Chemical Papers 67 (9) 12181224 (2013)

DOI: 10.2478/s11696-012-0300-x

ORIGINAL PAPER

Continuous dehydrochlorination of 1,3-dichloropropan-2-ol to

epichlorohydrin: process parameters and by-products formation

Anna Krzyzanowska*, Eugeniusz Milchert

Institute of Organic Chemical Technology, West Pomeranian University of Technology,

Pu
laski 10 Street, 70-322 Szczecin, Poland

Received 27 July 2012; Revised 12 October 2012; Accepted 18 October 2012

The influence of pre-reactor and reactor temperatures on the conversion of 1,3-dichloropropan-

2-ol and the selectivity of its transformation to epichlorohydrin in continuous dehydrochlorination
for two modes of the reaction product collection was studied. The dehydrochlorination process and
mechanism of diglycidyl ether formation are described.

c 2012 Institute of Chemistry, Slovak Academy of Sciences

Keywords: dehydrochlorination, 1,3-dichloropropan-2-ol, epichlorohydrin, diglycidyl ether

Introduction in the course of the dehydrochlorination of a water so-

Until recently, synthetic glycerol has been obtained
by the hydrolysis of epichlorohydrin. Currently, a high
glycerol supply from renewable resources results from
the development of the transesterication of fats in
order to produce fatty acid methyl esters used as diesel
fuel (biodiesel) (Ma & Hanna, 1999). The availability
of large amounts of glycerol from renewable resources
has increased suciently to reduce the price to a low
level. This creates the possibility of using glycerol for
the production of chemicals such as epichlorohydrin.
A complex utilisation of glycerol and biodiesel may
eect a reduction in the fuel price.
Epichlorohydrin is used in the manufacture of
epoxy resins (Czub et al., 2002), ion exchange resins
(Ebner et al., 1999), cross-linked starch (Kim et al.,
2002), surfactants (Mohamed & Mohamed, 2010),
plasticisers, softeners, emulsiers, dyes, oil emulsi-
ers (Greenspan & Gall, 1956), greases, adhesives,
medicines, etc. Several methods have been proposed
for the production of epichlorohydrin, although most
epichlorohydrin is still produced from propylene and
chlorine in a multi-step process (Grzywa & Molenda,
2008). The inuence of the technological parameters
lution of dichloropropanols to epichlorohydrin by the
chlorine method is well-known (Milchert et al., 2012).
The reactions which take place during epichlorohydrin
production by the chlorine method are presented in
Fig. 1.
In the rst stage, propylene (I ) reacts with chlorine
to form allyl chloride (II ), which is subsequently sub-
jected to hydrochlorination resulting in the formation
of a mixture of dichloropropanols (1,3-dichloropropan-
2-ol (III ) and 2,3-dichloropropan-1-ol (IV )). A diluted
aqueous solution (35 mass %) of dichloropropanols
was dehydrochlorinated to epichlorohydrin (V ) using
milk of lime (calcium hydroxide, Ca(OH)2 ) (VI ).
This process on a large industrial scale has many
undesirable features, in particular the large consump-
tion of chlorine. As a result of the reaction, a large
amount of waste calcium chloride is generated as well
as chlorinated organic compounds, the disposal of
which is relatively expensive. The disadvantages of
the commercial processes prompted the search for al-
ternative ways of producing V, which are more atom-
ecient, environmentally friendly and cheaper. The
increasing costs of obtaining I from petrochemical
sources also led to accelerating the search for a pro-

*Corresponding author, e-mail: akrzyzanowska@zut.edu.pl

Presented at the 39th International Conference of the Slovak Society of Chemical Engineering, Tatransk Matliare,
2125 May 2012.
 A. Krzyzanowska, E. Milchert/Chemical Papers 67 (9) 12181224 (2013)
Fig. 1. Industrial preparation of epichlorohydrin (V ) from propylene (I ). Reaction conditions: i) chlorine; ii) HOCl; iii) milk of
lime (Ca(OH)2 ) (VI ).
Fig. 2. Preparation of V via glycerol method. Reaction conditions: i) HCl, catalyst; ii) NaOH or Ca(OH)2 .
cess of producing V which would require less expensive
raw materials. One of these routes is based on the con-
version of glycerol to dichlorohydrins (mainly III ) in
the reaction with waste hydrogen chloride, then dehy-
drochlorination of dichloropropanols to V (Bell et al.,
2008; Santacesaria et al., 2010). Because of the high
prices of petroleum, the production of V from glycerol
is an interesting, alternative technology, signicantly
better, economically, than those based on the syn-
thesis from I and chlorine. Additionally, this method
generates much smaller quantities of by-products and,
most importantly, the waste glycerol from renewable
sources of raw materials is used and waste hydrogen
chloride is managed simultaneously.
The process of producing V based on glycerol was
realised industrially for the rst time by the Solvay
Company under the name of Epicerol Technology in
2007 (initial capacity of 10000 tons per year was set up
at an industrial plant in Tavaux, France) and is the
subject of several patents (e.g. Krat et al. (2005),
Gilbeau and Jestin (2009)). This process has been de-
veloped by several other companies. In this process,
the dehydrochlorination of III is carried out with an
aqueous solution of sodium hydroxide (NaOH). This
enables the waste sodium chloride to be used in the
essential diaphragm electrolysis and, thereby, the pro-
duction of NaOH and chlorine. However, this requires
an accurate dosage of NaOH, control of pH and other
process parameters. In the case of lime milk solution,
the dehydrochlorination proceeds slowly and the lower
solubility of VI in water in comparison with NaOH
acts against an excessive increase in alkalinity and,
thereby, against side reactions.
Under the most favourable conditions, the dehy-
drochlorination of pure III from the glycerol method
1219
proceeds with a similar selectivity of transformation to
V (96 %) and the conversion of III (in the range of 95
98 %) as the dehydrochlorination of aqueous solution
of dichloropropanols with the following composition:
0.57 mass % of III, 1.73 mass % of IV, 0.045 mass % of
hydrogen chloride (Milchert et al., 2012), obtained in
the process based on I and chlorine. However, this re-
quires other technological parameters. In a novel pro-
cess, it is necessary to decrease the temperature of the
pre-reactor and reactor by about 2030 C. Moreover,
the rate of dehydrochlorination of III is considerably
higher than that of IV. The reactions involved in the
production of V by the glycerol method are shown in
Fig. 2.
There are no reports in the literature concerning
the process parameters for the production of V from
III and methods of realising the technological process
itself.
The aim of this study was to establish the inu-
ence of pre-reactor and reactor temperatures on the
course of the dehydrochlorination process of III to V.
A mechanism of diglycidyl ether formation, which is
one of the reaction products, as well as methods of its
identication, is also presented.
Experimental
Reagents and analytical methods
The compound used was 1,3-dichloropropan-2-ol
(III ) with a purity of 98 mass % containing 2 mass %
of 2,3-dichloropropan-1-ol (IV ) purchased from Merck
(Darmstadt, Germany). Dehydrochlorination was car-
ried out with a solution of milk of lime (VI ), dissolving
pure Ca(OH)2 in water (96 mass % of Ca(OH)2 and
1220 A. Krzyzanowska, E. Milchert/Chemical Papers 67 (9) 12181224 (2013)
3 mass % of CaCO3 ) (product of Chempur, Piekary
Slaskie, Poland).
Organic compounds in the epichlorohydrin layer of
the distillate were determined quantitatively by gas
chromatography (GC) using octane as the internal
standard. The SRI 8610C (SRI Instrument Corpo-
ration, USA) apparatus was equipped with a ame
ionisation detector (FID) and a capillary column DB-
WAX (30 m 0.25 mm 1.0 m). The following con-
ditions were used for the analyses: injector tempera-
ture: 200 C, detector temperature: 240 C, carrier gas:
He, ow-rate: 4 mL min1 , air-ow: 250 mL min1 ,
hydrogen-ow: 25 mL min1 . The oven temperature
was maintained at 55 C for 2 min, then it was in-
creased to 160 C at a rate of 15 C min1 , held for
3 min, then increased by 25 C min1 to 240 C and
maintained at 240 C for 6 min.
Organic compounds in the water layer and in
the waste water were determined on a Trace GC
Ultra Thermo (Thermo Scientic, USA) appara-
tus. The chromatograph used was equipped with a
FID and a capillary column RTX Resteak 1701 (30
m 0.53 mm 1.0 m). The following condi-
tions were used for the analyses: injector tempera-
ture: 280 C, detector temperature: 300 C, carrier gas:
He, ow-rate: 5 mL min1 , air-ow: 200 mL min1 ,
hydrogen-ow: 35 mL min1 . The oven temperature
was maintained at 40 C for 4 min, then it was in-
creased to 155 C at a rate of 10 C min1 , and main-
tained at 155 C for 1 min.
The concentrations of chlorine in organic and in-
organic compounds were determined by argentomet-
ric methods. A titrator TitroLine Easy module 3
(Schott, Germany) equipped with a combined silver
electrode with a platinum diaphragm 62Pt was used
for the determination. The water content in the or-
ganic layer of the distillate was determined by the
modied coulometric method on KF831 apparatus
(Metrohm, Switzerland).
Apparatus and experimental procedure
The installation scheme for the dehydrochlorina-
tion of III with an aqueous solution of VI is shown in
Fig. 3. The main apparatus comprises the reaction
stripping column (6, height of 760 mm, inside diame-
ter of 36 mm), connected with pre-reactor (5, height
of 253 mm, inside diameter of 36 mm), lled with
Raschig rings (6 mm 8 mm).
An aqueous solution of III was introduced into
reservoir (3), while VI was introduced into reservoir
(4). Reservoir (15) was lled with water. The pressure
was set in the reactionstripping column (6), using a
vacuum pump (10). The temperature in the cold trap
(9) was kept in the range from 5 C to 10 C. Af-
ter stabilisation of the water-ow in the water cooler
(7), the cooling in cryostat (18) was turned on. The
cold trap was cooled to approximately 15 C. After
stabilisation of the temperatures, the vacuum in the
installation was adjusted. Then, after heating the pre-
reactor (5), which is used as a performing mixer of III
and VI, the reactionstripping column (6) and distil-
lation reboiler (12) under the reactionstripping col-
umn were started. After stabilisation of the ow of
water from reservoir (15) by metering pump (1), the
heating steam generator (14) and steam superheater
(13) were turned on. The steam from the superheater
owed through a bubbler into the distillation reboiler.
The temperature of the steam-ow was measured
using thermocouple (16). The temperature of these
elements was adjusted by changing the intensity of
the current owing through the electric heaters in-
stalled on them. The adjustment was carried out using
autotransformers. After setting the steam-ow using
the metering pumps at a stabilised rate, the aque-
ous solutions of VI and III were introduced. At the
same time, the temperatures of pre-reactor (5) and
reactionstripping column (6) were stabilised. On con-
tinuous supply of substrates and steam, after every
15 min the temperature was controlled in pre-reactor
(5), reactionstripping column (6), distillation reboiler
(12), reservoir of waste water (11), steam generator
(14), and steam superheater (13); the pressure was
also controlled in the reaction system. In the course
of distillation, the reboiler temperature and pH were
measured. The concentrations of chloride ions and
chlorine in the organic compounds were determined
hourly by the potentiometric method. At the end of
the reaction, the metering pumps supplying III and
VI were turned o. For about 10 min after the reac-
tants supply was stopped, the steam supply contin-
ued; then the current setting on the heating elements
was zeroed. The pressure in the reaction system was
adjusted to atmospheric pressure. Consumption of III,
solution of VI, and steam was determined by mass
decrement. Similarly, the amount of distillate from
the reactionstripping column (separated into aque-
ous and organic layers) and the amount of waste water
after combining with the solution that remained in the
distillation reboiler were determined. To make a mass
balance of organic compounds, quantitative analysis
of the distillate and waste water was carried out. Us-
ing gas chromatography, concentrations of compounds
IIIV, glycerol (VII ), 3-chloropropane-1,2-diol (VIII ),
2-chloropropane-1,3-diol (IX ), diglycidyl ether (X ),
and glycidol (XI ) were determined. On the basis of
the analysis, the conversion of III and the selectivity
of the transformation to V related to III consumed
were calculated.
Results and discussion
Influence of pre-reactor temperature
The inuence of pre-reactor temperature on III
conversion and V selectivity for various methods of
 A. Krzyzanowska, E. Milchert/Chemical Papers 67 (9) 12181224 (2013) 1221

Fig. 3. Installation scheme for dehydrochlorination of III with a solution of VI: metering pump (1), magnetic stirrer (2), reservoir
of III (3), reservoir of VI (4), pre-reactor (5), reactionstripping column (6), water cooler (7), reservoir of distillate (V and
water) (8), cold trap (9), vacuum pump (10), reservoir of waste water (11), distillation reboiler (12), steam superheater
(13), steam generator (14), reservoir of water (15), temperature gauge (16), pH, temperature gauge (17), cryostat (18).

Table 1. Technological parameters for dehydrochlorination of III eect of pre-reactor temperature on the distillate collected from
top of reactionstripping column

Ca(OH)2 /III mole ratio

Parameter
0.58 : 1 0.55 : 1 0.54 : 1 0.62 : 1 0.64 : 1 0.52 : 1
Pre-reactor temperature/ C 43.5 46.6 51.1 54.7 58.8 65.2
Reactor temperature/ C 65.9 62.2 64.1 63.6 63.3 62.1
Temperature in distillation reboiler/ C 77.8 76.5 75.5 77.4 75.8 76.5
Pressure/hPa 512 529 526 565 559 629
Flow-rate of 88 mass % solution of III/(mL min1 ) 3.0 3.1 3.7 3.0 2.8 3.0
Flow-rate of 14 mass % solution of VI/(mL min1 ) 7.9 7.7 8.2 8.0 8.3 7.9
Flow-rate of steam/(L min1 ) 2.5 2.5 2.5 2.1 2.0 2.0
Steam temperature/ C 79.6 81.2 83.9 80.5 84.7 81.5
Reaction time/min 120 120 120 120 110 120
Residence timea /s 52 52 52 52 52 52
pH in distillation reboiler 9.7 9.6 9.2 10.6 9.0 10.3

a) Measured as the time of ow of raw materials from the pre-reactor to distillation reboiler; residence time in the pre-reactor: 20 s.
1222 A. Krzyzanowska, E. Milchert/Chemical Papers 67 (9) 12181224 (2013)

collecting the distillate was tested. In the rst method,

the distillate from the top of the reactionstripping
column was collected. The pre-reactor temperature
was changed in the range of 43.565.2 C. The tem-
peratures in the reactor and distillation reboiler were
maintained at a constant level of 62.165.9 C and
75.577.8 C. The steam temperature at the entrance
to the distillation reboiler in the subsequent trials was
constant and remained in the range of 81.284.7 C on
average. The reactionstripping column was fed with
88 % aqueous solution of III at an average rate of
3.0 mL min1 ; the ow-rate of a 14 % solution of VI
was 7.58.3 mL min1 and the ow-rate of steam was
2.02.5 L min1 . The experimental results are sum-
marised in Table 1 and in Figs. 4a4d.
The highest selectivity of transformation of III to
V amounts to 96 %, with 93 % conversion. In the
second method of operation, the distillate was col-
lected from the distillation reboiler. In this method of
dehydrochlorination, the temperature of the reaction
mixture in the pre-reactor was changed in the range
of 53.067.0 C. The reactor temperature was main-
tained in the range of 66.070.5 C, and that of the
distillation reboiler in the range of 74.078.0 C. The
steam at 82.084.0 C was supplied at the ow-rate of
2.0 L min1 . III and VI ows were also similar. De-
hydrochlorination was carried out at reduced pressure
in the range of 520680 hPa; the residence time in the
pre-reactor and reactionstripping column was 52 s.
When the distillate was collected from the top of
the reactionstripping column, the conversion of III
at 45 C was higher than 90 % and increased slightly
with the increase in pre-reactor temperature. The pre-
reactor temperature signicantly aects the selectivity
of the transformation of III to V. With an increase in
the pre-reactor temperature from 44 C to 51 C, the
selectivity of transformation increased from 68 % to
95 %. Above this temperature, a gradual decrease in
selectivity to 78 % at 65 C was observed. In the work-
ing temperature range of the pre-reactor, a substantial
amount of 3-chloropropane-1,2-diol (VIII ) was formed
and the selectivity at a level of 6.9 % was achieved.
Glycerol was formed when the pre-reactor tempera-
ture was above 50 C and attained a maximum value
of 4.7 % at 51.1 C. Diglycidyl ether (X ) was formed
at temperatures below 50 C.
The process by which the distillate is collected from
the distillation reboiler permits achievement of almost
complete conversion of III. In comparable conditions,
the selectivity of the transformation to V is much
lower and increases from 74 % at 53 C to a maximum
of 87 % at 68 C. At temperatures above 56 C, XI and
X are the main by-products. Glycidol (XI ) is formed Fig. 4. The inuence of pre-reactor temperature on conversion
by dehydrochlorination of VIII which was prepared in of III and selectivity of transformation to V and by-
the hydration reaction of V. products: distillate collected from top of column (a) and
A comparison of the two methods of dehydrochlo- (b); distillate collected from distillation reboiler (c) and
rination diering in the method of distillate collection
(d); selectivity of V ( ); conversion of III ( );
VIII ( ); X ( ); XI ( ); VII ( ).
shows that it is preferable to collect the distillate from
 A. Krzyzanowska, E. Milchert/Chemical Papers 67 (9) 12181224 (2013)
Fig. 5. Proposed mechanism of diglycidyl ether (X ) formation. Reaction conditions: i) H2 O; ii) Ca(OH)2 , H2 O; iii) dehydrochlo-
rination.
the top of the reactionstripping column. Although a
lower conversion of III is achieved by this method, the
selectivity of transformation to V is much higher, up to
95.4 %. Collection of the distillate from the distillation
reboiler gives more by-products, which can be caused
by over-long residence time of V at high temperature
in the reactionstripping column. The epichlorohydrin
formed must pass through the whole length of the col-
umn before it leaves the reaction system. Residence
time of the reagents in the column was 40 s.
Formation of diglycidyl ether
Continuous dehydrochlorination of III leads to the
formation not only of VIII, XI, and VII, but also of
diglycidyl ether (bis(2,3-epoxypropyl) ether, 1,2:6,7-
diepoxy-4-oxaheptane) (X ). This compound was iden-
tied by GC/MS and NMR spectroscopy. Chemical
shift values were compared with data in the literature
(Cassel et al., 2001; Kamata et al., 2011).
Diglycidyl ether is present in the largest quantities
in the distillation reboiler at relatively low temper-
atures: pre-reactor 4145 C, reactor 4550 C, distil-
lation reboiler 5162 C. The formation of X occurs
when VIII and V are simultaneously in the reactor
and distillation reboiler.
The formation of X was conrmed in the reactions
carried out separately between V and VIII, in the pres-
ence of NaOH or Ca(OH)2 . This conrmed the forma-
tion of ether in this process. The proposed mechanism
for the formation of X is shown in Fig. 5.
Epichlorohydrin (V ) generated in the process un-
dergoes the reaction of hydration to give 3-chloropro-
pane-1,2-diol (VIII ). The reaction of VIII with V leads
to the formation of bis(3-chloro-2-hydroxypropyl)
ether (XII ). A proton from the hydroxyl group of
VIII is transferred to the nucleophilic oxygen atom
of the oxirane ring, so that an oxonium ion and alkox-
ide are formed. Then, the oxirane ring is opened and
the carbocation is formed. Both ions react to form
1223
XII. The presence of Cl and OH groups at adjacent
carbon atoms as well as a strongly alkaline reaction
medium cause dehydrochlorination with formation of
the oxirane ring. The reaction proceeds according
to the intra-molecular mechanism of ether formation
proposed by Williamson; the epoxy ring closes with
formation of 1-chloro-3-(oxiranylmethoxy)propan-2-ol
(XIII ). Further dehydrochlorination proceeds in the
same way. The second epoxide ring is formed and the
nal reaction product is diglycidyl ether (X ).
The formation of XIV in the reaction of XI with I
or with V was not found. Side-reactions during the de-
hydrochlorination of III to V are shown in Fig. 6. The
nal by-products of these transformations are glycerol,
chlorinated di-ethers and polyglycerols.
Conclusions
The process of continuous dehydrochlorination of
an 88 % aqueous solution of III with a 14 % solu-
tion of milk of lime proceeds with a high (95.4 %)
selectivity of the transformation to epichlorohydrin at
the pre-reactor temperature of 51 C, the reactor tem-
perature of 64 C, the distillation reboiler temperature
of 75 C, and with the removal of products, from the
top of the reactionstripping column. The accompa-
nying conversion of III is close to 93 %. Complete
conversion of this compound (99.7 %) is achieved at
the pre-reactor temperature of 67 C, reactor tempera-
ture of 72 C, distillation reboiler temperature of 78 C,
with the removal of products from the distillation re-
boiler. In both methods, the ow-rate of III solution
was 3 mL min1 , that of VI was of about 8 mL min1 ,
and that of steam 22.5 L min1 at pressure of 530
hPa. The VI/III mole ratio was in the range of 0.5 : 1
to 0.6 : 1.
In the post-reaction mixture, one of the by-
products is X, formed in the reaction of V with
VIII. Waste water generated by the reaction also
contained other ethers, such as XII and XIII. The
1224 A. Krzyzanowska, E. Milchert/Chemical Papers 67 (9) 12181224 (2013)
Fig. 6. Side-reactions during dehydrochlorination of III. Reaction conditions: i) H2 O; ii) dehydrochlorination; iii) dehydration.
other by-products are VIII, XI, VII, and polyglyc-
erols.
Acknowledgements. This work was nancially supported
from the Resources for Science in 20112014 as a Ministry
of Science and Higher Education research project (no. N N209
089940).
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