CN104803930A - 一种氯溴异氰尿酸的生产方法 - Google Patents
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 239000002253 acid Substances 0.000 title abstract 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 6
- 239000008367 deionised water Substances 0.000 claims abstract description 6
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 6
- 239000012074 organic phase Substances 0.000 claims abstract description 6
- 229920006395 saturated elastomer Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- DZZOJKGQQSORQI-UHFFFAOYSA-N N1C(=O)NC(=O)NC1=O.ClBr Chemical compound N1C(=O)NC(=O)NC1=O.ClBr DZZOJKGQQSORQI-UHFFFAOYSA-N 0.000 claims description 22
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 235000002639 sodium chloride Nutrition 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000010025 steaming Methods 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- HLSCJPDXQCURMT-UHFFFAOYSA-N 7,9-dihydro-3H-purine-2,6,8-trione oxalonitrile Chemical compound N1C(=O)NC=2NC(=O)NC2C1=O.N#CC#N HLSCJPDXQCURMT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OKNPHOXYVYNIDL-UHFFFAOYSA-N 1-bromo-3-chloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)NC(=O)N(Br)C1=O OKNPHOXYVYNIDL-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- NYSDRHDGXAQTPT-UHFFFAOYSA-N N1C(=O)NC(=O)NC1=O.[Cl].[Br] Chemical compound N1C(=O)NC(=O)NC1=O.[Cl].[Br] NYSDRHDGXAQTPT-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- -1 cyanuric acid sodium salt Chemical class 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/36—Only oxygen atoms having halogen atoms directly attached to ring nitrogen atoms
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明公开了一种氯溴异氰尿酸的生产方法。本发明的技术方案要点为：一种氯溴异氰尿酸的生产方法，具体步骤为：首先将氰尿酸和三乙胺溶于四氢呋喃溶剂中，然后于0℃滴加液溴并通入氯气，反应完全后蒸除四氢呋喃，剩余产物用乙酸乙酯溶解，再用去离子水和饱和食盐水交替洗涤两次，有机相用无水硫酸钠干燥后于30℃真空蒸馏得到产品氯溴异氰尿酸。本发明制备成本低，无有害废弃物产生，符合绿色生产理念；避免了使用价格昂贵的金属催化剂；工艺简单，操作简便，工艺流程短，效率高，易于控制，适合大规模生产。
Description
技术领域
本发明属于氯溴异氰尿酸的合成技术领域，具体涉及一种氯溴异氰尿酸的生产方法。
背景技术
氯溴异氰尿酸，俗称消菌灵，英文通用名为：Bromochlorocyanuric Acid。氯溴异氰尿酸原药为白色粉末或白色结晶，含溴29%-30%，含氯12%-13%，水中溶解度为0.4%(25℃)，易溶于水，在有机溶剂中的溶解度较小，是一种广谱、高效、无公害及与环境相容的新型农药，兼有内吸和保护双重作用，能快速有效地杀灭危害作物的真菌、细菌、病毒，对作物疑难病害有特效。常用于防治烟草野火病及水稻、瓜果、蔬菜、花生、花舟上的细菌、真菌性病害。
目前氯溴异氰尿酸的合成工艺存在着工艺流程长、收率低等缺点。已报道的氯溴异氰尿酸制备方法主要是在氰尿酸悬浮液中加入次氯酸钠、次溴酸钠，进行氯化、溴化反应，经处理后得到氯溴异氰尿酸，但该方法原料相对价格较高且不易获得。或者先将尿素和氯化铵脱氨环化形成氰尿酸，然后将氰尿酸悬浮液中通入氢氧化钠，合成为氰尿酸钠盐，再依次通入氯气氯化、通入溴气溴化，制备氯溴氰尿酸，但是这种方法由于氰尿酸在溶液中不容易混合均匀，产率较低。
发明内容
本发明解决的技术问题是提供了一种氯溴异氰尿酸的生产方法，该生产方法操作简单易行，原料易得，反应效率高，重复性好，利用此方法制备氯溴异氰尿酸克服了反应周期长的缺点，并且能够获得可观的商业价值。
本发明为解决上述技术问题采用如下技术方案，一种氯溴异氰尿酸的生产方法，其特征在于具体步骤为：首先将氰尿酸和三乙胺溶于四氢呋喃溶剂中，然后于0℃滴加液溴并通入氯气，反应完全后蒸除四氢呋喃，剩余产物用乙酸乙酯溶解，再用去离子水和饱和食盐水交替洗涤两次，有机相用无水硫酸钠干燥后于30℃真空蒸馏得到产品氯溴异氰尿酸，合成过程中的反应方程式为：
。
本发明的有益效果是：1、制备成本低，无有害废弃物产生，符合绿色生产理念；2、避免了使用价格昂贵的金属催化剂；3、工艺简单，操作简便，工艺流程短，效率高，易于控制，适合大规模生产。
附图说明
图1是本发明实施例1制得的氯溴异氰尿酸的UV图，图2是本发明实施例1得的氯溴异氰尿酸的HPLC图。
具体实施方式
以下通过实施例对本发明的上述内容做进一步详细说明，但不应该将此理解为本发明上述主题的范围仅限于以下的实施例，凡基于本发明上述内容实现的技术均属于本发明的范围。
实施例1
称取氰尿酸12.9g和三乙胺30.3g溶于200ml 四氢呋喃溶剂中，于0℃缓慢滴加液溴9.6g并通入4.3g氯气，反应完全后蒸除四氢呋喃，剩余产物用300ml乙酸乙酯溶解，然后用去离子水（150ml×2）洗涤，饱和食盐水（150ml×2）洗涤，有机相用无水硫酸钠干燥后于30℃时真空蒸馏，得产品氯溴异氰尿酸20g。
图1是本实施例制得的氯溴异氰尿酸的UV图，通过岛津UV-2201紫外分析仪对氯溴异氰尿酸进行全波长扫描发现，其最大吸收波长约在215nm，说明有共轭双肩结构的存在；图2是本实施例制得的氯溴异氰尿酸的高效液相色谱图，其中条件为流动相：V（甲醇）：V(水)=80:20，波长：200nm，流速：0.8ml/min，称取0.05g样品溶于50ml容量瓶中，甲醇定溶，进样量为5ml。
实施例2
称取氰尿酸13g和三乙胺31g溶于200ml 四氢呋喃溶剂中，于0℃缓慢滴加液溴10.1g并通入4.5g氯气，反应完全后蒸除四氢呋喃，剩余产物用300ml乙酸乙酯溶解，然后用去离子水（150ml×2）洗涤，饱和食盐水（150ml×2）洗涤，有机相用无水硫酸钠干燥后于30℃时真空蒸馏，得产品氯溴异氰尿酸20.3g。
实施例3
称取氰尿酸13.5g和三乙胺31.7g溶于200ml 四氢呋喃溶剂中，于0℃缓慢滴加液溴10.4g并通入4.6g氯气，反应完全后蒸除四氢呋喃，剩余产物用300ml乙酸乙酯溶解，然后用去离子水（150ml×2）洗涤，饱和食盐水（150ml×2）洗涤，有机相用无水硫酸钠干燥后于30℃时真空蒸馏，得产品氯溴异氰尿酸20.5g。
以上显示和描述了本发明的基本原理，主要特征和优点，在不脱离本发明精神和范围的前提下，本发明还有各种变化和改进，这些变化和改进都落入要求保护的本发明的范围。
Claims (1)
1.一种氯溴异氰尿酸的生产方法，其特征在于具体步骤为：首先将氰尿酸和三乙胺溶于四氢呋喃溶剂中，然后于0℃滴加液溴并通入氯气，反应完全后蒸除四氢呋喃，剩余产物用乙酸乙酯溶解，再用去离子水和饱和食盐水交替洗涤两次，有机相用无水硫酸钠干燥后于30℃真空蒸馏得到产品氯溴异氰尿酸，合成过程中的反应方程式为：
。
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2075979A (en) * | 1934-03-15 | 1937-04-06 | Rca Corp | Amplifying or rectifying device |
| US3147254A (en) * | 1956-08-06 | 1964-09-01 | Drug Res Inc | Halogenated cyanuric acids and their salts |
| US3668204A (en) * | 1970-08-21 | 1972-06-06 | Fmc Corp | Chlorination of cyanuric acid |
| CN1337396A (zh) * | 2001-08-31 | 2002-02-27 | 天津大学 | 溴氯异氰尿酸消毒灭菌剂的制备方法 |
| WO2003050237A2 (en) * | 2001-12-12 | 2003-06-19 | New York University | Triazine library with linkers |
| CN102746245A (zh) * | 2012-07-25 | 2012-10-24 | 河南银田精细化工有限公司 | 一种氯溴异氰尿酸的生产工艺 |
-
2015
- 2015-05-07 CN CN201510228646.XA patent/CN104803930B/zh active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2075979A (en) * | 1934-03-15 | 1937-04-06 | Rca Corp | Amplifying or rectifying device |
| US3147254A (en) * | 1956-08-06 | 1964-09-01 | Drug Res Inc | Halogenated cyanuric acids and their salts |
| US3668204A (en) * | 1970-08-21 | 1972-06-06 | Fmc Corp | Chlorination of cyanuric acid |
| CN1337396A (zh) * | 2001-08-31 | 2002-02-27 | 天津大学 | 溴氯异氰尿酸消毒灭菌剂的制备方法 |
| WO2003050237A2 (en) * | 2001-12-12 | 2003-06-19 | New York University | Triazine library with linkers |
| CN102746245A (zh) * | 2012-07-25 | 2012-10-24 | 河南银田精细化工有限公司 | 一种氯溴异氰尿酸的生产工艺 |
Non-Patent Citations (1)
| Title |
|---|
| 许静: "氰尿酸及其氯代衍生物的合成与研究", 《南京林业大学硕士学位论文》 * |
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