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Dissolution of Bituminous Coals at Temperatures below 200 ░C.

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quinoline, isoquinoline, benzimidazole, benzothiazole, benzoxazole, benzoselenazole, and their substitution products
could be used in the syntheses.
The salts ( 4 ) react as electrophiles having ambidentate
reactivity in the routes (d) or (e).
Hard bases, X, react according to route (d) with substitution
of the azido group o n the hard carbonium ion of ( 4 b ) .
1. Hydrolysis of azidinium salts.
+ HOQ
(-&-N3
I
R
BF,@
+ H C R’
~O
Q=N-N=NB
\.k2
A
R
R1
-q
R
C=O + HN3
+
5. Addition of heteroaromatic amines such as (15) with
formation of condensed triazoles (16).
BF,@
(51.
I
R
~.
4
N
I
R
r
1
L
-I
+
BF,Q
H3C
(15)
(44
cC-N=CQ
NO
i
I
R BF40 R
(6)
(5)
(4b)
+ s=g=C:,,
iY
R
BF,@
I
(13)
O C = N H
2. Synthesis of azamonomethinecyanines (6) with the bases Q=N-N=N@
I
q = N - N = N H\
- c ,/R’
R2
BF,Q
(4c)
f4b)
R
-
Soft bases., X.. react according
- to route (e)
. , with addition at
the terminal nitrogen atom of the azido group of ( 4 c ) ,
secondary reactions often occurring at the same time.
1. Addition of azide ions.
Cc=..
Y
+
R
(16)
Lecture at Freiburg, November 13, 1969 [VB 218 IEI
German version: Angew. Chem. 82, 86 (1970)
[*I Prof. Dr. H. Balli
2. Addition of heterocyclic ylides such as (8) o r ( 9 ) ; synthesis of triazatrimethinecyanines (10)[31.
Institut fur Farbenchemie der Universitat
CH-4056 Basel, S t . Johannsvorstadt 10/12 (Switzerland)
[I] H. Balli and F. Kersting, Liebigs Ann. Chem. 647, 1 (1961).
[ 2 ] G. Henseke and G Hanisch, Liebigs Ann. Chem. 643, 184
(1961); H. Quast, Dissertation, Universitat Marburg 1963.
[3] H. Balli and F. Kersting, Liebigs Ann. Chem. 663, 96 (1963).
141 S. Hiinig, H. Balli, and H . Quast, Angew. Chem. 74, 28
(1962); Angew. Chem. internat. Edit. I, 47 (1962).
[5] H. Balii and V . Miiller, Angew. Chem. 76, 573 (1964); Angew. Chem. internat. Edit. 3, 644 (1964); H . Bolli and R . Gipp,
Liebigs Ann. Chem. 699, 133 (1966).
Dissolution of Bituminous Coals at Temperatures
below 200°C
By G . Kolling[*I
3. Addition of heterocyclic hydrazines (11) with subsequent
oxidation to pentaazapentamethinecyanines (12) 141.
Q=N-.;N
I
R
-N-N=
I
H
N
I
NO
R
R
I
BF,Q
I
R
(12)
4. Addition of anions of reactive methylene compounds (13)
o r hydroxyaromatic compounds involving diazo group or
azo group transfer (synthesis of diazo compounds and azo
dyes) [51. ExampIes for (14) are diazomeldrum acid (yield
46 %), 4-diazo-3-methyl-l-phenyl-5-pyrazolone
(96 %), 2,4,6tris(diazo)-l,3,5-~yclohexanetrione(95 %).
Angew. Chem. internat. Edit.
1 Vol. 9
(1970)
No. I
Bituminous coals are scarcely soluble in most solvents at
temperatures below 200 O C ; however, in “specific” solvents
such as phenols, pyridine bases, and a few arnines, their
solubility can be as high as 40 %.
After alkylation with alkyl chlorides and AICl3 at 50 O C , o r
with olefins, HF, and BF3 at 80°C the solubility increases
still further. Even more efficient is acylation with higher fatty
acids and AlC13 at 50 O C , a treatment which makes mediumrank coals soluble but for their inert constituents.
The carbon matter pretreated in this way can easily be
further investigated. The average molecular weight is found
to be about 3000 after deduction of the alkyl groups introduced. Similar values have been reported by van Krevelen
and his co-workers as a result of a n extrapolation of the
average molecular weights which they had found by studies
o n partial extracts.
Lecture at Mulheim/Ruhr, November 27, 1969
[VB 219 IE]
German version: Angew. Chem. 82, 87 (1970)
I*] Prof. Dr. G. Kolling
Bergbau-Forschung G.m.b.H.
43 Essen-Kray, Frillendorfer Strasse 351 (Germany)
[l] H . N . M . Dormans and D.W. van Krevelen, Fuel 39,213 (1960).
81
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