CN105481716B - A kind of allyl acetonitrile synthetic process and system - Google Patents
A kind of allyl acetonitrile synthetic process and system Download PDFInfo
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- CN105481716B CN105481716B CN201510884375.3A CN201510884375A CN105481716B CN 105481716 B CN105481716 B CN 105481716B CN 201510884375 A CN201510884375 A CN 201510884375A CN 105481716 B CN105481716 B CN 105481716B
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- Prior art keywords
- butadiene
- allyl acetonitrile
- gas phase
- tower piece
- sent
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- CFEYBLWMNFZOPB-UHFFFAOYSA-N pent-4-enenitrile Chemical compound C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 28
- 230000008569 process Effects 0.000 title claims abstract description 21
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 125
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000007789 gas Substances 0.000 claims abstract description 23
- 239000012071 phase Substances 0.000 claims abstract description 22
- 239000007791 liquid phase Substances 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 10
- 238000000605 extraction Methods 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 230000005587 bubbling Effects 0.000 claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000002309 gasification Methods 0.000 claims description 6
- 230000008859 change Effects 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 238000005086 pumping Methods 0.000 claims description 2
- 230000006835 compression Effects 0.000 claims 1
- 238000007906 compression Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 238000012423 maintenance Methods 0.000 abstract description 6
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 238000009434 installation Methods 0.000 abstract description 2
- 238000004064 recycling Methods 0.000 abstract description 2
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005669 hydrocyanation reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A kind of allyl acetonitrile synthetic process, including step：1st, liquid phase butadiene feed is divided into gas-liquid two parts；2nd, by the gasifying section of butadiene described in step 1 and the gas phase butadiene of tower piece-rate system recovered overhead, compressor assembly pressurization is sent into after mixing；3rd, the gas phase butadiene after step 3 is pressurizeed is sent into reaction system with bubbling feeding manner under liquid；4th, reacting rear material is sent into tower piece-rate system through pump by reaction system, overhead extraction gas phase butadiene, as described in step 2, by the gasifying section of butadiene described in step 1 and the gas phase butadiene of tower piece-rate system recovered overhead, compressor assembly pressurization, bottom of towe extraction allyl acetonitrile product are sent into after mixing.The present invention improves hydrogen cyanide reaction efficiency, and the excess butadiene of original emptying discharge is carried out effective recycling, production cost is reduced, protects Environmental security.Solve the problems, such as mechanical seal present in blender installation, reduce maintenance shut-downs, improve manually-operated security.
Description
Technical field
The invention belongs to chemical production technical field, more particularly to a kind of allyl acetonitrile synthetic process and system.
Background technology
Adiponitrile (ADN, adiponitrile), the oily liquids of water white transparency, there is slight bitter taste, inflammable, molecular formula NC
(CH2)4CN, density 962kg/m3,1 DEG C of fusing point, 295 DEG C of boiling point.Toxic and corrosivity, is inhaled by oral cavity suction or skin
Receipts are responsible for being poisoned.Methanol, ethanol, chloroform are dissolved in, is insoluble in water, hexamethylene, ether, carbon disulfide, carbon tetrachloride.Oneself two
The main application of nitrile is production hexamethylene diamine, also has wide application in electronics, light industry and other organic synthesis fields in addition.
The process route of adiponitrile mainly has acrylonitrile (AN) Electrolytic Dimeric method, butadiene (BD) hydrocyanation process, adipic acid
(ADA) catalytic ammoniation method and caprolactam degraded Hydrolyze method again.The main technique of adiponitrile industrialized production is in the world today
Electrolytic Dimeric Acrylonitrile method and butadiene hydrocyanation process.The reaction of the direct hydrocyanation process production adiponitrile of butadiene includes level-one cyanogen
Three change, isomerization, two level cyaniding steps, this method use transition-metal catalyst, and two molecule hydrogen cyanide are introduced butadiene,
The complex compound of the transition metal such as catalyst generally use Ni, Rh, Ru.Wherein allyl acetonitrile (3PN) is its important intermediate, reaction
Equation is as follows：
Level-one cyaniding：
Isomerization：
Two level cyaniding：
General equation：CH2=CHCH=CH2+2HCN→NC(CH2)4CN+4H2
During level-one cyaniding production allyl acetonitrile (3PN), BD and the autohemagglutination that HCN often occurs in HCN reaction process,
Cause the blocking of pipeline and equipment, and HCN, as extremely toxic substance, maintenance shut-downs process can cause very big safety hidden to worker
Suffer from, it is therefore necessary to increase BD and HCN degree of mixings, improve HCN reaction rates, prevent from repairing caused leakage intoxication accident, together
When circulation and stress BD, save high cost of material, at the same met environment-friendly enterprise production requirement.
The content of the invention
During solving production allyl acetonitrile, butadiene in hydrogen cyanide reaction process with occurring hydrogen
The problem of autohemagglutination of cyanic acid, causes the blocking of pipeline and equipment, and maintenance shut-downs process can cause very big security risk to worker.
The concrete technical scheme of use is as follows：
A kind of allyl acetonitrile synthetic process, includes the following steps：
Step 1：Liquid phase butadiene feed is divided into two parts, a part is directly entered reaction system and is mixed with hydrogen cyanide,
Another part gasifies；
Step 2：By the gasifying section of butadiene described in step 1 and the gas phase butadiene of tower piece-rate system recovered overhead, mix
Compressor assembly pressurization is sent into after conjunction；
Step 3：Gas phase butadiene after step 2 is pressurizeed is sent into reaction system with bubbling feeding manner under liquid；
Step 4：Reacting rear material is sent into tower piece-rate system through pump by reaction system, and overhead extraction gas phase butadiene, such as walks
Described in rapid 2, the gasifying section of butadiene described in step 1 and the gas phase butadiene of tower piece-rate system recovered overhead are sent after mixing
Enter compressor assembly pressurization, bottom of towe extraction allyl acetonitrile product.
Liquid phase butadiene feed described in step 1 is divided into two parts, and liquid phase part is 3: 1 with gas phase portion mass ratio.
The gas phase butadiene of tower piece-rate system recovered overhead and the gasifying section of butadiene described in step 1 mix described in step 2
Need to handle by condenser system cooling before closing.Temperature is reduced to 5 DEG C~15 DEG C by condenser system.
Compressor assembly is pressurized to 20~50KpaG described in step 2.
A kind of allyl acetonitrile synthesis system, liquid phase butadiene feed end connect with reaction system and butadiene gasification system respectively
Connect, tower piece-rate system top exit is commonly connected to compressor assembly, compressor assembly outlet with the outlet of butadiene gasification system
Reaction system bottom is connected to, reaction system is equipped with catalyst inlet and hydrogen cyanide entrance, reaction system and tower piece-rate system
Connected by pumping, tower piece-rate system bottom is equipped with allyl acetonitrile products export.
Connected between tower piece-rate system and compressor assembly by condenser system.
The reaction system is reaction kettle, and the tower piece-rate system is rectifying column group.
The beneficial effects of the invention are as follows：Process of the present invention mixes two strands of butadiene materials of gas-liquid with hydrogen cyanide
Close, improve hydrogen cyanide reaction efficiency.The excess butadiene of original emptying discharge is carried out effective recycling, drop by reaction process
Low production cost, protects Environmental security.Reaction system is operated by bubbling and replaces conventional agitator married operation, is solved and is stirred
Mechanical seal problem present in device installation is mixed, ensures extremely toxic substance closed-loop operation as far as possible, maintenance shut-downs is reduced, improves people
The security of work operation.The invention of novel technological method meets the requirement of environmentally friendly production safety type enterprise.
Brief description of the drawings
Fig. 1 is allyl acetonitrile synthetic process process flow chart of the present invention
Marginal data：1st, reaction system, 2, tower piece-rate system, 3, compressor assembly, 4, condenser system, 5, pump, 6, fourth two
Alkene gasification system
A, liquid phase butadiene, B, catalyst, C, hydrogen cyanide, D, allyl acetonitrile
Embodiment
In order to make the technical means, the creative features, the aims and the efficiencies achieved by the present invention easy to understand, below it is right
The embodiment of the present invention is described further, but does not limit protection scope of the present invention, it is necessary to which explanation, is not being rushed
In the case of prominent, the feature in embodiment and embodiment in the invention can be mutually combined.
Allyl acetonitrile synthesis system of the present invention, connection structure are：Liquid phase butadiene A feed ends respectively with reaction system 1
Connected with butadiene gasification system 6,2 top exit of tower piece-rate system is commonly connected to compress with the outlet of butadiene gasification system 6
Machine system 3, the outlet of compressor assembly 3 are connected to 1 bottom of reaction system, and reaction system 1 is equipped with catalyst B entrances and hydrogen cyanide
C entrances, reaction system 1 are connected with tower piece-rate system 2 by pump 5, and 2 bottom of tower piece-rate system is equipped with allyl acetonitrile D products exports.Tower
Connected between piece-rate system 2 and compressor assembly 3 by condenser system 4.
The reaction system 1 is reaction kettle, and the tower piece-rate system 2 is rectifying column group.
Embodiment 1：
Liquid phase butadiene A charging rates are 8000kg/h, divide two parts to export, and a part is sent directly into instead with 6000kg/h
Answer system 1 to be mixed with hydrogen cyanide C, another part with 2000kg/h speed gasify, and with the gas phase of 2 recovered overhead of tower piece-rate system
Compressor assembly 3 is sent into after butadiene mixing and is forced into 20KpaG, and is sent into bubbling feeding manner under liquid in reaction system 1,
Reacting rear material is sent into tower piece-rate system 2, overhead extraction gas phase butadiene through pump 5 by reaction system 1, and condensed system 4 cools down
To 5 DEG C, such as abovementioned steps, which is sent into after being mixed with the gasifying section that liquid phase butadiene A feed inlets separate
Compressor assembly 3, finally produces allyl acetonitrile D products in 2 bottom of towe of tower piece-rate system.
Embodiment 2：
Liquid phase butadiene A charging rates are 12000kg/h, divide two parts to export, and a part is sent directly into 9000kg/h
Reaction system 1 is mixed with hydrogen cyanide C, another part with 3000kg/h speed gasify, and with the gas of 2 recovered overhead of tower piece-rate system
Compressor assembly 3 is sent into after the mixing of phase butadiene and is forced into 35KpaG, and reaction system 1 is sent into bubbling feeding manner under liquid
Interior, reacting rear material is sent into tower piece-rate system 2, overhead extraction gas phase butadiene through pump 5 by reaction system 1, and condensed system 4 drops
Temperature is to 10 DEG C, and such as abovementioned steps, which send after being mixed with the gasifying section that liquid phase butadiene A feed inlets separate
Enter compressor assembly 3, finally produce allyl acetonitrile D products in 2 bottom of towe of tower piece-rate system.
Embodiment 3：
Liquid phase butadiene A charging rates are 16000kg/h, divide two parts to export, and a part is sent directly into 12000kg/h
Reaction system 1 is mixed with hydrogen cyanide C, another part with 4000kg/h speed gasify, and with the gas of 2 recovered overhead of tower piece-rate system
Compressor assembly 3 is sent into after the mixing of phase butadiene and is forced into 50KpaG, and reaction system 1 is sent into bubbling feeding manner under liquid
Interior, reacting rear material is sent into tower piece-rate system 2, overhead extraction gas phase butadiene through pump 5 by reaction system 1, and condensed system 4 drops
Temperature is to 15 DEG C, and such as abovementioned steps, which send after being mixed with the gasifying section that liquid phase butadiene A feed inlets separate
Enter compressor assembly 3, finally produce allyl acetonitrile D products in 2 bottom of towe of tower piece-rate system.Comparative example：
Comparative example is stirred reaction system with blender, is produced allyl acetonitrile using traditional allyl acetonitrile production technology.
Above-mentioned is the embodiment 1-3 for being carried out using present invention process and system allyl acetonitrile production, and using conventional method into
The comparative example of row allyl acetonitrile production, discharge, maintenance period, cost of material consumption to its butadiene, pair of cost of labor consumption
Than as shown in Table 1.
1 embodiment of table and comparative example Contrast on effect table
By table 1 understand the present invention for conventional art have maintenance cost it is low, material equipment cost consumption is low, manually into
This consumption is few a little, and the discharge to butadiene is also considerably less than traditional handicraft.
Process and system of the present invention are described by specific embodiment.People in the art
Member can use for reference present disclosure and suitably change the links such as consersion unit, response parameter to realize corresponding other purposes, its
Correlation changes all without departing from present disclosure, all any modifications within the spirit and principle of the invention, made,
Equivalent substitution, improvement etc., should be included within the protection domain of the invention.
Claims (9)
1. a kind of allyl acetonitrile synthetic process, it is characterised in that include the following steps：
Step 1：Liquid phase butadiene feed is divided into two parts, a part is directly entered reaction system and is mixed with hydrogen cyanide, another
Gasify part；
Step 2：By the gas phase butadiene of the gasifying section of butadiene described in step 1 and tower piece-rate system recovered overhead, after mixing
It is sent into compressor assembly pressurization；
Step 3：Gas phase butadiene after step 2 is pressurizeed is sent into reaction system with bubbling feeding manner under liquid；
Step 4：Reacting rear material is sent into tower piece-rate system, overhead extraction gas phase butadiene, such as step 2 institute through pump by reaction system
State, by the gasifying section of butadiene described in step 1 and the gas phase butadiene of tower piece-rate system recovered overhead, compression is sent into after mixing
Machine system is pressurizeed, bottom of towe extraction allyl acetonitrile product.
A kind of 2. allyl acetonitrile synthetic process according to claim 1, it is characterised in that tower segregative line described in step 2
The gas phase butadiene of system recovered overhead needs to cool down by condenser system before mixing with the gasifying section of butadiene described in step 1
Processing.
3. a kind of allyl acetonitrile synthetic process according to claim 2, it is characterised in that by condenser system by temperature
It is reduced to 5 DEG C~15 DEG C.
A kind of 4. allyl acetonitrile synthetic process according to claim 1, it is characterised in that liquid phase fourth two described in step 1
Alkene charging is divided into two parts, and liquid phase part is 3: 1 with gas phase portion mass ratio.
A kind of 5. allyl acetonitrile synthetic process according to claim 1, it is characterised in that compressor system described in step 2
System is pressurized to 20~50KpaG.
A kind of 6. allyl acetonitrile synthesis system, it is characterised in that liquid phase butadiene feed end respectively with reaction system and butadiene gas
Change system connects, and tower piece-rate system top exit is commonly connected to compressor assembly, compressor with the outlet of butadiene gasification system
System outlet is connected to reaction system bottom, and reaction system is equipped with catalyst inlet and hydrogen cyanide entrance, reaction system and tower
Piece-rate system is connected by pumping, and tower piece-rate system bottom is equipped with allyl acetonitrile products export.
7. a kind of allyl acetonitrile synthesis system according to claim 6, it is characterised in that tower piece-rate system and compressor assembly
Between connected by condenser system.
8. a kind of allyl acetonitrile synthesis system according to claim 6, it is characterised in that the reaction system is reaction kettle.
9. a kind of allyl acetonitrile synthesis system according to claim 6, it is characterised in that the tower piece-rate system is rectifying column
Group.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510884375.3A CN105481716B (en) | 2015-12-04 | 2015-12-04 | A kind of allyl acetonitrile synthetic process and system |
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| CN201510884375.3A CN105481716B (en) | 2015-12-04 | 2015-12-04 | A kind of allyl acetonitrile synthetic process and system |
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| CN105481716B true CN105481716B (en) | 2018-04-27 |
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Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004004720A1 (en) * | 2004-01-29 | 2005-08-18 | Basf Ag | Process for the preparation of 3-pentenenitrile |
| DE102004004673A1 (en) * | 2004-01-29 | 2005-08-18 | Basf Ag | Process for the hydrocyanation of butadiene |
| CN205275496U (en) * | 2015-12-04 | 2016-06-01 | 中国天辰工程有限公司 | Allyl acetonitrile synthesis system |
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