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Патент USA US2109833

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2,109,833
‘ Patented Mar. 1, 1938
UNITED STATES
PATENT‘ ‘QF‘FICE
2,109,833
NEW COMPOUNDS OF THE BENZOFLUOR
ANTHENE‘ SERIES
m
.
‘
’
v
Werner-.~Zerweck.-and.,Karl Schiitz, Frankfort-on
_the¥Main=Fechenh‘eim, Germany, assignorsto
. -
vGnmeral “Aniline Works, Inc., New York, N. 'Y.,
' *acorporationof Delaware
1N0 ,Drawing. ‘Application June 24, 1936, Serial
No. 87,012. -.In.»Germany June 29, 1935
(Cl. 260-168‘)
v
3 Claims.
Our present invention relates to new com
that our invention is not'limited to the particu
pounds of the benzo?uoranthene series, more_ lar products nor reaction conditions mentioned
therein.
particularly to those'of the general formula:
Example 1
'
X
21.6 parts of 9-(oechlorobenzal) —?uorene of 70°. '
melting point, obtained by condensing ?uorene
,
‘X
with o-chlorobenzaldehyde, are mixed with 108
parts of caustic potash and about 140 parts of
quinoline and the mixture is heated to boiling 10
110’
for about 2 to 3 hours in an apparatus provided
With a re?ux condenser andva stirrer. Then the
mass'is poured on ice and hydrochloric acid, the
precipitate formed .is ?ltered off and recrystal
.15
wherein one ‘pair-of PX’s on adjoining carbon
atoms standsiiforlalmember selected from the
group consisting of two hydrogen atoms and a
radiole of the formula: —-CH=CH—CH=CH——,
lized if necessary with addition of animal char 15
coal from glacial acetic acid or benzine. The
new compound of the formula:
and the other pair of X’s stands for two hydrogen
20
20
atoms.
The new compounds are obtained by splitting
o?” hydrogen halide from a compound of the
general formula:
25
X
\C/
X
Hal
forms colorless needles of 167° melting point.
Instead of the quinoline there may be employed
other high-boiling bases such as for example di
30
30
methylaniline, dimethyltoluidine etc.
The same new product is obtained by start
ing from 9-(o-chlorobenzyl) -f1uorene of 77°
wherein the X’s have the above said signi?cation,
or by splitting off hydrogen halide and two hy
drogen atoms from a compound of the general
formula:
melting point, prepared by condensing ?uorene
with o-chloro-benzyl-alcohol.
Example 2
By treating 9-(o-ch1orobenzal)-2.3-benzo?uo
rene (which is prepared by condensing 2.3-benzo
?uorene with o-chlorobenzaldehyde) as described 40
in Example 1, a new hydrocarbon compound of
40
the general formula:
Hal
45
45
wherein the X’s have the above said signi?cation.
The new compounds may be used as intermedi
ates for the production of dyestuffs.
In order to further illustrate our invention the
following examples are given, the parts being by
weight and all temperatures in degrees centi
55 grade. However, we wish it to be understood
50
is obtained, which crystallizes in colorless needles
of 230-231” melting point.
55
2,109,833
We claim:
1. Compounds of the benzo?uoranthene series
of the general formula:
X
2. The 3.4-benzo?uoranthene of the formula:
X
10
which crystallizes in colorless needles of 167°
melting point and may be used as intermediates
for the production of dyestuffs.
15
wherein one
3. A dibenzo?uoranthene obtainable by treat
ing 9-(o-chlorobenzal)-2.3-benzo?uorene of the
formula:
20
is a, member of the class of
25
/
/ \/
W
H 01
H
_.
20
25
and the other
\ ——X \C——H
30
H
is ll
0-):
/
C—H
/
which new benzofluoranthene compounds may be
used as intermediates for the production of dye
35 stuffs.
with agents suitable for splitting o?f hydrogen
halide, which dibenzo?uoranthene crystallizes in 30
colorless needles of 230—231° C. melting point
and may be used as intermediate for the produc
tion of new dyestuifs.
WERNER ZERWECK.
KARL SCHUTZ.
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