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Revision as of 02:20, 15 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Drugbox validation		Latest revision as of 11:41, 2 February 2024 edit Project Osprey (talk | contribs)Extended confirmed users9,954 editsmNo edit summary
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	{{chembox		{{Chembox
			| Verifiedfields = changed
	| verifiedrevid = 434609276
			| verifiedrevid = 450575128
	| ImageFile = Polyvinylpyrrolidon.svg
			| ImageFile = 2-vinylpyridine structure.png
	| ImageSize = 150px		| ImageSize = 150px
			| PIN = 2-Ethenylpyridine
	| IUPACName = Polyvinylpyrrolidone
	| OtherNames =		| OtherNames = 2-Vinylpyridine<br />2VP
			|Section1={{Chembox Identifiers
	PVP, Povidone, Polyvidone
	Poly
	1-Ethenyl-2-pyrrolidon homopolymer
	1-Vinyl-2-pyrrolidinon-Polymere
	Copovidone
	PNVP
	| Section1 = {{Chembox Identifiers
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 9003-39-8		| CASNo = 100-69-6
	| PubChem =		| PubChem = 7521
			| ChEMBL =
	| SMILES = C=CN1CCCC1=O }}
			| EC_number = 202-879-8
	| Section2 = {{Chembox Properties
			| RTECS = UU1040000
	| Formula = (C<sub>6</sub>H<sub>9</sub>NO)<sub>n</sub>
			| UNNumber = 3073
	| MolarMass = 2.500 - 2.5000.000 g·mol<sup>−1</sup>
			| UNII = DT4UV4NNKX
	| Appearance = white to light yellow, hygroscopic, amorphous powder
	| Density = 1.2 g/cm³		| Beilstein = 104505
			| SMILES = C=CC1=CC=CC=N1
	| MeltingPt = 150 - 180 °C (glass temperature)
			| ChemSpiderID = 7240
	| BoilingPt =
			| InChI = 1/C7H7N/c1-2-7-5-3-4-6-8-7/h2-6H,1H2
	| Solubility = }}
			| InChIKey = KGIGUEBEKRSTEW-UHFFFAOYAO
	| Section3 = {{Chembox Hazards
			| StdInChI = 1S/C7H7N/c1-2-7-5-3-4-6-8-7/h2-6H,1H2
	| FlashPt =
			| StdInChIKey = KGIGUEBEKRSTEW-UHFFFAOYSA-N}}
	| Autoignition = }}
			|Section2={{Chembox Properties
			| C=7 | H=7 | N=1
			| Appearance = colorless liquid
			| Density = 0.977 g/cm<sup>3</sup>
			| MeltingPtC = -50
			| BoilingPtC = 158
			| Solubility = 27.5 g/L
			| Viscosity = 1.17 mPas
			| VaporPressure = 96 hPa (72 mmHg) at 100 °C
			| pKa = 4.98}}
			|Section3={{Chembox Hazards
			| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|226|301|302|311|314|317|331|411}}
			| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|272|273|280|301+310|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|311|312|321|322|330|333+313|361|363|370+378|391|403+233|403+235|405|501}}
			| FlashPtC = 48
			| AutoignitionPtC = }}
	}}		}}
			'''2-Vinylpyridine''' is an ] with the formula CH<sub>2</sub>CHC<sub>5</sub>H<sub>4</sub>N. It is a derivative of ] with a ] in the 2-position, next to the nitrogen. It is a colorless liquid, although samples are often brown. It is used industrially as a precursor to specialty ]s and as an intermediate in the chemical, pharmaceutical, dye, and photo industries.<ref name=Ullmann>{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}</ref> Vinylpyridine is sensitive to polymerization. It may be stabilized with a ] such as ]. Owing to its tendency to polymerize, samples are typically refrigerated.
	'''Polyvinylpyrrolidone''' ('''PVP'''), also commonly called Polyvidone or Povidone, is a water-soluble ] made from the ] ]:<ref>{{cite journal |author=F. Haaf, A. Sanner and F. Straub |title=Polymers of N-Vinylpyrrolidone: Synthesis, Characterization and Uses |journal=Polymer Journal |volume=17 |issue=1 |pages=143–152 |year=1985 |pmid= |doi=10.1295/polymj.17.143}}</ref>
			==Synthesis==
	:]{{clear-left}}
			It was first synthesized in 1887. A contemporary preparation entails condensation of ] with formaldehyde, followed by ] of the intermediate alcohol. The reaction is carried out between 150–200&nbsp;°C in an autoclave. The conversion is kept relatively low. After removal of unreacted 2-methylpyridine by distillation, concentrated aqueous ] is added to the residue and the resultant mixture is distilled under reduced pressure. During distillation, the dehydration of 2-(2-pyridyl)ethanol occurs to give 2-vinylpyridine, which can be purified further by fractional distillation under reduced pressure in the presence of an inhibitor such as ].<ref name=Ullmann/>
			:CH<sub>3</sub>C<sub>5</sub>H<sub>4</sub>N + CH<sub>2</sub>O → HOCH<sub>2</sub>CH<sub>2</sub>C<sub>5</sub>H<sub>4</sub>N
			:HOCH<sub>2</sub>CH<sub>2</sub>C<sub>5</sub>H<sub>4</sub>N → CH<sub>2</sub>=CHC<sub>5</sub>H<sub>4</sub>N + H<sub>2</sub>O
			An alternative synthesis involves the reaction of ] and ] below 130–140 ̊C in the presence of ]s as a catalyst.<ref name=Ullmann/> Acrylonitrile is the solvent for the reaction.<ref name=Bonn/>
	== Properties ==
			:]
			==Uses==
	PVP is soluble in ] and other polar ]s. When dry it is a light flaky powder, which readily absorbs up to 40% of its weight in atmospheric water. In solution, it has excellent wetting properties and readily forms films. This makes it good as a coating or an additive to coatings.
			===Polymeric derivatives===
			2-Vinylpyridine is readily polymerized or copolymerized with ], ], ], ], and other compounds in the presence of radical, cationic, or anionic initiators. The homopolymer is soluble in organic solvents such as ] and ], whereas cross-linked copolymers are insoluble in organic solvents.
			An important application of 2-vinylpyridine involves the production of a latex terpolymer of 2-vinylpyridine, ], and ], for use as a tire-cord binder. The tire cord is treated first with a ]-] polymer and then with a terpolymer made from 15% 2-vinylpyridine, styrene, and butadiene. This treatment gives the close bonding of tire cord to rubber.
	== History ==
			2-Vinylpyridine is a co-monomer for acrylic fibers. Between 1–5% of copolymerized 2-vinylpyridine provide the reactive sites for dyes.<ref name=Bonn>Bönnemann, H.; Brijoux, W.. Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. 2008, p. 188</ref>
	PVP was first synthesized by Prof. ] and a patent was filed in 1939 for one of the most interesting derivatives of acetylene chemistry. PVP was initially used as a blood plasma substitute and later in a wide variety of applications in medicine, pharmacy, cosmetics and industrial production.<ref>{{cite journal |first1=Frank |last1=Fischer |first2=Stephan |last2=Bauer |title=Polyvinylpyrrolidon. Ein Tausendsassa in der Chemie |journal=Chemie in unserer Zeit |volume=43 |issue=6 |pages=376–383 |year=2009 |pmid= |doi=10.1002/ciuz.200900492}}</ref>
	== Uses ==		===Organic synthesis===
			Due to the electron-withdrawing effect of the ring nitrogen atom, 2-vinylpyridine adds ]s such as ], ], ] at the vinylic site to give addition products. The addition product of methanol to 2-vinylpyridine, 2-(2-methoxyethyl)pyridine is a veterinary ].<ref name=Ullmann/>
			Treating 2-vinylpyridine with 4-pyridinecarbonitrile and ] gives 1--4-cyanopyridinium chloride, which then can be used to prepare ] (DMAP), a widely used base catalyst.
	The ] is extremely toxic to aquatic life.
			2-Vinylpyridine is used in the production of ], a pharmaceutical.
	=== Medical ===
			==See also==
	The ] PVP was used as a ] expander for trauma victims after the first half of the 20th century.
			* ]
	It is used as a ] in many pharmaceutical tablets;<ref>{{cite book |last=Bühler |first=Volker |year=2005 |title=Excipients for Pharmaceuticals - Povidone, Crospovidone and Copovidone |publisher=Springer |location=Berlin, Heidelberg, New York |isbn=978-3-540-23412 | pages=1–254}}</ref> it simply passes through the body when taken orally. However, autopsies have found that crospovidone does contribute to pulmonary vascular injury in substance abusers who have injected pharmaceutical tablets intended for oral consumption.<ref>Santhi Ganesan M.D Embolized Crospovidone (poly) in the Lungs of Intravenous Drug Users Mod Pathol 2003;16(4):286–292 </ref> The long-term effects of crospovidone within the lung are unknown. PVP added to ] forms a complex called ] that possesses ] properties.<ref> Accessed January 25, 2007
	</ref> This complex is used in various products like solutions, ], ], liquid soaps and surgical scrubs. It is known for instance under the trade name ].
	It is used in ] (fusion of the pleura because of incessant pleural effusions). For this purpose, povidone iodine is equally effective and safe as ], and may be preferred because of easy availability and low cost.<ref>{{cite journal |author=Das SK, Saha SK, Das A, Halder AK, Banerjee SN, Chakraborty M |title=A study of comparison of efficacy and safety of talc and povidone iodine for pleurodesis of malignant pleural effusions |journal=Journal of the Indian Medical Association |volume=106 |issue=9 |pages=589–90, 592 |year=2008 |month=September |pmid=19552086}}</ref>
	=== Technical ===
	PVP is also used in many technical applications:
	* as an adhesive in ] and ]s
	* as a special additive for ], ]s, ], ]s, ] and in the ] process
	* as an ] and disintegrant for ]
	* as a ] for ] (CRT)
	* used in aqueous ] ]
	* for production of ], such as ] and ] filters
	* as a binder and complexation agent in agro applications such as ] protection, ] treatment and ]
	* as a thickening agent in tooth whitening gels<ref>United States Patent 6730316</ref>
	* as an aid for increasing the solubility of drugs in liquid and semi-liquid dosage forms (], soft gelatine ]) and as an inhibitor of ]
	* as an additive to Doro's RNA extraction buffer
	* as a liquid-phase dispersion enhancing agent in DOSY ] <ref>http://pubs.acs.org/doi/abs/10.1021/ol9001398</ref>
	=== Other uses ===
	PVP binds to ]s exceptionally well, owing to its ]. This has led to its application in coatings for photo-quality ink-jet papers and transparencies, as well as in inks for ]s.
	PVP is also used in personal care products, such as ]s and ]s, in ]s, and ]s that must be moistened, such as old-style ]s and ]s. It has also been used in ] solutions and in ]-quenching solutions.<ref>{{cite journal |author= Dr. Stephan Bauer, Dr. Frank Fischer|title=Ein Polyvinylpyrrolidon (PVP): ein vielseitiges Spezialpolymer – Verwendung in der Keramik und als Metallabschreckmedium |volume=61 |issue=6|pages=382–385 |year=2009 |pmid= |doi= }}</ref><ref>{{cite journal |first1=Alexander |last1=Göthlich |first2=Sebastian |last2=Koltzenburg |first3=Gunnar |last3=Schornick |title=Funktionale Polymere im Alltag: Vielseitig |journal=Chemie in Unserer Zeit |volume=39 |issue=4 |pages=262–273 |year=2005 |pmid= |doi=10.1002/ciuz.200400346}}</ref> PVP is the basis of the early formulas for ]s and ]s, and still continues to be a component of some.
	As a ], PVP is a ] and has ] '''E1201'''. PVPP is '''E1202'''. It is also used in the wine industry as a ] for ]. Other references state that polyvinyl pyrrolidone and its derivatives are fully from mineral synthetic<ref>http://www.ispcorp.com/products/pharma/content/brochure/plasdonePovidone/PlasdonePovidone.pdf</ref> origin. Therefore, its use in the production should not be a problem for vegans.
	In ], PVP can be used as a blocking agent during ] analysis as a component of ]. It is also exceptionally good at absorbing polyphenols during DNA purification. Polyphenols are common in many plant tissues and can deactivate proteins if not removed and therefore inhibit many downstream reactions like PCR.
	In ], PVP is useful for making an aqueous mounting medium.<ref>Lillie RD & Fullmer HM (1976) Histopathologic Technic and Practical Histochemistry, 4th ed. New York: McGraw-Hill, p.411. ISBN 0070378622.</ref>
	== Safety ==
	The U.S. ] (FDA) has approved this chemical for many uses,<ref>Inactive Ingredients in FDA Approved Drugs. FDA/Center for Drug Evaluation and Research, Office of Generic Drugs, Division of Labeling and Program Support. Database Update Frequency: Quarterly. Data Through: January 6, 2010. Database Last Updated: January 13, 2010. Available at http://www.accessdata.fda.gov/scripts/cder/iig/index.cfm Accessed April 7, 2010 - search on povidone for list of approved items</ref> and it is generally considered safe. However, there have been documented cases of ] reactions to PVP/povidone, particularly regarding ] (applied under the skin) use and situations where the PVP has come in contact with autologous ] (internal blood fluids) and ]s. For example, a boy having an ] response after application of ] for treatment of ] was found to be ] to the PVP component of the solution.<ref>{{cite journal |author=Yoshida K, Sakurai Y, Kawahara S, ''et al.'' |title=Anaphylaxis to polyvinylpyrrolidone in povidone-iodine for impetigo contagiosum in a boy with atopic dermatitis |journal=International Archives of Allergy and Immunology |volume=146 |issue=2 |pages=169–73 |year=2008 |pmid=18204285 |doi=10.1159/000113522}}</ref> A woman, who had previously experienced ] (]) from various hair products, later found to contain PVP, had an ] response after ] solution was applied internally. She was found to be ] to PVP.<ref>{{cite journal |author=Adachi A, Fukunaga A, Hayashi K, Kunisada M, Horikawa T |title=Anaphylaxis to polyvinylpyrrolidone after vaginal application of povidone-iodine |journal=Contact Dermatitis |volume=48 |issue=3 |pages=133–6 |year=2003 |month=March |pmid=12755725 |doi=10.1034/j.1600-0536.2003.00050.x}}</ref> In another case, a man experiencing ] after taking ] ]s orally was found to be ] to PVP.<ref>{{cite journal |author=Rönnau AC, Wulferink M, Gleichmann E, ''et al.'' |title=Anaphylaxis to polyvinylpyrrolidone in an analgesic preparation |journal=The British Journal of Dermatology |volume=143 |issue=5 |pages=1055–8 |year=2000 |month=November |pmid=11069520 |doi=10.1046/j.1365-2133.2000.03843.x}}</ref>
	Povidone is commonly used in conjunction with other ]. Some of these, such as ], are blamed for ] responses, although testing results in some patients show no signs of ] to the suspect ]. ] attributed to these other ] may possibly be caused by the PVP instead.<ref>Katelaris, Constance (2009). "'Iodine Allergy' label is misleading". ''Australian Prescriber'', Vol. 32, 125-128. Available at http://www.australianprescriber.com/magazine/32/5/125/8/ Accessed April 7, 2010</ref><ref>{{cite journal |author=van Ketel WG, van den Berg WH |title=Sensitization to povidone-iodine |journal=Dermatologic Clinics |volume=8 |issue=1 |pages=107–9 |year=1990 |month=January |pmid=2302848}}</ref>
	== Cross-linked derivatives ==
	{{main article|Polyvinylpolypyrrolidone}}
	== See also ==
	]
	== Notes ==
			==References==
	{{Reflist}}		{{Reflist}}
			{{DEFAULTSORT:Vinylpyridine, 2-}}
	== External links ==
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	* Accessed August 1, 2008
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	* Accessed November 26, 2007
	* Accessed January 25, 2007
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