CN106083582A - A kind of system and method for acetylene carbonylation acrylic acid methyl ester. - Google Patents
A kind of system and method for acetylene carbonylation acrylic acid methyl ester. Download PDFInfo
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- CN106083582A CN106083582A CN201610658918.4A CN201610658918A CN106083582A CN 106083582 A CN106083582 A CN 106083582A CN 201610658918 A CN201610658918 A CN 201610658918A CN 106083582 A CN106083582 A CN 106083582A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
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Abstract
The present invention discloses the system and method for a kind of acetylene carbonylation acrylic acid methyl ester..This system includes: acetylene dissolving tank, reactor, the first gas-liquid separator, the second gas-liquid separator, carbon monoxide extraction element and compressor, and described acetylene dissolving tank is provided with acetylene entrance, non-polar organic solvent entrance and liquid outlet；Described reactor includes solvents for ethyne entrance, carbon monoxide gas inlet and gas outlet；Described first gas-liquid separator includes gas access, gas outlet and acrylic acid methyl ester. outlet；Described second gas-liquid separator includes gas access and gas outlet.The present invention can be by product by the difference of recovered (distilled) temperature, and by-product and solvent separate, and make carbon monoxide and organic solvent cycling and reutilization, economize in raw materials, and reduces cost.
Description
Technical field
The invention belongs to chemical field, particularly relate to the system and method for a kind of acetylene carbonylation acrylic acid methyl ester..
Background technology
Along with petroleum resources are the most exhausted, Development of Coal chemical products are that the chemical process of raw material becomes petroleum replacing chemical industry road
The significant process of line, obtains extensive concern, and obtains fast development.
Esters of acrylic acid is one of important fine chemical material, is mainly used as organic synthesis intermediate and synthesis macromolecule
The monomer of material.Because of quite varied, in homopolymerization containing carbon-to-carbon unsaturated double-bond purposes in acrylic acid methyl ester. chemical constitution
Be widely used, can aggregated, copolymerization, exchange, emulsion-type, water-soluble and solvent type crylic acid resin are made in grafting etc.
Product.Acrylic acid methyl ester. can be used to produce lucite, it is possible to is used for manufacturing other resins, plastics, coating, binding agent, lubrication
Agent etc..At present, the production of acrylic acid methyl ester. mainly has the synthesis of acrylic acid and methanol esterification and acetylene, carbon monoxide, methanol direct
Oxo process.The acrylic acid of acroleic acid esterification method mainly uses propylene fraction oxidizing process to prepare, and production cost is relatively low, but this method
The petroleum resources that undue dependence is the most nervous.And acetylene carbonylation method is directly synthesized acrylic acid methyl ester., it is independent of oil, the suitableeest
Together in oil-poor, rich gas, rich coal country development fine chemistry industry.China's coal, natural gas resource are abundant, and rich product carbide,
And in carbide legal system acetylene tail gas containing substantial amounts of carbon monoxide can as the carbonyl source of synthesizing acrylic acid from acetylene carbonyl methyl ester,
Therefore, this route has resources advantage in China's development.
Owing to acetylene carbonyl turns to strong exothermal reaction, reaction selectivity temperature influence is obvious, and reaction is many in solution-air mode
Carry out.Even if acetylene, carbon monoxide react in very harsh condition the most hardly with methanol, develop effective catalyst one
It it is directly the focus of synthesizing acrylic acid from acetylene carbonyl route.Reppe method original adoption Nickel tetracarbonyl. makees catalyst, enters catalyst subsequently
The substantial amounts of improvement of row, the stechiometry that has been born, catalysis method, the Reppe method of Rohm&Haas company improvement and Dow-Badische
The high pressure Reppe method that company improves.But Nickel tetracarbonyl. toxicity is high, totally unfavorable to labour protection, there is knot in the catalyst system and catalyzing after improvement
Carbon and conversion ratio, yield are relatively low.
Summary of the invention
In order to solve the problems referred to above, the present invention provides the system and method for a kind of acetylene carbonylation acrylic acid methyl ester., logical
The difference crossing recovered (distilled) temperature can be by product, and by-product and solvent separate, and reclaims carbon monoxide, organic solvent circulation again
Utilize, economize in raw materials, reduce cost.
An object of the present invention is to provide the system of a kind of acetylene carbonylation acrylic acid methyl ester., and this system includes: second
Alkynes dissolving tank, reactor, the first gas-liquid separator, the second gas-liquid separator, carbon monoxide extraction element and compressor.
Described acetylene dissolving tank is provided with acetylene entrance, non-polar organic solvent entrance and liquid outlet, and acetylene is passed through nonpolar
Organic solvent dissolves and reaches saturation.
Described reactor includes solvents for ethyne entrance, carbon monoxide gas inlet and gas outlet, and reactor is used for acetylene
Carbonylation.
Described first gas-liquid separator includes gas access, gas outlet and acrylic acid methyl ester. outlet.
Described second gas-liquid separator includes gas access and gas outlet.
Described acetylene dissolving tank liquid outlet is connected with described reactor solvents for ethyne entrance, described gas reactor outlet with
Described first gas-liquid separator gas access connects, described first gas-liquid separator gas outlet and described second gas-liquid separator
Gas access connects, and described second gas-liquid separator gas outlet is connected with described carbon monoxide extraction element gas access, institute
Stating carbon monoxide extraction element to be connected with described compressor, described compressor is with described reactor carbon monoxide gas inlet even
Connect.
In the present invention, described second gas-liquid separator includes liquid-phase outlet, described liquid-phase outlet and described acetylene dissolving tank
Non-polar organic solvent entrance connect, it is achieved the recycling of non-polar organic solvent.
In the present invention, described carbon monoxide extraction element is provided with offgas outlet, extracts the tail gas after carbon monoxide through tail gas
Reaction system is discharged in outlet.
In the present invention, described second gas-liquid separator is provided with byproduct discharge, and reaction gained by-product is by byproduct discharge
Derive.
It is a further object of the present invention to provide a kind of method utilizing said system acetylene carbonylation acrylic acid methyl ester., bag
Include following steps:
Acetylene dissolves, and acetylene is passed through non-polar organic solvent and dissolves and reach saturation；
Acetylene carbonylation, is passed through the carbon monoxide of pressurization beds and enters with methanol and dissolving acetylene in a solvent
Row reaction, reaction pressure is 0.3～10MPa, and reaction temperature is 150～250 DEG C, acetylene and mol ratio n of carbon monoxide
(C2H2): the mol ratio n (C of n (CO)=1:l～1:15, acetylene and methanol2H2):n(CH3OH)=1:l～1:10, acetylene is with molten
The mass ratio of agent is m (C2H2): m (solvent)=1:5～1:30, obtain containing acrylic acid methyl ester., unreacted acetylene, unreacted
Carbon monoxide, unreacted methanol, non-polar organic solvent, the gas-liquid mixture of by-product；
Gas-liquid first separation, by described gas-liquid mixture through cooling down laggard row gas-liquid separation, prepares acrylic acid methyl ester.；
Gas-liquid secondary separation, further separates gained gas after described gas-liquid first separation, obtains unreacted first
Alcohol, non-polar organic solvent containing a small amount of unreacted acetylene and by-product, unreacted methanol and containing a small amount of unreacted second
The non-polar organic solvent recycle and reuse of alkynes；
Extract carbon monoxide, the gas extraction carbon monoxide after described gas-liquid secondary separation, the carbon monoxide of described extraction
Utilize as carbonylation feedstock circulation, extract the tail gas after carbon monoxide and discharge reaction system.
This reaction is gas-liquid two-phase haptoreaction, does not has solid catalyst, thus avoid catalyst in reaction system
Loss.Acetylene is dissolved and reacts in a solvent, it is to avoid the danger that acetylene explodes under high-temperature and high-pressure conditions, and ensure bed
Temperature stabilization, will not occur beds temperature runaway.Can directly be recycled by the solvent that product is separated and recovered.
In the present invention, described process further comprises the steps of: carbon monoxide and pressurizes through compressor.
In the present invention, described non-polar organic solvent includes oxolane, 2-methyltetrahydrofuran, N-crassitude
One or more in ketone, acetone and acetylacetone,2,4-pentanedione.Non-polar organic solvent is not limited only to enumerated above several, this area
Technical staff can optionally choose.
In the present invention, the compound that catalyst is active metal described in described step acetylene carbonylation and auxiliary agent mixed
Close solution.
Acetylene is first dissolved in repressurization in non-polar organic solvent by the present invention, reduces direct compressed acetylene body and brings
Potential safety hazard；By the difference of recovered (distilled) temperature can be by acrylic acid methyl ester., by-product and solvent separate, it is to avoid increase
Solvent reclamation device；In system of the present invention, methanol after secondary gas-liquid separation and organic solvent can be again with, as
The raw material of acetylene dissolving tank, and the carbon monoxide that carbon monoxide extraction element obtains is back in reactor as raw material；This
Invent described system can cycling and reutilization organic solvent and carbon monoxide, economize in raw materials, reduce cost, system structure is simple,
Easy to operate.
Accompanying drawing explanation
Fig. 1 is the system structure schematic diagram of acetylene carbonylation acrylic acid methyl ester. of the present invention；
Fig. 2 is the schematic flow sheet of the method for acetylene carbonylation acrylic acid methyl ester. of the present invention.
Detailed description of the invention
Below in conjunction with drawings and Examples, the detailed description of the invention of the present invention is described in more details, in order to energy
The advantage being enough more fully understood that the solution of the present invention and various aspects thereof.But, specific embodiments described below and enforcement
Example is only descriptive purpose rather than limitation of the present invention.
As it is shown in figure 1, the present invention provides the system of a kind of acetylene carbonylation acrylic acid methyl ester., this system includes: acetylene
Dissolving tank 1, reactor the 2, first gas-liquid separator the 3, second gas-liquid separator 4, carbon monoxide extraction element 5 and compressor 6.
Acetylene dissolving tank 1 is provided with acetylene entrance, non-polar organic solvent entrance and liquid outlet.Acetylene is passed through nonpolar organic
Solvent dissolves and reaches saturation.
Reactor 2 is acetylene carbonylation apparatus, including solvents for ethyne entrance, carbon monoxide gas inlet and gas outlet.
Acetylene carbonyl is there is in the be dissolved with solvent of acetylene, carbon monoxide and the methanol importing reactor 2 of pressurization under the effect of catalyst
Glycosylation reaction.The non-polar organic solvent of dissolved acetylene undergoes phase transition along with temperature raises, and utilizes gasification latent heat to carry off acetylene and adds
The big calorimetric that hydrogen process is released, keeps stablizing of reaction bed temperature with this.
First gas-liquid separator 3 includes gas access, gas outlet and acrylic acid methyl ester. outlet.Gas-liquid separation gained
Acrylic acid methyl ester. is derived by acrylic acid methyl ester. outlet.
Second gas-liquid separator 4 includes gas access, gas outlet, liquid-phase outlet and byproduct discharge.Liquid-phase outlet with
The non-polar organic solvent entrance of acetylene dissolving tank 1 connects, it is achieved methanol and the recycling of non-polar organic solvent.Reaction
Gained by-product is derived by byproduct discharge.
Carbon monoxide extraction element 5 is provided with carbon monoxide outlet and offgas outlet, and the carbon monoxide of extraction is through carbon monoxide
Outlet imports compressor 6, extracts the tail gas after carbon monoxide and discharges reaction system through offgas outlet.
Compressor 6 is for the pressurization of carbon monoxide, compressor 6 coupled reaction device 2 carbon monoxide gas inlet.
Acetylene dissolving tank 1 liquid outlet is connected with reactor 2 solvents for ethyne entrance, reactor 2 gas outlet and the first gas-liquid
Separator 3 gas access connects, and the first gas-liquid separator 3 gas outlet is connected with the second gas-liquid separator 4 gas access, and second
Gas-liquid separator 4 gas outlet is connected with carbon monoxide extraction element 5 gas access, carbon monoxide extraction element 5 and compressor 6
Connecting, compressor 6 is connected with reactor 2 carbon monoxide gas inlet.
On the other hand, the present invention provides a kind of method utilizing said system acetylene carbonylation acrylic acid methyl ester., such as Fig. 2
Shown in, the method comprises the steps:
1, acetylene dissolves, and acetylene and non-polar organic solvent is passed through acetylene dissolving tank, makes acetylene nonpolar organic molten
Agent is dissolved and reaches saturation；
2, acetylene carbonylation, imports reactor after being pressurizeed by the non-polar organic solvent being dissolved with acetylene, by the one of pressurization
Carbonoxide is passed through beds and reacts with methanol and dissolving acetylene in a solvent, and reaction pressure is 0.3～10MPa,
Reaction temperature is 150～250 DEG C, acetylene and the mol ratio n (C of carbon monoxide2H2): n (CO)=1:l～1:15, acetylene and methanol
Mol ratio n (C2H2):n(CH3OH)=1:l-1:10, acetylene is m (C with the mass ratio of solvent2H2): m (solvent)=1:5～1:
30, obtain containing acrylic acid methyl ester., unreacted acetylene, unreacted carbon monoxide, unreacted methanol, nonpolar organic molten
Agent, the gas-liquid mixture of by-product；
3, gas-liquid first separation, described gas-liquid mixture imports described first gas-liquid separator, carries out after cooling down
Gas-liquid separation, prepares acrylic acid methyl ester.；
4, gas-liquid secondary separation, after described gas-liquid first separation, gained gas imports the second gas-liquid separator and further divides
From, obtain unreacted methanol, non-polar organic solvent containing a small amount of unreacted acetylene and by-product, unreacted methanol and
Non-polar organic solvent recycle and reuse containing a small amount of unreacted acetylene；
5, extracting carbon monoxide, the gas after described gas-liquid secondary separation imports carbon monoxide extraction element, the one of extraction
Carbonoxide utilizes as carbonylation feedstock circulation, extracts the tail gas after carbon monoxide and discharges reaction system；
6, the carbon monoxide extracted imports reactor after compressor pressurizes.
This reaction is gas-liquid two-phase haptoreaction, does not has solid catalyst, thus avoid catalyst in reaction system
Loss.Acetylene is dissolved and reacts in a solvent, it is to avoid the danger that acetylene explodes under high-temperature and high-pressure conditions, and ensure bed
Temperature stabilization, will not occur beds temperature runaway.Can be the most sharp by the first alcohol and solvent that product is separated and recovered
With, whole technique is simpler, easy to operate.
In the present invention, non-polar organic solvent include oxolane, 2-methyltetrahydrofuran, N-Methyl pyrrolidone, third
One or more in ketone and acetylacetone,2,4-pentanedione.Below it is only that non-polar organic solvent is enumerated, not as to nonpolar organic
The restriction of solvent.
In the present invention, the compound that catalyst is active metal and the mixing of auxiliary agent in described step acetylene carbonylation are molten
Liquid.
Below, by specific embodiment, the process of acetylene carbonylation acrylic acid methyl ester. of the present invention is illustrated.
Process embodiment
Embodiment 1:
Acetylene raw gas pressure is 0.5MPa, is passed through in the non-polar organic solvent containing methanol dissolving.
Organic solvent-acetone containing acetylene is forced into 5.5MPa by pump, delivers to reactor, then passes to 5.5MPa's
Carbon monoxide reacts, reaction temperature 200 DEG C, obtains containing acrylic acid methyl ester., unreacted acetylene, a unreacted oxidation
Carbon, unreacted methanol, non-polar organic solvent, the gas-liquid mixture of by-product.Catalyst in reactor is nickelous bromide, helps
Agent is copper bromide.
Reacted gas-liquid mixture temperature is 200 DEG C, enters the first gas-liquid separator and is cooled to 75 DEG C and obtains product third
E pioic acid methyl ester reclaims.
Gas after cooling enters the second gas-liquid separator and is again cooled to 20 DEG C and carries out gas-liquid separation, obtains methanol and molten
Agent recycle and reuse.
Gas after gas-liquid secondary separation enters carbon monoxide extraction element, and the carbon monoxide of extraction exports through carbon monoxide
Import compressor, after compressor pressurizes, import reactor as carbonylation raw material, extract the tail gas warp after carbon monoxide
Offgas outlet discharges reaction system.
Embodiment 2:
The method using embodiment 1 prepares acrylic acid methyl ester., and difference is: non-polar organic solvent replaces with tetrahydrochysene furan
Mutter；Reaction pressure is 1.5MPa；Reaction temperature is 240 DEG C.
Embodiment 3:
The method using embodiment 1 prepares acrylic acid methyl ester., and difference is: non-polar organic solvent replaces with levulinic
Ketone；Reaction pressure is 8.0MPa；Reaction temperature is 160 DEG C.
Concrete process conditions and non-polar organic solvent in above example is used to carry out acetylene carbonylation acrylic acid
Methyl ester, conversion of alkyne and acrylic acid methyl ester. selectivity result are as shown in table 1.
The conversion of alkyne of table 1 embodiment of the present invention and acrylic acid methyl ester. selectivity result
Using technique of the present invention to prepare acrylic acid methyl ester., response speed is fast, and conversion of alkyne is high, acrylic acid methyl ester.
Selectivity is high, and can avoid compressing the potential safety hazard that acetylene causes owing to first dissolving repressurization；Course of reaction will not fly
Temperature phenomenon.Additionally, carbon monoxide, methanol, organic solvent use and are respectively formed circulation line, effectively save cost in the present invention.
It should be noted that each embodiment above by reference to described by accompanying drawing is only in order to illustrate rather than restriction originally
The scope of invention, it will be understood by those within the art that, the most right
Amendment that the present invention is carried out or equivalent, all should contain within the scope of the present invention.Additionally, indication unless the context
Outward, the word occurred in the singular includes plural form, and vice versa.It addition, unless stated otherwise, then any embodiment
All or part of can use in conjunction with all or part of of any other embodiments.
Claims (8)
1. the system of an acetylene carbonylation acrylic acid methyl ester., it is characterised in that including: acetylene dissolving tank, reactor, first
Gas-liquid separator, the second gas-liquid separator, carbon monoxide extraction element and compressor,
Described acetylene dissolving tank is provided with acetylene entrance, non-polar organic solvent entrance and liquid outlet；
Described reactor includes solvents for ethyne entrance, carbon monoxide gas inlet and gas outlet；
Described first gas-liquid separator includes gas access, gas outlet and acrylic acid methyl ester. outlet；
Described second gas-liquid separator includes gas access and gas outlet；
Described acetylene dissolving tank liquid outlet is connected with described reactor solvents for ethyne entrance, and described gas reactor exports with described
First gas-liquid separator gas access connects, described first gas-liquid separator gas outlet and described second gas-liquid separator gas
Entrance connects, and described second gas-liquid separator gas outlet is connected with described carbon monoxide extraction element gas access, and described one
Carbonoxide extraction element is connected with described compressor, and described compressor is connected with described reactor carbon monoxide gas inlet.
System the most according to claim 1, it is characterised in that described second gas-liquid separator farther includes liquid phase and goes out
Mouthful, described liquid-phase outlet is connected with the non-polar organic solvent entrance of described acetylene dissolving tank.
System the most according to claim 1, it is characterised in that described carbon monoxide extraction element is provided with offgas outlet.
System the most according to claim 1, it is characterised in that described second gas-liquid separator is provided with byproduct discharge.
5. the method utilizing the arbitrary described system acetylene carbonylation acrylic acid methyl ester. of claim 1-4, it is characterised in that
Including step:
Acetylene dissolves, and acetylene is passed through non-polar organic solvent and dissolves and reach saturation；
Acetylene carbonylation, is passed through the carbon monoxide of pressurization beds and carries out instead with methanol and dissolving acetylene in a solvent
Should, reaction pressure is 0.3～10MPa, and reaction temperature is 150～250 DEG C, acetylene and the mol ratio n (C of carbon monoxide2H2):n
(CO) the mol ratio n (C of=1:l～1:15, acetylene and methanol2H2):n(CH3The quality of OH)=1:l-1:10, acetylene and solvent
Ratio is m (C2H2): m (solvent)=1:5～1:30, obtain containing acrylic acid methyl ester., unreacted acetylene, a unreacted oxidation
Carbon, unreacted methanol, non-polar organic solvent, the gas-liquid mixture of by-product；
Gas-liquid first separation, by described gas-liquid mixture through cooling down laggard row gas-liquid separation, prepares acrylic acid methyl ester.；
Gas-liquid secondary separation, further separates gained gas after described gas-liquid first separation, obtains unreacted methanol, contains
There are non-polar organic solvent and a by-product of a small amount of unreacted acetylene, unreacted methanol and non-containing a small amount of unreacted acetylene
Polar organic solvent recycle and reuse；
Extract carbon monoxide, the gas extraction carbon monoxide after described gas-liquid secondary separation, the carbon monoxide conduct of described extraction
Carbonylation feedstock circulation utilizes, and extracts the tail gas after carbon monoxide and discharges reaction system.
Method the most according to claim 5, it is characterised in that further comprise the steps of: carbon monoxide and pressurize through described compressor.
Method the most according to claim 5, it is characterised in that described non-polar organic solvent includes oxolane, 2-first
One or more in base oxolane, N-Methyl pyrrolidone, acetone or acetylacetone,2,4-pentanedione.
Method the most according to claim 5, it is characterised in that in described step acetylene carbonylation, described catalyst is
The compound of active metal and the mixed solution of auxiliary agent.
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| CN201610658918.4A CN106083582A (en) | 2016-08-11 | 2016-08-11 | A kind of system and method for acetylene carbonylation acrylic acid methyl ester. |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106045855A (en) * | 2016-08-11 | 2016-10-26 | 北京神雾环境能源科技集团股份有限公司 | System for preparing ethyl acrylate from acetylene, and method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2883418A (en) * | 1953-11-14 | 1959-04-21 | Basf Ag | Acrylic acid ester production |
| CN1068108A (en) * | 1991-05-31 | 1993-01-20 | 三共株式会社 | Be used to prepare the aza cyclo-butanone derivatives of carbapenem antibiotics |
| CN102190583A (en) * | 2010-03-08 | 2011-09-21 | 中国科学院成都有机化学有限公司 | Method for synthesizing low carbon alcohol ester of acrylic acid by catalyzing acetylene carbonyl through palladium-phosphine complex |
-
2016
- 2016-08-11 CN CN201610658918.4A patent/CN106083582A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2883418A (en) * | 1953-11-14 | 1959-04-21 | Basf Ag | Acrylic acid ester production |
| CN1068108A (en) * | 1991-05-31 | 1993-01-20 | 三共株式会社 | Be used to prepare the aza cyclo-butanone derivatives of carbapenem antibiotics |
| CN102190583A (en) * | 2010-03-08 | 2011-09-21 | 中国科学院成都有机化学有限公司 | Method for synthesizing low carbon alcohol ester of acrylic acid by catalyzing acetylene carbonyl through palladium-phosphine complex |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106045855A (en) * | 2016-08-11 | 2016-10-26 | 北京神雾环境能源科技集团股份有限公司 | System for preparing ethyl acrylate from acetylene, and method thereof |
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