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F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
( R e d i r e c t e d f r o m 2 , 3 - b u t a n e d i o l )
2,3-Butanediol
Names
Preferred IUPAC name
Other names
2,3-Butylene glycol[citation needed & Bis-ethanol
Identifiers
CAS Number
19132-06-0 2 S S Y
24347-58-8 2 R R Y
5341-95-7 2 R S Y
3D model (JSmol )
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.431
EC Number
PubChem CID
UNII
7E9UXG71S1 2 S S Y
OR02B2286A 2 R R Y
F5IA8X9O8M 2 R S Y
CompTox Dashboard (EPA )
InChI=1S/C4H10O2/c1-3(5 )4(2 )6/h3-6H,1-2H3
Key: OWBTYPJTUOEWEK-UHFFFAOYSA-N
Properties
Chemical formula
C 4 H 10 O 2
Molar mass
−1
Appearance
Colorless liquid
Odor
odorless
Density
0.987 g/mL
Melting point
19 °C (66 °F; 292 K )
Boiling point
177 °C (351 °F; 450 K )
Solubility in water
Miscible
Solubility in other solvents
Soluble in alcohol , ketones , ether
log P
-0.92
Vapor pressure
0.23 hPa (20 °C)
Acidity (p K a 14.9
Refractive index (n D
1.4366
Thermochemistry
Heat capacity (C
213.0 J/K mol
Std enthalpy of (Δf H ⦵ 298 )
-544.8 kJ/mol
Hazards
NFPA 704
Flash point
85 °C (185 °F; 358 K )
Autoignition
402 °C (756 °F; 675 K )
Lethal dose or concentration (LD, LC):
LD 50 median dose )
5462 mg/kg (rat, oral)
Related compounds
Related butanediols
1,4-Butanediol 1,3-Butanediol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
2,3-Butanediol is the organic compound with the formula (CH 3 2 vic -diol (glycol ). It exists as three stereoisomers, a chiral pair and the meso isomer. All are colorless liquids. Applications include precursors to various plastics and pesticides.
Isomerism
[ edit ]
Of the three stereoisomers , two are enantiomers (levo- and dextro-2,3-butanediol) and one is a meso compound .[1] [2] 2 R R 2 S S 2 R S 2 S R
Industrial production and uses
[ edit ]
2,3-Butanediol is prepared by hydrolysis of 2,3-epoxybutane :[3]
(CH 3 CH )2 2 3 2 CH 3
The isomer distribution depends on the stereochemistry of the epoxide .
The meso isomer is used to combine with naphthalene-1,5-diisocyanate. The resulting polyurethane is called "Vulkollan".[3]
Biological production
[ edit ]
The (2 R R stereoisomer of 2,3-butanediol is produced by a variety of microorganisms in a process known as butanediol fermentation .[4] cocoa butter , in the roots of Ruta graveolens sweet corn , and in rotten mussels . It is used in the resolution of carbonyl compounds in gas chromatography .[5]
During World War II research was done towards producing 2,3-butanediol by fermentation in order to produce 1,3-butadiene , the monomer of the polybutadiene used in a leading type of synthetic rubber .[6] sugarcane molasses .[7]
Fermentative production of 2,3-butanediol from carbohydrates involves a network of biochemical reactions that can be manipulated to maximize production.[8]
2,3-butanediol has been proposed as a rocket fuel that could be created on Mars by means of cyanobacteria and E. coli [9]
2,3-Butanediol has been detected, in peppers, grape wine, anatidaes.
Reactions
[ edit ]
2,3-Butanediol undergo dehydration to form butanone (methyl ethyl ketone):[10]
(CH 3 2 3 O )CH2 CH 3 2 O
It can also undergo deoxydehydration to form butene :[11]
(CH 3 2 2 4 H 8 2 O
References
[ edit ]
^ Wang Y, Tao F, Xu P (2014). "Glycerol dehydrogenase plays a dual role in glycerol metabolism and 2,3-butanediol formation in Klebsiella pneumoniae " . Journal of Biological Chemistry 289 (9 ): 6080–6090. doi :10.1074/jbc.M113.525535 PMC 3937674 PMID 24429283 .
^ a b Heinz Gräfje, Wolfgang Körnig, Hans-Martin Weitz, Wolfgang Reiß, Guido Steffan, Herbert Diehl, Horst Bosche, Kurt Schneider and Heinz Kieczka "Butanediols, Butenediol, and Butynediol" in Ullmann's Encyclopedia of Industrial Chemistry , 2000, Wiley-VCH, Weinheim. doi :10.1002/14356007.a04_455
^ C. De Mas; N. B. Jansen; G. T. Tsao (1988). "Production of optically active 2,3-butanediol by Bacillus polymyxa". Biotechnol. Bioeng . 31 4 ): 366–377. doi :10.1002/bit.260310413 . PMID 18584617 . S2CID 36530193 .
^ "3,5-dinitrobenzoic acid". Combined Chemical Dictionary . Chapman and Hall /CRC Press . 2007.
^ "Fermentation Derived 2,3-Butanediol" , by Marcio Voloch et al. in Comprehensive Biotechnology , Pergamon Press Ltd., England Vol 2, Section 3, p. 933 (1986).
^ Dai, Jian-Ying; Zhao, Pan; Cheng, Xiao-Long; Xiu, Zhi-Long (2015). "Enhanced Production of 2,3-Butanediol from Sugarcane Molasses". Applied Biochemistry and Biotechnology . 175 (6 ): 3014–3024. doi :10.1007/s12010-015-1481-x . ISSN 0273-2289 . PMID 25586489 . S2CID 11287904 .
^ Jansen, Norman B.; Flickinger, Michael C.; Tsao, George T. (1984). "Application of bioenergetics to modelling the microbial conversion of D-xylose to 2,3-butanediol". Biotechnol Bioeng . 26 6 ): 573–582. doi :10.1002/bit.260260603 . PMID 18553372 . S2CID 22878894 .
^ "Rocket fuel made on Mars could propel astronauts back to Earth", Design Products & Applications , accessed 6 December 2021.
^ Nikitina, Maria A.; Ivanova, Irina I. (2016-02-23). "Conversion of 2,3-Butanediol over Phosphate Catalysts". ChemCatChem . 8 7 ): 1346–1353. doi :10.1002/cctc.201501399 . ISSN 1867-3880 . S2CID 102135312 .
^ Kwok, Kelvin Mingyao; Choong, Catherine Kai Shin; Ong, Daniel Sze Wei; Ng, Joy Chun Qi; Gwie, Chuandayani Gunawan; Chen, Luwei; Borgna, Armando (2017-06-07). "Hydrogen-Free Gas-Phase Deoxydehydration of 2,3-Butanediol to Butene on Silica-Supported Vanadium Catalysts". ChemCatChem . 9 13 ): 2443–2447. doi :10.1002/cctc.201700301 . ISSN 1867-3880 . S2CID 99415384 .
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=2,3-Butanediol&oldid=1233991714 " C a t e g o r i e s : ● A l k a n e d i o l s ● V i c i n a l d i o l s ● B u t a n e H i d d e n c a t e g o r i e s : ● A l l a r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s ● A r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s f r o m J u l y 2 0 1 8 ● C h e m i c a l a r t i c l e s w i t h m u l t i p l e c o m p o u n d I D s ● M u l t i p l e c h e m i c a l s i n a n i n f o b o x t h a t n e e d i n d e x i n g ● C h e m i c a l a r t i c l e s w i t h m u l t i p l e C A S r e g i s t r y n u m b e r s ● A r t i c l e s w i t h o u t K E G G s o u r c e ● A r t i c l e s w i t h c h a n g e d E B I i d e n t i f i e r ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 1 2 J u l y 2 0 2 4 , a t 0 0 : 4 3 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
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