Hydroxydiphenylphosphine oxide
Diphenylphosphinic acid
CAS: 1707-03-5
Molecular Formula: C12H11O2P
Hydroxydiphenylphosphine oxide - Names and Identifiers
| Name | Diphenylphosphinic acid |
| Synonyms | AURORA KA-1519 diphenyl-phosphinicaci DIPHENYLPHOSPINIC ACID Diphenylphosphine acid Diphenylphosphonic acid DIPHENYLPHOSPHONIC ACID DIPHENYLPHOSPHINIC ACID Diphenylphosphinic acid Phosphinic acid, diphenyl- Hydroxydiphenylphosphine oxide |
| CAS | 1707-03-5 |
| EINECS | 216-948-5 |
| InChI | InChI=1/C12H11O2P/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H,13,14) |
Hydroxydiphenylphosphine oxide - Physico-chemical Properties
| Molecular Formula | C12H11O2P |
| Molar Mass | 218.19 |
| Density | 1.25±0.1 g/cm3(Predicted) |
| Melting Point | 193-195°C(lit.) |
| Boling Point | 194 °C |
| Flash Point | 223.7°C |
| Water Solubility | Soluble in water. |
| Solubility | 0.1 M NaOH: soluble0.5g/10 mL, clear, colorless |
| Vapor Presure | 9.59E-09mmHg at 25°C |
| Appearance | White crystal powder |
| Color | White |
| BRN | 2804567 |
| pKa | 2.30±0.10(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.602 |
| MDL | MFCD00002132 |
Hydroxydiphenylphosphine oxide - Risk and Safety
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | SZ5315000 |
| HS Code | 29310095 |
Hydroxydiphenylphosphine oxide - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| overview | diphenylphosphoric acid is an important pharmaceutical and pesticide intermediate. At present, the reported preparation method is that benzene and phosphorus trichloride use benzene as a solvent, aluminum trichloride as an acid agent to make phenyl phosphorus dichloride, and phenyl phosphorus dichloride use aluminum trichloride as a catalyst for disproportionation The reaction is made into diphenylphosphorus chloride, which is oxidized to diphenylphosphoryl chloride by oxygen under deep cooling, and then hydrolyzed to diphenylphosphoric acid. However, the existing synthesis process of diphenylphosphoric acid is highly polluting, requires high equipment performance, the total yield is only 30%, and the cost is high. |
| preparation | a preparation method of diphenylphosphoric acid specifically includes the following steps: 1) putting 208g of toluene and 184g(1.2mol) phosphorus oxychloride into a 1000ml four-mouth bottle, cooling to 15 ℃ with ice water, adding 208g of toluene and 219g(3mol) diethylamine mixed solution dropwise between 15 and 25 ℃, after dropping, heat preservation at 15~25 ℃ for 3 hours; The reaction principle of this step is as follows: 2) the material after the reaction in step 1) is filtered to recover the diethylamine hydrochloride of the reaction product, the diethylamine hydrochloride can be treated into diethylamine as raw material for reuse, then the filtrate is distilled at normal pressure to recover the solvent toluene, and the distillation at 132~136 ℃ and-0.096MPa is continuously distilled under reduced pressure to obtain 205g(1.08mol) of diethylamine dichlorophosphate, the reaction yield was 90%. 3) Mix 2g tetrahydrofuran, 2g chlorobenzene and 0.5ml bromobenzene to form an initiator for later use. 4) 140g chlorobenzene, 100g tetrahydrofuran and 65g toluene are mixed in a 500ml bottle to prepare a mixed solution. 5) Add 27g(1.125mol) magnesium strips into a 1000ml dry reaction bottle, stir and heat, heat to 50 ℃ to stop heating, make the heating temperature reach 60~70 ℃ through waste heat, add the initiator prepared in step 3) to carry out Grignard reaction, and observe whether there is any reaction initiated phenomenon in the reaction bottle, a large amount of white smoke is generated in the reaction bottle, and the temperature rises rapidly, indicating that the reaction has been initiated. 6) Step 5) When the temperature in the reaction bottle stops rising, drop the mixed liquid prepared in step 4) shall be kept dropwise at 100~110 ℃, with the maximum not exceeding 120 ℃ and the minimum not below 90 ℃. After the mixed liquid droplets are added, keep the temperature at 90~110 ℃ for 2 hours, and cool down to 55 ℃ after the reaction. 7) The 205g(1.08mol) dichlorophosphoryl diethylamine obtained in step 2) is mixed with 65g toluene to make a mixed solution. When the temperature drops to 55 ℃ after the reaction in step 6), the mixed solution is added dropwise, and the temperature of the mixed droplets is controlled to be 55~65 ℃. After the dropwise addition is completed, the reaction is kept at 55~65 ℃ for 3 hours, and the reaction product is collected; 8) Add 100g of hydrochloric acid and 230g(12.8mol) of water into a 2000ml four-mouth bottle, stir and control the temperature in the four-mouth bottle to 30~40 ℃, drop the reaction product collected in step 7) into the four-mouth bottle, and heat up to 70~80 ℃ for reflux reaction for 4 hours after dropping; The reaction principle is as follows: cooling and filtering, collecting solid matter and drying to obtain 178g(0.92mol) of diphenylphosphoric acid, the yield of Grignard reaction and hydrolysis reaction in steps 5) to 8) is 85%. The total yield of diphenylphosphoric acid in this product is 76.6% based on phosphorus oxychloride. |
Last Update：2024-04-10 22:29:15
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