2-Butanone

Wilhelm Neier, Deutsche Texaco AG, Moers, Federal Republic of Germany

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

Introduction . . . . . . . . . . . . . . . .
Physical Properties . . . . . . . . . . .
Chemical Properties . . . . . . . . . .
Production . . . . . . . . . . . . . . . . .
Catalytic Dehydrogenation of
sec-Butyl Alcohol (SBA)
in the Gaseous Phase . . . . . . . . . .
4.2. Liquid-Phase Oxidation of n-Butane

2-Butanone

2. Physical Properties

2-Butanone

1.
2.
3.
4.
4.1.

.
.
.
.
.
.

1
2
2
3

3
4

1. Introduction
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-Butanone is produced primarily by dehydrogenation of 2-butanol, analogous to the production of acetone by dehydrogenation of gaseous
isopropyl alcohol on copper, zinc, or bronze catalysts at 400 550 C. At 80 95 % sec-butyl
alcohol conversion, MEK selectivity is > 95 %.
In some cases MEK can be produced in the same
facilities as acetone. Butenes (dehydration) and
higher ketones (autocondensation) are byproducts. In 1995, 730 000 t of MEK were produced
worldwide.
2-Butanone is produced by ARCO (US),
AKZO (NL), Biochimica (ES), BP (GB), Carbochlor (Argent.), Celanese (US, CA, Mexico),
Esso (GB, US), Maruzen (JP), PCUK (FR),
Shell (FR, NL, US, CA), Texaco (FRG), Tonen
(JP), UCC (US), Sasol (ZA). Interest in MEK as
a solvent for paints and adhesives has been growing since the 1980s. In general, MEK is considered to be a competitor for ethyl acetate, especially as a low-boiling solvent. It has broad application as a solvent for nitrocellulose, cellulose
acetate butyrate, ethylcellulose, acrylic resins,
vinylacetates, and vinylchloride vinylacetate
copolymer (based on synthetic surface-coating
preparation). It is favored as a lacquer solvent
because of its low viscosity, high solids concentration, and great diluent tolerance.
c 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

10.1002/14356007.a04 475

4.3. Direct Oxidation of

n-Butenes (Hoechst-Wacker Process)
5.
Quality, Storage, Transportation . . .
6.
Uses . . . . . . . . . . . . . . . . . . . . . .
7.
Economic Aspects . . . . . . . . . . . . .
8.
Toxicology . . . . . . . . . . . . . . . . . .
9.
References . . . . . . . . . . . . . . . . . .

4
5
5
6
6
7

Moreover, MEK can be used as an activator

for oxidative reactions, as a selective extractant,
as a special solvent for dewaxing mineral oil
fractions, and as a chemical intermediate. (see
Table 1).
Table 1. Physical data of 2-butanone [9], [10]
Mr
mp, C
bp, C
Relative density,
d 20
4
d 20
20
Refractive index, n20
D
Evaporation number (ether=1)
Critical temperature, C
Critical pressure, MPa
Critical density, , g/L
Dynamic viscosity at 20 C, mPa s
Surface tension at 20 C, mN/m
Molar heat cp at 23.8 C, J mol1 K1
Heat of fusion, J/mol
Heat of vaporization at 79.6 C, J/mol
Combustion enthalpy at constant
pressure, 25 C, kJ/mol
Thermal conductivity, W m1 K1
at 0 C
20 C
50 C
Solubility at 20 C
2-butanone in water, mass fraction, %
water in 2-butanone, mass fraction, %
Flash point (DIN 51755), C
Explosion limits in air at 20 C, 101.3 KPa,
lower, volume fraction, %
upper, volume fraction, %
Ignition temperature, C
Ignition class (VED)
Explosion class (VED)
Electric conductivity at 20 C, Ohm1 cm1
Dipole moment, Debye
Dielectric constant of the liquid at 20 C

72.11
86.9
79.6
0.8045
0.80615
1.3788
2.6
262.45
4.15
0.270
0.323
24.6
160.8
7456
31.2
2444.3
0.150
0.145
0.137
27.5
12.5
1
1.8
11.5
505
G1
1
5108
3.18
15.45

2-Butanone, methyl ethyl ketone, MEK,

CH3 COCH2 CH3 , is a relatively mobile, colorless liquid. Its typical odor resembles that of
acetone. The compound is only partially watermiscible, whereas it is completely miscible with
most organic solvents. 2-Butanone forms binary
and ternary azeotropic mixtures in combination
with water and several other organic solvents
(see Table 2).
Table 2. Binary azeotropic mixtures containing MEK [11]
Second component

Mass
fraction
of MEK

bp at
1013 hPa,

Water
Benzene
n-Hexane
n-Heptane
Cyclohexane
1,3-Cyclohexadiene
Methanol
Ethanol
Isopropyl alcohol
tert-Butyl alcohol
Ethyl acetate
Methyl propionate
Propyl formate
Chloroform
Carbon tetrachloride
Carbon disulde
Propyl mercaptan
Thiophene
Ethyl sulde

88.7
37.5
29.5
73.0
40
40
30.0
60.9
68.0
73
18.0
52
55
96.0
71.0
15.3
75
55.0
20

73.4
78.4
64.3
77.0
72
73
63.5
74.0
77.5
77.5
77.0
79.25
79.45
79.65
73.8
45.85
55.5
76.0
77.5

2-Butanone does not form a binary azeotropic

mixture with toluene, m-xylene, n-butanol,
isobutanol, sec-butyl alcohol, 4-methyl-2pentanol, allyl alcohol, acetic acid methyl ester, acetic acid isopropyl ester, acetic acid nbutyl ester, acetic acid isobutyl ester, 1,1-dichloroethane, isobutyl chloride, propyl bromide, ethyl iodide, trichloroethylene, dichlorobromomethane, isobutyl bromide, formic acid,
and acetic acid.
2-Butanone forms ternary azeotropes with
water/benzene and water/carbon tetrachloride
[11].

3. Chemical Properties
Under normal conditions and in the absence of
atmospheric oxygen MEK is stable. Care must
be taken after prolonged storage because peroxides may form in the presence of oxygen [12].

2-Butanone is unsaponiable and, unlike esters, does not form corrosive products upon hydrolysis. It is heat and light stable. It decomposes only after prolonged UV exposure (yielding ethane, methane, carbon monoxide, ethylene, and diacetyl) [13].
Diacetyl [431-03-8] is formed by oxidation
with airin the presence of special catalysts [14].
Methyl ethyl ketone peroxide [19393-67-0],
a polymerization catalyst, is formed by oxidation with a 30 % solutionof hydrogen peroxide
[15]. Nitric acid and other strong oxidants oxidize MEK to a mixture of formic and propionic
acids [15].
sec-Butyl alcohol [78-92-2] is obtained by
catalytic reduction with hydrogen [15]. It can
also be formed by electrolytic reduction in
sodium acetate solution or by reduction with
ammonium amalgam or lithium aluminum hydride. 3,4-Dimethyl-3,4-hexanediol is obtained
by electrolytic reduction in an acidic medium or
by reduction with magnesium amalgam [15].
Methyl ethyl ketone forms addition products
with hydrogen cyanide as well as with sodium
and potassium hydrogen sultes. 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 intermediatefor further syntheses, is of particular interest. During basecatalyzed autocondensationin the liquid phase
and during gase-phase condensation on alkalinized copper catalysts, the carbonyl group reacts
with the methyl group, whereas during acidcatalyzed condensation the methylene group in
-position to the carbonyl group is attacked [16].

Methyl ethyl ketone and citral [5392-40-5]

condense toform methylpseudoionone that can
be cyclized to methylionone, a compound used
for producing synthetic violet perfume.
During condensation with low-molecular
aldehydes (during base-catalyzed and acidcatalyzed aldolization) the -position of the carbonyl group is rst occupied [17], [18].

2-Butanone

4. Production

Thus, the base-catalyzed aldolization with

less than amounts of formaldehyde yields 2methyl butane-1-ol-3-one [17] and exhaustive
hydroxymethylation, with reduction of the carbonyl group (crossed Cannizzaro reaction), produces desoxyanhydroeneaheptite [19].

When MEK is reacted with primary and secondary 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 -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 ethylketoxime, an antiskinning agent, is formed.
Condensation of MEK with aliphatic esters
and anhydrides gives -diketones.
Phenols react with MEK to form oxyphenylene compounds. In combination with phenol,
2,2-hydroxyphenyl butane is obtained, a homolog of hydroxyphenyl propane (Bisphenol A
[80-05-7] ), an important materialfor the production of synthetic resins.
Methyl ethyl ketone can be halogenated in
the -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 Reformatzky reaction produces the -oxyester from
monobromine-substituted esters [20].

Most MEK (88 %) is produced today by dehydrogenation of sec-butyl alcohol (SBA). SBA
can easily be produced by hydration of n-butenes
(from petrochemically produced C4 rafnates)
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 (HoechstWacker process, Maruzen process, [23], [24] )
has not been generally accepted, because of undesired byproducts.
The sec-butylbenzenehydroperoxide route
giving phenol and MEK by acid-catalyzed splitting [25] is uneconomical. The autoxidation of
liquid sec-butyl alcohol, giving MEK and hydrogen peroxide [26], and the catalytic oxidative hydration of gaseous n-butenes [27] are also uneconomical. The oxidation of n-butenes with ethylbenzenehydroperoxide to form butylene oxides,
and subsequent hydration and formation of ketones 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 endothermic 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 dehydrogenation. The latter two require high dehydrogenation temperatures (400 C). Dehydration of SBA
to butenes takes place as a side reaction on

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 dehydrogenation 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 contamination with water, butene oligomers, and di-secbutyl ether [37].
Deutsche Texaco developed a process in
which practically anhydrous sec-butyl alcohol has been produced since 1983 by direct 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 reactivation becomes necessary (3 4 months) render
the process economically attractive. (see Figure 1).

Table 3 lists further processes for the production 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. Autoxidation of n-butane takes place in liquid phase according to a radical mechanism yielding MEK as
an intermediate and acetic acid as the end product. The continuous plug ow 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 ow 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 homogeneously 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)

Figure 1. Gaseous-phase dehydrogenation of sec-butyl alcohol (Deutsche Texaco AG process)

a) Reactor; b) Oil circulation heating; c) Condenser; d) Separator; 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 puried 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 addition, the dehydration to butenes on copper catalysts is for the most part prevented.
During reaction and subsequent treatment,
practically no waste disposal problems arise.

In the direct oxidation of n-butenes according

to the Hoechst-Wacker process, oxygen is transferred 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 following reaction products (conversions of up to 95 %

are attained):
Reaction products:
MEK
n-Butyraldehyde
Chlorinated products
Carbon dioxide

Selectivities, mol %
86
4
6
1

The main disadvantages are: formation of

chlorinated butanones and n-butyraldehyde and
corrosion caused by free acids.

2-Butanone

Table 3. Further processes for producing methyl ethyl ketone by gase-phase dehydrogenation of sec-butyl alcohol
Company

Catalyst

Standard Oil
Esso Research & Eng.
Maruzen Oil
Knapsack Griesheim
Toyo Rayon
Ruhrchemie

ZnO/Bi2 O3
ZnO/Na2 CO3 /Al2 O3
bronze
CuO/CrO
CuO/NaF/SiO2
60 % Cu, Cr2 O3 ,
MgO, 12 % SiO2 ,
10 % H2 O
22 % Cu,
8 % BaCrO4 ,
2 % Cr2 O3 ,
0.5 % Na2 O,
61 % SiO2
0.05 % Pt/Al2 O3
5 % Cu, 5 % Cr/Al2 O3

Veba-Chemie

Shell-Chemie
Shell-Chemie
a
b
c

H2 O
content,
vol %
0
0
0
0

Temperature,

Pressure,

400
413
390
270 320
300
260

0.1 0.3

90.4

180

0
0

358
286

MPa

0.3

0.6
0.6

Conversion,
%

96 97
80
88 93
96
90

Selectivity,
mol %

97
99
93 96
100
100

Yield,
mol %
80
93 94
79.2

Reference

90

[38]
[39]
[33]
[40]
[41]
[35]

57.3 a

63 b

97.8 c

[36]

92.5 93.5
81 85

96.3
86 92

90
73 77

[37]
[37]

Relative to sec-butyl alcohol.

Relative to di-sec -butyl ether.
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 Consortium fur Elektrochemie [48] and Eastman Kodak
[49]. For further processes, see [5053].

5. Quality, Storage, Transportation

It is possible to produce high-purity MEK
(DIN 53247, ASTM D 740, BS 1940).
The present sales specications of Deutsche
Texaco AG are listed in Table 4.
Table 4. Sales specications for MEK
Purity, wt %
d 20
4
d 20
20
Boiling range, C
Acidity
(as acetic acid), mg KOH/g
Water content, wt %,
Color (Pt Co, APHA),
Nonvolatile matter, wt %

GC
(DIN 51757)
DIN 51751
ASTM D 1078

min. 99.7
0.804 0.806
0.805 0.807
within 0.5
incl. 79.6
0.0001

DIN 51777
ASTM D 1364
ASTM D 1209

max. 0.1
max. 10
max. 0.002

A stable dilute potassium permanganate solution indicates high purity (permanganate time
according to ASTM D 1363).
Storage life of MEK is limited. Carbon steel
containers (ST 3529) are suitable for shortterm storage and transportation. Stainless steel

(316 SS) or containers with a tin lining are recommended for long-term storage. Once autocatalysis has started, it continues even if storage
is continued in inert containers. During longterm storage the formation of peroxide must
be prevented. Since MEK is somewhat hygroscopic, 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; European Council, Yellow Book 78/79: no. 606002-00-3; European Communities: Guideline/D
VgAst, no. 606-002-00-3; UK: Blue Book,
Fla.L. IMDG-Code E 3080; USA: CFR 49,
172.101, Fla.L.; IATA RAR: art. no. 726 Fla.L.

6. Uses
MEK is an important solvent with properties
similar to those of acetone. MEK has the following advantages in comparison to other solvents with comparable rates of evaporation: very
high power of dissolution, high ratio of dissolved
matter to viscosity, miscibility with a large number of hydrocarbons without impairing the solids
content or viscosity, favorable volume/mass ratio due to its low density.

2-Butanone

The following natural substances, plastics, and resins can be dissolved in MEK:
rosin, ester resins, pentaerythritol ester resins,
Congo ester, dammar (dewaxed), nitrocellulose, low-molecular cellulose acetate, cellulose
acetobutyrate, cellulose acetostearate, methylcellulose, epoxy resins, nearly all alkyd and
phenolic resins, polyvinylacetate, vinylchloride/acetate mixed polymerizates, vinylchloride/vinylidene chloride mixed polymerizates, coumarone indene resins, sulfonamide
resins, cyclohexanone resins, acrylic resins,
polystyrene, chlorinated rubber, polyurethane.
Cellulose
triacetate,
high-molecular
cellulose
acetate,
poly(vinylchloride),
poly(vinylbutyral), polysulde rubber cannot
be dissolved in MEK. Shellac is only partially
soluble.
Other areas of application are production
of synthetic leather, transparent paper, printing 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 despite the great number of possible reaction; however, condensation with formaldehyde to obtain methyl isopropenyl ketone, autocondensation to form ethyl amyl ketone, and mixed condensation 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 peroxide is used as a polymerization initiator for unsaturated polyesters. Diacetyl serves as a butter avorer. 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 Federal Republic of Germany (by decree of Bundesmonopolverwaltung in Offenbach).

7. Economic Aspects
Table 5 shows the 1979 sales (in %) for the various markets in the Federal Republic of Germany.
The worldwide consumption of MEK in
1979 amounted to 642000 t (Western Europe 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
Coating and printing of plastics
Chemical industry (incl. sound carrier),
pharmaceutical industry
Adhesives
Miscellaneous

40
20
13
11
16

MEK is also available under the following

names:
German: Ethylmethylketon, Acetonersatz, Ketobutan, 2-Butanon
English: Butanone, 2-butanone, MEK, methylacetone, meetco
French: Methylethylcetone,
butane-2-one,
ethylmethylcetone, 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]. Sensitive persons may develop dermatoses [57].
Liquid MEK temporarily irritates the eye and
corneas [56].
MEK is usually absorbed through the respiratory 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. However, unlike 2-hexanone and n-hexane, which
are further oxidized to form neurotoxic 2,5hexanedione after oxidation of the -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 simultaneous administration of MEK [59], [60].
The chronic inhalation of 200 ppm (MAK, TLV)
does not seem to be harmful [61].

2-Butanone
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 sh:
5600 mg/L. Maximum permissible concentrations 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-Kuchler: Organische
Technologie II, vol. 6, Hanser Verlag,
Munchen 1982, pp. 77, 81.
5. Rompps Chemie Lexikon, 8th ed., vol. 1,
p. 541.
6. G. Hommel: Handbuch der gefahrlichen
Guter, Springer Verlag, Berlin 1980.
7. Kirk-Othmer, 3rd ed., vol. 13, p. 894.
8. Ullmann, 4th ed., vol. 14, p. 193 ff.
Specic References
9. VDI-Warmeatlas 1983, VDI-Verlag
Dusseldorf.
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.

16. A. T. Nielsen, Organic Reactions, vol. 16, J.

Wiley & Sons, New York 1968, p. 20.
17. Rheinpreuen AG, CA 605368, 1955 (W.
Grimme, J. Wollner).
18. Rheinpreuen AG, DE 1198814, 1963 (J.
Wollner, 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. Erdol 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. Rheinpreuen 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,
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44. Consortium f. Elektrochemie, GB 878777,
1961.
45. J. Smidt et al., Erdol Kohle Erdgas Petrochem.
16 (1963) 560.
46. Maruzen Oil, JP 46-2010, 1971.

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.
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15 (1936) no. 6, 205.
56. H. F. Smyth Jr., Am. Ind. Hyg. Ass. Q. 17
(1956) 129.

57. G. D. Clayton, F. E. Clayton (eds.): Pattys

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1,4-Butenediol Butanediols, Butenediol, and Butynediol

Butene Polymers Polyolens