CN102161630A - Industrial preparation method of 2,2-dibromo-2-nitrilo-propionamide - Google Patents
Industrial preparation method of 2,2-dibromo-2-nitrilo-propionamide Download PDFInfo
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- CN102161630A CN102161630A CN2011100539225A CN201110053922A CN102161630A CN 102161630 A CN102161630 A CN 102161630A CN 2011100539225 A CN2011100539225 A CN 2011100539225A CN 201110053922 A CN201110053922 A CN 201110053922A CN 102161630 A CN102161630 A CN 102161630A
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- bromine
- hydrogen peroxide
- cyanoacetamide
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- dibromo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 229940080818 propionamide Drugs 0.000 title abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 106
- 238000006243 chemical reaction Methods 0.000 claims abstract description 58
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 56
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 55
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 55
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 238000001914 filtration Methods 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 239000012452 mother liquor Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 abstract description 16
- 239000002994 raw material Substances 0.000 abstract description 10
- 239000000047 product Substances 0.000 description 21
- 239000000463 material Substances 0.000 description 7
- 230000008901 benefit Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- 241000192700 Cyanobacteria Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UUIVKBHZENILKB-UHFFFAOYSA-N 2,2-dibromo-2-cyanoacetamide Chemical compound NC(=O)C(Br)(Br)C#N UUIVKBHZENILKB-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000195620 Euglena Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000003619 algicide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an industrial preparation method of 2,2-dibromo-2-nitrilo-propionamide. The preparation method comprises the following steps: adding cyanoacetamide and solvent in a reaction container, dropping bromine and hydrogen peroxide under stirring; and continuously reacting for a certain time after dropping, and filtering to obtain 2,2-dibromo-2-nitrilopropionamide, wherein the molar ratio of cyanoacetamide to bromine to hydrogen peroxide is 1:(1.01-1.08):(1.0-1.2). By adopting the industrial preparation method of 2,2-dibromo-2-nitrilopropionamide, the consumption of a bromine raw material can be reduced and the production cost can be reduced.
Description
Technical Field
The invention relates to the technical field of chemical production, in particular to an industrial preparation method of 2, 2-dibromo-2-nitrilopropionamide.
Background
2, 2-dibromo-2-nitrilopropionamide (DBNPA) is an efficient industrial bactericide, algicide and water treatment agent, has the characteristics of broad spectrum, high efficiency, easy degradation, no residue, no pollution to the environment and the like, can be used for preventing bacteria and algae from growing and propagating in lubricating oil, paper pulp, wood, coating and plywood for papermaking, industrial circulating water cooling and metal processing, and can be used as a slurry control agent to be widely applied to paper mill slurry and circulating cooling water systems. The product can kill bacteria, fungi, yeast, cyanobacteria (blue-green algae) and euglena, is a quick bactericide, can be quickly decomposed in an aqueous environment, is safe to the environment, and has wide application prospect and great commercial value.
The prior art discloses some synthetic schemes for DBNPA. Earlier synthesis of 2, 2-dibromo-2-nitrilopropionamide (DBNPA) using bromate or chlorate as the oxidizing agent, such as disclosed in USP3751444, Israeli Patent 4611258, etc. However, a large amount of by-product sodium salt is generated in the production process of the method, the product is not easy to separate, the filtrate cannot be reused, the product purity is low, and the discharge amount of waste liquid is large. EP0308184 discloses a synthesis method of 2, 2-dibromo-2-nitrilopropionamide, which takes hydrogen peroxide as an oxidant, continuously heats at the temperature of 80-100 ℃, and quickly reacts within 10-30min of reaction time to prepare DBNPA. The yield can reach 79.7-89.7% by taking water as a solvent, and the reaction yield can reach 92.7-100.8% by taking filtrate as the solvent, but the method has high reaction temperature, products are easy to decompose, the products are unstable, the reaction yield of different batches is unstable, and the difference is 10% at most.
In order to solve the problems, the patent with the publication number of CN101781233A discloses a synthesis method of 2, 2-dibromo-2-cyanoacetamide (also called 2, 2-dibromo-2-nitrilopropionamide), which adopts cyanoacetamide as a raw material, adds cyanoacetamide and a solvent (water or solution) into a reactor, dropwise adds bromine under stirring at the reaction temperature of 15-45 ℃ for bromination reaction, adopts 30% hydrogen peroxide as an oxidant, and has the reaction time of 0.5-6 h. The raw materials are in the following molar ratio: cyanoacetamide, bromine and hydrogen peroxide in the weight ratio of 1 to 1.1-1.3 to 0.7-0.90. Although the method obtains better DBNPA yield and stability of different batches of yields by prolonging the reaction time and reducing the reaction temperature, the consumption of bromine is greatly increased due to obviously insufficient amount of hydrogen peroxide adopted in the process, and the method is unreasonable in economic aspects if industrialized wide application is realized due to expensive cost of bromine raw materials. And the method still belongs to a synthesis method under a small test strip.
In summary, one of the technical problems that needs to be urgently solved by those skilled in the art is: how to provide an industrial preparation method of 2, 2-dibromo-2-nitrilopropionamide, reduce the consumption of bromine raw materials and reduce the production cost.
Disclosure of Invention
The technical problem to be solved by the invention is to provide an industrial preparation method of 2, 2-dibromo-2-nitrilopropionamide, which can reduce the consumption of bromine raw materials and reduce the production cost.
In order to solve the problems, the invention discloses an industrial preparation method of 2, 2-dibromo-2-nitrilopropionamide, which is characterized by comprising the following steps:
adding cyanoacetamide and a solvent into a reaction vessel, and simultaneously dropwise adding bromine and hydrogen peroxide while stirring;
after the bromine and the hydrogen peroxide are added, continuously reacting for a period of time, and filtering to obtain 2, 2-dibromo-2-nitrilopropionamide;
wherein the molar ratio of the cyanoacetamide to the bromine to the hydrogen peroxide is 1: 1.01-1.08: 1.0-1.2.
Preferably, bromine and hydrogen peroxide are simultaneously dripped under the condition that the reaction temperature is 5-60 ℃.
Preferably, the concentration of the dropwise added hydrogen peroxide is 40-50%.
Preferably, the solvent is selected from: water or mother liquor generated by the reaction.
Preferably, the cyanoacetamide and the solvent are used in the following amount: 1Kg of cyanoacetamide: 3-6L of solvent.
Preferably, after the bromine and the hydrogen peroxide are added, the reaction is continued for 0.2 to 8 hours.
Compared with the prior art, the invention has the following advantages:
according to the method, cyanoacetamide and a solvent are added into a reaction vessel, and DBNPA is prepared in a mode of simultaneously dropwise adding bromine and hydrogen peroxide, wherein the molar ratio of the reaction raw materials, namely cyanoacetamide, bromine and hydrogen peroxide, is 1: 1.01-1.08: 1.0-1.2. By increasing the consumption of hydrogen peroxide, the bromide as a byproduct in the reaction process is almost quantitatively converted into bromine, so that the bromine is most effectively utilized, the consumption of the bromine as a reaction raw material is reduced, the production cost is reduced, the consumption of the bromine is saved by more than 10 percent compared with the prior art, and the economic benefit is very obvious. The method disclosed by the invention improves the reaction yield, and the yield can reach 99.1-105.2%; meanwhile, the operation can be kept stable and the yield is stable.
Furthermore, the concentration of the dropwise added hydrogen peroxide is preferably 50%, the total amount of water in the reaction vessel can be reduced by dropwise adding higher-concentration hydrogen peroxide, and because the reaction product 2, 2-dibromo-2-nitrilopropionamide (DBNPA) is a water-soluble substance, the purification loss of the product caused by dissolving the product in the mother liquor is reduced, and the yield of the product is improved.
In addition, the mother liquor generated by the reaction can be used as a solvent, and the mother liquor generated in the production process is completely recycled, so that no sewage is discharged in the production process, no external water source is polluted, and the green and environment-friendly production line is realized; meanwhile, as part of bromine is dissolved in the mother liquor, compared with water as a solvent, the consumption of bromine can be reduced, and the yield of DBNPA is improved.
Drawings
FIG. 1 is a flow chart of an embodiment of the industrial preparation method of 2, 2-dibromo-2-nitrilopropionamide of the present invention.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, embodiments accompanied with figures are described in further detail below.
Referring to fig. 1, there is shown a flow chart of an embodiment of the industrial process for the preparation of 2, 2-dibromo-2-nitrilopropionamide of the present invention, comprising:
in the preferred embodiment of the invention, bromine (liquid bromine) and hydrogen peroxide are added dropwise at the reaction temperature of 5-60 ℃. Furthermore, the concentration of the dropwise added hydrogen peroxide is 40-50%, the total amount of water in the reaction vessel can be reduced by dropwise adding higher-concentration hydrogen peroxide, and because the reaction product 2, 2-dibromo-2-nitrilopropionamide is a water-soluble substance, the purification loss of the product caused by dissolving the product in the mother liquor is reduced, and the yield of the product is improved. Since the concentration of the commercially available hydrogen peroxide is usually 27.5% and 50%, in a preferred embodiment of the present invention, 50% hydrogen peroxide is directly added dropwise. In other embodiments, other concentrations of hydrogen peroxide may be obtained by blending.
Preferably, the cyanoacetamide and the solvent are used in the following amount: 1Kg of cyanoacetamide: 3-6L of solvent. The solvent is selected from: water or mother liquor generated by the reaction. When the mother liquor generated after the product is filtered in the production is used as a solvent and is completely recycled, the waste water discharge is reduced, no pollution is caused to an external water source, and the green and environment-friendly production line is realized; meanwhile, as partial products are dissolved in the mother liquor, compared with the method using water as a solvent, the method can reduce the consumption of bromine and improve the yield of DBNPA.
In a preferred embodiment of the invention, after the bromine and the hydrogen peroxide are added dropwise, the reaction is continued for 0.2 to 8 hours, and then the filtration is carried out.
The industrial preparation method of the 2, 2-dibromo-2-nitrilopropionamide provided by the invention adopts a mode of simultaneously dripping bromine and hydrogen peroxide, the molar ratio of the used raw materials, namely cyanoacetamide, bromine and hydrogen peroxide is 1: 1.01-1.08: 1.0-1.2, and by increasing the dosage of the hydrogen peroxide, the bromide as a byproduct in the reaction process is almost quantitatively converted into bromine, so that the bromine is utilized most effectively, the dosage of the bromine as a reaction raw material is reduced, the production cost is reduced, the consumption of the bromine is saved by more than 10% compared with the prior art, and the economic benefit is very obvious. It can be understood that although the amount of the hydrogen peroxide is increased, the price of the hydrogen peroxide is lower than that of the bromine, and the cost is slightly influenced. In addition, the method disclosed by the invention improves the reaction yield, the production yield can reach 99.1-105.2%, and the stable operation and the stable yield can be kept.
It should be noted that the reaction temperature of the present invention has a large influence on the reaction yield, and a satisfactory production yield can be obtained by controlling the reaction temperature within the range of 10 to 50 ℃. The reaction time of the present invention also has an influence on the reaction yield, and a satisfactory production yield can be obtained within a preferable range of 0.2 to 7 hours.
In the following, the present invention is further explained by giving several specific examples. In the following examples of the present invention, the molecular weight of each reactant/product is taken as an integer part, and a decimal part is omitted; wherein,
cyanoacetamide (NCCH)2CONH2) Has a molecular weight of 84;
bromine (Br)2) Has a molecular weight of 160;
hydrogen peroxide (H)2O2) Has a molecular weight of 34.
Example 1
1260L of water and 420KG of cyanoacetamide are added into a 2000L reaction kettle, the ratio of cyanoacetamide to solvent is 1: 3 (weight Wt/volume V), the temperature in the reaction kettle is controlled to be 10-50 ℃, and 808KG of bromine and 408KG of hydrogen peroxide with the concentration of 50 percent are simultaneously added dropwise with stirring. And (3) after the two materials are dripped, continuously reacting for 0.2-7 hours, filtering to obtain mother liquor, mechanically using the mother liquor, and filtering to obtain a product 2, 2-dibromo-2-cyanopropionamide (DBNPA), wherein the yield is 99.2%. In this example 1, the molar ratio of cyanoacetamide to bromine to hydrogen peroxide is:
420/84∶808/160∶(1/2×408/34)＝1∶1.01∶1.2
example 2
1680L of water and 420KG of cyanoacetamide are added into a 2000L reaction kettle, the ratio of cyanoacetamide to solvent is 1: 4(Wt/V), the temperature in the kettle is controlled to be 5-60 ℃, and 408Kg of bromine 864KG and 50% hydrogen peroxide are simultaneously dropped into the kettle under stirring. After the two materials are dripped in, the reaction is continued for 0.2 to 7 hours, the mother liquor obtained by filtration is reused, and the yield of the 2, 2-dibromo-2-cyanopropionamide obtained by filtration is 103.6 percent. In this example 2, the molar ratio of cyanoacetamide to bromine to hydrogen peroxide is:
420/84∶864/160∶(1/2×408/34)＝1∶1.08∶1.2
example 3
A2000L reaction kettle is added with 1260L of mother liquor for preparing DBNPA and 420KG of cyanoacetamide, the ratio of cyanoacetamide to solvent is 1: 3(Wt/V), the temperature in the reaction kettle is controlled to be 10-50 ℃, and 808KG of bromine and 50% hydrogen peroxide 374KG are added dropwise while stirring. After the two materials are dripped, the reaction is continued for 0.2 to 7 hours, the filtered mother liquor is reused, the product obtained by filtering is DBNPA, and the yield is 104.8 percent. In this example 3, the molar ratio of cyanoacetamide to bromine to hydrogen peroxide is:
420/84∶808/160∶(1/2×374/34)＝1∶1.01∶1.1
example 4
1680L of mother liquor for preparing DBNPA and 420KG of cyanoacetamide are added into a 2000L reaction kettle, the ratio of cyanoacetamide to solvent is 1: 4(Wt/V), the temperature in the reaction kettle is controlled to be 5-60 ℃, and 864KG of bromine and 50% hydrogen peroxide 374KG are added simultaneously while stirring. After the two materials are dripped, the reaction is continued for 0.2 to 7 hours, the filtered mother liquor is reused, the product obtained by filtering is DBNPA, and the yield is 105.2 percent. In this example 4, the molar ratio of cyanoacetamide to bromine to hydrogen peroxide is:
420/84∶864/160∶(1/2×374/34)＝1∶1.08∶1.1
example 5
1680L of mother liquor for preparing DBNPA and 420KG of cyanoacetamide are added into a 2000L reaction kettle, the ratio of cyanoacetamide to solvent is 1: 4(Wt/V), the temperature in the reaction kettle is controlled to be 5-60 ℃, and 824KG of bromine and 50% hydrogen peroxide 340KG are added simultaneously while stirring. After the two materials are dripped, the reaction is continued for 0.2 to 7 hours, the filtered mother liquor is reused, the product obtained by filtering is DBNPA, and the yield is 105.2 percent. In this example 4, the molar ratio of cyanoacetamide to bromine to hydrogen peroxide is:
420/84∶824/160∶(1/2×340/34)＝1∶1.03∶1.0
example 6
1680L of mother liquor for preparing DBNPA and 420KG of cyanoacetamide are added into a 2000L reaction kettle, the ratio of cyanoacetamide to solvent is 1: 4(Wt/V), the temperature in the reaction kettle is controlled to be 5-60 ℃, and 840KG of bromine and 50% hydrogen peroxide 408KG are added simultaneously while stirring. After the two materials are dripped, the reaction is continued for 0.2 to 7 hours, the filtered mother liquor is reused, the product obtained by filtering is DBNPA, and the yield is 105.2 percent. In this example 4, the molar ratio of cyanoacetamide to bromine to hydrogen peroxide is:
420/84∶840/160∶(1/2×408/34)＝1∶1.05∶1.2
example 7
1680L of mother liquor for preparing DBNPA and 420KG of cyanoacetamide are added into a 2000L reaction kettle, the ratio of cyanoacetamide to solvent is 1: 4(Wt/V), the temperature in the reaction kettle is controlled to be 5-60 ℃, and 824KG of bromine and 50% hydrogen peroxide 374KG are added simultaneously while stirring. After the two materials are dripped, the reaction is continued for 0.2 to 7 hours, the filtered mother liquor is reused, the product obtained by filtering is DBNPA, and the yield is 105.2 percent. In this example 4, the molar ratio of cyanoacetamide to bromine to hydrogen peroxide is:
420/84∶824/160∶(1/2×374/34)＝1∶1.03∶1.1
the mother liquor used in the embodiment of the present invention refers to: and directly adding the mother liquor generated in the reaction into a reaction container as a solvent. Since the water loss inevitably occurs in the industrial process, the extracted product may take a small amount of water, and the water may be periodically supplied to the reaction vessel. Generally, a liquid level reference line is set in the reaction vessel, and water is added until the reaction solution reaches the liquid level reference line.
The industrial preparation method of the 2, 2-dibromo-2-nitrilopropionamide provided by the invention is described in detail, the principle and the implementation mode of the invention are explained by applying specific examples, and the description of the examples is only used for helping to understand the method and the core idea of the invention; meanwhile, for a person skilled in the art, according to the idea of the present invention, there may be variations in the specific embodiments and the application scope, and in summary, the content of the present specification should not be construed as a limitation to the present invention.
Claims (6)
1. An industrial preparation method of 2, 2-dibromo-2-nitrilopropionamide, which is characterized by comprising the following steps:
adding cyanoacetamide and a solvent into a reaction vessel, and simultaneously dropwise adding bromine and hydrogen peroxide while stirring;
after the bromine and the hydrogen peroxide are added, continuously reacting for a period of time, and filtering to obtain 2, 2-dibromo-2-nitrilopropionamide;
wherein the molar ratio of the cyanoacetamide to the bromine to the hydrogen peroxide is 1: 1.01-1.08: 1.0-1.2.
2. The method of claim 1,
under the condition that the reaction temperature is 5-60 ℃, bromine and hydrogen peroxide are simultaneously dripped.
3. The method of claim 1 or 2,
the concentration of the dropwise added hydrogen peroxide is 40-50%.
4. The method of claim 1,
the solvent is selected from: water or mother liquor generated by the reaction.
5. The method of claim 1 or 4,
the dosage relation of the cyanoacetamide and the solvent is as follows: 1Kg of cyanoacetamide to 3-6L of solvent.
6. The method of claim 1,
after the bromine and the hydrogen peroxide are added, the reaction is continued for 0.2 to 8 hours.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4925967A (en) * | 1987-09-15 | 1990-05-15 | Bromine Compounds Limited | Process for the preparation of 2,2-dibromonitrilopropionamide |
| CN101781233A (en) * | 2010-03-18 | 2010-07-21 | 西安近代化学研究所 | Synthesis method of 2,2-dibromo-2-malonamidenitrile |
-
2011
- 2011-03-07 CN CN2011100539225A patent/CN102161630A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4925967A (en) * | 1987-09-15 | 1990-05-15 | Bromine Compounds Limited | Process for the preparation of 2,2-dibromonitrilopropionamide |
| CN101781233A (en) * | 2010-03-18 | 2010-07-21 | 西安近代化学研究所 | Synthesis method of 2,2-dibromo-2-malonamidenitrile |
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Application publication date: 20110824 |