CN117658855A - Adiponitrile synthesis method and synthesis device - Google Patents
Adiponitrile synthesis method and synthesis device Download PDFInfo
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- CN117658855A CN117658855A CN202211009970.9A CN202211009970A CN117658855A CN 117658855 A CN117658855 A CN 117658855A CN 202211009970 A CN202211009970 A CN 202211009970A CN 117658855 A CN117658855 A CN 117658855A
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- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 16
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 16
- 238000001308 synthesis method Methods 0.000 title claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 150
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 91
- 238000000926 separation method Methods 0.000 claims abstract description 76
- 239000000047 product Substances 0.000 claims abstract description 57
- 239000002994 raw material Substances 0.000 claims abstract description 56
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000004176 ammonification Methods 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 31
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 29
- 239000007788 liquid Substances 0.000 claims abstract description 27
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 26
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 22
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 13
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000011084 recovery Methods 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 230000018044 dehydration Effects 0.000 claims description 30
- 238000006297 dehydration reaction Methods 0.000 claims description 30
- 238000007670 refining Methods 0.000 claims description 30
- 238000009833 condensation Methods 0.000 claims description 28
- 230000005494 condensation Effects 0.000 claims description 28
- 238000010992 reflux Methods 0.000 claims description 28
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 22
- 239000012071 phase Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 239000000295 fuel oil Substances 0.000 claims description 15
- 239000003921 oil Substances 0.000 claims description 15
- 239000007789 gas Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 230000002194 synthesizing effect Effects 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 9
- 239000002351 wastewater Substances 0.000 claims description 9
- 239000007791 liquid phase Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000002912 waste gas Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 238000004891 communication Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 6
- 238000010924 continuous production Methods 0.000 abstract description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 14
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000005204 segregation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 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
- C07C253/22—Preparation of carboxylic acid nitriles by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
- B01D3/146—Multiple effect distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The application discloses a synthesis method and a synthesis device of adiponitrile, wherein the synthesis method comprises a reaction stage, a heat recovery stage and a separation stage; the reaction stage comprises: respectively introducing a raw material I containing dimethyl adipate a and a raw material II containing ammonia a into an ammonification reactor, and contacting with a catalyst to react to obtain an ammonification reaction product containing adiponitrile; the heat recovery stage comprises: respectively carrying out heat exchange treatment on the raw materials I and II by utilizing the ammonification reaction product; the separation stage: and (3) carrying out gas-liquid separation and multistage rectification treatment on the ammoniation reaction product after heat exchange to sequentially obtain methanol, ammonia b, adiponitrile, indole, pyrrole and dimethyl adipate b. The method can be used for producing adiponitrile, has continuous process and high product purity, recovers unreacted raw materials, reduces cost, can produce byproducts such as methanol, pyrrole, indole and the like, has good economical efficiency, and is suitable for industrial large-scale continuous production.
Description
Technical Field
The application relates to a synthesis method and a synthesis device of adiponitrile, and belongs to the technical field of chemical industry.
Background
Hexamethylenediamine is a key chemical intermediate monomer for synthesizing high-performance nylon 66, and is also used for polyamide synthesis and widely applied to industrial production as a resin curing agent and an agricultural and mining flotation agent. According to different raw materials, the synthesis method of hexamethylenediamine mainly comprises three steps: butadiene, acrylonitrile and adipic acid.
Butadiene is used as raw material, and is reacted to synthesize adiponitrile, and then hydrogenated to synthesize hexamethylenediamine. The method has low cost and high product quality, but has extremely high requirements on equipment and operation management, the catalyst preparation difficulty is high, and the technology is held by developed countries for a long time, so that a technical barrier is formed.
The acrylonitrile method synthesizes adiponitrile through the electrolytic dimerization of acrylonitrile, and then synthesizing hexamethylenediamine through hydrogenation. The method adopts highly toxic raw materials, has high control difficulty and high safety risk, and is eliminated.
Adipic acid is used as raw material, adiponitrile is prepared by ammonification and dehydration, and hexamethylenediamine is synthesized by hydrogenation. The method is relatively mature, but the process has high energy consumption, equipment is easy to be crosslinked and corroded, and meanwhile, the fluctuation of the device caused by the influence of raw materials is large.
In addition to the above three processes, the process for producing hexamethylenediamine by the caprolactam method has been developed by eastern japan company in the 60 th century. The method takes caprolactam as a raw material, prepares 6-aminocapronitrile by catalytic ammonolysis and dehydration, and prepares hexamethylenediamine by hydrogenation. The method cannot be popularized on a large scale due to high cost of raw caprolactam, and production is stopped in 1989.
Disclosure of Invention
The invention provides a method for synthesizing adiponitrile, which is characterized in that adiponitrile is generated by ammonification of dimethyl adipate, continuous production of adiponitrile and separation of byproducts such as methanol, indole, pyrrole and the like are realized by gravity decantation, segregation rectification and sequence separation, the process is continuous, the flow has good economy, and the method is suitable for industrialized large-scale continuous production.
In one aspect of the present application, a method for synthesizing adiponitrile is provided, the method comprising a reaction stage, a heat recovery stage, and a separation stage;
the reaction stage comprises: respectively introducing a raw material I containing dimethyl adipate a and a raw material II containing ammonia a into an ammonification reactor, and contacting with a catalyst to react to obtain an ammonification reaction product containing adiponitrile;
the heat recovery stage comprises: respectively carrying out heat exchange treatment on the raw materials I and II by utilizing the ammonification reaction product;
the separation stage: and (3) carrying out gas-liquid separation and multistage rectification treatment on the ammoniation reaction product after heat exchange to sequentially obtain methanol, ammonia b, adiponitrile, indole, pyrrole and dimethyl adipate b.
Alternatively, the reaction conditions are: the reaction temperature is 100-500 ℃; the reaction pressure is 0-5 MPa.
Alternatively, the reaction temperature is independently selected from any value of 100 ℃, 300 ℃, 330 ℃, 350 ℃, 500 ℃ or a range of values between any two points.
Alternatively, the reaction pressure is independently selected from any value of 0MPa, 0.02MPa, 1MPa, 2MPa, 3MPa, 4MPa, 5MPa or a range of values between any two of the above.
Optionally, in the reaction stage, the feedstock I further comprises recycled dimethyl adipate b;
the raw material II also comprises circulating ammonia gas b.
Optionally, the reaction stage comprises the steps of exchanging heat between a raw material I containing dimethyl adipate a and recycled dimethyl adipate b and a first strand of ammonification reaction product, then heating to a reaction temperature, and introducing the raw material I into the ammonification reactor;
and (3) exchanging heat between the raw material II containing the ammonia gas a and the recycled ammonia gas b and a second strand of ammonification reaction product, then heating to the reaction temperature, and introducing the mixture into the ammonification reactor.
In the application, the ammoniation reaction product is subjected to heat exchange with the dimethyl adipate raw material and ammonia gas respectively in two streams.
Optionally, the gas-liquid separation includes: and cooling and flashing the ammoniated reaction product after heat exchange to separate ammonia-containing waste gas and condensate, wherein the ammonia-containing waste gas is non-condensable combustible gas impurities.
Optionally, the temperature of the ammoniation reaction product after heat exchange is 50-100 ℃;
the cooling temperature is-30-100 ℃;
the flash pressure is 0-10 BarG.
Alternatively, the temperature of the ammoniated reaction product after heat exchange is independently selected from any value of 50 ℃, 70 ℃, 90 ℃, 92 ℃, 94 ℃, 100 ℃ or a range of values between any two points.
Alternatively, the temperature of the cooling treatment is independently selected from any value of-30 ℃, -10 ℃, 30 ℃, 50 ℃, 70 ℃, 90 ℃, 100 ℃ or a range of values between any two points of the foregoing.
Alternatively, the pressure of the flash treatment is independently selected from any of 0BarG, 1BarG, 3BarG, 5BarG, 7BarG, 9BarG, 10BarG, or a range of values between any two of the foregoing.
Optionally, the multistage rectification process comprises:
introducing the condensate into a methanol tower for fractional condensation and rectification, obtaining ammonia gas b at the tower top, obtaining methanol at the tower side and obtaining distillate I at the tower bottom; wherein, the top of the methanol tower adopts a dephlegmator, the top of the methanol tower extracts gaseous distillate ammonia b as circulating ammonia for recycling, and the side line extracts methanol byproducts;
introducing the distillate I into a light component removal tower I for rectification complete condensation separation a, obtaining cyclopentanone water solution at the tower top and obtaining water-containing materials at the tower bottom;
introducing the water-containing material into a dehydration tower for rectification complete condensation separation b, obtaining wastewater at the top of the tower and distillate II at the bottom of the tower, and realizing wastewater removal;
introducing the distillate II into a product tower for rectification complete condensation separation c, obtaining a mixture I containing dimethyl adipate at the tower top and adiponitrile at the tower bottom, and removing light impurities of the product to obtain a qualified product;
introducing the mixture I containing the dimethyl adipate into a heavy oil removal tower for rectification complete condensation separation d, obtaining heavy oil removal from the tower top, and obtaining indole from the tower bottom to realize heavy oil removal;
the heavy oil is removed and then is led into a light oil removal tower II to carry out rectification complete condensation separation e, pyrrole is obtained at the top of the tower, and a mixture II containing dimethyl adipate is obtained at the bottom of the tower, so that the light oil is removed;
and introducing the mixture II of the dimethyl adipate into a refining tower for rectification complete condensation separation f, obtaining dimethyl adipate b at the bottom of the refining tower, wherein the dimethyl adipate b is an unreacted raw material, and can be recycled after being pressurized.
Optionally, the ammonia gas b and the dimethyl adipate b are recycled.
Optionally, the cyclopentanone aqueous solution is phase separated by a decanter to obtain an oil phase and an aqueous phase.
Optionally, the temperature of the top of the methanol tower is-40-60 ℃, and the pressure of the top of the methanol tower is 1-400 kPaA.
Optionally, the temperature of the top of the light component removal tower I is 20-120 ℃, and the pressure of the top of the light component removal tower I is 1-400 kPaA.
Optionally, the temperature of the top of the dehydration tower is 10-80 ℃, and the pressure of the top of the dehydration tower is 1-400 kPaA.
Optionally, the tower top temperature of the product tower is 30-160 ℃, and the tower top pressure is 0.5-200 kPaA.
Optionally, the top temperature of the de-weight tower is 100-180 ℃, and the top pressure of the de-weight tower is 1-200 kPaA.
Optionally, the temperature of the top of the light component removal tower II is 50-180 ℃, and the pressure of the top of the tower is 1-200 kPaA.
Optionally, the temperature of the top of the refining tower is 50-180 ℃, and the pressure of the top of the refining tower is 1-200 kPaA.
Optionally, the overhead temperature of the methanol column is independently selected from any value of-40 ℃, -22 ℃, 0 ℃, 20 ℃, 40 ℃, 60 ℃ or a range value between any two points; the overhead pressure of the methanol column is independently selected from any value of 1kPaA, 50kPaA, 100kPaA, 115kPaA, 150kPaA, 200kPaA, 250kPaA, 300kPaA, 350kPaA, 400kPaA or a range of values between any two of the foregoing.
Optionally, the top temperature of the light component removal column I is independently selected from any value of 20 ℃, 40 ℃, 60 ℃, 80 ℃, 97 ℃ and 120 ℃ or a range value between any two points; the overhead pressure of the light ends column I is independently selected from any value of 1kPaA, 50kPaA, 110kPaA, 150kPaA, 200kPaA, 250kPaA, 300kPaA, 350kPaA, 400kPaA or a range of values between any two points.
Optionally, the top temperature of the dehydration column is independently selected from any value of 10 ℃, 30 ℃, 46 ℃, 60 ℃, 80 ℃ or a range value between any two points; the top pressure of the dehydration tower is independently selected from any value of 1kPaA, 10kPaA, 50kPaA, 110kPaA, 150kPaA, 200kPaA, 250kPaA, 300kPaA, 350kPaA and 400kPaA or a range value between any two points.
Optionally, the overhead temperature of the product column is independently selected from any value or range of values between any two of 30 ℃, 60 ℃, 82 ℃, 100 ℃, 120 ℃, 140 ℃, 160 ℃; the overhead pressure of the product column is independently selected from any of 0.5kPaA, 2kPaA, 10kPaA, 50kPaA, 110kPaA, 150kPaA, 200kPaA, or a range of values between any two of the foregoing.
Optionally, the top temperature of the de-weight column is independently selected from any value of 100 ℃, 116 ℃, 120 ℃, 140 ℃, 160 ℃, 180 ℃ or a range value between any two points; the top pressure of the heavy-duty removal column is independently selected from any value of 1kPaA, 10kPaA, 50kPaA, 110kPaA, 150kPaA, 200kPaA or a range of values between any two points.
Optionally, the top temperature of the light ends removal column II is independently selected from any value of 50 ℃, 80 ℃, 101 ℃, 120 ℃, 137 ℃, 160 ℃, 180 ℃ or a range value between any two points; the overhead pressure of the light ends column II is independently selected from any value of 1kPaA, 5kPaA, 40kPaA, 110kPaA, 150kPaA, 200kPaA or a range of values between any two points.
Optionally, the top temperature of the refining column is independently selected from any value of 50 ℃, 80 ℃, 109 ℃, 128 ℃, 160 ℃, 180 ℃ or a range value between any two points; the top pressure of the refining tower is independently selected from any value of 1kPaA, 10kPaA, 50kPaA, 100kPaA, 150kPaA and 200kPaA or a range value between any two points.
In another aspect of the application, a synthesis device of adiponitrile is provided, the synthesis device comprises a reaction unit, a heat recovery unit and a separation unit, wherein the heat recovery unit is respectively communicated with the reaction unit and the separation unit through pipelines;
the reaction unit comprises a first preheater, a second preheater and an ammonification reactor, wherein the first preheater and the second preheater are respectively communicated with the ammonification reactor;
the heat recovery unit comprises a first heat exchanger and a second heat exchanger; the first heat exchanger is respectively communicated with the first preheater and the ammonification reactor, and the second heat exchanger is respectively communicated with the second preheater and the ammonification reactor;
the separation unit comprises a gas-liquid separation module, a methanol tower, a light component removal tower I, a dehydration tower, a product tower, a heavy component removal tower, a light component removal tower II and a refining tower which are sequentially communicated;
the first heat exchanger and the second heat exchanger are respectively communicated with the gas-liquid separation module;
the top of the methanol tower is provided with a gas phase outlet II which is communicated with the second heat exchanger, and the side wall of the methanol tower is also provided with a methanol outlet;
the bottom of the refining tower is provided with a dimethyl adipate outlet which is communicated with the first heat exchanger;
wherein the alcohol tower, the light component removing tower I, the dehydrating tower, the product tower, the heavy component removing tower, the light component removing tower II and the refining tower are all rectifying towers.
Optionally, the reflux ratio of the methanol tower is 0.1-50, and the theoretical plate number is 5-40.
Optionally, the reflux ratio of the light component removal tower I is 1-150, and the theoretical plate number is 5-80.
Optionally, the tower reflux ratio of the dehydration tower is 0.1-40, and the theoretical plate number is 5-80.
Optionally, the reflux ratio of the product tower is 0.1-40, and the theoretical plate number is 5-80.
Optionally, the reflux ratio of the de-weight tower is 0.1-40, and the theoretical plate number is 5-80.
Optionally, the reflux ratio of the light component removal tower II is 0.1-40, and the theoretical plate number is 5-80.
Optionally, the reflux ratio of the refining tower is 0.1-40, and the theoretical plate number is 5-80.
Optionally, the reflux ratio of the methanol tower is independently selected from any value of 0.1, 8, 20, 30, 40 and 50 or a range value between any two points; the top temperature of the methanol tower is independently selected from any value of 5, 10, 15, 20, 25, 30, 35 and 40 or a range value between any two points.
Optionally, the reflux ratio of the light component removal tower I is independently selected from any value of 1, 40, 80, 110 and 150 or a range value between any two points; the theoretical plate number of the light component removal tower I is independently selected from any value of 5, 15, 30, 45, 60 and 80 or a range value between any two points.
Optionally, the reflux ratio of the dehydration tower is independently selected from any value of 0.1, 1, 10, 20, 30 and 40 or a range value between any two points; the theoretical plate number of the dehydration tower is independently selected from any value of 5, 15, 30, 45, 60 and 80 or a range value between any two points.
Optionally, the reflux ratio of the product column is independently selected from any of 0.1, 3, 13, 20, 30, 40 or a range between any two points; the theoretical plate number of the product tower is independently selected from any value of 5, 20, 40, 60 and 80 or a range value between any two points.
Optionally, the reflux ratio of the heavy-duty removal tower is independently selected from any value of 0.1, 1, 5, 13, 20, 30 and 40 or a range value between any two points; the theoretical plate number of the heavy-removal tower is independently selected from any value of 5, 15, 30, 40, 45, 60 and 80 or a range value between any two points.
Optionally, the reflux ratio of the light ends column II is independently selected from any value of 0.1, 3, 5, 13, 20, 30 and 40 or a range value between any two points; the theoretical plate number of the light component removal tower II is independently selected from any value of 5, 15, 30, 40, 50, 60 and 80 or a range value between any two points.
Optionally, the reflux ratio of the refining tower is independently selected from any value of 0.1, 3, 5, 10, 20, 30 and 40 or a range value between any two points; the theoretical plate number of the refining tower is independently selected from any value of 5, 15, 30, 40, 50, 60 and 80 or a range value between any two points.
Optionally, the gas-liquid separation module is provided with an ammonification reaction product inlet, a gas phase outlet I and a liquid phase outlet I;
the first heat exchanger and the second heat exchanger are respectively communicated with the ammonification reaction product inlet;
the liquid phase outlet I is communicated with the tower side wall of the methanol tower;
the bottom of the methanol tower is communicated with the tower side wall of the light component removal tower I;
the bottom of the light component removal tower I is communicated with the side wall of the dehydration tower;
the bottom of the dehydration tower is communicated with the tower side wall of the product tower;
the top of the product tower is communicated with the tower side wall of the heavy-removal tower;
the top of the heavy-removal tower is communicated with the tower side wall of the light-removal tower II;
the bottom of the light component removal tower II is communicated with the tower side wall of the refining tower.
Optionally, a cyclopentanone water solution outlet is arranged at the top of the light component removal tower I;
an adiponitrile outlet is arranged at the bottom of the product tower;
an indole outlet is arranged at the bottom of the heavy-duty removal tower;
and an pyrrole outlet is arranged at the top of the light component removing tower II.
Optionally, the gas-liquid separation module comprises a condenser and a flash tank which are connected in sequence; the flash tank is provided with a gas phase outlet I and a liquid phase outlet I, and the condenser is provided with an ammonification reaction product inlet.
Optionally, the synthesis device further comprises an ammonia recycle compressor;
the ammonia circulating compressor is respectively communicated with the gas phase outlet II and the second heat exchanger.
Optionally, the synthesis device further comprises a decanter;
the decanter is in communication with the cyclopentanone aqueous solution outlet.
As a specific embodiment, the synthesizing device in the application is shown in fig. 1 and 2, and comprises the following components:
a raw material heat exchanger 1, an ammonia gas heat exchanger 2, a raw material preheater 3, an ammonia gas preheater 4, a reactor 5, a product condenser 6, a gas-liquid separation tank 7, a condensate pump 8, a methanol column 9, an ammonia recycle compressor 10, a light component removal column feed pump 11, a light component removal column 12, a decanter 13, a dehydration column 14, a product column feed pump 15, a product column 16, a heavy component removal column feed pump 17, a heavy component removal column 18, a light component removal column feed pump 19, a light component removal column 20, a refining column 21 and a recycle pump 22.
The method for synthesizing adiponitrile by using the device comprises the following steps:
(1) Fresh dimethyl adipate and recycled dimethyl adipate are mixed, heat exchange is carried out between the fresh dimethyl adipate and a reaction product in a raw material heat exchanger 1, and then the mixture is heated to a reaction temperature in a raw material preheater 3;
(2) Mixing fresh ammonia gas with circulating ammonia gas, exchanging heat with a reaction product in an ammonia gas heat exchanger 2, heating to a reaction temperature in an ammonia gas preheater 4, sending the mixture and dimethyl adipate into a reactor 5, and carrying out catalytic reaction to obtain an ammonification reaction product;
(3) The ammoniated product is separated into two strands and exchanges heat with dimethyl adipate and ammonia in a raw material heat exchanger 1 and an ammonia heat exchanger 3 respectively;
(4) The ammoniated products after heat exchange are combined and enter a product condenser 6 to form gas-liquid two phases at low temperature, gas-liquid separation is realized in a gas-liquid separation tank 7, ammonia-containing waste gas and condensate are separated, and the condensate is pressurized by a condensate pump 8 and then sent to a methanol tower 9 for separation;
(5) The methanol tower 9 adopts fractional condensation rectification, side line extraction is carried out, non-condensable ammonia gas is extracted from the tower top, the non-condensable ammonia gas is circularly used after being pressurized by the ammonia recycle compressor 10, methanol with purity of more than 99% is extracted from the side line, and bottom distillate is sent to the light component removal tower 12 for separation after being pressurized by the light component removal tower feeding pump 11;
(6) The light component removal tower 12 adopts rectification complete condensation separation, cyclopentanone water solution is obtained at the tower top, combustible oil phase waste liquid and waste water are obtained after layering in the decanter 13, and water-containing materials obtained at the tower bottom are sent to the dehydration tower 14 for separation;
(7) The dehydration tower 14 adopts rectification complete condensation separation, waste water is obtained at the tower top, and the bottom distillate is sent to the product tower 16 for separation after being pressurized by the product tower feed pump 15;
(8) The product tower 16 adopts rectification complete condensation separation, a qualified adiponitrile product is obtained at the bottom of the tower, a mixture of byproducts and unreacted dimethyl adipate is obtained at the top of the tower, and the mixture is sent to a de-weight tower 18 for separation after being pressurized by a de-weight tower feed pump 17;
(9) The heavy oil removal tower 18 adopts rectification total condensation separation, heavy oil mainly containing indole is obtained at the bottom of the tower, heavy oil removal is obtained at the top of the tower, and the heavy oil is pressurized by the light oil removal tower feeding pump 19 and then sent to the light oil removal tower 20 for separation;
(10) The light component removal tower 20 adopts rectification complete condensation separation, the light component mainly containing pyrrole is obtained at the tower top, unreacted crude dimethyl adipate is obtained at the tower bottom, and the unreacted raw material is recycled by the refining tower 21;
(11) The refining tower 21 adopts rectification complete condensation separation, light impurity oil is obtained at the top of the tower, circulating dimethyl adipate raw material with purity higher than 99% is obtained at the bottom of the tower, and the raw material is pressurized by the circulating pump 22 and then returned to the inlet of the raw material heat exchanger 1 for recycling.
The beneficial effects that this application can produce include:
the application discloses a method for synthesizing adiponitrile, which adopts the cyclic operation of raw material preheating, reaction, gas phase separation, gravity decantation, segregation rectification, sequence separation and raw material recycling in the process flow, has continuous process and high product purity, recovers unreacted raw materials, reduces the cost, can produce products such as methanol, pyrrole, indole and the like as byproducts, has good economy, and is suitable for industrial large-scale continuous production.
Drawings
FIG. 1 is a schematic representation of the synthesis and preliminary separation of adiponitrile in the examples of the present application.
FIG. 2 is a schematic diagram of the separation and purification of adiponitrile by the method of synthesis in the examples of the present application.
Wherein,
1. a raw material heat exchanger; 2. an ammonia gas heat exchanger; 3. a raw material preheater; 4. an ammonia preheater; 5. A reactor; 6. a product condenser; 7. a gas-liquid separation tank; 8. a condensate pump; 9. a methanol tower; 10. A recycle compressor is installed; 11. a light component removal tower feed pump; 12. a light component removing tower; 13. a decanter; 14. a dehydration tower; 15. a product column feed pump; 16. a product tower; 17. a heavy-removal tower feed pump; 18. a weight removing tower; 19. a light component removal tower feed pump; 20. a light component removing tower; 21. a refining tower; 22. and a circulation pump.
Detailed Description
The present application is described in detail below with reference to examples, but the present application is not limited to these examples.
Unless otherwise indicated, both the starting materials and the catalysts in the examples of the present application were purchased commercially.
Example 1
As shown in fig. 1 and 2, an adiponitrile synthesis device comprises the following components: a raw material heat exchanger 1, an ammonia gas heat exchanger 2, a raw material preheater 3, an ammonia gas preheater 4, a reactor 5, a product condenser 6, a gas-liquid separation tank 7, a condensate pump 8, a methanol column 9, an ammonia recycle compressor 10, a light component removal column feed pump 11, a light component removal column 12, a decanter 13, a dehydration column 14, a product column feed pump 15, a product column 16, a heavy component removal column feed pump 17, a heavy component removal column 18, a light component removal column feed pump 19, a light component removal column 20, a refining column 21 and a recycle pump 22.
The inlet ends of the raw material heat exchanger 1, the raw material preheater 3 and the reactor 5 are sequentially communicated; the inlet ends of the ammonia gas heat exchanger 2, the ammonia gas preheater 4 and the reactor 5 are sequentially communicated; the outlet end of the reactor 5 is respectively communicated with the raw material heat exchanger 1 and the ammonia gas heat exchanger 2.
The raw material heat exchanger 1 and the ammonia gas heat exchanger 2 are communicated with a product condenser 6, and the product condenser 6 is communicated with the side wall of a gas-liquid separation tank 7; the bottom of the gas-liquid separation tank 7 is provided with an ammonia-containing wastewater outlet, and the bottom outlet is communicated with the side wall of the methanol tower 9 through a condensate pump 8; the side wall of the methanol tower 9 is also provided with a methanol outlet, the tower top is provided with a gas phase outlet, the gas phase outlet is communicated with the ammonia gas heat exchanger 2 through the ammonia circulating compressor 10, and the tower bottom of the methanol tower 9 is communicated with the side wall of the light component removal tower 12 through the light component removal tower feeding pump 11; the top of the light component removal tower 12 is provided with a cyclopentanone water solution outlet which is communicated with a decanter 13; the bottom of the light component removal tower 12 is communicated with the side wall of the light component removal tower 14; the top of the dehydration tower 14 is provided with a wastewater outlet, and the bottom of the dehydration tower is communicated with a product tower 16 through a product tower feed pump 15; the bottom of the product tower 16 is provided with an adiponitrile outlet, and the top of the product tower is communicated with a de-weight tower 18 through a de-weight tower feeding pump 17; an indole outlet is arranged at the bottom of the heavy-removal tower 18, and the top of the tower is communicated with a light-removal tower 20 through a light-removal tower feed pump 19; the top of the light component removal tower 20 is provided with a pyrrole outlet, the bottom of the tower is communicated with the refining tower 21, the top of the refining tower 21 is provided with a light impurity oil outlet, and the bottom of the tower is communicated with the raw material heat exchanger 1 through a circulating pump 22.
Example 2
By using the synthesis apparatus described in example 1, fresh dimethyl adipate and recycled dimethyl adipate were mixed and then heat-exchanged with the reaction product to 245 ℃ in a raw material preheater 1# and then heated to 330 ℃ in a raw material preheater 3 # and simultaneously fresh ammonia gas and recycled ammonia gas were mixed, heat-exchanged with the reaction product to 335 ℃ in an ammonia gas preheater 2# and then heated to 350 ℃ in an ammonia gas preheater 4 # and then fed into a reactor 5 (pressure of 0.02 MPa) containing a platinum metal-loaded molecular sieve catalyst together with dimethyl adipate, and an ammonified reaction product was obtained by catalytic reaction. The ammoniated product at 350 ℃ flows out of the reactor 5 and is divided into two parts, wherein 28.6% of the ammoniated product is cooled to 94 ℃ after being subjected to heat exchange with ammonia in the No. 1 ammonia preheater 2, the rest of the ammoniated product is cooled to 92 ℃ after being subjected to heat exchange with dimethyl adipate in the No. 1 raw material preheater 1, the cooled ammoniated product is combined and enters the product condenser 6 to be cooled to-10 ℃, gas-liquid two phases are formed at low temperature, gas-liquid separation is realized in the gas-liquid separation tank 7, ammonia-containing waste gas and condensate are separated, and the operating pressure of the gas-liquid separation tank 7 is 1.15BarA. The condensate is sent to a methanol tower 9 for separation after being pressurized by a condensate pump 8. The methanol tower 9 adopts fractional condensation rectification, sets 20 theoretical plates, has reflux ratio of 8, has tower top temperature of-22 ℃ and operating pressure of 115kPaA, and extracts methanol from the side line of the 3 rd theoretical plate. Non-condensable ammonia gas with ammonia content of more than 99.6% mol is extracted from the top of the methanol tower 9, the non-condensable ammonia gas is pressurized by an ammonia recycle compressor 10 and recycled, methanol with purity of 99.2% mol is extracted from the side line, and the bottom distillate is pressurized by a light component removal tower feeding pump 11 and then sent to a light component removal tower 12 for separation. The light component removal tower 12 adopts rectification complete condensation separation, 30 theoretical plates are arranged, the reflux ratio is 110, the tower top temperature is 97 ℃, and the operating pressure is 110kPaA. The cyclopentanone aqueous solution is obtained at the top of the light component removal tower 12, combustible oil phase waste liquid and waste water are obtained after layering in a decanter 13, and water-containing materials obtained at the bottom of the tower are sent to the dehydration tower 14 for separation. The dehydration tower 14 adopts rectification complete condensation separation, 30 theoretical plates are arranged, the reflux ratio is 1, the tower top temperature is 46 ℃, and the operating pressure is 10kPaA. The waste water is obtained from the top of the dehydration column 14, and the bottoms are sent to a product column 16 for separation after being pressurized by a product column feed pump 15. The product column 16 adopts rectification complete condensation separation, 20 theoretical plates are arranged, the reflux ratio is 3, the temperature of the column top is 82 ℃, and the operating pressure is 2kPaA. Qualified adiponitrile products are obtained at the bottom of the tower, a mixture of byproducts and unreacted dimethyl adipate is obtained at the top of the tower, and the mixture is sent to a de-weight tower 18 for separation after being pressurized by a de-weight tower feeding pump 17. The weight-removing tower 18 adopts rectification complete condensation separation, 40 theoretical plates are arranged, the reflux ratio is 5, the tower top temperature is 116 ℃, and the operating pressure is 10kPaA. Heavy oil with indole content of 99.64 mol% is obtained at the bottom of the tower, heavy oil is obtained at the top of the heavy oil removal tower 18, and the heavy oil is sent to the light oil removal tower 20 for separation after being pressurized by the light oil removal tower feeding pump 19. The light component removal tower 20 adopts rectification complete condensation separation, 30 theoretical plates are arranged, the reflux ratio is 3, the tower top temperature is 101 ℃, and the operating pressure is 40kPaA. The light oil with 99.86 mol percent pyrrole content is obtained at the top of the light-component removing tower 20, unreacted crude dimethyl adipate is obtained at the bottom of the light-component removing tower, and the unreacted raw material is recycled by the refining tower 21. The refining column 21 adopts rectification complete condensation separation, 30 theoretical plates are arranged, the reflux ratio is 3, the temperature of the top of the column is 109 ℃, and the operating pressure is 10kPaA. The light impurity oil is obtained at the top of the tower, the recycle dimethyl adipate raw material with the purity of 99.98 percent mol is obtained at the bottom of the tower, and the recycle dimethyl adipate raw material is pressurized by a circulating pump 22 and then returned to the inlet of the 1# raw material preheater 1 for recycling.
The foregoing description is only a few examples of the present application and is not intended to limit the present application in any way, and although the present application is disclosed in the preferred examples, it is not intended to limit the present application, and any person skilled in the art may make some changes or modifications to the disclosed technology without departing from the scope of the technical solution of the present application, and the technical solution is equivalent to the equivalent embodiments.
Claims (10)
1. A method for synthesizing adiponitrile is characterized in that,
the synthesis method comprises a reaction stage, a heat recovery stage and a separation stage;
the reaction stage comprises: respectively introducing a raw material I containing dimethyl adipate a and a raw material II containing ammonia a into an ammonification reactor, and contacting with a catalyst to react to obtain an ammonification reaction product containing adiponitrile;
the heat recovery stage comprises: respectively carrying out heat exchange treatment on the raw materials I and II by utilizing the ammonification reaction product;
the separation stage: and (3) carrying out gas-liquid separation and multistage rectification treatment on the ammoniation reaction product after heat exchange to sequentially obtain methanol, ammonia b, adiponitrile, indole, pyrrole and dimethyl adipate b.
2. The synthesis method according to claim 1, wherein,
the reaction conditions are as follows: the reaction temperature is 100-500 ℃; the reaction pressure is 0-5 MPa.
3. The synthesis method according to claim 1, wherein,
in the reaction stage, the raw material I also comprises recycled dimethyl adipate b;
the raw material II also comprises circulating ammonia gas b;
preferably, the reaction stage comprises the steps of exchanging heat between a raw material I containing dimethyl adipate a and recycled dimethyl adipate b and a first strand of ammonification reaction product, then heating the raw material I to a reaction temperature, and introducing the raw material I into the ammonification reactor;
and (3) exchanging heat between the raw material II containing the ammonia gas a and the recycled ammonia gas b and a second strand of ammonification reaction product, then heating to the reaction temperature, and introducing the mixture into the ammonification reactor.
4. The synthesis method according to claim 1, wherein,
the gas-liquid separation comprises: cooling and flash evaporating the ammoniation reaction product after heat exchange to separate ammonia-containing waste gas and condensate;
preferably, the temperature of the ammoniation reaction product after heat exchange is 50-100 ℃;
the cooling temperature is-30-100 ℃;
the flash pressure is 0-10 BarG.
5. The synthesis method according to claim 4, wherein,
the multistage rectification treatment comprises:
introducing the condensate into a methanol tower for fractional condensation and rectification, obtaining ammonia gas b at the tower top, obtaining methanol at the tower side and obtaining distillate I at the tower bottom;
introducing the distillate I into a light component removal tower I for rectification complete condensation separation a, obtaining cyclopentanone water solution at the tower top and obtaining water-containing materials at the tower bottom;
introducing the water-containing material into a dehydration tower for rectification complete condensation separation b, and obtaining wastewater at the top of the tower and distillate II at the bottom of the tower;
introducing the distillate II into a product tower for rectification and complete condensation separation c, obtaining a mixture I containing dimethyl adipate at the tower top and adiponitrile at the tower bottom;
introducing the mixture I containing the dimethyl adipate into a heavy oil removal tower for rectification complete condensation separation d, obtaining heavy oil removal at the tower top and indole at the tower bottom;
introducing the heavy oil into a light oil removal tower II for rectification complete condensation separation e, obtaining pyrrole at the top of the tower, and obtaining a mixture II containing dimethyl adipate at the bottom of the tower;
introducing the mixture II of the dimethyl adipate into a refining tower for rectification complete condensation separation f, and obtaining the dimethyl adipate b at the bottom of the tower;
preferably, the ammonia gas b and the dimethyl adipate b are recycled;
preferably, the aqueous cyclopentanone solution is phase separated by a decanter to provide an oil phase and an aqueous phase.
6. The synthesis method according to claim 5, wherein,
the temperature of the top of the methanol tower is-40-60 ℃, and the pressure of the top of the methanol tower is 1-400 kPaA;
the temperature of the top of the light component removal tower I is 20-120 ℃, and the pressure of the top of the tower is 1-400 kPaA;
the temperature of the top of the dehydration tower is 10-80 ℃, and the pressure of the top of the dehydration tower is 1-400 kPaA;
the temperature of the tower top of the product tower is 30-160 ℃, and the pressure of the tower top is 0.5-200 kPaA;
the temperature of the top of the weight removing tower is 100-180 ℃, and the pressure of the top of the tower is 1-200 kPaA;
the temperature of the top of the light component removal tower II is 50-180 ℃, and the pressure of the top of the tower is 1-200 kPaA;
the temperature of the top of the refining tower is 50-180 ℃, and the pressure of the top of the refining tower is 1-200 kPaA.
7. The synthesis device of adiponitrile is characterized by comprising a reaction unit, a heat recovery unit and a separation unit, wherein the heat recovery unit is respectively communicated with the reaction unit and the separation unit through pipelines;
the reaction unit comprises a first preheater, a second preheater and an ammonification reactor, wherein the first preheater and the second preheater are respectively communicated with the ammonification reactor;
the heat recovery unit comprises a first heat exchanger and a second heat exchanger; the first heat exchanger is respectively communicated with the first preheater and the ammonification reactor, and the second heat exchanger is respectively communicated with the second preheater and the ammonification reactor;
the separation unit comprises a gas-liquid separation module, a methanol tower, a light component removal tower I, a dehydration tower, a product tower, a heavy component removal tower, a light component removal tower II and a refining tower which are sequentially communicated;
the first heat exchanger and the second heat exchanger are respectively communicated with the gas-liquid separation module;
the top of the methanol tower is provided with a gas phase outlet II which is communicated with the second heat exchanger, and the side wall of the methanol tower is also provided with a methanol outlet;
the bottom of the refining tower is provided with a dimethyl adipate outlet which is communicated with the first heat exchanger;
wherein the alcohol tower, the light component removing tower I, the dehydrating tower, the product tower, the heavy component removing tower, the light component removing tower II and the refining tower are all rectifying towers.
8. The synthesizing apparatus according to claim 7, wherein,
the reflux ratio of the methanol tower is 0.1-50, and the theoretical plate number is 5-40;
the reflux ratio of the light component removal tower I is 1-150, and the theoretical plate number is 5-80;
the reflux ratio of the dehydration tower is 0.1-40, and the theoretical plate number is 5-80;
the reflux ratio of the product tower is 0.1-40, and the theoretical plate number is 5-80;
the reflux ratio of the weight removing tower is 0.1-40, and the theoretical plate number is 5-80;
the reflux ratio of the light component removal tower II is 0.1-40, and the theoretical plate number is 5-80;
the reflux ratio of the refining tower is 0.1-40, and the theoretical plate number is 5-80.
9. The synthesizing apparatus according to claim 7, wherein,
the gas-liquid separation module is provided with an ammonification reaction product inlet, a gas phase outlet I and a liquid phase outlet I;
the first heat exchanger and the second heat exchanger are respectively communicated with the ammonification reaction product inlet;
the liquid phase outlet I is communicated with the tower side wall of the methanol tower;
the bottom of the methanol tower is communicated with the tower side wall of the light component removal tower I;
the bottom of the light component removal tower I is communicated with the side wall of the dehydration tower;
the bottom of the dehydration tower is communicated with the tower side wall of the product tower;
the top of the product tower is communicated with the tower side wall of the heavy-removal tower;
the top of the heavy-removal tower is communicated with the tower side wall of the light-removal tower II;
the bottom of the light component removal tower II is communicated with the tower side wall of the refining tower;
preferably, the top of the light component removal tower I is provided with a cyclopentanone water solution outlet;
an adiponitrile outlet is arranged at the bottom of the product tower;
an indole outlet is arranged at the bottom of the heavy-duty removal tower;
and an pyrrole outlet is arranged at the top of the light component removing tower II.
10. The synthesizing apparatus according to claim 9, wherein,
the gas-liquid separation module comprises a condenser and a flash tank which are connected in sequence; wherein the flash tank is provided with a gas phase outlet I and a liquid phase outlet I, and the condenser is provided with an ammonification reaction product inlet;
preferably, the synthesis apparatus further comprises an ammonia recycle compressor;
the ammonia circulating compressor is respectively communicated with the gas phase outlet II and the second heat exchanger;
preferably, the synthesis device further comprises a decanter;
the decanter is in communication with the cyclopentanone aqueous solution outlet.
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