| Phosphorus pentachloride | |
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| IUPAC name | Phosphorus(V) chloride |
| Other names | Phosphorus pentachloride |
| Identifiers | |
| CAS number | [10026-13-8] |
| RTECS number | TB6125000 |
| SMILES | ClP(Cl)(Cl)(Cl)Cl |
| Properties | |
| Molecular formula | PCl5 |
| Molar mass | 208. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 22 g mol−1 |
| Appearance | colourless crystals |
| Density | 1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 6 g cm−3 |
| Melting point | 179–181 °C |
| Boiling point | sublimation 70-80 °C |
| Solubility in water | decomposition (exothermic) |
| Solubility in other solvents | carbon disulfide, chlorocarbons, benzene |
| Structure | |
| Coordination geometry | D3h |
| Dipole moment | 0 D |
| Hazards | |
| Main hazards | HCl source |
| R-phrases | 14-22-26-34-48/20 |
| S-phrases | 26-36/37/39-45-7/8 |
| Related compounds | |
| Related compounds | POCl3, PCl3, PF5 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Phosphorus pentachloride is the chemical compound with the formula PCl5. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. The haloalkanes (also known as halogenoalkanes or alkyl halides) are a group of Chemical compounds consisting of Alkanes such as Methane Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6 The term coordination geometry is used in a number of related fields of chemistry and solid state chemistry/physics In physics there are two kinds of dipoles ( Hellènic: di(s- = two- and pòla = pivot hinge An electric dipole is a The debye (symbol D) is a non- SI, CGS unit of electrical dipole moment. Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. It is one of the most important phosphorus chlorides, others being PCl3 and POCl3. Phosphorus trichloride (formula P[[Chlorine Cl]]3 is the most important of the three Phosphorus chlorides. Submit to get this template --> Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula 3 PCl5 finds use as a chlorinating reagent. A reagent or reactant is a substance or compound consumed during a Chemical reaction. It is a colourless, water-sensitive solid, although commercial samples can be yellowish and contaminated with hydrogen chloride. A solid' object is in the States of matter characterized by resistance to Deformation and changes of Volume.
Contents |
Structure
The structures for the phosphorus chlorides are invariably consistent with VSEPR theory. Valence shell electron pair repulsion (VSEPR theory (1957 is a model in Chemistry, which is used for predicting the shapes of individual Molecules based The structure of PCl5 depends on its environment. Gaseous and molten PCl5 is a neutral molecule with trigonal bipyramidal (D3h) symmetry. The Symmetry group of an object ( Image, signal, etc eg in 1D 2D or 3D is the group of all Isometries under which it is The hypervalent nature of this species (as well as for PCl6−, see below) can be explained with three-center four-electron bonding model. A hypervalent molecule is a Molecule that contains one or more typical elements ( group 1 2 13-18 formally bearing more than eight Electrons in their The 3-center-4-electron bond is a model used to explain bonding in Hypervalent molecules such as Phosphorus pentafluoride, Sulfur hexafluoride, the This trigonal bipyramidal structure persists in non-polar solvents, such as CS2 and CCl4. Carbon tetrachloride, also known by many other names (see Table is the Organic compound with the formula CCl4 [1]
In solutions of polar solvents, however, PCl5 undergoes "autoionization". [2] Dilute solutions dissociate according to the following equilibrium:
- PCl5
[PCl4+]Cl−
At higher concentrations, a second equilibrium becomes more important:
- 2 PCl5 [PCl4+][PCl6−]
The cation PCl4+ and the anion PCl6− are tetrahedral and octahedral, respectively. At one time, PCl5 in solution was thought to form a dimeric structure, P2Cl10, but this suggestion is not supported by Raman spectroscopic measurements. Raman spectroscopy (pronounced S— is a spectroscopic technique used in Condensed matter physics and Chemistry to study vibrational rotational and
Preparation
PCl5 is prepared by the chlorination of PCl3. Chlorination is the process of adding the element Chlorine to Water as a method of Water purification to make it fit for human consumption as This reaction was used to produce ca. 10,000,000 kg of PCl5 in 2000. [3]
- PCl3 + Cl2 PCl5 ΔH = −124 kJ/mol
PCl5 exists in equilibrium with PCl3 and chlorine, and at 180 °C the degree of dissociation is ca. Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and 40%. [3] Because of this equilibrium, samples of PCl5 often contain chlorine, which imparts a greenish colouration.
Hydrolysis
In its most characteristic reaction, PCl5 react upon contact with water to release hydrogen chloride and give phosphorus oxides. A chemical reaction is a process that always results in the interconversion of Chemical substances The substance or substances initially involved in a chemical reaction are called Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as The first hydrolysis product is phosphorus oxychloride:
- PCl5 + H2O → POCl3 + 2 HCl
In hot water, hydrolysis proceeds completely to ortho-phosphoric acid:
- PCl5 + 4 H2O → H3PO4 + 5 HCl
Other reactions
Most often PCl5 is used for chlorinations. Submit to get this template --> Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula 3 Phosphoric acid, also known as orthophosphoric acid or phosphoric(V acid, is a mineral (inorganic acid having the Chemical formula [4]
Chlorinations of organic compounds with PCl5
In synthetic chemistry, two classes of chlorination are usually of interest. Oxidative chlorinations entail the transfer of Cl2 from the reagent to the substrate. Substitutive chlorinations entail replacement of O or OH groups with chloride. PCl5 can be used for both processes.
PCl5 will convert carboxylic acids to the corresponding acyl chloride[5] as well as alcohols to alkyl chloride. Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H In Organic chemistry, an acyl chloride (or acid chloride) is an Organic compound which is a reactive derivative of a Carboxylic acid. In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon The haloalkanes (also known as halogenoalkanes or alkyl halides) are a group of Chemical compounds consisting of Alkanes such as Methane Thionyl chloride is more commonly used in the laboratory because the SO2 is more easily separated from the organic products than is POCl3. Thionyl chloride (or thionyl dichloride) is an Inorganic compound with the formula S[[Oxygen O]] Cl 2
PCl5 and PCl3 bear some resemblance to SO2Cl2, as both serve often as sources of Cl2. Sulfuryl chloride is SO2Cl2 a compound composed of Sulfur, Oxygen, and Chlorine. Again for oxidative chlorinations on the laboratory scale, SO2Cl2 is often preferred over PCl5 since the gaseous SO2 by-product is readily separated. Sulfuryl chloride is SO2Cl2 a compound composed of Sulfur, Oxygen, and Chlorine.
PCl5 reacts with a tertiary amides, such as DMF, to give dimethylchloromethyleneammonium chloride, which is called the Vilsmeier reagent, [(CH3)2NCClH]Cl. The Vilsmeier-Haack reaction (also called the Vilsmeier reaction) is the Chemical reaction of a substituted Amide ( 1) with Phosphorus oxychloride More typically, a related salt is generated from the reaction of DMF and POCl3. Such reagents are useful in the preparation of derivatives of benzaldehyde by formylation and for the conversion of C-OH groups into C-Cl groups. Benzaldehyde (C6H5CHO is a chemical compound consisting of a Benzene ring with an Aldehyde substituent [4]
In contrast to PCl3, the pentachloride replaces allylic and benzylic CH bonds and is especially renown for the conversion of C=O groups to CCl2 groups. [6]
The electrophilic character of PCl5 is highlighted by its reaction with styrene to give, after hydrolysis, phosphonic acid derivatives. In Chemistry, an electrophile (literally electron-lover) is a Reagent attracted to Electrons that participates in a chemical reaction by accepting Styrene, also known as vinyl benzene as well as many other names (see table is an Organic compound with the Chemical formula C6H5CH=CH2 Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions [7]
Chlorination of inorganic compounds
As for the reactions with organic compounds, the use of PCl5 has been superseded by SO2Cl2. The reaction of phosphorus pentoxide and PCl5 produces POCl3:[2]:
- 6 PCl5 + P4O10 → 10 POCl3
PCl5 chlorinates nitrogen dioxide:
- PCl5 + 2 NO2 → PCl3 + 2 NO2Cl
PCl5 is a precursor for lithium hexafluorophosphate, LiPF6, an electrolytes in lithium ion battery:
Arsenic and antimony pentachloride
AsCl5 and SbCl5 adopt trigonal bipyramidal structures. Phosphorus pentoxide is a Chemical compound with formula P 2 O 5 Submit to get this template --> Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula 3 Nitrogen dioxide is the Chemical compound with the formula N[[Oxygen O]]2 The nitronium ion (improperly called nitryl ion, because it is not a radical 2+ is a generally unstable Cation created by the removal of an Hexafluorophosphate is an anion with chemical formula of − As a Non-coordinating anion, it is a poor Nucleophile. An electrolyte is any substance containing free Ions that behaves as an electrically conductive medium Lithium-ion batteries (sometimes abbreviated Li-ion batteries) are a type of Rechargeable battery in which a Lithium ion moves between the Anode Lithium fluoride is a Chemical compound of Lithium and Fluorine. Lithium chloride is a Chemical compound with the formula Li[[Chlorine Cl]] The relevant bond distances are 211 (As-Cleq) 221 (As-Cleq), 227 (Sb-Cleq), and 233. 3 pm (Sb-Clax ). [8] At low temperatures, SbCl5 converts to the dimer, bioctahedral Sb2Cl10, structurally related to niobium pentachloride. Niobium(V chloride, also known as niobium pentachloride, is a yellow crystalline solid often used as a starting material in Niobium chemistry
Safety
PCl5 is a dangerous substance as it reacts violently with water and is a source of both hydrogen chloride and chlorine. Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and
See also
References
- ^ D. There are three series of binary phosphorus halides, containing Phosphorus in the Oxidation states +5 +3 and +2 E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam 1995. ISBN 0-444-89307-5.
- ^ Suter, R. W. ; Knachel, H. C. ; Petro, V. P. ; Howatson, J. H. ; S. G. Shore, S. G. ”Nature of Phosphorus(V) Chloride in Ionizing and Nonionizing Solvents” Journal of the American Chemical Society 1973, volume 95, pp 1474 - 1479; DOI: 10. 1021/ja00786a021
- ^ a b Holleman, A. F. ; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
- ^ a b Burks, Jr. , J. E. “Phosphorus(V) Chloride” in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10. 1002/047084289.
- ^ Adams, R. Roger Adams ( January 2, 1889 – July 6, 1971) was an American organic chemist. ; Jenkins, R. L. “p-Nitrobenzoyl chloride” Organic Syntheses, Collected Volume 1, p. 394 (1941).
- ^ Gross, H. ; Rieche, A. ; Höft, E. ; Beyer, E. “Dichloromethyl Methyl Ether” Organic Syntheses, Collected Volume 5, p. 365 (1973).
- ^ Schmutzler, R. ”Styrylphosphonic dichloride” Organic Syntheses, Collected Voume 5, p. 1005 (1973).
- ^ Haupt, S. ; Seppelt, K. , "Solid State Structures of AsCl5 and SbCl5", Zeitschrift für Anorganische und Allgemeine Chemie, 2002, volume 628, pages 729-734.
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