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Патент USA US3041392

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ICQ
3,041,382
Patented June 215, 1962
2
3° C. and then continued ‘for two hours at room tem
3,041,382
perature. The solution was then ?ltered and the ?ltrate
extracted with ether. The ether extracts were dried and
the ether distilled o? under reduced pressure leaving
METHOD OF PREPG 2,2,4,4-TETRANITRO-1,5
PENTANEDIOL
Karl Klager, Monrovia, and John Paul Kispersky, Azusa,
Calif., assignors to Aerojet-General Corporation, Azusa, 5
Calif., a corporation of Ohio
behind an oil which soon crystallized. The mush mix
ture weighed 9.3 gm.
\
No Drawing. Filed May 29, 1957, Ser. No. 662,550
9 Claims. (Cl. 260-635)
This application is a continuation-in-part of our co
pending U.S. patent application Ser. No. 371,150, ?led
July 29, 1953, now abandoned.
97—99° C. Evaporation of the ?ltrate to 15 ml. with
chilling produced an additional 1.1 gm. of somewhat less
10 pure material. Total yield was 33% of the theoretical
yield.
2,2,4,4-tetranitro-l,S-pentanediol can be prepared con
veniently according to either of the general reaction 1
schemes set forth below wherein M is an alkali or alka 15
line earth metal or ammonia.
Preparation 1
Recrystallization from 150 ml.
chloroform yielded 3.0 gm. of pure diol, melting point
In the preparation of the diol, any salt of the alkali
metal or alkaline earth metal salts such as sodium, po
tassium, lithium, cesium, magnesium, calcium, etc., as
well as the ammonium salts are found to be suitable.
Potassium is the preferred salt due to its solubility char
acteristics which permit greater ease in separation of the
product from the reaction mass. The reaction proceeds
in accordance with Example I, differing only in the selec
20 tion of the starting material.
Similarly when the starting material utilized is the di
salt 'of tetranitropropane, the reaction proceeds in the
manner described in Example I, except that two equiva
lents of formaldehyde are added in place of one in order
to effect complete alcoholation.
_
The mono-salt of 2,2,4,4-tetranitrobutauol is reacted
with one equivalent of formaldehyde in acid media to
The starting materials can be conveniently prepared
according to the methods disclosed in assignees’ copend
yield the tetranitropentanediol.
ing application No. 371,149, ?led July 29, 1953, now
abandoned.
Preparation II
No.
ll
No, —~
11
201120
o—orr,-o
2(M+) F
‘
We claim:
No,
|
No,
|
HO CHr-—C—CHr—C——CHiOH
1. The method ‘of preparing 2,2,4,4-tetranitro-1,5
pentanediol which comprises reacting a compound
selected from the group consisting of alkaline earth metal,
No,
N03
N02
alkali metal, and ammonium salts of 2,2,4,4-tetranitro—
The di-salt of tetranitropropane is reacted with two 35 'butanol
and di-alkaline earth metal, di-alkali metal, and
equivalents of formaldehyde in acid media to yield the
di-ammonium
salts of 1,il,3,3-tetranitropropane with a
tetranitropentanediol.
member of the group consisting of formaldehyde and
No2
2,2,4,4-tetranitro-1,S-pentanediol readily reacts with
formalin in acid media and subsequently recovering
nitro-substituted amines, such as 3,3,3-trinitropropyl
2,2,4,4-tetranitro-1,5-pentanediol.
40
amine, to form nitroalkyl substituted tetranitropiperidine
K 2. The method of preparing 2,2,4,4-tetranitropentane
compounds as disclosed in assignees, copending U.S.
diol which comprises reaction an alkali metal salt of 2,2,
patent application Ser. No. 628,949, ?led December 12,
4,4-tetranitrobutanol
with formaldehyde in acid media,
1956, now U.S. Patent No. 2,978,453.
and
subsequently
recovering
2,2,4,4-tetranitro-1,5-pen
The nitropiperidine compounds thus prepared are ex
cellent high explosives, and can be used in any conven
tional explosive missile, projectile, rocket, or the like, as
the main explosive charge. An example of such a missile
is disclosed in U.S. Patent No. 2,470,162, issued May
45 tanediol.
3. The method of preparing 2,2,4,4-tetranitro-1,5-pen
tanediol which comprises reacting an alkaline earth metal
salt of 2,2,4,4-tetranitrobutanol with formaldehyde in
media and subsequently recovering 2,2,4,4-tetranitro
17, 1949. One way of using the nitro piperidine high 50 acid
1,5-pentanediol.
explosives in a device such as that disclosed in U.S.
4. The method of preparing 2,2,4,4-tetranitro-1,5-pen
Patent No. 2,470,162, is to pack the crystalline explosive
tanediol which comprises reacting a di-alkali metal salt
in powder form into the warhead of the missile. Alter
of l,1,3,3-tetranitropropane with formaldehyde in acid
natively, the crystals can be ?rst pelletized and then
and subsequently recovering 2,2,4,4-tetranitro-1,5
packed. A charge thus prepared is sufficiently insensi 55 media
pentanediol.
tive to withstand the shock entailed in the ejection of a
shell from a gun barrel or from a rocket launching tube
under the pressure developed from ignition of a propel
5. The method of preparing 2,2,4,4-tetranitro-1,5-pen
tanediol which comprises reacting a di-alkaline earth
‘metal salt of l,1,3,3-tetranitropropane with formaldehyde
lant charge, and can be caused to explode on operation
in acid media and subsequently recovering 2,2,4,4-tetra
of an impact- or time-fuse mechanism ?ring a detonat
60 nitro-1,5-pentanediol.
ing explosive such as lead azide or mercury fulminate.
6. A method of preparing 2,2,4,4-tetranitro-1,5-pen
tanediol which comprises reacting the potassium salt of
2,2,4,4-tetrauitrobutanol with one equivalent of formalde
ly as a means of illustration and does not in any way
hyde in acid media and subsequently recovering 2,2,4,4
de?ne either the limits or the scope of our invention.
65 tetranitro-1,5-pentanediol.
EXAMPLE I.—PREPARATION OF 2,2,4,4-'
7. A method of preparing 2,2,4,4-tetranitro-1,5-pen
TETRANITRO-LEi-PENTANEDIOL
tanediol which comprises reacting the ammonium salt of
16 grams (0.0438 M.) of damp potassium 2,2,4,4
2,2,4,4-tetranitrobutanol with one equivalent of formal
tetranitrobutanol were placed in a 300 ml. ?ask with
dehyde in acid media and subsequently recovering 2,2,
The following example is provided to more clearly
illustrate our invention. This example is presented pure
109 ml. of distilled water in 3.75 ml. (0.0505 M.) of
formalin. The mixture was then cooled to 3° C. and
13 ml. of 30% sulphuric acid were added dropwise with
stirring. The stirring was continued for 30 minutes at
70 4,4-tetranitro-1,5-pentanediol.
'8. A method of preparing 2,2,4,4-tetranitro-1,5-pen
tanediol which comprises reacting the di~potassium salt
of l,1,3,3-tetranitropropane with two equivalents of form
3,041,382
'
.
~
.3
4
aldehyde in.:acid media and subsequently reeovering 2,2,
References Cited in the ?le of this patent
4,4-tetranitro-1,5-pentanediol.
v
9. A method of preparing 2,2,4,4-tetranitro-l,5,~pen-
UNITE
tanediol which comprises reacting the di-ammdnium ‘salt’
25227959 '
D
‘
STATES PATENTS
Plant —————————————— -— SePt- 19’ 1950
ofv1,1,3,3-tetranitropropane with two equivalents of form- 5
aldehyde in acid media and subsequently recovering 2,2,
4,4-tetranitro<1,5-pentanediol.
V
‘
‘
138,456
FOREIGN PATENTS
Sweden ____________ __ Dec. 23, 1952
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