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Bronopol, also known as bromonitrol, is chemically known as 2-bromo-2-nitro 1,3 propanediol. The most common is bronopol powder, "broopol" is its common name, also known as "pilebo" and "mixed cotton alcohol". It is white to light yellow and yellowish brown crystalline powder at room temperature. It is odorless and tasteless. It is easy to dissolve in water, ethanol and propylene glycol, but difficult to dissolve in chloroform, acetone, benzene, etc. It will decompose slowly in alkaline aqueous solution and corrode some metals, such as aluminum. Bropol is toxic and irritating to eyes, skin and mucous membrane. It can cause congenital abnormalities. It is used in large quantities and is harmful to the environment. It is mainly used as preservative and bactericide in cosmetics, which can effectively control a variety of plant pathogenic bacteria.
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Chemical Formula |
C3H6BrNO4 |
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Exact Mass |
199 |
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Molecular Weight |
200 |
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m/z |
199 (100.0%), 201 (97.3%), 200 (3.2%), 202 (3.2%) |
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Elemental Analysis |
C, 18.02; H, 3.02; Br, 39.95; N, 7.00; O, 32.00 |
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Bromonol (chemical name: 2-bromo-2-nitro 1,3 propanediol, English name Bronopol, CAS number 52-51-7) is a broad-spectrum and highly efficient brominated nitroalcohol compound. With its unique chemical structure and antibacterial properties, it has shown extensive application value in various fields such as agriculture, industry, daily chemical, medicine, and environmental protection.
It is mainly used in agriculture to prevent and control plant bacterial diseases, and its mechanism of action achieves efficient sterilization by disrupting the structure of bacterial cell membranes and inhibiting dehydrogenase activity. Typical applications include:
1. Cotton seed treatment
Soaking seeds at a concentration of 800-1000mg/L can significantly reduce the incidence of black arm disease and bacterial leaf blight caused by cotton corner spot pathogen. Experimental data shows that its efficacy reaches 93.2%, which is significantly superior to traditional drugs such as carbendazim (53.9% efficacy) and amoxicillin (87.3% efficacy). The bromonitrol seed treatment agent developed by Boots, Germany, uses 10kg of pesticide per ton of seeds to achieve full growth period protection.
2. Prevention and control of rice bakanae disease
By oxidizing the thiol groups in bacterial enzymes and inhibiting dehydrogenase activity, the reproduction of pathogenic bacteria can be effectively blocked. In the soaking process, the control effect gradually increased with the prolongation of time after being treated at a concentration of 1000mg/L for 72 hours, and stabilized after 96 hours, with a control effect of over 95%.
3. Broad spectrum protection of crops
It exhibits strong inhibitory effects on Gram negative bacterial diseases such as tomato ulcer disease and cucumber bacterial leaf spot disease. Its low concentration (25ppm) can inhibit the growth of most bacteria and has no phytotoxicity to crops, which meets the needs of green agriculture development.
In industrial recycling water, papermaking, coatings and other scenarios, synergistic efficiency is achieved through compounding technology, becoming the core raw material for industrial anti-corrosion and sterilization:
1. Circulating cooling water system
After compounding with Carcassone and Guanidine compounds, the addition amount can be reduced by 30% -50%, while expanding the antibacterial spectrum to the highly resistant Pseudomonas genus. The application case of a certain petrochemical enterprise shows that the compounding scheme reduces the total bacterial count of the system to below 10CFU/mL and extends the operating cycle by 2 times.
2. Paper pulp anti-corrosion
In response to the corrosive environment caused by the decomposition of sulfides in pulp, the growth of sulfate reducing bacteria is inhibited to reduce equipment corrosion rate. Experiments have shown that a 0.1% concentration treatment can extend the shelf life of pulp from 7 days to 30 days without affecting the physical properties of the paper.
3. Coatings and Adhesives
Adding 0.05% -0.1% bromonitrol to latex paint and water-based adhesives can effectively prevent mold growth during storage.
It is compounded with IPBC (iodopropynyl butyl carbamate) and has an inhibition rate of 99.9% against Aspergillus niger and Aspergillus flavus, meeting the EN71-9 toy safety standard.
3. Metalworking fluid
To address the issue of pH decrease caused by bacterial growth in cutting and quenching fluids, the total bacterial count (<10 ³ CFU/mL) is controlled to maintain the service life of the machining fluid. An application from a certain automotive parts company shows that after using bromonitrol, the cutting fluid replacement cycle has been extended from 2 weeks to 8 weeks, reducing costs by 65%.
In the field of daily chemical industry: the "safety guardian" of cosmetics and detergents
With low irritation and high compatibility, 2-bromo-2-nitro 1,3 propanediol has become the preferred solution for anti-corrosion systems in daily chemical products
1. Cosmetics anti-corrosion
0.01% -0.02% bromine alcohol added in shampoo, face cream and shower gel can inhibit common contaminating bacteria such as Escherichia coli and Staphylococcus aureus. After being compounded with nipagin esters, its inhibition rate against mold increased to 98%, and it has passed the EU CLP regulation EUH208 certification, making it suitable for children's skincare products. A certain international brand of baby shower gel uses a bromonitrol IPBC complex system, which has been confirmed to have no allergenicity through human patch testing.
2. Detergent efficiency enhancement
In laundry detergent and dishwashing detergent, rapid sterilization is achieved by disrupting the permeability of bacterial cell membranes. After treatment with a concentration of 0.05%, the killing rate of Candida albicans reached 99.99%, and the compatibility with surfactants (LAS, AES) was stable without affecting the cleaning power.
3. Fabric processing
Used for post-treatment of functional textiles such as sportswear and underwear, it can endow fabrics with long-lasting antibacterial properties. After 50 washes, the antibacterial rate against Staphylococcus aureus remained above 95%, meeting the GB/T 20944.3-2007 standard.
Medical field: "cross-border application" from external disinfection to oral anti-corrosion
The application in the pharmaceutical field continues to expand, forming a complete solution from skin disinfection to formulation preservation:
1. External fungicide
0.1% -0.5% bromonitrol solution can be used for disinfection of skin wounds and burn wounds, with a sterilization rate twice as fast as iodine and no irritation. Clinical data from a tertiary hospital shows that using it to treat second degree burn wounds reduces the infection rate from 12% to 3%.
2. Oral preservatives
Adding 0.005% -0.01% bromonitrol to oral liquids and syrups can prevent microbial contamination. It achieves long-lasting antibacterial effects by disrupting bacterial RNA synthesis without affecting drug stability.
After using the bromonitrol preservative system, the shelf life of a certain cold syrup was extended from 12 months to 24 months.
3. Specialized drug development
It is compounded with chlorhexidine gluconate to make mastitis topical gel, with MIC (minimum inhibitory concentration) of 0.5 μ g/mL for Staphylococcus aureus and clinical cure rate of 89%. In addition, it can also be used as a preservative for gastritis treatment preparations to ensure the stability of drug efficacy in gastric acid environment.
Environmental protection field: "Green solutions" for deodorization and water treatment
The application in the field of environmental protection reflects its extended value from sterilization to environmental governance:
1. Toilet deodorizer
A deodorizer with 0.05% bromonitrol as the core can simultaneously kill odor producing microorganisms such as Escherichia coli and ammonia bacteria, and decompose odorous gases such as ammonia and hydrogen sulfide. A case study of a public restroom showed that after use, the ammonia concentration decreased from 15ppm to below 2ppm, and the complaint rate of odor decreased by 90%.
2. Garbage disposal deodorization
In the treatment of leachate from landfills, the activity of methane producing bacteria is inhibited to reduce the generation of hydrogen sulfide. Experiments have shown that a 0.1% concentration treatment can reduce the COD (chemical oxygen demand) of leachate by 35%, while eliminating over 90% of odorous gases.
3. Oilfield reinjection water treatment
In response to the corrosion problem caused by sulfate reducing bacteria (SRB) in oilfield reinjection water, a protective film was formed to block bacterial metabolism, reducing the corrosion rate from 0.5mm/a to 0.02mm/a. A certain oilfield application shows that after use, the service life of water injection equipment is extended by three times.
Bropol can be obtained from nitromethane and formaldehyde by alkoxylation and bromination under alkaline conditions. The reaction equation is as follows:
CH3NO2 + 2HCHO →HOCH2C(NO2)HCH2OH
HOCH2C(NO2)HCH2OH +NaOH→[HOCH2C(=NO2)CH2OH]Na+H2O
[HOCH2C(=NO2)CH2OH]Na + Br2→HOCH2C(Br)(NO2)CH2OH+NaBr
There are two operation processes:
(1) Nitromethane, 30% formaldehyde, calcium chloride and sodium hydroxide are added to the reaction device at a molar ratio of 1:2:2:2, stirred, and the solution of bromine and dichloroethane is added dropwise below 0 ℃. After adding in 1H, the amount of bromine was equal to that of nitromethane. The dichloroethane layer is separated and the dichloroethane is evaporated. To obtain a white solid (crude product). The aqueous layer of the reactant was extracted with ether, and the ether in the ether extract was evaporated to obtain a part of the crude product. The crude products were combined and recrystallized with ether to obtain a pure product.
(2) Firstly, 2-nitro-1,3-propanediol is prepared. The molar ratio of nitromethane and 30% formaldehyde solution is 1:2. Then, 2% potassium carbonate is added to the reflux reaction device, heated and refluxed for 1h, cooled and crystallized. 2-nitro-1,3-propanediol was obtained by extracting with ether, drying and evaporating the ether. Then dissolve it in methanol, add 20% sodium methoxide D in methanol, and stir at 20 ° C to precipitate 2-nitro-1,3-propanediol sodium. The sodium salt was filtered out and suspended in dry ether for bromination: bromine was added dropwise to the ether suspension of sodium 2-bromo-2-nitro 1,3 propanediol under 0 ℃, and then stirred for 10min. Filter and evaporate the ether to obtain bropol.
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