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4,5-Dichloro-2-Octyl-Isothiazolone(DCOIT) is an organic compound, with the Molecular formula C11H17Cl2NOS, CAS 64359-81-5. Generally colorless or light yellow liquid, there are also solid forms present. It has a special pungent odor that some people may feel uncomfortable. It has good solubility in many organic solvents, such as ethanol, toluene, di N-Methylformamide, etc.
It is also soluble in water, but its solubility is low. Relatively stable under dry conditions, but decomposition may occur under light, humidity, and high temperature environments. Therefore, attention should be paid to avoiding exposure to strong light, high temperature, and humidity during use and storage. Commonly used as a fungicide and preservative. It has a broad spectrum of bactericidal activity and has important applications in wood preservation, coatings and adhesives, network films, paper and textiles, industrial water treatment, paints and coatings, etc.
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Chemical Formula |
C11H17Cl2NOS |
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Exact Mass |
282 |
|
Molecular Weight |
281 |
|
m/z |
m/z: 281 (100.0%), 283 (63.9%), 282 (11.9%), 285 (10.2%), 284 (7.6%), 283 (4.5%), 285 (2.9%), 286 (1.2%) |
|
Elemental Analysis |
C, 46.81; H, 6.07; Cl, 25.12; N, 4.96; O, 5.67; S, 11.36 |
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Morphological |
powder |
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Color |
powder |
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Melting point |
40.0 to 44.0 ° C |
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Boiling point |
322.6 ± 52.0 ° C (predicted) |
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Density |
1.25 ± 0.1 g / cm3 (predicted) |
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Storage conditions |
insert atmosphere, 2-8 ° C |
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solubility alcohol |
solublesoluble 40 parts of solvent |
|
Acidity coefficient ( pKa ) |
- 6.09 ± 0.60 (predicted) |
4,5-Dichloro-2-Octyl-Isothiazolone (DCOIT), with the chemical formula C11H17Cl2NOS and CAS number 64359-81-5, is a low toxicity, high efficiency, and broad-spectrum organic compound that has demonstrated excellent application value in multiple industrial fields.
Marine pollution prevention field
The application of DCOIT in marine anti fouling is particularly prominent, as it is an environmentally friendly product that replaces traditional organotin anti fouling agents (such as TBTO). Its core uses include:
Ship anti-fouling paints
DCOIT is added as an active ingredient to ship anti fouling paint, continuously releasing effective ingredients through slow-release technology to form a long-lasting protective layer. Experiments have shown that adding 5% -10% DCOIT to marine paint can significantly inhibit the adhesion of marine organisms such as barnacles, algae, and bacteria on the surface of the ship, with a protection period of over five years. Its anti fouling effect is superior to traditional organotin compounds, and it does not cause cumulative toxicity to marine organisms.
Corrosion prevention of marine facilities
DCOIT can effectively prevent microbial corrosion (MIC) in anti-corrosion coatings for offshore platforms, docks, and other facilities. It prolongs the service life of metal structures by disrupting the structure of microbial cell membranes, inhibiting biofilm formation. For example, in anti-corrosion coatings containing DCOIT, the corrosion rate of steel structures can be reduced by more than 60%.
Environmental friendliness advantage
DCOIT can quickly decompose into non-toxic substances in the environment and will not accumulate in marine organisms. The toxicity of its metabolites is only 1/100000 of the original compound, significantly lower than the toxicity of TBTO degradation products. This characteristic makes it an environmentally friendly anti fouling agent recommended by the International Maritime Organization (IMO).
Industrial anti-corrosion field
DCOIT performs excellently in industrial anti-corrosion and is suitable for various substrates and process scenarios:
Coatings and paints
Dry film anti mold: Adding 0.1% -0.5% DCOIT to building coatings and industrial paints can effectively inhibit the growth of mold such as Aspergillus niger and Penicillium, extending the service life of coatings by 3-5 years.
Wet film protection: During the coating production process, DCOIT can prevent microbial contamination of raw materials and semi-finished products, ensuring product quality stability.
Plastic and rubber
Antibacterial modification: DCOIT can be added to plastics such as polyethylene (PE) and polyvinyl chloride (PVC) to prepare antibacterial pipes, films, and other products. For example, EVA foam material containing 1.5% DCOIT has an antibacterial rate of 99.92% against Escherichia coli.
Rubber protection: In rubber products such as tires and seals, DCOIT can prevent microbial degradation of rubber molecular chains and improve product durability.
Adhesives and sealants
DCOIT can inhibit microbial contamination of adhesives during storage and use, preventing viscosity loss or curing failure. Adding 0.2% DCOIT to polyurethane adhesive can extend the shelf life of the product to 18 months.
Leather mold prevention: Adding DCOIT during the leather tanning process can prevent the finished leather from mold growth in humid environments, maintaining surface gloss and physical properties.
Textile additives: As a textile finishing agent, DCOIT can endow fabrics with antibacterial properties and is suitable for fields such as sportswear and medical textiles.
Water treatment field
4,5-Dichloro-2-Octyl-Isothiazolone plays a crucial role in water treatment, especially suitable for circulating cooling water systems:
Microbial control:
Adding 0.25-6mg/L DCOIT to circulating water can effectively inhibit the growth of algae, bacteria, and fungi. For systems with severe algae pollution, adding 2mg/L DCOIT twice a week can achieve an algae killing rate of over 90%.
Synergistic effect:
DCOIT can be used in combination with fungicides such as dodecyl dimethyl benzyl ammonium chloride (Jier Mie) and glutaraldehyde to synergistically enhance efficacy through different mechanisms of action, reducing the dosage and cost of a single agent.
Environmental advantages:
Compared to traditional oxidative disinfectants such as chlorine, DCOIT is not affected by water hardness and does not produce carcinogenic byproducts such as trihalomethanes (THMs), which is in line with the trend of green water treatment.
Building materials and decoration field
DCOIT provides long-lasting anti mold protection for building materials, enhancing product added value:
Decorative wood:
Adding DCOIT to wood anti-corrosion treatment can prevent mold and termite erosion and extend the service life of outdoor wood. For example, wood paint containing 1% DCOIT can keep wood mold free for 10 years in humid environments.
Sealing and sealing agents:
DCOIT can inhibit microbial contamination of sealants after construction, preventing cracking or detachment. Adding 0.5% DCOIT to silicone sealant can achieve a mold resistance level of 0 (the highest level) for the product.
Other special applications
Paper industry
DCOIT can prevent paper from getting moldy during storage, especially suitable for products with high hygiene requirements such as packaging paper and toilet paper. Adding 0.1% DCOIT to pulp can extend the anti mold cycle of paper to 6 months.
Food and cosmetics (restricted use)
Although DCOIT has low toxicity characteristics, its use must strictly comply with regulations. In food packaging materials, DCOIT is only allowed to be used in indirect contact scenarios (such as cardboard box inner wall coatings), and the residual amount must be less than 10mg/kg. In cosmetics, DCOIT is limited to rinse off products (such as shampoo), with a maximum allowable concentration of 0.0015%.
Application Cases
Ship anti fouling: After an international shipping company adopted anti fouling paint containing 8% DCOIT, the cleaning cycle of the ship's hull was extended from every 6 months to every 18 months, and fuel consumption was reduced by 12%.
Plastic antibacterial: A certain household appliance company added DCOIT to the refrigerator liner material, achieving a 99% antibacterial rate and a 70% decrease in market complaints.
Water treatment: After switching to DCOIT for the circulating water system in a chemical industrial park, microbial contamination incidents were reduced by 90%, and annual maintenance costs were reduced by 500000 yuan.
This is our advanced product 4,5-Dichloro-2-Octyl-Isothiazolone.
Remark: BLOOM TECH(Since 2008), ACHIEVE CHEM-TECH is the subsidiary of us.
Based on the rationality of the process, 4,5-dichloro-2-n-octyl-3-isothiazolinone was prepared by cyclization reaction with n-octylamine, dimethyl Dithiocarboxylate and phosphorus oxychloride as the main raw materials.
A commonly used method for synthesizing DCOIT is to prepare 4,5-Dichloro-2-octyl-isothiazoline through the chlorination reaction of 5-chloroisothiazolin-3-one. The following is a possible synthesis route:
Starting from 5-chloroisothiazolin-3-one, octyl groups can be introduced by reacting with chlorinated reagents of chloroalkanes (such as 1-bromooctane) under alkaline conditions. The reaction is usually carried out in an organic solvent, such as dichloromethane or chloroform. The reaction temperature and time may vary, and the specific conditions can be optimized through trial and error methods.
After the reaction is completed, neutralize the alkaline substances in the reaction solution by adding hydrolysis agents (such as water or alcohol), and extract the reaction mixture into an organic solvent.
The extracted organic phase can be purified by vacuum distillation or extraction to remove inorganic salts and unreacted raw materials.
Finally, the purified product is further refined through methods such as crystallization and recrystallization.
It should be noted that the above synthesis routes are for reference only, and the specific synthesis conditions, reaction parameters, and purification methods may vary depending on actual operational requirements. Therefore, in practical operation, it is recommended to use professional chemical laboratories and equipment, and refer to relevant literature and patent materials to obtain more accurate and detailed synthesis methods.
The following is a chronological summary of the development history of 4,5-dichloro-2-octyl-3-isothiazolinone (DCOIT):
Research and development background: With the increasingly serious pollution caused by organotin anti fouling agents to the marine environment, finding an efficient, low toxicity, and environmentally friendly alternative has become an urgent need.
Commercialization process: Rohm&Haas in the United States successfully developed DCOIT and launched it on the market under the trademark Sea Line 211. DCOIT, as an environmentally friendly marine anti fouling agent, has quickly gained recognition from the international community.
Honors and Awards:
In 1996, DCOIT won the Presidential Green Chemistry Challenge Award;
In 1997, won the Chemical Environment Excellence Award. These honors further demonstrate its outstanding contributions in the field of environmental protection.
Application field expansion: DCOIT is not only widely used in ship anti fouling paint, industrial anti-corrosion coatings and other fields, but also gradually expanded to the role of wet film prevention of fungi and bacteria growth in plastic leather, coatings, wood, ink and adhesives.
Market recognition: With the successful application of DCOIT in multiple fields, its market demand is gradually increasing. At the same time, its low toxicity, high efficiency, and broad-spectrum bactericidal performance have also been widely recognized in the market.
Improvement of synthesis method: In response to the problems of high impurities and low yield in early synthesis methods, scientists are constantly exploring new synthesis routes and process conditions. For example, by optimizing the conditions of ester ammonia exchange reaction and closed-loop chlorination reaction, the yield and purity of DCOIT have been improved.
Technological innovation: With the deepening of the concept of green chemistry, scientists have begun to pay attention to the environmental issues in the synthesis process of DCOIT. By developing new catalysts and solvent systems, environmental pollution and energy consumption during the synthesis process have been reduced.
Market Expansion: With the increasing global awareness of environmental protection and the increasingly strict environmental regulations, DCOIT, as a low toxicity, efficient, and environmentally friendly fungicide, continues to increase in market demand. Meanwhile, its application areas are constantly expanding, such as in food, cosmetics, water treatment, and other fields.
Diversified applications: In addition to traditional application areas, DCOIT also demonstrates potential application value in fields such as new energy and environmentally friendly materials. For example, as an antibacterial agent used in the preparation of antibacterial EVA foam materials.
Environmental Impact Study: Although 4,5-dichloro-2-octyl-isothiazolone is considered an environmentally friendly marine anti fouling agent, its widespread use may still cause secondary pollution to the marine environment. Therefore, scientists have begun to pay attention to the degradation behavior and ecological toxicity of DCOIT in the environment.
Health impact research: With the widespread application of DCOIT in multiple fields, its impact on human health has gradually received attention. For example, studies have revealed the binding behavior of DCOIT with human serum albumin, providing scientific evidence for its potential health risks.
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