795:
1974:
3056:
1861:
3044:
3020:
780:
2996:
3118:
3101:
29:
3135:
3008:
3084:
2984:
3032:
1970:. Hydrocarbons are introduced into the environment through their extensive use as fuels and chemicals as well as through leaks or accidental spills during exploration, production, refining, or transport of fossil fuels. Anthropogenic hydrocarbon contamination of soil is a serious global issue due to contaminant persistence and the negative impact on human health.
1993:
Bioremediation of hydrocarbon from soil or water contaminated is a formidable challenge because of the chemical inertness that characterize hydrocarbons (hence they survived millions of years in the source rock). Nonetheless, many strategies have been devised, bioremediation being prominent. The
1984:
When soil is contaminated by hydrocarbons, it can have a significant impact on its microbiological, chemical, and physical properties. This can serve to prevent, slow down or even accelerate the growth of vegetation depending on the exact changes that occur. Crude oil and natural gas are the two
1910:
A seemingly limitless variety of compounds comprise petroleum, hence the necessity of refineries. These hydrocarbons consist of saturated hydrocarbons, aromatic hydrocarbons, or combinations of the two. Missing in petroleum are alkenes and alkynes. Their production requires refineries.
901:
The noteworthy feature of saturated hydrocarbons is their inertness. Unsaturated hydrocarbons (alkanes, alkenes and aromatic compounds) react more readily, by means of substitution, addition, polymerization. At higher temperatures they undergo dehydrogenation, oxidation and combustion.
1911:
Petroleum-derived hydrocarbons are mainly consumed for fuel, but they are also the source of virtually all synthetic organic compounds, including plastics and pharmaceuticals. Natural gas is consumed almost exclusively as fuel. Coal is used as a fuel and as a reducing agent in
1695:
373:
The term 'aliphatic' refers to non-aromatic hydrocarbons. Saturated aliphatic hydrocarbons are sometimes referred to as 'paraffins'. Aliphatic hydrocarbons containing a double bond between carbon atoms are sometimes referred to as 'olefins'.
261:
and may be either linear or branched species. One or more of the hydrogen atoms can be replaced with other atoms, for example chlorine or another halogen: this is called a substitution reaction. An example is the conversion of methane to
1850:
2466:
van Dijk, J.P. (2022); Unravelling the Maze of
Scientific Writing Through the Ages: On the Origins of the Terms Hydrocarbon, Petroleum, Natural Gas, and Methane. Amazon Publishers, 166 pp. PaperBack Edition B0BKRZRKHW.
1433:
1531:
1903:) and coal are generally thought to be products of decomposition of organic matter. Coal, in contrast to petroleum, is richer in carbon and poorer in hydrogen. Natural gas is the product of
916:
Of the classes of hydrocarbons, aromatic compounds uniquely (or nearly so) undergo substitution reactions. The chemical process practiced on the largest scale is the reaction of benzene and
1546:
166:, or their hydrocarbon derivatives and purified forms. Combustion of hydrocarbons is the main source of the world's energy. Petroleum is the dominant raw-material source for organic
849:
Some large-scale non-fuel applications of hydrocarbons begin with ethane and propane, which are obtained from petroleum and natural gas. These two gases are converted either to
2000:
2768:
Lim, Mee Wei; Lau, Ee Von; Poh, Phaik Eong (2016). "A comprehensive guide of remediation technologies for oil contaminated soil — Present works and future directions".
893:
bacteria from plants that naturally produce hydrocarbons have been used in hydrocarbon degradation in attempts to deplete hydrocarbon concentration in polluted soils.
2927:
2673:
4242:
3824:
3763:
806:
source. Methane is the predominant component of natural gas. C through C alkanes, alkenes, cycloalkanes, and aromatic hydrocarbons are the main components of
4232:
4227:
3748:
2030:
Hydrocarbons are generally of low toxicity, hence the widespread use of gasoline and related volatile products. Aromatic compounds such as benzene and
4214:
3735:
1724:
991:
Substitution reactions occur also in saturated hydrocarbons (all single carbon–carbon bonds). Such reactions require highly reactive reagents, such as
861:
respectively. Global consumption of benzene in 2021 is estimated at more than 58 million metric tons, which will increase to 60 million tons in 2022.
818:, and specialized industrial solvent mixtures. With the progressive addition of carbon units, the simple non-ring structured hydrocarbons have higher
3806:
191:
1994:
basic problem with bioremediation is the paucity of enzymes that act on them. Nonetheless, the area has received regular attention. Bacteria in the
1139:
Addition reactions apply to alkenes and alkynes. In this reaction a variety of reagents add "across" the pi-bond(s). Chlorine, hydrogen chloride,
4254:
3775:
3124:
4300:
874:"scents" in order to determine kin from non-kin. This hydrocarbon composition varies between age, sex, nest location, and hierarchal position.
270:. Halogenating a hydrocarbon produces something that is not a hydrocarbon. It is a very common and useful process. Hydrocarbons with the same
4315:
4310:
4295:
3880:
1340:
766:
736:
2264:
4384:
4353:
4132:
4122:
4007:
616:
231:. The most general form of saturated hydrocarbons, (whether linear or branched species, and whether with or without one or more rings) is C
1452:
1299:, heating (such as home heating) and transportation. Often this energy is used directly as heat such as in home heaters, which use either
4389:
4368:
4363:
4147:
4142:
4137:
4127:
4022:
4017:
4012:
4002:
3668:
706:
676:
1918:
A small fraction of hydrocarbon found on earth, and all currently known hydrocarbon found on other planets and moons, is thought to be
756:
726:
721:
3172:
2589:
794:
4976:
3181:
195:
3509:
1307:. The hydrocarbon is burnt and the heat is used to heat water, which is then circulated. A similar principle is used to create
2753:
2155:
1998:
of the ocean's crust can degrade hydrocarbons; but the extreme environment makes research difficult. Other bacteria such as
2916:
369:. 10% of total nonmethane organic carbon emission are aromatic hydrocarbons from the exhaust of gasoline-powered vehicles.
3072:
2180:
202:
1887:, and natural gas. Since thousands of years they have been exploited and used for a vast range of purposes. Petroleum (
2472:
1690:{\displaystyle {\ce {C}}_{n}{\ce {H}}_{2n+2}+\left({{3n+1} \over 2}\right){\ce {O2->}}n{\ce {CO2}}+(n+1){\ce {H2O}}}
2960:
2513:
2492:
2128:
312:, which have one or more double or triple bonds between carbon atoms. Those with one or more double bonds are called
4434:
1947:
2201:
999:. In the case of chlorination, one of the chlorine atoms replaces a hydrogen atom. The reactions proceed via
5083:
5078:
3165:
2330:"Hydrocarbon degradation potential and plant growth-promoting activity of culturable endophytic bacteria of
5112:
4969:
1225:, in which substituents attached by C–C bonds are exchanged between molecules. For a single C–C bond it is
864:
Hydrocarbons are also prevalent in nature. Some eusocial arthropods, such as the
Brazilian stingless bee,
2393:
1195:
3502:
3090:
2974:
2052:
1919:
866:
986:
2884:
2811:
Mason OU, Nakagawa T, Rosner M, Van
Nostrand JD, Zhou J, Maruyama A, Fisk MR, Giovannoni SJ (2010).
3158:
1700:
Partial oxidation characterizes the reactions of alkenes and oxygen. This process is the basis of
5037:
4962:
3894:
2870:
Yakimov, M. M.; Timmis, K. N.; Golyshin, P. N. (2007). "Obligate oil-degrading marine bacteria".
2227:
2087:
2072:
309:
790:
is processed in several stages to form desired hydrocarbons, used as fuel and in other products.
4844:
3658:
2952:
2943:
2879:
5140:
5088:
5058:
5033:
5023:
4905:
4839:
3495:
3060:
2025:
1004:
911:
871:
291:
267:
205:
hydrocarbons, which are the simplest of the hydrocarbon types. They are composed entirely of
3444:
2562:
2226:
Nunes, T.M.; Turatti, I.C.C.; Mateus, S.; Nascimento, F.S.; Lopes, N.P.; Zucchi, R. (2009).
1925:
Hydrocarbons such as ethylene, isoprene, and monoterpenes are emitted by living vegetation.
4423:
4222:
2824:
2777:
2629:
2535:
2431:
2349:
2294:
2282:
2082:
1251:
1051:
1000:
358:
32:
1973:
8:
5073:
4751:
3475:
3316:
3012:
2585:
1942:
889:
as an alternative and renewable energy source for vehicles that use diesel. Furthermore,
885:
210:
167:
2828:
2781:
2633:
2539:
2435:
2353:
2298:
2038:. Certain rare polycyclic aromatic compounds are carcinogenic. Hydrocarbons are highly
838:
retort. They are collected and widely utilized as roofing compounds, pavement material (
5107:
4938:
4895:
3753:
3743:
3262:
3048:
2847:
2812:
2647:
2619:
2370:
2329:
2310:
879:
275:
3471:
4829:
4801:
4644:
4404:
4399:
4237:
3758:
2956:
2897:
2852:
2793:
2749:
2718:
2665:
2651:
2509:
2488:
2468:
2449:
2375:
2256:
2161:
2151:
2124:
2057:
1308:
1234:
1230:
1226:
1134:
835:
811:
287:
279:
271:
60:
44:
2789:
2314:
4793:
3024:
2988:
2889:
2842:
2832:
2785:
2741:
2708:
2637:
2543:
2439:
2365:
2357:
2302:
2246:
2077:
1978:
1162:
1122:
826:
temperatures, and deeper color. At the opposite extreme from methane lie the heavy
80:
68:
1845:{\displaystyle {\ce {{\underset {benzene}{C6H6}}+{15 \over 2}O2->6CO2{+}3H2O}}}
1295:
Combustion of hydrocarbons is currently the main source of the world's energy for
4954:
4943:
4900:
4809:
4683:
3648:
3638:
3306:
2893:
2837:
2606:
Guzman-Ramirez, L.; Lagadec, E.; Jones, D.; Zijlstra, A. A.; Gesicki, K. (2014).
2593:
2145:
2005:
1701:
1268:
1262:
482:
258:
170:
such as solvents and polymers. Most anthropogenic (human-generated) emissions of
3055:
2232:(Hymenoptera, Apidae, Meliponini): Differences between Colonies, Castes and Age"
95:. They occur in a diverse range of molecular structures and phases: they can be
5065:
5051:
4874:
4869:
4834:
4785:
4691:
3663:
3653:
2444:
2419:
2067:
1967:
1959:
1904:
1319:
1296:
1171:
823:
783:
283:
175:
171:
3107:
2361:
5134:
4551:
4358:
4348:
3844:
3000:
2813:"First investigation of the microbiology of the deepest layer of ocean crust"
2745:
2722:
2453:
2165:
1537:
1211:
1191:
974:
761:
731:
525:
366:
52:
3150:
2713:
2696:
2526:
Sephton, M. A.; Hazen, R. M. (2013). "On the
Origins of Deep Hydrocarbons".
182:, or methane released from the handling of natural gas or from agriculture.
5008:
4657:
4621:
4517:
4290:
4280:
4189:
4179:
4169:
3710:
3700:
3690:
3036:
2901:
2856:
2797:
2736:"Additives Affecting the Microbial Degradation of Petroleum Hydrocarbons",
2642:
2607:
2547:
2379:
2260:
2062:
1933:
1929:
1860:
1439:
1312:
1199:
1194:. Oligomers (chains of a few monomers) may be produced, for example in the
1179:
1175:
1003:, in which the halogen first dissociates into a two neutral radical atoms (
921:
611:
550:
488:
254:
179:
136:
124:
20:
2251:
2034:
are narcotic and chronic toxins, and benzene in particular is known to be
5045:
4705:
4662:
4635:
4569:
4532:
4451:
4305:
4285:
4272:
4204:
4199:
4194:
4184:
4174:
4161:
3992:
3725:
3720:
3715:
3705:
3695:
3682:
1912:
1443:
1318:
Common properties of hydrocarbons are the facts that they produce steam,
1304:
1183:
970:
819:
701:
671:
641:
581:
520:
406:
334:
317:
299:
295:
206:
159:
147:
140:
128:
3248:
3043:
1428:{\displaystyle {\ce {{\underset {methane}{CH4}}+ 2O2 -> CO2 + 2H2O}}}
5018:
5003:
4764:
4652:
4456:
4343:
4333:
4262:
3997:
3819:
3814:
3789:
3643:
3633:
2697:"Root Exudation: The Ecological Driver of Hydrocarbon Rhizoremediation"
2306:
2035:
1705:
1323:
1290:
1156:
890:
798:
Tank wagon 33 80 7920 362–0 with hydrocarbon gas at
Bahnhof Enns (2018)
555:
493:
303:
263:
84:
2418:
Zou, Caineng; Zhao, Qun; Zhang, Guosheng; Xiong, Bo (1 January 2016).
4769:
4507:
4476:
4466:
4461:
4338:
4066:
3854:
3849:
3628:
3302:
2147:
Amino Acids and the
Asymmetry of Life: Caught in the Act of Formation
2039:
1880:
1526:{\displaystyle {\ce {{\underset {methane}{CH4}}+ O2 -> C + 2H2O}}}
1300:
1279:
1202:
are extended to make longer α-olefins by adding ethylene repeatedly.
1187:
858:
787:
779:
646:
586:
454:
411:
155:
3141:
1330:
is required for combustion to take place. The simplest hydrocarbon,
5013:
4933:
4928:
4738:
4730:
4722:
4602:
4594:
4586:
4537:
4522:
4512:
4502:
4497:
4471:
4394:
4106:
4086:
3936:
3864:
3859:
3839:
3370:
3360:
3347:
3286:
3252:
2013:
2009:
1869:
1144:
996:
992:
854:
843:
815:
807:
751:
746:
716:
88:
72:
28:
2624:
2605:
1865:
4890:
4864:
4714:
4559:
4492:
4091:
4081:
4071:
3961:
3951:
3941:
3829:
3795:
3783:
3597:
3587:
3577:
3567:
2995:
2420:"Energy revolution: From a fossil energy era to a new energy era"
2031:
1711:
1331:
1167:
966:
877:
There is also potential to harvest hydrocarbons from plants like
846:
series) and as extremely high viscosity shear-resisting liquids.
839:
606:
601:
596:
545:
540:
535:
476:
471:
421:
214:
132:
116:
104:
100:
92:
36:
2181:"TROPOSPHERIC CHEMISTRY AND COMPOSITION (Aromatic Hydrocarbons)"
5117:
4759:
4678:
4578:
4527:
4101:
4096:
4076:
4036:
3976:
3971:
3966:
3956:
3946:
3907:
3834:
3612:
3607:
3602:
3592:
3582:
3572:
3537:
3487:
3465:
3402:
3398:
3385:
3374:
3326:
3273:
3258:
3232:
3212:
3202:
3189:
2810:
2283:"Hydrocarbons from plants: Analytical methods and observations"
1995:
1946:
space probe. Hydrocarbons are also abundant in nebulae forming
1937:
1327:
917:
850:
696:
691:
686:
666:
661:
656:
636:
631:
626:
576:
571:
566:
515:
509:
504:
448:
443:
400:
394:
388:
378:
Variations on hydrocarbons based on the number of carbon atoms
338:
313:
112:
108:
76:
48:
294:. Chiral saturated hydrocarbons constitute the side chains of
4443:
4409:
4325:
3431:
3419:
3394:
3336:
3296:
3292:
3066:
1963:
1876:
1140:
362:
120:
87:; their odor is usually faint, and may be similar to that of
2225:
253:
is the number of rings. Those with exactly one ring are the
5098:
3461:
3437:
3425:
3366:
3356:
3332:
3322:
3238:
3228:
3218:
3208:
3198:
2666:"Microbial Degradation of Alkanes (PDF Download Available)"
1884:
1715:
803:
163:
16:
Organic compound consisting entirely of hydrogen and carbon
2342:
Environmental
Science and Pollution Research International
1928:
Some hydrocarbons also are widespread and abundant in the
4995:
3312:
3282:
2586:
NASA's
Cassini Spacecraft Reveals Clues About Saturn Moon
1835:
1813:
1793:
1755:
1742:
1680:
1647:
1626:
1516:
1490:
1469:
1418:
1398:
1382:
1357:
827:
96:
1932:. Lakes of liquid methane and ethane have been found on
802:
The predominant use of hydrocarbons is as a combustible
2949:
Mycelium
Running: How Mushrooms Can Help Save the World
1985:
largest sources of hydrocarbon contamination of soil.
2972:
2869:
1727:
1549:
1455:
1343:
1233:(olefin metathesis), and for a triple C–C bond it is
2121:
Chemistry: The
Molecular Nature Of Matter and Change
2695:Rohrbacher, Fanny; St-Arnaud, Marc (9 March 2016).
2694:
333:(assuming non-cyclic structures). Those containing
4984:
2942:
2118:
1844:
1689:
1525:
1427:
2612:Monthly Notices of the Royal Astronomical Society
2417:
209:and are saturated with hydrogen. The formula for
192:International Union of Pure and Applied Chemistry
5132:
2460:
2194:
965:The resulting ethylbenzene is dehydrogenated to
786:are one way hydrocarbons are processed for use.
365:, which are hydrocarbons that have at least one
3536:
341:. Those with one triple bond have the formula C
4970:
3503:
3180:
3166:
2228:"Cuticular Hydrocarbons in the Stingless Bee
1958:Burning hydrocarbons as fuel, which produces
1240:
2740:, CRC Press, pp. 353–360, 9 June 2000,
2525:
2143:
2114:
2112:
2110:
2108:
2106:
2104:
1174:by opening of the multiple bonds to produce
980:
83:. Hydrocarbons are generally colourless and
2608:"PAH formation in O-rich planetary nebulae"
1888:
1875:The vast majority of hydrocarbons found on
4977:
4963:
3510:
3496:
3173:
3159:
1966:, is a major contributor to anthropogenic
1150:
257:. Saturated hydrocarbons are the basis of
198:, hydrocarbons are classified as follows:
2883:
2846:
2836:
2767:
2712:
2641:
2623:
2443:
2369:
2250:
2101:
1824:
1802:
1779:
1773:
1505:
1407:
1371:
2483:Clayden, J., Greeves, N., et al. (2001)
2202:"Benzene global market volume 2015-2026"
1972:
1859:
793:
778:
27:
2940:
2914:
2508:5th ed. Brooks/Cole: Thomson Learning.
2270:from the original on 26 September 2015.
1953:
822:, lubricating indices, boiling points,
5133:
2528:Reviews in Mineralogy and Geochemistry
2327:
2280:
2219:
4958:
3491:
3154:
2930:from the original on 31 October 2014.
2917:"6 ways mushrooms can save the world"
2676:from the original on 24 February 2017
1940:'s largest moon, as confirmed by the
3073:
2738:Bioremediation of Contaminated Soils
969:and then polymerized to manufacture
2123:. New York: McGraw-Hill Companies.
2008:or breaking down of hydrocarbon by
1977:Mechanisms involved in hydrocarbon
13:
2560:
2178:
1256:
14:
5152:
1988:
196:nomenclature of organic chemistry
3517:
3133:
3116:
3099:
3082:
3054:
3042:
3030:
3018:
3006:
2994:
2982:
2563:"Hydrocarbons in the Atmosphere"
2398:Canadian Electricity Association
1205:
2934:
2908:
2863:
2804:
2790:10.1016/j.marpolbul.2016.04.023
2761:
2729:
2688:
2658:
2599:
2579:
2554:
2519:
2498:
2477:
2338:from a long-term polluted site"
2239:Genetics and Molecular Research
2004:can also degrade hydrocarbons.
1948:polycyclic aromatic hydrocarbon
905:
290:, branched hydrocarbons can be
79:. Hydrocarbons are examples of
2411:
2386:
2321:
2274:
2172:
2137:
1796:
1666:
1654:
1629:
1493:
1385:
1229:, for a double C–C bond it is
1170:and some alkynes also undergo
213:saturated hydrocarbons (i.e.,
154:refers to naturally occurring
1:
5084:List of natural gas pipelines
5079:Black powder in gas pipelines
3445:ordinary Greek/Latin prefixes
2094:
1438:In inadequate supply of air,
1284:
1216:
282:. As given in the example of
5113:Intermodal freight transport
2894:10.1016/j.copbio.2007.04.006
2838:10.1371/journal.pone.0015399
1273:
896:
7:
2951:. Ten Speed Press. p.
2328:Pawlik, Malgorzata (2017).
2119:Silberberg, Martin (2004).
2045:
1245:
1221:Some hydrocarbons undergo
1196:Shell higher olefin process
1147:are illustrative reagents.
1128:
842:), wood preservatives (the
178:released by the burning of
10:
5157:
2596:. NASA (12 December 2013).
2445:10.1016/j.ngib.2016.02.001
2230:Schwarziana quadripunctata
2144:Meierhenrich, Uwe (2008).
2053:Abiogenic petroleum origin
2023:
2001:Lutibacterium anuloederans
1718:flame when heated in air:
1288:
1277:
1266:
1260:
1249:
1241:High-temperature reactions
1209:
1160:
1154:
1132:
984:
909:
867:Schwarziana quadripunctata
18:
5097:
5032:
4994:
4921:
4883:
4857:
4822:
4778:
4750:
4713:
4704:
4671:
4643:
4634:
4614:
4577:
4568:
4550:
4485:
4442:
4433:
4422:
4377:
4324:
4271:
4253:
4213:
4160:
4115:
4059:
4035:
3985:
3929:
3906:
3893:
3873:
3805:
3774:
3734:
3681:
3621:
3560:
3525:
3454:
3412:
3384:
3346:
3272:
3188:
3182:Organic chemistry affixes
2770:Marine Pollution Bulletin
2362:10.1007/s11356-017-9496-1
2019:
1855:
1297:electric power generation
987:Free-radical halogenation
981:Free-radical substitution
742:
712:
682:
652:
622:
592:
562:
531:
500:
467:
439:
417:
410:
405:
399:
393:
387:
382:
2746:10.1201/9781482270235-27
2592:2 September 2014 at the
2394:"Generating Electricity"
774:
310:Unsaturated hydrocarbons
185:
19:Not to be confused with
2714:10.3390/agronomy6010019
2281:Calvin, Melvin (1980).
2088:Organic nuclear reactor
2073:Fractional distillation
1190:polymerizes to produce
1151:Addition polymerization
71:consisting entirely of
51:, which contain single
43:. Methane is part of a
4845:1,3,5-Triheptylbenzene
2941:Stamets, Paul (2005).
2915:Stamets, Paul (2008).
2872:Curr. Opin. Biotechnol
2548:10.2138/rmg.2013.75.14
2424:Natural Gas Industry B
1981:
1872:
1864:Natural oil spring in
1846:
1691:
1527:
1429:
799:
791:
56:
5089:List of LNG terminals
5024:List of oil pipelines
4840:1,3,5-Triethylbenzene
2252:10.4238/vol8-2kerr012
2026:Hydrocarbon poisoning
1976:
1863:
1847:
1692:
1536:And finally, for any
1528:
1430:
1267:Further information:
1161:Further information:
1001:free-radical pathways
912:Substitution reaction
872:cuticular hydrocarbon
797:
782:
359:Aromatic hydrocarbons
268:chlorination reaction
31:
4243:Isopropylcyclohexene
3825:Perhydrophenanthrene
3764:Isopropylcyclohexane
3413:Counting axial atoms
2643:10.1093/mnras/stu454
2504:McMurry, J. (2000).
2150:. Berlin: Springer.
2083:Hydrocarbon mixtures
1954:Environmental impact
1725:
1547:
1453:
1341:
1334:, burns as follows:
1252:Cracking (chemistry)
1052:carbon tetrachloride
33:Ball-and-stick model
5074:Natural gas storage
4939:Alicyclic compounds
4752:Tetramethylbenzenes
2829:2010PLoSO...515399M
2782:2016MarPB.109...14L
2634:2014MNRAS.441..364G
2540:2013RvMG...75..449S
2436:2016NGIB....3....1Z
2354:2017ESPR...2419640P
2348:(24): 19640–19652.
2299:1980NW.....67..525C
2287:Naturwissenschaften
1837:
1815:
1795:
1757:
1744:
1682:
1649:
1628:
1540:of n carbon atoms,
1518:
1492:
1471:
1420:
1400:
1384:
1359:
830:that remain as the
379:
276:structural formulae
168:commodity chemicals
5108:Industrial railway
4896:Cyclopropenylidene
4233:Methylcyclopentene
4223:Methylcyclopropene
3754:Methylcyclopentane
3744:Methylcyclopropane
3443:(and the rest are
2707:(1). MDPI AG: 19.
2332:Lotus corniculatus
2307:10.1007/BF00450661
1982:
1873:
1842:
1825:
1803:
1783:
1762:
1745:
1732:
1687:
1670:
1637:
1616:
1523:
1506:
1480:
1475:
1459:
1425:
1408:
1388:
1372:
1363:
1347:
1046:all the way to CCl
880:Euphorbia lathyris
800:
792:
377:
320:have the formula C
280:structural isomers
190:As defined by the
57:
5126:
5125:
5068:
5061:
5054:
4952:
4951:
4917:
4916:
4853:
4852:
4830:Hexamethylbenzene
4818:
4817:
4700:
4699:
4645:Trimethylbenzenes
4630:
4629:
4546:
4545:
4418:
4417:
4405:Cyclododecatriene
4400:Cyclooctatetraene
4238:Methylcyclohexene
4228:Methylcyclobutene
4215:Alkylcycloalkenes
4156:
4155:
4031:
4030:
3889:
3888:
3759:Methylcyclohexane
3749:Methylcyclobutane
3736:Alkylcycloalkanes
3677:
3676:
3485:
3484:
2944:"Mycoremediation"
2755:978-0-429-07804-0
2516:. pp. 75–81.
2506:Organic Chemistry
2485:Organic Chemistry
2336:Oenothera biennis
2157:978-3-540-76886-9
2058:Biomass to liquid
1840:
1828:
1806:
1786:
1781:
1761:
1748:
1735:
1730:
1685:
1673:
1640:
1619:
1609:
1566:
1554:
1521:
1509:
1498:
1483:
1474:
1462:
1458:
1423:
1411:
1391:
1375:
1362:
1350:
1346:
1309:electrical energy
1235:alkyne metathesis
1231:alkene metathesis
1227:alkane metathesis
1135:Addition reaction
1005:homolytic fission
886:E. tirucalli
772:
771:
485:(methylacetylene)
316:. Those with one
272:molecular formula
81:group 14 hydrides
61:organic chemistry
45:homologous series
5148:
5064:
5057:
5050:
4979:
4972:
4965:
4956:
4955:
4909:-Propenylbenzene
4711:
4710:
4641:
4640:
4575:
4574:
4566:
4565:
4440:
4439:
4431:
4430:
4116:Branched alkynes
4057:
4056:
3986:Branched alkenes
3927:
3926:
3904:
3903:
3807:Polycycloalkanes
3792:(bicycloheptane)
3786:(bicyclopentane)
3622:Branched alkanes
3558:
3557:
3534:
3533:
3512:
3505:
3498:
3489:
3488:
3175:
3168:
3161:
3152:
3151:
3146:
3138:
3137:
3136:
3129:
3121:
3120:
3119:
3112:
3104:
3103:
3102:
3095:
3087:
3086:
3085:
3075:
3059:
3058:
3047:
3046:
3035:
3034:
3033:
3023:
3022:
3021:
3011:
3010:
3009:
2999:
2998:
2987:
2986:
2985:
2978:
2967:
2966:
2946:
2938:
2932:
2931:
2921:
2912:
2906:
2905:
2887:
2867:
2861:
2860:
2850:
2840:
2808:
2802:
2801:
2765:
2759:
2758:
2733:
2727:
2726:
2716:
2692:
2686:
2685:
2683:
2681:
2662:
2656:
2655:
2645:
2627:
2603:
2597:
2583:
2577:
2576:
2574:
2572:
2567:
2558:
2552:
2551:
2523:
2517:
2502:
2496:
2481:
2475:
2464:
2458:
2457:
2447:
2415:
2409:
2408:
2406:
2404:
2390:
2384:
2383:
2373:
2325:
2319:
2318:
2278:
2272:
2271:
2269:
2254:
2236:
2223:
2217:
2216:
2214:
2212:
2198:
2192:
2191:
2189:
2187:
2176:
2170:
2169:
2141:
2135:
2134:
2116:
2078:Functional group
1979:phytoremediation
1902:
1899:
1896:
1893:
1890:
1851:
1849:
1848:
1843:
1841:
1838:
1836:
1833:
1826:
1820:
1814:
1811:
1804:
1794:
1791:
1784:
1782:
1780:
1774:
1768:
1763:
1759:
1758:
1756:
1753:
1746:
1743:
1740:
1733:
1696:
1694:
1693:
1688:
1686:
1683:
1681:
1678:
1671:
1650:
1648:
1645:
1638:
1632:
1627:
1624:
1617:
1614:
1610:
1605:
1591:
1582:
1581:
1567:
1564:
1561:
1560:
1555:
1552:
1532:
1530:
1529:
1524:
1522:
1519:
1517:
1514:
1507:
1496:
1491:
1488:
1481:
1476:
1472:
1470:
1467:
1460:
1434:
1432:
1431:
1426:
1424:
1421:
1419:
1416:
1409:
1399:
1396:
1389:
1383:
1380:
1373:
1364:
1360:
1358:
1355:
1348:
1322:and heat during
1163:Addition polymer
1123:hexachloroethane
1113:all the way to C
961:
380:
376:
361:, also known as
172:greenhouse gases
69:organic compound
5156:
5155:
5151:
5150:
5149:
5147:
5146:
5145:
5131:
5130:
5127:
5122:
5093:
5028:
4990:
4983:
4953:
4948:
4944:Petroleum jelly
4913:
4901:Phenylacetylene
4879:
4849:
4814:
4810:Isobutylbenzene
4774:
4746:
4696:
4667:
4626:
4610:
4564:
4542:
4481:
4425:
4414:
4373:
4320:
4267:
4249:
4209:
4152:
4111:
4053:
4045:
4039:
4027:
3981:
3923:
3916:
3910:
3899:
3897:
3885:
3869:
3801:
3798:(bicyclodecane)
3770:
3730:
3673:
3639:3-Methylpentane
3617:
3554:
3546:
3540:
3529:
3527:
3521:
3516:
3486:
3481:
3450:
3408:
3380:
3342:
3307:carboxylic acid
3268:
3184:
3179:
3149:
3139:
3134:
3132:
3122:
3117:
3115:
3105:
3100:
3098:
3088:
3083:
3081:
3078:
3074:sister projects
3071:at Knowledge's
3065:
3053:
3041:
3031:
3029:
3019:
3017:
3007:
3005:
2993:
2983:
2981:
2973:
2971:
2970:
2963:
2939:
2935:
2919:
2913:
2909:
2885:10.1.1.475.3300
2868:
2864:
2809:
2805:
2766:
2762:
2756:
2735:
2734:
2730:
2693:
2689:
2679:
2677:
2664:
2663:
2659:
2604:
2600:
2594:Wayback Machine
2584:
2580:
2570:
2568:
2565:
2559:
2555:
2524:
2520:
2503:
2499:
2482:
2478:
2465:
2461:
2416:
2412:
2402:
2400:
2392:
2391:
2387:
2326:
2322:
2293:(11): 525–533.
2279:
2275:
2267:
2234:
2224:
2220:
2210:
2208:
2200:
2199:
2195:
2185:
2183:
2177:
2173:
2158:
2142:
2138:
2131:
2117:
2102:
2097:
2092:
2048:
2028:
2022:
2006:Mycoremediation
1991:
1956:
1943:Cassini–Huygens
1900:
1897:
1894:
1891:
1858:
1834:
1829:
1816:
1812:
1807:
1792:
1787:
1775:
1769:
1767:
1754:
1749:
1741:
1736:
1731:
1729:
1728:
1726:
1723:
1722:
1702:rancidification
1679:
1674:
1669:
1646:
1641:
1636:
1625:
1620:
1615:
1592:
1590:
1586:
1568:
1563:
1562:
1556:
1551:
1550:
1548:
1545:
1544:
1515:
1510:
1489:
1484:
1468:
1463:
1457:
1456:
1454:
1451:
1450:
1417:
1412:
1397:
1392:
1381:
1376:
1356:
1351:
1345:
1344:
1342:
1339:
1338:
1293:
1287:
1282:
1276:
1271:
1269:Steam reforming
1265:
1263:Dehydrogenation
1259:
1257:Dehydrogenation
1254:
1248:
1243:
1219:
1214:
1208:
1165:
1159:
1153:
1137:
1131:
1120:
1116:
1108:
1104:
1100:
1096:
1092:
1088:
1084:
1077:
1073:
1069:
1065:
1061:
1049:
1041:
1037:
1033:
1029:
1022:
1018:
1014:
989:
983:
960:
956:
952:
948:
944:
940:
936:
932:
928:
914:
908:
899:
834:in a crude oil
832:lowest fraction
777:
384:
354:
346:
332:
325:
286:and its higher
259:petroleum fuels
248:
236:
230:
222:
188:
119:), low melting
42:
24:
17:
12:
11:
5:
5154:
5144:
5143:
5124:
5123:
5121:
5120:
5115:
5110:
5104:
5102:
5095:
5094:
5092:
5091:
5086:
5081:
5076:
5071:
5070:
5069:
5066:Gas separation
5062:
5055:
5052:Regasification
5042:
5040:
5030:
5029:
5027:
5026:
5021:
5016:
5011:
5006:
5000:
4998:
4992:
4991:
4982:
4981:
4974:
4967:
4959:
4950:
4949:
4947:
4946:
4941:
4936:
4931:
4925:
4923:
4919:
4918:
4915:
4914:
4912:
4911:
4903:
4898:
4893:
4887:
4885:
4881:
4880:
4878:
4877:
4875:4-Vinyltoluene
4872:
4870:Divinylbenzene
4867:
4861:
4859:
4855:
4854:
4851:
4850:
4848:
4847:
4842:
4837:
4835:2-Phenylhexane
4832:
4826:
4824:
4820:
4819:
4816:
4815:
4813:
4812:
4807:
4799:
4791:
4782:
4780:
4776:
4775:
4773:
4772:
4767:
4762:
4756:
4754:
4748:
4747:
4745:
4744:
4736:
4728:
4719:
4717:
4708:
4702:
4701:
4698:
4697:
4695:
4694:
4692:4-Ethyltoluene
4689:
4687:-Propylbenzene
4681:
4675:
4673:
4669:
4668:
4666:
4665:
4660:
4655:
4649:
4647:
4638:
4632:
4631:
4628:
4627:
4625:
4624:
4618:
4616:
4612:
4611:
4609:
4608:
4600:
4592:
4583:
4581:
4572:
4563:
4562:
4556:
4554:
4548:
4547:
4544:
4543:
4541:
4540:
4535:
4530:
4525:
4520:
4515:
4510:
4505:
4500:
4495:
4489:
4487:
4483:
4482:
4480:
4479:
4474:
4469:
4464:
4459:
4454:
4448:
4446:
4437:
4428:
4420:
4419:
4416:
4415:
4413:
4412:
4407:
4402:
4397:
4392:
4387:
4381:
4379:
4375:
4374:
4372:
4371:
4366:
4361:
4356:
4351:
4346:
4341:
4336:
4330:
4328:
4322:
4321:
4319:
4318:
4313:
4308:
4303:
4298:
4293:
4288:
4283:
4277:
4275:
4269:
4268:
4266:
4265:
4259:
4257:
4255:Bicycloalkenes
4251:
4250:
4248:
4247:
4245:
4240:
4235:
4230:
4225:
4219:
4217:
4211:
4210:
4208:
4207:
4202:
4197:
4192:
4187:
4182:
4177:
4172:
4166:
4164:
4158:
4157:
4154:
4153:
4151:
4150:
4145:
4140:
4135:
4130:
4125:
4119:
4117:
4113:
4112:
4110:
4109:
4104:
4099:
4094:
4089:
4084:
4079:
4074:
4069:
4063:
4061:
4060:Linear alkynes
4054:
4047:
4041:
4033:
4032:
4029:
4028:
4026:
4025:
4020:
4015:
4010:
4005:
4000:
3995:
3989:
3987:
3983:
3982:
3980:
3979:
3974:
3969:
3964:
3959:
3954:
3949:
3944:
3939:
3933:
3931:
3930:Linear alkenes
3924:
3918:
3912:
3901:
3891:
3890:
3887:
3886:
3884:
3883:
3877:
3875:
3871:
3870:
3868:
3867:
3862:
3857:
3852:
3847:
3842:
3837:
3832:
3827:
3822:
3817:
3811:
3809:
3803:
3802:
3800:
3799:
3793:
3787:
3780:
3778:
3776:Bicycloalkanes
3772:
3771:
3769:
3768:
3766:
3761:
3756:
3751:
3746:
3740:
3738:
3732:
3731:
3729:
3728:
3723:
3718:
3713:
3708:
3703:
3698:
3693:
3687:
3685:
3679:
3678:
3675:
3674:
3672:
3671:
3666:
3661:
3656:
3651:
3646:
3641:
3636:
3631:
3625:
3623:
3619:
3618:
3616:
3615:
3610:
3605:
3600:
3595:
3590:
3585:
3580:
3575:
3570:
3564:
3562:
3561:Linear alkanes
3555:
3548:
3542:
3531:
3523:
3522:
3515:
3514:
3507:
3500:
3492:
3483:
3482:
3480:
3479:
3469:
3458:
3456:
3452:
3451:
3449:
3448:
3441:
3435:
3429:
3423:
3416:
3414:
3410:
3409:
3407:
3406:
3391:
3389:
3382:
3381:
3379:
3378:
3364:
3353:
3351:
3344:
3343:
3341:
3340:
3330:
3320:
3310:
3300:
3290:
3279:
3277:
3270:
3269:
3267:
3266:
3256:
3246:
3236:
3226:
3216:
3206:
3195:
3193:
3186:
3185:
3178:
3177:
3170:
3163:
3155:
3148:
3147:
3130:
3128:from Wikibooks
3113:
3111:from Wikiquote
3096:
3067:
3064:
3063:
3061:Global warming
3051:
3039:
3027:
3015:
3003:
2991:
2969:
2968:
2961:
2933:
2907:
2878:(3): 257–266.
2862:
2823:(11): e15399.
2803:
2760:
2754:
2728:
2687:
2657:
2618:(1): 364–377.
2598:
2578:
2553:
2534:(1): 449–465.
2518:
2497:
2476:
2473:979-8353989172
2459:
2410:
2385:
2320:
2273:
2245:(2): 589–595.
2218:
2193:
2171:
2156:
2136:
2129:
2099:
2098:
2096:
2093:
2091:
2090:
2085:
2080:
2075:
2070:
2068:Energy storage
2065:
2060:
2055:
2049:
2047:
2044:
2024:Main article:
2021:
2018:
1996:gabbroic layer
1990:
1989:Bioremediation
1987:
1968:global warming
1960:carbon dioxide
1955:
1952:
1905:methanogenesis
1857:
1854:
1853:
1852:
1832:
1823:
1819:
1810:
1801:
1798:
1790:
1778:
1772:
1766:
1752:
1739:
1698:
1697:
1677:
1668:
1665:
1662:
1659:
1656:
1653:
1644:
1635:
1631:
1623:
1613:
1608:
1604:
1601:
1598:
1595:
1589:
1585:
1580:
1577:
1574:
1571:
1559:
1534:
1533:
1513:
1504:
1501:
1495:
1487:
1479:
1466:
1436:
1435:
1415:
1406:
1403:
1395:
1387:
1379:
1370:
1367:
1354:
1320:carbon dioxide
1289:Main article:
1286:
1283:
1278:Main article:
1275:
1272:
1261:Main article:
1258:
1255:
1250:Main article:
1247:
1244:
1242:
1239:
1218:
1215:
1210:Main article:
1207:
1204:
1172:polymerization
1155:Main article:
1152:
1149:
1133:Main article:
1130:
1127:
1118:
1114:
1111:
1110:
1106:
1102:
1098:
1094:
1090:
1086:
1082:
1079:
1075:
1071:
1067:
1063:
1059:
1047:
1044:
1043:
1039:
1035:
1031:
1027:
1024:
1020:
1016:
1012:
985:Main article:
982:
979:
963:
962:
958:
954:
950:
946:
942:
938:
934:
930:
910:Main article:
907:
904:
898:
895:
824:solidification
784:Oil refineries
776:
773:
770:
769:
764:
759:
754:
749:
744:
740:
739:
734:
729:
724:
719:
714:
710:
709:
704:
699:
694:
689:
684:
680:
679:
674:
669:
664:
659:
654:
650:
649:
644:
639:
634:
629:
624:
620:
619:
614:
609:
604:
599:
594:
590:
589:
584:
579:
574:
569:
564:
560:
559:
553:
548:
543:
538:
533:
529:
528:
523:
518:
513:
507:
502:
498:
497:
491:
486:
480:
474:
469:
465:
464:
461:
458:
452:
446:
441:
437:
436:
433:
430:
427:
424:
419:
415:
414:
409:
404:
403:(triple bond)
398:
397:(double bond)
392:
391:(single bond)
386:
371:
370:
356:
348:
342:
327:
321:
307:
284:3-methylhexane
274:but different
238:
232:
224:
218:
187:
184:
176:carbon dioxide
40:
15:
9:
6:
4:
3:
2:
5153:
5142:
5139:
5138:
5136:
5129:
5119:
5116:
5114:
5111:
5109:
5106:
5105:
5103:
5100:
5096:
5090:
5087:
5085:
5082:
5080:
5077:
5075:
5072:
5067:
5063:
5060:
5056:
5053:
5049:
5048:
5047:
5044:
5043:
5041:
5039:
5035:
5031:
5025:
5022:
5020:
5017:
5015:
5012:
5010:
5007:
5005:
5002:
5001:
4999:
4997:
4993:
4988:
4985:Transport of
4980:
4975:
4973:
4968:
4966:
4961:
4960:
4957:
4945:
4942:
4940:
4937:
4935:
4932:
4930:
4927:
4926:
4924:
4920:
4910:
4908:
4904:
4902:
4899:
4897:
4894:
4892:
4889:
4888:
4886:
4882:
4876:
4873:
4871:
4868:
4866:
4863:
4862:
4860:
4858:Vinylbenzenes
4856:
4846:
4843:
4841:
4838:
4836:
4833:
4831:
4828:
4827:
4825:
4821:
4811:
4808:
4806:
4805:-Butylbenzene
4804:
4800:
4798:
4797:-Butylbenzene
4796:
4792:
4790:
4789:-Butylbenzene
4788:
4784:
4783:
4781:
4777:
4771:
4768:
4766:
4763:
4761:
4758:
4757:
4755:
4753:
4749:
4743:
4741:
4737:
4735:
4733:
4729:
4727:
4725:
4721:
4720:
4718:
4716:
4712:
4709:
4707:
4703:
4693:
4690:
4688:
4686:
4682:
4680:
4677:
4676:
4674:
4670:
4664:
4661:
4659:
4656:
4654:
4651:
4650:
4648:
4646:
4642:
4639:
4637:
4633:
4623:
4620:
4619:
4617:
4613:
4607:
4605:
4601:
4599:
4597:
4593:
4591:
4589:
4585:
4584:
4582:
4580:
4576:
4573:
4571:
4567:
4561:
4558:
4557:
4555:
4553:
4552:Alkylbenzenes
4549:
4539:
4536:
4534:
4531:
4529:
4526:
4524:
4521:
4519:
4516:
4514:
4511:
4509:
4506:
4504:
4501:
4499:
4496:
4494:
4491:
4490:
4488:
4484:
4478:
4475:
4473:
4470:
4468:
4465:
4463:
4460:
4458:
4455:
4453:
4450:
4449:
4447:
4445:
4441:
4438:
4436:
4432:
4429:
4427:
4421:
4411:
4408:
4406:
4403:
4401:
4398:
4396:
4393:
4391:
4388:
4386:
4383:
4382:
4380:
4376:
4370:
4367:
4365:
4362:
4360:
4357:
4355:
4352:
4350:
4347:
4345:
4342:
4340:
4337:
4335:
4332:
4331:
4329:
4327:
4323:
4317:
4314:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4278:
4276:
4274:
4270:
4264:
4261:
4260:
4258:
4256:
4252:
4246:
4244:
4241:
4239:
4236:
4234:
4231:
4229:
4226:
4224:
4221:
4220:
4218:
4216:
4212:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4183:
4181:
4178:
4176:
4173:
4171:
4168:
4167:
4165:
4163:
4159:
4149:
4146:
4144:
4141:
4139:
4136:
4134:
4131:
4129:
4126:
4124:
4121:
4120:
4118:
4114:
4108:
4105:
4103:
4100:
4098:
4095:
4093:
4090:
4088:
4085:
4083:
4080:
4078:
4075:
4073:
4070:
4068:
4065:
4064:
4062:
4058:
4055:
4051:
4044:
4038:
4034:
4024:
4021:
4019:
4016:
4014:
4011:
4009:
4006:
4004:
4001:
3999:
3996:
3994:
3991:
3990:
3988:
3984:
3978:
3975:
3973:
3970:
3968:
3965:
3963:
3960:
3958:
3955:
3953:
3950:
3948:
3945:
3943:
3940:
3938:
3935:
3934:
3932:
3928:
3925:
3922:
3915:
3909:
3905:
3902:
3896:
3892:
3882:
3879:
3878:
3876:
3872:
3866:
3863:
3861:
3858:
3856:
3853:
3851:
3848:
3846:
3845:Dodecahedrane
3843:
3841:
3838:
3836:
3833:
3831:
3828:
3826:
3823:
3821:
3818:
3816:
3813:
3812:
3810:
3808:
3804:
3797:
3794:
3791:
3788:
3785:
3782:
3781:
3779:
3777:
3773:
3767:
3765:
3762:
3760:
3757:
3755:
3752:
3750:
3747:
3745:
3742:
3741:
3739:
3737:
3733:
3727:
3724:
3722:
3719:
3717:
3714:
3712:
3709:
3707:
3704:
3702:
3699:
3697:
3694:
3692:
3689:
3688:
3686:
3684:
3680:
3670:
3667:
3665:
3662:
3660:
3657:
3655:
3652:
3650:
3647:
3645:
3642:
3640:
3637:
3635:
3632:
3630:
3627:
3626:
3624:
3620:
3614:
3611:
3609:
3606:
3604:
3601:
3599:
3596:
3594:
3591:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3571:
3569:
3566:
3565:
3563:
3559:
3556:
3552:
3545:
3539:
3535:
3532:
3524:
3520:
3513:
3508:
3506:
3501:
3499:
3494:
3493:
3490:
3477:
3473:
3470:
3467:
3463:
3460:
3459:
3457:
3453:
3446:
3442:
3439:
3436:
3433:
3430:
3427:
3424:
3421:
3418:
3417:
3415:
3411:
3404:
3400:
3396:
3393:
3392:
3390:
3387:
3383:
3376:
3372:
3368:
3365:
3362:
3358:
3355:
3354:
3352:
3349:
3345:
3338:
3334:
3331:
3328:
3324:
3321:
3318:
3314:
3311:
3308:
3304:
3301:
3298:
3294:
3291:
3288:
3284:
3281:
3280:
3278:
3275:
3271:
3264:
3260:
3257:
3254:
3250:
3247:
3244:
3241:(nonaromatic
3240:
3237:
3234:
3230:
3227:
3224:
3221:(unsaturated
3220:
3217:
3214:
3210:
3207:
3204:
3200:
3197:
3196:
3194:
3191:
3187:
3183:
3176:
3171:
3169:
3164:
3162:
3157:
3156:
3153:
3145:from Wikidata
3144:
3143:
3131:
3127:
3126:
3114:
3110:
3109:
3097:
3093:
3092:
3080:
3079:
3076:
3070:
3062:
3057:
3052:
3050:
3045:
3040:
3038:
3028:
3026:
3016:
3014:
3004:
3002:
2997:
2992:
2990:
2980:
2979:
2976:
2964:
2962:9781580085793
2958:
2954:
2950:
2945:
2937:
2929:
2925:
2918:
2911:
2903:
2899:
2895:
2891:
2886:
2881:
2877:
2873:
2866:
2858:
2854:
2849:
2844:
2839:
2834:
2830:
2826:
2822:
2818:
2814:
2807:
2799:
2795:
2791:
2787:
2783:
2779:
2775:
2771:
2764:
2757:
2751:
2747:
2743:
2739:
2732:
2724:
2720:
2715:
2710:
2706:
2702:
2698:
2691:
2675:
2671:
2667:
2661:
2653:
2649:
2644:
2639:
2635:
2631:
2626:
2621:
2617:
2613:
2609:
2602:
2595:
2591:
2587:
2582:
2564:
2557:
2549:
2545:
2541:
2537:
2533:
2529:
2522:
2515:
2514:0-495-11837-0
2511:
2507:
2501:
2495:, p. 21.
2494:
2493:0-19-850346-6
2490:
2486:
2480:
2474:
2470:
2463:
2455:
2451:
2446:
2441:
2437:
2433:
2429:
2425:
2421:
2414:
2399:
2395:
2389:
2381:
2377:
2372:
2367:
2363:
2359:
2355:
2351:
2347:
2343:
2339:
2337:
2333:
2324:
2316:
2312:
2308:
2304:
2300:
2296:
2292:
2288:
2284:
2277:
2266:
2262:
2258:
2253:
2248:
2244:
2240:
2233:
2231:
2222:
2207:
2203:
2197:
2182:
2175:
2167:
2163:
2159:
2153:
2149:
2148:
2140:
2132:
2130:0-07-310169-9
2126:
2122:
2115:
2113:
2111:
2109:
2107:
2105:
2100:
2089:
2086:
2084:
2081:
2079:
2076:
2074:
2071:
2069:
2066:
2064:
2061:
2059:
2056:
2054:
2051:
2050:
2043:
2041:
2037:
2033:
2027:
2017:
2016:is possible.
2015:
2011:
2007:
2003:
2002:
1997:
1986:
1980:
1975:
1971:
1969:
1965:
1961:
1951:
1949:
1945:
1944:
1939:
1935:
1931:
1926:
1923:
1921:
1916:
1914:
1908:
1906:
1886:
1883:, petroleum,
1882:
1878:
1871:
1867:
1862:
1830:
1821:
1817:
1808:
1799:
1788:
1776:
1770:
1764:
1750:
1737:
1721:
1720:
1719:
1717:
1713:
1709:
1707:
1703:
1675:
1663:
1660:
1657:
1651:
1642:
1633:
1621:
1611:
1606:
1602:
1599:
1596:
1593:
1587:
1583:
1578:
1575:
1572:
1569:
1557:
1543:
1542:
1541:
1539:
1538:linear alkane
1511:
1502:
1499:
1485:
1477:
1464:
1449:
1448:
1447:
1445:
1441:
1413:
1404:
1401:
1393:
1377:
1368:
1365:
1352:
1337:
1336:
1335:
1333:
1329:
1325:
1321:
1316:
1314:
1310:
1306:
1302:
1298:
1292:
1281:
1270:
1264:
1253:
1238:
1236:
1232:
1228:
1224:
1213:
1212:Hydrogenation
1206:Hydrogenation
1203:
1201:
1197:
1193:
1192:polyacetylene
1189:
1186:. The alkyne
1185:
1181:
1177:
1173:
1169:
1164:
1158:
1148:
1146:
1142:
1136:
1126:
1124:
1080:
1057:
1056:
1055:
1053:
1025:
1010:
1009:
1008:
1006:
1002:
998:
994:
988:
978:
976:
975:thermoplastic
972:
968:
927:
926:
925:
923:
919:
913:
903:
894:
892:
888:
887:
882:
881:
875:
873:
870:, use unique
869:
868:
862:
860:
856:
852:
847:
845:
841:
837:
833:
829:
825:
821:
817:
813:
809:
805:
796:
789:
785:
781:
768:
765:
763:
762:Cyclododecane
760:
758:
755:
753:
750:
748:
745:
741:
738:
735:
733:
732:Cycloundecane
730:
728:
725:
723:
720:
718:
715:
711:
708:
705:
703:
700:
698:
695:
693:
690:
688:
685:
681:
678:
675:
673:
670:
668:
665:
663:
660:
658:
655:
651:
648:
645:
643:
640:
638:
635:
633:
630:
628:
625:
621:
618:
615:
613:
610:
608:
605:
603:
600:
598:
595:
591:
588:
585:
583:
580:
578:
575:
573:
570:
568:
565:
561:
558:(piperylene)
557:
554:
552:
549:
547:
544:
542:
539:
537:
534:
530:
527:
524:
522:
519:
517:
514:
511:
508:
506:
503:
499:
495:
492:
490:
487:
484:
481:
478:
475:
473:
470:
466:
462:
459:
456:
453:
450:
447:
445:
442:
438:
434:
431:
428:
425:
423:
420:
416:
413:
408:
402:
396:
390:
385:carbon atoms
381:
375:
368:
367:aromatic ring
364:
360:
357:
352:
345:
340:
336:
331:
324:
319:
315:
311:
308:
305:
301:
297:
293:
289:
285:
281:
277:
273:
269:
265:
260:
256:
252:
246:
242:
235:
228:
221:
216:
212:
208:
204:
201:
200:
199:
197:
193:
183:
181:
177:
173:
169:
165:
161:
157:
153:
149:
144:
142:
138:
134:
130:
126:
122:
118:
114:
110:
106:
102:
98:
94:
93:lighter fluid
90:
86:
82:
78:
74:
70:
66:
62:
54:
50:
47:known as the
46:
38:
34:
30:
26:
22:
5141:Hydrocarbons
5128:
5059:Liquefaction
5009:Oil terminal
4986:
4906:
4802:
4794:
4786:
4739:
4731:
4723:
4684:
4658:Pseudocumene
4622:Ethylbenzene
4603:
4595:
4587:
4518:Phenanthrene
4426:hydrocarbons
4301:Cycloheptyne
4291:Cyclopentyne
4281:Cyclopropyne
4273:Cycloalkynes
4190:Cycloheptene
4180:Cyclopentene
4170:Cyclopropene
4162:Cycloalkenes
4049:
4042:
3920:
3913:
3900:hydrocarbons
3881:Spiroalkanes
3711:Cycloheptane
3701:Cyclopentane
3691:Cyclopropane
3683:Cycloalkanes
3550:
3543:
3530:hydrocarbons
3519:Hydrocarbons
3518:
3242:
3222:
3140:
3123:
3106:
3094:from Commons
3089:
3068:
3013:Solar System
2948:
2936:
2923:
2910:
2875:
2871:
2865:
2820:
2816:
2806:
2776:(1): 14–45.
2773:
2769:
2763:
2737:
2731:
2704:
2700:
2690:
2678:. Retrieved
2670:ResearchGate
2669:
2660:
2615:
2611:
2601:
2581:
2569:. Retrieved
2561:Dewulf, Jo.
2556:
2531:
2527:
2521:
2505:
2500:
2484:
2479:
2462:
2427:
2423:
2413:
2401:. Retrieved
2397:
2388:
2345:
2341:
2335:
2331:
2323:
2290:
2286:
2276:
2242:
2238:
2229:
2221:
2209:. Retrieved
2205:
2196:
2184:. Retrieved
2174:
2146:
2139:
2120:
2063:Carbohydrate
2036:carcinogenic
2029:
1999:
1992:
1983:
1957:
1941:
1930:Solar System
1927:
1924:
1917:
1909:
1874:
1710:
1706:paint drying
1699:
1535:
1446:are formed:
1444:water vapour
1440:carbon black
1437:
1317:
1313:power plants
1294:
1222:
1220:
1180:polybutylene
1176:polyethylene
1166:
1138:
1112:
1045:
990:
964:
922:ethylbenzene
915:
906:Substitution
900:
884:
878:
876:
865:
863:
848:
831:
801:
612:Cycloheptane
551:Cyclopentane
489:Cyclopropane
372:
350:
343:
335:triple bonds
329:
322:
296:biomolecules
255:cycloalkanes
250:
244:
240:
233:
226:
219:
207:single bonds
189:
180:fossil fuels
151:
150:industries,
145:
137:polyethylene
125:paraffin wax
64:
58:
39:molecule, CH
25:
21:Carbohydrate
5046:LNG carrier
4987:hydrocarbon
4706:C4-Benzenes
4663:Hemellitene
4636:C3-Benzenes
4570:C2-Benzenes
4533:Corannulene
4452:Naphthalene
4316:Cyclodecyne
4311:Cyclononyne
4306:Cyclooctyne
4296:Cyclohexyne
4286:Cyclobutyne
4205:Cyclodecene
4200:Cyclononene
4195:Cyclooctene
4185:Cyclohexene
4175:Cyclobutene
3895:Unsaturated
3726:Cyclodecane
3721:Cyclononane
3716:Cyclooctane
3706:Cyclohexane
3696:Cyclobutane
3243:hydrocarbon
3223:hydrocarbon
3069:Hydrocarbon
3049:Engineering
2680:23 February
2430:(1): 1–11.
2179:Barnes, I.
1950:compounds.
1920:abiological
1714:burns with
1305:natural gas
1184:polystyrene
973:, a common
971:polystyrene
820:viscosities
767:Dodecadiene
737:Undecadiene
702:Cyclodecane
672:Cyclononane
642:Cyclooctane
582:Cyclohexane
521:Cyclobutane
479:(propylene)
457:(acetylene)
407:Cycloalkane
337:are called
318:double bond
300:chlorophyll
278:are called
174:are either
160:natural gas
152:hydrocarbon
148:fossil fuel
141:polystyrene
129:naphthalene
85:hydrophobic
65:hydrocarbon
5019:Tank truck
5004:Oil tanker
4765:Prehnitene
4653:Mesitylene
4508:Circulenes
4457:Anthracene
4385:Alkatriene
4354:Heptadiene
4344:Pentadiene
4334:Propadiene
4263:Norbornene
4133:Isoheptyne
4123:Isopentyne
4008:Isoheptene
3998:Isopentene
3820:Diamondoid
3815:Adamantane
3790:Norbornane
3654:Isoheptane
3644:Neopentane
3634:Isopentane
3108:Quotations
2571:26 October
2403:5 December
2211:5 December
2186:26 October
2095:References
1913:metallurgy
1324:combustion
1291:Combustion
1285:Combustion
1223:metathesis
1217:Metathesis
1157:Polyolefin
977:material.
891:endophytic
617:Heptadiene
556:Pentadiene
512:(butylene)
494:Propadiene
451:(ethylene)
304:tocopherol
288:homologues
264:chloroform
4934:Annulynes
4929:Annulenes
4770:Isodurene
4503:Helicenes
4477:Heptacene
4467:Pentacene
4462:Tetracene
4390:Alkadiyne
4369:Decadiene
4364:Nonadiene
4359:Octadiene
4349:Hexadiene
4339:Butadiene
4148:Isodecyne
4143:Isononyne
4138:Isooctyne
4128:Isohexyne
4023:Isodecene
4018:Isononene
4013:Isooctene
4003:Isohexene
3993:Isobutene
3898:aliphatic
3855:Churchane
3850:Basketane
3669:Isodecane
3664:Isononane
3659:Isooctane
3649:Isohexane
3629:Isobutane
3528:aliphatic
3526:Saturated
3401:replaces
3373:replaces
3303:-oic acid
3125:Textbooks
3025:Chemistry
2989:Astronomy
2880:CiteSeerX
2723:2073-4395
2652:118540862
2625:1403.1856
2454:2352-8540
2166:288470227
2040:flammable
2014:mushrooms
1881:crude oil
1879:occur in
1797:⟶
1630:⟶
1494:⟶
1386:⟶
1326:and that
1301:petroleum
1280:Pyrolysis
1274:Pyrolysis
1200:α-olefins
1188:acetylene
897:Reactions
859:propylene
788:Crude oil
707:Decadiene
677:Nonadiene
647:Octadiene
587:Hexadiene
526:Butadiene
496:(allene)
412:Alkadiene
383:Number of
203:Saturated
156:petroleum
135:(such as
123:(such as
111:(such as
99:(such as
5135:Category
5014:Tank car
4538:Kekulene
4523:Chrysene
4513:Butalene
4498:Fluorene
4472:Hexacene
4424:Aromatic
4395:Cumulene
3865:Twistane
3860:Pagodane
3840:Prismane
3361:alkaloid
3348:Nitrogen
3287:aldehyde
3253:aromatic
2928:Archived
2924:TED Talk
2902:17493798
2857:21079766
2817:PLOS ONE
2798:27267117
2701:Agronomy
2674:Archived
2590:Archived
2380:28681302
2315:40660980
2265:Archived
2261:19551647
2206:Statista
2046:See also
2010:mycelium
1898:rock oil
1870:Slovakia
1246:Cracking
1198:, where
1145:hydrogen
1129:Addition
1078:Cl + HCl
1023:Cl + HCl
997:fluorine
993:chlorine
920:to give
855:ethylene
844:creosote
836:refining
816:jet fuel
808:gasoline
757:Dodecyne
752:Dodecene
747:Dodecane
727:Undecyne
722:Undecene
717:Undecane
298:such as
266:using a
249:, where
133:polymers
89:gasoline
73:hydrogen
4891:Benzene
4865:Styrene
4742:-Cymene
4734:-Cymene
4726:-Cymene
4715:Cymenes
4606:-Xylene
4598:-Xylene
4590:-Xylene
4579:Xylenes
4560:Toluene
4493:Azulene
4092:Heptyne
4082:Pentyne
4072:Propyne
4037:Alkynes
3962:Heptene
3952:Pentene
3942:Propene
3908:Alkenes
3830:Sterane
3796:Decalin
3784:Housane
3598:Heptane
3588:Pentane
3578:Propane
3568:Methane
3538:Alkanes
3476:radical
3317:alcohol
2975:Portals
2920:(video)
2848:2974637
2825:Bibcode
2778:Bibcode
2630:Bibcode
2536:Bibcode
2487:Oxford
2432:Bibcode
2371:5570797
2350:Bibcode
2295:Bibcode
2032:toluene
1892:
1760:benzene
1712:Benzene
1473:methane
1361:methane
1332:methane
1168:Alkenes
1030:Cl + Cl
967:styrene
840:bitumen
812:naphtha
607:Heptyne
602:Heptene
597:Heptane
546:Pentyne
541:Pentene
536:Pentane
483:Propyne
477:Propene
472:Propane
422:Methane
314:alkenes
215:alkanes
211:acyclic
146:In the
117:benzene
109:liquids
105:propane
101:methane
49:alkanes
37:methane
35:of the
5118:Syngas
5101:/misc.
4760:Durene
4679:Cumene
4528:Pyrene
4444:Acenes
4326:Dienes
4107:Decyne
4102:Nonyne
4097:Octyne
4087:Hexyne
4077:Butyne
4067:Ethyne
3977:Decene
3972:Nonene
3967:Octene
3957:Hexene
3947:Butene
3937:Ethene
3835:Cubane
3613:Decane
3608:Nonane
3603:Octane
3593:Hexane
3583:Butane
3573:Ethane
3466:enzyme
3388:-based
3386:Sulfur
3350:-based
3327:ketone
3276:-based
3274:Oxygen
3263:cyclic
3259:cyclo-
3233:alkyne
3213:alkene
3203:alkane
3192:-based
3190:Carbon
3001:Energy
2959:
2900:
2882:
2855:
2845:
2796:
2752:
2721:
2650:
2512:
2491:
2471:
2452:
2378:
2368:
2313:
2259:
2164:
2154:
2127:
2020:Safety
1938:Saturn
1856:Origin
1328:oxygen
1182:, and
1143:, and
918:ethene
853:or to
851:syngas
697:Decyne
692:Decene
687:Decane
667:Nonyne
662:Nonene
657:Nonane
637:Octyne
632:Octene
627:Octane
577:Hexyne
572:Hexene
567:Hexane
516:Butyne
510:Butene
505:Butane
455:Ethyne
449:Ethene
444:Ethane
401:Alkyne
395:Alkene
389:Alkane
363:arenes
339:alkyne
292:chiral
217:) is C
121:solids
113:hexane
77:carbon
67:is an
4989:fuels
4922:Other
4907:trans
4884:Other
4823:Other
4779:Other
4672:Other
4615:Other
4486:Other
4410:Enyne
4378:Other
3874:Other
3455:Other
3432:prop-
3420:meth-
3395:thio-
3337:sugar
3297:ester
3293:-oate
3091:Media
3037:Space
2648:S2CID
2620:arXiv
2566:(PDF)
2311:S2CID
2268:(PDF)
2235:(PDF)
1964:water
1934:Titan
1877:Earth
1866:Korňa
1716:sooty
1141:water
1109:+ HCl
1042:+ HCl
775:Usage
243:+2(1-
186:Types
131:) or
97:gases
55:only.
53:bonds
5099:Coal
5036:and
4803:tert
4435:PAHs
3462:-ase
3438:but-
3426:eth-
3367:aza-
3357:-ine
3333:-ose
3323:-one
3239:alk-
3229:-yne
3219:-ine
3209:-ene
3199:-ane
3142:Data
2957:ISBN
2898:PMID
2853:PMID
2794:PMID
2750:ISBN
2719:ISSN
2682:2017
2573:2020
2510:ISBN
2489:ISBN
2469:ISBN
2450:ISSN
2405:2021
2376:PMID
2334:and
2257:PMID
2213:2021
2188:2020
2162:OCLC
2152:ISBN
2125:ISBN
2012:and
1962:and
1889:lit.
1885:coal
1704:and
1442:and
1093:+ Cl
1066:+ Cl
1034:→ CH
1019:→ CH
1015:+ Cl
995:and
945:→ C
883:and
857:and
828:tars
804:fuel
302:and
164:coal
162:and
139:and
127:and
115:and
103:and
75:and
63:, a
5038:LPG
5034:LNG
4996:Oil
4795:sec
4052:− 2
3553:+ 2
3472:-yl
3440:(4)
3434:(3)
3428:(2)
3422:(1)
3313:-ol
3283:-al
3249:ar-
2890:doi
2843:PMC
2833:doi
2786:doi
2774:109
2742:doi
2709:doi
2638:doi
2616:441
2544:doi
2440:doi
2366:PMC
2358:doi
2303:doi
2247:doi
1311:in
1303:or
1097:→ C
1070:→ C
1007:).
937:+ C
743:12
713:11
683:10
194:'s
143:).
107:),
91:or
59:In
5137::
2955:.
2953:86
2947:.
2926:.
2922:.
2896:.
2888:.
2876:18
2874:.
2851:.
2841:.
2831:.
2819:.
2815:.
2792:.
2784:.
2772:.
2748:,
2717:.
2703:.
2699:.
2672:.
2668:.
2646:.
2636:.
2628:.
2614:.
2610:.
2588:.
2542:.
2532:75
2530:.
2448:.
2438:.
2426:.
2422:.
2396:.
2374:.
2364:.
2356:.
2346:24
2344:.
2340:.
2309:.
2301:.
2291:67
2289:.
2285:.
2263:.
2255:.
2241:.
2237:.
2204:.
2160:.
2103:^
2042:.
1936:,
1922:.
1915:.
1907:.
1868:,
1805:CO
1771:15
1708:.
1639:CO
1461:CH
1390:CO
1349:CH
1315:.
1237:.
1178:,
1125:)
1117:Cl
1105:Cl
1089:Cl
1054:)
1038:Cl
1026:CH
1011:CH
957:CH
953:CH
924::
814:,
810:,
653:9
623:8
593:7
563:6
532:5
501:4
468:3
463:—
440:2
435:—
418:1
353:−2
229:+2
158:,
4978:e
4971:t
4964:v
4787:n
4740:p
4732:m
4724:o
4685:n
4604:p
4596:m
4588:o
4050:n
4048:2
4046:H
4043:n
4040:C
3921:n
3919:2
3917:H
3914:n
3911:C
3551:n
3549:2
3547:H
3544:n
3541:C
3511:e
3504:t
3497:v
3478:)
3474:(
3468:)
3464:(
3447:)
3405:)
3403:O
3399:S
3397:(
3377:)
3375:C
3371:N
3369:(
3363:)
3359:(
3339:)
3335:(
3329:)
3325:(
3319:)
3315:(
3309:)
3305:(
3299:)
3295:(
3289:)
3285:(
3265:)
3261:(
3255:)
3251:(
3245:)
3235:)
3231:(
3225:)
3215:)
3211:(
3205:)
3201:(
3174:e
3167:t
3160:v
3077::
2977::
2965:.
2904:.
2892::
2859:.
2835::
2827::
2821:5
2800:.
2788::
2780::
2744::
2725:.
2711::
2705:6
2684:.
2654:.
2640::
2632::
2622::
2575:.
2550:.
2546::
2538::
2456:.
2442::
2434::
2428:3
2407:.
2382:.
2360::
2352::
2317:.
2305::
2297::
2249::
2243:8
2215:.
2190:.
2168:.
2133:.
1901:'
1895:'
1839:O
1831:2
1827:H
1822:3
1818:+
1809:2
1800:6
1789:2
1785:O
1777:2
1765:+
1751:6
1747:H
1738:6
1734:C
1684:O
1676:2
1672:H
1667:)
1664:1
1661:+
1658:n
1655:(
1652:+
1643:2
1634:n
1622:2
1618:O
1612:)
1607:2
1603:1
1600:+
1597:n
1594:3
1588:(
1584:+
1579:2
1576:+
1573:n
1570:2
1565:H
1558:n
1553:C
1520:O
1512:2
1508:H
1503:2
1500:+
1497:C
1486:2
1482:O
1478:+
1465:4
1422:O
1414:2
1410:H
1405:2
1402:+
1394:2
1378:2
1374:O
1369:2
1366:+
1353:4
1121:(
1119:6
1115:2
1107:3
1103:3
1101:H
1099:2
1095:2
1091:2
1087:4
1085:H
1083:2
1081:C
1076:5
1074:H
1072:2
1068:2
1064:6
1062:H
1060:2
1058:C
1050:(
1048:4
1040:2
1036:2
1032:2
1028:3
1021:3
1017:2
1013:4
959:3
955:2
951:5
949:H
947:6
943:4
941:H
939:2
935:6
933:H
931:6
929:C
460:—
432:—
429:—
426:—
355:.
351:n
349:2
347:H
344:n
330:n
328:2
326:H
323:n
306:.
251:r
247:)
245:r
241:n
239:2
237:H
234:n
227:n
225:2
223:H
220:n
41:4
23:.
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