{{위키데이터 속성 추적}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 443491626
| Reference =<ref>''[[Merck Index]]'', 11th Edition, '''5991'''.</ref>
| Name = 메틸 에틸 케톤<br />MEK
| ImageFile = Butanone-skeletal-structure.svg
| ImageSize = 160px
| ImageName = MEK의 골격 구조식
| ImageFileL1 = Butanone-3D-balls.png
| ImageNameL1 = MEK의 3차원 구-막대 모형
| ImageFileR1 = Butanone-3D-vdW.png
| ImageNameR1 = MEK의 3차원 공간 충전 모형
| ImageFile2 = Methyl ethyl ketone 45ml.jpg
| ImageName2 = 투명한 병에 담긴 MEK
| PIN = Butan-2-one<ref name=iupac2013>{{서적 인용| title =  Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 725 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| OtherNames = {{ubl
 | 2-뷰탄온 (2-Butanone)
 | 에틸 메틸 케톤 (Ethyl methyl ketone<ref name=iupac2013 /> / Ethylmethylketone)
 | 메틸 에틸 케톤 (Methyl ethyl ketone; MEK; 더 이상 인정되지 않는 명칭<ref name=iupac2013 />)
 | 메틸프로판온 (Methylpropanone)
 | 메틸아세톤 (Methylacetone)
 }}
| IUPACName = 
| Section1 = {{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28398
| SMILES = O=C(C)CC
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 15849
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6321
| PubChem = 6569
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6PT9KLV9IO
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C02845
| InChI = 1/C4H8O/c1-3-4(2)5/h3H2,1-2H3
| InChIKey = ZWEHNKRNPOVVGH-UHFFFAOYAW
| SMILES1 = CCC(=O)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZWEHNKRNPOVVGH-UHFFFAOYSA-N
| CASNo = 78-93-3
| CASNo_Ref = {{cascite|correct|CAS}}
| RTECS = EL6475000
| Gmelin = 25656
| Beilstein = 741880
  }}
| Section2 = {{Chembox Properties
| C=4 | H=8 | O=1
| Appearance = 무색 투명한 액체
| Odor = 박하향 또는 아세톤과 비슷한 냄새<ref name=PGCH/>
| Density = 0.8050{{nbsp}}g/mL
| Solubility = 27.5{{nbsp}}g/100{{thinsp}}mL
| MeltingPtC = −86
| BoilingPtC = 79.64
| pKa = 14.7
| Viscosity = 0.43{{nbsp}}[[Poise (unit)|cP]]
| RefractIndex = 1.37880
| VaporPressure = 78{{nbsp}}mmHg (20{{nbsp}}°C)<ref name=PGCH/>
| MagSus = −45.58·10<sup>−6</sup> cm<sup>3</sup>/mol
| LogP = 0.37<ref name="chemsrc">{{웹 인용|url=https://www.chemsrc.com/en/cas/78-93-3_1101392.html|title=butan-2-one_msds}}</ref>
  }}
| Section3 = {{Chembox Structure
| MolShape =
| Dipole = 2.76{{nbsp}}[[Debye|D]]
  }}
| Section4 = 
| Section5 = 
| Section6 = 
| Section7 = {{Chembox Hazards
| ExternalSDS = [https://web.archive.org/web/20180417143435/http://www.kleanstrip.com/uploads/documents/GME71_SDS-1635.4.pdf Safety Data Sheet]
| GHSPictograms = {{GHS02}}{{GHS07}}<ref name="SDS" />
| GHSSignalWord = '''Danger'''<ref name="SDS" />
| HPhrases = {{H-phrases|225|319|336}}<ref name="SDS">{{웹 인용|title=Safety Data Sheet - Klean Strip - Methyl Ethyl Ketone (MEK) |url=http://www.kleanstrip.com/uploads/documents/GME71_SDS-1635.4.pdf |website=Kleanstrip.com |publisher=Klean Strip |accessdate=5 November 2019 |archiveurl=https://web.archive.org/web/20180417143435/http://www.kleanstrip.com/uploads/documents/GME71_SDS-1635.4.pdf |archivedate=17 April 2018 |language=English |date=15 April 2015}}</ref>
| PPhrases = {{P-phrases|233|210|280|240|241|243|242|264|261|271|370+378|303+361+353|305+351+338|337+313|304+340|312|403+235|501|403+233|405}}<ref name="SDS" />
| NFPA-H = 1
| NFPA-F = 3
| NFPA-R = 0
| FlashPtC = −9
| AutoignitionPtC = 505
| LD50 = {{ubl
 | 2737{{nbsp}}mg/kg (oral, rat)
 | 4050{{nbsp}}mg/kg (oral, mouse)<ref name=IDLH/>
 }}
| PEL = TWA 200{{nbsp}}ppm (590{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0069}}</ref>
| ExploLimits = 1.4–11.4%<ref name=PGCH/>
| IDLH = 3000{{nbsp}}ppm<ref name=PGCH/>
| REL = TWA 200{{nbsp}}ppm (590{{nbsp}}mg/m<sup>3</sup>) ST 300{{nbsp}}ppm (885{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH/>
| LC50 = {{ubl
 | 12667{{nbsp}}ppm (mammal)
 | 13333{{nbsp}}ppm (mouse, 2{{nbsp}}hr)
 | 7833{{nbsp}}ppm (rat, 8{{nbsp}}hr)<ref name=IDLH>{{IDLH|78933|2-Butanone}}</ref>
 }}
  }}
| Section8 = {{Chembox Related
| OtherFunction_label = [[케톤]]
| OtherFunction = [[아세톤]]; [[3-펜탄온]]; [[3-메틸뷰탄온]]
  }}
}}


'''2-뷰탄온''' ('''2-Butanone'''), '''뷰탄온''' ('''Butanone''') 혹은 '''메틸 에틸 케톤''' ('''Methyl Ethyl Ketone''', '''MEK''')은 CH₃C(O)CH₂CH₃의 구조로 이루어진 [[유기화합물]]이다. [[국제 순수·응용 화학 연합|IUPAC]]에서는 메틸 에틸 케톤이라는 이름을 더 이상 사용하지 않고 '''에틸 메틸 케톤''' ('''Ethyl Methyl Ketone''', '''EMK''')으로 사용할 것을 권장하나, [[대한민국 정부]] 및 민간에서는 여전히 메틸 에틸 케톤이 주 명칭으로 사용되고 있다.

성상은 무색 투명하고, 달콤한 냄새를 풍기며, 상온에서 [[액체]]로 있으나 휘발성이 강하고, 물에 약간의 용해성을 띈다. 산업용으로 대량 생산되지만 자연계에서는 미량만 존재한다.<ref name=Ullmann>Wilhelm Neier, Guenter Strehlke "2-Butanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002.</ref> 이성질체로 [[테트라하이드로퓨란]]이 있다.

== 제법 ==
MEK는 [[뷰탄올|2-뷰탄올]]을 [[산화]]시켜 얻을 수 있다. 2-뷰탄올의 [[탈수소화 반응|탈수소화]]에는 [[구리]], [[아연]], [[청동]] 등을 촉매로 사용한다.

:CH<sub>3</sub>CH(OH)CH<sub>2</sub>CH<sub>3</sub>   →   CH<sub>3</sub>C(O)CH<sub>2</sub>CH<sub>3</sub>  +  H<sub>2</sub>

위 제법은 연간 약 7×10^8 kg을 생산하는 데 쓰인다. 이 외에도 [[뷰텐|2-뷰틸렌]]의 [[:en:Wacker process|와커 산화]]나 [[아이소뷰틸벤젠]]의 산화 등 [[아세톤]]의 공업적 제법과 비슷한 방법들이 시도되었으나 실용화되지는 않았다.<ref name=Ullmann/> 페놀 및 아세톤을 생산하는 [[:en:Cumene process|큐멘 공정]]을 수정하여 페놀 및 MEK와 아세톤의 혼합물을 생산할 수도 있다.<ref name=cumeneprocess>{{웹 인용|url=http://www.chemistry.org/portal/a/c/s/1/feature_pro.html?id=c373e908e6e847ac8f6a17245d830100 |title=Archived copy |access-date=2017-12-13 |archive-url=https://web.archive.org/web/20070409042033/http://www.chemistry.org/portal/a/c/s/1/feature_pro.html?id=c373e908e6e847ac8f6a17245d830100# |archive-date=2007-04-09 |url-status=dead }}</ref> 또한 [[:en:Fischer-Tropsch process|피셔-트롭슈 공정]] 반응이나 중질 [[나프타]]의 액상 산화에서 나오는 혼합 산소화물 (Oxygenates)을 분별 처리하여 MEK를 추출하기도 한다.<ref>Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, {{ISBN|978-0-9522674-3-0}}, pages 6013-4</ref>

== 이용 ==
=== [[용제]]로서 ===
MEK는 효과적이고 흔한 용제로, [[고무]], [[레진]], [[아세트산셀룰로스|초산면]], [[나이트로셀룰로스|질화면]] 코팅 및 비닐 필름 공정에 사용된다. 이로 인해 플라스틱 및 [[직물]] 생산, 파라핀 왁스 제조, [[라커]], [[바니시]], 페인트 리무버 등의 가정용 제품, [[변성 에탄올]]의 [[변성제]], [[풀]], 세척제 등으로 사용되며, 지워지는 염료의 용제로써 화이트보드용 마커에도 사용된다. 아세톤과 비교했을 때 유사한 성상을 지녔으나 [[끓는점]]이 더 높고 증발 속도가 더 느리며,<ref name="Fairhall">{{서적 인용| last = Fairhall| first = Lawrence T.| authorlink =| title = Industrial Toxicology| publisher = The Williams and Wilkins Company| year = 1957| location = Baltimore| pages = 172–173| url =| doi =| id =| isbn = }}</ref> 아세톤과는 달리 물과 섞였을 때 [[불변 끓음 혼합물|아제오트로프]]를 만들기 때문에<ref name="Langes">''Lange's Handbook of Chemistry'', 10th ed. pp1496-1505</ref><ref name="crc">''CRC Handbook of Chemistry and Physics'', 44th ed. pp 2143-2184</ref> 여러 용도에서 수분의 아제오트로프 증류가 용이하다.

=== 플라스틱 접합제로서 ===
MEK가 [[폴리스타이렌]]을 비롯한 여러 플라스틱을 녹이는 특성을 이용하여, [[축소모형]]류에서 부품들 간 연결에 사용되는 일명 '프라모델용 시멘트'로 시판되기도 하는데, 이는 접착제가 아닌 접합제이다.

=== 그 외 용도 ===
MEK는 중합 반응의 촉매인 메틸 에틸 케톤 퍼옥사이드 (Methyl Ethyl Ketone Peroxide 과산화 메틸 에틸 케톤, MEKP)의 전구체이기도 하다.

[[다이메틸글라이옥심]] 조제 시 MEK를 질산에틸과 반응시킨 후 다이옥심으로 치환하는 과정을 사용할 수 있다.<ref>{{OrgSynth | author = Semon, W. L.; Damerell, V. R. | title = Dimethylglyoxime | collvol = 2 | collvolpages = 204 | year = 1943 | prep = cv2p0204}}</ref>

:[[파일:Preparation_of_dimethylglyoxime.png|400px]]

[[하이드라진]] 생산에 있어서도 과산화 과정에서 MEK가 사용된다. 이 때 MEK는 원하는 히드라진을 생산한 후 마지막 과정에서 재생성된다.

:[[파일:Pechiney-Ugine-Kuhlmann process.png|506px]]

== 안전성 ==
=== 인화성 ===
MEK는 대부분의 산화재와 반응하여 불을 일으킬 수 있다. 중간 수준의 폭발성을 지녀 소량의 불 또는 스파크에도 격렬한 반응이 일어난다. MEK로 인한 화재의 진화에는 [[이산화탄소]], 건조사 등의 건식 소화재, 항알코올성 포소화재를 사용하여야 한다. 증기가 인화 농도만큼 공기 중에 있을 경우 [[인간]]은 증기의 자극성으로 인해 불편감을 느낀다.<ref name="Fairhall"/>

=== 건강 영향 ===
MEK는 인간의 [[눈 (기관)|눈]]과 [[코]]에 자극을 초래한다. 또한 [[담배]] 연기의 구성 성분이기도 하다.<ref name="TalhoutSchulz2011">{{저널 인용|last1=Talhout|first1=Reinskje|last2=Schulz|first2=Thomas|last3=Florek|first3=Ewa|last4=Van Benthem|first4=Jan|last5=Wester|first5=Piet|last6=Opperhuizen|first6=Antoon|title=Hazardous Compounds in Tobacco Smoke|journal=International Journal of Environmental Research and Public Health|volume=8|issue=12|year=2011|pages=613–628|issn=1660-4601|doi=10.3390/ijerph8020613|pmid=21556207|pmc=3084482}}</ref> 동물 실험에서 심각한 건강 영향은 매우 높은 농도에서만 관찰되었는데, 실례로 [[마우스]]에서 고농도 노출 시 (시험조건 일 7시간씩 3000ppm) 골격 기형아 및 저체중아 출산이 관찰된 바 있으나,<ref>{{저널 인용| author = Schwetz | year = 1991 | journal = Fundam. Appl. Toxicol. | volume = 16 | issue = 4 | pages = 742–748 | doi = 10.1016/0272-0590(91)90160-6 | pmid = 1884913 | title = Developmental toxicity of inhaled methyl ethyl ketone in Swiss mice|display-authors=etal| url = https://zenodo.org/record/1258441 }}</ref> 동물의 경구 또는 호흡에서 [[발암성]]이 관찰된 사례 및 장기적인 연구는 보고된 바 없다.<ref name=iris>{{웹 인용|title=Methyl ethyl ketone (MEK) (CASRN 78-93-3)|url=http://www.epa.gov/iris/subst/0071.htm|website=Integrated Risk Information System (IRIS)|publisher=EPA|accessdate=16 March 2015|date=26 September 2003}}</ref><ref name=tox>{{웹 인용|title=U.S.Toxicological review of Methyl ethyl ketone In Support of Summary Information on the Integrated Risk Information System (IRIS)|date= September 2003|url=http://www.epa.gov/iris/toxreviews/0071tr.pdf|publisher=U.S. Environmental Protection Agency|accessdate=16 March 2015|pages=152}}</ref>

다른 용제의 독성을 강화한다는 연구가 있다. 이 연구 결과에 따르면 MEK는 다른 용제와 혼합·노출하였을 때 단순히 독성 수준을 합한 것보다 더 독성이 큰 것으로 알려졌다.<ref>F D Dick. [https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2078137/ Solvent neurotoxicity], Occup Environ Med. 2006 Mar; 63(3): 221–226. {{doi|10.1136/oem.2005.022400}}, {{PMC|2078137}}</ref>

또한 [[마약 및 향정신성물질의 불법거래방지에 관한 국제연합협약]]의 표 2 전구체에 등재되어 있으며, 대한민국에서도 [[마약류 관리에 관한 법률]] 및 동법 시행령에서 마약류 원료물질로 등록되어 있다.

=== 규제 현황 ===
MEK는 지상에서 [[오존]] 생성에 기여하는 [[휘발성 유기화합물]]인 탓에 [[미국 환경보호청]]의 유해대기오염물질로 지정되었다가 2005년 지정 해제되었으며, 대한민국에서는 제4류 [[위험물]]이면서 동시에 [[유해화학물질]]인 물질로 지정되어 있다.

== 같이 보기 ==
* [[뷰티르알데하이드]]
* [[뷰테인]]
== 각주 ==
<references />

== 외부 링크 ==
* {{위키공용분류-줄|Butanone}}

{{전거 통제}}

[[분류:케톤]]
[[분류:용매]]
[[분류:공해]]
[[분류:달콤한 냄새가 나는 화학 물질]]