In situ study of the interaction between tert-butyl chloride and aluminum activated with liquid in-ga eutectic

Article abstract of DOI:10.1134/S0023158410030043

The interaction between tert-butyl chloride and activated aluminum was studied by attenuated total reflectance Fourier transform infrared spectroscopy near room temperature (18-25°C). A long induc- tion period of ?240-260 min was observed. The AlCl₄^- ionic aluminum chloride complexes [AlnCl₃n+1]^-(n = 1, 2) and the molecular species AlCl₃ were identified at the activated aluminum/tert-butyl chloride interface during the reaction. The formation of the ion in the liquid medium and the presence of the same ion and a molecular AlCl₃ ^-tert-butyl chloride complex in the resinous products of the reaction were confirmed by ²⁷Al NMR spectroscopy. The reaction products were analyzed qualitatively by GC/MS. The reactivities of activated aluminum and anhydrous aluminum chloride toward tert-butyl chloride under the same conditions were compared. A distinctive feature of the interaction activated aluminum and tert-butyl chloride is the dominant formation of the AlCl₄ ^-ion. By contrast, the interaction between aluminum chloride and tert-butyl chloride yields the polynuclear ion and,Al₂Cl₇ ^- likely,Al₃Cl₁₀^-. Pleiades Publishing, Ltd., 2010.

Full text of DOI:10.1134/S0023158410030043

ISSN 0023ꢀ1584, Kinetics and Catalysis, 2010, Vol. 51, No. 3, pp. 354–358. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © A.B. Arbuzov, V.A. Drozdov, V.A. Likholobov, M.V. Trenikhin, V.P. Talsi, E.N. Kudrya, 2010, published in Kinetika i Kataliz, 2010, Vol. 51, No. 3,
pp. 375–379.
In Situ Study of the Interaction between tertꢀButyl Chloride
and Aluminum Activated with Liquid In–Ga Eutectic
A. B. Arbuzova, V. A. Drozdovb, V. A. Likholobovb, M. V. Trenikhina, V. P. Talsia, and E. N. Kudryaa
a Institute of Hydrocarbon Processing, Siberian Branch, Russian Academy of Sciences, Omsk, 644040 Russia
b Omsk Scientific Center, Siberian Branch, Russian Academy of Sciences, Omsk, 644040 Russia
eꢀmail: drozdov@ihcp.oscsbras.ru
Received May 27, 2009
Abstract—The interaction between tertꢀbutyl chloride and activated aluminum was studied by attenuated
total reflectance Fourier transform infrared spectroscopy near room temperature (18–25°C). A long inducꢀ
tion period of ~240–260 min was observed. The ionic aluminum chloride complexes [AlnCl3 +1]– (
n
= 1, 2)
n
and the molecular species AlCl3 were identified at the activated aluminum/tertꢀbutyl chloride interface durꢀ
ing the reaction. The formation of the
a molecular AlCl3
− ion in the liquid medium and the presence of the same ion and
AlCl4
–tertꢀbutyl chloride complex in the resinous products of the reaction were confirmed by
27Al NMR spectroscopy. The reaction products were analyzed qualitatively by GC/MS. The reactivities of
activated aluminum and anhydrous aluminum chloride toward tertꢀbutyl chloride under the same conditions
were compared. A distinctive feature of the interaction activated aluminum and tertꢀbutyl chloride is the
dominant formation of the
− ion. By contrast, the interaction between aluminum chloride and tertꢀbutyl
AlCl4
−
−
chloride yields the polynuclear ion
DOI: 10.1134/S0023158410030043
and, likely,
.
Al3Cl10
Al2Cl7
Aluminum metal is presently viewed as a promising like aluminum chloride Lewis acids can form on the
material for unconventional energy engineering [1–3] activated aluminum surface under the action of the
and catalysis [4–10]. By oxidation of aluminum [4] or reaction medium. Even under mild conditions, these
its activated copperꢀ, nickelꢀ, cobaltꢀ, or zincꢀconꢀ active species can involve hydrocarbons from various
taining alloys with water [5] followed by calcination of homological series into acidꢀcatalyzed reactions, such
the resulting precipitate, it is possible to obtain supꢀ as isomerization, alkylation, and oligomerization.
ports for various processes, including CO oxidation.
Here, we report an in situ attenuated total reflecꢀ
Gaponik and Mardykin [6] reported the synthesis of
tance Fourier transform infrared spectroscopy
higher triꢀnꢀalkylaluminums (olefin polymerization
(ATRꢀFTꢀIR) and NMR study of the reaction
between activated aluminum and tertꢀbutyl chloride
for the purpose of identifying the resulting aluminum
chloride complexes.
cocatalysts) via the reaction between an aluminum
and magnesium metal powder and an alkyl halide at
60–70°С. Sadykov and Teregulov [7] studied, by the
chemical nuclear polarization method, the interaction
between an overstoichiometric amount of iodine
vapor–activated aluminum powder and tertꢀbutyl
chloride at 60–70°С in dioxane and inferred that this
reaction occurs via a freeꢀradical mechanism. Sadykov
et al. [8] were the first to carry out the conversion of
cyclohexane into decalins at room temperature under
the action of aluminum halides obtained in situ by
reacting an iodineꢀactivated aluminum metal powder
EXPERIMENTAL
Aluminum Samples and Activation of Aluminum
with Liquid In–Ga Eutectic
Samples of aluminum metal (Adꢀ1 brand, USSR
State Standard GOST 4784ꢀ74, 99.3 wt % Al, main
impurities: Si, Fe, Ti, Cu, Mn) were
plates with a thickness of 3 mm. The activator was In–
Ga eutectic (76 wt % Ca, m = 15.9°С). Aluminum
was activated at room temperature by placing a drop
l) of the liquid alloy on the surface of the initial
4
×
4 mm polished
with methyl halides CCl4, CHCl3, CHBr3, CH2Cl2
,
and CH2Br2). A carbonium mechanism was suggested
for the reactions involved in this synthesis.
Т
We demonstrated earlier that massive aluminum (20
μ
activated with liquid In–Ga eutectic can react with aluminum plate [11]. The contact time was 24–36 h.
chloroalkanes, including tertꢀbutyl chloride, near Because the aluminum surface is covered by oxide layꢀ
room temperature to yield a wide variety of products ers that are not wetted by the eutectic alloy, the sample
[9, 10]. It was hypothesized that catalytic complexes was initially scratched with a metallic needle. Anhyꢀ
354

IN SITU STUDY OF THE INTERACTION BETWEEN tertꢀBUTYL CHLORIDE
355
drous aluminum chloride (Aldrich) was used as the SEARCH 05 mass spectral library, which contains the
model compound.
spectra of 250000 species. The relative amounts of
components in the gas and liquid phases were estiꢀ
mated separately.
ATRꢀFTꢀIR Spectroscopy
The interaction between tertꢀbutyl chloride and
activated aluminum around room temperature (18–
25°С) was studied by ATRꢀFTꢀIR spectroscopy on a
Nicolet 5700 spectrophotometer (Thermo Electron
Corp.). The ATRꢀFTꢀIR cell employed a ZnSe crystal
in a metallic holder, to which a 30ꢀml cylindrical glass
vessel for the solid and liquid reactants was glued with
epoxy. The IR beam was incident on the solid activated
aluminum/liquid tertꢀbutyl chloride interface from
below at an angle of 45°. The effective penetration
RESULTS AND DISCUSSION
In the time interval of 2–240 min, no interaction
between activated aluminum and liquid tertꢀbutyl chloꢀ
ride was observed visually in the IR cell; that is, there
was no observable dissolution of the solid phase, gas
evolution, or changes in the color of the liquid medium.
Throughout this time interval, the ATRꢀFTꢀIR specꢀ
trum of the reaction medium in the 500–650 cm–1
range showed an absorption band at 567 cm–1 due to
depth of the IR beam was 0.4–3.3
μ
m in the 500–
the C⎯Cl bond, which did not vary with time. No
4000 cm–1 spectral range.
changes relative to the spectrum of the initial liquid
tertꢀbutyl chloride were also observed in the regions of
C–C stretching vibrations in the carbon backbone
(780–830 cm–1) and C–H stretching vibrations
(2750–3100 cm–1).
The observed induction period of ~240–260 min
cannot be explained solely in terms of diffusion as in
the reaction between activated aluminum and water, in
which the resulting film of boehmite (reaction prodꢀ
uct) hinders the access of water to aluminum [13, 14].
In our case, the main cause of the induction period is
likely the rapid formation of an AlCl(s) surface layer
via the dissociative adsorption of the chloroalkane [15,
16], which turns slowly into AlCl3(s) (because of the
negative entropic factor) before the main reaction
[17]:
IR spectroscopic measurements were carried out as
follows. Liquid tertꢀbutyl chloride was poured into the
cell, and its background spectrum was recorded. Next,
activated aluminum was placed into the cell and IR
spectra were recorded at regular intervals of ~10–
15 min at a preset cell temperature. The background
spectrum of tertꢀbutyl chloride or that of the zinc
selenide crystal was subtracted from the resulting specꢀ
tra. The number of scans was 30, and the spectral resꢀ
olution was 4 cm–1. The interaction between anhyꢀ
drous aluminum chloride and liquid tertꢀbutyl chloꢀ
ride was also studied using this procedure under the
same conditions.
NMR Spectroscopy
3AlCl(s)
→
AlCl3(s) + 2Al.
The structure of the components of liquid media
As the reaction mixture is held in the IR cell, the
chemical reaction between activated aluminum and
tertꢀbutyl chloride begins in 260 min. New absorption
bands at 495, 526, and 611 cm–1 appear in the
ATRꢀFTꢀIR spectrum, and the strong band at
567 cm–1, observed in the initial spectrum, disappears
(Fig. 1a). Intensive gas evolution is observed in the IR
cell, accompanied by the formation of a resinous, dark
red substance around the activated aluminum plate.
The reaction ends in complete aluminum dissolution
in the reaction medium and in the formation of a visꢀ
cous layer of resinous products.
13
was additionally studied by 27Al and C NMR specꢀ
troscopy at working frequencies of 52 and 50 MHz,
respectively, in a magnetic field of 4.7 T on an ACꢀ200
(Bruker) NMR spectrometer. The external standards
13
were Si(CH3)4 and 1 M Al(NO3)3 · 9H2O for C and
27Al NMR spectroscopy, respectively.
GC/MS
The resulting products were identified by GC/MS
using an Agilent 6890/5973N system (Agilent Techꢀ
nologies). Analyses were performed in the temperaꢀ
tureꢀprogrammed mode, linearly raising the oven
temperature from 40 to 250°С at a rate of 10 K/min,
with a capillary nonpolar column 0.25 mm in diameter and 526 cm–1 to the
Taking into account data available from the literaꢀ
ture [18–20], we assigned the absorption bands at 495
−
−
and
ions. The IR
Al2Cl7
AlCl4
and 30 m in length (HPꢀ5ms, Agilent Technologies).
Electronꢀimpact ionization was used. The ionizing
electron energy was 70 eV. The mass analyzer was a
195ꢀmm goldꢀcoated quartz quadrupole mass filter.
The mass measurement range was 1.6–800 amu. Use
of the scanning mode made it possible to identify indiꢀ
vidual components of complex mixtures. Control of
the GC/MS system, analyses, and data processing
were carried out using the specialꢀpurpose computer
transmission spectrum of the 1ꢀmethylꢀ3ꢀethylimidaꢀ
zolium chloride–anhydrous aluminum chloride (1 : 1)
ionic liquid was reported to have a broad band at
489 cm–1 [18], which was assigned by the authors to
vibrations of the tetrahedral anion
−. The IR
AlCl4
transmission spectra of the 1ꢀbutylpyridinium chloꢀ
ride–anhydrous aluminum chloride ionic liquid (1 : 1
and 1 : 2) exhibit broad bands at 490 and 545 cm–1
AlCl4−
Al2Cl7−
program MSD ChemStation and the NIST MS [19], which were assigned to the
and
KINETICS AND CATALYSIS Vol. 51
No. 3
2010

356
Absorbance
ARBUZOV et al.
characteristic of branched alkyl substituents and polyꢀ
isobutylene [23, 24], products of the reaction.
495
(a)
6
Figure 1b displays ATRꢀFTꢀIR spectra in the
0.4
0.2
0
2600–3050 cm–1 range, which accommodates the
5
4
H⎯Cl stretching vibrations of hydrogen chloride [25,
526
26]. The absorption band at 2876 cm–1 arises from the
H–Cl stretching vibrations of hydrogen chloride in
lowꢀpolarity media [25], and the band at 2720 cm–1
characterizes the same vibrations of HCl in polar
media and ionic liquids [26]. It is possible that the
resulting hydrogen chloride favors the dissolution of
activated aluminum to yield aluminum chloride.
3
688
611
2
1
810
Thus, its was demonstrated by in situ ATRꢀFTꢀIR
spectroscopy that the reaction between activated aluꢀ
minum and tertꢀbutyl chloride proceeds via the formaꢀ
−
0.2
567
400
500
600
700
800
900
tion of [AlnCl3 + 1]– (
n
= 1, 2) ionic complexes, which
n
(b)
are possibly stabilized by intermediate carbocations
0.02
0
+
2876
(such as tert
ꢀ
) or Н+ (HCl). Apparently, the
С4Н9
6
source of these complexes is the observed molecular
species AlCl3. It is likely these complexes that are catꢀ
alytic species in the reaction.
5
4
3
2
2720
1
NMR data confirm the results of ATRꢀFTꢀIR
spectroscopy and indicate the appearance of the
anion in the liquid medium during the reaction
as an intense 27Al signal with a chemical shift of
2926
2947
−0.02
AlCl4−
−
0.04
0.06
(
103.5 0.5) ppm (Fig. 2a) [27]. Figure 2b presents
2974
2985
the 27Al NMR spectrum of the resinous products
diluted with tertꢀbutyl chloride. This spectrum indiꢀ
cates the presence of two aluminum chloride species,
−
2500 2600 2700 2800 2900 3000 3100
Wavenumber, cm−
AlCl4
tert С4Н9Cl] complex (98.0 ppm). The latter
1
namely,
AlCl3
(103.5 ppm) and, apparently, the
[
–
ꢀ
Fig. 1. Time variation of the ATRꢀFTꢀIR spectrum in the
interaction between activated aluminum and tertꢀbutyl
assignment is supported by the fact that, for a solution
of anhydrous aluminum chloride in the thionyl chloꢀ
ride–sulfur dioxide mixed solvent, the resonance at
= 97.6 ppm was attributed to the [AlCl3–SO2] comꢀ
plex [28].
Massive anhydrous aluminum chloride also
decomposes tertꢀbutyl chloride at room temperature
[29]. For comparison, we studied this reaction by
ATRꢀFTꢀIR spectroscopy. nꢀHexane was used here as
the solvent, otherwise the reaction would occur vioꢀ
lently and uncontrollably (Fig. 3).
Initially (~5 min), the ATRꢀFTꢀIR spectrum
shows a broad band at 527 cm–1 with shoulders at 505
and 548 cm–1. Later, a band at 586 cm–1 appears,
whose intensity grows with time, like the intensity of
the 527 cm–1 band. It was mentioned above that the
chloride (
H stretching vibrations: (
) 331, and ( ) 342 min.
Т
= 25°С) in the region of (a) C–Cl and (b) C–
1
) 261, ( ) 308, ( ) 320, ( ) 327,
2
3
4
δ
(5
6
anions, respectively. Bands at 475 and 517 cm–1 were
observed in the IR emission spectra of MCl–AlCl3
alloys (M = alkali metal), and, based on normal mode
AlCl4−
theory, these bands were assigned to the
and
Al2Cl7−
ions [20].
The weak absorption band at 611 cm–1, which
appears in the spectrum simultaneously with the bands
at 495 and 526 cm–1, can be due to the molecular speꢀ
cies AlCl3, according to other authors [21, 22]. It was
observed by lowꢀtemperature IR spectroscopy in optiꢀ
527 cm–1 band is assignable to the
band at 586 cm–1 is likely due to the
anion. The
anion. The
Al2Cl7
Al3Cl10
cal cryostats (
high absorbance in this region was observed for anhyꢀ
drous aluminum chloride vapor ( = 700 K).
Т = 150 K) [21]. In another study [22],
−
nearby band at 587 cm–1 was also observed in the lowꢀ
temperature (77–250 K) IR spectra of the products of
condensation between anhydrous aluminum chloride
Т
Note the systematic weakening of the C–Cl
stretching band of tertꢀbutyl chloride at 567 cm–1 in
time, which indicates that the chloroalkane undergoes
conversion during the reaction.
and tertꢀbutyl chloride in the nꢀoctane matrix [30].
Thus, the reaction between aluminum chloride and
tertꢀbutyl chloride takes place mainly via the formaꢀ
The spectrum additionally shows new absorption
bands at 1490, 1363, 1105, and 967 cm–1, which are
−
tion of the dinuclear ionic complex
and, likely,
Al2Cl7
KINETICS AND CATALYSIS Vol. 51
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IN SITU STUDY OF THE INTERACTION BETWEEN tertꢀBUTYL CHLORIDE
357
103.5
Absorbance
(a)
527
−
AlCl4
7
0.9
505
548
6
5
0.6
0.3
4
3
586
696
2
1
115
(b)
110
105
103.5
100
95
0
−
AlCl4
400
500
600
700
800
Wavenumber, cm−
900
1
Fig. 3. Time variation of the ATRꢀFTꢀIR spectrum in the
interaction between anhydrous aluminum chloride and
AlCl3ꢀtertꢀC4H9Cl
tertꢀbutyl chloride (
stretching vibrations: (
32, and ( ) 39 min.
Т
= 25°С) in the region of C–Cl
) 5, ( ) 9, ( ) 12, ( ) 15, ( ) 22, (
1
2
3
4
5
6)
98.0
7
likely due to the conversion of isobutene, a product of
the reaction examined, via conjugated oligomerizaꢀ
tion on the resulting aluminum chloride complexes
[10]. Similar alkene conversion processes occur under
the action of concentrated sulfuric acid [32] or sulꢀ
fated zirconia [33].
115
110
105
100
95
Chemical shift, ppm
27
Fig. 2. Al NMR of the reaction medium (
Т
= 25°С): (a)
interaction between activated aluminum and tertꢀbutyl
chloride; (b) dilution of the resinous products with and
tertꢀbutyl chloride.
−
CONCLUSIONS
the trinuclear complex
. This differentiates the
Al3Cl10
reaction between aluminum chloride and tertꢀbutyl
chloride from the reaction between activated alumiꢀ
Although there is long induction period in the
interaction between activated aluminum and tert
ꢀ
num and tertꢀbutyl chloride: the main product of the
butyl chloride, this reaction continues until the comꢀ
plete dissolution of the metal, yielding gaseous, liquid,
−
latter is
.
AlCl4
According to GC/MS data, the main gasꢀphase and resinous products. Due to the continuous generaꢀ
components observed in the reaction between actiꢀ tion of [AlnCl3 + 1]– (
n
= 1, 2) ionic complexes on the
n
vated aluminum and tertꢀbutyl chloride are isobutane aluminum surface, the dominant route of the reaction
(~31 rel. %), hydrogen chloride (~22 rel. %), unreacted is the conjugated oligomerization of isobutylene, an
tertꢀbutyl chloride (~40 rel. %), air (~5 rel. %), and intermediate compound.
minor amounts of isobutene (<2 rel. %). The major liqꢀ
The ability of activated aluminum to react with
uid products are 2ꢀchloroꢀ2ꢀmethylbutane (~17 rel. %),
chloroalkanes opens up the possibility of carrying out
2ꢀchloroꢀ2,3ꢀdimethylbutane (~16 rel. %), and
isobutane alkylation with butenes on this catalyst. This
2ꢀchloroꢀ2,5,5ꢀtrimethylhexane (~18 rel. %), as well
can be done, e.g., in the presence of a controllable
as unreacted tertꢀbutyl chloride (~49 rel. %). The presꢀ
amount of tertꢀbutyl chloride owing to the in situ forꢀ
ence of these hydrocarbons is confirmed by 13C NMR
mation of aluminum chloride complexes of different
data.
compositions.
The presence of chlorinated hydrocarbons with
different numbers of carbon atoms can be due to tert
ꢀ
butyl chloride conversion proceeding via the formaꢀ
tion of radicals [7] or carbene on the surface of actiꢀ
vated aluminum [31].
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