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{{Distinguish|heptene|heptyne}} |
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{{chembox |
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{{Use dmy dates|date=March 2018}} |
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| verifiedrevid = 415519769 |
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{{Chembox |
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| Name = ''n''-Heptane |
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| Watchedfields = changed |
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| ImageFile = Heptane-2D-Skeletal.svg |
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| verifiedrevid = 443853887 |
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| ImageSize = 225px |
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| ImageName = Skeletal formula |
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| ImageFile = Heptane-2D-Skeletal.svg |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = Heptane-3D-balls-B.png |
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| ImageAlt = Skeletal formula of heptane |
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| ImageSize1 = 225px |
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| ImageFile1 = HeptaneFull.png |
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| ImageName1 = Ball-and-stick model |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| Section1 = {{Chembox Identifiers |
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| ImageAlt1 = Skeletal formula of heptane of all implicit carbons shown, and all explicit hydrogens added |
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| ChEBI = 43098 |
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| ImageFile2 = Heptane 3D ball.png |
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| SMILES = CCCCCCC |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ImageFile2_Ref = {{chemboximage|correct|?}} |
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| ImageAlt2 = Ball-and-stick model of the heptane molecule |
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| PIN = Heptane<ref>{{Cite web|title=n-heptane – Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8900&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=2 January 2012|location=USA|date=16 September 2004|at=Identification and Related Records}}</ref> |
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| OtherNames = Septane<ref>{{cite journal|title=I. On the action of trichloride of phosphorus on the salts of the aromatic monamines|first=August Wilhelm Von|last=Hofmann|date=1 January 1867|journal=Proceedings of the Royal Society of London|volume=15|pages=54–62|doi=10.1098/rspl.1866.0018|s2cid=98496840}}</ref> |
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|Section1={{Chembox Identifiers |
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| CASNo = 142-82-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 8900 |
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| ChemSpiderID = 8560 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII = 456148SDMJ |
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| UNII = 456148SDMJ |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/C7H16/c1-3-5-7-6-4-2/h3-7H2,1-2H3 |
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| EINECS = 205-563-8 |
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| InChIKey = IMNFDUFMRHMDMM-UHFFFAOYAU |
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| UNNumber = 1206 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| MeSHName = n-heptane |
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| ChEBI = 43098 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 134658 |
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| ChEMBL = 134658 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| RTECS = MI7700000 |
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| Beilstein = 1730763 |
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| Gmelin = 49760 |
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| SMILES = CCCCCCC |
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| StdInChI = 1S/C7H16/c1-3-5-7-6-4-2/h3-7H2,1-2H3 |
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| StdInChI = 1S/C7H16/c1-3-5-7-6-4-2/h3-7H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IMNFDUFMRHMDMM-UHFFFAOYSA-N |
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| StdInChIKey = IMNFDUFMRHMDMM-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| CASNo = 142-82-5 |
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|Section2 = {{Chembox Properties |
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| RTECS = MI7700000 |
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| PubChem = 8900 |
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| C=7 | H=16 |
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| Appearance = Colourless liquid |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Odor = Petrolic |
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| ChemSpiderID = 8560 |
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| Density = 0.6795 g cm<sup>−3</sup><ref name=b92/> |
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}} |
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| MeltingPtC = −90.549<ref name=b92>{{RubberBible92nd|page=3.290}}</ref> |
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| Section2 = {{Chembox Properties |
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| BoilingPtC = 98.38<ref name=b92/> |
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| Formula = C<sub>7</sub>H<sub>16</sub> |
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| MolarMass = 100.21 g/mol |
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| LogP = 4.274 |
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| VaporPressure = 5.33 kPa (at 20.0 °C) |
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| Appearance = colourless liquid |
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| HenryConstant = 12 nmol Pa<sup>−1</sup> kg<sup>−1</sup> |
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| Density = 0.684 g/ml, liquid |
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| RefractIndex = 1.3855<ref name=b92/> |
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| Solubility = Immiscible |
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| Viscosity = 0.389 mPa·s<ref name="Dymond1994">{{cite journal|last1=Dymond|first1=J. H.|last2=Oye|first2=H. A.|title=Viscosity of Selected Liquid n-Alkanes|journal=Journal of Physical and Chemical Reference Data|volume=23|issue=1|year=1994|pages=41–53|issn=0047-2689|doi=10.1063/1.555943|bibcode=1994JPCRD..23...41D}}</ref> |
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| MeltingPt = −90.61 °C (182.55 K) |
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| Dipole = 0.0 D |
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| BoilingPt = 98.42 °C (371.58 K) |
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| Solubility = 0.0003% (20 °C)<ref name=PGCH/> |
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| Viscosity = 0.386 ] at 25 °C |
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| MagSus = −85.24·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section3 = {{Chembox Thermochemistry |
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| EUClass = Flammable ('''F''')<br />Harmful ('''Xn''')<br />Dangerous for<br />the environment ('''N''') |
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| DeltaHf = −225.2 – −223.6 kJ mol<sup>−1</sup> |
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| NFPA-H = 1 |
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| DeltaHc = −4.825 – −4.809 MJ mol<sup>−1</sup> |
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| NFPA-F = 3 |
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| Entropy = 328.57 J K<sup>−1</sup> mol<sup>−1</sup> |
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| NFPA-R = |
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| HeatCapacity = 224.64 J K<sup>−1</sup> mol<sup>−1</sup> |
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| RPhrases = {{R11}}, {{R38}}, {{R50/53}},<br />{{R65}}, {{R67}} |
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}} |
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| SPhrases = {{S2}}, {{S9}}, {{S16}}, {{S29}}, {{S33}},<br />{{S60}}, {{S61}}, {{S62}} |
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|Section4 = {{Chembox Hazards |
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| FlashPt = −4 °C |
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| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} {{GHS health hazard}} {{GHS environment}} |
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| Autoignition = 220 °C |
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| GHSSignalWord = '''DANGER''' |
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}} |
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| HPhrases = {{H-phrases|225|304|315|336|410}} |
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| Section8 = {{Chembox Related |
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| PPhrases = {{P-phrases|210|261|273|301+310|331}} |
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| Function = ]s |
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| NFPA-H = 1 |
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| OtherFunctn = ]<br />] |
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| NFPA-F = 3 |
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| OtherCpds = ]<br />] |
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| NFPA-R = 0 |
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}} |
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| FlashPtC = −4.0 |
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| AutoignitionPtC = 223.0 |
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| ExploLimits = 1.05–6.7% |
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| PEL = TWA 500 ppm (2000 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0312}}</ref> |
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| IDLH = 750 ppm<ref name=PGCH/> |
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| REL = TWA 85 ppm (350 mg/m<sup>3</sup>) C 440 ppm (1800 mg/m<sup>3</sup>) <ref name=PGCH/> |
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| LCLo = 16,000 ppm (human)<br/>15,000 ppm (mouse, 30 min)<ref name=IDLH>{{IDLH|142825|n-Heptane}}</ref> |
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| LC50 = 17,986 ppm (mouse, 2 hr)<ref name=IDLH/> |
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}} |
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|Section5 = {{Chembox Related |
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| OtherFunction_label = alkanes |
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| OtherFunction = {{Unbulleted list|]|]}} |
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}} |
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}} |
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'''''n''-Heptane''' is the straight-chain ] with the ] H<sub>3</sub>C(CH<sub>2</sub>)<sub>5</sub>CH<sub>3</sub> or C<sub>7</sub>H<sub>16</sub>. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the ] scale (the 100 point is a 100% ]). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and isooctane which is expressed as the percentage of isooctane in heptane and is listed on pumps for gasoline dispensed in the United States and internationally. |
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'''Heptane''' or '''''n''-heptane''' is the straight-chain ] with the ] H<sub>3</sub>C(CH<sub>2</sub>)<sub>5</sub>CH<sub>3</sub> or C<sub>7</sub>H<sub>16</sub>. When used as a test fuel component in ] test engines, a 100% heptane fuel is the zero point of the ] scale (the 100 point is 100% ]). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and iso-octane which is expressed as the percentage of iso-octane in heptane, and is listed on pumps for ] (petrol) dispensed globally. |
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==Uses== |
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==Uses== |
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Heptane (and its many isomers) is widely applied in laboratories as a totally non-polar ]. As a liquid, it is ideal for transport and storage. In the grease spot test, heptane is used to dissolve the oil spot to show the previous presence of organic compounds on a stained paper. This is done by shaking the stained paper in a heptane solution for about half a minute.{{Citation needed|date=July 2009}} |
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Heptane and its many isomers are widely used in ] as a non-polar ].<ref>{{Citation |last=Fang |first=Shen |title=A data-driven sparse learning approach to reduce chemical reaction mechanisms |date=2024-10-13 |url=https://arxiv.org/abs/2410.09901 |access-date=2024-12-10 |doi=10.48550/arXiv.2410.09901 |last2=Zhang |first2=Siyi |last3=Li |first3=Zeyu |last4=Fu |first4=Qingfei |last5=Zhou |first5=Chong-Wen |last6=Hana |first6=Wang |last7=Yang |first7=Lijun}}</ref> As a ], it is ideal for transport and storage. In the grease spot test, heptane is used to dissolve an oil spot to show the previous presence of organic compounds on a stained paper. This is done by shaking the stained paper in a heptane solution for about half a minute.{{Citation needed|date=July 2009}} |
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] into heptane is a means by which aqueous ] may be distinguished from aqueous ]. In water, both bromine and iodine appear ]. However, iodine turns ] when dissolved in heptane, whereas the bromine solution remains brown. |
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Aqueous ] may be distinguished from aqueous ] by its appearance after ] into heptane. In water, both bromine and iodine appear ]. However, iodine turns ] when dissolved in heptane, whereas the bromine solution remains brown. |
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Heptane is commercially available as both pure and mixed isomers for use in paints and coatings, as the ] solvent "Bestine"<ref>{{Cite web |date=27 June 2022 |title=BESTINE SOLVENT & THINNER OSHA SDS |url=https://www.speedballart.com/wp-content/uploads/2022/08/Bestine-OSHA-SDS-EN.pdf |url-status=live |archive-url=https://web.archive.org/web/20230426012051/https://www.speedballart.com/wp-content/uploads/2022/08/Bestine-OSHA-SDS-EN.pdf |archive-date=26 April 2023 |access-date=24 December 2024 |publisher=Speedball Art Products Co.}}</ref>, the outdoor stove fuel "Powerfuel" by Primus, as pure ''n''-heptane for research and development and pharmaceutical manufacturing and as a minor component of ] (petrol). On average, gasoline is about 1% heptane.<ref>{{cite journal |last1=Conner |first1=Teri L. |last2=Lonneman |first2=William A. |last3=Seila |first3=Robert L. |title=Transportation-Related Volatile Hydrocarbon Source Profiles Measured in Atlanta |journal=Journal of the Air & Waste Management Association |date=1 May 1995 |volume=45 |issue=5 |pages=383–394 |doi=10.1080/10473289.1995.10467370|doi-access=free |bibcode=1995JAWMA..45..383C }}</ref><ref>{{cite journal |last1=Schauer |first1=James J. |last2=Kleeman |first2=Michael J. |last3=Cass |first3=Glen R. |last4=Simoneit |first4=Bernd R. T. |title=Measurement of Emissions from Air Pollution Sources. 5. C 1 −C 32 Organic Compounds from Gasoline-Powered Motor Vehicles |journal=Environmental Science & Technology |date=1 March 2002 |volume=36 |issue=6 |pages=1169–1180 |doi=10.1021/es0108077|pmid=11944666 |bibcode=2002EnST...36.1169S }}</ref> |
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Heptane is commercially available as mixed isomers for use in paints and coatings, as the ] solvent "Bestine", the outdoor stove fuel "Powerfuel" by Primus, as pure n-Heptane for research and development and pharmaceutical manufacturing and as a minor component of gasoline. |
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Heptane is also used as an ] by ]. Since 1974, the ] has issued ]s that some collectors find difficult to separate from envelopes via the traditional method of soaking in water. Heptane-based products like Bestine, as well as ]-based products, have become popular solvents for removing stamps more easily.<ref>{{cite web |last1=Butler |first1=Peter |title=It's Like Magic: Removing Self-Adhesive Stamps from Paper |url=https://classic.stamps.org/userfiles/file/HowTos/RemovingSelfAdhesives-Part1.pdf |publisher=American Philatelic Society |access-date=15 June 2020}}</ref> |
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===Octane rating scale=== |
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===Octane rating scale=== |
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''n''-Heptane is the zero point of the ] scale. It is undesirable in ], because it burns ]ly, causing ] ], as opposed to branched-chain ] isomers, which burn more slowly and give better performance. It was chosen as the zero point of the scale because of the availability of very high purity ''n''-heptane, unmixed with other isomers of heptane or other alkanes, distilled from the ] of ] and from the fruit of ]. Other sources of heptane and octane, produced from ], contain a mixture of different isomers with greatly differing ratings and do not give as precise a zero point. ChevronPhillips Specialty Chemical produces a specialized grade of high purity n-Heptane (>99.0%) from crude oil through precision refining and distillation that is used in the measurement of octane rating for fuels. |
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''n''-Heptane is defined as the zero point of the ] scale. It is a lighter component in ] and burns more ]ly, causing ] pre-ignition (]) in its pure form, as opposed to ] isomers, which burn more slowly and give less knocking. It was originally chosen as the zero point of the scale because of the availability of very high purity ''n''-heptane, unmixed with other isomers of heptane or other alkanes, distilled from the ] of ] and from the fruit of '']''. Other sources of heptane and octane, produced from ], contain a mixture of different isomers with greatly differing ratings, and do not give as precise a zero point. |
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== Isomers and enantiomers == |
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==Isomers and enantiomers== |
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{{Main|C7H16}} |
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Heptane has nine ]s, or eleven if ]s are counted: |
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Heptane has nine ]s, or eleven if ]s are counted: |
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* Heptane (''n''-heptane), H<sub>3</sub>C–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>3</sub>, |
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* Heptane (''n''-heptane), H<sub>3</sub>C–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>3</sub>, |
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* ] (isoheptane), H<sub>3</sub>C–CH(CH<sub>3</sub>)–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>3</sub>, |
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* ] (isoheptane), H<sub>3</sub>C–CH(CH<sub>3</sub>)–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>3</sub>, |
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* ], H<sub>3</sub>C–CH<sub>2</sub>–C<sup>*</sup>H(CH<sub>3</sub>)–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>3</sub> (]), |
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* ], H<sub>3</sub>C–CH<sub>2</sub>–C<sup>*</sup>H(CH<sub>3</sub>)–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>3</sub> (]), |
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* ] (neoheptane), (H<sub>3</sub>C)<sub>3</sub>–C–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>3</sub>, |
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* ] (neoheptane), H<sub>3</sub>C–C(CH<sub>3</sub>)<sub>2</sub>–CH<sub>2</sub>–CH<sub>2</sub>–CH<sub>3</sub>, |
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* ], (H<sub>3</sub>C)<sub>2</sub>–CH–C<sup>*</sup>H(CH<sub>3</sub>)–CH<sub>2</sub>–CH<sub>3</sub> (chiral), |
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* ], H<sub>3</sub>C–CH(CH<sub>3</sub>)–C<sup>*</sup>H(CH<sub>3</sub>)–CH<sub>2</sub>–CH<sub>3</sub> (]), |
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* ], (H<sub>3</sub>C)<sub>2</sub>–CH–CH<sub>2</sub>–CH–(CH<sub>3</sub>)<sub>2</sub>, |
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* ], H<sub>3</sub>C–CH(CH<sub>3</sub>)–CH<sub>2</sub>–CH(CH<sub>3</sub>)–CH<sub>3</sub>, |
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* ], H<sub>3</sub>C–CH<sub>2</sub>–C(CH<sub>3</sub>)<sub>2</sub>–CH<sub>2</sub>–CH<sub>3</sub>, |
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* ], H<sub>3</sub>C–CH<sub>2</sub>–C(CH<sub>3</sub>)<sub>2</sub>–CH<sub>2</sub>–CH<sub>3</sub>, |
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* ], H<sub>3</sub>C–CH<sub>2</sub>–CH(CH<sub>2</sub>CH<sub>3</sub>)–CH<sub>2</sub>–CH<sub>3</sub>, |
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* ], H<sub>3</sub>C–CH<sub>2</sub>–CH(CH<sub>2</sub>CH<sub>3</sub>)–CH<sub>2</sub>–CH<sub>3</sub>, |
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* ], CH<sub>3</sub>–C(CH<sub>3</sub>)<sub>2</sub>–CH(CH<sub>3</sub>)–CH<sub>3</sub>, this isomer is also known as pentamethylethane and triptane.<ref></ref> |
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* ], H<sub>3</sub>C–C(CH<sub>3</sub>)<sub>2</sub>–CH(CH<sub>3</sub>)–CH<sub>3</sub>, also known as pentamethylethane and triptane.<ref> {{Webarchive|url=https://web.archive.org/web/20110927014042/http://members.optushome.com.au/scottsoftb/skeletons3.htm |date=27 September 2011 }}. Members.optushome.com.au. Retrieved on 2012-03-04.</ref> |
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==Preparation== |
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The linear ''n''-heptane can be obtained from ] oil.<ref name=edgar>{{cite journal | doi = 10.1021/ja01380a027| title = The preparation and properties of the isomeric heptanes. Part I. Preparation | date = 1929| last1 = Edgar| first1 = Graham| last2 = Calingaert| first2 = George| last3 = Marker| first3 = R. E.| journal = Journal of the American Chemical Society| volume = 51| issue = 5| pages = 1483–1491}}</ref> The six branched isomers without a quaternary carbon can be prepared by creating a suitable secondary or tertiary ] by the ], converting it to an ] by ], and ] the latter.<ref name=edgar/> The 2,2-dimethylpentane isomer can be prepared by reacting ''tert''-butyl chloride with ''n''-propyl magnesium bromide.<ref name=edgar/> The 3,3-dimethylpentane isomer can be prepared from ''tert''-amyl chloride and ethyl magnesium bromide.<ref name=edgar/> |
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==Health risks== |
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{{expand section|date=June 2015}} |
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<!-- Need info on effects of *chronic* exposure to vapors; also, may cause cataracts --> |
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Acute exposure to heptane vapors can cause ], stupor, incoordination, loss of appetite, nausea, dermatitis, chemical pneumonitis, unconsciousness, or possible peripheral neuropathy.<ref>{{cite journal|last1=Patty|first1= FA|last2=Yant|first2= WP|year=1929|title=Odor intensity and symptoms produced by commercial propane, butane, pentane, hexane, and heptane vapor.|journal=Report of Investigations|publisher=US Department of Commerce, U.S. Bureau of Mines|volume=2979|issue=December|pages=1–10|url=https://babel.hathitrust.org/cgi/pt?id=umn.31951000866454o;view=1up;seq=652}}</ref> |
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In a ] study, it was found that prolonged exposure to heptane may also cause a state of ] and uncontrolled hilarity in some participants and a ] lasting for 30 minutes after exposure for others.<ref>{{Cite web|date=2018-11-02|title=CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): n-Heptane - NIOSH Publications and Products|url=https://www.cdc.gov/niosh/idlh/142825.html|access-date=2021-12-06|website=www.cdc.gov|language=en-us}}</ref> Prolonged exposure can also lead to ] or cracking, since the substance defats skin.<ref>{{Cite web |title=ICSC 0657 - n-HEPTANE |url=https://chemicalsafety.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0657&p_version=2 |access-date=2024-09-11 |website=chemicalsafety.ilo.org}}</ref> |
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According to information from the New Jersey Department of Health and Senior Services, ''n''-heptane can penetrate the skin, and further health effects may occur immediately or shortly after exposure to it. Exposure to ''n''-heptane may lead to short-term health effects like irritation of the eyes, nose, or throat, headache, dizziness, or loss of consciousness; and chronic health effects, like reduced memory and concentration, sleep disturbance, and reduced coordination due to its effects on the nervous system.<ref>{{Cite web |title=n- HEPTANE |url=https://nj.gov/health/eoh/rtkweb/documents/fs/1339.pdf}}</ref> |
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Upon chronic exposure, it can pose a ] or ].<ref>{{Cite web |date=2004 |title=Hazardous Substance Fact Sheet |url=https://nj.gov/health/eoh/rtkweb/documents/fs/1339.pdf |access-date=11 September 2024 |page=2}}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist|30em}} |
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==External links== |
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==External links== |
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* (''n''-heptane) |
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* (''n''-heptane) |
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* (2-methylhexane) |
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* (2-methylhexane) |
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*{{ecb}} |
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* |
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* |
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* |
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{{alkanes}} |
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{{Alkanes}} |
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{{Hydrides by group}} |
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{{Authority control}} |
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