Article No : a04_475

2-Butanone
DETLEF HOELL, Sasol Solvents Germany GmbH, Moers, Germany
THOMAS MENSING, Sasol Solvents Germany GmbH, Moers, Germany
RAFAEL ROGGENBUCK, Sasol Solvents Germany GmbH, Moers, Germany
MICHAEL SAKUTH, Sasol Solvents Germany GmbH, Moers, Germany
EGBERT SPERLICH, Sasol Solvents Germany GmbH, Moers, Germany
THOMAS URBAN, Sasol Solvents Germany GmbH, Moers, Germany
WILHELM NEIER, Deutsche Texaco AG, Moers, Germany
GUENTER STREHLKE, Deutsche Texaco AG, Moers, Germany

1. Introduction. . . . . . . . . . . . . . . . . . . . . . 431 8.1. Occupational Exposure . . . . . . . . . .... 439

2. Physical Properties . . . . . . . . . . . . . . . . 432 8.2. Toxicokinetics and Metabolism . . . .... 440
3. Chemical Properties . . . . . . . . . . . . . . . 432 8.2.1. Absorption . . . . . . . . . . . . . . . . . . . .... 440
4. Production . . . . . . . . . . . . . . . . . . . . . . . 434 8.2.1.1. Oral Exposure . . . . . . . . . . . . . . . . . .... 440
4.1. Catalytic Dehydrogenation of sec-Butyl 8.2.1.2. Inhalation Exposure. . . . . . . . . . . . . .... 440
Alcohol (SBA) in the Gaseous Phase . . . . . 434 8.2.1.3. Dermal Exposure. . . . . . . . . . . . . . . .... 440
4.2. MEK as a Byproduct of the Fischer- 8.2.2. Distribution . . . . . . . . . . . . . . . . . . . .... 440
Tropsch Coal-to-Liquid Process. . . . . . . 436 8.2.3. Metabolism . . . . . . . . . . . . . . . . . . . .... 440
4.3. Liquid-Phase Oxidation of n-Butane . . . 436 8.2.4. Elimination and Excretion . . . . . . . . .... 440
4.4. Oxidation of sec-Butylbenzene According 8.2.5. Mechanism of Action . . . . . . . . . . . .... 441
to the Hock Phenol Synthesis. . . . . . . . . 437 8.2.6. Toxic Effects. . . . . . . . . . . . . . . . . . .... 441
4.5. Direct Oxidation of n-Butenes (Hoechst- 8.2.6.1. Oral Exposure . . . . . . . . . . . . . . . . . .... 441
Wacker Process) . . . . . . . . . . . . . . . . . . 437 8.2.6.2. Inhalation Exposure. . . . . . . . . . . . . .... 441
5. Quality, Storage, Transportation . . . . . . 438 8.2.6.3. Occupational Health . . . . . . . . . . . . .... 442
6. Uses . . . . . . . . . . . . . . . . . . . . . . . . . . . . 439 8.2.6.4. Regulations . . . . . . . . . . . . . . . . . . . .... 442
7. Economic Aspects . . . . . . . . . . . . . . . . . 439 References . . . . . . . . . . . . . . . . . . . .... 442
8. Toxicology and Occupational Health . . . 439

1. Introduction Maruzen (JP), Oxiteno (BR), Petro Brazi (RO),

2-Butanone [78-93-3], methyl ethyl ketone,
MEK, is the second link in the homologous series
of aliphatic ketones and, next to acetone, the most
important commercially produced ketone. 2-Bu-
tanone is produced primarily by dehydrogenation
of 2-butanol, analogous to the production of
acetone by dehydrogenation of gaseous isopro-
pyl alcohol on copper, zinc, or bronze catalysts at
400 550
C. At 80 95 % 2-butanol conver-
sion, MEK selectivity is > 95 %. Butenes (dehy-
dration) and higher ketones (auto condensation)
are byproducts. In 2005, about 1  106 t of MEK
were produced worldwide.
2-Butanone is produced by Arkema (F), Ce-
lanese (US), Exxon (GB, US), Idemitsu (JP),
Sasol (RSA, Germany), Shell (NL), SK Corp
Ulsan (KOR), Tasco Chemical (Taiwan); Tonen
(JP) [8]. Interest in MEK as a solvent for paints
and adhesives has been growing since the 1980s.
In general, MEK is considered to be in competi-
tion to ethyl acetate, especially as a low-boiling
solvent. It has broad application as a solvent for
nitrocellulose, cellulose acetate butyrate, ethyl
cellulose, acrylic resins, vinyl acetates, and vinyl
chloride vinyl acetate copolymer (based on
synthetic surface-coating preparation). It is fa-
vored as a lacquer solvent because of its low
viscosity, high solids concentration, and wide
diluents tolerance.
The withdrawal of MEK from the HAP
(hazardous air pollutant) list in 2005 was impor-

2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

DOI: 10.1002/14356007.a04_475.pub2
432 2-Butanone Vol. 6

tant to maintain the market position for MEK in Table 2. Binary azeotropic mixtures of MEK [12]
the US. bp of bp of MEK content
Moreover, MEK can be used as an activator component, azeotrope, of azeotrope,



for oxidative reactions, as a selective extractive Component C C wt %
agent, as a special solvent for dewaxing mineral Water 100.0 73.4 88.7
oil fractions, and as a chemical intermediate. Benzene 80.2 78.4 44.3
n-Hexane 68.9 64.3 29.5
n-Heptane 98.4 77.0 71.3
Cyclohexane 80.8 71.8 44.1
2. Physical Properties Methanol 64.7 63.9 32.8
Ethanol 78.3 74.0 60.9
MEK is a colorless, low-viscosity, flammable Isopropyl alcohol 82.4 77.5 70.4
liquid with a characteristic ketone-like odor sim- tert-Butyl alcohol 82.5 78.7 69.0

ilar to that of acetone. With a bp of 79.6
C and

Ethyl acetate 77.1 77.0 18.0
Methyl propionate 79.8 79.0 60.0
an Mr of 72.1 it is classified as a low-boiling, fast Di-isopropyl ether 68.3 66.8 16.2
evaporating solvent. MEK is only partially mis- Di-n-propyl ether 90.1 78.3 74.6
cible with water, whereas it is completely misci-
ble with most organic solvents. Physical proper-
ties of MEK are provided in Table 1. MEK does not form a binary azeotropie with
MEK forms binary and ternary azeotropic toluene, m-xylene, n-butanol, isobutanol, 2-
mixtures in combination with water and several butanol, 4-methyl-2-pentanol, allyl alcohol,
organic compounds. Examples of binary and methyl acetate, isopropyl acetate, n-butyl ace-
ternary azeotropes are given in Table 2 and 3. tate, isobutyl acetate, formic acid, and acetic
acid.
Table 1. Physical Properties of MEK [911]

Property Value 3. Chemical Properties

Mr 72.107
mp,
C 86.7 Under normal conditions and in the absence of
bp,
C 79.6
Liquid density at 25
C, g/cm3 0.7995
atmospheric oxygen, MEK is stable. Care must
Critical temperature,
C 262.45 be taken after prolonged storage because perox-
Critical pressure, MPa 4.15 ides may form in the presence of oxygen [14, 15].
Critical density, r, g/cm3 0.270
Vapor pressure at 25
C, kPa 12.71 Table 3. Ternary azeotropic mixtures of MEK [13]
Refractive index at 25
C, n25
D 1.3764
Liquid viscosity at 25
C, mPa  s 0.395 bp of bp of Composition
Liquid heat capacity at 25 C, J g1 K1


2.200
component, azeotrope, of azeotrope,
Heat of vaporization at 79.6
C, kJ/mol 31.55


Component C C wt %
Heat of fusion, J/mol 7456
Surface tension at 20
C, mN/m 24.6 MEK 79.6 17.5
Thermal conductivity, W m1 K1 Benzene 80.2 68.9 73.6
at 0
C 0.150 Water 100.0 8.9
20
C 0.145 MEK 79.6 27.1
50
C 0.137 n-Hexane 68.9 56 68.1
Solubility at 20
C Water 100.0 4.8
MEK in water, wt % 27.5 MEK 79.6 35
water in MEK, wt % 12.5 Cyclohexane 80.8 63.6 60
Flash point (DIN 51755),
C 1 Water 100.0 5
Flash point closed cup,
C 6,1 MEK 79.6 75
Flammability limits in air Ethanol 78.3 73.2 14
lower, vol % 1.8 Water 100.0 11
upper, vol % 11.5 MEK 79.6 88
Ignition temperature,
C 505 Isopropyl alcohol 82.4 73.4 1
Electric conductivity at 20
C, W1 cm1 5  108 Water 100.0 11
Dipole moment, Debye 3.18 MEK 79.6 16.7
Dielectric constant of the liquid at 20
C 15.45 Isopropyl alcohol 82.4 68.9 23.3
Evaporation number (ether1) 2.6 Cyclohexane 80.8 60.0
Vol. 6
Explosions may occur because of instantaneous
decomposition of peroxides.
2-Butanone is unsaponifiable and heat- and
light-resistant. It decomposes only after pro-
longed UV exposure (yielding ethane, methane,
carbon monoxide, ethylene, and diacetyl) [16].
Diacetyl [431-03-8] is formed by oxidation
with air in the presence of special catalysts [17].
Methyl ethyl ketone peroxide [19393-67-0], a
polymerization catalyst, is formed by oxidation
with a 30 % solution of hydrogen peroxide [18].
Nitric acid and other strong oxidants oxidize
MEK to a mixture of formic and propionic
acids [18].
2-Butanol [78-92-2] is obtained by catalytic
reduction with hydrogen [18]. It can also be
formed by electrolytic reduction in sodium ace-
tate solution or by reduction with ammonium
amalgam or lithium aluminum hydride. 3,4-Di-
methyl-3,4-hexanediol is obtained by electrolyt-
ic reduction in an acidic medium or by reduction
with magnesium amalgam [18].
Methyl ethyl ketone forms addition products
with hydrogen cyanide as well as with sodium
and potassium hydrogen sulfites. In an alkaline
medium, MEK condenses with aldehydes to
form higher unsaturated ketones. Condensation
with formaldehyde to form methyl isopropenyl
ketone [563-80-4], an intermediate for further
syntheses, is of particular interest. During base-
catalyzed autocondensation in the liquid
phase and during gase-phase condensation on
alkalinized copper catalysts, the carbonyl group
reacts with the methyl group, whereas during
acid-catalyzed condensation the methylene
group in a-position to the carbonyl group is
attacked [19].
Methyl ethyl ketone and citral [5392-40-5]
condense to form methylpseudoionone that can
be cyclized to methylionone, a compound used
for producing synthetic violet perfume.
During condensation with low-molecular al-
dehydes (during base-catalyzed and acid-cata-
2-Butanone 433
lyzed aldolization) the a-position of the carbonyl
group is first occupied [20, 21].
Thus, the base-catalyzed aldolization with
less than stoichiometric amounts of formalde-
hyde yields 2-methyl butane-1-ol-3-one [20] and
exhaustive hydroxymethylation, with reduction
of the carbonyl group (crossed Cannizzaro reac-
tion), produces desoxyanhydroeneaheptite [22].
When MEK is reacted with primary and sec-
ondary alcohols, higher ketones are obtained.
Reaction with sec-butyl alcohol gives ethyl amyl
ketone [106-68-3] [23].
Methyl ethyl ketone reacts with polyoxy com-
pounds or epoxides to form cyclic products.
Amyl nitrite [110-46-3] attacks the CH2 group
in a-position to the carbonyl group and yields the
monooxime of diacetyl.
The keto group reacts with amino groups
with elimination of water. In combination with
hydroxylamine [7803-49-8], methyl ethyl ketox-
ime, an antiskinning agent, is formed.
Condensation of MEK with aliphatic esters
and anhydrides gives b-diketones.
Phenols react with MEK to form oxypheny-
lene compounds. In combination with phenol,
2,2-hydroxyphenyl butane is obtained, a homo-
log of hydroxyphenyl propane (Bisphenol A [80-
05-7]), an important material for the production
of synthetic resins.
Methyl ethyl ketone can be halogenated in the
a-position. Methyl ethyl ketone reacts with
Grignard compounds to form tertiary alcohols.
With acetylene in the presence of sodium am-
ide 3-methyl-1-pentyn-3-ol [77-75-8] is formed.
N-Methyl-formyl-aminobutane is obtained from
434 2-Butanone
MEK plus N-methylformamide. The Reformatz-
ky reaction produces the b-oxyester from
monobromine-substituted esters [23].
4. Production
Today MEK is mainly produced by dehydroge-
nation of 2-butanol (sec-butyl alcohol, SBA),
i.e., approximately 92% of all production capaci-
ties worldwide use this process technique (2006).
SBA itself can easily be produced by hydra-
tion of n-butenes (from petrochemically pro-
duced C4-raffinates) in a two-step process (cata-
lyst used is liquid sulfuric acid), or in a single-
step process by direct addition of water on a
stabilized acidic ion exchange resin, which is
used as a catalyst [24].
The remaining 8% of MEK is produced by
fatal production via FischerTropsch [25] or by a
process, in which liquid n-butane is oxidized
catalytically to produce acetic acid and MEK as
byproduct [26].
Following a closure of its MEK production
plant in the U.S., Shell Chemicals announced in
2005 [27] the building of a 300400  103 t/a
world-scale plant for phenol production using the
Shells phenol acetone MEK (SPAM) technolo-
gy. SPAM technology uses benzene, propene,
and n-butenes as feedstock components to pro-
duce phenol and MEK with acetone as byproduct
via the traditional process pathways, i.e., the
intermediates cumene and sec-butylbenzene are
oxidized according to Hocks phenol synthesis
route, which gives phenol and the named ketones
after acid-catalyzed splitting.
A 300400  103 t/a SPAM phenol plant,
which is planned in the Far East by Shell Che-
micals, would co-produce 130140  103 t/a
MEK.
The first attempts using this production route
were not economically viable because of long
reaction times combined with low product yields
[28]. After some improvements, i.e., mixing of
cumene with sec-butylbenzene, the reaction
times could be reduced to a major extent, which
led to a higher product selectivity [29].
The auto-oxidation of liquid sec-butyl alco-
hol, which gives MEK and hydrogen peroxide
[30], and the catalytic oxidative hydration of
gaseous n-butenes [31] are no longer economical
process pathways. In this context, it should be
Vol. 6
mentioned that the oxidative dehydrogenation of
sec-butyl alcohol to produce MEK plus stochio-
metric amounts of water is also discussed in the
literature [32].
The direct oxidation of n-butenes (Hoechst-
Wacker process, Maruzen process, [33, 34]) has
not been generally accepted, because of unde-
sired byproduct formation.
The oxidation of n-butenes with ethylbenzene
hydroperoxide to form butylene oxides and sub-
sequent hydration and formation of ketones
seems not to be attractive anymore because of
its technical difficulties in operational realiza-
tion. Styrene, n-butanol, and MEK are obtained
as coupled products [35].
4.1. Catalytic Dehydrogenation of
sec-Butyl Alcohol (SBA) in the Gaseous
Phase
The catalytic dehydrogenation of sec-butyl alco-
hol (SBA) is an endothermic reaction (DHR
51 kJ/mol). The equilibrium constant Kp for
SBA to MEK can be calculated by the following
equation [36]:
log KP 2:790  T 1 1:51 log T1:865
T reaction temperature
The MEK concentration in the reaction mixture
increases with temperature and levels out at
approx. 350
C (assuming that no consecutive
reactions follow) [37].
Copper [38], zinc [39], or bronze [40] are
typical catalysts for the gas-phase dehydroge-
nation. Compared to copper as catalyst, zinc or
bronze usually require higher dehydrogenation
temperatures (400
C). Usually, zinc oxide
shows a lower selectivity because of a dehy-
dration side-reaction of SBA to n-butenes.
Platinum on alumina [41], copper or chromium
[42, 43] as well as copper, and zinc on alumina
[41] are recommended as dehydrogenation cat-
alysts for SBA, which contains significant
amount of water. Commercially used catalysts
are reactivated by oxidation with air after 36
months of usage. Reactivation is necessary if
the alcohol conversion rate is reduced over
time-on-stream by contamination of the cata-
lytical active sides with water, deposits of
butene oligomers and di-sec-butyl-ether [44],
Vol. 6
which are removed by use of higher tempera-
tures and oxidation.
Typically, the commercial catalysts show a
total lifetime of more than several years.
Deutsche Texaco developed a process tech-
nology for MEK production based on dehydro-
genation of anhydrous sec-butyl alcohol on a
copper-based precipitation catalyst at 240
260
C under normal pressure [24, 38]. By using
this technology, sec-butyl alcohol is produced
via direct hydration of n-butenes, catalyzed by a
temperature-stabilized acidic ion-exchange res-
in [45]. Beyond this improved heterogeneous
procedure, worldwide SBA is still mainly pro-
duced by use of concentrated sulfuric acid as a
catalyst via an indirect route. The resulting in-
termediate mono- or di-sec-butylsulfate of the
first reaction step is hydrolyzed in a second
reaction step.
The gas hourly space velocity (GHSV) of
Deutsche Texacos dehydrogenation technology
is roughly 1 Nm3 per liter catalyst and hour. At a
relatively high selectivity far above 90 %, a
conversion of approximately 90 % can be
achieved. Every 34 month time-on-stream,
the catalyst has to be reactivated with air at
higher temperatures to get back the initial rate
of reaction. These operational facts make this
process technology still economically highly
attractive.
Liquid sec-butyl alcohol is vaporized in an
evaporator. The gaseous alcohol stream is sent to
a multitube reactor, where the dehydrogenation
Figure 1. Gas-phase dehydrogenation of sec-butyl alcohol (Deutsche Texaco AG process) a) Multitube reactor; b) Evaporator;
c) Condenser; d) Separator; e) Refrigerator; f) Distillation column system
2-Butanone 435
occurs on a copper catalyst. The endothermic
reaction heat of 51 kJ/mol is supplied by a heat
transfer oil system. The gaseous product stream
leaves the reactor and, after cooling to ambient
temperature, it is split into a liquid crude MEK
phase and a gaseous hydrogen phase. The hydro-
gen is further purified by deep temperature cool-
ing in a refrigerator system (Fig. 1).
The liquid stream still contains, beyond the
desired MEK, some unconverted SBA, 5-meth-
yl-3-heptanone, higher ketones, and water. 5-
Methyl-3-heptanone, higher ketones and water
are the only byproducts which are formed via an
autocondensation of two or more MEK mole-
cules. In this case, the extent of autocondensation
is still much lower compared to that of the
acetone process. Dehydration of SBA, which
results in n-butene formation, is practically not
detectable.
The MEK is purified in three consecutive
distillation steps, which operate under
normal atmospheric pressure. In the first step,
an azeotropic MEKwater stream is taken as
overhead stream, which is purified batchwise
in a separate distillation column. The second
column gives the desired pure MEK (with a
typical purity over 99 %) and SBA mixed with
the higher ketones as a bottom stream. In the last
distillation step, the unconverted SBA is distilled
off (overhead stream) and is sent back to the
process feed tank. The bottom products are the
higher ketones formed as byproducts during
synthesis.
436 2-Butanone Vol. 6

Reference
Table 4 summarizes all currently known pro-
cess technologies for the MEK production

[46]
[47]
[40]
[48]
[49]
[42]

[43]

[44]
[44]
by gas-phase dehydrogenation of sec-butyl
alcohol.

Yield, mol %

93 94

73 77
97.8c
4.2. MEK as a Byproduct of the

79.2
80

90

90
Fischer-Tropsch Coal-to-Liquid
Process

Selectivity,

93 96

86 92
mol %
In the Fischer-Tropsch process, carbon monox-

96.3
100
100

63b
97
99
ide and hydrogen the synthesis gas are cat-
alytically converted into liquid hydrocarbons
with a large spectrum of different chain

Conversion, %

92.5 93.5
lengths and a remarkable amount of several

96 97

88 93

81 85
byproducts.

57.3a
Developed in the 1920s by the German re-

80

96
90
searchers FRANZ FISCHER and HANS TROPSCH, this
process is commercially used and improved by
Pressure, MPa
South Africans SASOL Ltd. since 1955 to pro-

0.1 0.3
duce synthetic fuels from coal.
In a two-step process technique, mineral coal
0.3

0.6
0.6
is gasified to produce synthesis gas, which is
thereafter extensively purified by absorption in
Temperature,
C

scrubber systems (using the Rectisol technolo-

gy). The purified synthesis gas is catalytically
270 320

converted into hydrocarbons (! Coal

Table 4. Process technologies for MEK production by gas-phase dehydrogenation of 2-butanol

Liquefaction).
400
413
390

300
260

180

358
286
Besides the main products, i.e., olefins, syn-
thetic fuel, and waxes, a large variety of water-
H2O content,

soluble oxygenates are achieved as byproducts

with a selectivity of 3 - 6 % in the reaction water
vol %

stream [25].
90.4
0
0
0
0

0
0

Via traditional separation technologies, these

oxygenates (alcohols, organic acids, aldehydes,
22 % Cu, 8 % BaCrO4, 2 % Cr2O3,

MEK, and other ketones) are purified to high-

value solvent products.
60 % Cu, Cr2O3, MgO, 12 %

0.5 % Na2O, 61 % SiO2

5 % Cu, 5 % Cr/Al2O3
ZnO/Na2CO3/Al2O3

4.3. Liquid-Phase Oxidation

0.05 % Pt/Al2O3
SiO2, 10 % H2O
CuO/NaF/SiO2

of n-Butane
ZnO/Bi2O3

CuO/CrO
Catalyst

bronze

2-Butanone is a byproduct in the liquid-phase

Relative to di-sec -butyl ether.
Relative to sec-butyl alcohol.

oxidation of n-butane to acetic acid. Auto-oxi-

dation or direct oxidation of n-butane takes place
Esso Research & Eng.

in the liquid phase via a radical reaction pathway

Knapsack Griesheim

to give MEK as an intermediate product, which,

upon further oxidation, forms MEK hydroperox-
Veba-Chemie

Shell-Chemie
Shell-Chemie

Total yield.
Standard Oil

Maruzen Oil

Toyo Rayon
Ruhrchemie

ide that is subsequently cleaved into two mole-

Company

cules to give the desired acetic acid as the end

product.
a
b
c
Vol. 6
The continuous plug-flow process developed
by Union Carbide Corp. allows the partial col-
lection of MEK intermediate [50]. MEK and
acetic acid (mass ratio 0.15/1.00.23/1.0) are
obtained by noncatalyzed liquid-phase oxida-
tion at 180
C and 5.3 MPa with some back-
mixing.
Continuous oxidation under plug-flow condi-
tions at 150
C, 6.5 MPa, and a residence time of
2.7 min forms MEK and acetic acid at mass
ratios of up to 3/1 [50].
Celanese Corp. uses acetic acid as a solvent
with cobalt acetate and sodium acetate as a
homogeneously dissolved oxidation catalyst
system [51]. It is a batch process performed
between 160 and 165
C at 5.7 MPa. MEK
and acetic acid are obtained in a mass ratio of
0.4/1.0.
The Celanese plant using this technology still
runs in the USA (Pampa, Texas).
4.4. Oxidation of sec-Butylbenzene
According to the Hock Phenol
Synthesis
Shells combined phenolacetoneMEK tech-
nology (SPAM technology) is based on oxidizing
a mixture of sec-butylbenzene and cumene to the
respective hydroperoxide molecules, which
thereafter are cleaved traditionally with an inor-
ganic acid (preferable sulfuric acid) to give the
desired products, i.e., a mixture of phenol plus
MEK and acetone. The crude ketone stream is
separated by distillation from the phenol and is
further purified to the desired pure ketone
components.
The catalytic cleavage of sec-butylbenzene
hydroperoxide (sBHP) with an inorganic acid to
produce phenol plus MEK has been well-known
for many years. It is described and patented
in [52].
Although MEK compared to acetone is the
industrially more important ketone, this alterna-
tive route has not been commercialized because
of a major problem which occurs in the oxidation
step. The rate of reaction for the autocatalytic
oxidation of sec-butylbenzene is several times
slower than that of cumene. Therefore, side
reactions have a negative impact on the overall
yield of the desired products.
2-Butanone 437
The first attempt to overcome the negative
effect was described in 1987 according to [53].
By adding cumene hydroperoxide (CHP) as an
initiator to sec-butylbenzene, the oxidation reac-
tion rate could be increased to some extent, so
that the negative impact of the byproduct forma-
tion is reduced. Later, it was patented by Phe-
nolchemie [54] to add only cumene in minor
percentages (i.e., between 5 and 15 wt %), which
allows the formation of acetophenone as the main
byproduct.
According to Shells investigations, the de-
crease in reaction rate in the oxidation of sec-
butylbenzene is caused by the formation of
cleaved products as radical scavenger in the
reaction mixture in the ppm range, i.e., the
formation of formic acid, acetic acid, and
phenol. To overcome this negative effect on the
rate of reaction, the following options are sug-
gested [29]:
. Using a mixture of sec-butylbenzene and cu-
mene to build up some initial amounts of CHP
in the first reaction step, which acts as an
initiator
. Reducing the amounts of methanol or ethanol
created as cleaved products in recycle streams,
which lowers the formation of the above-men-
tioned scavenger acids
. Adding an aqueous solution of ammonia to
such extent that the acids can form their am-
monium salts, whereas phase splitting has to be
avoided.
A schematic diagram of the reaction and
purification steps according to [29] is depicted
in Figure 2.
4.5. Direct Oxidation of n-Butenes
(Hoechst-Wacker Process)
In the direct oxidation of n-butenes according to
the Hoechst-Wacker process, oxygen is trans-
ferred in a homogeneous phase onto n-butenes
using a redox salt pair, PdCl2/2 CuCl [55, 56].
The salt pair is subsequently re-oxidized.
438 2-Butanone Vol. 6

Table 5. ASTM specifications for MEK [65]

Specification
Type I Type II method

Commercial regular urethane

reference grade
Acidity, wt % max. 0.005 max. 0.003 D 1613
Alcohol, wt % max. 0.5 D 2804
Color, Pt-Co scale max. 10 max. 10 D 1209
Distillation range D 1078
(760 mm Hg)
Initial boiling min. 78.5 min. 78.5
point,
C
Dry point,
C max. 81.0 max. 81.0
Nonvolatile matter, max. 5 max. 5 D 1353
mg/100 mL
Purity, wt % min. 99.5 min. 99.5 D 2804
Apparent specific D 268 or
gravity D 4052
20/20
C or 0.8050.807 0.8050.807
25/25
C 0.8010.803 0.8010.803
Water, wt % max. 0.2 max. 0.05 D 1364

Figure 2. Process for co-producing phenol and methyl ethyl

ketone (Shell Chemicals, according to [29]) A long permanganate time according to
ASTM D 1363 indicates high purity.
Storage life of MEK is limited because of
n-Butenes can be converted into the following discoloration. Since MEK is somewhat hygro-
reaction products (conversions of up to 95% are scopic, water is absorbed from the air.
attained): Carbon steel, stainless steel (CrNi and CrNiMo),
and aluminum containers are suitable for storage
and transportation [66, 67]. Carbon steel or contain-
ers with zinc silicate lining are recommended for
Reaction products: Selectivities, mol %
MEK 86 long-term storage. Only a few plastics such as poly
n-Butanal 4 (tetrafluoroethylene) (PTFE), ethylenepropene
Chlorinated products 6 diene terpolymer (EPDM), ethylenechlorotri-
Carbon dioxide 1 fluoroethylene (ECFTFE), perfluoroalkoxy (PFA)
polymers, butyl rubber, or polyamide are compati-
The main disadvantages are: formation of ble for gasket materials [67].
chlorinated butanones and n-butanal and corro- The following regulations for transportation of
sion caused by free acids. MEK must be observed. Classification and defi-
The Maruzen process is similar [57, 58]. nitions of classes of dangerous goods see [68].
Oxygen is transferred by an aqueous solution of
palladium sulfate and ferric sulfate. Other pro- Land transport ADR/RID
cesses employing the same oxygen transfer prin- UN number 1193
ciple were developed by Consortium f ur Elek- Class 3
Packaging group II
trochemie [59] and Eastman Kodak [60]. For Inland waterways transport ADNR
further processes, see [6164]. UN number 1193
Class 3
Packaging group II
Marine transport IMDG
5. Quality, Storage, Transportation UN number 1193
Class 3.2
MEK is industrially produced in high quality Packaging group II
Air transport ICAO/IATA
according to ASTM D 740, DIN 53247 and BS UN number 1193
1940. Class 3
ASTM standard specifications for MEK are Packaging group II
given in Table 5. USA 49 CFR 172.101
Vol. 6
6. Uses
MEK is an important solvent with properties
similar to those of acetone. MEK has the follow-
ing advantages in comparison to other solvents
with comparable rates of evaporation: very high
power of dissolution, high ratio of dissolved
matter/viscosity, miscibility with a large number
of hydrocarbons without impairing the solids
content or viscosity, favorable volume/mass ratio
due to its low density.
The following natural substances, plastics,
and resins can be dissolved in MEK: rosin, ester
resins, pentaerythritol ester resins, Congo ester,
dammar (dewaxed), nitrocellulose, low-molecu-
lar cellulose acetate, cellulose acetobutyrate,
cellulose acetostearate, methyl cellulose, epoxy
resins, nearly all alkyd and phenolic resins, poly
(vinyl acetate), vinyl chloride/acetate mixed
polymerizates, viny lchloride/vinylidene chlo-
ride mixed polymerizates, coumarone indene
resins, sulfonamide resins, cyclohexanone re-
sins, acrylic resins, polystyrene, chlorinated rub-
ber, polyurethane.
Cellulose triacetate, high-molecular cellulose
acetate, poly(vinyl chloride), poly(vinyl butyral),
polysulfide rubber cannot be dissolved in MEK.
Shellac is only partially soluble.
Other areas of application [69, 70] are pro-
duction of paints, lacquers, varnishes, paint thin-
ners and removers, adhesives, cements, sealants,
magnetic tapes, artificial leather, transparent pa-
per, printing inks, cleaner for electronic equip-
ment, cosmetics, pharmaceuticals; degreasing of
metal surfaces; extraction of fats, oils, waxes,
natural resins; dewaxing of mineral oils [71] or
lube oils. Additionally, it is used as synthetic
flavoring agent in foods and pharmaceuticals and
as a sterilizer for bacterial spores on surgical
instruments, hypodermic needles and syringes,
and dental instruments; manufacturing of smoke-
less powder.
In contrast to its uses as a solvent, use as a
chemical feedstock is of minor importance de-
spite the great number of possible reactions;
however, condensation with formaldehyde to
obtain methyl isopropenyl ketone, autoconden-
sation to form ethyl amyl ketone, and mixed
condensation with acetone to obtain methyl amyl
ketone are of interest. MEK is used to produce
perfumes, antioxidants, catalysts, peroxides, and
diacetal. Methyl ethyl ketoxime, used as an
antiskinning agent in lacquers, is of minor im-
2-Butanone 439
portance. Methyl ethyl ketone peroxide is used as
a polymerization initiator for unsaturated polye-
sters. The perfume industry reacts MEK with
citral to obtain perfume components such as
methylpseudoionone. Since 1962 MEK is per-
mitted as an alcohol denaturant in the Federal
Republic of Germany (by decree of Bundesmo-
nopolverwaltung in Offenbach).
7. Economic Aspects
Global demand of MEK was published to be
950 000 t/a in 2001 [72]. The annual growth of
the market is estimated to be around 3 % after a
decline in 2001. The withdrawal of MEK from
the HAP list, as well as the economic growth in
China will positively impact MEK consumption
figures.
Table 6 shows estimated sales volumes per
application [72].
The approximated breakdown of worldwide
consumption of 1  106 t MEK in 2001
amounted to 170 000 t for Western Europe,
Eastern Europe 10 000 t, North America
200 000 t, Central and South America
30 000 t, China 220 000 t, Japan 140 000 t,
Asia 200 000 t (except China and Japan), and
30 000 t in other regions.
MEK is also available under the following
names:
Butanone, 2-butanone, methylacetone, meet-
co, butan-2-one.
8. Toxicology and Occupational
Health
8.1. Occupational Exposure
The NIOSH (National Institute for Occupational
Safety and Health) National Occupational Expo-
sure Survey (1981-1983) reported an estimated
Table 6. Volumes per application (2001)
%
Paints, lacquers, aluminum foil lacquers 63
Adhesives 11
Chemical industry (incl. sound carrier) 12
Dewaxing 5
Printing inks 2
Miscellaneous 7
440 2-Butanone
1 447 456 workers exposed to MEK, of which
245 372 were female. In occupational settings,
the primary routes of exposure to MEK are
inhalation and skin contact. [73]. For different
workplaces (e.g., electronic parts plant, plants
manufacturing or applying surface coatings, shoe
factories) the maximum MEK concentration was
376 ppm (shoe factory). Most values were much
lower [74]. Lesser amounts of MEK are lost to the
air with concurrent worker exposure during man-
ufacture, shipping, repacking, and preparation of
coatings and adhesives. Industrial exposure from
contact with liquid MEK does not appear an
important problem [74].
8.2. Toxicokinetics and Metabolism
8.2.1. Absorption
8.2.1.1. Oral Exposure
MEK is absorbed by the gastrointestinal tract
following oral exposure in humans. Experimen-
tal data from rodents indicate that orally admin-
istered MEK is absorbed from the gastrointesti-
nal tract and rapidly eliminated. Oral adminis-
tration to rats resulted in a mean peak plasma
concentration after 4 h that decreased to less than
1/10 of the peak value after 18 h [75].
8.2.1.2. Inhalation Exposure
MEK is well absorbed during inhalation expo-
sure because of its high blood/air solubility ratio.
In MEK exposed workers, the alveolar air con-
centration was highly correlated with the envi-
ronmental air concentration and averaged 30% of
the latter. Pulmonary retention rates are between
5 and 70 % (MEK between < 100 ppm and
300 ppm in air) [75].
8.2.1.3. Dermal Exposure
The percutaneous absorption of MEK is rapid.
MEK was present in the exhaled air of humans
within 3 min after application to normal skin of
the forearm. A plateau concentration was
reached within 2 h. The absorption rate was
slower when MEK was applied to the dry skin,
where a plateau was attained in 4-5 h. By con-
trast, after absorption of MEK to the moist fore-
Vol. 6
arm, MEK was detected within 30 s in the ex-
haled air and a maximum concentration was
reached in 10-15 min Permeability rates were
0.46 and 0.59  106 g cm2 min1 for in vivo
studies and 88.3  106 g cm2 min1 for in
vitro studies. The dermal uptake to MEK from
the vapor phase contributes approximately 3-
3.5% of the total body burden [75].
8.2.2. Distribution
In MEK exposed workers, the MEK blood levels
were significantly correlated with the environ-
mental MEK concentrations, which indicates
rapid transfer from the lungs to the blood. MEK
tissue/air solubility ratio for human kidney,
liver, muscle, lung, heart, fat, and brain revealed
similar solubility in all these tissues, with the
tissue/air ratio ranging from 147 (lung) to 254
(heart). MEK does not accumulate in fatty tis-
sues in humans. Blood/tissue solubility ratios
for several tissues approach unity. Thus, MEK is
not expected to accumulate in any particular
tissue, which is confirmed in animal studies
[75].
8.2.3. Metabolism
Metabolism of MEK in humans and experimen-
tal animals is very similar. The majority of MEK
is metabolized to 3-hydroxy-2-butanone, which
is subsequently metabolized to 2,3-butanediol.
A small portion is converted to 2-butanol. In
humans exposed to MEK in air, 2-butanol and
2,3-butanediol were identified in serum, while
3-hydroxy-2-butanone and 2,3-butanediol have
been identified as urinary metabolites of MEK. In
animal studies, the majority of MEK is oxidized
by the cytochrome P450 monooxygenase sys-
tem. After exposure, 2-butanol is metabolized
to MEK rapidly. Ultimately, 2-butanol and
MEK are metabolized through the same inter-
mediates [75].
8.2.4. Elimination and Excretion
In human studies involving acute inhalation
exposure, the urinary excretion of MEK and
metabolites and the exhalation of unchanged
Vol. 6
MEK account for only a small percentage of the
absorbed dose. The remainder of the absorbed
dose is rapidly transformed to carbon dioxide and
water through intermediary metabolic pathways
[74]. Nevertheless, unchanged MEK in urine is
used as a marker of exposure since strong posi-
tive correlations have been reported between
MEK levels in urine and MEK levels in air
[75, 76].
8.2.5. Mechanism of Action
Ketone solvents are odorous and slightly irritat-
ing to mucuos membranes and the skin [77]. The
range of acceptable odor thresholds concentra-
tions for MEK varies from 285 ppm. The odor
quality is sharp and sweet [78]. Information on
the mechanisms of toxic action of MEK is rare.
Very high inhalation concentrations (500-
10 000 ppm) caused pulmonary vasoconstric-
tions and hypertension in animals. Interactions
leading to the potentiation off effects, particular-
ly neurotoxicity, by other toxic substances con-
stitute the main hazard of MEK [74]. Studies
regarding the induction of the mixed function
oxidase system showed contradictory results
[79]. The toxicity of MEK may be a result of
exposure to concentrations that exceed the ca-
pacity for detoxification by a saturable enzyme
mechanism. The mechanism by which MEK
potentiates the neurotoxicity of hexacarbon sol-
vents is not entirely clear, although it appears to
involve the biotransformation of these solvents to
their toxic metabolites [75].
8.2.6. Toxic Effects
8.2.6.1. Oral Exposure
Oral exposure of humans to MEK in form of an
accidental ingestion of MEK had no persistent
adverse health effects. LD50 values for adult mice
and rats are 2-6 g per kilogram body weight,
with death occurring within 1-14 days following
a single oral dose. The lowest, nonlethal acute
oral dose producing an adverse effect (renal
tubule necrosis) is 1082 mg/kg MEK in corn oil.
Information on the effects of MEK following
repeated oral exposure is limited to data for 2-
butanol (a metabolic precursor of MEK) and for
3-hydroxy-2-butanone (a metabolite).
2-Butanone 441
8.2.6.2. Inhalation Exposure
Evidence for neurotoxic effects following inha-
lation exposure to MEK is limited to a small
number of case reports of neurological im-
pairment in occupationally-exposed humans and
in one study of problematic design reporting
increased incidence of subjectively reported neu-
rological symptoms in MEK-exposed workers.
Behavioral effects and narcosis after single or
limited number of inhalation experiments in rats
and mice were observed. However, several well-
conducted studies provided no evidence for neu-
rological effects of MEK in animals.
Developmental effects following exposure to
MEK have not been described in humans. In
rodents MEK caused developmental toxicity in
the presence of maternal toxicity in rats and mice
and in one study in rats in the absence of maternal
toxicity. Inhalational studies provide evidence
for developmental effects (decreased fetal
weight, increased incidence of certain skeletal
variants) in rats and mice exposed to 3000 ppm
MEK, 7 h per day during gestation, but not at
1000 ppm and lower.
Available data provide no clear evidence for
other systemic effects resulting from inhalation
exposure to MEK. A subchronic inhalation study
of MEK found no persistent body weight
changes, gross behavioral changes or histologi-
cal changes in major tissues and organs in rats
exposed 6 h per day, 5 days per week for 90
days to concentrations as high as 5000 ppm.
Some changes in organ weight and clinical pa-
thology parameters were observed; however,
these were not supported by histological changes.
There is no evidence for portal of entry effects
following inhalation exposure to MEK. MEK
exposures up to 200 ppm for up to 4 h did not
cause irritations. Exposure to 300 ppm MEK was
reported as intolerable. Nasal irritation was noted
in rats exposed to 6000 ppm MEK for 15 weeks,
but not in other studies involving somewhat
lower exposure concentrations. No exposure-
related upper respiratory irritation could be eval-
uated in rats exposed up to 5000 ppm MEK for
90 days. In addition, respiratory irritation was not
reported in dams exposed to 3000 ppm MEK,
7 h per day for days 6-15 of gestation. In preg-
nant rodents developmental effects are the most
sensitive, toxicologically relevant endpoints for
inhalation exposure to MEK.
442 2-Butanone
The few available epidemiological studies of
MEK-exposed workers provide no clear evi-
dence of cancer hazard, but the studies are gen-
erally inadequate to discern an association be-
tween MEK exposure and an increased incidence
of cancer. Epidemiological evidence is based on
a small number of site-specific deaths, only, and
studies are confounded by exposure to multiple
chemicals. A case control study examining the
association between paternal exposures to sever-
al solvents, including MEK, and childhood leu-
kemia is exploratory in scope and cannot be used
to reliably support the existence of any such
association. Although there is some suggestion
of increased risk for certain cancers (including
bone and prostate) involving multiple solvent
exposure that include MEK, there is no clear
evidence for a relationship between these cancers
and MEK exposure alone. There are no chronic
toxicity studies or cancer bioassays of inhalation
exposure to MEK in experimental animals.
MEK is not mutagenic in a number of con-
ventional short-term assays for genotoxic poten-
tial [75].
8.2.6.3. Occupational Health
Chronic co-exposure to MEK and either un-
branched aliphatic hexacarbon or haloalkane
solvents represents a significant potential occu-
pational hazard. Serious toxic effects could occur
[74]. Symptoms produced by an overexposure
include irritation of the eyes, nose, and throat,
headache, nausea, vertigo, uncoordination, cen-
tral nervous system depression, narcosis, and
cardiorespiratory failure. Recovery is usually
rapid and without residual toxic effects [78]. The
potential exists for increased susceptibility to
neurotoxicity, hepatotoxicity, and renal toxicity
following exposure to MEK in combination with
certain other solvents. MEK potentiates the neu-
rotoxicity of hexacarbon solvents (n-hexane,
methyl-n-butyl ketone, and 2,5-hexanedione)
and the liver and kidney toxicity of haloalkane
solvents. Although the mode by which MEK
potentiates the neurotoxicity of hexacarbon sol-
vents is not entirely clear, it appears to involve
alterations in their metabolism to toxic metabo-
lites. The potentiating effects of MEK on the
toxicity of other solvents have been demonstrat-
ed at relatively high concentrations (200-
1000 ppm) [75, 80].
Vol. 6
Although MEK appears a relatively safe or-
ganic solvent, its use in combination with other
solvents, in particular haloalkanes or unbranched
aliphatic hydrocarbons, should be avoided. All
necessary precautions have to be taken to ensure
that workers are not exposed to both MEK and
solvents whose toxicity is potentiated by MEK
[74]. In the case of accident spills, personnel
should wear protective clothing including
respiratory protection. Contaminated clothing
should be removed promptly, and the exposed
areas of the body should therefore be thoroughly
flushed with water. MEK may be absorbed
through the skin. Therefore, caution should be
exercised to avoid repeated or prolonged skin
contact [78].
Under normal occupational conditions, ambi-
ent MEK air concentrations and urinary concen-
trations of MEK correlate significantly. There-
fore, a biological limit value (BLV) could be
evaluated. Given an air concentration of
200 ppm MEK, the individual urinary MEK
concentration may range from 2.15.4 mg/L.
Urinary MEK concentration may be measured
using headspace gas chromatography [76].
8.2.6.4. Regulations
The OSHA PEL, the NIOSH REL TWA and the
ACGIH TLV-TWA for MEK as well as the
threshold limit value (MAK value) in Germany
are 200 ppm [81, 82]. The ACGIH TLV-STEL
and the NIOS REL STEL are 300 ppm [78].
The biological limit value (BAT value) for
MEK in urine is 5 mg MEK per liter in Germany
[76]. Potential exposures to MEK emitted
from industrial processes may not reasonably be
anticipated to cause human health or environ-
mental problems. Therefore, MEK was
removed from the list of hazardous air pollutants
(HAPs) [83].
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Further Reading
A. E. Comyns: Encyclopedic Dictionary of Named Processes
in Chemical Technology, 3rd ed., CRC Press, Boca Raton,
FL 2007.
T. S. S. Dikshith: Safe Use of Chemicals, CRC Press, Boca
Raton, FL 2009.
S. Ebnesajjad (ed.): Adhesives Technology Handbook, 2nd
ed., William Andrew Publ., Norwich, NY 2008.
C. M. Hansen: Hansen Solubility Parameters, 2nd ed., CRC
Press, Boca Raton, FL 2007.
P. Patnaik: A Comprehensive Guide to the Hazardous Prop-
erties of Chemical Substances, 3rd ed., Wiley, Hoboken,
NJ 2007.
E. M. Petrie: Epoxy Adhesive Formulations, McGraw-Hill,
New York, NY 2006.
P. A. Schweitzer: Paint and Coatings, CRC Taylor & Francis,
Boca Raton, FL 2006.
Z. W. Wicks, F. N. Jones, S. P. Pappas, D. A. Wicks: Organic
Coatings, 3rd ed., Wiley-Interscience, Hoboken, NJ
2007.