بنزوين

Benzoin
الأسماء
	اسم أيوپاك المفضل 2-Hydroxy-1,2-diphenylethan-1-one
	أسماء أخرى 2-Hydroxy-2-phenylacetophenone; 2-Hydroxy-1,2-diphenylethanone; Desyl alcohol; Bitter almond oil camphor
المُعرِّفات
رقم CAS
3D model (JSmol)	Interactive image; Interactive image;
3DMet	B00286;
مرجع بايلستاين	391839
ChEBI	CHEBI:17682 ;
ChEMBL	ChEMBL190677 ;
ChemSpider	8093 ;
ECHA InfoCard	100.003.938
KEGG	C01408 ;
PubChem CID	8400;
رقم RTECS	DI1590000;
UNII	L7J6A1NE81 ;
CompTox Dashboard (EPA)	DTXSID1020144 ;
	InChI InChI=1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H Key: ISAOCJYIOMOJEB-UHFFFAOYSA-N ; InChI=1/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H Key: ISAOCJYIOMOJEB-UHFFFAOYAO;
	SMILES O=C(c1ccccc1)C(O)c2ccccc2; c1ccc(cc1)C(C(=O)c2ccccc2)O;
الخصائص
الصيغة الجزيئية	C14H12O2
كتلة مولية	212.23 g mol-1
المظهر	Off-white crystals
الكثافة	1.310 g/cm3 (20 °C)
نقطة الانصهار
نقطة الغليان
قابلية الذوبان في الماء	Slightly soluble
قابلية الذوبان في ethanol	Very good
قابلية الذوبان في ether	Slightly soluble
قابلية الذوبان في chlorine	Soluble
قابلية الذوبان في chloroform	Very good
المخاطر
ن.م.ع. عبارات المخاطر	H412
ن.م.ع. العبارات الاحتياطية	P273, P501
NFPA 704 (معيـَّن النار)	1 1 0
	الجرعة أو التركيز القاتل (LD, LC):
LD50 (الجرعة الوسطى)	10.000 mg/kg
	ما لم يُذكر غير ذلك، البيانات المعطاة للمواد في حالاتهم العيارية (عند 25 °س [77 °ف]، 100 kPa).
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	مراجع الجدول

البنزوين Benzoin هو مركب عضوي يتكون من الإيثيلين الذي يربط بين الفينيل الهيدروكسيل والكيتون. It appears as off-white crystals, with a light camphor-like odor. Benzoin is synthesized from benzaldehyde in the benzoin condensation. It is chiral and it exists as a pair of enantiomers: (R)-benzoin and (S)-benzoin.

ولا يدخل البنزوين في تكوين الراتينج بنزويني المستخرج من الأشجار البنزوينية (الأصطركيات) حيث أن المادة المكونة لها هي حمض البنزويك.

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تاريخ

Benzoin was first reported in 1832 by Justus von Liebig and Friedrich Woehler during their research on oil of bitter almond, which is benzaldehyde with traces of hydrocyanic acid.^[2] The catalytic synthesis by the benzoin condensation was improved by Nikolay Zinin during his time with Liebig.^[3]^[4]

الاستخدامات

The main use of benzoin is as a precursor to benzil, which is used as a photoinitiator.^[5]^[6] The conversion proceeds by organic oxidation using copper(II),^[7] nitric acid, or oxone. In one study, this reaction is carried out with atmospheric oxygen and basic alumina in dichloromethane.^[8]

Benzoin also sees wide spread use in powder coating formulations, where it acts as a degassing agent during the curing stage. This action prevents surface defects such as 'pinholing'.^[9]^[10]

Benzoin can be used in the preparation of several pharmaceutical drugs including oxaprozin, ditazole, and phenytoin.^[11]

التحضير

Benzoin is prepared from benzaldehyde via the benzoin condensation.^[12]

المصادر

^ ^أ ^ب ^ت ^ث ^ج William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. p. 3-40. ISBN 978-1-4987-5429-3.
^ Wöhler, Liebig; Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie. 3 (3): 249–282. doi:10.1002/jlac.18320030302. hdl:2027/hvd.hxdg3f.
^ N. Zinin (1839). "Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe". Annalen der Pharmacie. 31 (3): 329–332. doi:10.1002/jlac.18390310312. Archived from the original on 2022-07-09. Retrieved 2020-09-10.
^ N. Zinin (1840). "Ueber einige Zersetzungsprodukte des Bittermandelöls". Annalen der Pharmacie. 34 (2): 186–192. doi:10.1002/jlac.18400340205. Archived from the original on 2022-07-09. Retrieved 2019-06-30.
^ Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, 2002 by Wiley-VCH, Wienheim. DOI:10.1002/14356007.a15_077
^ Nakamura, Kenichiro (2015). Photopolymers : photoresist materials, processes, and applications. Boca Raton, FL. ISBN 978-1-4665-1731-8. OCLC 884012539.{{cite book}}: CS1 maint: location missing publisher (link)
^ قالب:OrgSynth
^ Konstantinos Skobridis; Vassiliki Theodorou; Edwin Weber (2006). "A very simple and chemoselective air oxidation of benzoins to benzils using alumina". Arkivoc. 06-1798JP: 102–106.^{[dead link]}
^ Maxwell, B.E; Wilson, R.C; Taylor, H.A; Williams, D.E; Farnham, W; Tria, J (November 2001). "Understanding benzoin's mode of action in powder coatings". Progress in Organic Coatings. 43 (1–3): 158–166. doi:10.1016/S0300-9440(01)00181-3.
^ Jahromi, Shahab; Mostert, Ben; Derks, Andreas; Koldijk, Fokelien (December 2003). "Mechanism of action of benzoin as a degassing agent in powder coatings". Progress in Organic Coatings. 48 (2–4): 183–193. doi:10.1016/S0300-9440(03)00096-1.
^ U.S. Patent 2٬242٬775
^ قالب:OrgSynth

وصلات خارجية

Benzoin synthesis, Organic Syntheses, Coll. Vol. 1, p.94 (1941); Vol. 1, p.33 (1921)

[crc97-1] أ ^ب ^ت ^ث ^ج William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. p. 3-40. ISBN 978-1-4987-5429-3.

[2] Wöhler, Liebig; Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie. 3 (3): 249–282. doi:10.1002/jlac.18320030302. hdl:2027/hvd.hxdg3f.

[3] N. Zinin (1839). "Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe". Annalen der Pharmacie. 31 (3): 329–332. doi:10.1002/jlac.18390310312. Archived from the original on 2022-07-09. Retrieved 2020-09-10.

[4] N. Zinin (1840). "Ueber einige Zersetzungsprodukte des Bittermandelöls". Annalen der Pharmacie. 34 (2): 186–192. doi:10.1002/jlac.18400340205. Archived from the original on 2022-07-09. Retrieved 2019-06-30.

[Ullmann-5] Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, 2002 by Wiley-VCH, Wienheim. DOI:10.1002/14356007.a15_077

[6] Nakamura, Kenichiro (2015). Photopolymers : photoresist materials, processes, and applications. Boca Raton, FL. ISBN 978-1-4665-1731-8. OCLC 884012539.{{cite book}}: CS1 maint: location missing publisher (link)

[7] قالب:OrgSynth

[8] Konstantinos Skobridis; Vassiliki Theodorou; Edwin Weber (2006). "A very simple and chemoselective air oxidation of benzoins to benzils using alumina". Arkivoc. 06-1798JP: 102–106.^{[dead link]}

[9] Maxwell, B.E; Wilson, R.C; Taylor, H.A; Williams, D.E; Farnham, W; Tria, J (November 2001). "Understanding benzoin's mode of action in powder coatings". Progress in Organic Coatings. 43 (1–3): 158–166. doi:10.1016/S0300-9440(01)00181-3.

[10] Jahromi, Shahab; Mostert, Ben; Derks, Andreas; Koldijk, Fokelien (December 2003). "Mechanism of action of benzoin as a degassing agent in powder coatings". Progress in Organic Coatings. 48 (2–4): 183–193. doi:10.1016/S0300-9440(03)00096-1.

[11] U.S. Patent 2٬242٬775

[12] قالب:OrgSynth

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