هيكسان

يجب ألا يـُخلـَط بينها وبين hexene or hexyne.
هيكسان
Skeletal formula of hexane
Skeletal formula of hexane with all implicit carbons shown, and all explicit hydrogens added
Ball and stick model of hexane
Spacefill model of hexane
الأسماء
اسم أيوپاك المفضل
Hexane[2]
أسماء أخرى
Sextane,[1] hexacarbane
Identifiers
رقم CAS
3D model (JSmol)
مرجع بايلستاين 1730733
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.435 Edit this at Wikidata
رقم EC
  • 203-777-6
مرجع Gmelin 1985
KEGG
عناوين مواضيع طبية MeSH {{{value}}}
رقم RTECS
  • MN9275000
UNII
UN number 1208
InChI InChI={{{value}}}
SMILES
الخصائص
الصيغة الجزيئية C6H14
كتلة مولية 86.18 g mol-1
المظهر Colorless liquid
الرائحة Petrolic
الكثافة 0.6606 g mL−1[3]
نقطة الانصهار
نقطة الغليان
قابلية الذوبان في الماء 9.5 mg L−1
log P 3.764
ضغط البخار 17.60 kPa (at 20.0 °C)
kH 7.6 nmol Pa−1 kg−1
λmax 200 nm
القابلية المغناطيسية −74.6·10−6 cm3/mol
معامل الانكسار (nD) 1.375
اللزوجة 0.3 mPa·s
Dipole moment 0.08 D
الكيمياء الحرارية
الإنتالپية المعيارية
للتشكل ΔfHo298 		−199.4–−198.0 kJ mol−1
الانتالبية المعيارية
للاحتراق ΔcHo298 		−4180–−4140 kJ mol−1
Standard molar
entropy So298 		296.06 J K−1 mol−1
سعة الحرارة النوعية، C 265.2 J K−1 mol−1
المخاطر
خطر رئيسي Reproductive toxicity – After aspiration, pulmonary oedema, pneumonitis[4]
ن.م.ع. مخطط تصويري الرمز التصويري للهب في النظام المنسق عالمياً لتصنيف وعنونة الكيماويات (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) رمز الخطر على الصحة في النظام المنسق عالمياً لتصنيف وعنونة الكيماويات (GHS) رمز البيئة في النظام المنسق عالمياً لتصنيف وعنونة الكيماويات (GHS)
ن.م.ع. كلمة الاشارة DANGER
H225, H302, H305, H315, H336, H361fd, H373, H411
P201, P202, P210, P233, P235, P240, P241, P242, P243, P260, P264, P271, P273, P280, P281, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P308+P313, P310, P312, P314, P332+P313, P363, P370+P378, P391, P403+P233, P405, P501
NFPA 704 (معيـَّن النار)
Flammability code 3: سوائل ومواد صلبة يمكن اشتعالها تقريباً تحت ظروف أي درجة حرارة محيطة. نقطة الوميض بين 23 و 38 °س (73 و 100 °ف). مثل الگاسولينHealth code 1: التعرض سيتسبب في تهيجاً ولكن لا يترك سوى جروح طفيفة باقية. مثل زيت الترپنتينReactivity code 0: مستقر في العادة، حتى تحت ظروف التعرض للنار، ولا يتفاعل مع الماء. مثل النيتروجين السائلSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
1
0
نقطة الوميض −26.0 °C (−14.8 °F; 247.2 K)
234.0 °C (453.2 °F; 507.1 K)
حدود الانفجار 1.2–7.7%
الجرعة أو التركيز القاتل (LD, LC):
25 g kg−1 (oral, rat)
28710 mg/kg (rat, oral)[6]
56137 mg/kg (rat, oral)[6]
حدود التعرض الصحية بالولايات المتحدة (NIOSH):
PEL (المسموح)
 TWA 500 ppm (1800 mg/m3)[5]
REL (الموصى به)
 TWA 50 ppm (180 mg/m3)[5]
IDLH (خطر عاجل)
 1100 ppm[5]
مركبات ذا علاقة
alkanes ذات العلاقة
ما لم يُذكر غير ذلك، البيانات المعطاة للمواد في حالاتهم العيارية (عند 25 °س [77 °ف]، 100 kPa).
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مراجع الجدول

الهكسان هو من الهيدروكربونات. كما أن الهكسان ألكان له الصيغة الكيميائية CH3(CH2)4CH3. البادئة "هكس" ترجع إلى وجود 6 ذرات كربون, بينما اللاحقة "ان" تدل على أن الرابطة أحادية بين ذرات الكربون. متزامرات (isomer) الهكسان غير نشطة, ولذا غالبا ما تستخدم كمذيب خامل في التفاعلات العذوية لأنها غير قطبية. كما أنهم من المركبات الشائعة في الالجازولين.

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

Isomers

المقالة الرئيسية: C6H14
Common name IUPAC name Text formula Skeletal formula
normal hexane
n-hexane 		hexane CH3(CH2)4CH3 Hexane-2D-Skeletal.svg
isohexane 2-methylpentane (CH3)2CH(CH2)2CH3 2-metilpentāns.svg
3-methylpentane CH3CH2CH(CH3)CH2CH3 3-metilpentāns.svg
2,3-dimethylbutane (CH3)2CHCH(CH3)2 2,3-dimetilbutāns.svg
neohexane 2,2-dimethylbutane (CH3)3CCH2CH3 2,2-dimetilbutāns.svg


Uses

In industry, hexanes are used in the formulation of glues for shoes, leather products, and roofing. They are also used to extract cooking oils (such as canola oil or soy oil) from seeds, for cleansing and degreasing a variety of items, and in textile manufacturing. They are commonly used in food based soybean oil extraction in the United States, and are potentially present as contaminants in all soy food products in which the technique is used[بحاجة لمصدر]; the lack of regulation by the FDA of this contaminant is a matter of some controversy.[7][8]

A typical laboratory use of hexanes is to extract oil and grease contaminants from water and soil for analysis.[9] Since hexane cannot be easily deprotonated, it is used in the laboratory for reactions that involve very strong bases, such as the preparation of organolithiums. For example, butyllithiums are typically supplied as a hexane solution.[10]

Hexanes are commonly used in chromatography as a non-polar solvent. Higher alkanes present as impurities in hexanes have similar retention times as the solvent, meaning that fractions containing hexane will also contain these impurities. In preparative chromatography, concentration of a large volume of hexanes can result in a sample that is appreciably contaminated by alkanes. This may result in a solid compound being obtained as an oil and the alkanes may interfere with analysis.[11]

Production

Hexanes are chiefly obtained by refining crude oil. The exact composition of the fraction depends largely on the source of the oil (crude or reformed) and the constraints of the refining. The industrial product (usually around 50% by weight of the straight-chain isomer) is the fraction boiling at 65–70 °C (149–158 °F).

Physical properties

All alkanes are colorless.[12][13] The boiling points of the various hexanes are somewhat similar and, as for other alkanes, are generally lower for the more branched forms. The melting points are quite different and the trend is not apparent.[14]

Isomer M.P. (°C) M.P. (°F) B.P. (°C) B.P. (°F)
n-hexane −95.3 −139.5 68.7 155.7
3-methylpentane −118.0 −180.4 63.3 145.9
2-methylpentane (isohexane) −153.7 −244.7 60.3 140.5
2,3-dimethylbutane −128.6 −199.5 58.0 136.4
2,2-dimethylbutane (neohexane) −99.8 −147.6 49.7 121.5

Hexane has considerable vapor pressure at room temperature:

Temperature (°C) Temperature (°F) Vapor pressure (mmHg) Vapor pressure (kPa)
−40 −40 3.36 0.448
−30 −22 7.12 0.949
−20 −4 14.01 1.868
−10 14 25.91 3.454
0 32 45.37 6.049
10 50 75.74 10.098
20 68 121.26 16.167
25 77 151.28 20.169
30 86 187.11 24.946
40 104 279.42 37.253
50 122 405.31 54.037
60 140 572.76 76.362

Reactivity

Like most alkanes, hexane characteristically exhibits low reactivity and are suitable solvents for reactive compounds. Commercial samples of n-hexane however often contains methylcyclopentane, which features tertiary C-H bonds, which are incompatible with some radical reactions.[15]

Safety

Inhalation of n-hexane at 5000 ppm for 10 minutes produces marked vertigo; 2500-1000 ppm for 12 hours produces drowsiness, fatigue, loss of appetite, and paresthesia in the distal extremities; 2500–5000 ppm produces muscle weakness, cold pulsation in the extremities, blurred vision, headache and anorexia.[16] Chronic occupational exposure to elevated levels of n-hexane has been demonstrated to be associated with peripheral neuropathy in auto mechanics in the US, and neurotoxicity in workers in printing presses, and shoe and furniture factories in Asia, Europe, and North America.[17]

The US National Institute for Occupational Safety and Health (NIOSH) has set a recommended exposure limit (REL) for hexane isomers (not n-hexane) of 100 ppm (350 mg/m3 (0.15 gr/cu ft)) over an 8-hour workday.[18] However, for n-hexane, the current NIOSH REL is 50 ppm (180 mg/m3 (0.079 gr/cu ft)) over an 8-hour workday.[19] This limit was proposed as a permissible exposure limit (PEL) by the Occupational Safety and Health Administration in 1989; however, this PEL was overruled in US courts in 1992.[20] The current n-hexane PEL in the US is 500 ppm (1,800 mg/m3 (0.79 gr/cu ft)).[19]

Hexane and other volatile hydrocarbons (petroleum ether) present an aspiration risk.[21] n-Hexane is sometimes used as a denaturant for alcohol, and as a cleaning agent in the textile, furniture, and leather industries. It is slowly being replaced with other solvents.[22]

Like gasoline, hexane is highly volatile and is an explosion risk. Ignition of hexane vapors which had been illegally discharged in the sewers of Louisville (Kentucky) from a soybean processing plant owned by Ralston-Purina caused a series of explosions which destroyed over 21 km of sewer lines and streets in that city.

Incidents

Occupational hexane poisoning has occurred with Japanese sandal workers, Italian shoe workers,[23] Taiwan press proofing workers, and others.[24] Analysis of Taiwanese workers has shown occupational exposure to substances including n-hexane.[25] In 2010–2011, Chinese workers manufacturing iPhones were reported to have suffered hexane poisoning.[26][27]

Hexane was identified as being the cause of the Louisville sewer explosions on 13 February 1981, that destroyed more than 13 miles (21 km) of sewer lines and streets in the center of Louisville in Kentucky, United States.

Biotransformation

n-Hexane is biotransformed to 2-hexanol and further to 2,5-hexanediol in the body. The conversion is catalyzed by the enzyme cytochrome P450 utilizing oxygen from air. 2,5-Hexanediol may be further oxidized to 2,5-hexanedione, which is neurotoxic and produces a polyneuropathy.[22] In view of this behavior, replacement of n-hexane as a solvent has been discussed. n-Heptane is a possible alternative.[28]

شاهد أيضا

المراجع

  1. ^ Hofmann, August Wilhelm Von (1 يناير 1867). "I. On the action of trichloride of phosphorus on the salts of the aromatic monamines". Proceedings of the Royal Society of London. 15: 54–62. doi:10.1098/rspl.1866.0018. S2CID 98496840.
  2. ^ "n-hexane – Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 سبتمبر 2004. Identification and Related Records. Archived from the original on 8 مارس 2012. Retrieved 31 ديسمبر 2011.
  3. ^ William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. pp. 3–298. ISBN 978-1-4987-5429-3.
  4. ^ GHS Classification on [PubChem]
  5. ^ أ ب ت NIOSH Pocket Guide to Chemical Hazards 0322
  6. ^ أ ب "n-Hexane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. ^ "The Tofurky Company : Our Ingredients". Tofurky.com. Archived from the original on 17 مارس 2015. Retrieved 17 مارس 2015.
  8. ^ Palmer, Brian (26 أبريل 2010). "A study found hexane in soy protein. Should you stop eating veggie burgers?". Slate.com. Archived from the original on 9 مارس 2015. Retrieved 17 مارس 2015.
  9. ^ Use of ozone depleting substances in laboratories. Kbh: Nordisk Ministerråd. 2003. ISBN 92-893-0884-2. OCLC 474188215. Archived from the original on 16 يوليو 2012.
  10. ^ Schwindeman, James A.; Woltermann, Chris J.; Letchford, Robert J. (1 مايو 2002). "Safe handling of organolithium compounds in the laboratory". Chemical Health & Safety. 9 (3): 6–11. doi:10.1016/s1074-9098(02)00295-2. ISSN 1074-9098.
  11. ^ "The Hexane Molecule". www.worldofmolecules.com. Retrieved 30 ديسمبر 2021.
  12. ^ "Organic Chemistry-I" (PDF). Nsdl.niscair.res.in. Archived from the original (PDF) on 29 أكتوبر 2013. Retrieved 17 فبراير 2014.
  13. ^ "13. Hydrocarbons | Textbooks". Textbook.s-anand.net. Archived from the original on 6 أكتوبر 2014. Retrieved 17 فبراير 2014.
  14. ^ William D. McCain (1990). The properties of petroleum fluids. PennWell. ISBN 978-0-87814-335-1.
  15. ^ قالب:OrgSynth
  16. ^ "N-HEXANE". Toxicology data network Hazardous Substances Data Bank. National Library of Medicine. Archived from the original on 4 سبتمبر 2015.
  17. ^ Centers for Disease Control and Prevention (CDC) (16 نوفمبر 2001). "n-Hexane-related peripheral neuropathy among automotive technicians--California, 1999-2000". MMWR. Morbidity and Mortality Weekly Report. 50 (45): 1011–1013. ISSN 0149-2195. PMID 11724159.
  18. ^ "CDC – NIOSH Pocket Guide to Chemical Hazards – Hexane isomers (excluding n-Hexane)". cdc.gov. Archived from the original on 31 أكتوبر 2015. Retrieved 3 نوفمبر 2015.
  19. ^ أ ب CDC (28 مارس 2018). "n-Hexane". Centers for Disease Control and Prevention (in الإنجليزية الأمريكية). Retrieved 3 مايو 2020.
  20. ^ "Appendix G: 1989 Air Contaminants Update Project - Exposure Limits NOT in Effect". www.cdc.gov (in الإنجليزية الأمريكية). 20 فبراير 2020. Retrieved 3 مايو 2020.
  21. ^ Gad, Shayne C (2005), "Petroleum Hydrocarbons", Encyclopedia of Toxicology, 3 (2nd ed.), Elsevier, pp. 377–379 
  22. ^ أ ب Clough, Stephen R; Mulholland, Leyna (2005). "Hexane". Encyclopedia of Toxicology. Vol. 2 (2nd ed.). Elsevier. pp. 522–525.
  23. ^ Rizzuto, N; De Grandis, D; Di Trapani, G; Pasinato, E (1980). "N-hexane polyneuropathy. An occupational disease of shoemakers". European Neurology. 19 (5): 308–15. doi:10.1159/000115166. PMID 6249607.
  24. ^ n-Hexane, Environmental Health Criteria, World Health Organization, 1991, http://www.inchem.org/documents/ehc/ehc/ehc122.htm 
  25. ^ Liu, C. H.; Huang, C. Y.; Huang, C. C. (2012). "Occupational Neurotoxic Diseases in Taiwan". Safety and Health at Work. 3 (4): 257–67. doi:10.5491/SHAW.2012.3.4.257. PMC 3521924. PMID 23251841.
  26. ^ "Workers poisoned while making iPhones – ABC News (Australian Broadcasting Corporation)". Australian Broadcasting Corporation. 26 أكتوبر 2010. Archived from the original on 8 أبريل 2011. Retrieved 17 مارس 2015.
  27. ^ David Barboza (22 فبراير 2011). "Workers Sickened at Apple Supplier in China". The New York Times. Archived from the original on 7 أبريل 2015. Retrieved 17 مارس 2015.
  28. ^ Filser JG, Csanády GA, Dietz W, Kessler W, Kreuzer PE, Richter M, Störmer A (1996). "Comparative estimation of the neurotoxic risks of n-hexane and n-heptane in rats and humans based on the formation of the metabolites 2,5-hexanedione and 2,5-heptanedione". Adv Exp Med Biol. Advances in Experimental Medicine and Biology. 387: 411–427. doi:10.1007/978-1-4757-9480-9_50. ISBN 978-1-4757-9482-3. PMID 8794236.


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وصلات خارجية

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