International Journal of Organic Chemistry, 2011, 1, 113-118
doi:10.4236/ijoc.2011.13017 Published Online September 2011 (
Copyright © 2011 SciRes. IJOC
Chemical and Microbiological Hydrolysis of Epoxides of
Acetylene Series
Mammad Veliyev1*, Mammad Salmanov2, Saida Aliyeva2,
Mahruza Shatirova1, Gulnara Yagubova2
1Institute of Polymer Materials of Azerbaijan Na tional Academy of Sciences, Baku, Azerbaijan
2Institute of Microbiology of Azerbaijan Nationa l Academy of Sciences, Baku, Azerbaijan
E-mail: *
Received July 21, 2011; revised August 25, 2011; accepted September 3, 2011
The chemical and microbiological hydrolyses of epoxide compounds of acetylene series have been compara-
tively carried out. It has been shown that as distinguished from chemical one in microbiological hydrolysis
along with corresponding optically active glycols, ketoalcohols of acetylene series are also formed. It has
been also defined that the synthesized glycols of acetylene series have bactericide properties related to sul-
fate-reducing bacteria at concentration of 100 - 200 mg/l. It has been established that an introduction of elec-
tron-acceptor chlorine atoms in molecules influence on decreasing of bactericide activity of acetylene gly-
Keywords: Hydrolyze, Glycols, Epoxide, Ketoalcohols, Acetylene
1. Introduction
As it’s known glycols find a wide application in many
branches of a national economy and have one of the
leading places among products of chemical industry.
They are used as monomers for whole series of polymer
materials, solvents, in production of plasticizers, for
making of antifreezes, polyester resins, synthesis of es-
ters of glycols, etc. The various methods of preparation
of diols both by chemical [1-7], and by microbiological
pathways [8-12] are known. Obtaining of the glycols of
acetylene series is occupied the special place. Acetylene
glycols possessing large chemical possibilities are suc-
cessfully used for synthesis of new perspective unsatu-
rated compounds, pharmaceutical preparations, mono-
mers for preparation of high-molecular compounds, in-
cluding biologically active substances and for solution of
important theoretical problems.
Analysis and systematization of literature data evi-
dence about availability of intensive process of expan-
sion of sphere of microbiological chemistry—new reac-
tions realized by microorganisms are revealed, circle of
converted substances is more expanded, and new taxo-
nomic groups of microorganisms are involved. Nowa-
days there are a lot of works reflecting rapid develop-
ment of use of microorganisms in organic and petro-
chemical synthesis [13-15]. The preparation of active
compounds by means of microorganisms is more eco-
nomic and safe than application of chemical methods.
For this reason this question is one of the most perspec-
tives. In particular, an investigation of hydrolysis of ep-
oxides by microorganisms has special interest for prepa-
ration of such compounds as glycols which have an im-
portant practical value.
The aim of this work is the synthesis of glycols of
acetylene series both by chemical and microbiological
hydrolysis of corresponding epoxide compounds of ace-
tylene series. This work is also a continuation of investi-
gations in the field of biodegradation of oil hydrocarbons
by microorganisms conducted previously by authors
2. Results and Discussion
The objects of investigation were monosubstituted ace-
tylene compounds with epoxide ring prepared by previ-
ously described method [5]. The reaction on oxirane ring
in presence of acidic catalysts has been carried out. It has
been established that in the presence of 10% of aqueous
solution of sulphuric acid the epoxides with terminal
acetylene bonds (Ia-Xa) are subjected to hydrolysis on
oxirane ring and in this case the corresponding glycols
(I-X) with high yields are formed (Scheme 1):
The structure of the synthesized glycols of acetylene
series (I-X) has been established by analysis of their IR-
and NMR-spectra. Proceeding of reaction on oxirane
ring has been confirmed by disappearance of absorption
band in the IR-spectra of compounds characteristic for
methylene group (3065 cm–1) and asymmetric valence
vibration of oxirane ring (915 cm–1). At the same time
the absorption bands at 3400 cm–1 and in the field of
1000 - 1170 cm–1, corresponding to hydroxyl group are
saved. In this case the absorption bands at 2130 and 3300
cm–1, confirming presence of terminal acetylene bond
were identified.
In the NMR-spectra of glycols (I-X) there are signals
as singlet with chemical shift at
2.65 ppm, correspond-
ing to protons of hydroxyl groups. Protons of methylene
group (2Н, СН2О) are appeared by signals as multiplet at
2.85-3.10 ppm., and proton of terminal acetylene bond
– as triplet at
2.23 - 2.26 ppm.
The structure of the prepared glycols (I-X) has been
also confirmed by counter synthesis—hydrolysis (10%
aqueous solution of sulphuric acid) of epoxyethynyl- and
propynylcarbinols (Ib-IIIb,VIb-XIIIb) and by further
splitting (in the presence of potassium hydroxide) of the
prepared products according to the known method [5] on
the following scheme (Scheme 2):
The physical-chemical constants and spectral data of
glycols of acetylene series (I-III, VI-VIII) prepared by
both methods are identical.
The synthesized glycols of acetylene series (I-VI)
were very reactive compounds and can be used in or-
ganic synthesis with the aim of preparation of new poly-
functional organic and silicoorganic compounds (deriva-
tives) with practically useful properties.
The carried out microbiological experiments showed
that strains from Aspergillus, Fusarium, Mucor, Penicil-
lium genera realized biohydrolysis of epoxide com-
pounds. As a result of screening of most active strain-
degrader it was chosen the strain Asperg illus n iger which
had maximum degree of biohydrolysis. The obtained
results are example of preparative method of hydrolysis
of epoxides of acetylene series with use of microorgan-
Analysis of products of biohydrolysis of epoxides by
chromatographic and spectral methods evidenced that
Aspergillus niger, as distinguished from chemical meth-
od realized biohydrolysis of epoxide compounds (Ia,
IVa-VIIa,IXa,Xa) in two direction with formation of
glycols (I, IV-VI, IX, X) (35% - 40%) and ketoalcohols
(XI-XVI) (60% -65%) on the following scheme (Scheme
The physical-chemical and spectral data of glycols (I,
IV-VI, IX, X) obtained as a result of microbiological
hydrolysis and same data of chemical method were iden-
tical. In the IR-spectra of ketoalcohols (XI, XVI) along
with absorption bands characteristic for terminal acety-
lene bond and hydroxyl group the absorption bands at
1740 cm–1, inherent for carbonyl group have been also
detected. In the NMR-spectra of compounds (XI-XVI)
the following chemical shifts of protons are present (,
ppm.): 2.22 - 2.25 t (HCC), 4.10 s (CH2O), 1.90 - 2.00 t
(CH2-CO), 2.50 s (OH).
An advantage of microbiological method is simulta-
neous formation of glycols and ketoalcohols of acetylene
series which are synthons in thin organic synthesis.
The synthesized glycols and ketoalcohols of acetylene
series are very reactive compounds and can be used as
synthons in thin organic synthesis for the purpose of
preparation of new polyfunctional organic and or-
ganosilicon derivatives with practically useful properties.
In particular, it has been shown that glycols (VI, VII)
undergo the hydroxylation reactions on acetylene bond.
Thiilation of glycols (VI, VII) with ethyl mercaptan pro-
ceeds in the presence of catalytic quantities of caustic
potassium and leads to formation of the thioethylsubsti-
tuted unsaturated glycols from a cis-configuration (XVII,
XVIII). Hydroxylation reaction of glycols (VI, VII) with
trialkylsilanes proceeds in presence of rhodium acety-
lacetonedicarbonyl by Farmer’s rule with formation of
glycols on a trans-structure (XIX-XXII), as it’s presented
on the Scheme 4.
Scheme 4: Thiilation and hydrosilylation of glycols of
acetylene series
The structure of the synthesized compounds (XVII-
XXII) has been established by the data of IR- and
NMR-spectroscopy. The reaction proceeding on acety-
lene compounds has been confirmed by disappearance of
absorption bands in the IR-spectra of compounds
(XVII-XXII), characteristic for H-CC fragment (2135
and 3300 cm–1). Thus in the spectra of compounds (XVII,
XVIII) there are absorption bands at 625 cm–1 and in the
field of 680 cm–1 - 725 cm–1, characteristic for C-S bonds
and cis- CH=CH groups. In the IR spectra of compounds
(XIX-XXII) the absorption are identified at 1625 cm–1,
groups specifying presence of CH=CH and fluctuations
at 986 cm–1 that testify formation of compounds (XIX-
XXII) on a trans-structure.
In the NMR1Н spectra of compounds (XIX-XXII)
signals of two protons were identified at double bonds
= 4.83 – 4.96 ppm and
= 5.52 – 5.65 ppm.
Spin-spin interaction constants (SSIC) of these protons
are different 13.5 - 14 Hz that is connected on their
trans-structure. In the NМR1Н spectra of compounds
(XVII, XVIII) signals of protons CH=CH in the form of
two doublets were identified
= 6.45 and
= 5.60 with
the constant of spin-spin interion J = 9 Hz that testify act
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Copyright © 2011 SciRes. IJOC
Scheme 1. Chemical hydrolysis of oxiranes of acetylene series.
Scheme 2. Counter synthesis of glycols of acetylene series.
Scheme 3. Microbiological hydrolysis of epoxides of acetylene series.
Scheme 4. Thiilation and hydrosilylation of glycols of acetylene series.
to compounds formation on cis-structure.
The synthesized glycols of acetylene series (I-X) have
been tested for bactericidal activity on sulfate-reducing
bacteria (SRB) by standard techniques [19-22]. It has
been established that they possess bactericidal properties
against SRB at concentration of 100 - 200 mg/l. The re-
sults of laboratory tests give the grounds to conclude that
the high bactericidal effect of the investigated glycols of
acetylene series, apparently, is the result of complex in-
fluence of acetylene bond and hydroxyl groups of mole-
cules. It was revealed that an introduction of elec-
tron-acceptor groups in molecule of acetylene glycols
(III, VIII) in comparison with glycols (I, II, IV-VII, IX,
X) bactericidal activity reduces to –70% at concentration
of 100 mg/l which at such concentration glycols (I, II,
IV-VII, IX, X) has a bactericidal activity of 95% - 98%.
Thus, at carrying out of this work the chemical and
microbiological methods of preparation of glycol and
ketoalcohols on the basis of hydrolyses of epoxides of
acetylene series have been developed. However it’s nec-
essary to emphasize that as a result of implemented che-
mical hydrolysis only glycols were formed but at micro-
biological hydrolysis the formation both of glycols and
ketoalcohols was observed. The carried out experiments
showed the advantages of new direction—microbi-
ological synthesis.
3. Experiment Materials
The IR-spectra of the synthesized compounds were taken
on spectrometer UR-20 within the range of 400 - 4000
cm–1 in thin layer. The spectra NMR 1H were recorded
on apparatus “Tesla BS –487 В” (80 MHz). Hexame-
thyldisiloxane, solvent-CCl4 was used as an internal
standard. The optical rotation was measured on po-
larimeter Perkin-Elmer-141. The purity of compounds
was controlled by the method of TLC on plates Silufol
UV-254, in various systems of solvents (benzene: diethyl
ether, 5:1, developer-iodine) and by the method of re-
versed-phase liquid chromatography on highly effective
liquid chromatography of firm “Kovo” (Czech) with
UV-spectrophotometric detector (
= 254 nm). The
column with sizes 3.3 × 150 mm with reversed phase
“Separon SGX C18” was used. Temperature 25˚C, mo-
bile phase: methanol:water (75:25 rev.%), feed rate 0.3
The physical-chemical data of compounds I, IV coin-
cide with literature data [23,24]. The microbiological
investigations were implemented by the microscopic
fungi isolated from water and ground of oil-polluted
coastal sites of Caspian Sea along the Absheron penin-
sula [15,17]. In this case 4 more active strains of fungi
conducted biohydrolysis of epoxides from genera: As-
pergillus, Fusarium, Mucor, Penicillium were selected.
The microbiological hydrolysis was studied by using of
the most active strain Aspergil lus niger 44.
4. Experiment Methods
4.1. Chemical Method
Chemical hydrolysis of epoxide compounds (Ia-XIa).
To 20 ml 10% aqueous solution of sulphuric acid was
gradually added 3.4 g (0.05 mol) 1.2-epoxy-3-butin (Ia).
In view of significant isolation of heat a reaction flask
was cooled in the process of reaction by ice water. After
half-hour mixing the reaction was finished. The aqueous
solution was saturated by common salt and multiply was
extracted by ester and then by chloroform. After distilla-
tion of solvent glycol (I) with Tm 39˚C - 40˚C, yield
85.4% was isolated. Found, %: С 55.90, Н 7.16. C4H6O2.
Calculated, %: С 55.80, Н 7.03.
The compounds (II-X), chararacterizing by following
constans was analogously prepared:(II) M.p. 55˚C - 56˚C,
yield 82.5%. Found, %: С 60.31, Н 8.12. C5H8O2. Cal-
culated, %: С 60.2, Н 8.05. (III), M.p. 64˚C - 65˚C, yield
80.1%. Found, %: С 39.70, Н 4.24. Cl 29.30. C4H5ClO2.
Calculated, %: С 39.86, Н 4.18, Cl 29.41; (IV), M.p
47˚C - 48˚C, yield 82.3%. Found, %: С 63.24, Н 8.62.
C6H10O2. Calculated, %: С 63.13, Н 8.83; (V), M.p.76˚C
- 77˚C, yield 85.2%. Found, %: С 74.16, Н 6.01.
C10H10O2. Calculated, %: С 74.05, Н 6.22; (VI), M.p.
44˚C - 45˚C, yield 90%. Found, %: С 59.82, Н 8.20.
C5H8O2. Calculated, %: С 59.98, Н 8.05. (VII), M.p.
59˚C - 60˚C, yield 85.8%. Found, %: С 63.02, Н 8.74.
C6H10O2. Calculated, %: С 63.13, Н 8.83. (VIII),
M.p.67˚C - 68˚C, yield 83.4%. Found, %: С 44.56, Н
5.18, Cl 26.48. C5H7ClO2. Calculated, %: С 44.63, Н
5.25, Cl 26.35; (IX), M.p.52˚C - 53˚C, yield 83.1%.
Found, %: С 65.42, Н 9.38. C7H12O2. Calculated, %: С
65.59, Н 9.43; (IX), M.p.52˚C - 53˚C, yield 83.1%.
Found, %: С 65.42, Н 9.38. C7H12O2. Calculated, %: С
65.59, Н 9.43; (X), M.p.81˚C - 82˚C, yield 86.8%. Found,
%: С 74.81, Н 6.73. C11H12O2. Calculated, %: С 74.97, Н
4.2. Microbiological Method
Microbiological hydrolysis of epoxide compounds (Iа,
IVа-VIa, IXa, Xa). а) Preparation of fungi biomass.
For preparation of biomass of selected fungi 3l fermenter
filled by 1l liquid nutrient medium (wort) was used. In
this case to a medium was added 10 ml of liquid paraffin
and 0.005 ml antifoam silicon for prevention of pouring.
The incubation was carried out under temperature 25˚C -
27˚C. Then the suspension of mycelium and collection of
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1-week culture of the investigated microorganisms was
added. After two-day incubation mycelium was filtered,
washed by sterile water and placed back in fermenter,
which already filled by 1l рН 7 phosphate buffer (0.1 М)
solution, and also a medium was enriched by nitrogen
and air. A yield of product was provided by phased
treatment of probes: for each probe mycelium was fil-
tered and the prepared fungi biomass used in further ex-
periments for implementing the biohydrolysis. After de-
cantation a liquid phase was treated by NaCl and then
was extracted twice by ether. The organic layer was
dried (MgSO4), and then was evaporated in vacuum.
b) Biohydrolysis. Biohydrolysis was carried out in
Erlenmeyer flasks (0.5l), containing buffer phosphate
(0.1l, 0.1М, рН 8) and 10% fungi biomass prepared from
previous experiment. The solution of epoxides of acety-
lene series (Ia, IVa) (0.1 - 1 g) in EtOH (1 ml) was
poured into medium, and a flask was incubated under
temperature 27˚C for 1 - 4 days. After decantation a liq-
uid phase was treated by NaCl, and then twice extracted
by ester. The organic layer was dried by (MgSO4), and
then was evaporated in vacuum. After removal of ester
by re-crystallization the products (I, IV-VI, IX, X) and
(XI, XVI) were separated.
(I): M.p. 39˚C - 40˚C (from benzene),
= –29.6
(с 2.42, EtOH); (IV): M.p. 47˚C - 48˚C (from benzene),
= –20.3 (с 2.21, EtOH); (V): M.p. 76˚C - 77˚C
(from benzene),
= -22.2 (с 2.39, EtOH); (VI):
M.p. 44˚C - 45˚C (from benzene),
= –38.1 (с,
2.51, EtOH); (IX): M.p. 52˚C - 53˚C (from benzene),
= –23.7 (с 2.44, EtOH); (X): M.p. 81˚C - 82˚C
(from benzene),
= -26.4 (с 2.82, EtOH); (XI): B.p.
67˚C - 68˚C (100 mm.merc.c.), 20
n = 1.4490,
1.0636; Found, %: С 57.28, Н 4.60. C4H4O2. Calculated
%: С 57.14, Н 4.79; (XII): B.p. 76˚C - 77˚C (100
n = 1.4695, 1.0272; Found, %: С
64.39, Н 7.06. C6H8O2. Calculated, %: С 64.27, Н 7.18;
(XIII): B.p. 92˚C - 93˚C (100 mm.merc.c.),
n =
1.5605, 1.1694; Found, %: С 74.78, Н 5.16.
C10H8O2. Calculated, %: С 74.99, Н 5.02; (XIV): B.p.
73˚C - 74˚C (100 mm.merc.c.),
n = 1.4535,
1.0277; Found, %: С 61.09, Н 6.27. C5H6O2. Calcu-
lated, %: С 61.21, Н 6.16; (XV): B.p. 79˚C - 80˚C (100
n = 1.4729, 1.0098; Found, %: С
66.50, Н 7.82. C7H10O2. Calculated, %: С 66.64, Н 7.99;
(XVI): B.p. 97˚C - 98˚C (100 mm.merc.c.),
n =
1.5640, 1.1561. Found, %: С 75.71, Н 5.62.
C11H10O2. Calculated, %: С 75.84, Н 5.78.
Addition of ethyl mercaptan to glycol (VI, VII).
General methodology. To the boiling solution 0.08
mole of glycol (VI or VII) and 0.4 g of KOH in 10 ml of
methyl alcohol and within 1 hour it was added 11.7 g of
ethyl mercaptan. After heating within 2 hours to reaction
mass was added 50 ml of ether, then washed by water
and dried up over MgSO4. The solvent was removed and
with distillation in vacuum the compounds (XVII, XVIII)
were isolated by the following constants: (XVII), B.p.
97˚C - 98˚C (1 мм), 20
1.4805, 1.0133, yield
63.6%. Found, %: C 51.70, H 8.54, S 19.87. С7Н14O2S.
Calculated, %: C 51.82, H 8.69, S 19.76; (XVIII), B.p.
105˚C - 106˚C (1mm),
n 1.4840, 1.0056, yield
64.8%. Found, %: C 54.38, H 9.03, S 18.28. С8Н16O2S.
Calculated, %: C 54.50, H 9.15, S 18.19.
Hydrosilyation of glycols (VI, VII) with triethyl-
(or trietoxy)silane. 0.32 mol of compounds (VI or VII)
and 0.32 mole of triethyl (or trietoxy) silane in the pres-
ence of 0.01 g of rhodium acetylacetonatdicarbonyl was
mixed during 7 hours under the temperature 55°C - 60°C
and subjected to the vacuum distillation the compounds
(XIX-XXII) were isolated with the following constants:
(XIX), B.p. 121˚C - 122˚C (1 mm), 20
0.9335, yield 72.4%. Found, %: C 61.20, H 11.09, Si
12.82. С11Н24O2Si. Calculated, %: C 61.05, H 11.18, Si
12.97; (XX), B.p. 126˚C - 127˚C (1 mm),
n = 1.4785,
1.1011, yield 78.3%. Found, %: C 49.82, H 9.28, Si
10.51. С11Н24O5Si. Calculated, %: C 49.91, H 9.15, Si
10.62; (XXI), B.p. 125˚C - 126˚C (1 mm),
n = 1.4765,
0.9338, yield 73.8%. Found, %: C 62.41, H 11.22,
Si 12.03. С12Н26O2Si. Calculated, %: C 62.54, H 11.37,
Si 12.19; (XXII), B.p. 129°C - 130˚C (1 mm),
n =
1.4820, 1.1647, yield 78.6%. Found, %: C 51.62, H
9.30, Si 10.19. С12Н26O5Si. Calculated, %: C 51.76, H
9.41, Si 10.08.
5. Conclusions
The methods of preparation of glycols of acetylene series
by the chemical (in the presence of 10% aqueous solu-
tion of sulphuric acid) and microbiological (in the pres-
ence of Aspergillus nig er, Fusarium, Mucor, Penicillium)
hydrolysis of the corresponding epoxide compounds of
acetylene series have been developed. In using of micro-
biological method the epoxide compounds unlike che-
mical method are hydrolyzed in two directions with for-
mation of the corresponding optically active glycols and
ketoalcohols. It has been established that the synthesized
glycols of acetylene series undergo the thiilation reaction
with ethylmercaptane with formation of thioethyl substi-
tuted unsaturated glycols with cis-configura- tion. Unlike
this the analogous hydrosilylation reaction of glycols
with trialkylsilanes proceeds with formation of trialkyl-
silyl substituted unsaturated glycols with tran s -structure.
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