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均苯三酚：修订间差异

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'''均苯三酚,'''，又稱'''間苯三酚'''，是一種化學式為 C<sub>6</sub>H<sub>6</sub>O<sub>3</sub>的[[有機化合物]]。固體成無色至淡黃色，屬於[[酚類]]化合物。是[[苯三酚]]（[[三羥基苯]]）三個[[異構體]]之一，三個[[羥基]]取代了1、3、5號碳（均）上面的氫。均苯三酚可用於[[藥物]]（[[INN]]：Phloroglucinol）與[[炸藥]]（如[[1,3,5-三硝基苯]]<ref name=Ullmann>{{Cite book | last1 = Fiege | first1 = H. | last2 = Voges | first2 = H. W. | last3 = Hamamoto | first3 = T. | last4 = Umemura | first4 = S. | last5 = Iwata | first5 = T. | last6 = Miki | first6 = H. | last7 = Fujita | first7 = Y. | last8 = Buysch | first8 = H. J. | last9 = Garbe | first9 = D. | last10 = Paulus | doi = 10.1002/14356007.a19_313 | first10 = W. | chapter = Phenol Derivatives | title = Ullmann's Encyclopedia of Industrial Chemistry | year = 2000 | isbn = 978-3527306732 | pmid = | pmc = | url = https://books.google.com/books?id=IY-YtwEACAAJ | access-date = 2020-07-19 | archive-date = 2020-07-25 | archive-url = https://web.archive.org/web/20200725100948/https://books.google.com/books?id=IY-YtwEACAAJ | dead-url = no }}</ref> ).）的合成。會以二水合物出現<ref name=basechem>{{ cite web | url =http://www.basechem.org/chemical/35803 | title =间苯三酚二水合物 | work = | publisher = 物竞数据库 | accessdate =2020-07-19 | archive-date =2020-07-19 | archive-url =https://web.archive.org/web/20200719073217/http://www.basechem.org/chemical/35803 | dead-url =no }}</ref>。
{{chembox
| Watchedfields = changed
| verifiedrevid = 459445024
| Name = Phloroglucinol
| ImageFileL1 = phloroglucinol structure.png
| ImageFileR1 = Phloroglucinol-3D.png
| IUPACName = Benzene-1,3,5-triol <br />1,3,5-三羥基苯
| OtherNames = 環己烷-1，3，51,3,5-三酮、1,3,5-苯三酚、均苯三酚、間苯三酚
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
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}}
}}
 
==製備==
均苯三酚最初次于1855年由[[根皮素]]合成而來，當時為1855年。<ref>{{cite journal|last1=Hlasiwetz|first1=Heinrich|title=Ueber das Phloretin|journal=Annalen der Chemie und Pharmacie|date=1855|volume=96|issue=1|pages=118–123|url=https://babel.hathitrust.org/cgi/pt?id=uva.x002457945;view=1up;seq=518|trans-title=On phloretin|doi=10.1002/jlac.18550960115|access-date=2020-07-19|archive-date=2020-07-30|archive-url=https://web.archive.org/web/20200730111538/https://babel.hathitrust.org/cgi/pt?id=uva.x002457945|dead-url=no}} On p. 120, Hlasiwetz named phloroglucin: ''"Die auffallendste Eigenschaft dieses Körpers ist, daſs er überaus süſs schmeckt, weſshalb er bis auf weiteres Phloroglucin genannt sein mag."'' (The most striking property of this substance is that it tastes extremely sweet, for which reason it may be named "phloroglucin" until further [information emerges].)</ref>
 
現代的均苯三酚是由[[苯]]或[[1,3,5-三硝基苯]]（由苯加[[硝酸]][[硝化]]而得）製成的<ref name=Ullmann/>，如下圖所示：
[[Image:Synthesis of phloroglucinol.svg|600px]]
 
用[[錫]]粒[[還原]][[1，3，51,3,5-三硝基苯甲酸]]，可製得[[1，3，51,3,5-三氨基苯甲酸]],。加熱[[回流]]其稀[[溶液]],，再用[[鹽酸]][[酸化]],，冷卻[[結晶]],，可得均苯三酚<!-- 需要替换可靠来源 <ref>{{ cite web | url =http://baike.molbase.cn/cidian/22802 | title = 间苯三酚 | work = | publisher = 摩貝百科}}</ref> -->。▼
 
在[[催化劑]]的存在下，[[苯]]和[[丙烯]]反应，[[精餾]]所得混合物，取得[[三異丙基苯]]<ref>{{cite journal|title=Study on the synthesis of 1, 3, 5-triisopropylbenzene |author=Jiang, B.and Li, Y.|year=2010/06/01}}</ref>。然後通入[[壓縮空氣]]，利用[[偶氮雙自由基引發劑]]作為催化劑，進行[[自然氧化]]。在反應中生成的[[醇類]][[副產品]]用[[過氧化氫]]在酸性條件下[[氧化]]，變為[[1,3,5- 三異丙苯三氫過氧化物]]。過氧化物在催化劑作用下分解為間苯三酚。所得的產物為酸性間苯三酚，用[[氫氧化鈉]][[中和反應|中和]]，[[重结結晶]]之後可得中性的純間苯三酚。<ref>{{ cite web | url name=http://www.basechem.org/chemical/35803 | title =间苯三酚二水合物 | work = | publisher = 物竞数据库 }}</ref>▼
 
在生物合成上，[[根皮素水解酶]]可以[[催化]][[根皮素]]的[[水解]]，生成[[對羥基苯丙酸]]和均苯三酚<ref> {{cite journal | vauthors = Minamikawa T, Jayasankar NP, Bohm BA, Taylor IE, Towers GH | date = 1970 | title = An inducible hydrolase from Aspergillus niger, acting on carbon-carbon bonds, for phlorrhizin and other C-acylated phenols | url = https://archive.org/details/sim_biochemical-journal_1970-03_116_5/page/889 | journal = Biochem. J. | volume = 116 | pages = 889&ndash;97 | pmid = 5441377 | issue = 5 | pmc = 1185512 }}</ref>。
 
==反應==
均苯三酚可以發生[[酮-烯醇互变异构|酮-烯醇互變]]，可以與[[氨]]發生反應，生成[[均苯三胺]]。<ref>{{Cite book|title=《有机化学》第四版上册|last=曾昭瓊|first=《有机化学》第四版上册|publisher=高等教育出版社|year=2005年|isbn= 704013845X|location=|pages=}}</ref>
 
亦可發生[[Hoesch反应|Hoesch反應]]，生成一個[[芳基酮]]。此反應是[[酰化反應]]，需要[[酸]]作爲[[催化劑]]催化反應。例如，均苯三酚與[[乙腈]]反應生成[[2-乙酰基均苯三酚]]，如下<ref>K. C. Gulati, S. R. Seth, and K. Venkataraman, "[http://www.orgsynth.org/orgsyn/pdfs/CV2P0522.pdf Phloroacetophenone] {{Wayback|url=http://www.orgsynth.org/orgsyn/pdfs/CV2P0522.pdf |date=20110124064811 }}", ''[[Organic Syntheses]]'', ''Coll. Vol.'' '''2''', p.522 (1943); ''Vol.'' '''15''', p.70 (1935).</ref>
:[[Image:Houben-Hoesch reaction.svg|800px|Houben-Hoesch反应]]
 
==用途==
===染料===
均苯三酚可用作[[染髮水]]、[[染料]]等。<ref>{{cite web| url =https://comptox.epa.gov/dashboard/dsstoxdb/results?search=DTXSID9048354#chemical-functional-use| title =1,3,5-Trihydroxybenzene| work =| publisher =United States Environmental Protection Agency| accessdate =2020-07-19| archive-date =2020-07-19| archive-url =https://web.archive.org/web/20200719082454/https://comptox.epa.gov/dashboard/dsstoxdb/results?search=DTXSID9048354#chemical-functional-use| dead-url =no}}</ref>
===藥品===
均苯三酚的[[ATC代碼]]為A03AX12，治療[[功能性腸道疾病]]，可治療[[膽石]]等腸胃病<ref>{{cite web | title=Phloroglucinol Summary Report | publisher=EMEA | url=http://www.emea.europa.eu/pdfs/vet/mrls/004695en.pdf | accessdate=2009-04-24 | dead-url=yes | archiveurl=https://web.archive.org/web/20070710215947/http://www.emea.europa.eu/pdfs/vet/mrls/004695en.pdf | archivedate=2007-07-10 }}</ref>。[[酰化]]的均苯三酚亦可用作[[脂肪酸合酶]]的[[抑制劑]]<ref>{{cite journal|title=Fatty acid synthase inhibitory activity of acylphloroglucinols isolated from Dryopteris crassirhizoma|author= Na, M.; Jang, J.; Min, B. S.; Lee, S. J.; Lee, M. S.; Kim, B. Y.; Oh, W. K.; Ahn, J. S. |year=2006}}</ref>。常見用藥形式為注射，注射液裏除了有均苯三酚為有效成分之外，還有[[三甲基間苯三酚]]、[[氯化鈉]]、[[亞硫酸氫鈉]]、[[檸檬酸]]、[[磷酸氫二鈉|十二水合磷酸氫二鈉]]等輔料。<ref>{{cite web | title=间苯三酚注射液 | publisher=医脉通用藥參考 | url=http://drugs.medlive.cn/drugref/html/678.shtml | accessdate=2020-07-19 | archive-date=2020-07-19 | archive-url=https://web.archive.org/web/20200719100538/http://drugs.medlive.cn/drugref/html/678.shtml | dead-url=no }}</ref>
 
===鑒定===
均苯三酚是測定[[五碳糖]]（戊糖）的[[多侖試劑]]的一個反應物，這個測試的精要在於均苯三酚和[[糖醛]]的顯色反應。<ref>Oshitna, K., and Tollens, B., Ueber Spectral-reactionen des Methylfurfurols. Ber. Dtsch. Chem. Ges. 34, 1425 (1901)</ref>
 
均苯三酚的[[鹽酸]]溶液可用來測定[[木質素]]，[[陽性反應]]為溶液變為紅色。原理是木質素裏含有[[松柏醛]]基團<ref>Lignin production and detection in wood. John M. Harkin, U.S. Forest Service Research Note FPL-0148, November 1966 ([http://www.fpl.fs.fed.us/documnts/fplrn/fplrn0148.pdf article] {{Wayback|url=http://www.fpl.fs.fed.us/documnts/fplrn/fplrn0148.pdf |date=20200305091429 }})</ref>。亦可用[[甲苯胺藍]]來進行相似的實驗。
 
均苯三酚和[[香草醛]]的[[酒精]]溶液可用來測定[[氫氯酸]]（或[[胃酸]]中的鹽酸），如果鹽酸存在，溶液會變爲紅色<ref>{{cite book|author1=G. P. TALWAR|author2=L .M. SRIVASTAVA|title=TEXTBOOK OF BIOCHEMISTRY AND HUMAN BIOLOGY|url=https://books.google.com/books?id=LKy0weDEFp8C&pg=PA620|date=2002-01-01|publisher=PHI Learning Pvt. Ltd.|isbn=978-81-203-1965-3|page=620|access-date=2020-07-19|archive-date=2014-07-04|archive-url=https://web.archive.org/web/20140704132757/http://books.google.com/books?id=LKy0weDEFp8C&pg=PA620|dead-url=no}}</ref>。
 
甲醛與均苯三酚在鹼性條件下反應生成橘紅色化合物，用於檢驗衣服有沒有甲醛<ref name=chemicalbook>{{cite web | title=间苯三酚 | publisher=Chemical book | url=https://www.chemicalbook.com/ProductChemicalPropertiesCB0667672.htm | accessdate=2020-07-19 | archive-date=2015-03-11 | archive-url=https://web.archive.org/web/20150311120015/http://www.chemicalbook.com/ProductChemicalPropertiesCB0667672.htm | dead-url=no }}</ref>。
 
另外，均苯三酚可以用來鑒定[[銻]]、[[砷]]、[[鈰]]、[[鉻]]、[[金]]、[[鐵]]、[[汞]]、[[錫]]、[[釩]]、[[亞硝酸鹽]]、[[鉻酸鹽]]等金屬和無機鹽。也可用來鑒定骨頭標本的脱鈣。<ref name=chemicalbook />
 
===有機合成===
現代的均苯三酚是由[[苯]]或[[1，3，5三硝基苯]]（由苯加[[硝酸]][[硝化]]而得）製成的<ref name=Ullmann>{{Cite book | last1 = Fiege | first1 = H. | last2 = Voges | first2 = H. W. | last3 = Hamamoto | first3 = T. | last4 = Umemura | first4 = S. | last5 = Iwata | first5 = T. | last6 = Miki | first6 = H. | last7 = Fujita | first7 = Y. | last8 = Buysch | first8 = H. J. | last9 = Garbe | first9 = D. | last10 = Paulus | doi = 10.1002/14356007.a19_313 | first10 = W. | chapter = Phenol Derivatives | title = Ullmann's Encyclopedia of Industrial Chemistry | year = 2000 | isbn = 978-3527306732 | pmid = | pmc = | url = https://books.google.com/books?id=IY-YtwEACAAJ }}</ref> ,如下圖所示：
[[可使保朗]]是由均苯三酚透過[[Hoesch反應]]合成而來的。可使保朗是一種藥物， 具有緩解[[消化管平滑肌]]以及[[胰膽道平滑肌]]收縮[[痙攣]]的功能<ref>{{cite web|url=https://dept.ntuh.gov.tw/phar/WebAp/EducationPapers/Flopropione.pdf|title=Flopropione 膠囊|format=pdf|date=|accessdate=|archive-date=2020-07-19|archive-url=https://web.archive.org/web/20200719110543/https://dept.ntuh.gov.tw/phar/WebAp/EducationPapers/Flopropione.pdf|dead-url=no}}</ref>。
[[Image:Phlorosynth.png|600px]]
 
不同的爆炸物也是由均苯三酚製備而成。[[1,3,5-三硝基苯]]<ref>A facile two-step Synthesis of 1,3,5-trinitrobenzene. Bottaro Jeffrey C, Malhotra Ripudaman and Dodge Allen, Synthesis, 2004, no 4, pages 499-500, {{INIST|15629637}}</ref>)、[[三硝基均苯三酚]]<ref>{{cite web | year=1984 | title=Synthesis of trinitrophloroglucinol | publisher=The United States Patent and Trademark Office | url=http://www.freepatentsonline.com/4434304.html | accessdate=2009-04-24 | archive-date=2012-10-02 | archive-url=https://web.archive.org/web/20121002141449/http://www.freepatentsonline.com/4434304.html | dead-url=no }}</ref>等正是用均苯三酚合成的。
▲用[[錫]]粒[[還原]][[1，3，5-三硝基苯甲酸]]，可製得[[1，3，5-三氨基苯甲酸]],加熱[[回流]]其稀[[溶液]],再用[[鹽酸]][[酸化]],冷卻[[結晶]],可得均苯三酚<ref>{{ cite web | url =http://baike.molbase.cn/cidian/22802 | title = 间苯三酚 | work = | publisher = 摩貝百科}}</ref>。
 
▲在催化劑的存在下，苯和丙烯反应，精餾所得混合物，取得三異丙基苯。然後通入壓縮空氣，利用偶氮雙自由基引發劑作為催化劑，進行自然氧化。在反應中生成的醇類副產品用過氧化氫在酸性條件下氧化，變為1,3,5- 三異丙苯三氫過氧化物。過氧化物在催化劑作用下分解為間苯三酚。所得的產物為酸性間苯三酚，用氫氧化鈉中和，重结晶可得中性的純間苯三酚。<ref>{{ cite web | url =http://www.basechem.org/chemical/35803 | title =间苯三酚二水合物 | work = | publisher = 物竞数据库 }}</ref>
==參考資料==
{{Reflist|2}}
{{芳香族化合物}}
 
[[Category:均苯三酚|*]]
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[[Category:1850年代发现的物质]]
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