CN116947693A - Synthesis method of 6-aminocapronitrile - Google Patents
Synthesis method of 6-aminocapronitrile Download PDFInfo
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- CN116947693A CN116947693A CN202210385783.4A CN202210385783A CN116947693A CN 116947693 A CN116947693 A CN 116947693A CN 202210385783 A CN202210385783 A CN 202210385783A CN 116947693 A CN116947693 A CN 116947693A
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- catalyst
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- caprolactam
- aminocapronitrile
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- KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000001308 synthesis method Methods 0.000 title claims description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 84
- 239000003054 catalyst Substances 0.000 claims abstract description 65
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 29
- 229910004298 SiO 2 Inorganic materials 0.000 claims abstract description 23
- 238000004176 ammonification Methods 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 16
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 238000011068 loading method Methods 0.000 claims description 8
- 238000005470 impregnation Methods 0.000 claims description 7
- 238000010335 hydrothermal treatment Methods 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 101710134784 Agnoprotein Proteins 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 238000013022 venting Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract description 18
- 208000012839 conversion disease Diseases 0.000 abstract description 10
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- -1 alkali metal modified nickel Chemical class 0.000 description 3
- 239000000498 cooling water Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- URRHWTYOQNLUKY-UHFFFAOYSA-N [AlH3].[P] Chemical compound [AlH3].[P] URRHWTYOQNLUKY-UHFFFAOYSA-N 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention provides a method for efficiently synthesizing hexamethylenediamine key intermediate 6-aminocapronitrile, which comprises the steps of reacting caprolactam melt feed with ammonia gas, and using Ag/SiO 2 The catalyst is an ammoniation catalyst. The process is simple and easy to operate, the reaction temperature is low, and the reaction conversion rate and the selectivity are high.
Description
Technical Field
The invention relates to a method for preparing 6-aminocapronitrile, belonging to the field of fine chemical industry.
Background
6-aminocapronitrile is an important chemical intermediate that can be used to produce 1, 6-hexamethylenediamine by hydrogenation. Hexamethylenediamine is an important raw material for producing polyamide 66 (PA 66), PA610, HDI (1, 6-hexamethylene diisocyanate) and other products. Internationally, the production of hexamethylenediamine is mainly monopolized by large-scale nationwide companies, and the production is very concentrated. The sum of the three families of inflight, basf and oldham accounts for 74% of the global capacity and is in the highly oligopolistic industry. The current preparation of 6-aminocapronitrile is mainly obtained by partial hydrogenation of 1, 6-adiponitrile, for example, CN105921164B provides a preparation method and application of a nitrogen-doped activated carbon supported alkali metal modified nickel-based catalyst, which can have higher activity and higher total selectivity of 6-aminocapronitrile and hexamethylenediamine under relatively mild reaction conditions when applied to adiponitrile hydrogenation process.
The industrialization of preparing hexamethylenediamine from caprolactam is realized in 1965 in Japanese Dongli, and the method is mainly used for recycling recovered waste materials such as caprolactam inferior products or waste nylon. The key point of the process is that caprolactam and ammonia react with the catalyst to generate aminocapronitrile.
。
The technology is also researched at home, and patent CN107602416A provides a method for preparing 6-aminocapronitrile by a gas phase method, caprolactam steam and hot ammonia gas are mixed according to a certain mass ratio and subjected to ammonification dehydration reaction in the presence of a catalyst, and a product is separated and purified to obtain pure 6-aminocapronitrile. The catalyst is one or more than two of alkaline earth metal oxide, transition metal oxide, silicon dioxide and active aluminum oxide.
CN107739318A provides a method and apparatus for preparing 6-aminocapronitrile by using caprolactam liquid phase method, mixing caprolactam, organic solvent and catalyst according to a certain mass ratio to obtain a mixed solution, adding the mixed solution into a reaction kettle, stirring and heating to a certain temperature, introducing ammonia gas into the mixed solution to react, rectifying and purifying the reaction product after the reaction is finished to obtain pure 6-aminocapronitrile.
CN110404582a discloses a preparation method of a catalyst for ammonifying caprolactam, which uses a phosphorus-aluminum molecular sieve as a carrier, carries a certain amount of active components of magnesium nitrate, aluminum nitrate and nickel nitrate by an impregnation method at a certain temperature, and obtains an ammonifying dehydration catalyst after drying, forming and roasting, wherein the catalyst is filled in a fixed bed, and caprolactam and ammonia react under the conditions of 420-500 ℃ and 0-1 mpa; the catalyst obtained by the method has simple preparation method, the conversion rate of caprolactam is more than 80 percent, and the selectivity of 6-aminocapronitrile is more than 99 percent.
CN111004148A is prepared by respectively preheating caprolactam and ammonia gas according to a molar ratio of 1:3-1:20, mixing, further heating to obtain a mixture, feeding the mixture into a reactor, carrying out ammonification and dehydration reaction in the presence of a catalyst to obtain an ammonification reactant, wherein the catalyst is composed of alkaline earth metal salt or transition metal salt as an active component and titanium dioxide or ZSM-5 molecular sieve as a carrier, and finally separating and purifying to obtain the target product 6-aminocapronitrile.
The related technology has no industrialized case in China. Because of the relatively high price of caprolactam, the current process for preparing hexamethylenediamine from lactam has no advantages. Along with the interior of the medium petrochemical industry and the subsequent upward of caprolactam devices in the industry, the price of the caprolactam in the future tends to be downward, and the sufficient caprolactam raw materials of the medium petrochemical industry are utilized for producing hexamethylenediamine, so that the large-scale industrialization of synthesizing hexamethylenediamine by the ammonification of the caprolactam is possible. .
Disclosure of Invention
The invention aims to provide a synthesis method of 6-aminocapronitrile.
A synthesis process of 6-aminocapronitrile mainly comprises the following steps: the caprolactam and ammonia gas enter a fixed bed reactor in a certain proportion, and under the action of a certain reaction condition and a catalyst, the 6-aminocapronitrile is synthesized by continuous ammonification and dehydration reaction.
。
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
1. the ammoniation catalyst is Ag/SiO as the catalyst prepared by the impregnation method 2 Catalyst, ag weight is the carrier SiO 2 The weight ratio of the catalyst is 1% -6%, and the carrier is SiO 2 Is a small ball with the particle diameter of 0.5mm-2 mm. The preparation method of the catalyst comprises the following steps: carrier SiO 2 Through hydrothermal treatment at 160-200 deg.cAfter drying, agNO is loaded in proportion by an impregnation method 3 Drying and roasting to obtain Ag 2 O/SiO 2 Catalyst having a specific surface area of 40m 2 /g-60 m 2 And/g. The catalyst is filled into a fixed bed, and hydrogen or ammonia is used for reducing Ag before ammonification reaction 2 O/SiO 2 Catalyst for converting it into Ag/SiO 2 A catalyst.
2. Caprolactam enters a preheater in a molten state and is gasified, and ammonia and caprolactam enter a catalyst bed after being preheated and mixed in the preheater. The molar ratio of ammonia to caprolactam is 5-25, and the reaction liquid hourly space velocity (molten caprolactam feed rate/catalyst loading volume) is 0.1h -1 -0.5h -1 The reaction temperature is controlled to 280-320 ℃, the outlet of the reactor is in a venting state, and the reaction pressure is normal pressure or micro-positive pressure.
3. The receiving tank of the reaction product is fully cooled by circulating water at the temperature of 10-30 ℃ to fully liquefy organic materials in the product, and unreacted ammonia gas is discharged for treatment.
The invention has the beneficial effects that:
a6-aminocapronitrile process is provided, in which caprolactam melt feed is reacted with ammonia gas using Ag/SiO 2 The catalyst is an ammoniation catalyst. The process is simple and easy to operate, the reaction temperature is low, and the reaction conversion rate and the selectivity are high.
Detailed Description
The invention will be further illustrated with reference to specific examples.
Example 1
Preparation of the catalyst: 0.5mm silicon pellet, 160 ℃ hydrothermal treatment and impregnation method for preparing Ag 2 O/SiO 2 Catalyst, ag weight is the carrier SiO 2 The weight proportion of (2) is 1%. Specific surface area of catalyst 60 m 2 And/g. After loading into a fixed bed reactor, ag is reduced by ammonia gas 2 O/SiO 2 Catalyst for conversion of Ag/SiO suitable for ammonification 2 A catalyst.
Ammonification reaction: the molar ratio of ammonia to caprolactam is 5, the reaction temperature is controlled to be 280 ℃, and the hourly space velocity of caprolactam feed liquid is 0.1h -1 The receiving tank cooling water was 10 ℃. After 4 hours of reaction, the organic phase in the receiving tank was dissolved with acetonitrile and the composition was analyzed by gas chromatography. The results showed that the reaction product had a composition of: 17.27% of caprolactam, 76.89% of 6-aminocapronitrile, 82.73% of ammoniation reaction conversion and 92.94% of 6-aminocapronitrile reaction selectivity.
Example 2
Preparation of the catalyst: 1mm silicon pellet, hydrothermal treatment at 180 ℃ and preparation of Ag by impregnation method 2 O/SiO 2 Catalyst, ag weight is the carrier SiO 2 The weight proportion of (2) is 3%. Specific surface area of catalyst 54 m 2 And/g. After loading into a fixed bed reactor, ag is reduced by ammonia gas 2 O/SiO 2 Catalyst for conversion of Ag/SiO suitable for ammonification 2 A catalyst.
Ammonification reaction: the molar ratio of ammonia to caprolactam is 10, the reaction temperature is controlled to 300 ℃, and the hourly space velocity of caprolactam feed liquid is 0.2h -1 The receiving tank cooling water was 20 ℃. After 4 hours of reaction, the organic phase in the receiving tank was dissolved with acetonitrile and the composition was analyzed by gas chromatography. The results showed that the reaction product had a composition of: caprolactam 11.04%, 6-aminocapronitrile 87.50%, ammonification reaction conversion 88.96% and 6-aminocapronitrile selectivity 98.36%.
Example 3
Preparation of the catalyst: 2mm silicon pellets, hydrothermal treatment at 180 ℃ and preparation of Ag by impregnation method 2 O/SiO 2 Catalyst, ag weight is the carrier SiO 2 The weight proportion of (2) is 6%. The specific surface area of the catalyst is 57 m 2 And/g. After loading into a fixed bed reactor, ag is reduced by ammonia gas 2 O/SiO 2 Catalyst for conversion of Ag/SiO suitable for ammonification 2 A catalyst.
Ammonification reaction: the molar ratio of ammonia to caprolactam is 15, the reaction temperature is controlled to 320 ℃, and the hourly space velocity of caprolactam feed liquid is 0.2h -1 The receiving tank cooling water was 20 ℃. After 4 hours of reaction, the organic phase in the receiving tank was dissolved with acetonitrile and the composition was analyzed by gas chromatography. The results showed that the reaction product had a composition of: caprolactam 0.81%, 6-aminocapronitrile 98.47%, ammoniation reaction conversion rate99.19% and a reaction selectivity of 99.27% for 6-aminocapronitrile.
Example 4
Preparation of the catalyst: the difference from example 3 is that the hydrothermal treatment temperature was changed to 200℃and the specific surface area of the catalyst was 42 m 2 /g。
Ammonification reaction: the reaction and analysis method were the same as in example 3. The results showed that the reaction product had a composition of: caprolactam 0.93%, 6-aminocapronitrile 96.48%, ammonification reaction conversion 99.07% and 6-aminocapronitrile selectivity 97.39%.
Example 4
Preparation of the catalyst: the difference from example 3 is that the Ag loading was adjusted to 1% and the specific surface area of the catalyst was 55 m 2 /g。
Ammonification reaction: the reaction and analysis method were the same as in example 3. The results showed that the reaction product had a composition of: caprolactam 7.18%, 6-aminocapronitrile 92.02%, ammonification reaction conversion 92.82% and 6-aminocapronitrile reaction selectivity 99.14%.
Example 5
Preparation of the catalyst: the same as in example 3.
Ammonification reaction: the reaction conditions differ from those of example 3 in that: caprolactam feed liquid hourly space velocity of 0.5h -1 The remaining reactions were identical to the sample analysis conditions. The results showed that the reaction product had a composition of: 13.79% of caprolactam, 86.15% of 6-aminocapronitrile, 86.21% of ammoniation reaction conversion rate and 99.93% of 6-aminocapronitrile reaction selectivity.
Example 6
Preparation of the catalyst: the same as in example 3.
Ammonification reaction: the reaction conditions differ from those of example 3 in that: the ammonification reaction temperature was adjusted to 300 ℃, and the other reactions and sampling analysis conditions were the same. The results showed that the reaction product had a composition of: caprolactam 2.35%, 6-aminocapronitrile 97.15%, ammonification reaction conversion 97.65% and 6-aminocapronitrile reaction selectivity 99.49%.
Example 7
Preparation of the catalyst: the difference from example 2 is that the Ag loading was adjusted6% of the catalyst, the specific surface area of the catalyst is 51 m 2 /g。
Ammonification reaction: the reaction and analysis method were the same as in example 3. The results showed that the reaction product had a composition of: caprolactam 5.33%, 6-aminocapronitrile 92.97%, ammonification reaction conversion 94.67% and 6-aminocapronitrile reaction selectivity 98.20%.
Claims (10)
1. A synthesis method of 6-aminocapronitrile is characterized in that: caprolactam and ammonia gas are fed into a reactor in proportion, and under the action of a catalyst, ammonification dehydration reaction is continuously carried out to synthesize 6-aminocapronitrile.
2. The method of claim 1, wherein the reactor is a fixed bed reactor.
3. The process according to claim 1, wherein the catalyst is Ag/SiO 2 A catalyst.
4. A process according to claim 3, wherein in the catalyst, ag is based on SiO as a carrier 2 The weight ratio of the (C) is 1% -6%.
5. A process according to claim 3, wherein in the catalyst, the carrier SiO 2 Is a small ball with the particle diameter of 0.5mm-2 mm.
6. A process according to claim 3, characterized in that the catalyst has a specific surface area of 40m 2 /g-60 m 2 /g。
7. A process according to claim 3, characterized in that the catalyst preparation process: carrier SiO 2 Carrying out hydro-thermal treatment at 160-200 ℃, drying, and loading AgNO in proportion by an impregnation method 3 Drying and roasting to obtain Ag 2 O/SiO 2 A catalyst.
8. A process according to claim 1 or 3, characterized in that caprolactam enters the preheater in the molten state and is gasified, ammonia and caprolactam are preheated and mixed in the preheater before entering the catalyst bed; the catalyst is filled into a fixed bed, and hydrogen or ammonia is used for reducing Ag before ammonification reaction 2 O/SiO 2 Catalyst for converting it into Ag/SiO 2 A catalyst.
9. The process according to claim 1 or 8, wherein the molar ratio of the catalyst ammonia to caprolactam is from 5 to 25 and the reaction liquid hourly space velocity (molten caprolactam feed rate/catalyst loading volume) is from 0.1 to 0.1h -1 -0.5h -1 The reaction temperature is controlled to 280-320 ℃, the outlet of the reactor is in a venting state, and the reaction pressure is normal pressure or micro-positive pressure.
10. The method according to claim 1 or 9, wherein the receiving tank of the reaction product is sufficiently cooled with circulating water at 10 ℃ to 30 ℃ to sufficiently liquefy the organic material in the product, and unreacted ammonia gas is discharged for disposal.
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