Microwave irradiation technique for synthesis of dialkyl dithiophosphoric acids

Article abstract of DOI:10.1080/10426500214305

Microwave heating technique was applied to the preparation of dialkyl dithiophosphoric acids from the reaction of alcohol with phosphorus pentasulphide. A microwave oven (CEM-MDS 2000) was utilized to determine the preparation conditions for the best yield of dialkyl dithiophosphoric acids under atmospheric pressure at various times and power. Six different (C₄-C₉) chain-length of dialkyl dithiophosphoric acids were studied. All experiments were performed in an open Teflon (poly-tetrafluoroethylene) vessel. The results obtained showed that the reaction of dialkyl dithiophosphoric acids can be achieved more rapidly using microwave heating than using conventional procedures.

Full text of DOI:10.1080/10426500214305

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Phosphorus, Sulfur, and Silicon and the Related
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Microwave Irradiation Technique for Synthesis of
Dialkyl Dithiophosphoric Acids
a
a
a
Bahattin Gümgüm , Nermin Bırıcık & Akın Baysal
a
Faculty of Arts and Science, Department of Chemistry , Dicle University , Diyarbakır,
Turkey
Published online: 27 Oct 2010.
To cite this article: Bahattin Gümgüm , Nermin Bırıcık & Akın Baysal (2002) Microwave Irradiation Technique for Synthesis
of Dialkyl Dithiophosphoric Acids, Phosphorus, Sulfur, and Silicon and the Related Elements, 177:10, 2507-2512, DOI:
10.1080/10426500214305
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Phosphorus, Sulfur and Silicon, 2002, Vol. 177:2507–2512
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Copyright �C 2002 Taylor & Francis
1
042-6507/02 $12.00 + .00
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DOI: 10.1080/10426500290110649
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MICROWAVE IRRADIATION TECHNIQUE
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FOR SYNTHESIS OF DIALKYL
DITHIOPHOSPHORIC ACIDS
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Bahattin G u¨ mg u¨ m, Nermin Bırıcık, and Akın Baysal
TRACTED RETRACTED RETRACTED RETRACT
Dicle University, Faculty of Arts and Science, Department
of Chemistry, Diyarbakır, Turkey
TRACTED RETRACTED RETRACTED RETRACT
(
Received November 6, 2001; accepted January 1, 2002)
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Microwave heating technique was applied to the preparation of dialkyl
dithiophosphoric acids from the reaction of alcohol with phosphorus
TRACTED
p
R
ent
E
asu
T
lph
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ide. A
A
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mic
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row
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av
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E
EM
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2000)
C
T
wa
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s utilized
D
RE
de-TRACT
to
termine the preparation conditions for the best yield of dialkyl dithio-
phosphoric acids under atmospheric pressure at various times and
TRACTED RETRACTED RETRACTED RETRACT
power. Six different (C –C ) chain-length of dialkyl dithiophosphoric
4
9
acids were studied. All experiments were performed in an open Teflon
TRACTED RETRACTED RETRACTED RETRACT
(
poly-tetrafluoroethylene) vessel. The results obtained showed that the
reaction of dialkyl dithiophosphoric acids can be achieved more rapidly
TRACTED
u
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sin
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icr
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edu
Keywords: Dialkyl dithiophosphoric acids; microwave irradiation;
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synthesis
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INTRODUCTION
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Organophosphorus compounds are important industrial reagents, us-
TRACTED RETRACTED RETRACTED RETRACT
1
ing alkyl phosphates for extraction of metal ions is well known. When
one ore more oxygen atoms of these compounds have been replaced by
TRACTED RETRACTED RETRACTED RETRACT
sulphur atoms, their “soft” thio analogues (organothiophosphorus com-
pounds) have been produced. These compounds have been prepared
TRACTED RETRACTED RETRACTED RETRACT
2
� 3
from the reaction of alcohols with phosphorus pentasulfide,
or with
oun
were prepared and investigated, and in the last five years a number
4
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omp
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dsTRACT
5
6
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o
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f re
The search for a rapid reaction technique has lead several workers
investigate the use of microwave radiation in the chemical react
D
view
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s w
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er
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e p
R
ubl
A
ish
C
ed.TED RETRACTED RETRACT
TRACTto
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atti
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m,
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ity,
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ionTRACT
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n Gu¨
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Fac
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ulty
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of A
rtsTRACT
and Sciences, Department of Chemistry, 21280 Diyarbakır, Turkey. E-mail:bgumgum@
dicle.edu.tr
TRACTED RETRACTED RETRACTED RETRACT
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2
507

TRACTED RETRACTED RETRACTED RETRACT
TRACTED RETRACTED RETRACTED RETRACT
2
508
B. G u¨ mg u¨ m et al.
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procedures. The application of microwave dielectric heating techniques
TRACTED RETRACTED RETRACTED RETRACT
for chemical synthesis has attracted considerable interest in recent
TRACT
TRACT
y
E
ear
accelerated using microwave heating.
iation in organic reactions were starte
the first article, four different types of organic reactions were stud-
d and seve different organic compounds prepared under pressure
D
s, an
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d
E
a w
T
id
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e ra
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ng
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e o
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an
Application of microwave ra-
d i 1986 with tw studies.
A
ic r
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eac
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tio
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ns
D
hav
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e b
E
eenTRACT
InTRACT
RETRACTED RETRACTED REinTRACT
1
1,12
d
E
D
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T
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E
D
R
E
T
n
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C
TED RE
o
TRACTie
E
D
n
1
3
a microwave oven. In the second microwave application, Diels-Alder,
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Claisen and Ene reactions were investigated with a significant decrease
1
4
in reaction time. Since 1986, the microwave heating technique grad-
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ually has gained widespread acceptance as a chemicals-preparation
method, and many reviews were published on the synthesis of chemi-
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cals or other organic or inorganic reactions by microwave heating.
Although microwave irradiation has been commonly used as a ther-
TRACTED RETRACTED RETRA23�C25 TED RETRACT
mal energy source in various fields of chemistry,
there are only a
26� 31
few articles on its applications in organophosphorus compounds,
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and not one on organothiophosphorus compounds.
Newly, phosphonate esters were prepared using a domestic mi-
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crowave oven, and a comprehensive examination of the Michaelis-
26
Arbuzov reaction under microwave irradiation was reported. In the
TRACTED RETRACTED RETRACTED RETRACT
second new research, several phosphonium salts were prepared using
a domestic microwave oven, and the microwave enhanced reaction
TRACTED RETRACTED RETRACTED RETRACT
of triphenylphosphine and an organic halide shows a remarkable
27
rate acceleration under microwave irradiation. In the third arti-
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cle, diethyl alkylphosphonates were efficiently and rapidly prepared
from trialkylphosphites and alkyl halides under short microwaves
TRACTED RETRACTED RETRACTED RETRACT
28
irradiations. In the fourth one, diethyl arylphosphonates were pre-
2
9
TRACT
TRACT
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p
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p
E
are
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ary
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.
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The
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herTRACT
two articles are related to microwave accelerated Wittig reactions-
3
0,31
ho
In the present work, different alcohols (C4 to C9) were treated with
hosphorus pentasulphide by icrowave heating, and the results co
D
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ylide
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p
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m
3
pared with conventional procedure. Thus in the first case, we have
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utilized the microwave method at atmospheric pressure for optimiza-
tion of the preparation of dialkyl dithiophosphoric acids.
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EXPERIMENTAL
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In this study, a CEM-MDS 2000 model microwave oven was used, with
double walled lined vessels made from Teflon-poly(tetrafluoroethylene).
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The MDS-2000 delivers approximately 630 watts of microwave energy
at a frequency of 2450 MHz at full power. The percent power may be
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Microwave Irradiation Technique
2509
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increased in 1% increments and the system is programable to control
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pressure from 0–200 psi in five separate stages. All of the chemicals
TRACT
u
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sed
D
wer
R
e a
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na
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lyt
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ical
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re
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age
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nt
gra
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Synthesis of Dialkyldithiophosphoric Acids
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Dialkyl dithiophosphoric acids were prepared by the reaction of phos-
phorus pentasulphide with different pure alcohols.
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4
ROH + P2S5 → 2(RO)2PSSH + H2S
TRACTED RETRACTED RETRACTED RE2,3TRACT
According to the chemical equation described in the literature
�
3
(
0.11 g, 2.5�10 mmol) phosphorus pentasulphide was weighed into
TRACTED RETRACTED RETRACTED RETRACT
poly(tetrafluoroethylene) vessels and 0.01 mmol of the investigated
alcohols were added. The microwave vessels containing mixture of
TRACTED RETRACTED RETRACTED RETRACT
�
3
0
.01 mmol alcohol and 2.5�10 mmol phosphorus pentasulphide were
placed in microwave oven. Different power stages; 63 W, 315 W, 504 W,
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and 630 W were applied at various times to determine the optimum
conditions for production of dialkyl dithiophosphoric acids. The vessels
TRACTED RETRACTED RETRACTED RETRACT
were allowed to cool to room temperature and excess phosphorus pen-
tasulphide was removed. The acidity of 0.2 g final product was deter-
TRACTED RETRACTED RETRACTED RETRACT
mined by titration of standardised 0.1 M of NaOH solution (Anal. calc.
for (C7H15O)2PSSH: C 51.50, H 9.57, S 19.64, P 9.49, found: C 51.67, H
TRACTED RETRACTED RETRACTED RETRACT
9
.78, S 19.36, P 9.21).
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TRACT
R
E
ES
D
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TS
E
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IS
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SI
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TRACTIn
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a
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in a flask and 1 mmol of phophorus pentasulphide gradually was added
ith constant stirrin under nitrogen tmosphere for 7–8 h at 7
R
ention
E
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4 C. The mixture was cooled and excess phophorus pentasulphide
3
TRACTED RETRACTED RETRACTED RETRACT
removed.
Dialkyl dithiophosphoric acids were prepared by the reaction of phos-
TRACTED RETRACTED RETRACTED RETRACT
phorus pentasulphide and alcohols by heating with microwave radia-
tion. The acidity of obtained products were determined by using the
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titration method with NaOH solution. Preparation conditions of dialkyl
dithiophosphoric acids by microwave methods under atmospheric pres-
TRACTED RETRACTED RETRACTED RETRACT
sure were examined. 63 W, 315 W, 504 W, and 630 W powers were
�
5
applied to 0.01 mmol of nonyl alcohol and 2.5�10 mmol of phosphorus
TRACTED RETRACTED RETRACTED RETRACT
pentasulphide in different times and in a single step to determine ap-
propriate conditions for producing dinonyl dithiophosphoric acid. The
TRACTED RETRACTED RETRACTED RETRACT
power application of 504 W for 3 min was found to be the best condition
(
Figure 1, Table I). By taking this result into account the preparation
TRACTED RETRACTED RETRACTED RETRACT
TRACTED RETRACTED RETRACTED RETRACT
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TRACTED RETRACTED RETRACTED RETRACT
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2
510
B. G u¨ mg u¨ m et al.
TRACTED RETRACTED RETRACTED RETRACT
TABLE I The Yield of Dinonyl
Dithiophosphoric Acid with Different
Microwave Powers and Times
TRACTED RETRACTED RETRACTED RETRACT
TRACTED RETRACTED RETRACTED RETRACT
TRACTED RET(R
imeACTED RETRACTED RETRACT
Yield (%)
T
min)
63 W
315 W
504 W
TRACTED RETRACTED RETRACTED RETRACT
1
2
29.90
49.80
E.80D R67
64.00
84.80
48.98
51.48
E.14TRA88
73.90
81.50
62.96
76.59
TRACTED RET
TRACTED RETRACTED RETRACTED RETRACT
3
4
5
RACT62
C.90 TED RETRACT
79.30
79.30
6
—
59.90
70.80
TRACTED RETRACTED RETRACTED RETRACT
TRACTED RETRACTED RETRACTED RETRACT
TRACTED RETRACTED RETRACTED RETRACT
TRACTED RETRACTED RETRACTED RETRACT
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FIGURE 1 The acidity of dinonyl dithiophosphoric acid with different mi-
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crowave powers.
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FIGURE 2 Under 504 W fixed power, the acidity of dibutyl, dipentyl, dihexyl,
TRACTED RETRACTED RETRACTED RETRACT
diheptyl, dioctyl, and dinonyl dithiophosphoric acids with different microwave
radiation time.
TRACTED RETRACTED RETRACTED RETRACT
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Microwave Irradiation Technique
2511
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TABLE II Under 504 W Fixed Power for
TRACTED RETRACTED RETRACTED RETRACT
3
min, the Yields of Dinonyl, Dioctyl,
Diheptyl, and Dihexyl, Dithiophosphoric
TRACTED RETRACTED RETRACTED RETRACT
Acids
TRACTED RETRACTED RETRACTED RETRACT
Compounds
Yield (%)
TRACTED RET(C9
R
H19
A
OP)
C
2SS
T
H
ED RETRA
8
93.7
95.3
C
8.9TED RETRACT
(
(
C8H17OP)2SSH
C7H15OP)2SSH
TRACTED RETRACTED RETRACTED RETRACT
(C6H13OP)2SSH
96.6
TRACTED RETRACTED RETRACTED RETRACT
durations of other dialkyl dithiophosphoric acids were determined un-
der 504 W fixed power (Figure 2, Table II) .
TRACTED RETRACTED RETRACTED RETRACT
The result shows that excellent yields were obtained within 1–3 min
of reaction time at fixed power 504 W. For lower chain alcohols, dibutyl
TRACTED RETRACTED RETRACTED RETRACT
and dipentyl dithiophosphoric acids require less time than that for
longer ones, dihexyl, diheptyl, dioctyl, dinonyl dithiophosphoric acids.
TRACTED RETRACTED RETRACTED RETRACT
Similarly, the required reaction time to produce the dialkyl dithiophos-
phoric acids were decreased by increasing the microwave energy power.
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It is possible to speculate that there exists a relationship between the
chain-length and the reaction time in the microwave radiation, and
TRACTED RETRACTED RETRACTED RETRACT
1
–3 min microwave heating time corresponds to 7–8 h of conventional
heating.
TRACTED RETRACTED RETRACTED RETRACT
In conclusion, we have demonstrated that synthesis of dialkyl dithio-
hosphoric acid can be accomplished as new and ver rapid meth
from the reaction of alcohol and phosphorus pentasulphide by mi-
owave radiation
TRACT
p
E
D
R
E
T
R
A
C
T
E
D
R
E
a
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A
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odTRACT
y
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D
R
E
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.
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TRACTED RETRACTED RETRACTED RETRACT
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TRACTED RETRACTED RETRACTED RETRACT
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TRACTED RETRACTED RETRACTED RETRACT
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