{{위키데이터 속성 추적}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 446532204
| Name       = 프탈산
| ImageFile  = Phthalic-acid-2D-skeletal.png
| ImageSize  = 150px
| ImageName  = Phthalic acids
| ImageFile1 = Phthalic acid 3D ball.png
| ImageSize1 = 170px
| ImageAlt1  = Ball-and-stick model of the phthalic acid molecule
| PIN = benzene-1,2-dicarboxylic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
| OtherNames = 1,2-benzenedioic acid,<br>phthalic acid,<br>benzene-1,2-dioic acid,<br>''ortho''-phthalic acid
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 992
| SMILES     = OC(=O)c1ccccc1C(=O)O
| InChI      = 1/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)
| InChIKey   = XNGIFLGASWRNHJ-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI   = 1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = XNGIFLGASWRNHJ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo      = 88-99-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6O7F7IX66E
| EINECS     = 201-873-2
| PubChem    = 1017
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI      = 29069
  }}
|Section2={{Chembox Properties
| Formula    = C<sub>8</sub>H<sub>6</sub>O<sub>4</sub>
| MolarMass  = 166.132 g/mol
| Appearance = 흰색 고체
| Density    = 1.593 g/cm<sup>3</sup>, 고체
| Solubility = 0.6 g / 100 mL<ref>{{웹 인용|url=http://hazard.com/msds/mf/baker/baker/files/p4270.htm|title=PHTHALIC ACID|website=hazard.com}}</ref>
| pKa        = 2.89, 5.51<ref>Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., ''Determination of Organic Structures by Physical Methods'', Academic Press, New York, 1955.</ref>
| MeltingPtC = 207
| MeltingPt_ref =<ref>Several melting points are reported, for example: (i) 480. K (NIST website), (ii) 210−211&nbsp;°C with decomposition (Sigma-Aldrich on-line), (iii) 191&nbsp;°C in a sealed tube (Ullmann's Encyclopedia of Industrial Chemistry), (iv)  230&nbsp;°C with conversion to phthalic anhydride and water (J.T.Baker MSDS).</ref>
| MagSus     = -83.61·10<sup>−6</sup> cm<sup>3</sup>/mol
  }}
|Section4={{Chembox Thermochemistry
  }}
|Section7={{Chembox Hazards
| NFPA-H  = 2
| NFPA-F  = 0
| NFPA-R  = 0
  }}
|Section8={{Chembox Related
| OtherFunction_label = [[카복실산]]
| OtherFunction   = [[아이소프탈산]],<br />[[테레프탈산]]
| OtherCompounds  = [[프탈산 무수물]],<br />[[프탈이미드]],<br />[[프탈하이드라자이드]],<br />[[염화 프탈로일]],<br />[[프탈알데하이드]]
  }}
}}

'''프탈산'''({{llang|en|phthalic acid}}) 또는 '''1,2-벤젠다이카복실산'''({{llang|en|1,2-benzenedicarboxylic acid}})은 [[화학식]]이 C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>H)<sub>2</sub>.인 [[방향족성|방향족]] [[다이카복실산]]이다. 프탈산은 상업적으로 중요하지는 않지만, 밀접하게 관련된 유도체인 [[프탈산 무수물]]은 대규모로 생산되는 필수 화학 물질이다.<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a20_181.pub2|title=Phthalic Acid and Derivatives|year=2007|last1=Lorz|first1=Peter M.|last2=Towae|first2=Friedrich K.|last3=Enke|first3=Walter|last4=Jäckh|first4=Rudolf|last5=Bhargava|first5=Naresh|last6=Hillesheim|first6=Wolfgang}}</ref> 프탈산은 [[벤젠다이카복실산]]의 3가지 [[이성질체]]들 중 하나이며, 나머지는 [[아이소프탈산]]과 [[테레프탈산]]이다.

== 생산 ==
프탈산은 [[나프탈렌]] 또는 [[오르토-자일렌]]을 [[프탈산 무수물]]로 직접 촉매 산화시킨 후 무수물을 [[가수분해]]하여 생성한다.<ref name=Ullmann/>

프탈산은 1836년에 [[프랑스]]의 [[화학자]]인 [[오귀스트 로랑]]이 사염화 나프탈렌을 [[산화]]시켜 처음으로 생성하였다.<ref name=EB1911>{{cite EB1911 |wstitle=Phthalic Acids |volume=21 |pages=545–546}}</ref> 그는 생성된 물질이 나프탈렌 유도체라고 믿었고, 생성물을 "나프탈산(naphthalic acid)"이라고 명명했다.<ref name=EB1911/><ref>See:
*  Auguste Laurent (1836) [https://books.google.com/books?id=uhwAAAAAMAAJ&pg=PA113#v=onpage&q&f=false "Sur l'acide naphtalique et ses combinaisons"] (On naphthalic acid and its compounds), ''Annales de Chimie et de Physique'', '''61''' :  113-125. (Note:  The empirical formulae of the compounds that were analyzed in this article are incorrect, in part because, during this period, chemists used incorrect atomic masses for carbon (6 instead of 12) and other elements.)
*  Reprinted in German as:  Auguste Laurent (1836) [https://books.google.com/books?id=vks9AAAAcAAJ&pg=PA38#v=onepage&q&f=false "Ueber Naphthalinsäure und ihre Verbindungen"] (On naphthalenic acid and its compounds), ''Annalen der Pharmacie'', '''19''' (1) : 38-50; for the preparation of phthalic acid, see page 41.</ref> 이후에 [[스위스]]의 화학자인 [[장 샤를 갈리사르 드 마리냐크]]가 정확한 화학식을 결정한 후<ref>C. de Marignac (1841) [https://books.google.com/books?id=eJpKAAAAYAAJ&pg=RA1-PA13#v=onepage&q&f=false "Ueber die Naphtalinsäure und ein bei ihrer Darstellung entstehendes flüchtiges Produkt"] ("On naphthalinic acid and a volatile product that arises during its preparation"), ''Annalen der Chemie und Pharmacie'', '''38''' (1) : 13-20. (Note:  Again, Marignac's empirical formulae are wrong because chemists at this time used incorrect atomic masses.)</ref> 로랑이 현재의 이름을 부여했다.<ref name=EB1911/><ref>See:
*  Auguste Laurent (1841) [https://books.google.com/books?id=ad0pEVRTcmEC&pg=PA76#v=onepage&q&f=false "Sur de nouvelles combinaisons nitrogénées de la naphtaline et sur les acides phtalique et nitrophtalique"] (On new nitrogenous compounds of naphthalene, and on phthalic acid and nitrophthalic acid), ''Revue Scientifique et Industrielle'', '''6''' : 76-99; on page 92, Laurent coins the name "acide phtalique" (phthalic acid) and admits that his earlier empirical formula for phthalic acid was wrong.
*  Reprinted in German as:  Auguste Laurent (1842) [https://books.google.com/books?id=ZE09AAAAcAAJ&pg=PA98#v=onepage&q&f=false "Ueber neue stickstoffhaltige Verbindungen des Naphtalins, über Phtalinsäure und Nitrophtalinsäure"] (On new nitrogenous compounds of naphthalene, on phthalic acid and nitrophthalic acid), ''Annalen der Chemie und Pharmacie'', '''41''' (1) : 98-114; on page 108, Laurent coins the name "Phtalinsäure" (phthalic acid).</ref> 19세기의 제조 방법으로는 질산을 사용한 사염화 나프탈렌의 산화 또는 촉매로 수은 또는 황산 수은(II)를 사용하여 탄화수소를 발연 황산으로 산화시키는 것이 있다.<ref name=EB1911/>

== 합성 ==
나프탈렌이 [[과망가니즈산 칼륨]] 또는 [[중크로뮴산 칼륨]]으로 산화되면 프탈산이 생성된다.

== 반응 및 용도 ==
{|
|[[파일:Phthalic acid.JPG|섬네일|왼쪽|180px|프탈산 결정]]
|}
프탈산은 p''K''<sub>a</sub>가 2.89와 5.51인 이염기산이다. 모노칼륨 염인 [[프탈산수소 칼륨]]은 [[분석화학]]의 표준산이다. 일반적으로 프탈산 에스터는 널리 이용가능한 [[프탈산 무수물]]로부터 제조된다. 물이 있는 상태에서 [[나트륨 아말감]]으로 프탈산을 환원시키면 [[1,3-사이클로헥사다이엔]] 유도체가 생성된다.<ref>{{OrgSynth | author = Richard N. McDonald and Charles E. Reineke | title = trans-1,2-Dihydrophthalic Acid | collvol = 6 | collvolpages = 461 | prep = cv6p0461 | year = 1988}}</ref>

== 안전 ==
프탈산의 독성은 550 mg/kg의 [[반수 치사량|LD<sub>50</sub>]](쥐)로 보통이다.

== 생분해 ==
세균인 ''Pseudomonas'' sp. P1은 프탈산을 분해한다.<ref>{{학위논문 인용|type=Ph.D.|url=http://prr.hec.gov.pk/Thesis/3362H.pdf|first=Muhammad|last=Ishtiaq Ali|title=Microbial degradation of polyvinyl chloride plastics|publisher=Quaid-i-Azam University|year=2011|pages=47|access-date=2022-04-04|archive-date=2013-12-24|archive-url=https://web.archive.org/web/20131224083944/http://prr.hec.gov.pk/Thesis/3362H.pdf|url-status=}}</ref>

== 같이 보기 ==
* [[벤젠다이카복실산]]
* [[1,3-벤젠다이카복실산]] ([[아이소프탈산]])
* [[1,4-벤젠다이카복실산]] ([[테레프탈산]])
* [[프탈레이트]]
* [[프탈산 무수물]]
* [[프탈산수소 칼륨]]: [[산-염기 적정]]을 위한 [[일차 표준 물질]]

== 각주 ==
{{각주}}
* Merck Index, 9th ed, #7178

== 외부 링크 ==
* [http://www.inchem.org/documents/icsc/icsc/eics0768.htm International Chemical Safety Card 0768]

{{전거 통제}}

[[분류:벤조산]]
[[분류:다이카복실산]]