Article No : a22_163

Propanediols
CARL J. SULLIVAN, ARCO Chemical Company, Newtown Square, Pennsylvania 19073,
United States

1. 1,2- Propanediol and Higher Propylene 1.8. Derivatives . . . . . . ..... ..... .... ..... . 238
Glycols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 233 2. 1,3- Propanediol . . ..... ..... .... ..... . 238
1.1. Physical Properties . . . . . . . . . . . . . . . . . . . 233 2.1. Properties . . . . . . ..... ..... .... ..... . 238
1.2. Chemical Properties . . . . . . . . . . . . . . . . . . 235 2.2. Production . . . . . . ..... ..... .... ..... . 239
1.3. Production . . . . . . . . . . . . . . . . . . . . . . . . . . 236 2.3. Uses . . . . . . . . . . . ..... ..... .... ..... . 239
1.4. Quality Specifications. . . . . . . . . . . . . . . . . . 236 3. Toxicology . . . . . . ..... ..... .... ..... . 239
1.5. Transportation and Storage. . . . . . . . . . . . . 237 References . . . . . . ..... ..... .... ..... . 240
1.6. Economic Aspects . . . . . . . . . . . . . . . . . . . . 237
1.7. Uses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 237

1. 1,2- Propanediol and Higher A growing application is in the field of

Propylene Glycols
1,2-Propanediol, [57-55-6], propylene glycol,
HOCH2CH(CH3)OH, is very similar to ethylene
glycol in its physical and chemical properties
(! Ethylene Glycol). The first reported
description of propylene glycol was by WURTZ
in 1859 [1].
Industrial-scale synthesis of propylene glycol
from propylene oxide (! Propylene Oxide) and
water began in the 1930s. Current production
uses this same process, which leads simulta-
neously to di- and tripropylene glycols. The
worldwide capacity for propylene glycol is esti-
mated to be 9
105 t (1990) [2]. Production may
be lower because some propylene glycol produc-
tion units are designed to permit switching to
ethylene glycol output depending upon relative
demand for the glycols.
Propylene glycol is used in many diverse
applications such as unsaturated polyesters
(! Polyester Resins, Unsaturated) for thermo-
set composites, food chemistry, food processing
equipment, cosmetics, and pharmaceuticals.
deicers and automotive antifreeze components
(! Antifreezes).
1.1. Physical Properties
Propylene glycol is a clear, colorless, strongly
hygroscopic liquid. The higher propylene glycols
(di- and tripropylene glycol) have similar prop-
erties. Dipropylene glycol [110-98-5] exists as
three isomers differing in the positions of the
methyl substituents, and tripropylene glycol
[24800-44-0] is typically a mixture of several
isomers. All three glycols are moderately viscous
liquids that do not readily crystallize, but solidify
to vitreous masses upon cooling. Fundamental
physical properties of these diols are listed in
Table 1 [3–9].
Propylene glycol is readily miscible with
water and other polar solvents (e.g., alcohols and
acetone). Propylene glycols are good solvents for
many polar organic substances, such as phenols,
alcohols, dyes, natural products, and some resins.
Propylene glycol is insoluble to sparingly soluble

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

DOI: 10.1002/14356007.a22_163
234 Propanediols Vol. 30

Table 1. Physical properties of propylene glycols

Property Propylene glycol Dipropylene glycol* Tripropylene glycol*

Mr 76.10 134.18 196.26

bp,  C 187.9 232.8 271
mp,  C <60 <40 <30
d20
20 1.036 1.023 1.019
Refractive index n20
D 1.4328 1.4415 1.4449
Vapor pressure (20  C), kPa 0.011 <0.001 <0.001
Heat of vaporization at bp, kJ/kg 711 400 330
Specific heat capacity (20  C), kJ kg1 K1 2.49 2.36 2.26
Electrical conductivity (20  C), mSm 4.4 0.19
Cubic coefficient of expansion (20  C), K1 7.2
104 7.4
104 7.7
104
Heat conductivity (20  C), Wm1 K1 0.20 0.16 0.11
Dynamic viscosity (20  C), mPa  s 56 107 84
Surface tension (20  C), mNm 38 35 35
Dielectric constant (20  C) 28 21 14
Flash point (DIN 51 758),  C 103 120 149
Ignition temperature (DIN 51 794),  C 410 350 260
Lower explosion limit in air, vol % 2.6 1.26 1.3
*
Physical properties may be affected by isomer ratios.

in such nonpolar solvents as petroleum ethers,
benzene, aromatic hydrocarbons, and carbon
tetrachloride.
Propylene glycol greatly reduces the freezing
point of water and is therefore being developed
as an alternative to ethylene glycol in automo-
tive antifreeze systems [10, 11] and aircraft
deicers [12, 13]. The solidification temperatures
of propylene glycol and its higher homologues
at varying water ratios are plotted in Figure 1.
The viscosities and densities of aqueous pro-
pylene glycol solutions are plotted in Figures 2
and 3 [4].
Vapor pressure versus temperature curves
for the three propylene glycol homologues are
plotted in Figure 4. Propylene glycol forms
azeotropes with the solvents listed in Table 2
[14].

Figure 1. Solidification temperatures for aqueous propylene

glycols Figure 2. Viscosity of aqueous propylene glycols
a) Tripropylene glycol; b) Dipropylene glycol; c) Propylene a) Tripropylene glycol; b) Dipropylene glycol; c) Propylene
glycol glycol
Vol. 30 Propanediols 235
Table 2. Azeotropes with propylene glycol [14]

Cosolvent Cosolvent Azeotrope Propylene

bp,  C bp,  C glycol, wt %

o-Nitrophenol 217 186 >62

Aniline 184 179.5 43
Toluene 110.6 110.5 1.5
o-Xylene 144.4 135.8 10
Dodecane 216 175 67
N,N-Dimethyl-
p-toluidine 185.3 174 37
Dibutyl ether 142 136
Tetradecane 252 179 70
Methyl hexyl ketone 173 <170
N-Methylaniline 196 <181 >46
N,N-Dimethylaniline 194 <177 >45
Propylene glycol 187.9

Figure 3. Density of aqueous propylene glycols at 20  C

a) Tripropylene glycol; b) Dipropylene glycol; c) Propylene Predominant among such applications is the
glycol
reaction with maleic anhydride and other
diacid components to yield unsaturated polye-
sters [15, 16]:
1.2. Chemical Properties

The chemical properties of propylene glycol

are determined predominantly by its hydroxyl
groups, and its reactions are typical of alcohols
(! Alcohols, Aliphatic). Propylene glycol
condenses with carboxylic acids at elevated
temperature to yield esters and water. It also
reacts readily with isocyanates and acid Propylene glycol reacts with propylene oxide
chlorides to yield carbamates and esters, to form dipropylene glycol, tripropylene glycol,
respectively. and polyether polyols. The resulting polypro-
Propylene glycol undergoes polycondensa- pylene glycol ethers are important industrial
tion reactions with diacids to yield polyesters. building blocks for polyurethane foams and
elastomers (! Polyurethanes) [17, 18].

Because of its 1,2-diol structure, propylene

Figure 4. Vapor pressure versus temperature for propylene
glycols
glycol also undergoes a variety of interesting
cyclization reactions. Cyclic acetals and ketals
are formed with aldehydes and ketones, respec-
tively [19].
At elevated temperature in the presence of an
acidic catalyst, propylene glycol can undergo
dehydration to yield cyclic ethers. Very low
levels of these dehydration products are common
236 Propanediols
in aqueous byproduct streams of polycondensa-
tion reactions involving propylene glycol [20].
Propylene glycol is unusual in that the com-
mercial product is a racemic mixture of two
chiral isomers. Only small quantities of chiral
material are available from specialty chemical
distributors.
1.3. Production
The only industrial process for manufacturing
propylene glycol is direct hydrolysis of propyl-
ene oxide with water. Dipropylene glycol and
tripropylene glycol are formed by sequential
addition of propylene oxide to propylene glycol.
Consequently, all three products are produced
simultaneously and separated by distillation.
Propylene oxide and water are combined in
the initial stage of the process at a molar ratio of
1 : 15 at an initial temperature of 125  C and a
pressure of approximately 2 MPa (Fig. 5). Due
to the exothermic reaction [21], the reactor efflu-
ent temperature will typically rise to 190  C. At
the above ratio of water to oxide, the resulting
propylene glycol – dipropylene glycol – tripro-
pylene glycol mixture is approximately in the
ratio of 100 : 10 : 1. Higher propylene glycol
ratios are attained by increasing the water-to-
oxide ratio; however, such an increase also in-
creases recycle rates, lowers throughput, and
raises energy costs.
Figure 5. Schematic of propylene glycol production
a) Reactor; b) Evaporator (typically 2 – 4 columns; c) Propylene glycol distillation column; d) Dipropylene glycol distillation
column; e) Tripropylene glycol distillation column
Vol. 30
The water – glycol mixture exits the reactor
zone (a) at about 200  C and is stripped of water
in dehydration columns (b). Three successive
vacuum distillations (c – e) separate high-purity
propylene glycol, dipropylene glycol, and tripro-
pylene glycol. The residue represents a mixture
of higher glycols, which have some limited com-
mercial use. Waste from this process is extraor-
dinarily low. Because of the very low toxicity of
propylene glycol, dipropylene glycol, and tripro-
pylene glycol, these materials represent a mini-
mal hazard to the environment. All are readily
biodegradable.
Alternative Routes to propylene glycol have
been investigated. Acetoxidation of propene to
yield glycol acetates followed by hydrolysis to
the glycol has been reviewed [22]. This technique
involves lower production costs than the propyl-
ene oxide route, but fixed capital investment
costs are much higher. Direct hydroxylation of
propene to propylene glycol using oxygen in the
presence of osmium catalysts has been reported
[23–25]. However, because of the ready avail-
ability of propylene oxide, the simplicity of the
current process, and the extremely low level of
waste generated by the propylene oxide route, no
alternative process has yet been commercialized.
1.4. Quality Specifications
At least two commercial grades of monopropy-
lene glycol exist – a high-purity industrial
grade, and a higher-purity grade called ‘‘super
pure’’ or ‘‘U.S.P.’’ grade. Typical assays for the
Vol. 30 Propanediols 237

Table 3. Typical properties of commercial propylene glycol [4, 26] can also be used to produce ethylene glycol
Property Industrial U.S.P.
depending upon market pressures. Actual pro-
grade grade duction in the United States in 1989 is estimated
to have been 3.65
105 t, approximately 95 % of
Purity, % 99.5 99.5
20
d20 1.0377 1.035 – 1.037
capacity [27].
Distillation initial bp,  C 185 185
dry point,  C 190 189
Acidity, wt % as acetic acid 0.005 0.002 1.7. Uses
Chlorides, ppm as Cl (max.) 10.0 1.0
Iron, ppm (max.) 1.0 0.5
Heavy metals, ppma 5.0 Propylene Glycol. The single largest use of
Arsenic, ppm as As (max.) 3.0 propylene glycol is in the manufacture of unsat-
Sulfate, wt % (max.) 0.006 urated polyester resins. It is reacted with saturat-
Water, wt % (max.) 0.2
ed and unsaturated carboxylic diacids such as
a
All metal residues are calculated as if they were lead. isophthalic acid and maleic anhydride. The
resulting resins are dissolved in styrene or an-
two grades of propylene glycol are the same; other polymerizable monomer, then combined
however, the U.S.P. grade is used in applica- with filler, chopped glass, a peroxide polymeri-
tions such as pharmaceuticals, cosmetics, and zation initiator, and other additives, and cured to
food additives, and entails higher quality yield a hard, cross-linked, thermoset composite
standards (see Table 3) [4]. [15, 16, 21]. The end-use applications for such
products include automotive plastics, fiberglass
boats, and construction. Roughly 45 % of the
1.5. Transportation and Storage propylene glycol produced goes to this one broad
application [5].
Propylene glycol, dipropylene glycol, and tripro- Propylene glycol has many diverse applica-
pylene glycol are stable materials that require no tions in the food and pharmaceutical industries
special handling procedures. They are noncorro- because of the ‘‘Generally Regarded As Safe’’
sive and can be transported or stored in stainless (GRAS) status conferred on it by the FDA in the
steel, aluminum, and lined steel containers. United States. Propylene glycol is used as a
Carbon steel is also acceptable, although slight humectant, solvent, and preservative in food and
iron contamination may occur upon extended pet food products. In the manufacture of food
periods of storage. U.S.P.-grade propylene gly- products, propylene glycol is used as a lubricant
col is typically stored in stainless steel. The for machinery, as a solvent in food processing, in
glycols are hygroscopic, and should be protected food wraps, and as an antifreeze agent in
from unnecessary exposure to the atmosphere. machinery cooling water. Propylene glycol is
also used as an emollient, softening agent, and
humectant in skin- care products and cosmetics,
1.6. Economic Aspects and as a carrier for livestock medicinal products
[4, 7].
Worldwide capacity for propylene glycol pro- Propylene glycol is utilized in aircraft deicing
duction is summarized in Table 4. These capaci- and anti-icing fluids because of its proven per-
ty figures are flexible, because the same facilities formance, low toxicity, ready biodegradability,
and environmental acceptance [13]. It offers
freeze protection similar to that of ethylene
Table 4. Worldwide capacity for propylene glycol production in glycol, the principle component of automotive
1990 [2]
antifreeze solutions. Automotive antifreeze
Region Number of Capacity, compositions incorporating propylene glycol
manufacturers 103 t/a have been investigated [10, 11, 28].
North America 5 384 Propylene glycol is useful as a lubricant in
Western Europe 6 361 combination with di- and tripropylene glycols. It
East Asia 7 118 is commonly employed as a humectant for to-
Total 18 863
bacco. Propylene glycol is also introduced into
238 Propanediols Vol. 30

many latex paints as a freeze – thaw protector, in coatings and cleaners.

and to provide evaporation control in hot and dry
environments. Propylene glycol is reacted with
fatty acids or long- chain carboxylic acids to
produce ester lubricants, emulsifiers, and plasti-
cizers [29–31].
Propylene glycol is a precursor of many poly-
ether polyols used in the urethane foam, elasto-
mer, adhesives, and sealants industry, whereby
the compound is reacted with propylene oxide
and/or ethylene oxide in order to generate a low
molecular mass polyether [17, 18].

Dipropylene and Tripropylene Glycols.

Both glycols are used in hydraulic fluids and
brake fluids because of their high stability and 2. 1,3- Propanediol
low corrosion properties. They are also used in
inks and some paints because of their good 1,3-Propanediol [504-63-2], trimethylene glycol,
solvency for pigments and binders, very low HOCH2CH2CH2OH, is produced on a much
evaporation rates, and low toxicity. Stamp pad smaller scale than its isomer, propylene glycol.
inks are a prime example [32]. Dipropylene In spite of some interesting areas of application,
glycol has some application in refining opera- total production remains relatively small. The
tions because it facilitates the separation of difficulties of manufacturing the product result in
aromatic and aliphatic hydrocarbons. Di- and a poorly competitive price structure relative to
tripropylene glycols are precursors of low other diols.
molecular mass esters and polyesters, which have
utility as plasticizers and lubricants. Both glycols
are also used to make polyester polyols for 2.1. Properties
urethane applications.
Key physical properties of 1,3-propanediol are as
follows [3, 34]:
1.8. Derivatives
Mr 76.10
mp 27  C
The major end-use derivatives of propylene
bp (101.3 kPa) 214  C
glycol, dipropylene glycol, and tripropylene bp (0.7 kPa) 94  C
glycol are unsaturated polyester resins as well Vapor pressure (20  C) 0.008 kPa
as low molecular mass ester and polyester Vapor pressure (100  C) 0.98 kPa
20
d20 1.0554
plasticizers. Propylene glycol-initiated poly-
d420 1.0529
ethers are also modest-volume commodity Refractive index n20
D 1.4389
products. Kinematic viscosity 46 m2/s
The class of materials known as glycol ethers Flash point 80  C
(propylene glycol alkyl ethers) is commonly
referred to as propylene glycol derivatives, but 1,3-Propanediol is a clear, colorless, odorless
most of these are actually propylene oxide- liquid that is miscible with water, alcohols,
derived products because of the ease with which ethers, and formamide. It is sparingly soluble in
they can be prepared from the oxide. Neverthe- benzene and chloroform.
less, some glycol ether products actually are The chemical properties of 1,3-propanediol
derived from the glycol – most notably propylene are typical of alcohols. Like 1,2-propanediol,
glycol mono-tert-butyl ether, which is produced 1,3-propanediol condenses with carboxylic acids
by reacting propylene glycol with isobutene [33]. at elevated temperature to yield esters. It also
These derivatives find application predominantly reacts with isocyanates and acid chlorides to
Vol. 30
yield urethanes and esters, respectively. Unlike
1,2-propanediol, 1,3-propanediol has two prima-
ry hydroxyl groups with equivalent reactivity.
1,3-Propanediol readily forms ethers. 3,30 -
Dihydroxydipropyl ether forms upon continued
reflux of the diol. 1,3-Propanediol reacts with
aldehydes and ketones, often in the presence of
acidic catalysts, to form 1,3-dioxanes [35, 36]:
Over aluminum oxide at temperatures above
250  C, 1,3-propanediol decomposes to allyl
alcohol, propanol, and other products.
1,3-Propanediol reacts with diacids to form
polyesters. The polyester with terephthalic acid
is reported to have a crystalline melting point of
220  C [37]. Polyurethanes can also be synthe-
sized from 1,3-propanediol.
2.2. Production
1,3-Propanediol is prepared by a two-step pro-
cess involving the hydrolysis of acrolein to 3-
hydroxypropanal followed by hydrogenation [3,
38]:
Hydrolysis is carried out under weakly acidic
conditions in water containing initially ca. 20 %
acrolein. Higher concentrations of acrolein tend
to lead to greater amounts of undesired bypro-
ducts as a result of reaction between acrolein and
hydroxypropanal.
3-Hydroxypropanal can be hydrogenated in
the aqueous phase directly; however, the pre-
ferred technique is to extract the aldehyde into an
organic solvent – particularly 2-methylpropa-
nol – and then hydrogenate the aldehyde to
yield the diol. Hydrogenation is conducted with
Raney nickel under pressure in the aqueous phase
and with nickel-supported catalysts at 2 – 4 MPa
Propanediols 239
and 110 – 150  C in the organic phase [39]. The
diol is subsequently separated from solvent and
water by distillation.
The yield of desired product by this route is
relatively low – approximately 45 %. Alterna-
tive techniques for synthesizing the diol have
appeared in the patent literature. Hydroformyla-
tion of ethylene oxide followed by hydrogenation
yields 1,3-propanediol in good yield (92 %), but a
high catalyst concentration and a very large ex-
cess of solvent render the process uneconomical
[40]. More recently, hydroformylation of ethyl-
ene oxide directly to 1,3-propanediol with a rho-
dium – phosphine catalyst system has been dis-
closed [41]. The reaction of ethylene with form-
aldehyde and carboxylic acids has also not been
commericialized because of low selectivity [42].
Handling of 1,3-propanediol is similar to that
of propylene glycol. The material is noncorrosive
and can be transported in stainless steel, alumi-
num, or lined steel vessels.
Quality analysis is readily accomplished by gas
chromatography. A good technical grade generally
displays a purity between 98.5 and 99.5 %.
The environmental impact of this product is
expected to be low because of its low toxicity and
ready biodegradability. The handling of acrolein
in the production process must be carefully
controlled.
2.3. Uses
As a diol, 1,3-propanediol is subject to many of
the same polymeric applications as other low
molecular mass diols (e.g., ethylene glycol, pro-
pylene glycol, and 1,4-butanediol). However, its
relatively high price limits its use to applications
requiring very specific performance characteris-
tics. It is a raw-material source for 1,3-dioxanes.
1,3-Propanediol-bis(4-aminobenzoate) [57609-
64-0] can be used as a chain extender in polyure-
thane elastomers. This bisbenzoate, which can
also be synthesized from 1,3-dichloro-propane,
finds other applications as a cross-linking agent
in epoxy formulations and as a rubber additive.
3. Toxicology
1,2-Propanediol. The toxicological proper-
ties of 1,2-propanediol have been reviewed [3, 4,
240 Propanediols
43]. The substance has such a low order of acute
toxicity that it is considered practically nontoxic.
Since 1942 it has been classified as an acceptable
ingredient in pharmaceutical applications, and
the United States FDA permits its use in food
products and cosmetics. Official requirements
for 1,2-propanediol used as an adjuvant in phar-
maceuticals can be found in international and
national pharmacopeias.
Acute oral LD50 values for rats range from
21.0 to 33.7 g/kg. For mice the values range
from 23.9 to 31.8 g/kg. Tests with other animals
(guinea pig, rabbit, mouse, and dog) yield LD50
values within the same range [43]. These values
correspond to ingestion of 1.5 – 2.0 L by a
typical adult human.
Administration of single, almost lethal doses
to laboratory animals have caused balance dis-
orders resulting from central nervous system
depression. Significant impairment of motion was
observed in rats after oral administration of
19.5 g/kg. A similar level of impairment was
observed with an ethanol dosage of only 1.5 g/kg.
Propylene glycol is not injurious to the eye of
rabbits, and it is not known to have caused any
eye injuries in humans. Slight transitory stinging
and tear formation may result from direct contact
with the eye.
Propylene glycol does not produce any sig-
nificant irritation effects in skin contact with
rabbits or humans, although skin irritation has
been reported in some individuals when high
concentrations were held in contact with skin
under closed conditions [44, 45].
Subchronic and chronic studies also indicate
that propylene glycol has a low order of toxicity.
A two-year study on rats demonstrated that in-
corporation of 5 % propylene glycol into the diet
did not increase or accelerate mortality. No tissue
damage was noted at 7.5 % of the diet for 20
weeks, but at 20 % of the diet the rats exhibited
nonspecific minor changes in liver and kidney
cell structure [46].
Studies also indicate that propylene glycol
does not present a health risk after inhalation.
Monkeys and rats exposed to propylene-glycol-
saturated atmospheres for 12 – 18 months
showed no adverse effects [47].
In vivo and in vitro mutagenicity tests show no
mutagenic behavior [48]. Reproductive studies
with mice, rats, hamsters, and rabbits show no
effects upon fetal development, and no terato-
Vol. 30
genic effects. In a reproductive study with rats, a
level of 7.5 % propylene glycol in food showed
no effects over six generations [49].
In the body, propylene glycol is metabolized
mainly to carbon dioxide via pyruvic acid, but it
also enters into carbohydrate metabolism and pro-
motes glycogen formation. At higher dose levels,
some propylene glycol is excreted in the urine.
No permissible exposure levels have been
established, because none appear to be necessary.
Dipropylene Glycol and Tripropylene
Glycol. These two glycols have not been
studied as extensively as propylene glycol, but
both are considered to possess a low order of
toxicity. The oral LD50 values in rats for dipro-
pylene glycol and tripropylene glycol are 15 g/kg
and 12 g/kg, respectively. In a subchronic study
involving 5 wt % dipropylene glycol in drinking
water, rats were not affected. However, at 10 %
some rats died, and there was evidence of liver
and kidney involvement.
Both di- and tripropylene glycol demonstrate
negligible eye and skin irritation. Continuous or
repetitive application of the two glycols provides
no indication that toxic quantities are absorbed
through the skin. Because of low vapor pressures
and low systemic toxicity, inhalation hazards
appear negligible.
1,3-Propanediol. 1,3-Propanediol is mildly
toxic. The oral LD50 for rats is 14 – 15 g/kg,
whereas intraperitoneal LD50 values for rats and
rabbits are 6 – 7 g/kg and 3 g/kg, respectively
[50]. Prolonged administration to chickens in-
hibits growth [51]. Unlike its isomer, propylene
glycol, 1,3-propanediol is not permitted for use in
food or livestock feed products.
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Further Reading
G. Centi, R. A. van Santen (eds.): Catalysis for Renewables,
Wiley-VCH, Weinheim 2007.
G. P. Chiusoli, P. M. Maitlis (eds.): Metal-Catalysis in
Industrial Organic Processes, Royal Society of Chemis-
try, Cambridge, UK 2006.
B. Kamm, P. R. Gruber, M. Kamm (eds.): Biorefineries -
Industrial Processes and Products, Wiley-VCH, Wein-
heim 2006.
A. E. Martin, F. H. Murphy: ‘‘Glycols, Polypropylene Gly-
col’’, Kirk Othmer Encyclopedia of Chemical Technology,
5th edition, John Wiley & Sons, Hoboken, NJ, online DOI:
10.1002/0471238961.1618151613011820.a01.
M. Pagliaro, M. Rossi: The Future of Glycerol, Royal Society
of Chemistry, Cambridge, UK 2008.
H. K. Phlegm: The Role of the Chemist in Automotive Design,
CRC Taylor & Francis, Boca Raton, FL 2009.