OPCl3
Phosphorus oxychloride
CAS: 10025-87-3
Molecular Formula: Cl3OP
OPCl3 - Names and Identifiers
| Name | Phosphorus oxychloride |
| Synonyms | OPCl3 oxychloride Fosforoxychlorid Phosphoroxidchlorid Phosporus Oxychoride Phosphorus oxychlori oxychloridfosforecny Oxychlorid fosforecny Phosporus Oxychloride Phosphortrichloridoxid Phosphorus oxychloride phosphoric trichloride phosphollJs oxychloride Phosphorus oxytrichloride Phosphorus oxitrichloride Phosphorus chloride oxide (POCl3) |
| CAS | 10025-87-3 |
| EINECS | 233-046-7 |
| InChI | InChI:1S/Cl3OP/c1-5(2,3)4 |
| InChIKey | XHXFXVLFKHQFAL-UHFFFAOYSA-N |
OPCl3 - Physico-chemical Properties
| Molecular Formula | Cl3OP |
| Molar Mass | 153.33 |
| Density | 1.645 g/mL at 25 °C(lit.) |
| Melting Point | 1.25°C(lit.) |
| Boling Point | 107 °C |
| Flash Point | 105.8°C |
| Water Solubility | reacts exothermically |
| Solubility | Phosphorus(V) oxychloride is soluble in many organic solvents. |
| Vapor Presure | 104 mm Hg ( 50 °C) |
| Vapor Density | 5.3 (vs air) |
| Appearance | Liquid |
| Specific Gravity | 1.692 (15/15℃) |
| Color | Colorless |
| Odor | Pungent odour |
| Exposure Limit | TLV-TWA0.628 mg/m3 (0.1 ppm)(ACGIH). |
| Merck | 14,7349 |
| PH | 1.0 (5g/l, H2O, 25℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Reacts violently with water. Incompatible with many metals, alcohols, amines, phenol, DMSO, strong bases. |
| Sensitive | Moisture Sensitive |
| Refractive Index | n20/D 1.461 |
| Physical and Chemical Properties | See phosphorus oxychloride. |
OPCl3 - Risk and Safety
| Risk Codes | R14 - Reacts violently with water R22 - Harmful if swallowed R26 - Very Toxic by inhalation R29 - Contact with water liberates toxic gas R35 - Causes severe burns R48/23 - R25 - Toxic if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S7/8 - S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | UN 1810 8/PG 2 |
| WGK Germany | 1 |
| RTECS | TH4897000 |
| FLUKA BRAND F CODES | 19-21 |
| TSCA | Yes |
| HS Code | 28121020 |
| Hazard Class | 8 |
| Packing Group | II |
OPCl3 - Reaction with water
When phosphorus oxychloride (POCl3) reacts with water (H2O), a hydrolysis reaction occurs. The process can be described in detail as follows:
1. The phosphorus oxychloride molecule (POCl3) reacts with a water molecule (H2O) to form an intermediate product, H3PO3Cl:
POCl3 + H2O → H3PO3Cl
2. The intermediate product H3PO3Cl further decomposes into phosphorous acid (H3PO3) and hydrochloric acid (HCl):
H3PO3Cl → H3PO3 + HCl
3. The final products of the reaction are phosphorous acid (H3PO3) and hydrochloric acid (HCl). The phosphorous acid can then be further oxidized to form orthophosphoric acid (H3PO4).
The overall reaction equation can be represented as:
POCl3 + 3H2O → H3PO4 + 3HCl
This reaction is a hydrolysis reaction where phosphorus oxychloride decomposes in water to produce phosphorous acid and hydrochloric acid, accompanied by the release of heat.
Last Update：2024-04-09 19:55:45
OPCl3 - React with dimethylamine
When phosphorus oxychloride (POCl3) reacts with dimethylamine ((CH3)2NH), it will produce dimethylaminochlorophosphine ((CH3)2NPCl3) and hydrochloric acid (HCl).
The reaction can be described as follows:
POCl3 + 2(CH3)2NH → (CH3)2NPCl3 + HCl
In a laboratory setting, this reaction will result in the formation of dimethylaminochlorophosphine and the release of hydrochloric acid gas. Proper safety measures, including ventilation, should be in place to handle any gas evolution during the reaction.
In a laboratory setting, when phosphorus oxychloride (POCl3) reacts with dimethylamine ((CH3)2NH), the following scenario may occur:
1. Prepare solutions of POCl3 and (CH3)2NH in separate containers. POCl3 is a colorless liquid, while (CH3)2NH is a clear or pale yellow liquid.
2. Slowly add the (CH3)2NH solution to the POCl3 solution. Gas evolution may be observed as the reaction initiates. A color change in the solution may also be noted.
3. As the reaction progresses, (CH3)2NH will react with POCl3 to form dimethylaminochlorophosphine ((CH3)2NPCl3) and hydrochloric acid (HCl). Dimethylaminochlorophosphine is a colorless or pale yellow liquid.
4. Gas evolution may occur during the reaction; therefore, it is important to ensure proper ventilation in the laboratory to prevent the accumulation of gases.
5. Lastly, collect the reaction products, perform necessary analysis, and proceed with appropriate disposal procedures.
Safety measures should be observed during this reaction in the laboratory, including wearing appropriate protective gear, working in a well-ventilated environment, and properly handling any generated waste.
Last Update：2024-04-09 19:55:45
OPCl3 - Reaction with DMF
The reaction between phosphorus oxychloride (POCl3) and dimethylformamide (DMF) can result in the formation of the corresponding amide compound. The reaction equation is as follows:
POCl3 + DMF → DMF-Cl + HCl
In this reaction, POCl3 acts as the acylating agent, which can replace the oxygen atom in the carbonyl group of DMF with a chlorine atom, forming the chlorinated amide product DMF-Cl. The generated HCl is a byproduct that will precipitate out of the reaction system. This reaction is typically carried out under anhydrous and oxygen-free conditions, and the purity and yield of the product can be controlled by adjusting the temperature and reaction time.
Last Update：2024-04-09 19:55:45
OPCl3 - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | phosphorus oxychloride (molecular formula: POCl3), also known as phosphorus oxychloride, phosphorus oxychloride, phosphorus oxychloride, is an industrial chemical raw materials, it is a colorless transparent liquid. Irritating odor. Smoke was generated vigorously in humid air. The relative density was 1.67. Melting point 1.25 °c. Boiling point 105.1 °c. In water, ethanol decomposition of phosphoric acid and hydrogen chloride. When a large amount of water is poured suddenly, a severe reaction can occur. POCl3 reacts with water and alcohol to generate phosphoric acid or phosphate ester, such as: O = PCl3 3 H2O → O = P(OH)3 3 HCl if alcohol replaces water in the reaction, then the product is a trialkyl phosphate. Such reactions are usually carried out in pyridine or amine to absorb the HCl formed and drive the reaction to proceed. The triaryl phosphate is obtained by coheating POCl3 with excess phenol (ArOH) catalyzed by a Lewis acid such as manganese chloride. For example reaction with phenol: 3 C6H5OH O = PCl3 → O = P(OC6H5)3 3 HCl, phosphorus oxychloride is a Lewis base and forms adducts with many Lewis acids. Such as the reaction with titanium tetrachloride: Cl3P -O − TiCl4 → Cl3P -O-− TiCl4 and aluminum chloride adduct (POCl3 · AlCl3) is very stable, POCl3 was therefore also used to remove AlCl3 from the Friedel-Crafts reaction product. In the presence of AlCl3, POCl3 reacts with hydrogen bromide to form pobr3. It is produced industrially from the reaction of phosphorus trichloride with oxygen or phosphorus pentoxide and is used primarily for the production of phosphate esters such as tricresyl phosphate. |
| molecular structure | The phosphorus atom in phosphorus oxychloride is tetrahedral configuration, containing three P-Cl bonds and one P = O double bond, P = O bond dissociation energy is approximately 533.5kJ/mol. According to the data of bond length and electronegativity, according to the Schomaker-Stevenson rule, it is considered that the double bond type contributes more in the following resonance formula, but the structure of charge separation type contributes more in the same family of pof3. The P = O double bond is not similar to the carbonyl pi bond in the ketone. In the previous teaching materials, it is considered that the p orbital of phosphorus d orbital and oxygen is overlaid, now, most of the P-O bonds are considered to be related to the P-Cl bond sigma * anti bond orbital, and the role of the d orbital is not considered. |
| knowledge of toxicity and first aid | Introduction to toxicology rat oral LD50: 380 mg/kg; Inhalation LC50: 32 ppm/4H. The toxicity was similar to phosphorus trichloride, phosphorus pentachloride and phosgene. Acute poisoning in mice showed restlessness, upper respiratory tract and eye conjunctival irritation, inhibition, convulsions, gait instability, lateral, and finally died. In addition to the above manifestations, the rats had tears, corneal opacity and pulmonary edema. Due to the strong oxidation and lipid soluble effect, in addition to cause digestive tract Burns, the digestive tract absorption of the liver can cause acute necrosis and autolysis. In addition, the goods in addition to cause skin burns, but also through the integrity of the skin absorption, 3% can cause animal death. After inhalation of phosphorus oxychloride, the moist respiratory mucosa can be decomposed into phosphoric acid and hydrogen chloride, which can stimulate and corrode the mucosa. Human exposure to 70mg/m ^ 3 concentration, the occurrence of acute poisoning. General 2-6h latency and symptoms, respiratory mucosa irritation, eye pain. Severe cases have a sense of suffocation, cyanosis, pulmonary edema, heart failure. Anemia, liver damage, and Proteinuria may also occur. When the workshop temperature is high and the relative humidity is low, inhalation poisoning is easy to occur. Subacute and chronic toxicity: rats 60 days inhalation test, the concentration of 33.5mg/m3, slow weight growth and skin ulcers, lung macrophage survival rate decreased, no liver and kidney functional, organic changes. Clinical manifestations of this product after exposure to smoke, after 2 to 6 hours of incubation period, there can be symptoms of acute poisoning, Rhinorrhea, throat, Head Pain, Dyspnea. Slightly severe cases of epistaxis, general weakness, blood-stained sputum, nasal septum mucosa burns. Severe cases can occur laryngeal edema caused by asphyxia, Pneumonia or pulmonary edema. Oral liquid can cause digestive tract burns. This liquid can cause irritation symptoms and eye and skin burns. Eye burns after slow healing. Phosphorus poisoning can be caused when phosphorus yellow is contained in impurities. The principle of first aid and treatment after inhalation is the same as that of irritant gases such as chlorine and hydrogen chloride. When this product is contaminated with skin, the liquid should be sucked off with paper, cotton, etc., and then rinsed with water for at least 15 minutes; If it is rinsed with a small amount of water, phosphoric acid can form on the skin and cause more severe burns. Acid burn treatment. GB 81040. Original iron gauge: Grade I inorganic acid corrosion article, 91022. UN No. 1810. IMDG CODE page 8197, category 8. |
| Use | phosphorus oxychloride is most commonly used in the production of triaryl phosphates (e. G., triphenyl phosphate and tricresyl phosphate), which are useful as flame retardants and plasticizers for polyvinyl chloride. It is also used for the preparation of diphenyl-isooctyl phosphate, triethyl phosphate and other phosphate esters, plastic plasticizers, organophosphorus pesticides, long-acting sulfonamide drugs and so on. It can also be used as dye intermediates, chlorinating agents and catalysts in organic synthesis. The use of electronic grade phosphorus oxychloride in the solar energy industry, integrated circuits, separation devices, light preforms and other liquid phosphorus sources can also be prepared phosphate. Trialkyl phosphates such as tributyl phosphate (prepared from 1-butanol by a similar reaction) are solvent for liquid-liquid extraction and are used in industries such as nuclear fuel reprocessing. In the semiconductor industry, POCl3 is also used as a source of phosphorus in the diffusion process to produce N-type silicon semiconductors by doping. The amide was converted to a nitrile in the laboratory using POCl3 as a water loss agent. Certain amides can be cyclized by a Bischler-Napieralski reaction to produce a derivative of dihydroisoquinoline. If the above reaction is sufficiently stable via the R-C(= NH)-Cl(imidoyl chloride) Intermediate, the reaction may remain at this stage. For example, POCl3 can convert pyridinone and pyrimidinone into corresponding chloro products, and is an important precursor in the pharmaceutical industry. At 140°C, phosphorus oxychloride reacts with barbituric acid to form 2,4, 6-trichloropyrimidine. In the presence of phosphorus oxychloride, the activated aromatic rings react Vilsmeier-Haack to give aromatic aldehydes or Aromatic ketones. The acylating reagent in the reaction is usually DMF or N-phenyl-N-methyl formamide, and the intermediate imine salt is easily hydrolyzed to form an aldehyde. For example, 9-anthracene formaldehyde is obtained using anthracene as a reactant. It is used as a semiconductor dopant and as a raw material of an optical fiber. It is widely used in the production of pesticides, pharmaceuticals, dyes, phosphate esters and flame retardants. It is a raw material for the manufacture of organophosphorus pesticide herbicides, chlordimeform and other raw materials for the production of plastic plasticizers. It is also used for chlorination of long-acting sulfonamides, which is an intermediate for the production of dyes, chlorinating agents and catalysts for organic synthesis, uranium extraction agents, etc. is a raw material for producing chlordimeform, an organophosphorus pesticide. For the production of phosphoric acid diphenyl-isooctyl Ester, phosphoric acid triethyl Ester phosphate and the production of plastic plasticizer. For the chlorination of long-acting sulfonamides. Production of dye intermediates, organic synthesis of chlorinating agents and catalysts, uranium extraction agent. phosphorus oxychloride is commonly known as phosphorus oxychloride, which is mainly used in the synthesis of another phosphorus-containing intermediate-phosphoryl chloride or phosphoryl dichloride, such as O,O-diethyl phosphoryl chloride, and then the synthesis of pesticide ethyl sulfur cyclic phosphorus, or synthesis of O-ethyl phosphorus chloride, and then synthesis of pesticide phosphorus. In other aspects, phosphorus oxychloride can be used as a chlorinating agent, a catalyst, a plastic plasticizer, a dye intermediate, etc., and is also used in the pharmaceutical industry and organic synthesis. |
| preparation method | phosphorus trichloride is added with water, chlorine is introduced, chlorination and hydrolysis are carried out, and the reactants are vaporized by heating, after condensation, the reaction mixture was reheated until the color of the reaction mixture was white. Phosphorus oxychloride can also be prepared by reacting phosphorus trichloride with oxygen at 20-50°C (less efficient using air):2 PCl3 O2 → 2 O = PCl3 or using the reaction of phosphorus pentachloride with phosphorus pentoxide. However, the reactants are all solid, and the reaction effect is not good. The mixture of PCl3 and P4O10 is chlorinated with chlorine gas, and the resulting PCl5 is reacted with P4O10 at the same time, and the effect is better. POCl3 produced by itself can be used as reaction solvent: 6 PCl3 6 Cl2 → 6 PCl5 6 PCl5 P4O10 → 10 POCl3 POCl3 will also be produced when phosphorus pentachloride is hydrolyzed, but there are many side reactions, and the reaction is not easy to control. |
| quenching method | under stirring, add to a large amount of ice water (can not be added back), confirm the reaction and then neutralize with alkali, for phosphorus oxychloride that does not react with ice water immediately, it can be slowly poured into water at room temperature to confirm that the reaction is finished, then it is added, ice cooling is added from time to time, and finally neutralization with alkali under cooling. During the treatment, it can only be slowly added to water (alkali solution), and water must not be added to the above compounds. |
| precautions for use | phosphorus oxychloride is often used in industrial production, and there are many details in the use of phosphorus oxychloride, it will cause safety problems and cause accidents. The following matters should be noted: 1. Phosphorus oxychloride is prepared, and many factories pump phosphorus oxychloride to the storage tank by water jet vacuum, therefore, attention should be paid to the start and stop sequence of water jet vacuum to prevent accidents. In particular, the vacuum buffer tank should be checked frequently to prevent water from drawing up into the storage tank and causing accidents. 2, phosphorus oxychloride hydrogen chloride, attention should be paid to prevent phosphorus oxychloride drops over, if the drop is over, be sure to slowly add water to decompose phosphorus oxychloride and then discharge phosphoric acid. 3, the hydrolysis of the material containing phosphorus oxychloride is generally recommended to slowly put the material into the hydrolysis kettle with ice water, and constantly stir, as far as possible not to add water to the material, it will be very dangerous operation. 4, where the use of phosphorus oxychloride system, should be as much as possible to detect the moisture of all materials, to prevent the occurrence of explosion accidents. 5, the use of phosphorus oxychloride reactor is often to check the wall of the kettle is damaged, to prevent water leakage into the accident. 6. When phosphorus oxychloride is dropped into the reactor, Should pay attention to observe whether there is abnormal situation, if there is immediately stop feeding, check the reason after feeding reaction. 7, phosphorus oxychloride low temperature and water reaction is slow, then we must pay attention to the drop of a slow point, to prevent the sudden reaction accident. 8, phosphorus oxychloride can be used with dichloroethane, toluene and other solvents, but not with alcohol, amine solvents. |
| toxicity | see phosphorus oxychloride. The volatile gas of phosphorus oxychloride is toxic, irritant and corrosive, and can irritate the mucous membrane and cause eye pain. Dry Cough, the emergence of severe Dyspnea, after the occurrence of bronchitis, heart insufficiency, severe anemia, hepatomegaly, urine protein, lung enlargement. Droplets within the conjunctival sac of the eye, necrosis and complete loss of vision will occur. The maximum allowable concentration is 0.05 mg/m3. Operators should wear protective equipment. Production of phosphorus oxychloride equipment to be closed. Filter-type gas masks can be worn during work. Carefully protect the skin and eyes. |
| production method | the preparation method is to oxidize phosphorus trichloride as raw material, if different oxidants are used, there are a number of different methods of preparation. The chlorination hydrolysis method is mainly used in industry, that is, phosphorus trichloride is added into the reactor, chlorine gas is introduced, and water is added dropwise at the same time to control a certain ratio of chlorine to water, chlorine and dripping speed, the reactants in the reactor were gasified by heating to 105-109 °c with jacketed steam, condensed through a condenser and fed back into the reactor. Chlorine gas was introduced twice, and the residual phosphorus trichloride was continued to be chlorinated. Reflux to the reactant color white, phosphorus trichloride residual stock below 0.2%, can be exported by the condenser as phosphorus oxychloride product. The hydrogen chloride gas generated by the reaction of PCl3 + Cl2 + H2O = POCl3 + 2HCl is absorbed by water to generate dilute hydrochloric acid. In addition, phosphorus oxychloride can also be obtained by passing dry oxygen into phosphorus trichloride, or by the interaction of phosphorus pentoxide with phosphorus pentachloride, or by using chlorine and sulfur dioxide as an oxidant. phosphorus trichloride is added into the reactor by chlorination hydrolysis method, chlorine is introduced into the reactor, and water is added dropwise at the same time to control the ratio of chlorine to water at about 3.94, the chlorine and drip rates were 25-35kg/h and 6.25-8.8/h, respectively. The reactants in the reactor were vaporized by heating to 105-109 °c with jacketed steam, condensed through a condenser, and then fed back into the reactor. Chlorine gas was introduced twice, and the residual phosphorus trichloride was continued to be chlorinated. Reflux to the reactant color white, phosphorus trichloride residual stock below 0.2%, can be exported by the condenser as phosphorus oxychloride product. The hydrogen chloride gas generated by the reaction of PCI3 + C12 + H2O → POCl3 + 2HCl + is absorbed by water to generate dilute hydrochloric acid. with reagent grade phosphorus oxychloride as raw material, it was added into quartz distillation equipment for rectification and refining to prepare high purity phosphorus oxychloride product. |
| category | corrosive article |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 380 mg/kg |
| flammability hazard characteristics | toxic chloride and phosphorus oxide gases |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from alkalis |
| fire extinguishing agent | dry sand, dry stone powder; No water |
| Occupational Standards | TLV-TWA 0.1 PPM (0.6 mg/m3); PEL 0.5 PPM (3 mg/m3) |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:55:45
OPCl3 - Nature
Open Data Verified Data
is a colorless and highly corrosive liquid. dzs l.645; Boiling point 105.8 °c; Melting point 125 °c. Smoke in the humid air, there is a strong stimulation, the occurrence of severe decomposition in water. In the water bottom, and water intense reaction to generate toxic or corrosive phosphoric acid and hydrochloric acid. It decomposes vigorously when exposed to water, producing a large amount of heat and smoke, and even explosion. It has strong corrosion. Contact with air to form corrosive gases. With acids, alcohols, alkali metals, corrosion agents, combustible substances, carbon disulfide, dimethyl formamide, organic matter, alkali, zinc powder contact reaction. In a humid environment, in addition to lead, can rapidly corrode steel and most metals.
Last Update：2024-01-02 23:10:35
OPCl3 - Preparation Method
Open Data Verified Data
with reagent grade phosphorus oxychloride as raw material, it was added into quartz distillation equipment for rectification and refining to obtain high purity phosphorus oxychloride finished product.
Last Update：2022-01-01 08:54:16
OPCl3 - Use
Open Data Verified Data
mainly used for the preparation of the compound semiconductor, optical fiber and for semiconductor doping
Last Update：2022-01-01 08:54:16
OPCl3 - Safety
Open Data Verified Data
rat oral LDso:380mg/kg; Rat inhalation 4H LCsa:32 x 10-6. Toxic l its toxicity is similar to phosgene. On the eyes, respiratory tract mucosa irritation, can cause eye and skin burns. The staff should be protected and the working environment should have good ventilation conditions. This product should be stored in a cool, ventilated, dry warehouse. The container must be sealed. It is not allowed to be stored and mixed with flammable articles, deliquescent articles and alkaline substances. During the transport process to prevent rain, moisture, sun exposure. Handle with care to prevent impact and rupture of the packaging bottle.
Last Update：2022-01-01 08:54:17
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