Share to: share facebook share twitter share wa share telegram print page

Isobutylene

Isobutylene
Skeletal formula of isobutylene
Skeletal formula of isobutylene
Ball-and-stick model of isobutylene
Ball-and-stick model of isobutylene
Space-filling model of isobutylene
Space-filling model of isobutylene
Names
Preferred IUPAC name
2-Methylprop-1-ene
Other names
2-Methylpropene
Isobutene
γ-Butylene
2-Methylpropylene
Methylpropene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.697 Edit this at Wikidata
EC Number
  • 204-066-3
RTECS number
  • UD0890000
UNII
UN number 1055
In Liquefied petroleum gas: 1075
  • InChI=1S/C4H8/c1-4(2)3/h1H2,2-3H3 checkY
    Key: VQTUBCCKSQIDNK-UHFFFAOYSA-N checkY
  • InChI=1/C4H8/c1-4(2)3/h1H2,2-3H3
  • CC(=C)C
Properties[1]
C4H8
Molar mass 56.106 g/mol
Appearance Colorless gas
Density 0.5879 g/cm3, liquid
Melting point −140.3 °C (−220.5 °F; 132.8 K)
Boiling point −6.9 °C (19.6 °F; 266.2 K)
-44.4·10−6 cm3/mol
Hazards[2]
GHS labelling:
Flam. Gas 1Press. Gas
Danger
H220
P210, P377, P381, P403
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
4
0
Flash point flammable gas
465 °C (869 °F; 738 K)
Explosive limits 1.8–9.6%
Related compounds
Related butenes
1-Butene
cis-2-Butene
trans-2-Butene
Related compounds
Isobutane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula (CH3)2C=CH2. It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value.[3]

Production

Polymer and chemical grade isobutylene is typically obtained by dehydrating tertiary butyl alcohol (TBA) or catalytic dehydrogenation of isobutane (Catofin or similar processes).[4] Gasoline additives methyl tert-butyl ether (MTBE) and ethyl tert-butyl ether (ETBE), respectively, are produced by reacting methanol or ethanol with isobutylene contained in butene streams from olefin steam crackers or refineries, or with isobutylene from dehydrated TBA. Isobutylene is not isolated from the olefin or refinery butene stream before the reaction, as separating the ethers from the remaining butenes is simpler. Isobutylene can also be produced in high purities by "back-cracking" MTBE or ETBE at high temperatures and then separating the isobutylene by distillation from methanol.

Isobutylene is a byproduct in the ethenolysis of diisobutene to prepare neohexene:[5]

(CH3)3C-CH=C(CH3)2 + CH2=CH2 → (CH3)3C-CH=CH2 + (CH3)2C=CH2

Uses

Isobutylene is used in the production of a variety of products. It is alkylated with butane to produce isooctane or dimerized to diisobutylene (DIB) and then hydrogenated to make isooctane, a fuel additive. Isobutylene is also used in the production of methacrolein. Polymerization of isobutylene produces butyl rubber (polyisobutylene or PIB). Antioxidants such as butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA) are produced by Friedel-Crafts alkylation of phenols with isobutylene.

tert-Butylamine is produced commercially by amination of isobutylene using zeolite catalysts:[6]

NH3 + CH2=C(CH3)2 → H2NC(CH3)3

Applications are found in the calibration of photoionization detectors.

Safety

Isobutylene is a highly flammable gas.

See also

References

  1. ^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.). Merck. 1989. ISBN 091191028X., 5024.
  2. ^ Isobutene, International Chemical Safety Card 1027, Geneva: International Programme on Chemical Safety, April 2000
  3. ^ Geilen, Frank M.A.; Stochniol, Guido; Peitz, Stephan; Schulte-Koerne, Ekkehard (2014). "Butenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_483.pub3. ISBN 978-3527306732.
  4. ^ Olah, George A.; Molnár, Árpád (May 2003), Hydrocarbon Chemistry, Wiley-Interscience, ISBN 978-0-471-41782-8.
  5. ^ Lionel Delaude; Alfred F. Noels. "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Wiley.
  6. ^ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 3527306730.
Index: pl ar de en es fr it arz nl ja pt ceb sv uk vi war zh ru af ast az bg zh-min-nan bn be ca cs cy da et el eo eu fa gl ko hi hr id he ka la lv lt hu mk ms min no nn ce uz kk ro simple sk sl sr sh fi ta tt th tg azb tr ur zh-yue hy my ace als am an hyw ban bjn map-bms ba be-tarask bcl bpy bar bs br cv nv eml hif fo fy ga gd gu hak ha hsb io ig ilo ia ie os is jv kn ht ku ckb ky mrj lb lij li lmo mai mg ml zh-classical mr xmf mzn cdo mn nap new ne frr oc mhr or as pa pnb ps pms nds crh qu sa sah sco sq scn si sd szl su sw tl shn te bug vec vo wa wuu yi yo diq bat-smg zu lad kbd ang smn ab roa-rup frp arc gn av ay bh bi bo bxr cbk-zam co za dag ary se pdc dv dsb myv ext fur gv gag inh ki glk gan guw xal haw rw kbp pam csb kw km kv koi kg gom ks gcr lo lbe ltg lez nia ln jbo lg mt mi tw mwl mdf mnw nqo fj nah na nds-nl nrm nov om pi pag pap pfl pcd krc kaa ksh rm rue sm sat sc trv stq nso sn cu so srn kab roa-tara tet tpi to chr tum tk tyv udm ug vep fiu-vro vls wo xh zea ty ak bm ch ny ee ff got iu ik kl mad cr pih ami pwn pnt dz rmy rn sg st tn ss ti din chy ts kcg ve 
Prefix: a b c d e f g h i j k l m n o p q r s t u v w x y z 0 1 2 3 4 5 6 7 8 9 
Kembali kehalaman sebelumnya