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{{chembox
| Watchedfields = changed
| verifiedrevid = 472035275
|ImageFile=MBBA.svg
|ImageSize=
|IUPACName=N-(4-甲氧基苯亞甲基)-4-丁基苯胺
|OtherNames=
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=97402-82-9
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1=128758-96-3
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2=26227-73-6
| PubChem=33363
| SMILES=CCCCC1=CC=C(C=C1)N=CC2=CC=C(C=C2)OC
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 30817
| InChI = 1/C18H21NO/c1-3-4-5-15-6-10-17(11-7-15)19-14-16-8-12-18(20-2)13-9-16/h6-14H,3-5H2,1-2H3/b19-14+
| InChIKey = FEIWNULTQYHCDN-XMHGGMMEBZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H21NO/c1-3-4-5-15-6-10-17(11-7-15)19-14-16-8-12-18(20-2)13-9-16/h6-14H,3-5H2,1-2H3/b19-14+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FEIWNULTQYHCDN-XMHGGMMESA-N
}}
|Section2={{Chembox Properties
| C = 18 | H = 21 | N = 1 | O = 1
| Appearance=光彩的混濁[[液晶]]
| Density=1.03 g/cm3<ref name="MSDS"/><nowiki></nowiki>{{NewLine|[[凝固點]]|22.5 °C（[[液晶|液晶相]]轉為[[固相]]）|table}}
| MeltingPt=46.987 °C（320.137 K）<nowiki></nowiki>{{NewLine|[[液晶化點]] （[[熔點]]）|22.5 °C（295.65 K）|table}}<nowiki></nowiki>{{NewLine|[[清晰點]]|46.987 °C（[[液晶|液晶相]]轉為[[液相]]）|table}}
| BoilingPt=176 °C<ref name="MSDS">[https://www.spectrumchemical.com/MSDS/TCI-M0275.pdf MBBA MSDS] {{Wayback|url=https://www.spectrumchemical.com/MSDS/TCI-M0275.pdf |date=20131217204525 }} spectrumchemical.com [2013-12-06]</ref><nowiki></nowiki>{{NewLine|[[三相點]]|294.0 K（20.85°C），0.1 kPa|table}}
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| ExternalMSDS = [https://www.spectrumchemical.com/MSDS/TCI-M0275.pdf MSDS]
| wxxfh = {{wxxfh|Xi}}
| RPhrases = {{R36/37/38}}
| SPhrases = {{S37/39}}-{{S26}}
| FlashPt=160 °C <ref name="look-chemical">{{Cite Web|url=http://www.lookchem/N--4-Methoxybenzylidene--4-butylaniline/|title=N-(4-Methoxybenzylidene)-4-butylaniline|archive-url=https://archive.today/20181017193052/https://www.lookchem.com/N--4-Methoxybenzylidene--4-butylaniline/|archive-date=2018-10-17|accessdate=2013-12-06|publisher=lookchem.co<nowiki></nowiki>m|dead-url=yes}}</ref>
| Autoignition=
}}
}}
'''MBBA'''，即'''N-(4-甲氧基苯亞甲基)-4-丁基苯胺'''（{{langx|en|N-(4-Methoxybenzylidene)-4-butylaniline}}），是一種[[有機化合物]]，屬於[[亞胺]]類，含有[[醚]]、[[苯]]、醛亞胺和[[醚]]等[[官能基]]，具有[[液晶]]相態，且[[常溫]]下就呈液晶態<ref>{{Cite web|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=C26227736&Mask=4|title=Phase change data|accessdate=2013-12-05|publisher=webbook.nist.gov|archive-url=https://web.archive.org/web/20181017193829/http://webbook.nist.gov/cgi/cbook.cgi?ID=C26227736&Mask=4|archive-date=2018-10-17|dead-url=yes}} webbook.nist.gov [2013-12-5]</ref>，是一種研究较多的液晶材料，其[[化學式]]為C18H21NO<ref>[http://webbook.nist.gov/cgi/cbook.cgi?InChI=InChI%3D1/C18H21NO/c1-3-4-5-15-6-10-17(11-7-15)19-14-16-8-12-18(20-2)13-9-16/h6-14H%2C3-5H2%2C1-2H3/b19-14%2B%0A MBBA-NIST Webbook] {{Wayback|url=http://webbook.nist.gov/cgi/cbook.cgi?InChI=InChI%3D1%2FC18H21NO%2Fc1-3-4-5-15-6-10-17%2811-7-15%2919-14-16-8-12-18%2820-2%2913-9-16%2Fh6-14H%2C3-5H2%2C1-2H3%2Fb19-14%2B%0A |date=20181017193829 }} webbook.nist.gov [2013-12-5]</ref>。

==性質==
MBBA的在[[常溫]]下為[[液晶]]態，[[凝固點]]為22度<ref name="Shinoda, Maeda, et al., 1974">Shinoda, T.; Maeda, Y.; Enokido, H., Thermodynamic properties of N-(p-methoxybenzylidene)-p-n-butyl-aniline (MBBA) from 2K to its isotropic-liquid phase, J. Chem. Thermodynam., 1974, 6, 921-934.</ref>，[[熔點]]為47度<ref>Shinoda, T.; Mizuno, M., On the pre-transition phenomenon of n-(p-methoxybenzylidene)-p-n-butylaniline (MBBA), Tokyo Kogyo Shikensho Hokoku, 1982, 77(4), 215-217.</ref>，22到47度為液晶相<ref>John Wiley & Sons,Optics of Liquid Crystal Displays Pochi Yeh, Claire Gu ,2010 ,ISBN 0470181761,第16頁</ref><ref>Wiley Series in Pure and Applied Optics第 67 卷, ISSN 0277-2493</ref>。從[[固態]]變成液晶態的相變熱為ΔHtrs=15.9377 kJ/mol、ΔStrs=53.91 k/mol K；從液晶相變成液相的相變熱為ΔHtrs=0.2841 kJ/mol、ΔStrs=0.89 k/mol K<ref name="Shinoda, Maeda, et al., 1974"/>；[[熔化熱]]為ΔHtrs=18.033 kJ/mol、ΔStrs=61.04 k/mol K<ref>Janik, J.A.; Janik, J.M.; Mayer, J.; Sciesinska, E.; Sciesinski, J.; Twardowski, J.; Waluga, T.; Witko, W., Calorimetric and infrared study of the phase situation in solid MBBA [N-(p-methoxybenzylidene)-p-(n-butyl)aniline], J. Phys. (Paris) Colloq., 1975, (1), 159-165.</ref>，[[三相點]]約為[[攝氏]]20度<ref>Janik, J.A.; Janik, J.M.; Mayer, J.; Sciesinska, E.; Sciesinski, J.; Twardowski, J.; Waluga, T.; Witko, W., Calorimetric and infrared study of the phase situation in solid MBBA [N-(p-methoxybenzylidene)-p-(n-butyl)aniline], J. Phys., Colloq., 1975, 1, 159</ref>，另外，固、液、液晶共存為295.3 K，約為22.15 °C<ref>TRC - Thermodynamics Research Center, NIST Boulder Laboratories, M. Frenkel director</ref>。

MBBA不溶於[[水]]、異氰酸酯、鹵代有機物、[[過氧化物]]、[[酚類]]（[[酸性]]）、環氧化物、[[酸酐]]和鹵化物，與氫結合可能生成強還原劑，如氫化物。<ref name="look-chemical"/>

MBBA為長條型[[液晶]][[分子]]，[[常溫]]下會以間列式（線條式，或稱為[[向列型液晶|向列型]]，nematic phase）的方式排列。<ref name="LCY"/>

{| class=wikitable width=480
|- align=center
|MBBA的[[空間填充模型]]
|MBBA的間列式液晶結構
|MBBA於固態、液晶態、液態的可能結構
|- align=center
|[[File:MBBA-3D-vdW.png|160px]]
|[[File:LiquidCrystal-MesogenOrder-Nematic.jpg|160px]]
|[[File:LiquidCrystal-Ordering.jpg|160px]]
|}

==制備==
制備MBBA可由[[茴香醛]]（又稱[[對甲氧基苯甲醛]]）和[[對丁基苯胺]]發生[[縮合反應]]脫去一[[水分子]]製得，即常見的亞胺制備流程，以[[對丁基苯胺]]的[[氮]]上[[孤對電子]]攻擊[[對甲氧基苯甲醛]]的[[羰基]]發生[[親核加成反應]]，得到[[季銨鹽|季銨]][[半縮醛]]，在適當條件轉變為[[半縮醛胺]]中間體，再脫去一[[水分子]]，即發生{{le|烷基亞胺去氧雙取代反應|Alkylimino-de-oxo-bisubstitution}}得到產物MBBA<ref>[[Organic Syntheses]], Coll. Vol. 6, p.901 (1988); Vol. 50, p.66 (1970). [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p0901 Article] {{Wayback|url=http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p0901 |date=20120728092249 }}</ref>。

一般會選用[[苯]]或[[甲苯]]作為[[溶劑]]，因為它們和水都會有[[共沸]]現象，再用[[迪安-斯塔克裝置]]把水從系統中移除或使用[[分子篩]]，使平衡移至MBBA方向以制備MBBA。

1969年，漢斯·克爾克（Hans Kelker）首次成功合成MBBA，是當時少數於室溫下呈間列式液晶相的液晶材料，且成為最熱門的液晶研究的課題之一<ref>{{cite journal| journal=Angew. Chem. Int. Ed.|volume = 8|year =1969| title =A Liquid-crystalline (Nematic) Phase with a Particularly Low Solidification Point| issue =11| doi = 10.1002/anie.196908841| page = 884| last1=Kelker| first1=H.| last2=Scheurle| first2=B.}}</ref>。

== 用途 ==
MBBA被廣泛的應用在各種電子、儀表產品的[[液晶顯示器]]中，但由於MBBA的液晶態範圍較狹窄，僅22度到47度，因此會加入EBBA形成共晶體，該混合物液晶相範圍最廣可達到0度至60度<ref name="LCY">[http://promotion.ep.nctu.edu.tw/teaches/95/95nctu.pdf 液晶顯示器光學] {{Wayback|url=http://promotion.ep.nctu.edu.tw/teaches/95/95nctu.pdf |date=20131211214501 }} promotion.ep.nctu.edu.tw [2013-12-6]</ref>。目前工業上用的是MBBA與EBBA的混合物。

== 參見 ==
*[[液晶]]
*[[EBBA]]

==參考文獻==
{{Reflist}}

[[Category:亚胺]]
[[Category:液晶]]
[[Category:4-甲氧基苯基化合物]]
[[Category:正丁基化合物]]

MBBA - 版本历史

imported>ExultantEditor 来自 2025年12月26日 (五) 16:54