كومين Cumene

Cumene
الأسماء
	اسم أيوپاك المفضل (Propan-2-yl)benzene
	أسماء أخرى Isopropylbenzene; Cumol; (1-Methylethyl)benzene;
المُعرِّفات
رقم CAS
3D model (JSmol)	Interactive image;
مرجع بايلستاين	1236613
ChEBI	CHEBI:34656 ;
ChEMBL	ChEMBL1398949;
ChemSpider	7128 ;
ECHA InfoCard	100.002.458
رقم EC	202-704-5;
KEGG	C14396 ;
PubChem CID	7406;
رقم RTECS	GR8575000;
UNII	8Q54S3XE7K ;
UN number	1918
CompTox Dashboard (EPA)	DTXSID1021827 ;
	InChI InChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3 Key: RWGFKTVRMDUZSP-UHFFFAOYSA-N ; InChI=1/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3 Key: RWGFKTVRMDUZSP-UHFFFAOYAJ;
	SMILES CC(C)c1ccccc1;
الخصائص
الصيغة الجزيئية	C9H12
كتلة مولية	120.19 g mol-1
المظهر	Colorless liquid
الرائحة	Sharp, gasoline-like
الكثافة	0.862 g cm−3, liquid
نقطة الانصهار
نقطة الغليان
قابلية الذوبان في الماء	negligible
قابلية الذوبان	soluble in acetone, ether, ethanol
ضغط البخار	4.5 mmHg (25 °C)
القابلية المغناطيسية	-89.53·10−6 cm3/mol
معامل الانكسار (nD)	1.4915 (20 °C)
اللزوجة	0.777 cP (21 °C)
المخاطر
خطر رئيسي	flammable
ن.م.ع. مخطط تصويري
ن.م.ع. كلمة الاشارة	Warning
ن.م.ع. عبارات المخاطر	H226, H302, H304, H312, H314, H332, H335, H341, H412, H441
ن.م.ع. العبارات الاحتياطية	P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P322, P330, P363, P405, P501
NFPA 704 (معيـَّن النار)	3 2 1
نقطة الوميض	43 °C (109 °F; 316 K)
درجة حرارة; الاشتعال الذاتي	424 °C (795 °F; 697 K)
حدود الانفجار	0.9-6.5%
	الجرعة أو التركيز القاتل (LD, LC):
LD50 (الجرعة الوسطى)	12750 mg/kg (oral, mouse); 1400 mg/kg (oral, rat)
LC50 (التركيز الأوسط)	200 ppm (mouse, 7 hr)
LCLo (المنشورة الأقل)	8000 ppm (rat, 4 hr)
	حدود التعرض الصحية بالولايات المتحدة (NIOSH):
PEL (المسموح)	TWA 50 ppm (245 mg/m3) [skin]
REL (الموصى به)	TWA 50 ppm (245 mg/m3) [skin]
IDLH (خطر عاجل)	900 ppm
مركبات ذا علاقة
مركـّبات ذات علاقة	ethylbenzene; toluene; benzene
	ما لم يُذكر غير ذلك، البيانات المعطاة للمواد في حالاتهم العيارية (عند 25 °س [77 °ف]، 100 kPa).
	verify (what is ?)
	مراجع الجدول

Cumene (isopropylbenzene) is an organic compound that contains a benzene ring with an isopropyl substituent. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C. Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals, primarily phenol and acetone (known as the cumene process).

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الانتاج

Commercial production of cumene is by Friedel–Crafts alkylation of benzene with propylene. The original route for manufacturing of cumene was by alkylation of benzene in the liquid phase using sulfuric acid as a catalyst, but because of the complicated neutralization and recycling steps required, together with corrosion problems, this process has been largely replaced. As an alternative, solid phosphoric acid (SPA) supported on alumina has been used as the catalyst.

Since the mid-1990s, commercial production has switched to zeolite-based catalysts. In this process, the efficiency of cumene production is generally 70-75%. The remaining components are primarily polyisopropyl benzenes. In 1976, an improved cumene process that uses aluminum chloride as a catalyst was developed. The overall conversion of cumene for this process can be as high as 90%.

The addition of two equivalents of propylene gives diisopropylbenzene (DIPB). Using transalkylation, DIPB is comproportionated with benzene to give cumene.^[5]

Autoxidation

Depending on the conditions, autoxidation of cumene gives dicumyl peroxide or cumene hydroperoxide. Both reactions exploit the weakness of the tertiary C-H bond. The tendency of cumene to form peroxides by autoxidation poses safety concerns.^[6] Tests for peroxides are routinely conducted before heating or distilling.

التطبيقات

Cumene is frequently found as an ingredient in thread locking fluids.^[7]^[8] Cumene is also a precursor chemical to the herbicide isoproturon.^[9]

انظر أيضاً

Pseudocumene

المراجع

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 139, 597. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis. 1989.
^ ^أ ^ب ^ت NIOSH Pocket Guide to Chemical Hazards 0159
^ ^أ ^ب ^ت "Cumene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Bipin V. Vora; Joseph A. Kocal; Paul T. Barger; Robert J. Schmidt; James A. Johnson (2003). "Alkylation". Kirk-Othmer Encyclopedia of Chemical Technology. Kirk‐Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0112112508011313.a01.pub2. ISBN 0471238961.
^ CDC - NIOSH Pocket Guide to Chemical Hazards
^ "LOCTITE 242 MS TL Safety Data Sheet".
^ "Wurth Blue Thread Locker Safety Data Sheet" (PDF).
^ Unger, Thomas A. (1996). Pesticide synthesis handbook (1st ed.). Noyes Publications. p. 239.

وصلات خارجية

[1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 139, 597. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[2] Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis. 1989.

[PGCH-3] أ ^ب ^ت NIOSH Pocket Guide to Chemical Hazards 0159

[IDLH-4] أ ^ب ^ت "Cumene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[5] Bipin V. Vora; Joseph A. Kocal; Paul T. Barger; Robert J. Schmidt; James A. Johnson (2003). "Alkylation". Kirk-Othmer Encyclopedia of Chemical Technology. Kirk‐Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0112112508011313.a01.pub2. ISBN 0471238961.

[6] CDC - NIOSH Pocket Guide to Chemical Hazards

[7] "LOCTITE 242 MS TL Safety Data Sheet".

[8] "Wurth Blue Thread Locker Safety Data Sheet" (PDF).

[9] Unger, Thomas A. (1996). Pesticide synthesis handbook (1st ed.). Noyes Publications. p. 239.

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