3-diol (Bronopol)
2-Bromo-2-nitro-1,3-propanediol
CAS: 52-51-7
Molecular Formula: C3H6BrNO4
3-diol (Bronopol) - Names and Identifiers
3-diol (Bronopol) - Physico-chemical Properties
| Molecular Formula | C3H6BrNO4 |
| Molar Mass | 199.99 |
| Density | 2.0002 (rough estimate) |
| Melting Point | 130-133°C(lit.) |
| Boling Point | 358.0±42.0 °C(Predicted) |
| Flash Point | 167°C |
| Water Solubility | 25 g/100 mL (22 ºC) |
| Solubility | Soluble in alcohol and ethyl acetate-slightly soluble in chloroform, acetone, ether and benzene |
| Vapor Presure | 1.45E-06mmHg at 25°C |
| Appearance | White to light brown yellow solid or powder |
| Color | White to yellow |
| Merck | 14,1447 |
| BRN | 1705868 |
| pKa | 12.02±0.10(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Stability | Stable. Hygroscopic. Incompatible with strong oxidizing agents, strong bases, strong reducing agents, acid chlorides and anhydrides, moisture. |
| Refractive Index | 1.6200 (estimate) |
| MDL | MFCD00007390 |
| Physical and Chemical Properties | melting point 124-129°C water-soluble 25g/100 mL (22°C) |
| Use | Widely used in water treatment, medicine, pesticides, cosmetics, detergents and other industries as preservatives and sterilants |
3-diol (Bronopol) - Risk and Safety
| Risk Codes | R21/22 - Harmful in contact with skin and if swallowed. R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R50 - Very Toxic to aquatic organisms |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | UN 3241 4.1/PG 3 |
| WGK Germany | 2 |
| RTECS | TY3385000 |
| FLUKA BRAND F CODES | 4.2-8-9-21 |
| TSCA | Yes |
| HS Code | 29055999 |
| Hazard Class | 4.1 |
| Packing Group | III |
| Toxicity | LD50 in mice, rats (mg/kg): 350, 400 orally (Croshaw) |
3-diol (Bronopol) - Upstream Downstream Industry
3-diol (Bronopol) - Reference Information
| Overview | ropol, chemical name 2-bromo-2-nitro-1, 3-propanediol, other names include bromnitol, bacteriostatic alcohol, etc. Foreign trade name: Bronopol. White crystalline powder, Melting Point: 122~130 ℃, easily soluble in water, ethanol, propylene glycol, ethyl acetate, etc., slightly soluble in oil, difficult to dissolve in chloroform, acetone, etc. In 1919, it was prepared by E.Schmidt and R.Wilkendorf. Thereafter, the British pharmacognoso CIA committee published its generic name as Bronopol, and received a British patent in 1970 for agriculture. |
| Use | brospall is effective against a wide range of plant pathogenic bacteria and is mainly used as a seed treatment agent, etc. In addition, because of its broad-spectrum antibacterial property, it has been used as a disinfectant in medicine in the 60 s of the last century. With the increasing development of cosmetics, coupled with broad-spectrum antimicrobial, and water-soluble, into the late of the 20th century, 80 s, as a cosmetic preservative use and rapid development. In recent years, bropole has been widely used in feed, paint, fur anti-corrosion, air conditioning circulating water antibacterial, oil field water injection antibacterial and aircraft, ship Disinfection and other aspects, the demand increased rapidly. as a broad-spectrum antimicrobial agent of bromonopol type, brospar has the following characteristics: spectrum antibacterial activity, in the range of pH 4~9 in emulsion products containing surfactants, and high concentration of protein substances in the formula, with effective antibacterial activity, especially for the antibacterial activity of Pseudomonas aeruginosa has special effects; Non-toxic, non-irritating, non-allergic, the dosage of the preservative in cosmetics is 0.01% ~ 005%, and the toxicity test results show that the preservative is safe and is one of the cosmetic preservatives approved by FDA in the United States. According to the U. S. FDA statistics, among all the preservatives used in cosmetics, brogpole's frequency of use ranked first. It is the sharp increase in commercial demand, which has promoted the research and industrial production of brospar. bactericide. It can effectively control a variety of plant pathogenic bacteria. The treatment of cotton seeds can prevent cotton black arm disease and bacterial blight disease caused by cotton angular leaf spot fungus, and has no damage to cotton. It can also be used for rice seedling disease. It is recommended to use the concentration of 800 ~ 1000mg/L. mainly used for cosmetics, leather anti-corrosion, in agriculture is mainly used for prevention and control of rice seedling disease biocide, mainly used in industrial circulating water, paper pulp, paint, plastics, cosmetics, wood, cooling water circulation system, and industrial use of sterilization, anti-mildew, anti-corrosion, algae, etc. widely used in water treatment, pharmaceuticals, pesticides, cosmetics, detergents and other industries as preservatives and sterilants cosmetics preservatives, added in shampoo, Balsam and cream and other cosmetics processing, bactericidal concentrations in cosmetics range from 0.01% to 0.02%. It can also be used for detergents, fabric treatment agents, etc. A broad-spectrum and efficient industrial fungicide used to prevent the growth and reproduction of bacteria and algae in paper making, industrial circulating cooling water, lubricating oil for metal processing, Pulp, wood, paint and plywood, at the same time can do slime control agent, widely used in paper mill pulp and circulating cooling water system. mainly used in medical disinfectants, cosmetics preservatives, can also be used as pesticide treatment agent |
| synthesis | the organic synthesis process of brospar mainly adopts the following methods: first, nitromethane and formaldehyde are condensed to form an intermediate, 2-nitro-1, 3-propanediol, and then bromination reaction is carried out with bromine to obtain brogopol product; second, the bromination reaction of nitromethane with bromine is carried out to prepare a bromitromethane intermediate, and a single brogopol product is obtained by directly condensing with formaldehyde. method-the process route of nitromethane and formaldehyde condensation first, and then bromination reaction with bromine to obtain brogpol product. The reaction mechanism of this process is as follows: FIG. 1 is the first synthesis method of brogopol. The use of this principle for the preparation of brospall reports, the first found in 223, in anhydrous alcohol, in the presence of alkali metal, the role of nitromethane and formaldehyde, condensation reaction, the resulting basic salt of the intermediate nitroalcohol was isolated and taken up in an organic solvent to give brogpole. Similar synthetic methods have been reported in Germany and France in 1970. methods the intermediate of bromonitromethane was prepared by bromination reaction of dinitromethane with bromine firstly, and the pure monobromonitro methane was directly condensed with formaldehyde to obtain the synthesis process of brogopol product. The process principle of this method is as follows: FIG. 2 is the second synthesis method of brolpol. In 1990, the United States and the United States in 1991, the preparation methods of halogenated nitroalcohols and brominated nitroalcohols were proposed successively. In this method, the bromination reaction of nitromethane with bromine is proposed to prepare a bromitromethane intermediate, and then a bromboer product with high purity is prepared by chemical reaction of bromonitromethane with formaldehyde. The intermediate monobromonitromethane obtained by this method is very stable and easy to purify. The obtained product has less impurity content, simple post-treatment, and does not require any organic solvent in the crystallization process. The product has large crystal size, good crystal form and high purity, which meets the requirements of British Pharmacopoeia BP2000 standard and can fully meet the needs of export. The yield of the process is about 88% ~ 90%. |
| Process Improvement | The traditional synthesis method of brospall mainly through the first addition and then bromination, in the bromination reaction must use ethyl acetate, non-polar toxic flammable solvents such as carbon tetrachloride or dichloroethane; The formation of the basic salt of the intermediate nitroalcohol in the addition reaction is unstable, and these shortcomings are extremely unfavorable for industrial production. Therefore, it is necessary to improve the synthesis route, first of nitromethane bromination reaction to generate a stable intermediate product of bromonitromethane, and then the addition reaction to generate brogpo. The intermediate bromonitromethane synthesized by the new method is an important organic chemical product. At present, there is no production of this product in China, which has a very broad development prospect. |
| toxicity | Acute Oral LD50180 ~ 400mg/kg in rats, acute oral LD50270 ~ 400mg/kg in mice, dog acute oral LD50200mg/kg. Rat acute percutaneous LD50>1600mg/kg. It has moderate irritation to rabbit skin and mild irritation to eyes. No teratogenic, carcinogenic or mutagenic effects were observed in animal experiments. |
| references | [1] Qu Yang. Study on the synthesis of antimicrobial preservatives brogboer and Carmine [D]. Qingdao University of Science and Technology, 2010. [2] Qu Yang, Liu Fu-sheng, Liu Shi-wei, Yu Shi-Tao. Synthesis and purification of bromass [J]. Progress in fine petrochemicals, 2010,11(05):9-12. [3] Yuan Jun, Zeng Ying, Xiang Jianmin. A new method for the synthesis of bromass [J]. Fine Chemicals, 1997,(05):49-51. [4] Wang Jinbang, Fu qingou, Wang Xiuling. The antiseptic effect of Bronopol in cosmetics [J]. Fine Chemicals, 1988,(04):21-28. |
| Chemical properties | This product is colorless or tan crystal. m. P. 130 °c, vapor pressure 1.68 x 10-3Pa. Soluble in acetone, 2-methoxyethanol, toluene and other organic solvents, 22 ° C water solubility of 250g/L. Industrial purity is higher than 90%, a slight hygroscopicity. |
| production method | by nitromethane and formaldehyde, bromine reaction, there are two kinds of operation process. (1) nitromethane, 30% formaldehyde, calcium chloride and sodium hydroxide are added to the reaction device according to the molar ratio of 1:2:2:2, A solution of bromine and dichloroethane was added dropwise below 0 °c. After 1H addition, the amount of bromine was equimolar to nitromethane. The dichloroethane layer was separated and the dichloroethane was distilled off. A white solid (crude) was obtained. The aqueous layer of the reactant was extracted with ether, and the ether in the ether extract was distilled off to obtain a further portion of the crude product. The crude product was combined and recrystallized from diethyl ether to obtain a pure product. (2) preparation of 2-nitro-1, 3-propanediol The nitromethane and 30% formaldehyde solution are added to the Reflux reaction device at a molar ratio of 1:2, and then 2% potassium carbonate is added, heated and refluxed for 1H, cooled and crystallized. Extract with diethyl ether, dry, distill off diethyl ether to give 2-nitro-1, 3-propanediol. This was then dissolved in methanol, 20% sodium methoxide in methanol was added, and the mixture was stirred at 20 ° C. To precipitate sodium 2-nitro-1, 3-propanediol. The sodium salt is filtered off and suspended in dry diethyl ether for bromination: bromine is added dropwise to a suspension of sodium 2-nitro-1, 3-propanediol in diethyl ether below 0 °c, after dropping, stir for 10min. Filtration and evaporation of the ether gave 2-bromo-2-nitro-1, 3-propanediol. put metered amount of nitromethane, formaldehyde, water and ethanol into the reaction kettle, and add 40% liquid alkali Dropwise under cooling. At this time, solid precipitates out, part of the water and ethanol were distilled off under reduced pressure. After cooling, crystallization, filtration and drying, the yield of advanced bromonol was ≥ 70%, and the content was about 93%. |
| category | pesticide |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 180 mg/kg; Oral-mouse LD50: 270 mg/kg |
| stimulation data | Skin-rabbits were mild at 500 mg/24 h; eye-rabbit 5 mg moderate |
| flammability hazard characteristics | toxic bromide and NOx emissions from thermal decomposition |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from food raw materials |
| extinguishing agent | water, dry powder, dry sand, carbon dioxide, foam, 1211 extinguishing agent |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:01
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Raw Materials for 3-diol (Bronopol)