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178:
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28:
37:
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577:
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1007:
because it doesn't have as many hydrogen atoms). This means that the average C-C-C angle is less than 108°. There are two conformations that give local minima of the energy, the "envelope" and the "half-chair". The envelope has mirror symmetry
1107:
1252:
Singh, V. (2019). Developing a model system of liquid lubricants for space applications: Multiple alkylated cyclopentane in alumina enclosed surface. Missouri
University of Science and Technology.
1243:
Loewenthal, S., Jones, W., & Predmore, R. (1999, September). Life of pennzane and 815Z-lubricated instrument bearings cleaned with non-CFC solvents. In
European Space Mechanisms and Tribology.
984:, the angles at the vertices are all 108°, slightly less than the bond angle in perfectly tetrahedrally bonded carbon, which is about 109.47°. However, cyclopentane is not planar in its normal
594:
1354:
Zhang, Chengping; Qing, Feiyao; Quan, Hengdao; Sekiya, Akira (January 2016). "Synthesis of 1,1,2,2,3,3,4-heptafluorocyclopentane as a new generation of green solvent".
1173: : 322–330; see especially pages 327-330. Wislicenus prepared cyclopentane from cyclopentanone ("Ketopentamethen"), which is prepared by heating calcium adipate.
579:
921:
Multiply alkylated cyclopentane (MAC) lubricants, such as 1,3,4-tri-(2-octyldodecyl) cyclopentane, have low volatility and are used by NASA in space applications.
940:
1022:). In both cases the symmetry implies that there are two pairs of equal C-C-C angles and one C-C-C angle that has no pair. In fact for cyclopentane, unlike for
1148:
647:
924:
Cyclopentane requires safety precautions to prevent leakage and ignition as it is both highly flammable and can also cause respiratory arrest when inhaled.
745:
601:
1042:, it is not possible geometrically for all the angles and bond lengths to be equal except if it is in the form of a flat regular pentagon.
336:
1228:
1418:
988:. It puckers in order to increase the distances between the hydrogen atoms (something which does not happen in the planar
904:, to be marked with cyclopentane warning labels due to its flammability. Cyclopentane is also used in the manufacture of
740:
301:
1016:
1009:
752:
1183:
Schilling, S. L. (May 2000). "Appliance Rigid Foams Blown with
Cyclopentane and Cyclopentane/Isopentane Blends".
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896:, it is common for domestic appliances that are insulated with cyclopentane-based foam, such as
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989:
885:
1524:
1404:
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840:
253:
55:
1292:
Robert W. Virtue, M.D. (May 1949). "OBSERVATIONS ON CYCLOPENTANE AS AN ANESTHETIC AGENT".
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1319:
Tatlow, John Colin (1995). "Cyclic and bicyclic polyfluoro-alkanes and -alkenes".
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953:. Such species are conceivable refrigerants and specialty solvents.
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Except where otherwise noted, data are given for materials in their
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Cyclopentane can be fluorinated to give compounds ranging from
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228:
126:
104:
270:
816:
684:
396:
1015:), while the half chair has two-fold rotational symmetry (
807:
atoms above and below the plane. It occurs as a colorless
475:
869:. For example, when passed over a hot platinum surface,
1270:
1291:
1149:
National
Institute for Occupational Safety and Health
960:
including many useful drugs. Examples include most
853:
It was first prepared in 1893 by the German chemist
1353:
860:
1506:
1255:
892:. While cyclopentane is not typically used as a
216:
575:
90:
1412:
1163:"Der Pentamethenylalkohol und seine Derivate"
421:−93.9 °C (−137.0 °F; 179.2 K)
1176:
1108:Institute for Occupational Safety and Health
618:−37.2 °C (−35.0 °F; 236.0 K)
1312:
884:, replacing ozone-depleting agents such as
431:49.2 °C (120.6 °F; 322.3 K)
1419:
1405:
827:is 49 °C. Cyclopentane is in the class of
285:
176:
154:
1219:
1182:
252:
1143:NIOSH Pocket Guide to Chemical Hazards.
1263:"Pennzoil Products: High Tech Products"
799:287-92-3, consisting of a ring of five
281:
1507:
1318:
1161:J. Wislicenus and W. Hentschel (1893)
1138:
1136:
1134:
1132:
1130:
956:The cyclopentane ring is pervasive in
876:Cyclopentane is principally used as a
632:361 °C (682 °F; 634 K)
167:
1400:
1165:(Cyclopentanol and its derivatives),
313:Key: RGSFGYAAUTVSQA-UHFFFAOYSA-N
134:
850:at a high temperature and pressure.
1237:
1127:
323:Key: RGSFGYAAUTVSQA-UHFFFAOYAL
207:
13:
571:
310:InChI=1S/C5H10/c1-2-4-5-3-1/h1-5H2
35:
26:
14:
1536:
1378:
1226:Greenpeace - Appliance Insulation
320:InChI=1/C5H10/c1-2-4-5-3-1/h1-5H2
1426:
1384:
1306:10.1097/00000542-194905000-00007
1110:, accessed on 28 February 2015.
1071:
1059:
1047:
975:
730:
1347:
1285:
1269:. 12 April 2004. Archived from
726:(at 25 °C , 100 kPa).
1368:10.1016/j.jfluchem.2015.10.012
1246:
1155:
1113:
1090:
861:Production, occurrence and use
541:Occupational safety and health
1:
1356:Journal of Fluorine Chemistry
1321:Journal of Fluorine Chemistry
1083:
652:(US health exposure limits):
1333:10.1016/0022-1139(95)03293-m
1185:Journal of Cellular Plastics
882:polyurethane insulating foam
873:converts into cyclopentane.
7:
865:Cycloalkanes are formed by
803:atoms each bonded with two
22:
10:
1541:
1197:10.1177/0021955X0003600302
1121:"ICSC 0353 - CYCLOPENTANE"
1434:
1104:GESTIS Substance Database
720:
695:
646:
538:
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352:
332:
297:
74:
66:
54:
49:
21:
1036:cyclohexane conformation
678:TWA 600 ppm (1720 mg/m)
391:clear, colorless liquid
383:70.1 g/mol
503:Magnetic susceptibility
990:cyclopentadienyl anion
880:in the manufacture of
835:that have one or more
582:
40:
31:
941:perfluorocyclopentane
581:
39:
30:
1520:Hydrocarbon solvents
1393:at Wikimedia Commons
564:(fire diamond)
56:Preferred IUPAC name
867:catalytic reforming
855:Johannes Wislicenus
846:in the presence of
438:Solubility in water
18:
1231:2008-10-30 at the
1167:Annalen der Chemie
839:. It is formed by
823:is −94 °C and its
753:Infobox references
696:Related compounds
687:(Immediate danger)
583:
41:
32:
16:
1502:
1501:
1389:Media related to
761:Chemical compound
759:
758:
702:Related compounds
509:-59.18·10 cm/mol
443:156 mg·l (25 °C)
266:CompTox Dashboard
116:Interactive image
45:
44:
1532:
1494:Cyclotetradecane
1421:
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1273:on 12 April 2004
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982:regular pentagon
958:natural products
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938:
783:chemical formula
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638:Explosive limits
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516:Refractive index
360:Chemical formula
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1489:Cyclotridecane
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1191:(3): 190–206.
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871:2-methylbutane
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821:freezing point
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771:) is a highly
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1515:Cyclopentanes
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1484:Cyclododecane
1482:
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1479:Cycloundecane
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1038:) and higher
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986:conformations
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976:Conformations
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825:boiling point
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767:(also called
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674:(Recommended)
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661:(Permissible)
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417:Melting point
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168:ECHA InfoCard
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34:
29:
25:
24:
20:
17:Cyclopentane
1525:Cycloalkanes
1459:Cycloheptane
1449:Cyclopentane
1448:
1439:Cyclopropane
1428:Cycloalkanes
1391:Cyclopentane
1359:
1355:
1349:
1324:
1320:
1314:
1297:
1293:
1287:
1275:. Retrieved
1271:the original
1267:pennzane.com
1266:
1257:
1248:
1239:
1221:
1188:
1184:
1178:
1170:
1166:
1157:
1115:
1099:cyclopentane
1098:
1092:
1040:cycloalkanes
979:
955:
926:
923:
920:
875:
864:
852:
837:carbon rings
829:cycloalkanes
768:
765:Cyclopentane
764:
763:
707:cyclopropane
648:
625:Autoignition
560:
550:Main hazards
539:
519:
487:
401:mild, sweet
229:RTECS number
75:Identifiers
67:Other names
60:Cyclopentane
1474:Cyclodecane
1469:Cyclononane
1464:Cyclooctane
1454:Cyclohexane
1444:Cyclobutane
1327:(1): 7–34.
1300:: 318–324.
1066:3D envelope
1024:cyclohexane
968:, and some
894:refrigerant
844:cyclohexane
779:hydrocarbon
715:cyclohexane
711:cyclobutane
627:temperature
614:Flash point
544:(OHS/OSH):
453:soluble in
411:0.751 g/cm
388:Appearance
353:Properties
174:100.005.470
136:CHEBI:23492
1509:Categories
1097:Record of
1084:References
1078:Half-chair
797:CAS number
642:1.1%-8.7%
554:Flammable
449:Solubility
379:Molar mass
254:T86PB90RNU
147:ChemSpider
103:3D model (
82:CAS Number
1362:: 11–16.
1341:0022-1139
1213:0021-955X
1205:1530-7999
916:adhesives
906:synthetic
890:HCFC-141b
776:alicyclic
773:flammable
769:C pentane
478:(20 °C)
236:GY2390000
195:206-016-6
187:EC Number
1229:Archived
1151:(NIOSH).
1054:Envelope
962:steroids
902:freezers
841:cracking
831:, being
805:hydrogen
561:NFPA 704
534:Hazards
505:(χ)
92:287-92-3
1277:15 July
1145:"#0171"
1106:of the
1102:in the
848:alumina
833:alkanes
811:with a
746:what is
744: (
529:1.4065
484:Acidity
459:acetone
455:ethanol
407:Density
373:
344:C1CCCC1
205:PubChem
1339:
1211:
1203:
1034:, see
970:lipids
913:rubber
909:resins
886:CFC-11
819:. Its
815:-like
813:petrol
809:liquid
801:carbon
741:verify
738:
337:SMILES
50:Names
1201:eISSN
980:In a
781:with
691:N.D.
665:none
649:NIOSH
463:ether
302:InChI
127:ChEBI
105:JSmol
1337:ISSN
1279:2022
1209:ISSN
911:and
900:and
888:and
817:odor
795:and
685:IDLH
496:~45
397:Odor
245:UNII
218:9253
156:8896
1364:doi
1360:181
1329:doi
1302:doi
1193:doi
1171:275
939:to
672:REL
659:PEL
476:kPa
474:45
271:EPA
208:CID
1511::
1358:.
1335:.
1325:75
1323:.
1298:10
1296:.
1265:.
1207:.
1199:.
1189:36
1187:.
1169:,
1147:.
1129:^
1032:12
1026:(C
972:.
964:,
950:10
918:.
857:.
792:10
713:,
709:,
493:)
486:(p
461:,
457:,
371:10
1420:e
1413:t
1406:v
1370:.
1366::
1343:.
1331::
1308:.
1304::
1281:.
1215:.
1195::
1123:.
1030:H
1028:6
1019:2
1017:C
1012:s
1010:C
1008:(
1003:5
1000:−
997:H
995:5
993:C
948:F
946:5
944:C
937:F
935:9
933:H
931:5
929:C
790:H
788:5
786:C
736:Y
602:0
595:3
588:1
525:)
523:D
520:n
518:(
491:a
488:K
369:H
367:5
365:C
273:)
269:(
107:)
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