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Encyclopedia > Phosphorus trichloride
Phosphorus trichloride
Phosphorus trichloride
Phosphorus trichloride
General
Systematic name Phosphorus trichloride
Other names Phosphorus(III) chloride
Phosphorous chloride
Molecular formula PCl3
Molar mass 137.33 g/mol
Appearance clear, colourless liquid
CAS number [7719-12-2]
EINECS number 231-749-3
MSDS Wikisource MSDS
Bulk properties
Density 1.574 g/cm3
Solubility Water: rapid hydrolysis

Methanol: decomposes Image File history File links Chemical Structure of Phosphorus Trichloride H Padleckas created this image file on April 21, 2005 from a similar image in Wikipedia for the Phosphorus tribromide article, especially for use in the article Phosphorus chlorides in Wikimedia. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of an element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Water is in dynamic equilibrium between the liquid and solid states at standard temperature and pressure. ... Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. ... Methanol, also known as methyl alcohol or wood alcohol, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid that is used as an antifreeze, solvent, fuel, and as a denaturant for ethyl alcohol. ... Rotting fruit Decomposition is the reduction of bodies and other formerly living organisms into simpler forms of matter and, most particularly, to the fate of the human body after death. ...


Benzene: soluble Benzene, C6H6, PhH, or benzol is a colorless and flammable liquid with a pleasant, sweet smell. ...


Chloroform: soluble Chloroform (also known as trichloromethane and methyl trichloride) is a chemical compound with formula CHCl3. ...


Diethyl ether: soluble Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a typical smell. ...

Melting point -93.6 °C (179.6 K)
Boiling point 76.1 °C (349.3 K)
Standard enthalpy
of formation
ΔfH0liq
−319.7 kJ/ mol (liquid)
Hazards Corrosive, toxic,

reducing agent, The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change state from a liquid to a gas throughout the bulk of the liquid. ... The standard enthalpy of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of that substance from its component elements, at their standard states (the most stable form of the element at 25 degrees Celsius and 100 kilopascals). ... A kilojoule (abbreviation: kJ) is a unit of energy equal to 1000 joules. ... The mole (symbol: mol) is one of the seven SI base units and is commonly used in chemistry. ...


reacts with water & alcohols

Structure
Molecular geometry Trigonal pyramidal
Bond angle 100 °
Bond length P-Cl 204 pm (2.04 Å)
Dipole moment 0.56 D
Related compounds
Other trichlorides Nitrogen trichloride

Arsenic trichloride Geometry of the water molecule Molecules have fixed equilibrium geometries--bond lengths and angles--that are dictated by the laws of quantum mechanics. ... Geometry of the water molecule Molecules have fixed equilibrium geometries--bond lengths and angles--that are dictated by the laws of quantum mechanics. ... Geometry of the water molecule Molecules have fixed equilibrium geometries--bond lengths and angles--that are dictated by the laws of quantum mechanics. ... An angstrom or ångström (Å) is a non-SI unit of length equal to 10−10 metres, 0. ... This article is about the electromagnetic phenomenon. ... ...


Antimony trichloride

Related phosphorus

compounds

Phosphorus pentachloride

Phosphorus oxychloride Phosphorus Trichloride Phosphorus Pentachloride Phosphorus trichloride (PCl3) and phosphorus pentachloride (PCl5) are reactive chemicals used as chlorinating reagents in a chemical laboratory. ... Phosphorus trichloride Phosphorus pentachloride (gas phase structure) Phosphorus oxychloride[1] Phosphorus trichloride (PCl3) and phosphorus pentachloride (PCl5) are reactive chemicals used as chlorinating reagents in a chemical laboratory. ...


Diphosphorus tetrachloride

Other halogens Phosphorus trifluoride

Phosphorus tribromide For the halogen light bulb, click here. ... Phosphorus trifluoride (formula PF3, is a colourless and odourless gas. ... Phosphorus tribromide is a clear colourless liquid. ...


Phosphorus triiodide Phosphorus triiodide (PI3) is an unstable red solid which reacts violently with water. ...

Phosphorus trichloride (formula PCl3) is the most important of the three phosphorus chlorides. It is a toxic corrosive liquid (at room temperature and pressure) which reacts violently with water. It is an important industrial chemical, being used for the manufacture of organophosphorus compounds for insecticides and plasticisers, as well as for making oil additives and flame retardants. It is a reducing agent, being readily oxidised to phosphorus pentachloride or phosphorus oxychloride. This article is about the chemical element. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... Phosphorus Trichloride Phosphorus Pentachloride Phosphorus Oxychloride[1] Phosphorus trichloride (PCl3) and phosphorus pentachloride (PCl5) are reactive chemicals used as chlorinating reagents in a chemical laboratory. ... For a list of biologically injurious substances, including toxins and other materials, as well as their effects, see poison. ... Corrosion is the destructive reaction of a metal with another material, e. ... A liquid will assume the shape of its container. ... Temperature is the physical property of a system which underlies the common notions of hot and cold; the material with the higher temperature is said to be hotter. ... Pressure is the application of force to a surface, and the concentration of that force in a given area. ... Chemical tanks in Lillebonne, France Chemical industry includes those industries involved in the production of petrochemicals, agrochemicals, pharmaceuticals, polymers, paints, oleochemicals etc. ... Insecticide application by crop spraying An insecticide is a pesticide whose purpose is to kill or to prevent the multiplication of insects. ... Plasticizers are plastic additives, most commonly phthalates, that give plastics flexibility and durability. ... Flame retardants are materials that inhibit or resist the spread of fire. ... The most fundamental reactions in chemistry are the redox processes. ... Phosphorus Trichloride Phosphorus Pentachloride Phosphorus trichloride (PCl3) and phosphorus pentachloride (PCl5) are reactive chemicals used as chlorinating reagents in a chemical laboratory. ... Phosphorus trichloride Phosphorus pentachloride (gas phase structure) Phosphorus oxychloride[1] Phosphorus trichloride (PCl3) and phosphorus pentachloride (PCl5) are reactive chemicals used as chlorinating reagents in a chemical laboratory. ...

Contents


Physical properties

Phosphorus trichloride has a dipole moment of 0.8 D in CCl4 and a bond angle of 100.27°. Liquid PCl3 has a standard enthalpy of formation of -319.7 kJ/ mol. The phosphorus atom has an NMR chemical shift of 220 ppm (downfield of H3PO4). A dipole (Greek: dyo = two and polos = pivot) is a pair of electric charges or magnetic poles of equal magnitude but opposite polarity (opposite electronic charges), separated by some (usually small) distance. ... The debye (symbol: D) is a derived CGS unit of electrical dipole moment. ... Carbon tetrachloride (CCl4) is a synthetic chemical compound formerly widely used in fire extinguishers and refrigeration, but now largely abandoned due to its toxicity. ... The standard enthalpy of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of that substance from its component elements, at their standard states (the most stable form of the element at 25 degrees Celsius and 100 kilopascals). ... A kilojoule (abbreviation: kJ) is a unit of energy equal to 1000 joules. ... The mole (symbol: mol) is one of the seven SI base units and is commonly used in chemistry. ... Pacific Northwest National Laboratorys high magnetic field (800 MHz) NMR spectrometer being loaded with sample. ... Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is a weak mineral acid with the chemical formula H3PO4. ...


Chemical properties

In phosphorus trichloride (PCl3), the phosphorus is in the +3 oxidation state and the chlorines are in the -1 oxidation state. PCl3 reacts rapidly and exothermically with water to form phosphorous acid, H3PO3 and HCl. A large number of similar substitution reactions are known, the most important of which is the formation of phosphite esters by reaction with alcohols or phenols. For example, with phenol, triphenyl phosphite is formed: This article is about the chemical element. ... The oxidation state or oxidation number is defined as the sum of negative and positive charges in an atom, which indirectly indicates the number of electrons it has accepted or donated. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... Exothermic has several meanings, including: In biology, an exothermic or poikilothermic animal is one that requires external sources of heat (usually sunlight) to maintain its internal temperature: for example, reptiles. ... Water is in dynamic equilibrium between the liquid and solid states at standard temperature and pressure. ... The phosphite ion is a polyatomic ion with phosphorus as its central atom. ... The chemical substance hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride (HCl) gas. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group (-OH) attached to an aromatic hydrocarbon group. ... Phenol, also known under the old name carbolic acid, is a colorless crystalline solid with a typical sweet tarry odor. ...



3 PhOH + PCl3 → P(OPh)3 + 3 HCl Phenol, also known under the old name carbolic acid, is a colorless crystalline solid with a typical sweet tarry odor. ... Hydrogen chloride, also known under the name HCl, is a highly corrosive and toxic colorless gas that forms white fumes on contact with humidity. ...



where "Ph" stands for phenyl group, -C6H5. Alcohols such as ethanol react similarly in the presence of a base such as triethylamine to give phosphite esters such as triethyl phosphite (ethyl group is -C2H5): In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 Picture where the six carbon atoms are arranged in a cyclic manner. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... The common (Arrhenius) definition of a base is a chemical compound that either donates hydroxide ions or absorbs hydrogen ions when dissolved in water. ... Triethylamine is a tertiary amine with formula N(C2H5)3 and a boiling point around 89 C. Categories: Biology stubs | Amines ... Ethyl is a two-carbon substituent in organic chemistry. ...



3 C2H5OH + PCl3 → P(OC2H5)3 + 3 HCl Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless chemical compound, one of the alcohols that is most often found in alcoholic beverages. ... Hydrogen chloride, also known under the name HCl, is a highly corrosive and toxic colorless gas that forms white fumes on contact with humidity. ...



However without base, the reaction leads to the formation of a dialkyl phosphonate and an alkyl chloride, for example: Alkyl halide ...



PCl3 + C2H5OH → (C2H5O)2P(=O)H + C2H5Cl + 2 HCl Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless chemical compound, one of the alcohols that is most often found in alcoholic beverages. ... Ethyl chloride is a chemical compound once widely used in producing tetraethyl lead, a gasoline additive. ... Hydrogen chloride, also known under the name HCl, is a highly corrosive and toxic colorless gas that forms white fumes on contact with humidity. ...



where ethyl is the alkyl group. Under certain conditions the reaction may lead to only the alkyl chloride and phosphorous acid. The phosphite ion is a polyatomic ion with phosphorus as its central atom. ...


Amines such as R2NH form P(NR2)3, and thiols (RSH) form P(SR)3. The substitution reaction of PCl3 with Grignard reagents and organolithium reagents provides a useful method for the preparation of organic phosphines R3P (sometimes called phosphanes) such as triphenylphosphine, Ph3P. Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ... In chemistry, thiols (formerly known as mercaptans) are those compounds which contain the sulfhydryl group -SH attached to a carbon atom. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ... An organolithium reagent is a carbon nucleophile similar to a Grignard reagent. ... Phosphine is the common name for phosphorus hydride (PH3), also known by the IUPAC name phosphane. ... Triphenylphosphine is a common chemical reagent widely used in organic synthesis. ... In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 Picture where the six carbon atoms are arranged in a cyclic manner. ...



3 PhMgCl + PCl3Ph3P + 3 MgBrCl Triphenylphosphine is a common chemical reagent widely used in organic synthesis. ...



PCl3 will in fact substitute directly onto an aromatic ring, for example benzene will form PhPCl2. Benzene, C6H6, PhH, or benzol is a colorless and flammable liquid with a pleasant, sweet smell. ... In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 Picture where the six carbon atoms are arranged in a cyclic manner. ...


Phosphorus trichloride has a lone pair, and therefore can act as a Lewis base, for example with the Lewis acids BBr3[5] it forms a 1:1 adduct, Br3B+PCl3. Even metal complexes such as Ni(PCl3)4 are known. This Lewis basicity is evident in one useful route to organophosphorus compounds: A Lewis base is any molecule or ion that can form a new covalent bond by donating a pair of electrons. ... In chemistry, a Lewis acid is any acid that can accept a pair of electrons and form a coordinate covalent bond, after the American chemist Gilbert Lewis. ...



PCl3 + RCl + AlCl3 → (RPCl3)+ AlCl4 An Alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... Aluminium chloride (AlCl3) is a compound of aluminium and chlorine. ...



The (RPCl3)+ product can then be decomposed with water to produce an alkylphosphonic dichloride RP(=O)Cl2.


Preparation

Phosphorus trichloride is prepared industrially by the reaction of chlorine with a refluxing solution of white phosphorus in phosphorus trichloride, with continuous removal of PCl3 as it is formed. In the laboratory it may be more convenient to use the less toxic red phosphorus[6]. General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... Diagram of typical reflux apparatus. ... This article is about the chemical element. ...



P4 + 6 Cl2 → 4 PCl3 This article is about the chemical element. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ...



Industrial production of phosphorus trichloride is controlled under the Chemical Weapons Convention, where it is listed in schedule 3 Chemical Weapons Convention Opened for signature January 13, 1993 at Paris Entered into force April 29, 1997 Conditions for entry into force Ratification by 50 states and the convening of a Preperatory Commission Parties 170 The Chemical Weapons Convention is an arms control agreement which outlaws the production, stockpiling and... Schedule 3 substances, in the sense of the Chemical Weapons Convention, are either toxic enough to be used as chemical weapons, or precursors of other listed substances. ...


Uses

Phosphorus trichloride is an important starting point for the manufacture of many industrial products containing phosphorus. World production exceeds one-third of a million tonnes[1], a part of which is oxidised to produce PCl5, POCl3 or PSCl3. These are used for the manufacture of triphenyl phosphate and tricresyl phosphate, which find application as flame retardants and plasticisers for PVC. They are also used to make insecticides such as diazinon. PCl3 is used on an industrial scale to make phosphonates, the herbicide glyphosate, triphenylphosphine for the Wittig reaction, and phosphite esters which may be used as industrial intermediates, or used in the Horner-Wadsworth-Emmons reaction, both important methods for making alkenes. It can be used to make trioctylphosphine oxide (TOPO), used as an extraction agent, although TOPO is usually made via the corresponding phosphine. A tonne (also called metric ton) is a non-SI unit of mass, accepted for use with SI, defined as: 1 tonne = 103 kg (= 106 g). ... Phosphorus Trichloride Phosphorus Pentachloride Phosphorus trichloride (PCl3) and phosphorus pentachloride (PCl5) are reactive chemicals used as chlorinating reagents in a chemical laboratory. ... Phosphorus trichloride Phosphorus pentachloride (gas phase structure) Phosphorus oxychloride[1] Phosphorus trichloride (PCl3) and phosphorus pentachloride (PCl5) are reactive chemicals used as chlorinating reagents in a chemical laboratory. ... Flame retardants are materials that inhibit or resist the spread of fire. ... Plasticizers are plastic additives, most commonly phthalates, that give plastics flexibility and durability. ... PVC may refer to the following: The chemical compound polyvinyl chloride Irregular heartbeat: premature ventricular contraction In frame relay, ATM and X.25 a permanent virtual circuit This is a disambiguation page — a navigational aid which lists other pages that might otherwise share the same title. ... Insecticide application by crop spraying An insecticide is a pesticide whose purpose is to kill or to prevent the multiplication of insects. ... Diazinon Diazinon (O,O-diethyl 0-2-isopropyl-6-methyl(pyrimidine-4-yl) phosphorothioate), a colorless to dark brown liquid, is a nonsystemic organophosphate insecticide used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. ... A herbicide is a pesticide used to kill unwanted plants. ... Glyphosate (N-(phosphonomethyl) glycine, C3H8NO5P) is a non-selective herbicide to kill weeds, especially perennials. ... Triphenylphosphine is a common chemical reagent widely used in organic synthesis. ... Georg Wittig (June 16, 1897 in Berlin (Germany) - August 26, 1987) was a german chemist who reported a method for synthesis of alkenes from aldehydes and ketones using compounds called phosphonium ylides. ... An alkene is an unsaturated hydrocarbon containing at least one carbon-carbon double bond. ...


PCl3 is also used directly as a reagent in organic synthesis. It is used to convert primary and secondary alcohols into alkyl chlorides, or carboxylic acids into acyl chlorides, although thionyl chloride generally gives better yields than PCl3[8]. A reagent is any substance used in a chemical reaction. ... Organic synthesis is the construction of organic molecules via chemical processes. ... In general usage, alcohol (from Arabic al-khwl الكحول, or al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... Alkyl halide ... Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. The salts and anions of carboxylic acids are called carboxylates generally. ... General Chemical Structure of an Acyl Chloride In organic chemistry, an acid chloride (or acyl chloride) is an organic chemical compound which is a very reactive derivative of a carboxylic acid. ... Thionyl chloride (or thionyl dichloride) is an inorganic compound with the formula S O Cl2. ...


Precautions

PCl3 is highly toxic, with a concentration of 600 ppm being lethal in just a few minutes[7]. It reacts violently with water and is highly corrosive. Wear gloves and goggles and work in a fume cupboard (hood), and use an apron and face shield with larger amounts. It is a reducing agent and should be kept away from strong oxidising agents. PPM can stand for more than one thing: Pages per minute, a measure of speed often used to market printers or photocopiers the Portable Pixmap file format the PPM compression algorithm (Prediction by partial matching) used in computer science Parts per million, a measure of concentration Portable People Meter peak... The most fundamental reactions in chemistry are the redox processes. ...


PCl3 is classified as very toxic and corrosive under EU Directive 67/548/EEC, and the risk phrases R14, R26/28, R35 and R48/20 are obligatory. For a list of biologically injurious substances, including toxins and other materials, as well as their effects, see poison. ... Corrosion is the destructive reaction of a metal with another material, e. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main source of European Union law concerning chemical safety. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ...


Suppliers/Manufacturers

References

  1. N. N. Greenwood, A. Earnshaw, Chemistry of the Elements, 2nd ed., Butterworth-Heinemann, Oxford, UK, 1997.
  2. Handbook of Chemistry and Physics, 71st edition, CRC Press, Ann Arbor, Michigan, 1990.
  3. J. March, Advanced Organic Chemistry, 4th ed., p. 723, Wiley, New York, 1992.
  4. The Merck Index, 7th edition, Merck & Co, Rahway, New Jersey, USA, 1960.
  5. R. R. Holmes, Journal of Inorganic and Nuclear Chemistry 12, 266-275 (1960).
  6. M. C. Forbes, C. A. Roswell, R. N. Maxson, Inorganic Syntheses, Vol. II, 145-7 (1946).
  7. A. D. F. Toy, The Chemistry of Phosphorus, Pergamon Press, Oxford, UK, 1973.
  8. L. G. Wade, Jr., Organic Chemistry, 6th ed., p. 477, Pearson/Prentice Hall, Upper Saddle River, New Jersey, USA, 2005.

  Results from FactBites:
 
Phosphorus - LoveToKnow 1911 (6826 words)
The crude phosphorus is purified by melting under water and then filtering through animal fl and afterwards through chamois leather, or by treating it, when molten, with chromic acid or a mixture of potassium bichromate and sulphuric acid; this causes the impurities to rise to the surface as a scum which can be skimmed off.
Phosphorus trichloride or phosphorous chloride, PC13, discovered by Gay-Lussac and Thenard in 1808, is obtained by passing a slow current of chlorine over heated red phosphorus or through a solution of ordinary phosphorus in carbon disulphide (purifying in the latter case by fractional distillation).
The phosphorus used in the British pharma copoeia is obtained from calcium phosphate, and is a waxlike non-metallic substance soluble in oils and luminous in the dark.
  More results at FactBites »

 
 

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