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Phosphine
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This article is about the phosphorus-containing chemical. For the class of compounds used as ligands, see metal phosphine complex. For the visual phenomenon, see phosphene. For the chemical weapon, see phosgene.
"Phosphane" redirects here. For pentavalent organophosphorus compounds, see phosphorane. For the fictional substance used in the K9 tv series, see The Korven.
Phosphine
Names
IUPAC name
Phosphane
Other names
Phosphamine
Phosphorus trihydride
Phosphorated hydrogen
Identifiers
CAS Number
7803-51-2 Y
3D model (JSmol)
Interactive image
ChEBI
CHEBI:30278 Y
ChemSpider
22814 Y
ECHA InfoCard 100.029.328
EC Number 232-260-8
Gmelin Reference
287
PubChem CID
24404
RTECS number SY7525000
UN number 2199
InChI[show]
InChI=1S/H3P/h1H3 Y
Key: XYFCBTPGUUZFHI-UHFFFAOYSA-N Y
InChI=1/H3P/h1H3
Key: XYFCBTPGUUZFHI-UHFFFAOYAP
SMILES[show]
P
Properties
Chemical formula
PH3
Molar mass 33.99758 g/mol
Appearance colorless gas
Odor faint, fish-like or garlic-like[1]
Density 1.379 g/l, gas (25 °C)
Melting point −132.8 °C (−207.0 °F; 140.3 K)
Boiling point −87.7 °C (−125.9 °F; 185.5 K)
Solubility in water
31.2 mg/100 ml (17 °C)
Solubility soluble in alcohol, ether, CS2
slightly soluble in benzene, chloroform, ethanol
Vapor pressure 41.3 atm (20°C)[1]
Refractive index (nD)
2.144
Viscosity 1.1 x 10−5 Pa s
Structure
Molecular shape
Trigonal pyramidal
Dipole moment
0.58 D
Thermochemistry
Specific
heat capacity (C)
37 J/mol K
Std molar
entropy (So298)
210 J·mol−1·K−1[2]
Std enthalpy of
formation (ΔfHo298)
5 kJ·mol−1[2]
Gibbs free energy (ΔfG˚)
13 kJ/mol
Hazards
Safety data sheet ICSC 0694
GHS pictograms
NFPA 704
4
4
2
Flash point flammable gas
Autoignition
temperature
38 °C (100 °F; 311 K) see text
Explosive limits 1.79% – 98% [1]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
3.03 mg/kg (rat, oral)
LC50 (median concentration)
11 ppm (rat, 4 hr)[3]
LCLo (lowest published)
1000 ppm (mammal, 5 min)
270 ppm (mouse, 2 hr)
100 ppm (guinea pig, 4 hr)
50 ppm (cat, 2 hr)
2500 ppm (rabbit, 20 min)
1000 ppm (human, 5 min)[3]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 0.3 ppm (0.4 mg/m3)[1]
REL (Recommended)
TWA 0.3 ppm (0.4 mg/m3) ST 1 ppm (1 mg/m3)[1]
IDLH (Immediate danger)
50 ppm[1]
Related compounds
Other cations
Ammonia
Arsine
Stibine
Bismuthine
Related compounds
Trimethylphosphine
Triphenylphosphine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is Y N ?)
Infobox references
Phosphine (IUPAC name: phosphane) is the compound with the chemical formula PH3. It is a colorless, flammable, toxic gas and pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like garlic or rotting fish, due to the presence of substituted phosphine and diphosphane (P2H4). With traces of P2H4 present, PH3 is spontaneously flammable in air, burning with a luminous flame. Phosphines are also a group of organophosphorus compounds with the formula R3P (R = organic derivative). Organophosphines are important in catalysts where they complex to various metal ions; complexes derived from a chiral phosphine can catalyze reactions to give chiral, enantioenriched products.
Contents
[hide]
1 History
2 Structure and properties
3 Preparation and occurrence
3.1 Laboratory routes
3.2 Occurrence
4 Phosphines
4.1 Primary phosphines
4.2 Secondary phosphines
4.3 Tertiary phosphines
4.4 Cyclic phosphines
5 Applications
5.1 Organophosphorus chemistry
5.2 Microelectronics
5.3 Fumigant
6 Safety
7 Toxicity
8 See also
9 References
10 Further reading
11 External links
History[edit]
Philippe Gengembre (1764-1838), a student of Lavoisier, first obtained phosphine in 1783 by heating phosphorus in an aqueous solution of potash (potassium carbonate).[4][5]
Perhaps because of its strong association with elemental phosphorus, phosphine was once regarded as a gaseous form of the element, but Lavoisier (1789) recognised it as a combination of phosphorus with hydrogen and described it as phosphure d'hydrogène (phosphide of hydrogen).[6]
In 1844, Paul Thénard, son of the French chemist Louis Jacques Thénard, used a cold trap to separate diphosphine from phosphine that had been generated from calcium phosphide, thereby demonstrating that P2H4 is responsible for spontaneous flammability associated with PH3, and also for the characteristic orange/brown color that can form on surfaces, which is a polymerisation product.[7] He considered diphosphine’s formula to be PH2, and thus an intermediate between elemental phosphorus, the higher polymers, and phosphine. Calcium phosphide (nominally Ca3P2) produces more P2H4 than other phosphides because of the preponderance of P-P bonds in the starting material.
The name "phosphine" first appeared in combined form in 1857.[8] The gas PH3 was named "phosphine" by 1865 (or earlier).[9]
Structure and properties[edit]
PH3 is a trigonal pyramidal molecule with C3v molecular symmetry. The length of the P-H bond is 1.42 Å, the H-P-H bond angles are 93.5°. The dipole moment is 0.58 D, which increases with substitution of methyl groups in the series: CH3PH2, 1.10 D; (CH3)2PH, 1.23 D; (CH3)3P, 1.19 D. In contrast, the dipole moments of amines decrease with substitution, starting with ammonia, which has a dipole moment of 1.47 D. The low dipole moment and almost orthogonal bond angles lead to the conclusion that in PH3 the P-H bonds are almost entirely pσ(P) – sσ(H) and phosphorus 3s orbital contributes little to the bonding between phosphorus and hydrogen in this molecule. For this reason, the lone pair on phosphorus may be regarded as predominantly formed by the 3s orbital of phosphorus. The upfield chemical shift of the phosphorus atom in the 31P NMR spectrum accords with the conclusion that the lone pair electrons occupy the 3s orbital (Fluck, 1973). This electronic structure leads to a lack of nucleophilicity and an ability to form only weak hydrogen bonds.[10]
The aqueous solubility of PH3 is slight; 0.22 mL of gas dissolve in 1 mL of water. Phosphine dissolves more readily in non-polar solvents than in water because of the non-polar P-H bonds. It is technically amphoteric in water, but acid and base activity is poor. Proton exchange proceeds via a phosphonium (PH4+) ion in acidic solutions and via PH2− at high pH, with equilibrium constants Kb = 4 × 10−28 and Kz = 41.6 × 10−29.
Phosphine burns producing a dense white cloud of phosphoric acid:
PH3 + 2 O2 → H3PO4
Preparation and occurrence[edit]
Phosphine may be prepared in a variety of ways.[11] Industrially it can be made by the reaction of white phosphorus with sodium or potassium hydroxide, producing sodium or potassium hypophosphite as a by-product.
3 KOH + P4 + 3 H2O → 3 KH2PO2 + PH3
Alternatively the acid-catalyzed disproportioning of white phosphorus yields phosphoric acid and phosphine. Both routes have industrial significance; the acid route is preferred method if further reaction of the phosphine to substituted phosphines is needed. The acid route requires purification and pressurizing. It can also be made (as described above) by the hydrolysis of a metal phosphide, such as aluminium phosphide or calcium phosphide. Pure samples of phosphine, free from P2H4, may be prepared using the action of potassium hydroxide on phosphonium iodide (PH4I).
Laboratory routes[edit]
It is prepared in the laboratory by disproportionation of phosphorous acid[12]
4 H3PO3 → PH3 + 3 H3PO4
Phosphine evolution occurs around 200 °C. Alternative methods involve the hydrolysis of aluminium phosphide, calcium phosphide, and tris(trimethylsilyl)phosphine.
Occurrence[edit]
Phosphine is a constituent of the atmosphere at very low and highly variable concentrations.[13] It may contribute significantly to the global phosphorus biochemical cycle. The most likely source is reduction of phosphate in decaying organic matter, possibly via partial reductions and disproportionations, since environmental systems do not have known reducing agents of sufficient strength to directly convert phosphate to phosphine.[14]
Phosphines[edit]
See also: metal phosphine complex
Organophosphines are compounds with the formula PRnH3−n. These compounds are often classified according to the value of n: primary phosphines (n = 1), secondary phosphines (n = 2), tertiary phosphines (n = 3). All adopt pyramidal structures. Their reactivity is also similar - they can be oxidized to the phosphorus(V) level, they can be protonated and alkylated at phosphorus to give phosphonium salts, and, for primary and secondary derivatives, they can be deprotonated by strong bases to give organophosphide derivatives.
Primary phosphines[edit]
Primary phosphines are typically prepared by alkylation of phosphine. Simple alkyl derivatives such as methylphosphine (CH3PH2) are prepared by alkylation of alkali metal derivatives MPH2 (M = Li, Na, K). Another synthetic route involves treatment of the corresponding chlorophosphines with hydride reagents. For example, reduction of dichlorophenylphosphine with lithium aluminium hydride affords phenylphosphine (PhPH2).
Secondary phosphines[edit]
Secondary phosphines are prepared analogously to the primary phosphines. They are also obtained by alkali-metal reductive cleavage of triarylphosphines followed by hydrolysis of the resulting phosphide salt. The latter route is employed to prepare diphenylphosphine (Ph2PH). Diorganophosphinic acids, R2P(O)OH, can also be reduced with diisobutylaluminium hydride. Secondary phosphines are typically protic in character. When however modified with suitable substituents as in certain (rare) diazaphospholenes (scheme 3) the polarity of the P-H bond can be inverted (see: umpolung) and the resulting phosphine hydride can reduce a carbonyl group as in the example of benzophenone in yet another way.[15]
Tertiary phosphines[edit]
Tertiary phosphines are generally obtained by treatment of phosphorus trichloride or triphenylphosphite with organolithium reagents or Grignard reagents. Tertiary phosphines of the type PRR'R" are chiral and optically stable.
Cyclic phosphines[edit]
Secondary and tertiary phosphines occur in cyclic forms. Three-membered rings are phosphiranes (unsaturated: phosphirenes), five-membered rings are phospholanes (unsaturated: phosphole), and six-membered rings are phosphinanes.
Applications[edit]
Organophosphorus chemistry[edit]
Phosphine is mainly consumed as an intermediate in organophosphorus chemistry. In an illustrative reaction, formaldehyde adds in the presence of hydrogen chloride to give tetrakis(hydroxymethyl)phosphonium chloride, which is used in textiles.
Microelectronics[edit]
Small amounts of phosphine are used as a dopant in the semiconductor industry, and a precursor for the deposition of compound semiconductors.[16]
Fumigant[edit]
For farm use, pellets of aluminium phosphide, calcium phosphide, or zinc phosphide release phosphine upon contact with atmospheric water or rodents' stomach acid. These pellets also contain agents to reduce the potential for ignition or explosion of the released phosphine. A more recent alternative is the use of phosphine gas itself which requires dilution with either CO2 or N2 or even air to bring it below the flammability point. Use of the gas avoids the issues related with the solid residues left by metal phosphide and results in faster, more efficient control of the target pests.
Because the previously popular fumigant methyl bromide has been phased out in some countries under the Montreal Protocol, phosphine is the only widely used, cost-effective, rapidly acting fumigant that does not leave residues on the stored product. Pests with high levels of resistance toward phosphine have become common in Asia, Australia and Brazil. High level resistance is also likely to occur in other regions, but has not been as closely monitored. Genetic variants that contribute to high level resistance to phosphine have been identified in the dihydrolipoamide dehydrogenase gene.[17] Identification of this gene now allows rapid molecular identification of resistant insects.
Safety[edit]
Further information: Aluminium phosphide poisoning
Phosphine gas is denser than air and hence may collect in low-lying areas. It can form explosive mixtures with air and also self-ignite.
Phosphine can be absorbed into the body by inhalation. Direct contact with phosphine liquid – although unlikely to occur – may cause frostbite, like other cryogenic liquids. The main target organ of phosphine gas is the respiratory tract.[18] According to the 2009 U.S. National Institute for Occupational Safety and Health (NIOSH) pocket guide, and U.S. Occupational Safety and Health Administration (OSHA) regulation, the 8 hour average respiratory exposure should not exceed 0.3 ppm. NIOSH recommends that the short term respiratory exposure to phosphine gas should not exceed 1 ppm. The Immediately Dangerous to Life or Health level is 50 ppm. Overexposure to phosphine gas causes nausea, vomiting, abdominal pain, diarrhea, thirst, chest tightness, dyspnea (breathing difficulty), muscle pain, chills, stupor or syncope, and pulmonary edema.[19][20] Phosphine has been reported to have the odor of decaying fish or garlic at concentrations below 0.3 ppm. The smell is normally restricted to laboratory areas or phosphine processing since the smell comes from the way the phosphine is extracted from the environment. However, it may occur elsewhere, such as in industrial waste landfills. Exposure to higher concentrations may cause olfactory fatigue.[21]
Toxicity[edit]
Deaths have resulted from accidental exposure to fumigation materials containing aluminum phosphide or phosphine.[22][23][24][25][26] Phosphine gas attacks the central nervous system, much as military nerve gases do. It can be absorbed either by inhalation or through the skin.[24][27]
See also[edit]
Diphosphane, H2PPH2, simplified to H4P2
Diphosphines, R2PPR2, R2P(CH2)nPR2
Diphosphene, HP=PH
Diphosphenes, R-P=P-R'
Phosphine oxide, R3P=O
Phosphorane, PR5, R3P=CR2
Phosphinite, P(OR)R2
Phosphonite, P(OR)2R
Phosphite, P(OR)3
Phosphinate, R2P(RO)O
Phosphonate, RP(RO)2O
Phosphate, P(RO)3O
References[edit]
^ Jump up to: a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0505". National Institute for Occupational Safety and Health (NIOSH).
^ Jump up to: a b Zumdahl, Steven S. (2009). Chemical Principles 6th Ed. Houghton Mifflin Company. p. A22. ISBN 0-618-94690-X.
^ Jump up to: a b "Phosphine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
Jump up ^ Gengembre (1783) "Mémoire sur un nouveau gas obtenu, par l'action des substances alkalines, sur le phosphore de Kunckel" (Memoir on a new gas obtained by the action of alkaline substances on Kunckel's phosphorus), Mémoires de mathématique et de physique, 10 : 651-658.
Jump up ^ For further information about the early history of phosphine, see:
The Encyclopædia Britannica (1911 edition), vol. 21, p. 480: Phosphorus: Phosphine.
Thomas Thomson, A System of Chemistry, 6th ed. (London, England: Baldwin, Cradock, and Joy, 1820), vol. 1, p. 272.
Jump up ^ Note:
On p. 222 of his Traité élémentaire de chimie, vol. 1, (Paris, France: Cuchet, 1789), Lavoisier calls the compound of phosphorus and hydrogen "phosphure d'hydrogène" (hydrogen phosphide). However, on p. 216, he calls the compound of hydrogen and phosphorus "Combinaison inconnue." (unknown combination), yet in a footnote, he says about the reactions of hydrogen with sulfur and with phosphorus: "Ces combinaisons ont lieu dans l'état de gaz & il en résulte du gaz hydrogène sulfurisé & phosphorisé." (These combinations occur in the gaseous state, and there results from them sulfurized and phosphorized hydrogen gas.)
In Robert Kerr's 1790 English translation of Lavoisier's Traité élémentaire de chimie … — namely, Lavoisier with Robert Kerr, trans., Elements of Chemistry … (Edinburgh, Scotland: William Creech, 1790) — Kerr translates Lavoisier's "phosphure d'hydrogène" as "phosphuret of hydrogen" (p. 204), and whereas Lavoisier — on p. 216 of his Traité élémentaire de chimie … — gave no name to the combination of hydrogen and phosphorus, Kerr calls it "hydruret of phosphorus, or phosphuret of hydrogen" (p. 198). Lavoisier's note about this compound — "Combinaison inconnue." — is translated: "Hitherto unknown." Lavoisier's footnote is translated as: "These combinations take place in the state of gas, and form, respectively, sulphurated and phosphorated oxygen gas." The word "oxygen" in the translation is an error because the original text clearly reads "hydrogène" (hydrogen). (The error was corrected in subsequent editions.)
Jump up ^ Paul Thénard (1844) "Mémoire sur les combinaisons du phosphore avec l'hydrogène" (Memoir on the compounds of phosphorus with hydrogen), Comptes rendus, 18 : 652-655.
Jump up ^ In 1857, August Wilhelm von Hofmann announced the synthesis of organic compounds containing phosphorus, which he named "trimethylphosphine" and "triethylphosphine", in analogy with "amine" (organo-nitrogen compounds), "arsine" (organo-arsenic compounds), and "stibine" (organo-antimony compounds). See: A.W. Hofmann and Auguste Cahours (1857) "Researches on the phosphorus bases," Proceedings of the Royal Society of London, 8 : 523-527. From page 524: "The bases Me3P and E3P, the products of this reaction, which we propose to call respectively trimethylphosphine and triethylphosphine, … "
Jump up ^ William Odling, A Course of Practical Chemistry Arranged for the Use of Medical Students, 2nd ed. (London, England: Longmans, Green, and Co., 1865), pp. 227, 230.
Jump up ^ Sennikov, P. G. (1994). "Weak H-Bonding by Second-Row (PH3, H2S) and Third-Row (AsH3, H2Se) Hydrides". Journal of Physical Chemistry. 98 (19): 4973–4981. doi:10.1021/j100070a006.
Jump up ^ Toy, A. D. F. (1973). The Chemistry of Phosphorus. Oxford, UK: Pergamon Press.
Jump up ^ Gokhale, S. D.; Jolly, W. L., "Phosphine", Inorganic Syntheses 1967, volume 9, pp. 56–58. doi:10.1002/9780470132401.ch17
Jump up ^ Gassmann, G.; van Beusekom, J. E. E.; Glindemann, D. (1996). "Offshore atmospheric phosphine". Naturwissenschaften. 83 (3): 129–131. Bibcode:1996NW.....83..129G. doi:10.1007/BF01142178. CS1 maint: Multiple names: authors list (link)
Jump up ^ Roels, J.; Verstraete, W. (2001). "Biological formation of volatile phosphorus compounds, a review paper". Bioresource Technology. 79 (3): 243–250. doi:10.1016/S0960-8524(01)00032-3. PMID 11499578.
Jump up ^ Burck, S.; Gudat, D.; Nieger, M.; Du Mont, W.-W. (2006). "P-Hydrogen-Substituted 1,3,2-Diazaphospholenes: Molecular Hydrides". Journal of the American Chemical Society. 128 (12): 3946–3955. doi:10.1021/ja057827j.
Jump up ^ Bettermann, G.; Krause, W.; Riess, G.; Hofmann, T. (2002). "Phosphorus Compounds, Inorganic". Ullmann's Encyclopedia of Industrial Chemistry. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_527. ISBN 3527306730.
Jump up ^ Schlipalius, D. I., Valmas, N., Tuck, A. G., Jagadeesan, R., Ma, L., Kaur, R. et al. (2012). "A Core Metabolic Enzyme Mediates Resistance to Phosphine Gas". Science. 338: 807–810. Bibcode:2012Sci...338..807S. doi:10.1126/science.1224951. PMID 23139334. CS1 maint: Uses authors parameter (link)
Jump up ^ "NIOSH Emergency Response Card". CDC. Retrieved 2010-04-06.
Jump up ^ "NIOSH pocket guide". CDC. 2009-02-03. Retrieved 2010-04-06.
Jump up ^ "WHO (Data Sheets on Pesticides-No. 46): Phosphine". Inchem.org. Retrieved 2010-04-06.
Jump up ^ "NIOSH Alert: Preventing Phosphine Poisoning and Explosions during Fumigation". CDC. 1995-07-10. Retrieved 2010-04-06.
Jump up ^ [1]
Jump up ^ [2]
^ Jump up to: a b "Two toddlers die after Jerusalem home sprayed for pests". Haaretz. 2014-01-22. Retrieved 2014-01-23.
Jump up ^ "Pesticide blamed in 8-month-old's death in Fort McMurray". CBC News. 2015-02-23. Retrieved 2015-02-23.
Jump up ^ http://www.cbc.ca/news/deaths-of-quebec-women-in-thailand-may-have-been-caused-by-pesticide-1.2569434. Missing or empty |title= (help)
Jump up ^ "4 children killed after pesticide released toxic gas underneath their home, police say". Washington Post. Retrieved 6 January 2017.
Further reading[edit]
Fluck, E. (1973). "The Chemistry of Phosphine". Topics in Current Chemistry. Fortschritte der Chemischen Forschung. 35: 1–64. doi:10.1007/BFb0051358. ISBN 3-540-06080-4.
WHO (World Health Organisation) (1988). Phosphine and Selected Metal Phosphides. Environmental Health Criteria. 73. Geneva: Joint sponsorship of UNEP, ILO and WHO.
External links[edit]
International Chemical Safety Card 0694
CDC - Phosphine - NIOSH Workplace Safety and Health Topic
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e
Phosphorus compounds
PBr3
PBr5
PCl3
PCl5
PF3
PF5
PI3
InP
PH3
PN
P3N5
P2O3
P2O4
P2O5
P4S3
P4S10
AlP
Ca3P2
Zn3P2
CuP2
HfP
FeP
Fe3P
BP
YP
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Molecules detected in outer space
Molecules
Diatomic
Aluminium monochloride
Aluminium monofluoride
Aluminium monoxide
Argonium
Carbon monophosphide
Carbon monosulfide
Carbon monoxide
Carborundum
Cyanogen radical
Diatomic carbon
Fluoromethylidynium
Hydrogen chloride
Hydrogen fluoride
Hydrogen (molecular)
Hydroxyl radical
Iron(II) oxide
Magnesium monohydride cation
Methylidyne radical
Nitric oxide
Nitrogen (molecular)
Nitrogen monohydride
Nitrogen sulfide
Oxygen (molecular)
Phosphorus monoxide
Phosphorus mononitride
Potassium chloride
Silicon carbide
Silicon mononitride
Silicon monoxide
Silicon monosulfide
Sodium chloride
Sodium iodide
Sulfur monohydride
Sulfur monoxide
Titanium oxide

Triatomic
Aluminium hydroxide
Aluminium isocyanide
Amino radical
Carbon dioxide
Carbonyl sulfide
CCP radical
Chloronium
Diazenylium
Dicarbon monoxide
Disilicon carbide
Ethynyl radical
Formyl radical
Hydrogen cyanide (HCN)
Hydrogen isocyanide (HNC)
Hydrogen sulfide
Hydroperoxyl
Iron cyanide
Isoformyl
Magnesium cyanide
Magnesium isocyanide
Methylene radical
N2H+
Nitrous oxide
Nitroxyl
Ozone
Phosphaethyne
Potassium cyanide
Protonated molecular hydrogen
Sodium cyanide
Sodium hydroxide
Silicon carbonitride
c-Silicon dicarbide
Silicon naphthalocyanine
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Thioformyl
Thioxoethenylidene
Titanium dioxide
Tricarbon
Water
Four
atoms
Acetylene
Ammonia
Cyanic acid
Cyanoethynyl
Cyclopropynylidyne
Formaldehyde
Fulminic acid
HCCN
Hydrogen peroxide
Hydromagnesium isocyanide
Isocyanic acid
Isothiocyanic acid
Ketenyl
Methylene amidogen
Methyl radical
Propynylidyne
Protonated carbon dioxide
Protonated hydrogen cyanide
Silicon tricarbide
Thioformaldehyde
Tricarbon monoxide
Tricarbon sulfide
Thiocyanic acid
Five
atoms
Ammonium ion
Butadiynyl
Carbodiimide
Cyanamide
Cyanoacetylene
Cyanoformaldehyde
Cyanomethyl
Cyclopropenylidene
Formic acid
Isocyanoacetylene
Ketene
Methane
Methoxy radical
Methylenimine
Propadienylidene
Protonated formaldehyde
Protonated formaldehyde
Silane
Silicon-carbide cluster
Six
atoms
Acetonitrile
Cyanobutadiynyl radical
E-Cyanomethanimine
Cyclopropenone
Diacetylene
Ethylene
Formamide
HC4N
Ketenimine
Methanethiol
Methanol
Methyl isocyanide
Pentynylidyne
Propynal
Protonated cyanoacetylene
Seven
atoms
Acetaldehyde
Acrylonitrile
Vinyl cyanide
Cyanodiacetylene
Ethylene oxide
Hexatriynyl radical
Methylacetylene
Methylamine
Methyl isocyanate
Vinyl alcohol
Eight
atoms
Acetic acid
Aminoacetonitrile
Cyanoallene
Ethanimine
Glycolaldehyde
Heptatrienyl radical
Hexapentaenylidene
Methylcyanoacetylene
Methyl formate
Propenal
Nine
atoms
Acetamide
Cyanohexatriyne
Cyanotriacetylene
Dimethyl ether
Ethanol
Methyldiacetylene
Octatetraynyl radical
Propene
Propionitrile
Ten
atoms
or more
Acetone
Benzene
Benzonitrile
Buckminsterfullerene (C60 fullerene, buckyball)
C70 fullerene
Cyanodecapentayne
Cyanopentaacetylene
Cyanotetra-acetylene
Ethylene glycol
Ethyl formate
Methyl acetate
Methyl-cyano-diacetylene
Methyltriacetylene
Propanal
n-Propyl cyanide
Pyrimidine
Deuterated
molecules
Ammonia
Ammonium ion
Formaldehyde
Formyl radical
Heavy water
Hydrogen cyanide
Hydrogen deuteride
Hydrogen isocyanide
Methylacetylene
N2D+
Trihydrogen cation
Unconfirmed
Anthracene
Dihydroxyacetone
Ethyl methyl ether
Glycine
Graphene
H2NCO+
Linear C5
Naphthalene cation
Phosphine
Pyrene
Silylidine
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Binary compounds of hydrogen
Alkali metal hydrides
LiH
NaH
KH
RbH
CsH

Lithium hydride, LiH
ionic metal hydride

Beryllium hydride
Left (gas phase): BeH2
covalent metal hydride
Right: (BeH2)n (solid phase)
polymeric metal hydride

Borane and diborane
Left: BH3 (special conditions), covalent metalloid hydride
Right: B2H6 (standard conditions), dimeric metalloid hydride

Methane, CH4
covalent nonmetal hydride

Ammonia, NH3
covalent nonmetal hydride

Water, H2O
covalent nonmetal hydride

Hydrogen fluoride, HF
covalent nonmetal hydride
Alkaline earth hydrides
Monohydrides
BeH
MgH
CaH
SrH
BaH
BeH2
MgH2
CaH2
SrH2
BaH2
Group 13 hydrides
Boranes
BH3
B2H6
B2H2
B2H4
Alanes
AlH3
Al2H6
Gallanes
GaH3
Ga2H6
Indiganes
InH3
In2H6
Thallanes
TlH3
Tl2H6
B2H2
B2H4
B4H10
B5H9
B5H11
B6H10
B6H12
B10H14
B18H22
Group 14 hydrides
Linear alkanes
CH4
C2H6
C3H8
C4H10
C5H12
C6H14
C7H16
C8H18
C9H20
C10H22
more...
Linear alkenes
C2H4
C3H6
C4H8
C5H10
C6H12
C7H14
C8H16
C9H18
C10H20
more...
Linear alkynes
C2H2
C3H4
C4H6
C5H8
C6H10
C7H12
C8H14
C9H16
C10H18
more...
Silanes
SiH4
Si2H6
Si3H8
Si4H10
Si5H12
Si6H14
Si7H16
Si8H18
Si9H20
Si10H22
more...
Silenes
Si2H4
Silynes
Si2H2
Germanes
GeH4
Ge2H6
Ge3H8
Ge4H10
Ge5H12
Stannanes
SnH4
Sn2H6
Plumbanes
PbH4
CH
CH2
CH3
C2H
Cycloalkanes
Cycloalkenes
Annulenes
Many more
Pnictogen hydrides
Azanes
NH3
N2H4
N3H5
N4H6
N5H7
N6H8
N7H9
N8H10
N9H11
N10H12
more...
Azenes
N2H2
N3H3
N4H4
Phosphanes
PH3
P2H4
P3H5
P4H6
P5H7
P6H8
P7H9
P8H10
P9H11
P10H12
more...
Phosphenes
P2H2
P3H3
P4H4
Arsanes
AsH3
As2H4
Stibanes
SbH3
Bismuthanes
BiH3
HN3
NH
radical
Hydrogen chalcogenides
Polyoxidanes
H2O
H2O2
H2O3
H2O4
H2O5
H2O6
H2O7
H2O8
H2O9
H2O10
more...
Polysulfanes
H2S
H2S2
H2S3
H2S4
H2S5
H2S6
H2S7
H2S8
H2S9
H2S10
more...
Selanes
H2Se
H2Se2
Tellanes
H2Te
H2Te2
Polanes
PoH2
HO
HO2
HO3
H2O+–O–
H2S=S
(HS)2S+–S–
HS
HDO
D2O
T2O
Hydrogen halides
HF
HCl
HBr
HI
HAt
Transition metal hydrides
ScH2
YH2
YH3
TiH2
ZrH2
HfH2
VH
VH2
NbH
NbH2
TaH
CrH
CrH2
CrHx
NiH
PdHx (x < 1)
FeH
FeH2
FeH5
CuH
ZnH2
CdH2
HgH2
Lanthanide hydrides
LaH2
LaH3
CeH2
CeH3
PrH2
PrH3
NdH2
NdH3
SmH2
SmH3
EuH2
GdH2
GdH3
TbH2
TbH3
DyH2
DyH3
HoH2
HoH3
ErH2
ErH3
TmH2
TmH3
YbH2
YbH2.5
LuH2
LuH3
Actinide hydrides
AcH2
ThH2
Th4H15
PaH3
UH3
NpH2
NpH3
PuH2
PuH3
AmH2
AmH3
CmH2
Authority control
NDL: 00576134
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text:
Ouzo
From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Anise-flavored liquor
An ouzo bottle
Ouzo (Greek: ούζο, IPA: [ˈuzo]) is a dry anise-flavoured aperitif that is widely consumed in Greece, Cyprus, Lebanon and Israel. Its taste is similar to other anise liquors like rakı, pastis and sambuca.
Contents
1 History
2 Name
3 Preparation
4 Aperitif drink
5 Cocktails
6 Appearance
7 Drinks with a similar flavour
8 In popular culture
8.1 In fiction
8.2 In film
8.3 In television
8.4 In song lyrics
9 See also
10 References
11 External links
History[edit]
Ouzo has its roots in tsipouro, which is said to have been the work of a group of 14th-century monks on Mount Athos. One version of it was flavoured with anise. This version eventually came to be called ouzo.[1][page needed]
Modern ouzo distillation largely took off in the beginning of the 19th century following Greek independence. The first ouzo distillery was founded in Tyrnavos in 1856 by Nikolaos Katsaros, giving birth to the famous ouzo Tyrnavou. When absinthe fell into disfavour in the early 20th century, ouzo was one of the products whose popularity rose to fill the gap; it was once called "a substitute for absinthe without the wormwood".[2] In 1932, ouzo producers developed a method of distillation using copper stills that is now the standard method of production. One of the largest producers of ouzo today is Varvayanis (Βαρβαγιάννης),[citation needed] located in the town of Plomari in the southeast portion of the island of Lesbos, while in the same town Pitsiladi (Πιτσιλαδή), a variety of high-quality ouzo, is also distilled.
Ouzo is usually mixed with water, becoming cloudy white, sometimes with a faint blue tinge, and served with ice cubes in a small glass. Ouzo can also be drunk straight from a shot glass.
Ouzo is often served with a small plate of a variety of appetizers called mezes, usually small fresh fish, fries, olives and feta cheese. Ouzo can be described to have a similar taste to absinthe which is liquorice-like, but smoother.
On October 25, 2006, Greece won the right to label ouzo as an exclusively Greek product.[3] The European Union now recognizes ouzo, as well as the Greek drinks tsipouro and tsikoudia, as products with a Protected Designation of Origin, which prohibits European makers other than Greece and Cyprus from using the name.
There is an ouzo museum[4] in Plomari, Lesvos.
Name[edit]
The origin of the name "ouzo" is disputed. A popular derivation is from the Italian "uso Massalia"—for use in Marseille—stamped on selected silkworm cocoons exported from Tyrnavos in the 19th century. According to anecdote, this designation came to stand for "superior quality", which the spirit distilled as ouzo was thought to possess.[5]
Oldest Ouzo Distillery
During a visit to Thessaly in 1896, the late professor Alexander Philadelpheus delivered to us valuable information on the origins of the word "ouzo", which has come to replace the word "tsipouro". According to the professor, tsipouro gradually became ouzo after the following event: Thessaly exported fine cocoons to Marseilles during the 19th century, and in order to distinguish the product, outgoing crates would be stamped with the words "uso Massalia"—Italian for "to be used in Marseille". One day, the Ottoman Greek consulate physician, named Anastas (Anastasios) Bey, happened to be visiting the town of Tyrnavos and was asked to sample the local tsipouro. Upon tasting the drink, the physician immediately exclaimed: "This is uso Massalia, my friends"—referring to its high quality. The term subsequently spread by word of mouth, until tsipouro gradually became known as ouzo.
—The Times of Thessaly, 1959
However, the major Greek dictionaries derive it from the Turkish word üzüm 'grape'.[6][7][8]
Preparation[edit]
A bottle of ouzo
Ouzo production begins with distillation in copper stills of 96% alcohol by volume (ABV) rectified spirit. Anise is added, sometimes with other flavorings such as star anise, fennel, mastic, cardamom, coriander, cloves, and cinnamon. The flavoring ingredients are often closely guarded company "recipes", and distinguish one ouzo from another.[9] The result is a flavored alcoholic solution known as flavored ethyl alcohol, or more commonly as ouzo yeast—μαγιά ούζου in Greek—the term for "yeast" being used by Greeks metaphorically to denote that it serves as the starting point for ouzo production.
The ouzo yeast is then distilled. After several hours of distillation, a flavored distillate of approximately 80 ABV (% Alcohol By Volume) is produced. The spirit at the beginning of the distillation (heads) and end (tails) is usually removed to avoid light and heavy alcohols and aromatics. The heads and tails are usually mixed and distilled again. The product of this second distillation can be used to produce a different quality ouzo.
This technique of double-distillation is used by some distillers to differentiate their products.
Makers of high-quality "100% from distillation" ouzo proceed at this stage with water dilution, bringing the ouzo to its final ABV. But most producers combine the "ouzo yeast" with less expensive ethyl alcohol flavored with 0.05 percent natural anethole, before water dilution. Greek law dictates that in this case the ouzo yeast cannot be less than 20 percent of the final product.
Sugar may be added before water dilution, which is done mostly with ouzo from Southern Greece.
The final ABV is usually between 37.5 and 50 percent; the minimum allowed is 37.5 percent.[10]
Ouzo production itself does not include fermentation.
Aperitif drink[edit]
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In modern Greece, ouzeries (the suffix -erie is imported from French) can be found in nearly all cities, towns, and villages. These cafe-like establishments serve ouzo with mezedes—appetizers such as octopus, salad, sardines, calamari, fried zucchini, and clams, among others. It is traditionally slowly sipped (usually mixed with water or ice) together with mezedes shared with others over a period of several hours in the early evening.
In other countries it is tradition to have ouzo in authentic Greek restaurants as an aperitif, served in a shot glass and deeply chilled before the meal is started. No water or ice is added but the drink is served very cold, enough to make some crystals form in the drink as it is served.
Ouzo can colloquially be referred to as a particularly strong drink, the cause of this being its sugar content. Sugar delays ethanol absorption in the stomach, and may thus mislead the drinker into thinking that they can drink more as they do not feel tipsy early on. Then the cumulative effect of ethanol appears and the drinker becomes inebriated rather quickly. This is why it is generally considered poor form to drink ouzo "dry hammer" ("ξεροσφύρι", xerosfýri, an idiomatic expression that means "drinking alcohol without eating anything") in Greece. The presence of food, especially fats or oils, in the upper digestive system prolongs the absorption of ethanol and ameliorates alcohol intoxication.
Cocktails[edit]
Ouzo is not used in many mainstream cocktail drinks, although in Cyprus it does form the basis of a cocktail called an Ouzini.[11]
Appearance[edit]
Main article: Ouzo effect
Ouzo is a clear liquid. However, when water or ice is added, ouzo turns a milky-white colour. This is because anethole, the essential oil of anise, is completely soluble in alcohol at approximately 38% ABV and above, but not in water. Diluting the spirit causes it to separate creating an emulsion, whose fine droplets scatter the light. This process is called louching, and is also found while preparing absinthe.
Drinks with a similar flavour[edit]
See also: List of liqueurs § Anise-flavored liqueurs
Similar aperitifs include oghi (from Armenia), mastika from Bulgaria and Macedonia, rakı from Turkey, pastis (France), and arak (from the Levant). Its aniseed flavour is also similar to the anise-flavoured liqueurs of sambuca (Italy) and anís (Spain) and the stronger spirits of absinthe (France and Switzerland). Aguardiente (Colombia), made from sugar cane, is also similar. The Italian drink Pallini Mistra, named after the Greek city of Mystras in the Peloponnese is a version of ouzo made in Rome that closely resembles Greek and Cypriot ouzo.
In popular culture[edit]
In fiction[edit]
In Jack Kerouac's autobiographical novel On the Road (1957), the following is said about a character who is thought to be the American author William S. Burroughs: "In Athens he looked up from his ouzo at what he called the ugliest people in the world."[12]
In Colonel Sun by Kingsley Amis, the first James Bond continuation novel published in 1968, shortly after Ian Fleming's death, James Bond is on a mission in Greece. In one of his exchanges with a local girl, the British secret agent has the chance to admit, over a glass of ouzo, that he knows ouzo much better than he knows Greece.[13]
In Ouroboros Ouzo, a 2014 short story by the British writer Jonathan L. Howard, necromancer Johannes Cabal visits Greece to drink Ouroboros ouzo and take a look into the future.
In In Search of Sixpence, a 2016 novel by Michael Paraskos, the lead characters, Geroud and Andrea Waites, drink ouzo cocktails outside St Nicholas Cathedral in Famagusta on the island of Cyprus.
In For Your Eyes Only produced by Eon Productions, and the fifth to star Roger Moore as the fictional MI6 agent James Bond. It marked the directorial debut of John Glen, who had worked as editor and second unit director in three other Bond films. At the casino, Bond meets Kristatos and orders a ouzo before asking how to meet Columbo, not knowing that Columbo's men are secretly recording their conversation.
In film[edit]
In the 1960 Greek film Never on Sunday by Jules Dassin, Homer (an American tourist played by Dassin) gets initiated into the carefree world of song and dance after having a few glasses of ouzo at a Pireaus taverna. The glasses get smashed right after use.
In the 1973 American film 40 Carats, Liv Ullmann as Ann Stanley who is on vacation in Greece and young Edward Albert as Peter Latham break the ice over a glass of ouzo and start a romantic relationship.
In the 1991 American film Doc Hollywood, ouzo is the "cocktail" that the three ladies of the "Welcoming Committee"—Miss Violet, Miss Lillian and Miss Mattie—offered Dr. Ben Stone (Michael J. Fox) upon his first night in Grady, SC. It is also the "Greek Death" that Stone offered Lou after running back to her house after dinner at the mayor's house that evening.
In the 2002 American film My Big Fat Greek Wedding by Joel Zwick, ouzo is served to the flabbergasted American in-laws during their first meeting with the bride's huge Greek family.
In the 2014 film The Water Diviner, Russell Crowe shares a slug from a bottle of captured Ouzo from a Greek Partisan with a Turkish (Nationalist) Major and asks "Raki?" to which the Turkish Major replies "Ouzo. Same Mother".
In television[edit]
In episode 14, season 3 of the TV series M*A*S*H, a Greek Colonel thanks the 4077th by giving them food and drink for an Easter celebration. This includes a figurative "bathtub full" of ouzo, which Colonel Blake proceeds to "swim" in.
In season 2, episode 2 of the TV series Bottom, Eddie and Richie make a cocktail of pernod, ouzo, marmalade and salt.
In Season 5 Episode 16 Gilmore Girls , Richard Gilmore says: But we found this charming little taverna – Dionysus. The view was spectacular, and the Ouzo certainly lived up to its name.
In song lyrics[edit]
In 1977, Haris Alexiou recorded the song "Ouzo otan pieis" (When you drink ouzo) in her LP 24 Songs.[14] The song is an adaptation of a 1934 song entitled "When you have dope", which was censored because of its drug related content. The adapted song was highly successful and has been translated in French, German, and Spanish.[15]
Schnapps, chianti, porter and ouzo
Pernod, vodka, sambuca—I love you so
Deportee
"The Deportees Club" (1984) by English musician Elvis Costello
I've got a belly full of ouzo
And a head full of hurt
"Mudride" (1988) by American band Mudhoney
I took you down on ouzo
And now I think I'd rather see you dead
"The Band" (2002) by the Swedish band Mando Diao
See also[edit]
Liquor portal
Drink portal
Greek food products
Cuisine of Greece
References[edit]
Jump up ^ Epikouria Magazine, Spring/Summer 2007
Jump up ^ Encyclopædia Britannica: Micropaedia article on "ouzo".
Jump up ^ "Greeks toast EU's ruling on ouzo". Theage.com.au. 2006-10-25. Retrieved 2011-10-14.
Jump up ^ "The world of Ouzo (Ouzo Museum) - by Ouzo Plomari". theworldofouzo.gr.
Jump up ^ Oxford English Dictionary online, Oxford University Press, retrieved September 7, 2007
Jump up ^ G. Babiniotis, Λεξικό της Νέας Ελληνικής Γλώσσας (2002), p. 1285
Jump up ^ G. Clauson, An Etymological Dictionary of Pre-Thirteenth Century Turkish, Oxford 1972, p. 288
Jump up ^ Αριστοτέλειο Πανεπιστήμιο Θεσσαλονίκης, Λεξικό της Κοινής Νεοελληνικής, 1998, s.v. ούζο
Jump up ^ Epikouria Magazine Spring/Summer 2007
Jump up ^ "The production method (of ouzo)". Tsou.gr. Retrieved 25 December 2011.
Jump up ^ Michael Paraskos, 'A perfect sundowner to replace the tired old brandy sour', in The Cyprus Mail (Cyprus newspaper), 19 April 2015
Jump up ^ Kerouac, Jack (2011-07-21). On the Road. Penguin Books Limited. ISBN 9780141912561.
Jump up ^ Amis, Kingsley (2015-10-15). Colonel Sun: James Bond 007. Random House. ISBN 9781473545267.
Jump up ^ "Χάρις Αλεξίου // η επίσημη ιστοσελίδα". www.alexiou.gr. Retrieved 2016-10-29.
Jump up ^ "Μηχανή του χρόνου: Πρέζα όταν πιεις, βρε θα ευφρανθείς . Το τραγούδι που λογόκρινε ο Μεταξάς επειδή ήταν χασικλίδικο". Retrieved 2016-10-29.
External links[edit]
OUZO: more than 600 labels of ouzo and 200 distilleries.
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text:
Bubble Tape
From Wikipedia, the free encyclopedia
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This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (April 2011) (Learn how and when to remove this template message)
Packaging and contents for Hubba Bubba Bubble Tape, Triple Mix flavour, 2015 Australian/New Zealand packaging
Bubble Tape is a brand of bubble gum produced by Wm. Wrigley Jr. Company, introduced in 1988.[1][2][3] It experienced its greatest popularity in the early 1990s due to its unique packaging and direct marketing to preteen children ("it's six feet of bubble gum - for you, not them"—"them" referring to parents or just adults in general). Today, it is still a common find in most supermarkets, although advertising campaigns for it have subsided significantly.[4]
Bubble Tape comes in a small, round, plastic container similar in size to a hockey puck. This contains six feet (1.8 m) of gum wrapped in a spiral. The container functions much like a tape dispenser, although the top half can be removed or broken off.
The white powdery substance on the gum is most likely cornstarch, which is used to prevent drying and sticking to itself.
Contents
1 Current flavors
1.1 Also available in
2 References
3 External links
Current flavors[edit]
Most are from Hubba Bubba
Awesome Original
Sour Green Apple
Sour Watermelon
Sour Blue Raspberry
Cotton Candy
Strapping Strawberry
Juicy Fruit
Gushing Grape
Snappy Strawberry
Triple Treat – A mix of strawberry, blueberry, and watermelon
Sugar Free Very Berry – A dentist-recommended version of Bubble Tape, a mix of grape and blue raspberry
Candy Cane – A seasonal flavor
Tangy Tropical
Cola Party
Also available in[edit]
Mega Roll – 10 feet (3.0 m) of Bubble Tape gum
King Size – 9 feet (2.7 m) of Bubble Tape gum
References[edit]
Jump up ^ https://books.google.com/books?id=EgxrLGtHzukC&pg=PA256&lpg=PA256&dq=bubble+tape+1988&source=bl&ots=bP9vcmMAgW&sig=8dnNwfXK6Eb-7KGDL0WYSs4IW28&hl=en&sa=X&ved=0ahUKEwif87Lm04LTAhXMKiYKHT0qAQcQ6AEIMzAH#v=onepage&q=bubble%20tape%201988&f=false
Jump up ^ "Trade registration information for "Bubble Tape"". Retrieved 6 Apr 2011.
Jump up ^ "Article describing the creation of the packaging of Bubble Tape". Retrieved 6 Apr 2011.
Jump up ^ Winn, John. "Bubble Tape – Six Feet of Fun". Racket Magazine. Retrieved 26 Jan 2009.
External links[edit]
Official site
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This confectionery-related article is a stub. You can help Wikipedia by expanding it.
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