CN113504262A - O-methoxyacetanilide nitration thermal safety risk assessment method - Google Patents
O-methoxyacetanilide nitration thermal safety risk assessment method Download PDFInfo
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- CN113504262A CN113504262A CN202110410646.7A CN202110410646A CN113504262A CN 113504262 A CN113504262 A CN 113504262A CN 202110410646 A CN202110410646 A CN 202110410646A CN 113504262 A CN113504262 A CN 113504262A
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- 238000006396 nitration reaction Methods 0.000 title claims abstract description 74
- 238000000034 method Methods 0.000 title claims abstract description 45
- FGOFNVXHDGQVBG-UHFFFAOYSA-N N-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(C)=O FGOFNVXHDGQVBG-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000012502 risk assessment Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 52
- 238000012360 testing method Methods 0.000 claims abstract description 38
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 238000011156 evaluation Methods 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 20
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 6
- 229910017604 nitric acid Inorganic materials 0.000 claims description 6
- 238000009825 accumulation Methods 0.000 claims description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 5
- 230000001133 acceleration Effects 0.000 claims description 3
- 238000002474 experimental method Methods 0.000 claims description 3
- 238000013112 stability test Methods 0.000 claims description 3
- 238000012854 evaluation process Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 6
- 230000002265 prevention Effects 0.000 abstract description 5
- 238000013210 evaluation model Methods 0.000 abstract description 2
- 238000007599 discharging Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 238000007707 calorimetry Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000012824 chemical production Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N25/00—Investigating or analyzing materials by the use of thermal means
- G01N25/20—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity
- G01N25/48—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity on solution, sorption, or a chemical reaction not involving combustion or catalytic oxidation
- G01N25/4806—Details not adapted to a particular type of sample
- G01N25/484—Heat insulation
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Abstract
The invention provides a method for evaluating the thermal safety risk of o-methoxyacetanilide nitration reaction, and relates to the technical field of nitration processes. The o-methoxyacetanilide nitration thermal safety risk assessment method comprises the following steps: step one, testing the thermal stability of a material; secondly, carrying out a reaction calorimetric test on the nitration reaction; step three, carrying out secondary decomposition test on the nitration reaction finished liquid; and step four, evaluating the safety risk of the nitration reaction. A safety risk evaluation model of the nitration reaction heat of the o-methoxyacetanilide is established through the technical content, effective technical support and guarantee can be provided for the thermal safety of the nitration process and the production safety accident prevention and treatment according to the evaluation result, and the method has very important significance for the safety production and the major accident prevention and treatment of the chemical industry.
Description
Technical Field
The invention relates to the technical field of nitration processes, in particular to a thermal safety risk assessment method for a nitration reaction of o-methoxyacetanilide.
Background
The chemical industry of China has long become the mainstay of national economy. The production method has the advantages that the number of chemical enterprises is large, the reaction type related range is wide, the production device and the process are complex and changeable, and meanwhile, most of raw materials, intermediate products, products and wastes related in the production process have the characteristics of flammability, explosiveness, toxicity, harmfulness and easy corrosion. The characteristics of chemical production determine that the production safety accident has high possibility and serious accident consequences, and besides direct losses such as casualties, property loss and the like are easily caused in a large quantity, the chemical production can also cause profound negative effects on the environment. At present, the domestic nitration process reaction heat safety risk assessment method is vacant, so that the establishment of the nitration process reaction heat safety risk assessment method has important significance for chemical industry accident prevention.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a method for evaluating the thermal safety risk of the nitration reaction of o-methoxyacetanilide, which solves the problem that the existing domestic nitration process thermal safety risk evaluation method is vacant.
(II) technical scheme
In order to achieve the purpose, the invention is realized by the following technical scheme: a method for evaluating the thermal safety risk of o-methoxyacetanilide nitration reaction comprises the following steps:
the method comprises the following steps: test of thermal stability of Material
Carrying out thermal stability test on the o-methoxyacetanilide and the nitration reaction liquid by a differential scanning calorimeter;
step two: calorimetric reaction test for nitration reactions
The test was carried out using a fully automatic reaction calorimeter RC1e according to the following protocol:
then obtaining the heat quantity, the heat conversion rate, the heat accumulation rate and the Tcf curve which are fed and discharged in the nitration reaction process;
step three: secondary decomposition test of nitration reaction completion liquid
And (3) carrying out secondary decomposition test on the nitration reaction finished liquid by using a TAC-500A adiabatic acceleration calorimeter to obtain: time-temperature-pressure curve of nitration reaction finished material ARC scanning mode test, time-temperature-pressure curve of nitration reaction finished material ARC HWS mode test, nitration reaction finished liquid adiabatic heat test curve, and then nitration reaction finished liquid is subjected to thermodynamic parameter calculation and adiabatic experiment TMR calculation;
step four: nitration reaction safety risk assessment
The evaluation content comprises the following steps:
thermal evaluation of material decomposition, severity evaluation, possibility evaluation, risk matrix evaluation and reaction process risk evaluation.
Preferably, the nitration reaction liquid is 65% nitric acid and dichloromethane.
Preferably, the technique of the o-methoxyacetanilide nitration reaction is as follows:
adding dichloromethane and o-methoxyacetanilide into a reaction kettle, stirring for dissolving, then dropwise adding concentrated nitric acid, controlling the speed of dropwise adding, wherein the whole dropwise adding process is about 2 hours, and after dropwise adding, keeping the temperature and reacting for 1 hour;
the reaction equation is as follows:
(III) advantageous effects
The invention provides a thermal safety risk assessment method for o-methoxyacetanilide nitration reaction. The method has the following beneficial effects:
according to the invention, a safety risk evaluation model for the nitration reaction heat of the o-methoxyacetanilide is established through technical contents, effective technical support and guarantee can be provided for the thermal safety of the nitration process and the prevention and treatment of production safety accidents according to evaluation results, and the method has very important significance for the safety production and the prevention and treatment of major accidents in the chemical industry.
Drawings
FIG. 1 is a DSC test chart of o-methoxyacetanilide;
FIG. 2 is a DSC test chart of the nitration liquid;
FIG. 3 is a graph showing the charging, discharging heat, thermal conversion rate, thermal accumulation rate and Tcf of the nitration reaction process;
FIG. 4 is a time-temperature-pressure graph of a nitration reaction completion ARC scan mode test;
FIG. 5 is a time-temperature-pressure graph of a nitration reaction completion ARC HWS mode test;
FIG. 6 is a graph of a liquid adiabatic calorimetry test performed on a nitration reaction completion;
FIG. 7 is a graph showing calculation of thermodynamic parameters of a liquid after nitration reaction;
FIG. 8 is a TMR calculation chart of the nitrification reaction completion liquid adiabatic test.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example (b):
the embodiment of the invention provides a method for evaluating the thermal safety risk of o-methoxyacetanilide nitration reaction, which comprises the following steps:
the method comprises the following steps: test of thermal stability of Material
Carrying out thermal stability test on o-methoxyacetanilide and the nitration reaction solution by a differential scanning calorimeter, wherein the obtained test results are respectively shown in a figure 1 and a figure 2;
as can be seen from FIG. 1, 2 endothermic peaks are detected at (0-480) deg.C, the 1 st endotherm begins at 86.21 deg.C and ends at 87.32 deg.C, the absorbed heat is 115.73J/g, which is the heat that needs to be absorbed by the melting of o-methoxyacetanilide; the second heat absorption starts from 157.23 ℃ and ends at 189.31 ℃, the heat absorption capacity is 402.91J/g, and the heat absorption capacity is the heat absorbed by vaporization when the temperature reaches the boiling point of the o-methoxyacetanilide;
as shown in figure 2, 1 endothermic peak and 1 exothermic peak exist between (0-480) DEG C, the endothermic peak starts from 11.83 ℃ and ends at 75.75 ℃, the absorbed heat is 543.58J/g, which is the heat to be absorbed by vaporization when the temperature reaches the boiling point of the solvent dichloromethane and nitric acid in the reaction solution; the exothermic peak starts from 108.41 ℃ and ends at 111.71 ℃, and the exothermic quantity is 273.54J/g;
step two: calorimetric reaction test for nitration reactions
The reaction ratio of 192g of o-methoxyacetanilide, 202.4g of 65% nitric acid and 800ml of dichloromethane is measured by using a full-automatic reaction calorimeter RC1e according to the following procedures:
then obtaining the heat quantity of feeding and discharging, the heat conversion rate, the heat accumulation rate and a Tcf curve in the nitration reaction process, as shown in figure 3, the hatched boundary line in the graph is a heat effect curve of the heat discharging process, the total heat quantity of the reaction obtained after the time integration is calculated, the feeding is started in the reaction process, the heat preservation reaction is ended, the temperature in the kettle is stable, the total heat quantity of discharging is 158.33KJ, the total mass of materials participating in the reaction is 1454.4g, and therefore the specific heat quantity of discharging of the reaction is 108.86J/g;
the delta Tad is adiabatic temperature rise and is the temperature which can raise the system under the adiabatic condition for all heat released by synthesis reaction or material decomposition, and the delta Tad of the reaction is 79.1K;
the MTSR is the highest temperature which can be reached by a system under the adiabatic condition when the material accumulation is maximum, and the MTSR is 104 ℃ which corresponds to the reaction runaway in the nitration reaction process;
because the reaction is carried out under normal pressure, the technical maximum temperature MTT is the boiling point of the maximum material in the reaction system under normal pressure, namely the boiling point of dichloromethane: 39.75 ℃;
step three: secondary decomposition test of nitration reaction completion liquid
And (3) carrying out secondary decomposition test on the nitration reaction finished liquid by using a TAC-500A adiabatic acceleration calorimeter to obtain: a time-temperature-pressure curve of a nitration completion material ARC scan mode test (as shown in FIG. 4 and under a scan mode), a time-temperature-pressure curve of a nitration completion material ARC HWS mode test (as shown in FIG. 5 and under an HWS mode, the sample temperature is at the initial point and the pressure is at the bottom), a nitration completion liquid adiabatic calorimetry test curve (as shown in FIG. 6, the curves from top to bottom are the upper cover temperature, the instrument environment temperature, the sample temperature and the sample pressure respectively between 1600 min and 1700 min), and then a nitration completion liquid is subjected to thermodynamic parameter calculation and adiabatic experiment TMR calculation, which respectively correspond to FIG. 7 and FIG. 8;
as can be seen from FIGS. 5 to 7, the initial decomposition temperature of the nitration reaction-completed liquid is 115.96 ℃, the decomposition reaction-completed temperature is 131.72 ℃, the heat release is 278.84J/g, the adiabatic temperature rise delta Tad of the secondary reaction process of the nitration reaction-completed liquid is 68.53 ℃, and the T is calculated from FIG. 8D24111.8 ℃ and a runaway reaction maximum reaction rate arrival time TMR when the process temperature is 25 DEG Cad>24h, when the temperature reaches the Maximum Temperature (MTSR) of the system, the runaway reaction reaches the maximum reaction rate reaching time TMRad>24h；
Step four: nitration reaction safety risk assessment
The evaluation content comprises the following steps:
evaluating material decomposition heat, evaluating severity, evaluating possibility, evaluating a risk matrix and evaluating the risk degree of a reaction process;
evaluation of heat of decomposition of substance: according to the adiabatic calorimetry test result of the nitration reaction finished liquid, the decomposition heat release of the nitration reaction finished liquid is 278.84J/g, the decomposition heat of the oxidation reaction finished material is 278.84J/g <400J/g, the evaluation is 1 grade, and the material has potential explosion danger;
and (3) evaluating the severity: according to the reaction calorimetric test result of the nitration reaction, the adiabatic temperature rise delta Tad =79.1K is more than 50K, the severity of the runaway reaction of the nitration reaction is evaluated to be 2 grade, and the short-term damage of a factory can be caused by the runaway reaction;
possibility evaluation: according to the adiabatic calorimetry test result of the nitration reaction completion liquid, the reaction liquid TD is completed24Is 111.8 ℃, and the process temperature T of the systemPAt 25 ℃ and the maximum reaction rate arrival time TMR of the runaway reactionad>24h, when the temperature reaches the highest temperature of the system(MTSR), its runaway reaction maximum reaction rate arrival time TMRad>24h, evaluating the possibility of the runaway reaction to be level 1, and rarely generating the runaway reaction;
and (3) risk matrix evaluation: and obtaining a risk matrix according to the results of the severity evaluation and the performance evaluation, wherein the risk matrix is evaluated to be I grade, and the I grade risk is acceptable risk: conventional control measures can be taken, and safety management and equipment level are properly improved;
and (3) assessing the risk degree of the reaction process: according to the reaction calorimetric test result of the nitration reaction, the process temperature Tp =25 ℃, the highest temperature MTSR =104 ℃ which can be reached by the synthesis reaction under the actual feeding speed under the adiabatic condition, the technical highest temperature MTT =39.75 ℃, and the test T of the secondary decomposition of the nitration reaction finished liquidD24=111.8 ℃ to obtain Tp<MTT<MTSR<TD24（25℃<39.75℃<104℃<111.8 ℃), i.e. the reaction process risk at the actual feed rate was rated 3.
The process has the risks of material flushing and decomposition, after the target reaction is out of control, the temperature quickly reaches the technical limit (MTSR > MTT) but does not trigger the secondary decomposition reaction (MTSR < TD 24), at the moment, the process safety depends on the heat release rate of the target reaction in MTT, and at the moment, the heat can be removed through condensation; spare cooling systems, emergency discharge, quench devices and pressure relief devices may also be employed; therefore, on the basis of being equipped with a conventional automatic control system, carrying out centralized monitoring and automatic adjustment (DCS or PLC) on main reaction parameters, setting alarm and interlocking control deviating from normal values, and setting relief facilities such as rupture discs, safety valves and the like, emergency cut-off, emergency termination reaction and emergency cooling are also required to be set.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (3)
1. A method for evaluating the thermal safety risk of o-methoxyacetanilide nitration reaction is characterized by comprising the following steps:
the method comprises the following steps: test of thermal stability of Material
Carrying out thermal stability test on the o-methoxyacetanilide and the nitration reaction liquid by a differential scanning calorimeter;
step two: calorimetric reaction test for nitration reactions
The test was carried out using a fully automatic reaction calorimeter RC1e according to the following protocol:
then obtaining the heat quantity, the heat conversion rate, the heat accumulation rate and the Tcf curve which are fed and discharged in the nitration reaction process;
step three: secondary decomposition test of nitration reaction completion liquid
And (3) carrying out secondary decomposition test on the nitration reaction finished liquid by using a TAC-500A adiabatic acceleration calorimeter to obtain: time-temperature-pressure curve of nitration reaction finished material ARC scanning mode test, time-temperature-pressure curve of nitration reaction finished material ARC HWS mode test, nitration reaction finished liquid adiabatic heat test curve, and then nitration reaction finished liquid is subjected to thermodynamic parameter calculation and adiabatic experiment TMR calculation;
step four: nitration reaction safety risk assessment
The evaluation content comprises the following steps:
thermal evaluation of material decomposition, severity evaluation, possibility evaluation, risk matrix evaluation and reaction process risk evaluation.
2. The method for evaluating the thermal safety risk of the nitration reaction of o-methoxyacetanilide according to claim 1, wherein: the nitration reaction liquid is 65% nitric acid and dichloromethane.
3. The method for evaluating the thermal safety risk of the nitration reaction of o-methoxyacetanilide according to claim 1, wherein: the process of the o-methoxyacetanilide nitration reaction comprises the following steps:
adding dichloromethane and o-methoxyacetanilide into a reaction kettle, stirring for dissolving, then dropwise adding concentrated nitric acid, controlling the speed of dropwise adding, wherein the whole dropwise adding process is about 2 hours, and after dropwise adding, keeping the temperature and reacting for 1 hour;
the reaction equation is as follows:
。
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101165043A (en) * | 2006-10-19 | 2008-04-23 | 北京化工大学 | Solid acid green nitration method for diphenyl ether derivative |
| CN104910038A (en) * | 2015-04-27 | 2015-09-16 | 杭州宇田科技有限公司 | 3-Amino-4-methoxy acetanilide (II) preparation method |
| CN109949874A (en) * | 2019-04-16 | 2019-06-28 | 南京工业大学 | A kind of risk stratification method of fine chemistry industry production process security evaluation |
| CN111766265A (en) * | 2020-06-30 | 2020-10-13 | 昆山德源环保发展有限公司 | Method for testing thermal stability of waste organic solvent by using DSC (differential scanning calorimetry) |
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- 2021-04-16 CN CN202110410646.7A patent/CN113504262A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101165043A (en) * | 2006-10-19 | 2008-04-23 | 北京化工大学 | Solid acid green nitration method for diphenyl ether derivative |
| CN104910038A (en) * | 2015-04-27 | 2015-09-16 | 杭州宇田科技有限公司 | 3-Amino-4-methoxy acetanilide (II) preparation method |
| CN109949874A (en) * | 2019-04-16 | 2019-06-28 | 南京工业大学 | A kind of risk stratification method of fine chemistry industry production process security evaluation |
| CN111766265A (en) * | 2020-06-30 | 2020-10-13 | 昆山德源环保发展有限公司 | Method for testing thermal stability of waste organic solvent by using DSC (differential scanning calorimetry) |
Non-Patent Citations (2)
| Title |
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| 朱洪法: "《精细化工——产品、技术与配方》", 31 August 1998, 中国石化出版社 * |
| 邹勇: "《管式和釜式反应器中硝化反应SIL评估和比较研究》", 《中国学位论文全文数据库》 * |
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