CN101597265B - Method for synthesizing bromacil technical - Google Patents
Method for synthesizing bromacil technical Download PDFInfo
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- CN101597265B CN101597265B CN2009101001392A CN200910100139A CN101597265B CN 101597265 B CN101597265 B CN 101597265B CN 2009101001392 A CN2009101001392 A CN 2009101001392A CN 200910100139 A CN200910100139 A CN 200910100139A CN 101597265 B CN101597265 B CN 101597265B
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- bromacil
- reaction
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- technical
- synthesizing
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- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title abstract description 12
- 230000002194 synthesizing effect Effects 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000010189 synthetic method Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 7
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 4
- 238000001035 drying Methods 0.000 claims 2
- 238000009413 insulation Methods 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 14
- 239000002904 solvent Substances 0.000 abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract description 2
- 230000002363 herbicidal effect Effects 0.000 abstract description 2
- 239000004009 herbicide Substances 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000001632 sodium acetate Substances 0.000 abstract description 2
- 235000017281 sodium acetate Nutrition 0.000 abstract description 2
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 238000004904 shortening Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000005516 engineering process Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- JXSCGNUFPLOCLH-UHFFFAOYSA-N 3-butan-2-yl-6-methyl-1h-pyrimidine-2,4-dione Chemical compound CCC(C)N1C(=O)C=C(C)NC1=O JXSCGNUFPLOCLH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- XBCXJKGHPABGSD-UHFFFAOYSA-N methyluracil Natural products CN1C=CC(=O)NC1=O XBCXJKGHPABGSD-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000010795 gaseous waste Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a method for synthesizing herbicide, in particular to a method for synthesizing bromacil technical. The reaction formula in the method for synthesizing the bromacil technical is as the above. The method adopts water as solvent, leads the whole reaction to be performed in water phase, is clean and environment friendly, solves the problem that solvent can not be reclaimed for multiple times when ethylic acid is adopted as solvent in the prior art, does not require sodium acetate and need no side pressure to remove the solvent, thereby shortening the production period; meanwhile, HBr generated in an oxidation reaction of hydrogen peroxide with low price is adopted, and the utilization ratio of bromine is improved to 98 percent from 45 percent of the prior art, so that the whole reaction can be better carried out towards the positive reaction, the yield is improved to 98 percent from 92 percent of the prior art, and the cost of raw materials and production is reduced.
Description
Technical field
The present invention relates to a kind of synthetic method of weedicide, specifically is exactly the synthetic method of bromacil technical.
Background technology
Bromacil is a kind of nonselective herbicide, is mainly used in to prevent and kill off the noncrop area oranges and tangerines garden, perennial gramineous weeds in ground such as pinery and annual grassy weeds.Its chemical name is 5-bromo-3-sec-butyl-6-methyl uracil, and common name is bromacil, and its structural formula is:
At present, the domestic synthetic method that generally adopts is to be starting raw material with 3-sec-butyl-6-methyl uracil, makes solvent with acetic acid, adds sodium acetate buffer, and the bromine reaction with excessive finally makes bromacil technical.But there is following defective in this method: the one, and recovered solvent acetic acid has loss; The 2nd, the acetic acid that reclaims can reduce the yield of reaction greatly after applying mechanically more than 4 times, can not repeatedly repeat to apply mechanically, and the bromine utilization ratio is low excessively simultaneously, makes whole technology material cost high; The 3rd, the discharge of wastewater acidity problem that exceeds standard.
Summary of the invention
The objective of the invention is to for overcoming the deficiencies in the prior art and provide a kind of synthetic method of new bromacil technical, this synthetic method more clean environment firendly, cost is low, the bromine utilization ratio is higher.
For achieving the above object, the invention discloses a kind of synthetic method of bromacil technical, its chemical equation is as follows:
Compared with prior art, the present invention has following advantage:
(1) novel method adopts water to make solvent, entire reaction is carried out at aqueous phase, clean environment firendly, the solvent problem used of recovery set repeatedly when having solved original process using acetic acid and making solvent, simultaneously need not use sodium-acetate, need not secondary pressure-off and go out solvent, shortened the production cycle, reduced material cost and production cost.
(2) novel method adopts the HBr that generates in the cheap hydrogen peroxide oxidation reaction, the bromine utilization ratio of original technology 45% is brought up to 98%, entire reaction is better carried out towards the positive reaction direction, and yield brings up to 98% by 92% of original technology, reduces the material cost of knowing clearly.
(3) novel method is owing to bromine utilization ratio height, and institute adds hydrogen peroxide simultaneously bleaching action, and products obtained therefrom is a pure white, and original technology is excessive because of bromine, and products obtained therefrom is faint yellow.
(4) novel method products obtained therefrom quality better, because of the bromide anion that has only trace in the reaction process oxidizedly not fall, the NaBr that generates trace with liquid caustic soda has also been water-washed away, so the not tolerant content of acetone is lower than 0.1% in the product, and the acetone of original technology is not tolerant more than 0.3%.
(5) novel method is a clean and environment-friendly technology, and bromine utilization ratio height can not produce HBr tail gas in the reaction process fully, and the mother liquor after filtering simultaneously is neutral, only contains the Sodium Bromide of trace, and no industrial gaseous waste produces, the easy environmental protection treatment qualified discharge of waste water.
Embodiment
The chemical equation of bromacil technical synthetic method of the present invention is as follows:
Have multiple reactions steps can realize above-mentioned chemical reaction, concrete reaction process is referring to following
Specific embodiment:
Concrete case 1: with 63.15g content is 95%, 3-sec-butyl-6-the methyl uracil of M=182 and 350ml water drop in the 500ml four-hole boiling flask, be warming up to 70 ℃～120 ℃, preferred 85 ℃, slowly drip 27.3g bromine (content 99%), dropwised the back insulated and stirred 15 minutes, at 70 ℃～120 ℃, preferred 85 ℃ are continued slowly to drip the 18.5g hydrogen peroxide down, the back insulated and stirred that finishes 2 hours is cooled to 45 ℃, and dripping about 0.9g liquid caustic soda accent system pH value is 7, be cooled to 25 ℃, stir after washing filtration half an hour, oven dry gets the white crystalline solid bromacil of content 〉=97% 87.9g.(M=261), the yield of this reaction can reach 98%.
Concrete case 2: with 63.15g content be 95%, 3-sec-butyl-6-methyl uracil and the 350ml water of M=182 drops in the 500ml four-hole boiling flask, be warming up to 70 ℃～120 ℃, preferred 85 ℃, slowly Dropwise 5 4g bromine (content 99%) dropwised the back insulated and stirred 2 hours, be cooled to 45 ℃, dripping about 45g liquid caustic soda accent system pH value is 7, is cooled to 25 ℃, stirs after washing filtration half an hour, oven dry gets the faint yellow crystalline solid bromacil of content 〉=96% 87.9g.(M=261), the yield of this reaction can reach 90%.
Concrete case 3: with 63.15g content is 95%, 3-sec-butyl-6-the methyl uracil of M=182 and 350ml water drop in the 500ml four-hole boiling flask, be warming up to 70 ℃～120 ℃, preferred 85 ℃, slowly drip 27.3g bromine (content 99%), dropwised the back insulated and stirred 15 minutes, at 70 ℃～120 ℃, preferred 85 ℃ are continued slowly to drip 126g aqueous sodium hypochlorite solution (content 10%) down, the back insulated and stirred that finishes 2 hours is cooled to 45 ℃, and dripping 30% hydrochloric acid accent system pH value is 7, be cooled to 25 ℃, stir after washing filtration half an hour, oven dry gets the white crystalline solid bromacil of content 〉=95% 83g.(M=261), the yield of this reaction can reach 92%.
Concrete case 4: with 63.15g content is 95%, 3-sec-butyl-6-the methyl uracil of M=182 and 350ml water drop in the 500ml four-hole boiling flask, be warming up to 70 ℃～120 ℃, preferred 85 ℃, slowly drip 30g bromine (content 99%), dropwised the back insulated and stirred 15 minutes, at 70 ℃～120 ℃, preferred 85 ℃ are continued slowly to drip 24g hydrogen peroxide (content 30%) down, the back insulated and stirred that finishes 2 hours is cooled to 45 ℃, and dripping about 0.9g liquid caustic soda accent system pH value is 7, be cooled to 25 ℃, stir after washing filtration half an hour, oven dry gets the white crystalline solid bromacil of content 〉=96% 87.9g.(M=261), the yield of this reaction can reach 98%.The bromacil color and luster that this technology obtains is whiter.
Concrete case 5: with 63.15g content be 95%, 3-sec-butyl-6-methyl uracil and the 350ml toluene of M=182 drops in the 500ml four-hole boiling flask, be warming up to 105 ℃, slowly drip 27.3g bromine (content 99%), dropwised the back insulated and stirred 15 minutes, 105 ℃ are continued slowly to drip 18g hydrogen peroxide (content 30%) down, the back insulated and stirred that finishes 2 hours, be cooled to 45 ℃, dripping about 0.9g liquid caustic soda accent system pH value is 7, be cooled to 25 ℃, stir after washing filtration half an hour, oven dry gets the white crystalline solid bromacil of content 〉=97% 82.5g.(M=261), the yield of this reaction can reach 93%.
Claims (2)
1. the synthetic method of a bromacil technical is characterized in that reactions steps is as follows:
1), in the 3-sec-butyl-the 6-6-Methyl Uracil is water-soluble, is mixed with the aqueous solution;
2), temperature is risen to 70～120 ℃, in the aqueous solution, drip bromine;
3), be 70～120 ℃ and drip hydrogen peroxide down in temperature;
4), insulation reaction is 2 hours;
5), be cooled to 45 ℃, dropwise liquid accent system pH to 7;
6), continue to be cooled to 20 ℃～25 ℃, be incubated 0.5 hour;
7), filter, drying, oven dry obtains 5-bromo-3-sec-butyl-6-6-Methyl Uracil.
2. the synthetic method of a bromacil technical is characterized in that reactions steps is as follows:
1), in the 3-sec-butyl-the 6-6-Methyl Uracil is water-soluble, is mixed with the aqueous solution;
2), temperature is risen to 70～100 ℃, in the aqueous solution, drip bromine;
3), be 70～100 ℃ and drip aqueous sodium hypochlorite solution down in temperature;
4), insulation reaction is 2 hours;
5), be cooled to 45 ℃, dropwise liquid accent system pH to 7;
6), continue to be cooled to 20 ℃～25 ℃, be incubated 0.5 hour;
7), filter, drying, oven dry obtains 5-bromo-3-sec-butyl-6-6-Methyl Uracil.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101001392A CN101597265B (en) | 2009-06-24 | 2009-06-24 | Method for synthesizing bromacil technical |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101001392A CN101597265B (en) | 2009-06-24 | 2009-06-24 | Method for synthesizing bromacil technical |
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| CN101597265A CN101597265A (en) | 2009-12-09 |
| CN101597265B true CN101597265B (en) | 2011-01-26 |
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Owner name: YIFAN BIOTECHNOLOGY GROUP CO., LTD. Free format text: FORMER NAME: ZHEJIANG YIFAN CHEMICAL CO., LTD. |
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Address after: 325000 Zhongxing Road, Wenzhou Industrial Park, Zhejiang, 136 Patentee after: YIFAN BIOTECHNOLOGY GROUP CO., LTD. Address before: 325000 No. 136 Zhongxing Road, poverty alleviation development zone, Longwan District, Wenzhou, Zhejiang Patentee before: Zhejiang Yifan Chemical Co.,Ltd. |
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Application publication date: 20091209 Assignee: Jiangsu Yunfan Chemical Co., Ltd. Assignor: YIFAN BIOTECHNOLOGY GROUP CO., LTD. Contract record no.: 2013320000757 Denomination of invention: Method for synthesizing bromacil technical Granted publication date: 20110126 License type: Exclusive License Record date: 20131108 |
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Assignee: JIANGSU YUNFAN CHEMICAL Co.,Ltd. Assignor: YIFAN BIOTECHNOLOGY GROUP Co.,Ltd. Contract record no.: 2013320000757 Date of cancellation: 20200820 |
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Effective date of registration: 20200925 Address after: No.006 photovoltaic Road, new chemical materials Park, Ningdong energy and chemical base, Ningdong Town, Lingwu City, Yinchuan City, Ningxia Hui Autonomous Region, 750409 Patentee after: Ningxia Yifan Biotechnology Co., Ltd Address before: 325000 Zhongxing Road, Wenzhou Industrial Park, Zhejiang, 136 Patentee before: YIFAN BIOTECHNOLOGY GROUP Co.,Ltd. |
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