CN104730163B - Based on 3, the detection of 3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone controls the method that 3,5,6-trichloropyridine-2-sodium alkoxide produce - Google Patents
Based on 3, the detection of 3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone controls the method that 3,5,6-trichloropyridine-2-sodium alkoxide produce Download PDFInfo
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- trichloropyridine
- sodium alkoxide
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- ketone
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- 229910052708 sodium Inorganic materials 0.000 title claims abstract description 40
- 239000011734 sodium Substances 0.000 title claims abstract description 40
- 238000001514 detection method Methods 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000000523 sample Substances 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 10
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 9
- 239000012488 sample solution Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 239000012086 standard solution Substances 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 9
- 229960000583 acetic acid Drugs 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 claims description 6
- 238000005070 sampling Methods 0.000 claims 1
- -1 sodium alkoxide Chemical class 0.000 abstract description 12
- MFTSCJIEOYYRPN-UHFFFAOYSA-N ClC=1C(=C(C(=NC1)[Na])Cl)Cl Chemical compound ClC=1C(=C(C(=NC1)[Na])Cl)Cl MFTSCJIEOYYRPN-UHFFFAOYSA-N 0.000 abstract description 6
- 238000003908 quality control method Methods 0.000 abstract description 2
- HETBVMSHRPRFQU-UHFFFAOYSA-N (3,5,6-trichloropyridin-2-yl)sulfanylphosphonic acid Chemical compound OP(O)(=O)SC1=NC(Cl)=C(Cl)C=C1Cl HETBVMSHRPRFQU-UHFFFAOYSA-N 0.000 abstract 3
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 230000010355 oscillation Effects 0.000 description 8
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000013068 control sample Substances 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- VMHZXXPDUOVTHD-UHFFFAOYSA-N 2,3,4-trichloropyridine Chemical compound ClC1=CC=NC(Cl)=C1Cl VMHZXXPDUOVTHD-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
The present invention proposes a kind of based on 3,3,5,6 tetrachloros 4, the detection of 4 dihydropyridine 2 ketone controls the method that 3,5,6 trichloropyridine 2 sodium alkoxide produce, comprise the steps: that (1) is 3,5,6 trichloropyridine 2 sodium alkoxide production processes take sodium alkoxide and produces intermediate sample, according to mass volume ratio 40 70mg/50mL, it is dissolved in methanol, makes sample solution；Accurately weigh 3,3,5,6 tetrachloro 4,4 dihydropyridine 2 ketone standard substance 40 60mg, make standard solution according to mass volume ratio 40 70mg/50mL；(2) sample solution carries out high performance liquid chromatography detection after filtering, and the production process detecting qualified rear 3,5,6 trichloropyridine 2 sodium alkoxide adds alkali liquor, carries out next step reaction.The method that the present invention proposes, controls low cost, accurately and reliably.Quickly, accurately, the quality control in producing for trichloro pyridyl sodium alcoholate provides guarantee to detection method, has preferable Industry Control Application prospect.
Description
Technical field
The invention belongs to organic chemistry filed, be specifically related to a kind of production process monitoring method of heterocyclic organic compounds.
Background technology
Along with country's attention to environmental protection in recent years, in pesticide producing, benzene class and alcohols solvent progressively disable, and develop ring
Guarantor's type pesticide is imperative.
Chlopyrifos product is wide because of insecticidal range, effective, remains low, as a kind of higher effective and lower toxic pesticide, applies in a large number
On crops, and its raw material 3,5,6-trichloropyridine-2-sodium alkoxide are also with a large amount of utilizations of chlopyrifos, its quality produced
Quality, also the remote-effects quality of chlopyrifos finished product.And this method is 3,5,6-trichloropyridine-2-sodium alkoxide produce middle control
Make, its end product quality can be significantly improved, and simply accurate, there is preferable application prospect.
At " pesticide intermediate 3,5, the synthesis of 6 trichloropyridine 2-sodium alkoxide " (East China University of Science's master thesis, Wang Li
Red) in document, author uses gas chromatography to be equipped with fid detector to control trichloro-acetic chloride, acrylonitrile, chlorobenzene and additive reaction
Thing content, controls finished product content in reaction last employing high performance liquid chromatography, and in this control method, employing gas chromatography is
Control addition product in first step additive reaction, and high performance liquid chromatography is to control finished product finally, and the ring in course of reaction
Close product 3,5,6-trichloropyridine-2-ketone the most not control, be unfavorable for improving productivity.Document " trichloro pyridyl sodium alcoholate
Study on the synthesis " in (Hangzhou chemical industry, 2004.34 (1)), the maximum output of trichloro pyridyl sodium alcoholate is 68.5%.
At " study on the synthesis of 3,5,6-trichloropyridine-2-sodium alkoxide " (" Hebei University of Technology's journal " the 1st phase in 2012) literary composition
In offering, author is also to use gas chromatography to control, and the method error is big, it is impossible to accurately reflects the extent of reaction, and is also to control
Additive reaction product, but to intermediate product 3,5,6-trichloropyridine-2-ketone the most do not control.
Summary of the invention
For weak point present in art technology, it is an object of the invention to propose a kind of based on 3,3,5,6-tetra-
The detection of chloro-4,4-dihydropyridine-2-ketone controls the method that 3,5,6-trichloropyridine-2-sodium alkoxide produce.
The technical scheme realizing above-mentioned purpose of the present invention is:
A kind of based on 3, the detection of 3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone controls 3,5,6-trichloropyridine-2-sodium alkoxide
The method produced, comprises the steps:
(1) 3,5,6-trichloropyridine-2-sodium alkoxide production processes take sodium alkoxide and produces intermediate sample, according to quality volume
Ratio 40-70mg/50mL, is dissolved in methanol, makes sample solution；Accurately weigh 3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone mark
Quasi-product 40-60mg, makes standard solution according to mass volume ratio 40-70mg/50mL；
(2) sample solution carries out high performance liquid chromatography (HPLC) detection after filtering, detects qualified rear 3,5,6-trichlorine pyrroles
The production process of pyridine-2-sodium alkoxide adds alkali liquor, carries out next step reaction.
Wherein, in described step (1), the sodium alkoxide adding 40～50mg in the methanol solution of every 50ml produces intermediate sample
Product, ultrasonic 0.5 hour, make sample all dissolve, make sample solution.
Wherein, in described step (2), the flowing of high performance liquid chromatography detection is methanol mutually: water: glacial acetic acid, its volume ratio
Being 75～85:25～15:0.5, the wavelength of detection is 302nm, and sample introduction flow is 0.5～2ml/min, and column temperature is 30～40 DEG C,
Chromatographic column is C18 chromatographic column.
Preferably, in described step (2), the flowing of high performance liquid chromatography detection is methanol mutually: water: glacial acetic acid, its volume
Ratio is 80:20:0.5, and the wavelength of detection is 302nm, and sample introduction flow is 1ml/min, and column temperature is 35 DEG C.
The method that the present invention proposes, the main trichloro-acetic chloride method used during current chlopyrifos produces that is directed to produces work
Skill.Trichloro-acetic chloride method is trichloro-acetic chloride with acrylonitrile under catalyst action, through addition, cyclization, aromatization chemical conversion salt, then by
Trichloro pyridyl sodium alcoholate and diethylaluminum monochloride synthesis prepare chlopyrifos.The intermediate preparing trichloro pyridyl sodium alcoholate is 3,3,5,6-tetra-
Chloro-4,4-dihydropyridine-2-ketone, by controlling 3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone transforming degree and under controlling
One step adds the opportunity of alkali liquor, is the effective control method improving target product yield.By controlling intermediate 3,3,5,6-tetra-
The content of chloro-4,4-dihydropyridine-2-ketone, to control the extent of reaction, can be effectively improved yield to about 89%.
Wherein, 3,5,6-trichloropyridine-2-sodium alkoxide are to be obtained with acrylonitrile reactor by trichloro-acetic chloride, and reaction is carried out
Sample the when of 12 hours.
In step (2), high performance liquid chromatography detection sodium alkoxide produces intermediate sample, compares with the chromatogram of standard substance and tries to achieve
3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone content, in sample 3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone content
More than 85%, then it is qualified to be considered as；3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone content is 1-84%, then be considered as defective,
Extend trichloro-acetic chloride and acrylonitrile reactor time.
The beneficial effects of the present invention is:
Sample detection is quick, can complete the detection of sample, determine to add the opportunity of alkali in 20 minutes, control in time to react into
Degree.
The method that the present invention proposes, controls low cost, accurately and reliably.
Quickly, accurately, the quality control in producing for trichloro pyridyl sodium alcoholate provides guarantee to detection method, has preferable work
Industry controls application prospect.
Accompanying drawing explanation
Fig. 1 is embodiment 1 chromatogram.
Fig. 2 is embodiment 2 chromatogram.
Detailed description of the invention
Now with following most preferred embodiment, the present invention is described, but is not limited to the scope of the present invention.
If no special instructions, the means in embodiment all use this area routine techniques means.
In embodiment,
High performance liquid chromatograph: LC-10AT chromatographic work station: Hp-chem
Detector: variable-wavelenght detector (VWD)
Medicine: 3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone sterling, methanol, glacial acetic acid, redistilled water
Testing conditions:
Chromatographic column: Kromasil, C18,4.6mm × 250mm, 5 μm
Fixing phase: Zorbax-ODS flowing phase: methanol: water: glacial acetic acid=80:20:0.5 (volume ratio)
Flow velocity: 1ml/min detects wavelength: 302nm column temperature: 35 DEG C
Sample size: 10 microlitres (50mg/50ml)
Embodiment 1:
Sample constantly chloracetyl chloride is little with acrylonitrile reactor 12.
1,3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone standard substance about 0.0512g is accurately weighed in 50ml volumetric flask
In, add methanol and dissolve, ultrasonic 30min on supersonic oscillations instrument, by methanol constant volume, shake up standby；
2, weigh control sample 0.0639 in the middle of 3,5,6-trichloropyridine-2-sodium alkoxide and, in 50ml volumetric flask, add methanol
Dissolve, ultrasonic 30min on supersonic oscillations instrument, by methanol constant volume, filter standby after shaking up.
3, draw above-mentioned solution, inject chromatograph of liquid, measure chromatogram and calculate peak area (Fig. 1).With standard substance
Chromatogram compares tries to achieve 3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone content,
4, result is 86.36%, and content is qualified.The detection time was less than 20 minutes.
5, sodium alkoxide is reacted into next step: add 5% sodium hydroxide solution, to generate 3, and 5,6-trichloropyridine-2-sodium alkoxide.
The productivity of final 3,5,6-trichloropyridine-2-sodium alkoxide is 87.59%, purity 90.19%.
Embodiment 2
Liquid Detection condition is with embodiment 1.Sample size: 10 microlitres (50mg/50ml).At chloracetyl chloride and acrylonitrile reactor
12 little sample constantly.
1, weighing 3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone standard substance about 0.106g, in 50ml volumetric flask, adds
Methanol dissolves, and ultrasonic 30min on supersonic oscillations instrument, by methanol constant volume, shakes up standby；
2, weigh control sample 0.1327 in the middle of 3,5,6-trichloropyridine-2-sodium alkoxide and, in 50ml volumetric flask, add methanol
Dissolve, ultrasonic 30min on supersonic oscillations instrument, by methanol constant volume, filter standby after shaking up.
3, draw above-mentioned solution, inject chromatograph of liquid (Fig. 2), measure content.
4, result is 89.42%, and content is qualified.
5, sodium alkoxide is reacted into next step, adds 5% sodium hydroxide solution, to generate 3, and 5,6-trichloropyridine-2-sodium alkoxide.
The productivity of final 3,5,6-trichloropyridine-2-sodium alkoxide is 90.36%, purity 92.53%.
Embodiment 3
Liquid Detection condition is with embodiment 1.Sample size: 10 microlitres (50mg/50ml).At chloracetyl chloride and acrylonitrile reactor
12 little sample constantly.
1, weighing 3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone standard substance about 0.0521g, in 50ml volumetric flask, adds
Enter the phase that flows (methanol: water: glacial acetic acid=80:20:0.5 (volume ratio)) to dissolve, ultrasonic 30min on supersonic oscillations instrument, use
Flowing phase constant volume, shakes up standby；
2, weigh control sample 0.0673 in the middle of 3,5,6-trichloropyridine-2-sodium alkoxide and, in 50ml volumetric flask, add flowing
Phase (methanol: water: glacial acetic acid=80:20:0.5 (volume ratio)) is dissolved, ultrasonic 30min on supersonic oscillations instrument, by flowing phase
Constant volume, filters standby after shaking up.
3, draw above-mentioned solution, inject chromatograph of liquid, measure content.
4, result is 90.31%, and content is qualified.
5, sodium alkoxide is reacted into next step, adds 5% sodium hydroxide solution, to generate 3, and 5,6-trichloropyridine-2-sodium alkoxide.
The productivity of final 3,5,6-trichloropyridine-2-sodium alkoxide is 88.65%, purity 90.63%.
Embodiment 4
Liquid Detection condition is with embodiment 1.Sample size: 10 microlitres (50mg/50ml).At chloracetyl chloride and acrylonitrile reactor
12 little sample constantly.
1, weighing 3,3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone standard substance about 0.0521g, in 50ml volumetric flask, adds
Enter methanol to dissolve, ultrasonic 30min on supersonic oscillations instrument, by methanol constant volume, shake up standby；
2, weigh control sample 0.0673 in the middle of 3,5,6-trichloropyridine-2-sodium alkoxide and, in 50ml volumetric flask, add methanol
Dissolve, ultrasonic 30min on supersonic oscillations instrument, by methanol constant volume, filter standby after shaking up.
3, draw above-mentioned solution, inject chromatograph of liquid, measure content.
4, result is 86.39%, and content is qualified.
5, sodium alkoxide is reacted into next step.Add 5% sodium hydroxide solution, to generate 3,5,6-trichloropyridine-2-sodium alkoxide.
The productivity of final 3,5,6-trichloropyridine-2-sodium alkoxide is 87.36%, purity 91.32%.
Above embodiment is only to be described the preferred embodiment of the present invention, not carries out the scope of the present invention
Limiting, on the premise of designing spirit without departing from the present invention, this area ordinary skill technical staff is to technical scheme
The various modification made and improvement, all should fall in the protection domain that claims of the present invention determines.
Claims (2)
1. one kind based on 3, and it is raw that the detection of 3,5,6-tetra-chloro-4,4-dihydropyridine-2-ketone controls 3,5,6-trichloropyridine-2-sodium alkoxide
The method produced, it is characterised in that comprise the steps:
(1) 3, taking 3 in 5,6-trichloropyridine-2-sodium alkoxide production processes, 5,6-trichloropyridine-2-sodium alkoxide produce intermediate sample
Product, described 3,5,6-trichloropyridine-2-sodium alkoxide are to be obtained by trichloro-acetic chloride and acrylonitrile reactor, and reaction carries out 12 hours
When sampling, be dissolved in methanol according to mass volume ratio 40-70mg/50mL, make sample solution；Accurately weigh 3,3,5,6-tetra-
Chloro-4,4-dihydropyridine-2-ketone standard substance 40-60mg, makes standard solution according to mass volume ratio 40-70mg/50mL；
(2) sample solution carries out high performance liquid chromatography detection after filtering, detects qualified rear 3,5,6-trichloropyridine-2-sodium alkoxide
Production system adds alkali liquor, carries out next step reaction；
Wherein, the chromatographic column of high performance liquid chromatography detection is C18 chromatographic column, and flowing is methanol mutually: water: glacial acetic acid, its volume ratio
For 80:20:0.5, the wavelength of detection is 302nm, and sample introduction flow is 1ml/min, and column temperature is 35 DEG C.
Method the most according to claim 1, it is characterised in that in described step (1), adds in the methanol solution of every 50ml
The 3 of 40～50mg, 5,6-trichloropyridine-2-sodium alkoxide produce intermediate sample, ultrasonic 0.5 hour, make sample all dissolve, make
Sample solution.
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| Title |
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| 3，5，6-三氯吡啶-2-醇钠的合成;刘延娜;《中国优秀硕士学位论文全文数据库 工程科技I辑》;20080915(第09期);第20页第1段、第22页3.2.1.1部分、第32页3.2.4.1部分、第34-35页第3.2.4.3部分、第42-43页第4.3部分 * |
| ３，５，６－三氯吡啶－２－醇钠的工艺优化;赵丹凤等;《河北工业大学学报》;20120228;第41卷(第1期);第48-52页 * |
| 3_5_6_三氯吡啶_2_醇钠的合成;李培国;《浙江化工》;20041231;第35卷(第3期);第16-18页 * |
| 农药中间体3,5,6-三氯吡啶-2-醇钠研究进展;刘宁 等;《现代农药》;20070830;第6卷(第4期);第14-18页 * |
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