Pentene

n-Pentene

1-Pentene

cis-2-Pentene

trans-2-Pentene

Names
IUPAC names

Pent-1-ene
cis-Pent-2-ene
trans-Pent-2-ene

Other names

amylene, n-amylene, n-pentene, beta-n-amylene, sym-methylethylethylene, pentylene

Identifiers

CAS Number

* 109-67-1 (1-pentene) Y
* 627-20-3 (cis-2-pentene) Y
* 646-04-8 (trans-2-pentene) Y

3D model (JSmol)

* (1-pentene): Interactive image
* (cis-2-pentene): Interactive image
* (trans-2-pentene): Interactive image

ChemSpider |

* 7713 (1-pentene) N
* 4483638 (cis-2-pentene) N
* 4483639 (trans-2-pentene) N

EC Number |

* 246-916-6 (1-pentene)

273-308-8 (cis-2-pentene)

271-255-5 (trans-2-pentene)

PubChem CID

* 8004 (1-pentene)
* 5326160 (cis-2-pentene)
* 5326161 (trans-2-pentene)

UNII |

* ALP8M0LU81 (1-pentene) Y
* 54UR3XZ4FC (cis-2-pentene) Y
* YCO1SJQ98H (trans-2-pentene) Y

InChI

* (1-pentene): InChI=1S/C5H10/c1-3-5-4-2/h3H,1,4-5H2,2H3

Key: YWAKXRMUMFPDSH-UHFFFAOYSA-N

* (cis-2-pentene): InChI=1S/C5H10/c1-3-5-4-2/h3,5H,4H2,1-2H3/b5-3-

Key: QMMOXUPEWRXHJS-HYXAFXHYSA-N

* (trans-2-pentene): InChI=1S/C5H10/c1-3-5-4-2/h3,5H,4H2,1-2H3/b5-3+

Key: QMMOXUPEWRXHJS-HWKANZROSA-N

SMILES

* (1-pentene): CCCC=C

* (cis-2-pentene): CC/C=C\C

* (trans-2-pentene): CC/C=C/C

Properties

Chemical formula

| C5H10
Molar mass | 70.135 g·mol−1
Density | 0.64 g/cm3 (1-pentene)[1]
Melting point |  −165.2 °C (−265.4 °F; 108.0 K) (1-pentene)[1]
Boiling point |  30 °C (86 °F; 303 K) (1-pentene)[1]

Magnetic susceptibility (χ)

| -53.7·10−6 cm3/mol
Hazards
Safety data sheet | MSDS

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Pentenes (also called Pentylenes) are alkenes with the chemical formula C5H10. Each molecule contains one double bond within its molecular structure. Six different compounds are in this class, differing from each other by whether the carbon atoms are attached linearly or in a branched structure and whether the double bond has a cis or trans form.

## Contents

* 1 Straight-chain isomers
* 2 Branched-chain isomers
* 3 Production of fuels
* 4 References

## Straight-chain isomers

1-Pentene is an alpha-olefin. Most often, 1-pentene is made as a byproduct of catalytic or thermal cracking of petroleum or during the production of ethylene and propylene via thermal cracking of hydrocarbon fractions.

The only commercial manufacturer of 1-pentene is Sasol Ltd., where it is separated from crude by the Fischer-Tropsch process.[2]

2-Pentene has two geometric isomers: cis-2-pentene and trans-2-pentene. Cis-2-Pentene is used in olefin metathesis.

## Branched-chain isomers

The branched isomers are 2-methylbut-1-ene, 3-methylbut-1-ene (isopentene), and 2-methylbut-2-ene (isoamylene).

Isoamylene is one of the three main byproducts of deep catalytic cracking (DCC), which is very similar to the operation of fluid catalytic cracking (FCC). The DCC uses vacuum gas oil (VGO) as a feedstock to produce primarily propylene, isobutylene, and isoamylene. The rise in demand for polypropylene has encouraged the growth of the DCC, which is operated very much like the FCC. Isobutylene and isoamylene feedstocks are necessary for the production of the much debated gasoline blending components methyl tert-butyl ether and tert-amyl methyl ether.

## Production of fuels

Propylene, isobutene, and amylenes are feedstocks in the alkylation units of refineries. Using isobutane, blendstocks are generated with high branching for good combustion characteristics. Amylenes are valued as precursors to fuels, especially aviation fuels of relatively low volatility, as required by various regulations.[3]

## References

1. ↑ 1.0 1.1 1.2 Record  in the GESTIS Substance Database of the Institute for Occupational Safety and Health
2. ↑ "RSA Olefins | cChange" (in en-US). http://www.cchange.ac.za/rsa-olefins/.
3. ↑ Bipin V. Vora; Joseph A. Kocal; Paul T. Barger; Robert J. Schmidt; James A. Johnson (2003). "Alkylation". Kirk‐Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0112112508011313.a01.pub2. ISBN 0-471-23896-1.

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Alkenes

Alkenes|

* Ethene ( C2H4 )
* Propene ( C3H6 )
* Butene ( C4H8 )
* Pentene ( C5H10 )
* Hexene ( C6H12 )
* Heptene ( C7H14 )
* Octene ( C8H16 )
* Nonene ( C9H18 )
* Decene ( C10H20 )

Preparations|

* Dehydrohalogenation from haloalkane
* Dehydration reaction from alcohol
* Semihydrogenation from alkyne
* Bamford–Stevens reaction
* Barton–Kellogg reaction
* Boord olefin synthesis
* Chugaev elimination
* Cope reaction
* Corey–Winter olefin synthesis
* Grieco elimination
* Hofmann elimination
* Horner–Wadsworth–Emmons reaction
* Hydrazone iodination
* Julia olefination
* Kauffmann olefination
* McMurry reaction
* Peterson olefination
* Ramberg–Bäcklund reaction
* Shapiro reaction
* Takai olefination
* Wittig reaction
* Olefin metathesis
* Ene reaction
* Cope rearrangement

Reactions|

* Hydrogenation
* Halogenation
* Hydration
* Electrophilic addition
* Oxymercuration reaction
* Hydroboration
* Cyclopropanation
* Epoxidation
* Dihydroxylation
* Ozonolysis
* Hydrohalogenation
* Polymerization
* Diels–Alder reaction
* Wacker process
* Dehydrogenation
* Ene reaction
* Friedel-Crafts Alkylation

* v
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Binary compounds of hydrogen

Alkali metal (Group 1) hydrides|

* LiH
* NaH
* KH
* RbH
* CsH

Lithium hydride, LiH
ionic metal hydride

Beryllium hydride
Left (gas phase): BeH2
covalent metal hydride
Right: (BeH2)n (solid phase)
polymeric metal hydride

Borane and diborane
Left: BH3 (special conditions), covalent metalloid hydride
Right: B2H6 (standard conditions), dimeric metalloid hydride

Methane, CH4
covalent nonmetal hydride

Ammonia, NH3
covalent nonmetal hydride

Water, H2O
covalent nonmetal hydride

Hydrogen fluoride, HF
covalent nonmetal hydride

Alkaline (Group 2) earth hydrides|

| Monohydrides|

* BeH
* MgH
* CaH
* SrH
* BaH

|

Dihydrides|

* BeH2
* MgH2
* CaH2
* SrH2
* BaH2

|

Group 13 hydrides|

| Boranes|

* BH3
* B2H6
* B2H2
* B2H4
* B4H10
* B5H9
* B5H11
* B6H10
* B6H12
* B10H14
* B18H22

|

Alanes|

* AlH3
* Al2H6

|

Gallanes|

* GaH3
* Ga2H6

|

Indiganes|

* InH3
* In2H6

|

Thallanes|

* TlH3
* Tl2H6

|

Group 14 hydrides|

| Linear alkanes|

* CH4
* C2H6
* C3H8
* C4H10
* C5H12
* C6H14
* C7H16
* C8H18
* C9H20
* C10H22
* more...

|

Linear alkenes|

* C2H4
* C3H6
* C4H8
* C5H10
* C6H12
* C7H14
* C8H16
* C9H18
* C10H20
* more...

|

Linear alkynes|

* C2H2
* C3H4
* C4H6
* C5H8
* C6H10
* C7H12
* C8H14
* C9H16
* C10H18
* more...

|

Silanes|

* SiH4
* Si2H6
* Si3H8
* Si4H10
* Si5H12
* Si6H14
* Si7H16
* Si8H18
* Si9H20
* Si10H22
* more...

|

Silenes|

* Si2H4

|

Silynes|

* Si2H2
* SiH

|

Germanes|

* GeH4
* Ge2H6
* Ge3H8
* Ge4H10
* Ge5H12

|

Stannanes|

* SnH4
* Sn2H6

|

Plumbanes|

* PbH4

|

* CH
* CH2
* CH3
* C2H
* Cycloalkanes
* Cycloalkenes
* Annulenes
* Many more

Pnictogen (Group 15) hydrides|

| Azanes|

* NH3
* N2H4
* N3H5
* N4H6
* N5H7
* N6H8
* N7H9
* N8H10
* N9H11
* N10H12
* more...

|

Azenes|

* N2H2
* N3H3
* N4H4

|

Phosphanes|

* PH3
* P2H4
* P3H5
* P4H6
* P5H7
* P6H8
* P7H9
* P8H10
* P9H11
* P10H12
* more...

|

Phosphenes|

* P2H2
* P3H3
* P4H4

|

Arsanes|

* AsH3
* As2H4

|

Stibanes|

* SbH3

|

Bismuthanes|

* BiH3

|

* HN3
* NH
* radical

Hydrogen chalcogenides (Group 16 hydrides)|

| Polyoxidanes|

* H2O
* H2O2
* H2O3
* H2O4
* H2O5
* H2O6
* H2O7
* H2O8
* H2O9
* H2O10
* more...

|

Polysulfanes|

* H2S
* H2S2
* H2S3
* H2S4
* H2S5
* H2S6
* H2S7
* H2S8
* H2S9
* H2S10
* more...

|

Selanes|

* H2Se
* H2Se2

|

Tellanes|

* H2Te
* H2Te2

|

Polanes|

* PoH2

|

* HO
* HO2
* HO3
* H2O+–O–
* H2S=S
* (HS)2S+–S–
* HS
* HDO
* D2O
* T2O

Hydrogen halides (Group 17 hydrides)|

* HF
* HCl
* HBr
* HI
* HAt

Transition metal hydrides|

* ScH2
* YH2
* YH3
* TiH2
* ZrH2
* HfH2
* VH
* VH2
* NbH
* NbH2
* TaH
* CrH
* CrH2
* CrHx
* NiH
* PdHx (x < 1)
* FeH
* FeH2
* FeH5
* CuH
* ZnH2
* CdH2
* HgH2

Lanthanide hydrides|

* LaH2
* LaH3
* LaH10
* CeH2
* CeH3
* PrH2
* PrH3
* NdH2
* NdH3
* SmH2
* SmH3
* EuH2
* GdH2
* GdH3
* TbH2
* TbH3
* DyH2
* DyH3
* HoH2
* HoH3
* ErH2
* ErH3
* TmH2
* TmH3
* YbH2
* YbH2.5
* LuH2
* LuH3

Actinide hydrides|

* AcH2
* ThH2
* Th4H15
* PaH3
* UH3
* NpH2
* NpH3
* PuH2
* PuH3
* AmH2
* AmH3
* CmH2

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