2-Butanone 1

2-Butanone
Wilhelm Neier, Deutsche Texaco AG, Moers, Federal Republic of Germany

Guenter Strehlke, Deutsche Texaco AG, Moers, Federal Republic of Germany

1. Introduction . . . . . . . . . . . . . . . . . 1 4.3. Direct Oxidation of

2. Physical Properties . . . . . . . . . . . . 2 n-Butenes (Hoechst-Wacker Process) 4
3. Chemical Properties . . . . . . . . . . . 2 5. Quality, Storage, Transportation . . . 5
4. Production . . . . . . . . . . . . . . . . . . 3 6. Uses . . . . . . . . . . . . . . . . . . . . . . 5
4.1. Catalytic Dehydrogenation of
7. Economic Aspects . . . . . . . . . . . . . 6
sec-Butyl Alcohol (SBA)
in the Gaseous Phase . . . . . . . . . . . 3 8. Toxicology . . . . . . . . . . . . . . . . . . 6
4.2. Liquid-Phase Oxidation of n-Butane . 4 9. References . . . . . . . . . . . . . . . . . . 7

1. Introduction Moreover, MEK can be used as an activator

for oxidative reactions, as a selective extractant,
2-Butanone [78-93-3], methyl ethyl ketone, as a special solvent for dewaxing mineral oil
MEK, is the second link in the homologous se- fractions, and as a chemical intermediate. (see
ries of aliphatic ketones and, next to acetone, the Table 1).
most important commercially produced ketone.
Table 1. Physical data of 2-butanone [9], [10]
2-Butanone is produced primarily by dehydro-
genation of 2-butanol, analogous to the produc- Mr 72.11
tion of acetone by dehydrogenation of gaseous mp, ◦ C − 86.9
bp, ◦ C 79.6
isopropyl alcohol on copper, zinc, or bronze cat- Relative density,
alysts at 400 – 550 ◦ C. At 80 – 95 % sec-butyl d 20
4 0.8045
d 20
alcohol conversion, MEK selectivity is > 95 %. 20 0.80615
Refractive index, n20D 1.3788
In some cases MEK can be produced in the same Evaporation number (ether=1) 2.6
facilities as acetone. Butenes (dehydration) and Critical temperature, ◦ C 262.45
Critical pressure, MPa 4.15
higher ketones (autocondensation) are byprod- Critical density,
, g/L 0.270
ucts. In 1995, 730 000 t of MEK were produced Dynamic viscosity at 20 ◦ C, mPa · s 0.323
worldwide. Surface tension at 20 ◦ C, mN/m 24.6
Molar heat cp at 23.8 ◦ C, J mol−1 K−1 160.8
2-Butanone is produced by ARCO (US), Heat of fusion, J/mol 7456
AKZO (NL), Biochimica (ES), BP (GB), Car- Heat of vaporization at 79.6 ◦ C, J/mol 31.2
Combustion enthalpy at constant
bochlor (Argent.), Celanese (US, CA, Mexico), pressure, 25 ◦ C, kJ/mol 2444.3
Esso (GB, US), Maruzen (JP), PCUK (FR), Thermal conductivity, W m−1 K−1
Shell (FR, NL, US, CA), Texaco (FRG), Tonen at 0 ◦ C 0.150
20 ◦ C 0.145
(JP), UCC (US), Sasol (ZA). Interest in MEK as 50 ◦ C 0.137
a solvent for paints and adhesives has been grow- Solubility at 20 ◦ C
2-butanone in water, mass fraction, % 27.5
ing since the 1980s. In general, MEK is consid- water in 2-butanone, mass fraction, % 12.5
ered to be a competitor for ethyl acetate, espe- Flash point (DIN 51755), ◦ C −1
cially as a low-boiling solvent. It has broad ap- Explosion limits in air at 20 ◦ C, 101.3 KPa,
lower, volume fraction, % 1.8
plication as a solvent for nitrocellulose, cellulose upper, volume fraction, % 11.5
acetate – butyrate, ethylcellulose, acrylic resins, Ignition temperature, ◦ C 505
Ignition class (VED) G1
vinylacetates, and vinylchloride – vinylacetate Explosion class (VED) 1
copolymer (based on synthetic surface-coating Electric conductivity at 20 ◦ C, Ohm−1 cm−1 5×10−8
preparation). It is favored as a lacquer solvent Dipole moment, Debye 3.18
Dielectric constant of the liquid at 20 ◦ C 15.45
because of its low viscosity, high solids concen-
tration, and great diluent tolerance.

c 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

10.1002/14356007.a04 475
2 2-Butanone

2. Physical Properties 2-Butanone is unsaponifiable and, unlike es-

ters, does not form corrosive products upon hy-
2-Butanone, methyl ethyl ketone, MEK, drolysis. It is heat and light stable. It decom-
CH3 COCH2 CH3 , is a relatively mobile, col- poses only after prolonged UV exposure (yield-
orless liquid. Its typical odor resembles that of ing ethane, methane, carbon monoxide, ethyl-
acetone. The compound is only partially water- ene, and diacetyl) [13].
miscible, whereas it is completely miscible with Diacetyl [431-03-8] is formed by oxidation
most organic solvents. 2-Butanone forms binary with airin the presence of special catalysts [14].
and ternary azeotropic mixtures in combination Methyl ethyl ketone peroxide [19393-67-0],
with water and several other organic solvents a polymerization catalyst, is formed by oxida-
(see Table 2). tion with a 30 % solutionof hydrogen peroxide
Table 2. Binary azeotropic mixtures containing MEK [11]
[15]. Nitric acid and other strong oxidants oxi-
dize MEK to a mixture of formic and propionic
Second component Mass bp at acids [15].
fraction 1013 hPa,
of MEK ◦
C
sec-Butyl alcohol [78-92-2] is obtained by
catalytic reduction with hydrogen [15]. It can
Water 88.7 73.4 also be formed by electrolytic reduction in
Benzene 37.5 78.4
n-Hexane 29.5 64.3 sodium acetate solution or by reduction with
n-Heptane 73.0 77.0 ammonium amalgam or lithium aluminum hy-
Cyclohexane 40 72
1,3-Cyclohexadiene 40 73
dride. 3,4-Dimethyl-3,4-hexanediol is obtained
Methanol 30.0 63.5 by electrolytic reduction in an acidic medium or
Ethanol 60.9 74.0 by reduction with magnesium amalgam [15].
Isopropyl alcohol 68.0 77.5
tert-Butyl alcohol 73 77.5 Methyl ethyl ketone forms addition products
Ethyl acetate 18.0 77.0 with hydrogen cyanide as well as with sodium
Methyl propionate 52 79.25
Propyl formate 55 79.45
and potassium hydrogen sulfites. In an alkaline
Chloroform 96.0 79.65 medium MEK condenses with aldehydes to form
Carbon tetrachloride 71.0 73.8 higher unsaturated ketones. Condensation with
Carbon disulfide 15.3 45.85
Propyl mercaptan 75 55.5 formaldehyde to form methyl isopropenyl ke-
Thiophene 55.0 76.0 tone [563-80-4], an intermediatefor further syn-
Ethyl sulfide 20 77.5
theses, is of particular interest. During base-
catalyzed autocondensationin the liquid phase
2-Butanone does not form a binary azeotropic and during gase-phase condensation on alkalin-
mixture with toluene, m-xylene, n-butanol, ized copper catalysts, the carbonyl group reacts
isobutanol, sec-butyl alcohol, 4-methyl-2- with the methyl group, whereas during acid-
pentanol, allyl alcohol, acetic acid methyl es- catalyzed condensation the methylene group in
ter, acetic acid isopropyl ester, acetic acid n- α-position to the carbonyl group is attacked [16].
butyl ester, acetic acid isobutyl ester, 1,1-di-
chloroethane, isobutyl chloride, propyl bro-
mide, ethyl iodide, trichloroethylene, dichloro-
bromomethane, isobutyl bromide, formic acid,
and acetic acid.
2-Butanone forms ternary azeotropes with
water/benzene and water/carbon tetrachloride
[11].
Methyl ethyl ketone and citral [5392-40-5]
condense toform methylpseudoionone that can
3. Chemical Properties be cyclized to methylionone, a compound used
for producing synthetic violet perfume.
Under normal conditions and in the absence of During condensation with low-molecular
atmospheric oxygen MEK is stable. Care must aldehydes (during base-catalyzed and acid-
be taken after prolonged storage because perox- catalyzed aldolization) the α-position of the car-
ides may form in the presence of oxygen [12]. bonyl group is first occupied [17], [18].

Thus, the base-catalyzed aldolization with
less than amounts of formaldehyde yields 2-
methyl butane-1-ol-3-one [17] and exhaustive
hydroxymethylation, with reduction of the car-
bonyl group (crossed Cannizzaro reaction), pro-
duces desoxyanhydroeneaheptite [19].
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] [20].
Methyl ethyl ketone reacts with polyoxy
compounds or epoxides to form cyclic products.
Amyl nitrite [110-46-3] attacks the CH2
groupin α-position to the carbonyl group and
yields themonooxime of diacetyl.
The keto group reacts with amino groups
with elimination of water. In combination with
hydroxylamine [7803-49-8], methyl ethylke-
toxime, an antiskinning agent, is formed.
Condensation of MEK with aliphatic esters
and anhydrides gives β-diketones.
Phenols react with MEK to form oxypheny-
lene compounds. In combination with phenol,
2,2-hydroxyphenyl butane is obtained, a ho-
molog of hydroxyphenyl propane (Bisphenol A
[80-05-7] ), an important materialfor the produc-
tion of synthetic resins.
Methyl ethyl ketone can be halogenated in
the α-position. Methyl ethyl ketone reacts with
Grignard compounds to form tertiary alcohols.
With acetylene in the presence of sodium amide
3-methyl-1-pentyn-3-ol [77-75-8] is formed.
N-Methyl-formyl-aminobutaneis obtained from
MEK plus N-methylformamide. The Refor-
matzky reaction produces the β-oxyester from
monobromine-substituted esters [20].
2-Butanone 3
4. Production
Most MEK (88 %) is produced today by dehy-
drogenation of sec-butyl alcohol (SBA). SBA
can easily be produced by hydration of n-butenes
(from petrochemically produced C4 raffinates)
in a two-step process (catalyst: sulfuric acid),
or in a single-step process by direct addition of
water, acidic ion-exchange resins being used as
a catalyst [21]. The remaining 12 % MEK is
produced by processes in which liquid butane
is catalytically oxidized, giving both acetic acid
and MEK [22].
The direct oxidation of n-butenes (Hoechst-
Wacker process, Maruzen process, [23], [24] )
has not been generally accepted, because of un-
desired byproducts.
The sec-butylbenzenehydroperoxide route
giving phenol and MEK by acid-catalyzed split-
ting [25] is uneconomical. The autoxidation of
liquid sec-butyl alcohol, giving MEK and hydro-
gen peroxide [26], and the catalytic oxidative hy-
dration of gaseous n-butenes [27] are also uneco-
nomical. The oxidation of n-butenes with ethyl-
benzenehydroperoxide to form butylene oxides,
and subsequent hydration and formation of ke-
tones appears to be moderately attractive [28].
Styrene, n-butanol, and MEK are obtained in
coupled production.
4.1. Catalytic Dehydrogenation of
sec-Butyl Alcohol (SBA) in the Gaseous
Phase
The catalytic dehydrogenation of SBA is an en-
dothermic reaction (51 kJ/mol). The equilibrium
constant for SBA can be calculated as follows
[29]:
log Kp = −2.790 × T −1 +1.51log T +1.865
(T = reactiontemperature, inK)
The MEK concentration in the reaction mixture
increases with the temperature and reaches its
maximum at approx. 350 ◦ C [30].
Copper [31], zinc [32], or bronze [33] are
used as catalysts in gas-phase dehydrogena-
tion. The latter two require high dehydrogena-
tion temperatures (400 ◦ C). Dehydration of SBA
to butenes takes place as a side reaction on
4 2-Butanone
zinc oxide. Platinum on alumina [34], copper
or chromium [35], [36] as well as copper, and
zinc on alumina [34] are recommended as dehy-
drogenation catalysts for aqueous SBA.
Commercially used catalysts are reactivated
by oxidation, after 3 to 6 months use. They have
a life expectancy of several years. Catalyst life
and alcohol conversion are impaired by contam-
ination with water, butene oligomers, and di-sec-
butyl ether [37].
Deutsche Texaco developed a process in
which practically anhydrous sec-butyl alco-
hol has been produced since 1983 by di-
rect hydration of n-butene, catalyzed by acidic
ion-exchange resin; it is then dehydrogenated
on a copper-based precipitating catalyst at
240 – 260 ◦ C under normal pressure [21], [31].
The LHSV (4 L/L of catalyst · h), the conversion
(90 – 95 %), and the catalyst life until reactiva-
tion becomes necessary (3 – 4 months) render
the process economically attractive. (see Fig-
ure 1).
Figure 1. Gaseous-phase dehydrogenation of sec-butyl al-
cohol (Deutsche Texaco AG process)
a) Reactor; b) Oil circulation heating; c) Condenser; d) Sep-
arator; e) Refrigerator; f) Distillation
sec-Butyl alcohol is dehydrogenated in a
multi-tube reactor. The reaction heat (51 kJ/mol)
is supplied by heat transfer oil. The reaction
products leave the reactor as a gas and are split
into liquid crude MEK and hydrogen on cooling.
The hydrogen is purified by further cooling. The
reaction is highly selective. Autocondensation
to higher ketones (e.g., 5-methyl-3-heptanone)
is much lower in comparison to acetone. In ad-
dition, the dehydration to butenes on copper cat-
alysts is for the most part prevented.
During reaction and subsequent treatment,
practically no waste disposal problems arise.
Table 3 lists further processes for the pro-
duction of MEK by gas-phase hydrogenation of
sec-butyl alcohol.
4.2. Liquid-Phase Oxidation of n-Butane
2-Butanone is a byproduct in the liquid-phase
oxidation of n-butane to acetic acid. Autoxida-
tion of n-butane takes place in liquid phase ac-
cording to a radical mechanism yielding MEK as
an intermediate and acetic acid as the end prod-
uct. The continuous plug flow process developed
by Union Carbide allows the partial collection
of MEK intermediate [42]. MEK and acetic acid
(mass ratio 0.15 – 0.23 : 1.0) are obtained by
non-catalyzed liquid-phase oxidation at 180 ◦ C
and 5.3 MPa (53 bar) with remixing. Continuous
oxidation under plug flow conditions at 150 ◦ C,
6.5 MPa (65 bar), and a residence time of 2.7 min
forms MEK and acetic acid at mass ratios of up to
3 : 1 [42]. Celanese uses acetic acid as a solvent
and cobalt acetate and sodium acetate as homo-
geneously dissolved catalysts [43]. It is a batch
process performed at 160 – 165 ◦ C and 5.7 MPa
(57 bar). MEK and acetic acid are obtained at a
mass ratio of 0.4 : 1.0.
4.3. 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 [44], [45].
The salt pair is subsequently reoxidized.
n-Butenes can be converted into the follow-
ing reaction products (conversions of up to 95 %
are attained):
Reaction products: Selectivities, mol %
MEK 86
n-Butyraldehyde 4
Chlorinated products 6
Carbon dioxide 1
The main disadvantages are: formation of
chlorinated butanones and n-butyraldehyde and
corrosion caused by free acids.
 2-Butanone 5
Table 3. Further processes for producing methyl ethyl ketone by gase-phase dehydrogenation of sec-butyl alcohol

Company Catalyst H2 O Tem- Pressure, Con- Selec- Yield, Ref-

content, perature, version, tivity, er-
◦
vol % C MPa % mol % mol % ence

Standard Oil ZnO/Bi2 O3 0 400 0.1 – 0.3 80 [38]

Esso Research & Eng. ZnO/Na2 CO3 /Al2 O3 0 413 96 – 97 97 93 – 94 [39]
Maruzen Oil bronze 0 390 0.3 80 99 79.2 [33]
Knapsack Griesheim CuO/CrO 0 270 – 320 88 – 93 93 – 96 [40]
Toyo Rayon CuO/NaF/SiO2 300 96 100 [41]
Ruhrchemie 60 % Cu, Cr2 O3 , 260 90 100 90 [35]
MgO, 12 % SiO2 ,
10 % H2 O
Veba-Chemie 22 % Cu, 90.4 180 57.3 a 63 b 97.8 c [36]
8 % BaCrO4 ,
2 % Cr2 O3 ,
0.5 % Na2 O,
61 % SiO2
Shell-Chemie 0.05 % Pt/Al2 O3 0 358 0.6 92.5 – 93.5 96.3 90 [37]
Shell-Chemie 5 % Cu, 5 % Cr/Al2 O3 0 286 0.6 81 – 85 86 – 92 73 – 77 [37]
a
Relative to sec-butyl alcohol.
b
Relative to di-sec -butyl ether.
c
Total yield.

The Maruzen process is similar [46], [47].
Oxygen is transferred by an aqueous solution of
palladium sulfate and ferric sulfate.
Other processes employing the same oxygen
transfer principle were developed by Consor-
tium für Elektrochemie [48] and Eastman Kodak
[49]. For further processes, see [50–53].
5. Quality, Storage, Transportation
It is possible to produce high-purity MEK
(DIN 53247, ASTM D 740, BS 1940).
The present sales specifications of Deutsche
Texaco AG are listed in Table 4.
Table 4. Sales specifications for MEK
Purity, wt % GC
d 20
4 (DIN 51757)
d 20
20
Boiling range, ◦ C DIN 51751
ASTM D 1078
Acidity
(as acetic acid), mg KOH/g
Water content, wt %, DIN 51777
ASTM D 1364
Color (Pt – Co, APHA), ASTM D 1209
Nonvolatile matter, wt %
A stable dilute potassium permanganate so-
lution indicates high purity (permanganate time
according to ASTM D 1363).
Storage life of MEK is limited. Carbon steel
containers (ST 3529) are suitable for short-
term storage and transportation. Stainless steel
(316 SS) or containers with a tin lining are rec-
ommended for long-term storage. Once auto-
catalysis has started, it continues even if storage
is continued in inert containers. During long-
term storage the formation of peroxide must
be prevented. Since MEK is somewhat hygro-
scopic, water is absorbed from the air.
The following regulations for transportation
of MEK must be observed [54].
IMDG-Code: D 3308, Kl. 3.2 UN no. 1193,
RID, ADR, ADNR: class 3, Rn 301, 2301, and
6301 respectively, no. 1 a, category Kl n; Eu-
ropean Council, Yellow Book 78/79: no. 606-
002-00-3; European Communities: Guideline/D
VgAst, no. 606-002-00-3; UK: Blue Book,
Fla.L. IMDG-Code E 3080; USA: CFR 49,
min. 99.7
172.101, Fla.L.; IATA RAR: art. no. 726 Fla.L.
0.804 – 0.806
0.805 – 0.807
within 0.5
incl. 79.6 6. Uses
0.0001
MEK is an important solvent with properties
max. 0.1 similar to those of acetone. MEK has the fol-
max. 10
max. 0.002
lowing advantages in comparison to other sol-
vents with comparable rates of evaporation: very
high power of dissolution, high ratio of dissolved
matter to viscosity, miscibility with a large num-
ber of hydrocarbons without impairing the solids
content or viscosity, favorable volume/mass ra-
tio due to its low density.
6 2-Butanone
The following natural substances, plas-
tics, and resins can be dissolved in MEK:
rosin, ester resins, pentaerythritol ester resins,
Congo ester, dammar (dewaxed), nitrocellu-
lose, low-molecular cellulose acetate, cellulose
acetobutyrate, cellulose acetostearate, methyl-
cellulose, epoxy resins, nearly all alkyd and
phenolic resins, polyvinylacetate, vinylchlo-
ride/acetate mixed polymerizates, vinylchlo-
ride/vinylidene chloride mixed polymer-
izates, coumarone – indene resins, sulfonamide
resins, cyclohexanone resins, acrylic resins,
polystyrene, chlorinated rubber, polyurethane.
Cellulose triacetate, high-molecular
cellulose acetate, poly(vinylchloride),
poly(vinylbutyral), polysulfide rubber cannot
be dissolved in MEK. Shellac is only partially
soluble.
Other areas of application are production
of synthetic leather, transparent paper, print-
ing inks, aluminum foil lacquers; degreasing of
metal surfaces; extraction of fats, oils, waxes,
natural resins; dewaxing of mineral oils [55].
In contrast to its uses as a solvent, use as a
chemical feedstock is of minor importance de-
spite the great number of possible reaction; how-
ever, condensation with formaldehyde to ob-
tain methyl isopropenyl ketone, autocondensa-
tion to form ethyl amyl ketone, and mixed con-
densation with acetone to obtain methyl amyl
ketone are of interest. Methyl ethyl ketoxime,
used as an antiskinning agent in lacquers, is of
minor importance. Methyl ethyl ketone perox-
ide is used as a polymerization initiator for un-
saturated polyesters. Diacetyl serves as a but-
ter flavorer. The perfume industry reacts MEK
with citral to obtain perfume components such
as methylpseudoionone. Since 1962 MEK is
permitted as an alcohol denaturant in the Fed-
eral Republic of Germany (by decree of Bun-
desmonopolverwaltung in Offenbach).
7. Economic Aspects
Table 5 shows the 1979 sales (in %) for the vari-
ous markets in the Federal Republic of Germany.
The worldwide consumption of MEK in
1979 amounted to 642000 t (Western Eu-
rope 166000 t, Eastern Europe 18000 t, North
America 315000 t, Central and South Amer-
ica 34000 t, Asia, Australia, Oceania 100000 t,
Africa 9000 t).
Table 5. Sales survey (FRG, 1979)
%
Paints, lacquers, printing inks, aluminum foil
lacquers 40
Coating and printing of plastics 20
Chemical industry (incl. sound carrier),
pharmaceutical industry 13
Adhesives 11
Miscellaneous 16
MEK is also available under the following
names:
German: Ethylmethylketon, Acetonersatz, β-
Ketobutan, 2-Butanon
English: Butanone, 2-butanone, MEK, methy-
lacetone, meetco
French: Méthyléthylcétone, butane-2-one,
ethylméthylcétone, MEC
8. Toxicology
The odor threshold of MEK is 10 ppm; both,
MAK and TLV are established at 200 ppm. The
inhalation of MEK vapor has narcotic effects.
The vapor irritates the eyes and the nasal and
pharyngeal mucous membranes [54]. Frequent
and prolonged contact with liquid MEK causes
skin moisture loss and slight irritation [56]. Sen-
sitive persons may develop dermatoses [57].
Liquid MEK temporarily irritates the eye and
corneas [56].
MEK is usually absorbed through the respira-
tory tract. It may also be absorbed by the skin, but
the cutaneous LD50 in rabbits is above 8 mL/kg
[57]. The MEK metabolism has been studied in
guinea pigs. MEK is both reduced to 2-butanol
and oxidized to 3-hydroxy-2-butanone. How-
ever, unlike 2-hexanone and n-hexane, which
are further oxidized to form neurotoxic 2,5-
hexanedione after oxidation of the ω-1 C atom,
the hydroxybutanone is not further oxidized, but
converted to 2,3-butanediol [58].
Animal tests have shown that the neurotoxic
effect of 2-hexanone may be potentiated by si-
multaneous administration of MEK [59], [60].
The chronic inhalation of 200 ppm (MAK, TLV)
does not seem to be harmful [61].

Even workroom concentrations of 500 –
700 ppm over an extended period of time do not
cause permanent damage.
The LD50 (oral, rat) is 2500 – 3400 mg/kg
[62], [63].
Toxic concentrations for water organisms
[54]: average lethal concentration for fish:
5600 mg/L. Maximum permissible concentra-
tions for Pseudomonas putida: 1150 mg/L,
for Scenedesmus quadricanda: 4300 mg/L,
for Microcystis aeruginosa: 120 mg/L. For
small crabs (Daphnia magma) the LC0 is
2500 mg/L, the LC50 is 8890 mg/L, and the
LC100 > 10000 mg/L.
9. References
General References
1. Beilstein 1, 668, 1(1), 347, 1(2), 726, 1(3),
2770, 1(4), 3243.
2. F. Asinger: Die Petrolchemische Industrie,
Akademie Verlag, Berlin 1971, p. 1086.
3. J. Mellan: Ketones, Chemical Publ., New
York 1968.
4. Winnacker-Küchler: Organische
Technologie II, vol. 6, Hanser Verlag,
München 1982, pp. 77, 81.
5. Römpps Chemie Lexikon, 8th ed., vol. 1,
p. 541.
6. G. Hommel: Handbuch der gefährlichen
Güter, Springer Verlag, Berlin 1980.
7. Kirk-Othmer, 3rd ed., vol. 13, p. 894.
8. Ullmann, 4th ed., vol. 14, p. 193 ff.
Specific References
9. VDI-Wärmeatlas 1983, VDI-Verlag
Düsseldorf.
10. A. Weissberger: Organic Solvents, vol. II, 3rd
ed., Wiley-Interscience, New York 1970.
11. L. H. Horsley: Azeotropic Data, Advances in
Chemistry Series 116, Am. Chem. Soc.,
Washington D.C. 1973.
12. O. L. Mageli, J. R. Kolczynski, Lucidol
Division, Wallace & Tiesman Inc., Encycl.
Polym. Sci. Technol. 1964 – 1972, vol. 9, 831;
N. A. Milas, J. Am. Chem. Soc. 81 (1959)
5824.
13. W. Davis Jr., Chem. Rev. 40 (1947) 240 – 244.
14. Beilstein (Syst. No. 95) 1, 769, 1(1), 397,
1(2), 824, 1(3), 3098.
15. Beilstein 1, 668, 1(1), 347, 1(2), 726, 1(3),
2770, 1(4), 3243.
2-Butanone 7
16. A. T. Nielsen, Organic Reactions, vol. 16, J.
Wiley & Sons, New York 1968, p. 20.
17. Rheinpreußen AG, CA 605368, 1955 (W.
Grimme, J. Wöllner).
18. Rheinpreußen AG, DE 1198814, 1963 (J.
Wöllner, F. Engelhardt).
19. J. R. Roach, H. Wittcoff, S. E. Miller J. Am.
Chem. Soc. 69 (1947) 2651.
20. Technical Brochure LB 11, Deutsche Shell,
Frankfurt (Main) 1976.
21. Erdöl Informations-Dienst A. M. Stahmer,
vol. 37, no. 28 (1984).
22. Union Carbide, US 3196182, 1965 (R. N.
Cox).
23. Hoechst, US 3215734, 1965 (E.
Katzschmann).
24. Maruzen Oil, JP 46-2010, 1971.
25. Union Carbide, DE-OS 2300903, 1973 (F. P.
Wolf).
26. N. V. de Bataafsche Petroleum Maatschappij,
DE 935503, 1955.
27. Stamicarbon, NL 69, 016990, 1971 (J. W.
Geus, J. H. Kruit, P. P. Nobel).
28. SRI-Report, PEP-Review no. 80-3-1 (1981),
Menlo Park, California.
29. H. J. Koll et al., J. Am. Chem. Soc. 67 (1945)
1084.
30. C. Padovani et al., Riv. Combust. 5 (1951) 81.
31. Rheinpreußen AG, DE 1147933, 1958 (R.
Langheim, H. Arendsen).
32. Esso, US 2885442, 1959 (W. J. G. McCullock,
I. Uirshenbaum).
33. Maruzen Oil, Technical Brochure, Aug. 1969.
34. Shell, DE-OS 2028350, 1970 (B. Stouthamer,
A. Kwantes).
35. Ruhrchemie AG, DE-OS 2347097, 1973 (W.
Rottig, C. O. Frohning, H. Liebern).
36. Veba-Chemie, DE-OS 1913311, 1969 (W.
Ester, W. Heitmann).
37. Shell, DE 2028350, 1970 (B. Stouthamer, A.
Kwantes).
38. Standard Oil, US 2436970, 1948 (V. F.
Mistretta).
39. Esso, US 2835706, 1958 (C. E. Cordes).
40. Knapsack-Griesheim, DE 1026739, 1958 (W.
Opitz, W. Urbanski).
41. Toyo Rayon, JP 43-3163, 1968.
42. Union Carbide, US 3196182, 1965.
43. Celanese, US 2704294, 1955 (C. S. Morgan,
N. C. Robertson).
44. Consortium f. Elektrochemie, GB 878777,
1961.
45. J. Smidt et al., Erdöl Kohle Erdgas Petrochem.
16 (1963) 560.
46. Maruzen Oil, JP 46-2010, 1971.
8 2-Butanone
47. Maruzen Oil, DE 1951759, 1970 (N.
Irinchijma, H. Taniguchi).
48. Consortium f. Elektrochemie, US 3080425,
1963 (J. Smidt, W. Hafner, R. Jira).
49. Eastman Kodak, GB 1099348, 1968 (H. J.
Hagemeyer, F. C. Canter).
50. Union Carbide, DE-OS 2300903, 1973 (F. P.
Wolf).
51. Union Carbide, DE-OS 2421168, 1974 (B. J.
Argento, E. A. Rick).
52. F. Conssenant, US 2829165, 1958.
53. C. S. Cronan, Chem. Eng. Int. Ed. 67 (1960)
Feb. 8, 63.
54. G. Hommel: Handbuch der gefährlichen
Güter, Springer Verlag,
Berlin-Heidelberg-New York 1980.
55. W. P. Gee et al., Refine. Nat. Gasoline Manuf.
15 (1936) no. 6, 205.
56. H. F. Smyth Jr., Am. Ind. Hyg. Ass. Q. 17
(1956) 129.
1,4-Butenediol → Butanediols, Butenediol, and Butynediol
Butene Polymers → Polyolefins
57. G. D. Clayton, F. E. Clayton (eds.): Patty’s
Industrial Hygiene and Toxicology, 2nd rev.
ed., vol. 2, Wiley Interscience, New York
1962.
58. Di Vincenzo et al., Toxicol. Appl. Pharmacol.
36 (1976) 511.
59. K. Saida et al., J. Neuropath. Exp. Neurol. 35
(1976) 207.
60. S. N. Ducket, Experientia 30 (1974) 1283.
61. M. T. Okawa, U.S. Nat. Techn. Inform. Serv. P.
B. Rep. 1973, no. 229 166/46 A, Avail NTIS,
Gov. Rep. Announce (US), 74 (10) 51 (1974).
62. E. T. Kimura, M. E. Donn, W. P. Dodge,
Toxicol. Appl. Pharmacol. 19 (1971) 699.
63. N. J. Sax: Dangerous Properties of Industrial
Materials, 3rd ed., Van Nostrand Reinhold,
New York 1969, p. 495.