catalyst of the present invention is applicable to all kinds of aminating reactions, is particularly useful for the preparation of low-grade aliphatic amine; Promptly by alcohol and corresponding aldehyde, ketone, facing under hydrogen or the hydrogenated state, aminating reaction prepares low-grade aliphatic amine.
The method that catalyst of the present invention is used to prepare fatty amine is: adopt the fixed bed reactors reaction.Reaction condition: reaction temperature is 140～280 ℃, reaction pressure 0.8～2.8MPa, and the liquid air speed of alcohol (aldehydes or ketones) is 0.05～2.5h
-1Charge ratio is an alcohol (aldehydes or ketones): ammonia: hydrogen=1:1～4:1～8 (mol), by above-mentioned condition alcohol (aldehydes or ketones), ammonia, hydrogen are fed fixed bed reactors, catalyst of the present invention is housed in the reactor, in reactor, carry out aminating reaction, thereby generate aminated compounds.
Compared with prior art, the present invention has the following advantages:
1), utilize the reaction condition of Preparation of Catalyst fatty amine of the present invention suitable, under certain pressure, can improve reaction rate, improve the conversion ratio of product.
2), when utilizing Preparation of Catalyst low-grade aliphatic amine of the present invention, one step of aminating reaction finishes, the operation simple and convenient.
3), utilize Preparation of Catalyst fatty amine of the present invention, have advantages of high catalytic activity, the catalyst loading height.For example in the reaction of ethanol hydrogen ammonification system ethamine, ethanol liquid air speed: 0.8h
-1During the left and right sides, ethanol conversion 〉=96%.
4), the present invention adopts low silicon or high silicon boehmite, through high-temperature roasting, makes carrier.Coexistence gama-alumina and δ-aluminium oxide in the carrier, this Al
2O
3In the crystalline phase of carrier, 60～80% is the γ type, and 20～40% is the δ type.Behind the dipping active component cobalt, has advantages of high catalytic activity.
5), utilize Preparation of Catalyst fatty amine of the present invention, have good selectivity, the growing amount of the middle-and-high-ranking amine of accessory substance is few, final product is easily separated.
6), utilize Preparation of Catalyst fatty amine of the present invention, product primary amine: secondary amine: the ratio of tertiary amine can be at (10-40) %:(30-60) %:(10-40) regulate in the % scope.This method more helps the generation of tertiary amine.
7), utilize Preparation of Catalyst fatty amine of the present invention, catalyst has excellent mechanical intensity and stability.
8), utilize Preparation of Catalyst fatty amine of the present invention, range of application is wider, the catalyst long service life.
The specific embodiment
Embodiment 1, a kind ofly be used to prepare C
2～C
6The production method of the catalyst of low-grade aliphatic amine, carry out following steps successively:
1), preparation carrier:
Adopt the boehmite 500g of the macropore high-ratio surface of low silicon (or high silicon), add the 30g carbon black, add mass concentration 65% (Wt) aqueous solution of nitric acid 10ml, add the aqueous solution 20ml of the citric acid preparation of the phosphate aqueous solution 2ml of 98% (Wt) and 5g again, mediated 60～100 minutes through kneader.Be extruded into φ 3.5mm * 5.0m bar through banded extruder then, after 80-160 ℃ of oven dry, get the initial oxidation alumina supporter.
The initial oxidation alumina supporter is put into 950 ℃ of roasts of muffle furnace 12 hours, finally obtain Al
2O
3Carrier.
2), preparation catalyst:
With 170g cobalt nitrate, 18.5g nickel nitrate, 6.0 ferric nitrates, the 6.9g magnesium nitrate is dissolved in respectively in the deionized water of 60g, 6.0g, 2g and 2.3g, makes the aqueous solution of corresponding active constituent or auxiliary agent earlier.With above-mentioned 4 kinds of aqueous solution, get mixed liquor.
Get the Al of 100g step 1) gained
2O
3Carrier is put into above-mentioned mixed liquor and is flooded, and can evenly stir in the dipping process, and dip time is 60～100 minutes; Take out then in 150 ℃ of oven dry 4 hours; Then under 450 ℃ temperature, decomposed 4 hours, until not having NO and NO
2Till emerging.Repeat once above-mentioned dipping, oven dry and decomposition step more successively.Feed hydrogen at last and carry out reduction reaction under 550 ℃ temperature, the recovery time is 15 hours.
Contain 24.69% cobalt in the catalyst of gained, 2.65% nickel, 0.09% iron, 0.1% magnesium.
In order to prove the characteristic of catalyst of the present invention, the inventor has made following confirmatory experiment:
Experiment 1,
Experimental provision: adopt fixed bed reactors, the specification of reactor is φ 25m (internal diameter) * 600mm, and material is a stainless steel.Reactor is divided into two sections, and epimere is for mixing preheating section, and hypomere is a conversion zone, the interpolation thermometer boss.The consumption of each evaluate catalysts is 100ml, and the product gas, liquid is with homemade SP-6890 gas chromatographic analysis.
With ethanol is raw material, is facing under the hydrogen state, and aminating reaction is produced ethamine.Catalyst is selected the catalyst of embodiment 1 gained for use.
Reaction condition is as follows: reaction temperature: 160 ℃, pressure is 1.5MPa, alcohol: ammonia: hydrogen=1.2:3.5:3.5 (mol), ethanol air speed: 0.8h
-1, reaction result is as shown in table 1:
Table 1
MEA represents monoethyl amine in the table, and DEA represents diethylamine, and TEA represents triethylamine
Contrast experiment 1, the catalyst that will test the embodiment of the invention 1 in 1 make the catalyst of being informed in the U.S. Pat 4255357 into, and loading is 0.3h
-1About.All the other experimental techniques all are equal to experiment 1, and the gained result is as shown in table 2.
Table 2
Contrast experiment 2, the catalyst that will test the embodiment of the invention 1 in 1 make the catalyst of being informed among the Chinese patent ZL02104202.0 into, and loading is 0.3h
-1All the other test methods all are equal to experiment 1, and the gained result is as shown in table 3.
Table 3
According to the data contrast of table 1 and table 2, table 3, can learn: it is high that catalyst of the present invention has a load, the advantage that the selectivity of ethanol conversion height, triethylamine is high.
Experiment 2,
Experimental provision is with experiment 1.
With the isopropyl alcohol is raw material, is facing under the hydrogen state, and aminating reaction is produced isopropylamine.Catalyst is selected the catalyst of embodiment 1 gained for use.
Reaction condition is as follows: reaction temperature: 150 ℃, pressure is 1.8MPa, alcohol: ammonia: hydrogen=1:3:3 (mol), isopropyl alcohol air speed: 0.50h
-1, reaction result is as shown in table 4.
Table 4
In the table: MIPA represents Mono Isopropylamine, and DIPA represents diisopropylamine.
Experiment 3,
Experimental provision is with experiment 1.
With the n-butanol is raw material, is facing under the hydrogen state, and aminating reaction is produced n-butylamine.Catalyst is selected the catalyst of embodiment 1 gained for use.
Reaction condition: reaction temperature: 180 ℃, pressure is 1.8MPa, alcohol: ammonia: hydrogen=1:3:3 (mol), n-butanol air speed: 0.50h
-1, reaction result is as shown in table 5.
Table 5
In the table: MBA---one n-butylamine, DBA---di-n-butylamine, TBA---tri-n-butylamine
Experiment 4,
Experimental provision is with experiment 1.
With the normal propyl alcohol is raw material, is facing under the hydrogen state, and aminating reaction is produced n-propylamine.Catalyst is selected the catalyst of embodiment 1 gained for use.
Reaction condition: reaction temperature: 190 ℃, pressure is 1.5MPa, alcohol: ammonia: hydrogen=1:3:3 (mol), normal propyl alcohol air speed: 0.50h
-1, reaction result is as shown in table 6.
Table 6
At last, it is also to be noted that what more than enumerate only is several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (8)
1, a kind ofly is used to prepare C
2～C
6The catalyst of low-grade aliphatic amine is characterized in that: this catalyst comprises carrier and active constituent, and described active constituent accounts for 10～60% of catalyst gross weight; Described active constituent is Co, and perhaps active constituent is made up of Co, Ni and Fe, atomic ratio=1:0.04 of Co:Ni～0.8, atomic ratio=1:0.02 of Co:Fe～0.2.
2, according to claim 1ly be used to prepare C
2～C
6The catalyst of low-grade aliphatic amine is characterized in that: described catalyst also comprises auxiliary agent, and described auxiliary agent accounts for 0.02～0.2% of catalyst gross weight; Described auxiliary agent is at least a among Mg, K and the Mn.
3, according to claim 1 and 2ly be used to prepare C
2～C
6The catalyst of low-grade aliphatic amine is characterized in that: described carrier is at least a in silica, alumina support, diatomite and the active carbon.
4, according to claim 3ly be used to prepare C
2～C
6The catalyst of low-grade aliphatic amine is characterized in that: described carrier is the mixture of silica and aluminium oxide or is the mixture of alumina support and active carbon.
5, as any one is used to prepare C in the claim 1～4
2～C
6The production method of the catalyst of low-grade aliphatic amine is characterized in that may further comprise the steps: the aqueous solution of carrier being put into active constituent floods, and active constituent is loaded on the carrier; The aqueous solution of perhaps carrier being put into active constituent and auxiliary agent floods, and active constituent and auxiliary agent are loaded on the carrier; Then with the carrier after the above-mentioned impregnation process successively after 100～180 ℃ of dryings and 250～550 ℃ of decomposition, at last with hydrogen after 250～650 ℃ of reduction are handled, catalyst.
6, the production method of catalyst according to claim 5 is characterized in that: the time of described drying steps is 1～10 hour, and the time of described decomposition step is 1～10 hour, and the reduction processing time is 12～20 hours.
7, according to the production method of claim 5 or 6 described catalyst, it is characterized in that: the preparation method of alumina support is as follows: adopting the low silicon of carbonizatin method or sulfuric acid process preparation or the boehmite of high silicon is raw material, through the moulding and dry processing of routine, getting granularity is the initial oxidation alumina supporter of Φ 1.5-5mm * 3-8mm then; Then described initial oxidation alumina supporter is put into the high temperature furnace roast, 500～1200 ℃ of roasts 5～15 hours, alumina support.
8, preparing C as any one catalyst in the claim 1～4
2～C
6Application in the low-grade aliphatic amine.
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|---|---|---|---|
| CNA2008101641708A CN101455963A (en) | 2008-12-29 | 2008-12-29 | Catalyst for preparing C2-C3 lower aliphatic amine and production method thereof |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102336672A (en) * | 2011-09-21 | 2012-02-01 | 浙江建业化工股份有限公司 | Method for producing isoamyl amine |
| CN102614892A (en) * | 2012-03-04 | 2012-08-01 | 浙江大学 | Synthesis method of triethylamine and catalyst used in method |
| CN102614893A (en) * | 2012-03-04 | 2012-08-01 | 浙江建业化工股份有限公司 | Method for combining tributylamine and used catalyst |
| CN103965055A (en) * | 2014-05-26 | 2014-08-06 | 浙江建业化工股份有限公司 | Synthesis method of isopropyl amine |
| CN105992754A (en) * | 2014-02-18 | 2016-10-05 | 巴斯夫欧洲公司 | Method for producing n-ethyl-diisopropylamine |
| CN107915645A (en) * | 2017-10-12 | 2018-04-17 | 浙江晋巨化工有限公司 | A kind of n-butylamine production method |
| CN109622006A (en) * | 2018-11-30 | 2019-04-16 | 中国科学院山西煤炭化学研究所 | One kind lower fatty amine catalyst containing ammonia synthesis gas and preparation method thereof |
| CN112044447A (en) * | 2020-08-18 | 2020-12-08 | 西安近代化学研究所 | Catalyst for synthesizing monoethylamine, preparation method and application |
| CN113042041A (en) * | 2019-12-27 | 2021-06-29 | 中国石油化工股份有限公司 | Coal tar hydrogenation catalyst, and preparation method and application thereof |
| CN113185411A (en) * | 2021-04-18 | 2021-07-30 | 浙江建业化工股份有限公司 | Method for improving yield and purity of di-n-propylamine produced continuously based on deoxygenation technology |
-
2008
- 2008-12-29 CN CNA2008101641708A patent/CN101455963A/en active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102336672A (en) * | 2011-09-21 | 2012-02-01 | 浙江建业化工股份有限公司 | Method for producing isoamyl amine |
| CN102336672B (en) * | 2011-09-21 | 2014-06-18 | 浙江建业化工股份有限公司 | Method for producing isoamyl amine |
| CN102614892A (en) * | 2012-03-04 | 2012-08-01 | 浙江大学 | Synthesis method of triethylamine and catalyst used in method |
| CN102614893A (en) * | 2012-03-04 | 2012-08-01 | 浙江建业化工股份有限公司 | Method for combining tributylamine and used catalyst |
| CN102614892B (en) * | 2012-03-04 | 2014-01-01 | 浙江大学 | Synthesis method of triethylamine and catalyst used in method |
| CN102614893B (en) * | 2012-03-04 | 2014-01-01 | 浙江建业化工股份有限公司 | Method for combining tributylamine and used catalyst |
| CN105992754A (en) * | 2014-02-18 | 2016-10-05 | 巴斯夫欧洲公司 | Method for producing n-ethyl-diisopropylamine |
| CN103965055B (en) * | 2014-05-26 | 2015-11-18 | 浙江建业化工股份有限公司 | The synthetic method of Isopropylamine |
| CN103965055A (en) * | 2014-05-26 | 2014-08-06 | 浙江建业化工股份有限公司 | Synthesis method of isopropyl amine |
| CN107915645A (en) * | 2017-10-12 | 2018-04-17 | 浙江晋巨化工有限公司 | A kind of n-butylamine production method |
| CN109622006A (en) * | 2018-11-30 | 2019-04-16 | 中国科学院山西煤炭化学研究所 | One kind lower fatty amine catalyst containing ammonia synthesis gas and preparation method thereof |
| CN109622006B (en) * | 2018-11-30 | 2021-11-12 | 中国科学院山西煤炭化学研究所 | Catalyst for preparing low-grade aliphatic amine from ammonia-containing synthesis gas and preparation method thereof |
| CN113042041A (en) * | 2019-12-27 | 2021-06-29 | 中国石油化工股份有限公司 | Coal tar hydrogenation catalyst, and preparation method and application thereof |
| CN113042041B (en) * | 2019-12-27 | 2022-03-08 | 中国石油化工股份有限公司 | Coal tar hydrogenation catalyst, and preparation method and application thereof |
| CN112044447A (en) * | 2020-08-18 | 2020-12-08 | 西安近代化学研究所 | Catalyst for synthesizing monoethylamine, preparation method and application |
| CN112044447B (en) * | 2020-08-18 | 2023-02-14 | 西安近代化学研究所 | Catalyst for synthesizing monoethylamine, preparation method and application |
| CN113185411A (en) * | 2021-04-18 | 2021-07-30 | 浙江建业化工股份有限公司 | Method for improving yield and purity of di-n-propylamine produced continuously based on deoxygenation technology |
| CN113185411B (en) * | 2021-04-18 | 2023-08-04 | 浙江建业化工股份有限公司 | Method for improving yield and purity of continuously producing di-n-propylamine based on deoxidization technology |
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