CN106349470B - It is a kind of using load-type ion liquid as the method for catalyst preparation polyetheramine - Google Patents
It is a kind of using load-type ion liquid as the method for catalyst preparation polyetheramine Download PDFInfo
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- CN106349470B CN106349470B CN201610745577.4A CN201610745577A CN106349470B CN 106349470 B CN106349470 B CN 106349470B CN 201610745577 A CN201610745577 A CN 201610745577A CN 106349470 B CN106349470 B CN 106349470B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0292—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate
- B01J31/0295—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate by covalent attachment to the substrate, e.g. silica
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Abstract
The present invention discloses a kind of method using load-type ion liquid as catalyst preparation polyetheramine, belongs to high-molecular compound synthesis technical field.Polyethers, liquefied ammonia and hydrogen are used as raw material, using load-type ion liquid as catalyst, the technique of packed bed reactor synthesizing polyether amine.Polyethers and liquefied ammonia pass through metering pump respectively, hydrogen is after compressor compresses, three kinds of raw materials are sufficiently mixed under the action of magnet valve is stirred, it squeezes into and is pre-loaded with loaded ionic liquid body catalyst and is warming up to 80 120 DEG C, Hydrogen Vapor Pressure be 48 MPa packed bed reactor in, the residence time be 5 10min, after by gas-liquid separator, unreacted ammonia and hydrogen are recycled, in case recycling；Heavy constituent obtains product polyether amine after rectifying.The present invention has many advantages, such as that low energy consumption, investment small, polyethers conversion ratio and high selectivity, catalyst is efficient, service life cycle is long, environmental-friendly, cleaning, by-product is few, waste water is few, safe, meets the direction that contemporary green chemical technology develops.
Description
Technical field
The present invention relates to it is a kind of using load-type ion liquid as the method for catalyst preparation polyetheramine more particularly to it is a kind of with
Load-type ion liquid is catalyst, and the method that polyetheramine is prepared under temperate condition belongs to high-molecular compound synthetic technology neck
Domain.
Background technology
Polyetheramine (polyetheramine) is also referred to as amine terminated polyether (amino-terminated polyether), is
One kind has flexible polyether backbone, and end (typically contains active primary amine groups, secondary amine or polyamino base with amido or amino
Group) sealing end a kind of compound general name.Polyether backbone is usually by polyoxyethylene (polyoxyethylene), polyoxypropylene
(polyoxypropylene), PolyTHF (polyoxytetramethylene), polyoxypropylene polyoxyethylene-polyoxy third
Alkene (PO-EO-PO) copolymer is formed.
The synthetic method of polyetheramine mainly has leaving group method, polyethers nitrile alkylation process, amino-butenate method, urges at present
Change ammoniation process etc..Catalytic ammoniation becomes domestic and international scientific worker's research since its product quality is stable, meets environmental requirement
Focus.
Patent application CN104693434A discloses a kind of production method of fixed bed serialization method synthesizing polyether amine.Using
Nickel-loaded, copper and lanthanum activation framework metal Raney nickel fixed bed reactors, with 130-280 DEG C of temperature and pressure 3-
The technique of synthesizing polyether amine under the conditions of 15MPa.
The technique that patent application CN105542146A discloses the synthesizing polyether amine in shell and tube reactor.The catalysis of use
Agent is made of carrier and active component, and active component is by mass ratio：In nickel 5 ~ 15%, cobalt 5 ~ 10%, rhenium 2 ~ 10%, lanthanum 1 ~ 5%
Arbitrary three kinds or more combination, the quality of active component is than nickel 8.5%, cobalt 6.5%, rhenium 3.0%.Reaction temperature is 150
~ 190 DEG C, pressure is 4.0 ~ 8.0MPa.
Patent application CN102336903A discloses a kind of production technology of aliphatic poly ether amines, and use is skeleton nickel catalyzed
Agent.Metallic nickel accounts for 85 ~ 95%, and metallic aluminium accounts for 15 ~ 5%.Reaction temperature is 120 ~ 250 DEG C, 8 ~ 35MPa of reaction pressure, the reaction time
For 1.5 ~ 8h.
Patent application CN105399940A discloses a kind of method for preparing polyetheramine.Average molecular weight is used as 100-
1000 polyethers is raw material, and polyetheramine is prepared under the effect of hydrogen, amine catalyst and metal supported catalyst.Catalyst is coprecipitated
Shallow lake metallic catalyst, 160-220 DEG C of reaction temperature, pressure 8-20MPa.
In synthesis phase urged using load type metal in above-mentioned several techniques on the synthesizing polyether amine of continuity method
Agent, reaction temperature and pressure are higher, cause equipment investment cost high, and metallic catalyst service life is short, after inactivation
It in removal process, is easily lost in environment, pollutes water and soil resources.Therefore exploitation new green environment protection technique, is always industry
Boundary and the hot spot of scientist's research.
The content of the invention
The purpose of the present invention is to solve in existing synthesizing polyether amine technology, there are high energy consumption, catalyst to make temperature high,
It is high to equipment requirement, it the shortcomings that cost of investment is big, provides a kind of using load-type ion liquid as catalyst preparation polyetheramine
Method, cleaning, safe, environmental-friendly, low energy consumption, small investment, can continuous production, performance stablize.
The present invention adopts the following technical scheme that：
It is a kind of using load-type ion liquid as the method for catalyst preparation polyetheramine, include the following steps：
（1）Load-type ion liquid catalyst is housed in packed bed reactor in advance；The load-type ion liquid is urged
Agent is tetramethyl ammonia disulfate [TMAm] HSO4Acidic ion liquid, carrier are the high purity aluminium oxide molecule of roller forming
Sieve；
（2）Hydrogen is driven into after compressor compresses in packed bed reactor, while is warming up to 80-120 DEG C, maintains to fill out
A reactor pressure is filled in 4-8 MPa, and holding hydrogen flowing quantity is 50-150L/h；
（3）Polyethers and liquefied ammonia are fully mixed by stirring magnet valve with the hydrogen from step (2) respectively after metering pump
It closes into packed bed reactor；
（4）It is 5 to keep the mass ratio of liquefied ammonia and polyethers in step (3):1-10:1, flow velocity is 2-10 Kg/h；
（5）By adjusting outlet valve, it is 5- to be kept for the time that material is contacted with load-type ion liquid catalyst
10min；
（6）By step（5）The heavy constituent that product obtains after gas-liquid separation is obtained, polyetheramine is obtained after rectifying.
The step（6）In unreacted ammonia and hydrogen recycle.
Simple production process, operation temperature pressure in the present invention are low, have that low energy consumption, polyethers conversion ratio and selectivity
It is high, catalyst is efficient, service life cycle is long, environmental-friendly, cleaning, by-product is few, waste water is few, it is safe the advantages that,
Meet the direction of contemporary green chemical technology development.
Description of the drawings
Fig. 1 is the process flow chart of the present invention,
Wherein shown in icon：Liquid ammonia storage tank 1, polyethers storage tank 2, metering of liquid ammonia pump 3, polyethers metering pump 4, hydrogen gas compressor 5,
Stir magnet valve 6, packed bed reactor 7, gas-liquid separator 8, hydrogen circulating line 9, Liquid liquid Separation device 10, polyetheramine storage tank 11,
Liquefied ammonia circulating line 12.
Specific embodiment
Polyethers, liquefied ammonia, hydrogen after stirring magnet valve is sufficiently mixed, are squeezed into anti-according to certain mass ratio in the present invention
It answers in device, load-type ion liquid is catalyst, carries out synthesizing polyether amine.In order to improve the conversion ratio of polyethers, excess is used
Liquefied ammonia, mass ratio 5:1-10:1, flow velocity 2-10Kg/h, hydrogen flowing quantity 50-150L/h, reactor pressure 4-8MPa,
Temperature is 80-120 DEG C, and material is 5-10min with catalyst contact time；After the completion of reaction, by two-phase seperation tower, separated
Hydrogen, liquefied ammonia and the product of amount.This method have it is easy to operate, easily realize automation control, low energy consumption, polyethers conversion ratio height etc.
Advantage.The load-type ion liquid catalyst is tetramethyl ammonia disulfate [TMAm] HSO4Acidic ion liquid, carrier
The high purity aluminium oxide molecular sieve of roller forming can be used.
Below in conjunction with attached drawing 1 and embodiment 1-6, the invention will be further described.
Embodiment 1
Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged in advance, and have been hunted leak.It is anti-that packed bed is heated first
Answer 7 to 120 DEG C of device；While heating, start hydrogen gas compressor 5 and be forced into 4 MPa to packed bed reactor 7, and keep hydrogen
Flow is 50 L/h；When bed reactor 7 to be filled is warming up to 120 DEG C, start stirring magnet valve 6, start metering of liquid ammonia pump 3, by liquid
Liquefied ammonia in ammonia storage tank 1 is added in packed bed reactor 7；Start polyethers metering pump 4 simultaneously, by the polyethers in polyethers storage tank 2
It is added to reactor；The rotating speed of two metering pumps is adjusted, it is 5 to keep liquefied ammonia and polyether quality ratio:1, flow velocity is 2 Kg/h, passes through tune
7 outlet valve size of packed bed reactor is saved to adjust the logistics residence time as 5 min；Outlet streams squeeze into gas-liquid separation through pump
Device 8, separated hydrogen are recycled through hydrogen circulating line 9；Heavy constituent is after Liquid liquid Separation device 10, unreacted liquefied ammonia warp
Liquefied ammonia circulating line 12 recycles, and product polyether amine is stored in polyetheramine storage tank 11.Sampling detection, uses gas chromatographic detection
Polyethers amine content is 98.5%.
Embodiment 2
Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged in advance, and have been hunted leak.It is anti-that packed bed is heated first
Answer 7 to 115 DEG C of device；While heating, start hydrogen gas compressor 5 and be forced into 5 MPa to reactor, and it is 60 to keep hydrogen flowing quantity
L/h；When reactor is warming up to 115 DEG C, start stirring magnet valve 6, start metering of liquid ammonia pump 3, the liquefied ammonia in liquid ammonia storage tank 1 is added
Enter into packed bed reactor 7；Start polyethers metering pump 4 simultaneously, the polyethers in polyethers storage tank 2 is added to reactor；It adjusts
The rotating speed of two metering pumps, it is 5 to keep liquefied ammonia and polyether quality ratio:1, flow velocity is 3 Kg/h, big by adjusting reactor outlet valve
It is small to adjust the logistics residence time as 6 min；Outlet streams squeeze into gas-liquid separator 8 through pump, and separated hydrogen is cycled through hydrogen
Pipeline 9 recycles；After Liquid liquid Separation device 10, unreacted liquefied ammonia recycles heavy constituent through liquefied ammonia circulating line 12,
Product polyether amine is stored in polyetheramine storage tank 11.Sampling detection is 98.9% with gas chromatographic detection polyethers amine content.
Embodiment 3
Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged in advance, and have been hunted leak.It is anti-that packed bed is heated first
Answer 7 to 110 DEG C of device；While heating, start hydrogen gas compressor 5 and be forced into 6 MPa to reactor, and it is 70 to keep hydrogen flowing quantity
L/h；When reactor is warming up to 110 DEG C, start stirring magnet valve 6, start metering of liquid ammonia pump 3, the liquefied ammonia in liquid ammonia storage tank 1 is added
Enter into packed bed reactor 7；Start polyethers metering pump 4 simultaneously, the polyethers in polyethers storage tank 2 is added to reactor；It adjusts
The rotating speed of two metering pumps, it is 6 to keep liquefied ammonia and polyether quality ratio:1, flow velocity 4Kg/h, by adjusting reactor outlet valve size
To adjust the logistics residence time as 8 min；Outlet streams squeeze into gas-liquid separator 8 through pump, and separated hydrogen is through hydrogen circulation pipe
Road 9 recycles；After Liquid liquid Separation device 10, unreacted liquefied ammonia recycles heavy constituent through liquefied ammonia circulating line 12, production
Object polyetheramine is stored in polyetheramine storage tank 11.Sampling detection is 99.1% with gas chromatographic detection polyethers amine content.
Embodiment 4
Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged in advance, and have been hunted leak.It is anti-that packed bed is heated first
Answer 7 to 100 DEG C of device；While heating, start hydrogen gas compressor 5 and be forced into 7 MPa to reactor, and it is 80 to keep hydrogen flowing quantity
L/h；When reactor is warming up to 100 DEG C, start stirring magnet valve 6, start metering of liquid ammonia pump 3, the liquefied ammonia in liquid ammonia storage tank 1 is added
Enter into packed bed reactor 7；Start metering pump 4 simultaneously, the polyethers in polyethers storage tank 2 is added to reactor；Adjust two meters
The rotating speed of pump is measured, it is 7 to keep liquefied ammonia and polyether quality ratio:1, flow velocity is 5 Kg/h, by adjusting 7 outlet valve of packed bed reactor
Size adjusts the logistics residence time as 9 min；Outlet streams squeeze into gas-liquid separator 8 through pump, and separated hydrogen is followed through hydrogen
Endless tube road 9 recycles；For heavy constituent after Liquid liquid Separation device 10, unreacted liquefied ammonia cycles profit through liquefied ammonia circulating line 12
With product polyether amine is stored in polyetheramine storage tank 11.Sampling detection is 99.5% with gas chromatographic detection polyethers amine content.
Embodiment 5
Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged in advance, and have been hunted leak.It is anti-that packed bed is heated first
Answer 7 to 90 DEG C of device；While heating, start hydrogen gas compressor 5 and be forced into 7 MPa to reactor, and keep the hydrogen flowing quantity to be
100L/h；When reactor is warming up to 90 DEG C, start stirring magnet valve 6, start metering of liquid ammonia pump 3, by the liquefied ammonia in liquid ammonia storage tank 1
It is added in packed bed reactor 7；Start polyethers metering pump 4 simultaneously, the polyethers in polyethers storage tank 2 is added to reactor；It adjusts
The rotating speed of two metering pumps is saved, it is 9 to keep liquefied ammonia and polyether quality ratio:1, flow velocity is 8 Kg/h, by adjusting packed bed reactor 7
Outlet valve size adjusts the logistics residence time as 9 min；Outlet streams squeeze into gas-liquid separator 8, separated hydrogen warp through pump
Hydrogen circulating line 9 recycles；After Liquid liquid Separation device 10, unreacted liquefied ammonia follows heavy constituent through liquefied ammonia circulating line 12
Ring utilizes, and product polyether amine is stored in polyetheramine storage tank 11.Sampling detects, and is with gas chromatographic detection polyethers amine content
98.3%。
Embodiment 6
Each temperature-controlling system, instrument and the valve of pilot-plant have been debugged in advance, and have been hunted leak.It is anti-that packed bed is heated first
Answer 7 to 80 DEG C of device；While heating, start hydrogen gas compressor 5 and be forced into 8 MPa to reactor, and it is 150 to keep hydrogen flowing quantity
L/h；When reactor is warming up to 80 DEG C, start stirring magnet valve 6, start metering of liquid ammonia pump 3, the liquefied ammonia in liquid ammonia storage tank 1 is added
Enter into packed bed reactor 7；Start polyethers metering pump 4 simultaneously, the polyethers in polyethers storage tank 2 is added to reactor；It adjusts
The rotating speed of two metering pumps, it is 10 to keep liquefied ammonia and polyether quality ratio:1, flow velocity is 10 Kg/h, by adjusting packed bed reactor 7
Outlet valve size adjusts the logistics residence time as 10 min；Outlet streams squeeze into gas-liquid separator 8, separated hydrogen warp through pump
Hydrogen circulating line 9 recycles；After Liquid liquid Separation device 10, unreacted liquefied ammonia follows heavy constituent through liquefied ammonia circulating line 12
Ring utilizes, and product polyether amine is stored in polyetheramine storage tank 11.Sampling detects, and is with gas chromatographic detection polyethers amine content
99.8%。
Claims (2)
- It is 1. a kind of using load-type ion liquid as the method for catalyst preparation polyetheramine, it is characterised in that：Include the following steps：（1）Load-type ion liquid catalyst is housed in packed bed reactor in advance；The load-type ion liquid catalyst Using tetramethyl ammonia disulfate [TMAm] HSO4Acidic ion liquid, carrier are the high purity aluminium oxide molecular sieve of roller forming；（2）Hydrogen is driven into after compressor compresses in packed bed reactor, while is warming up to 80-120 DEG C, maintains packed bed For reactor pressure in 4-8 MPa, holding hydrogen flowing quantity is 50-150L/h；（3）Polyethers and liquefied ammonia are respectively after metering pump, and the hydrogen from step (2), through stirring magnet valve be sufficiently mixed into Enter in packed bed reactor；（4）It is 5 to keep the mass ratio of liquefied ammonia and polyethers in step (3):1-10:1, flow velocity is 2-10 Kg/h；（5）By adjusting outlet valve, it is 5-10min to be kept for the time that material is contacted with load-type ion liquid catalyst；（6）By step（5）The heavy constituent that product obtains after gas-liquid separation is obtained, polyetheramine is obtained after rectifying.
- 2. the method as described in claim 1, it is characterised in that：The step（6）In unreacted ammonia and hydrogen recycle.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0356047A2 (en) * | 1988-08-18 | 1990-02-28 | BP Chemicals Limited | Primary or secondary amine terminated polyethers |
| JP2013060504A (en) * | 2011-09-12 | 2013-04-04 | Univ Of Tokyo | Ionic liquid-containing gelatinous composition, gelatinous thin film, and method for manufacturing the same |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0356047A2 (en) * | 1988-08-18 | 1990-02-28 | BP Chemicals Limited | Primary or secondary amine terminated polyethers |
| JP2013060504A (en) * | 2011-09-12 | 2013-04-04 | Univ Of Tokyo | Ionic liquid-containing gelatinous composition, gelatinous thin film, and method for manufacturing the same |
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