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DBNPA or 2,2-dibromo-3-nitrilopropionamide is a quick-kill biocide that easily hydrolyzes under both acidic and alkaline conditions.
DBNPA is preferred for its instability in water as it quickly kills and then quickly degrades to form a number of products, depending on the conditions, including ammonia, bromide ions, dibromoacetonitrile, and dibromoacetic acid.DBNPA acts similar to the typical halogen biocides.
CAS Number: 10222-01-2
EC Number: 233-539-7
IUPAC Name: 2,2-Dibromo-2-cyanoacetamide[1]
Chemical Formula: C3H2Br2N2O
Other names: 2,2-DIBROMO-2-CYANOACETAMIDE, 10222-01-2, Dibromocyanoacetamide, Dbnpa, 2,2-Dibromo-3-nitrilopropionamide, Acetamide, 2,2-dibromo-2-cyano-, 2-Cyano-2,2-dibromoacetamide, XD-7287l Antimicrobial, Caswell No. 287AA, Dibromonitrilopropionamide, 2,2-Dibromo-2-carbamoylacetonitrile, Dowicil QK 20, Dibromocyano acetic acid amide, NSC 98283, XD-1603, HSDB 6982, UNII-7N51QGL6MJ, XD 7287L, EINECS 233-539-7, EPA Pesticide Chemical Code 101801, BRN 1761192, DTXSID5032361, 2,2-Dibromo-3-nitrilopropanamide, Acetamide, 2-cyano-2,2-dibromo-, NSC-98283, 7N51QGL6MJ, DTXCID3012361, DOW ANTIMICROBIAL 7287, 3-02-00-01641 (Beilstein Handbook Reference), DIBROMO-3-NITRILOPROPIONAMIDE, 2,2-, 2,2-DIBROMO-3-NITRILOPROPIONAMIDE [HSDB], C3H2Br2N2O, 2,2-dibromo-2-cyano-acetamide, Cyanodibromoacetamide, MFCD00129791, DPNPA, XD7287l Antimicrobial, 2,2Dibromo2cyanoacetamide, NCIOpen2_006184, SCHEMBL23129, Acetamide, 2,2dibromo2cyano, Acetamide, 2cyano2,2dibromo, Acetamide,2-dibromo-2-cyano-, 2,2Dibromo2carbamoylacetonitrile, 2-Cyano-2,2-dibromo-Acetamide, CHEMBL1878278, DIBROMOCYANOACETAMIDE [INCI], NSC98283, Tox21_300089, XD1603, 2,2-Dibromo-2-cyanoacetamide, 9CI, 2, 2-Dibromo-2-carbamoylacetonitrile, 2,2-Dibromo-2-cyanoacetamide, 96%, AKOS015833850, 2,2-bis(bromanyl)-2-cyano-ethanamide, USEPA/OPP Pesticide Code: 101801, alpha, alpha-Dibromo-alpha-cyanoacetamide, NCGC00164203-01, NCGC00164203-02, NCGC00253921-01, AS-12928, CAS-10222-01-2, DB-027512, CS-0144768, D2902, NS00009357, H11778, A800546, Q-102771, Q5204411, dbnpa; 2,2-dibromo-2-cyanoacetamide; 2,2-dibromo-2-carbamoylacetonitrile; 2,2-dibromo-3-nitrilopropionamide; dbnpa
DBNPA has the following characteristics:
Compatible with the membrane
Fast-acting
Cost-effective
Acceptable transportation, storage, stability and handling characteristics
Broad-spectrum control (e.g., planktonic and sessile organisms); algae control is seasonal and situational
Biodegradable
DBNPA is used in a wide variety of applications. Some examples are papermaking as a preservative in paper coating and slurries. It is also used as slime control on paper machines, and as a biocide in hydraulic fracturing wells and in cooling water.
DBNPA can be synthesized reacting sodium bromide and cyanoacetamide. Its crystals are monoclinic and belong to the space group P21/n.
High-performance liquid chromatography analyses of ppm concentrations of DBNPA and its degradation products in laboratory tests of several natural water samples were used to follow the reactions involved. A hydrolysis pathway leads to dibromoacetonitrile (DBAN) and other products. The presence of organic material in the water leads to degradation by a second pathway in which monobromonitrilopropionamide (MBNPA) and several other degradation products are formed.
The model describes quantitative relationships of DBNPA dosage and the natural water's organic material content, as measured by total organic carbon (TOC), in the degradation pathways of DBNPA. The model helps interpret the aquatic toxicity of the rapidly changing complex mixture produced during these degradations. Simulations of the DBNPA treatment of cooling towers were compared to limited experimental data which indicated that most of the degradation occurred by the pathway which produced the less toxic products
DBNPA is an off-white crystalline solid with a mild medicinal antiseptic odor. It is slightly volatile, very soluble in water, and corrosive.
DBNPA is used to control bacteria, fungi and slime-forming algae in cooling water systems, evaporative condensers and heat exchangers, air washing systems, pulp mill and paper manufacturing, and oil extraction drilling fluids. It also is used as a preservative in paints, industrial coatings and adhesives, metalworking cutting fluids, and paper and paper products.
The melting point of 125 C. Purity was checked by elemental analysis, infrared analysis [IR (Nujol mull), 1,710 cm (C=O) l, and by nuclear magnetic resonance spectroscopy [NMR (dimethyl sulfoxide ), 8.36 6 (doublet) J.
Physical properties and Chemical properties.
The white, crystalline DBNPA has been stable for at least four years under laboratory storage conditions. This conclusion is based upon no detectable change in appearance or biological activity during this storage period. DBNPA dissolves in water to give a relatively stable solution in an acid pH range. Its unusual solubility and stability in polyethylene glycol (average molecular weight, 200) make this glycol a preferred solvent. Aqueous solutions hydrolyze under alkaline conditions, with the rate of decomposition increases with the alkalinity.
However, the rate of hydrolysis is not fast enough to interfere with the antimicrobial activity of fresh, alkaline (pH 7 to 9.5) solutions. Heat and ultraviolet and fluorescent light also cause aqueous solutions of DBNPA to degrade, as evidenced by the change of the antimicrobial endpoint as a given solution age. This ecomposition has also been substantiated by chemical analysis.
It is understood in the membrane industry that thin-film composite polyamide membranes have limited resistance to chlorine-based oxidants.
Therefore, operators have relatively few options regarding chemicals that can be safely used to disinfect RO/NF systems and prevent bio growth/biofouling. One option is the chemical, DBNPA, which is a fast-acting, non-oxidizing biocide which is very effective at low concentrations in controlling the growth of aerobic bacteria, anaerobic bacteria, fungi and algae.
DBNPA is an advantageous disinfectant since it also quickly degrades carbon dioxide, ammonia and bromide ion when in an aqueous environment. This allows the effluent to be safely discharged even in sensitive water bodies. It is degraded by reactions with water, nucleophiles, and UV light (rate is dependent on pH and temperature). The approximate half-life is 24 hr @ pH 7,2 hr @ pH 8, 15 min @ pH 9. The vast majority of microorganisms that come into contact with it are killed within 5 to 10 minutes.
DBNPA is deactivated by reducing agents, so a higher concentration of DBNPA will be required if residual reducing agents are present in the feed water. For example, Sodium Bisulfite (SBS) will deactivate DBNPA. If SBS is dosed during service or flushing operations, additional DBNPA will be required at a suggested dose rate of 1.0 to 1.3 ppm DBNPA per 1 ppm of SBS to account for deactivation. Excess SBS can also be used to accelerate the deactivation of DBNPA in discharged waters.
Although DBNPA is non-oxidizing, it will give an ORP reading of about 400 mv when in the range of 0.5 – 3 ppm ( for comparison, 1 ppm chlorine typically gives an ORP reading of about 700 mv). Intermittent dosing can be performed during service operation, during a low-pressure flush mode, or by a batch CIP (Clean-In-Place) system. RO/NF permeate may need to be diverted to drain as operations dictate, though it is estimated that greater than 98% of the DBNPA is rejected by brackish water membranes and greater than 99.5% by seawater membranes.
For waters containing > 100 CFU/ml (or if you already have biofilm within the RO/NF system), suppliers recommend 30 ppm active ingredient for a full 3 hours. During intermittent dosing, the permeate should be dumped to drain if product water is for potable use. If a biofilm is present, sanitization should be preceded by an alkaline cleaning. For continuous dosing during service operation, between 0.5 to 2 ppm of active ingredient is recommended to maintain a biostatic environment.
RO/NF permeate may need to be diverted to drain as operations dictate. Continuous dosing can be significantly more expensive in terms of operating costs so the site situation will dictate if this is instituted. DBNPA is deactivated by reducing agents, so a higher concentration of DBNPA will be required if residual reducing agents are present in the feed water. For example, Sodium Bisulfite (SBS) will deactivate DBNPA.
If SBS is dosed during service or flushing operations, additional DBNPA will be required at a suggested dose rate of 1.0 to 1.3 ppm DBNPA per 1 ppm of SBS to account for deactivation. Excess SBS can also be used to accelerate the deactivation of DBNPA in discharged waters. Although DBNPA is non-oxidizing, it will give an ORP reading of about 400 mv when in the range of 0.5 – 3 ppm ( for comparison, 1 ppm chlorine typically gives an ORP reading of about 700 mv).
For CIP use, 30 - 50 ppm of active ingredient for 1 hour would be recommended. For heavy biofilms, it should be followed by an alkaline cleaning. Test kits are available from the chemical suppliers to verify that DBNPA is at the desired concentration or has been completely rinsed from the system. According to its chemical properties, DBNPA can be degraded via two pathways; hydrolysis and nucleophilic reaction.
For PT 4 nucleophilic reaction is the relevant pathway after DBNPA comes into contact with sulphur containing reducing species (“nucleophiles”), light or organic material (e.g., proteins, bacteria, humus/fulvic acids, etc.). DBNPA will quickly be degraded to cyanoacetamide (CAM). DBNPA is not readily biodegradable. Based on a weight of evidence approach including several studies from the open literature a degradation half-life in soil (DT50) of 20.9 hours at 12oC was used for the risk assessment. In addition, the default value of inherent biodegradable substances was included.
DBNPA has a very low vapor pressure, a low Henry’s law constant and is additionally not used in a manner, which leads to direct release to the atmosphere.
The mixing and loading process takes place in completely closed systems. Thus, the environmental exposure during mixing and loading is considered to be negligible compared to the actual application of DBNPA. The emission estimations for the use of DBNPA in PT4 have been determined using two different scenarios (a tonnage-based scenario and a consumption-based scenario) and a tiered approach.
For CAM only the consumption-based scenario, representing the realistic worst case scenario is evaluated
The standard method to apply DBNPA is intermittent dosing. The amount of DBNPA used depends on the severity of the biological fouling. With a waterless prone to biological fouling, using 10 – 30 mg/L of the active ingredient for 30 minutes to 3 hours every 5 days can be effective.
Because DBNPA is deactivated by reducing agents (such as sodium bisulfite used for chlorine removal), a higher concentration of DBNPA will be required if there is residual reducing agent in the feedwater. The concentration of DBNPA should be increased by 1 ppm of active ingredient for every ppm of residual reducing agent in the RO feedwater.
To remove the dead biofilm, an alkaline cleaning is also recommended . Biocides, their degradation products, and other ingredients in their formulations are not always completely rejected by RO membranes. For this reason, during intermittent dosing, it may be necessary to discharge the permeate during biocide injection because the permeate may contain slightly elevated levels of organics. Note that although DBNPA is nonoxidizing, it does give an ORP response in approximately the 400 mV range at concentrations between 0.5 and 3 mg/L. For comparison, chlorine and bromine give a response in the 700 mV range at 1 mg/L, which increases with
DBNPA is a broad-spectrum and efficient industrial fungicide. DBNPA is used to prevent bacteria and algae from growing in papermaking, industrial circulating cooling water, mechanical lubricants, pulp, wood, paint, and plywood. 2-2-Dibromo-3-Nitrilopropionamide (DBNPA) is currently popular at home and abroad. Organic bromine fungicides.
Sterilization mechanism of DBNPA. DBNPA molecules can rapidly penetrate microbial cell membranes. Act on certain protein groups.
Intended use, target species and effectiveness
DBNPA is intended for use in food processing vessels (e.g. industrial mayonnaise or yogurt producing facilities, fermenters for beer or other fermented products), which are periodically disinfected after use. The disinfection and processing exclusively take place in the industry and only industrial workers may come into contact with DBNPA. DBNPA is a fast-acting biocide and is exerting its biocidal action directly after its application.
DBNPA may be used to control bacteria and reduce biofouling in various membrane system types (reverse osmosis, ultra-filtration, nano-filtration, and microfiltration) used for industrial water processing. Acceptable industrial applications include reverse osmosis systems for the production of boiler make-up water for electric power production, electronic component rinsing, and in the chemical manufacturing industry. DBNPA can also be used for off-line cleaning of RO membranes producing potable and municipal water.
DBNPA has proven efficacy at low concentrations against bacteria, fungi, yeast, cyanobacteria (also referred to as blue-green algae) and true algae. The DBNPA molecule will function immediately upon introduction into the feed water and antimicrobial control is rapidly achieved if properly dosed.
DBNPA offers an advantageous combination of quick kill properties followed by fast chemical degradation, including hydrolysis. The dominant degradation pathway at use conditions involves reactions with nucleophilic substances or organic material invariably
found in water. Nucleophilic degradation forms cyanoacetamide. When the disposal of concentrate involves the release to large open waterways, additional degradation will occur via exposure to UV radiation.
When sufficiently diluted, DBNPA and its degradation products become biodegradable. The ultimate degradation products formed from both chemical and biodegradation processes of DBNPA include ammonia, carbon dioxide, and bromide ions.
Therefore, meeting the local environmental regulations for the permitted discharge of the reject stream should not be affected by DBNPA use.
DBNPA product performance
Broad-spectrum, fast and efficient sterilization performance
DBNPA has a broad spectrum of bactericidal properties. It has a good killing effect on bacteria, fungi, yeast, algae, biological slime and pathogenic microorganisms that threaten human health.
Dibromo 3 Nitrilopropionamide (DBNPA) is characterized by extremely fast sterilization and high efficiency. The sterilization rate can reach over 99% in 5-10 minutes. DBNPA was compared to the other three biocides.
The results showed that when the same bactericidal effect was achieved, DBNPA was used at a dose of only 7.5ppm, which is much lower than the other three fungicides.
Good inhibition of peeling on biofilms. When DBNPA is added to the system, its active components act rapidly on planktonic microorganisms. It can be quickly sterilized. At the same time, the permeability of organic bromine is good. The active component of the agent rapidly penetrates the metal surface. Acts on smaller microbial communities. It allows rapid depolymerization and prevents the formation of biofilms.
For systems that have formed biofilms, the active components do not react with the slime layers in the biofilm. It quickly penetrates deeper into the biofilm. A microbial community acting at the junction of a biofilm and a metal surface. Destruction of its viscosity causes the biofilm to fall off.
Experimental studies have shown that for the peeling of the biofilm at the age of 7 days, the smaller dosage can achieve the same peeling effect, and the advantage of the peeling effect on the biofilm is very obvious.
Effectively kill Legionella
DBNPA on Legionella is very significant. Studies have shown that 2-5mg/L DBNPA (effective), can reduce Legionella 5-6 logs within 3 hours. 2-4 mg/L DBNPA (effective) can reduce Legionella by 6 logs for 2 hours. For Legionella in biofilms. 10mg/L DBNPA (effective), 12 hours can completely kill Legionella. Additional data indicate that low doses of organic bromine and glutaraldehyde are used in combination. Legionella in biofilms can be lowered to undetectable levels.
Rapid degradation
DBNPA is rapidly degraded to carbon dioxide, ammonia and bromine salts upon completion of bactericidal action. It does not cause the enrichment of harmful ions in the water. There is no impact on the environment, so emissions are not restricted. This is a distinguishing feature of organic bromine biocides that distinguishes them from other non-oxidizing biocides.
Effectively kill sulfate-reducing bacteria
The oilfield sewage has a high sulfate content, which is very beneficial to the reproduction of sulfate-reducing bacteria. The large-scale reproduction of sulfate-reducing bacteria will lead to an increase in the content of H2S in water. 2 2 Dibromo 3 Nitrilopropionamide (DBNPA) acts rapidly on sulfate-reducing bacteria. It can be quickly killed before it reacts with sulfate to form H2S.
Experimental studies have shown that 10 mg/L can effectively control the sulfate-reducing bacteria in the system, so as to completely remove the sulfide in the re-injection system and protect the system from sulfide corrosion.
DBNPA application area
DBNPA is widely used as a disinfectant, bactericide, algicide, slime stripper, and mildew inhibitor in the following aspects.
The circulating cooling water system, oil field water injection system, bactericide, algicide, slime stripper in the paper industry.
Preservatives for paints, waxes, inks, detergents, surfactants, slurries, resins.
Process water, air purifier system in the machinery manufacturing industry, fungicides, and algicides in municipal water landscapes.
DBNPA usage
When used as a water treatment slime stripper, the DBNPA is added at a concentration of 30-50 mg/L.
Used as a water treatment bactericide for circulating cooling water systems. According to water retention, DBNPA is added at 10-20 mg/L.
DBNPA is also used in the process of papermaking to prevent reducing the quality of paper by a generation of microorganisms.
It is suitable for metal cutting of cooling liquor, recovery system of oil, latex, and ply-woods as anti-spy biocides. DBNPA has the following advantages.
Easy to handle.
No unusual oxidation hazards.
Similar performance and safety in paper and oilfield applications.
Slime control in the wet-end of the paper mill and performs exceptionally well against slime-forming bacteria.
DBNPA has exhibited outstanding efficiency in bio-films and against a broad spectrum of bacteria, fungus, and yeasts.
Additionally, DBNPA series products are used in the short-term preservation of coatings and coating additives. Such as latex, starch and mineral slurries. It is a quick-kill biocide that is broad-spectrum and does not contain or release formaldehyde.
DBNPA is used as a non-oxidizing bactericide. In combination with bromine-based bactericides under frequent leakage conditions, the microbial control of the system can be improved. The specific plan is as follows.
Microbial control effect:
Under the harsh water quality conditions of the refinery system, DBNPA works synergistically with the bromine-based bactericide to better control the microorganisms. It has a good peeling performance in a system where biological slime breeds severely. After the system uses DBNPA biocide, the cooling tower packing and tower wall are clean, and no sticky mud algae breeds. DBNPA contributes to the maintenance of residual chlorine in bromine-based bactericides.
DBNPA is a broad-spectrum and high-efficiency industrial fungicide used to prevent the growth of bacteria and algae in papermaking, industrial circulating cooling water, metalworking lubricants, pulp, wood, paint and plywood.
DBNPA can quickly penetrate the cell membrane of microorganisms and act on a certain protein group to stop the normal redox of cells and cause cell death.
DBNPA's branches can also selectively bromine or oxidize specific enzyme metabolites of microorganisms, ultimately leading to microbial death.
DBNPA has good peeling performance, no foam, and its liquid products and water can be dissolved at any ratio.
The biocide 2,2-dibromo-3-nitrilopropionamide (DBNPA) is the second most commonly used biocide in UOG after glutaraldehyde. DBNPA is a fast-acting electrophilic biocide; it is quick and effective in contact, but the protection is not long-lasting. This biocide inhibits essential biological functions by reacting with nucleophiles (particularly sulfur-containing nucleophiles) inside the cell. DBNPA, and some of its degradation products, can also be harmful to humans and animals. These associated compounds have been demonstrated to be moderate to highly toxic by ingestion and inhalation, can be corrosive to eyes, and have been shown in terrestrial and aquatic animal studies to cause developmental issues.
DBNPA is not toxic to all life, however, as it is biodegradable under both aerobic and anaerobic conditions, with a reported biotic half-life of less than 4 h under both conditions at neutral pH. However, the hydrolysis and aquatic photolysis half-life of this compound are pH-dependent, with faster degradation occurring at a more alkaline pH. For example, the abiotic half-lives of DBNPA at pH 5, 7, and 9 are 67 days, 63 h, and 73 min, respectively. Conversely, low pH has been characteristic of HF-impacted streams, which thus provide favorable conditions for the stability of DBNPA and its degradation products.
DBNPA is a non-oxidative agent, rapidly degrading in alkaline aqueous solutions. The organic water content, as well as light, enhances the hydrolysis and debromination of DBNPA into cyanoacetamide followed by degradation into cyanoacetic acid and malonic acid, which are non-toxic compounds. This degradation pathway makes the use of DBNPA relatively environmentally friendly. DBNPA is compatible with polyamide-based membranes and shows high rejection rates for RO membranes. The antimicrobial effect is due to the fast reaction between DBNPA and sulfur-containing organic molecules in microorganisms such as glutathione or cysteine.
The properties of microbial cell-surface components are irreversibly altered, interrupting the transport of compounds across the membrane of the bacterial cell and inhibiting key biological processes of the bacteria.
Broad Spectrum Non-Oxidising Biocide:
Active Ingredients: min 98% 2,2-Dibromo-3-NitriloPropionamide (DBNPA) assay Highly effective against a wide range of common water-borne organisms with proven efficacy against Legionella. Accepta 6404 will control these organisms and help to control microbiological fouling.
Compatibility with other water treatment chemicals and water conditions: DBNPA is compatible with other treatment chemicals with the exception of mercaptobenzothiazole. It also is not compatible with ammonia or hydrogen sulfide-containing water. DBNPA maintains reliable control in systems running at acidic, neutral, or alkaline pH.
Degradation in water: DBNPA degrades quickly in aqueous environments. At neutral pH, its half-life is about nine hours.
Continuous biocide release by the tablet maintains concentrations effective for control in the tower, while the biocide in the blowdown discharge degrades quickly. So it’s easy to meet strict environmental regulations on tower discharge.
Is DBNPA an oxidizer?
DBNPA is not an oxidizing biocide and it is not a bromine release biocide. DBNPA does act similar to the typical halogen biocides.
DBNPA is a biocide used in a variety of industrial processes to control algae, bacteria, fungi and yeasts. Formulations include tablets and both solid and liquid soluble concentrates. DBNPA is applied through intermittent, initial, intermittent, maintenance, during manufacture and continuous feed treatments, using metering pumps, drip-feed devices and other types of industrial equipment. A National Pollutant Discharge Elimination System (NPDES) permit is required for discharges to waterways.
DBNPA is a highly effective, environmentally friendly biocide. It provides a quick kill while also quickly degrading in water. The final end product is carbon dioxide and ammonium bromide.
Compatibility with other water treatment chemicals and water conditions: DBNPA is compatible with other treatment chemicals with the exception of mercaptobenzothiazole. It also is not compatible with ammonia or hydrogen sulfide-containing water. DBNPA maintains reliable control in systems running at acidic, neutral, or alkaline pH.
