5271 5275.output

* GB785678 (A)
Description: GB785678 (A) ? 1957-10-30
Improvements in or relating to riveting machines
Description of GB785678 (A)
PATENT SPECIFICATION
785,678 Date of Application and filing Complete Specification Jan 19,
1956.
No 1 851156.
Application made in Switzerland on May 25, 1955.
Complete Speciflication Published Oct 30, 1957.
Index at Acceptance:-Classes 35, A 1 82 (A: J: K); 83 ( 4), H 4 N,
UI(C: F: J K: N), U 2 (A: D: J); and 124, C( 1 A 2: 4 X: 5 A 5: 9 D:
19).
International Classification: -023 j H 02 k.
CO Ml KPLETE SPECIFICATION
Improvements in or relating to Riveting Machines Wle, _d AG A G, a
Swiss body corporate of 14, L _giao n, Zuich, Switzerland, do licieby
declare 'he invention, for which we pray that a patent may be granted
to us, and the method oy which it is to be performed, to be
particularly described in and by the following statement: -
The invention relates to a riveting machine and aims to provide an
improved machine of dtis kind having a higher efficiency and which is
easier to operate than known machines and the electric control
elements of which are well protected from vibrations inherent in a
riveting machine.
According to the invention, the riveting machine comprises a riveting
tool which can be rotated by a motor and vibrated by an electro
magnetic vibrator, and electric control means for varying the
amplitude and period of the vibrations of the vibrator, the motor,
vibrator and tool being mounted as a unit for sliding movement in a
housing relatively to a worktable.
An example of the invention is described with reference to the
accompanying drawings in which:Fig 1 is a perspective view of a
riveting machine according to the invention, Fig 2 is a sectional side

elevation of the machine taken along the lines II-II in Fig 1, Fig 3
is g sectional elevation along the lines III-III in Fig 2 Fig 4 is an
enlarged sectional elevation of the electromagnetic vibrator for the
riveting tool of the machine, and Fig 5 is a diagram of the electric
circuit used with the riveting machine.
Referring to the drawings, the riveting machine is supported on a
platform 1 and comprises a work table or base la having an upstanding
hollow column 2 of substantially cylindrical shape A screw-threaded
spindle 3 is rotably mounted within the column 2 and carries a gear 4
at one end.
The screw-threaded portion of the spindle 3 engages the internal screw
thread of a nut 5 having a pin 6 which projects through a slot lPrice
3 s 6 d l 7 in the wall of -he column 2 and which is attached to a
housing 8 The housing 8 has a sleeve which is adapted to slide on the
column 50 2 when the spindle 3 is rotated A carriage 9 is slidably
mounted within a box shaped portion 80 of the housing 8 and attached
to a casing 10 of an electromagnetic vibrator and a casing 11 of an
electric motor The unit com 55 prising the components 9, 10 and 11 is
rigidly connected by an arm 12 to a nut 13, the internal screw thread
of which is engaged by the external screw thread on a hollow spindle
14, which is rotatably mounted in the column 2 60 parallel to the
spindle 3 and adapted to be moved longitudinally of the column The
hollow spindle 14 is provided with a pair of diametrically opposed
slots 15 accommodating a transverse pin 17 which serves as a dog and
65 extends radially outwards from a shaft 16.
Between the pin 17 and one end of the hollow spindle 14 a tension
spring 118 is connected and the end of the shaft 16 remote from the
pin 17 carries a gear 18 70 The two gears 4 and 18 can be rotated by a
common pinion 19 attached to the shaft of a hand wheel 20 whereby the
two nuts 5 and 13 are moved at equal speeds longitudinally of the
column, the screw threads or the spindles 75 3 and 14 having the same
helical pitch The hollow spindle 14 can also be moved longitudinally
by depressing a pedal 21 against the action of the spring 118, whereby
the unit consisting of the components 9, 10, 11, 12 and 13 80 is moved
relative to the housing 8 A further spring 22 arranged between the box
shaped portion 80 of the housing 8 and the vibrator casing 10 assists
the action of the spring 118.
Referring in particular to Fig 4, the virba 85 tor casing 10 is
substantially cylindrical and is made of ferromagnetic material It
contains a concentrically arranged inner cyli Uder 100 of
ferromagnetic material and the two cyinders are connected to one
another by a base 101 for 90 the cylinder 100 also made of
ferromagnetic material Into one end of the cylinder 100 there is
threaded a ferromagnetic hollow plug 102 for supporting a bushing 103

The other 785,678 a c' Ui' i 00 carri-s an enternally vre-;a ineaded
Aplug 1 > which ike; 7 ise serves to aufpart a buslig 105.
E tfeon the plugs 102 and 104 there is arranged a cozl spiing iu 6, a
fibiddie portion of;Vnicri is c Onn Scc a by a transverse bridge 107
to a percussion incinoer oi vibrator ro;d l 103, Liici S is noun Lted
for scing rmlvement axially of die vibcatior casing -1 u- The rod 108
at one of its cilds carries a cajA 1 G 9 of ferromagnetic na-eral,
iich oveillaps the adjacent end of th&e Casn G A cylindrical solenoid
-viincng Sp inserted between the cylinders 12 and 10 G viicn e byited
ay a cu:rernt inlduces a Ii magnetic fcil in an ar gap 11 G t O ineans
of which the cap i G 9 and th vibiator rod 108 a 1 C ur,,-i da' n The
lacaine is adapted to operate at 5 J or 10 z cycles per second, at 5 G
cycis being ouprated by means of a rectifier, and at 103 cycles by
means of condensers.
A shaft 111 is rotatably and siidabiy omoilted in a ead casing
attached to base 101.
A pulley 1121 ixed on the shaft 111 can be i Len h Y a te It 113 froem
a pulley 115 on the outp Ut 51 atit o' an electric motor 114 within t
Lie tno Lo casing 11.
A lpi 1 ' i 6 e erts a force to influence tne S 1 aat 1 11 away fomn
the;vidrator rod 108.
The sai 111 carries a riveting head or tool 117.
WI-en a woiiepicce W Fig 2) is to be ri-v tz Lu it is placed oi a
support 23 on the base la and the housinpg 3 is low,ezed by turning
the handvhleei 20 until the riveting head 117 is a predetenirinz a
distance from the workpiece v V Foot pressure exerted on the pedal 21
suffices to mnove the -vibrator casing 1 G and its associated parts
towards nhe;jorlpiece agnst the action of springs 22 and 118 until the
riveting head touches the;vorilpecee and then against t 1 e action of
the spring 116 until the vibrator rod 103 abuts aggainst the rotating
shaft 111 and imparts its vibrations th Lrouagh this shaft to the
riveting head 117.
The leature thai the riveting head 117 is vi'brated as well as rotated
results in improved riveting.
Referring to the wiring diagram in Fig 5 %C a feeder circet for the
solenoid -tvinding Sp includes a rectificr GR and a variable resistor
P 2 for adjusting the current intensity as well as a control switch K
governed by a time control ilt T A tdyrathron circuit arrangement is
used for the time control un-t T vwhich is controllable by adjustment
of a potentiometer P, and having a relay Rlls which is associated with
the swvitchn K In order to energize the time control unit TT, two
parallel connected double pole switches S and S, are closed The switch
S can be operated by hand at H while the switch S, is coupled to the
pedal 21 A double pole main switch S, when closed causes a transformer

Ue for the time control unit and the wvinding Sp, and also the motor
114 to be 6 i energised A signal lamp L, indicates whether the main
switch S, is closed, and a tabie il,mina, ng lamp L can be switched
or, by clesing a switch S,.
The machine is prepel 1 for o, zation by 7 C closing the inain stritch
S, The period of vibration desirei can be adjusted by r ?uia, ing the
potentometer P,,, tle ibrator ou-tzput can be' adjusted bj mneans o
the resistor P, When the rotat ig r;;eti mol 11 75 has bzzn oreou- Lt
inio c'-Iltact with the workp,_ce X, tihe sr 'a S, can be cles d by
coinpletely depressin g th_ pedal 21, so that the -;.nciing Sir is
sapl ed ith a t nat-ng current until the relay of torf control unit 8
C o Wens the switch K.
In orde that the electric control clements are not influenced by 7
vibrations, thes;y are built into a control cas ng S (Fig jj mounted
separatel l Oln Lt platform 1 bs-yond the effec 85 tive ranmge of the
vibrator.
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* GB785679 (A)
Description: GB785679 (A) ? 1957-10-30
Jet mill
1785,679 Date of Application and filing Complete Specification: Aug
13, 1956.
I)1 a ge No 24694156.
Complete Specification Published: Oct 30, 1957.
Index at acceptance:-Class 59, A 7 (D: F: G: M).

International Classif ication:-BO 2 d.
COMPLETE SPECIFICATION
Jet Mill I, CONRAD MARIUS TROST, a Citizen of the United States of
America, residing at 334 Newbold Avenue, Moorestown, New Jersey,
United States of America, do hereby declare the invention, for which I
pray that a patent may be granted to me, and the method by which it is
to be performed, to be particularly described in and by the following
statement: -
This invention refers to a fluid jet mill for comminuting dry
materials and is a development of that disclosed in my Patent
Specification No 765,257.
In applying the mill of my said Patent Specification to certain uses,
particularly to the grinding of coal on board a railway locomotive, it
has been found necessary to provide a specific form thereof which is
capable of being accommodated within a relatively small space and yet
providing substantially undiminished grinding and classifying capacity
Accordingly, certain modifications in the structure disclosed in said
co-pending application were necessary and it is the purpose of the
present invention to provide such modifications.
Therefore, a primary object of the invention is to provide a device
for grinding dry solid material, particularly bituminous coal, which
is sufficiently compact to be capable of being received into a
relatively small space.
A further object of the invention is to provide a device, as
aforesaid, which has a high degree of grinding capacity and which is
particularly adaptable to bituminous coal, or similar materials.
aforesaid, in which the back pressures arising in the classification
zone and also arising in the discharge from the mill may be relatively
high with respect to the pressure under which the material is fed into
the grinding chamber without materially injuring either the capacity
of the mill or its efficiency in classification.
A further object of the invention is to prolPrice 3 s 6 d l vide a
device, as aforesaid, which can be readily modified to utilise either
anvil grinding or jet grinding.
A further object of the invention is to pro 50 vide a device, as
aforesaid, which will be sturdy and free from high maintenance
requirements.
aforesaid, which has no 55 moving parts.
aforesaid, wherein the classification of ground material will be
attained with a high degree of accuracy 60 Other objects and purposes
of the invention will be apparent to persons acquainted with apparatus

of this general sort upon a reading of the following disclosure and
inspection of the accompanying drawings 65 In the accompanying
drawings:
Figure 1 is a view of a preferred form of the apparatus shown in
central, vertical cross-section.
Figure 2 is an enlarged sectional view 70 taken along the line II-II
of Figure 1.
Figure 3 is a fragmentary, sectional view similar to Figure 1 but
showing a modification of the invention.
Figure 4 is an enlarged section taken on 75 the line IV-IV of Figure
1:
Figure 5 is a horizontal sectional view showing a further
modification.
Referring now to the drawings in detail, there is shown in Figure 1 an
elongated cas 80 ing, or grinding housing, 1, the same being of either
cylindrical or rectangular cross-section, having an anvil 2, located
at and closing one end thereof and a plug 3 located at the other end
of said casing Said anvil 2 is held 85 in position by any convenient
means, as the set screw 4 Plug 3 is held in position by any convenient
means, as the set screw 6.
A conduit 7 terminating in a nozzle 8 extends through the plug 3 from
a point exter 90 nally of the apparatus and is operatively associated
with a feeding device 5, as a hopper Said conduit 7 may be connected
to any convenient source of grinding fluid under pressure, such as
either compressed air or steam A block 9 is positioned within the
casing 1 intermediate the nozzle 8 and the anvil 2 and is normally
somewhat closer to said nozzle An internal venturi passageway 11,
having a flared entry end 12, is provided through said block 9
co-axial with the said nozzle 8 and with the casing 1.
An off-take conduit 13, of cross section preferably as shown in Figure
4, extends upwardly from the opening 15 in the casing 1 at a point
therein intermediate the block 9 and the anvil 2 In the particular
embodiment of the invention here shown, said offtake conduit is
substantially adjacent the discharge end of said venturi passageway 11
in said block 9, and somewhat spaced from the face of the anvil 2, but
this may vary according to the kind of material being handled.
A first orienting conduit 14 is placed above said off-take conduit 13
and connected thereto by flanges 17 and 20 in a known manner Said
first orienting conduit curves rather sharply, as about 90 degrees, in
a direction away from the nozzle and is connected to a second
orienting conduit 16 by flanges 18 and 25 Said second orienting
conduit curves, as about 90 degrees, in a direction away from the
grinding chamber 10 and provides, in combination with the conduit 14,
an offset and reverse curve A classifying section 19 is substantially

semi-circular and is connected to the second orienting conduit 16 by
the flanges 21 and 22 Said classifying conduit 19 may be of a variety
of cross-sectional shapes, including circular, elliptical and
trapezoidal, as set forth in detail in my aforesaid Patent
Specification, but is preferably circular or elliptical Said
classifying conduit has a discharge opening 23 which communicates
through a discharge conduit 26, having an entry throat 24, with any
desired point of use or storage of the material withdrawn from the
classifying conduit.
A return conduit 27, of substantially circular cross-section, is
connected at one end to the classifying conduit 19 by the flanges 28
and 29 The other end of said return conduit 27 is connected to the
casing 1 and communicates with the interior of the chamber 32 through
a return opening 31, located between the plug 3 and the block 9 The
return conduit 27 may be straight, as shown.
In Figure 3 there is shown a modification of the device in which the
anvil 2 is replaced by a plug 36 through which extends a conduit and
nozzle assemblage 37 which is placed in opposing, co-axial,
relationship with the nozzle 8 In all other respects this apparatus is
the same as that described in connection with Figures 1, 2 and 4.
In Figure 5 there is illustrated a further modification in which an
anvil 41 is placed within the grinding chamber 10 substantially under
the off-take conduit whose opening 15 is indicated by broken lines in
said Figure 5 70 Fluid conducting conduits 42 and 43, for delivering
high velocity jets, are added to the structure of Figure 3 and each of
these jets, together with the main grinding and feeding conduit 7,
direct streams of grinding fluid 75 against the sides of the anvil 41
Partially comminuted material to be ground may be fed through any or
all of the conduits 37, 42 and 43 in addition to the feeding thereof
through the conduit 7 or, in instances where 80 the material is of
maximum grinding diffilculty, it may be fed into the device only
through either or both of the conduits 7 and 37, and the auxiliary
jets will function to drive material circulating through the grind 85
ing chamber 10 against the several faces of the anvil 41 Other parts
of the device shown in Figure 5 are the same as those shown in
connection with Figures 1, 2 and 4, and are numbered correspondingly
Likewise, the 90 device discharges through a discharge opening 15 and
through classification means the same as shown in Figure 1 and
returned material re-enters the device for further grinding through
the return opening 31 95 OPERATION.
A mixture of partially comminuted material, as bituminous coal, with a
grinding fluid, as steam or air, is introduced into the device from
the conduit 7 through the nozzle 100 8 It passes through the venturi
passageway 11 and is driven at a high velocity against the face of the

anvil 2 The material is largely shattered and that which is
sufficiently fine to be carried by the fluid stream passes out 105 of
the grinding chamber 10 through the opening 15 into the first
orienting conduit 14 The reverse turn in the conduits 14 and 16
provides an initial classifying action in that the coarser material
will partially sepa 110 rate in each turn from the finer material and
thus will tend to gather on the radially outermost wall of the
classifying section 19 somewhat more quickly than is possible in
previously known devices Thus, the use of the 115 reversely curved
conduit enables the classifying chamber to be materially smaller than
in those cases where the curve is all in one direction As the material
moves through the classifying chamber 19, the coarser por 120 tion
thereof continues to gather at the radially outermost wall so that by
the time a given portion thereof reaches the zone adjacent the outlet
opening 23, only the finer materials within a predetermined classifica
125 tion size range are adjacent the radially inner wall of the
classification chamber Inasmuch as the return conduit 27 is of
somewhat smaller cross-sectional area than that of the classification
chamber 19, that portion of the 130 785,679 thereof If desired,
further supplies of solid material may be introduced through one or
more of the conduits 37, 42 and 43 Alternatively, the material may be
introduced only through conduits 37, 42 and 43 and jet 8 left 70 free
to carry only the return load from return conduit 27 This will be
somewhat more efficient in those cases where there is a high volume of
recirculating material.
Such multiple introduction of material may 75 be used in a wide number
of cases and will be particularly useful in those instances where the
material shatters relatively easily but it is not possible for any one
jet to carry as high a load of material as the classifying 80 chamber
can handle.
in all three forms of the mill here shown, the grinding chamber is
kept relatively short so that the material introduced thereinto
through the nozzle 8 strikes either the anvil 85 or the opposing jet
with a maximum of force.
Thus, it is possible to utilise a relatively low energy input with a
maximum of efficiency and the effectiveness of the grinding does not
seriously suffer The reverse bend in the con 90 duit leading to the
classification chamber effects certain preliminary classification so
that the total conduit length from the opening 15 to the opening 31
may be kept at a minimum This effects further savings in 95 energy and
space requirements, without permitting classification effectiveness to
be materially diminished Thus, the objects and purposes above set
forth have been accomplished 100 While certain specific embodiments of
the invention have been set forth in detail for illustrative purposes,

it will be recognised by those skilled in the art that various other
modifications may be made without depar 105 ture from the principles
of the invention, and hence the appended claims are to be interpreted
as including such variations excepting as such claims may by their own
terms expressly limit otherwise 110 Having regard to the provisions of
Section 9 of the Patents Act attention is directed to the claims of
Patent No 765,257.
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* GB785680 (A)
Description: GB785680 (A) ? 1957-10-30
Improvements in and relating to self-centering or aligning rollers
COMPLETE SPECIFiCATION
Improvements in and relating to Self-Centering or Aligning Rollers
We, UNITED STATES STEEL CORPORATION, a Corporation organized and
existing under the laws of the State of New Jersey, United Stashes of
America, doing business at 525,
William Penn Place, Pittsburgh 3O, State of
Pennsylvania, United States of America, do hereby declare the
invention, for which we pray that a patent may be granted to us, and
the method by which it is to be performed, to be particularly
described in and by the following statement:
This invention relates to self-centering or aligning rollers for
aligning travelling strip material with respect to a predetermined
path of travel normal to the rollers. Essentially the type of
apparatus with which the present invention is concerned, in its
fullest embodiment, involves at least one roller of the selfcentering

or aligning type, such roller extending generally transversely to the
intended path of travel of the strip and having two roller sections
one on each side of its transverse center, the two sections being
adapted to rotate in unison at the same peripheral speed when rotated
by external driving means or by frictional contact with the travelling
strip and being so adapted and arranged that they (the roller
sections), when acting against the travelling strip surface engaged by
he roller sections, produce a reactive force acting inwardly toward
the center of ke roller whereby the strip is centered or ,liJned with
respect to the desired path of travel Examples of such rollers and
their manner of operation are described in the specifications of our
prior United Kingdom patents 709.908 709,959, 713,557, 717,671,
719.088, 725,762, 730,594, 735,561 and 735,574 and for convenience in
the ensuing statement of invention and in Claim 1, the et pression "of
the type hereinbefore defined" is used to designate self-centering and
aligning rollers of that general type.
The present invention consists in a selfcentering or aligning roller
of the type hereinbefore defined adapted for aligning or centering a
travelling strip of a predetermined width, in which each section of
the roller comprises a cylindrical portion adjacent the transverse
center, a first conical portion adjacent said cylindrical portion
having a decreasing diameter away from the cylindrical portion, and a
second conical portion adjacent said first conical portion having an
increasing diameter away from said first conical portion, the maximum
diameter of said second conical portion being approximately the same
as the diameter of the cylindrical portion, the distance between the
junctions of the first and second conical portions on opposite sides
of the transverse center being no greater than the width of the strip
to be handled.
In order that it may be clearly understood and readily carried into
effect, the invention will now be described, by way of example, with
reference to the accompanying drawings, in which:
Figure 1 is a schematic plan view of an endless belt arrangement
utilizing the present invention;
Figure 2 is a side elevation of the arrangemelt shown in Figure 1, and
Figure 3 is a view taken on the line III-
III of Figure 2.
Referring now to the drawings, the travelling strip is here
represented by a belt (13) which passes around the self-centering or
aligning roller 4 and the rollers 5, 6 and 7.
The self-centering or aligning roller 4 is in this particular instance
mounted on a rigid
U-shaped yoke 8 which is pivotally mounted about a knife-edged pivot 9
at the bottom of each side arm of the yoke and a crosspiece 10

interconnects the yoke arms near their bottom ends. From the center of
the crosspiece 10 there extends an arm 11. Bolts 12 and 13 are
attached to the base 14 of the apparatus, the bolt 12 passes through
aligned holes on the crosspiece 10 and arm 11 and the bolt 13 extends
upwardly through a hole in the free end of the arm 11. A spring 15
surrounds the bolt 13 and is confined between the upper part of the
arm 11 and the nut 16 so that the arm 11 is biased downwardly at all
times to tension the belt (*.
The holes for the bolt 12 are slightly larger than the bolt to permit
a sight tilting of the yoke. if desired a counterweight can be
substituted for the spring 15.
The roller 4 is a self-centering roller of the general type disclosed
iii our prior British specification 717,671 but it has a specific
contour. This roller may be of the type shown in our prior British
specifications 709,908 or 735,561 both of which are of the general
type hereinbefore defined. Each half of the roller 4 has a cylindrical
section 17 adjacent the transverse center of the roller, a conical
section 18 adjacent thereto which decreases in diameter away from the
cylindrical portion and a conical section 19 adjacent the bearings 20
which increases in diameter away from its adjacent reversely tapered
conical section 18.
The width of the belt (B) is preferably slightly greater than the
distance between the smaller diameter outer ends of the conical
sections 18. The diameter of the cylindrical sections 17 is
approximately equal to the maximum diameters of the outer conical
sections 19, that is to say, it may be exactly equal to, slightly
greater or less in diameter than said sections. The amount of taper of
the conical sections is greatly exaggerated in the drawings for the
purpose of illustration and in most instances the difference in radius
is only a matter of a few thousandths of an inch.
In the arrangement shown the rollers 5 and 7 are cylindrical rollers
of the narrowbodied type so called because the actual strip engaging
surface is essentially narrower than the length of the rollers and the
width of the strip. The roller 6 may be either a roller of the
narrow-bodied type or a full bodied cylindrical roller having the
strip supporting surface extending the full length of the roller and
somewhat greater than the width of the strip.
The strip is subjected to treatment in the container 21 and any
convenient means may be provided for driving the strip;, for example,
ally one of the rollers may be driven or the strip itself may be
driven by contact with an external roller bearing on the surface of
the strip.
The arrangement particularly described and illustrated is particularly
suited for flex ible belts and the exact point of contact of the belt

on the roller 4 depends upon the tensicn applied vay the spring 15.
However, it will be seen thas the belt does not contact the center of
the roller and there is therefore no danger of the belt being nlarLed
by the separation of tile center of the roller sections.
What side claim is:
1. A self-centering or aligning roller of the type hereinbefore
defined adapted for aligning or centring a travelling strip of a
predetermined width, in which each section of the roller comprises a
cylindrical portion adjacent the transverse center, a first conical
portion adjacent said cylindrical portion having a decreasing diameter
away from the cylindrical portion, and a second conical portion
adjacent said first conical portion having an increasing diameter away
from said first conical portion. the maximum diameter of said second
conical portion being approximately the same as the diameter of the
cylindrical portion, the distance between the junctions of the first
and second conical portions on opposite sides of the transverse center
being no greater than the width of the strip to be handled.
2. An assembly of self-centering rollers for centering or aligning a
moving strip with respect to a predetermined path of travel normal to
the rollers, such assembly comprising a self-centering or aligning
roller according to Claim 1, and a second roller having a strip
supporting surface of less width than the predetermined width of the
strip.
3. An assembly of self-centering rollers for centering or aligning a
moving strip with respect to a predetermined path of travel normal to
the rollers, said assembly comprising a self-centering or aligning
roller according to Claim 1, and tiro rollers of the narrow-bodied
type, one engaging the strip before and the other after engagement
with said aligning roller.
4. An assembly according to Claim 2 or
Claim 3 wherein the arrangement and disposition of the rollers is sudi
that i!l its travel the strip engages a substantial arc of the
periphery of at least one of the rollers.
5. A self-centering or aligning roller substantially as described with
reference to the accompanying drawings.
6. An assembly substantially as described with reference to the
accompanying dra -. in.rs.
* GB785681 (A)
Description: GB785681 (A) ? 1957-11-06

Steroid compounds
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The EPO does not accept any responsibility for the accuracy of data
and information originating from other authorities than the EPO; in
particular, the EPO does not guarantee that they are complete,
up-to-date or fit for specific purposes.
PATENT SPECCIFICATION-
|gpi Date of Application and filing Complete Specification: Sept 16,
1953.
No 25642/53.
Application made in United States of America on Sept 17, 1952.
Complete Specification Published; Nov 6, 1957.
Index at acceptance: -Class 2 ( 3), U 4 (A 1: A 2: BI: C 3: C 5).
International Classification:-CO 7 c.
COMPLETE SPECIFICATION
Steroid Compounds We, MERCK & CO INC, a corporation duly organised and
existing under the laws of the State of New Jersey, United States of
America, of Raliway, New Jersey, United States of America, do hereby
declare the invention, for which we pray that a patent may be granted
to us, and the method by which it is to be performed, to be
particularly described in and by the following statement: -
This invention is concerned with novel cyclopentanopolyhydro
phenanthrene compounds and processes for preparing them.
In brief, this invention provides novel etienoylpyruvic acid compounds
having the formula:
CO 2 CO Cf CO co FORML/b / in which the 3-position is occupied either
by a divalent group convertible to keto by acid hydrolysis or by a
pair of univalent groups together convertible to a single keto group
by acid hydrolysis; and novel etienoylpyruvic acid compounds having
the formula:
FORMULA 9 in which the 3-position is occupied by a univalent group
which is convertible to keto by acid hydrolysis.
Examples of bivalent groups which may occupy the 3-position in the
compounds of lPrice 3 s 6 d l Formula I are cyclic ketal groups, e g

ethylenedioxy, ethylene dithioketal, and ethylene hemi 30 thioketal;
pairs of univalent groups which may occupy the 3-position in the
compounds of Formula I include non-cyclic ketals such as dimethyl
ketal; single univalent groups which may occupy the 3-position in the
compounds 35 of Formula II include enol ethers such as ethyl enol
ether The preferred group is the ethylenedioxy group, which gives a
compound of Formula II in which the 3-position has a " substituent 40
In the subsequent description for convenience and to avoid repetition,
reference will be made to the 3-ethylenaedioxy etienoylpyruvic acid
compounds, and to the 3-ethylenedioxy 20-keto-pregnenes from which
they are pre 45 pared It is to be understood, however, that the
reactions described for such compounds apply also to the analogous
compounds in which the 3-position of the molecule is substituted in
any of the ways mentioned 50 above in connection with the definition
of Formulae I and II, so that the compounds in question may have one
or two nuclear double bonds, depending on how the 3-position is
substituted, i e when the 3-substituent is a ketal 55 or cyclic ketal,
the compound will be a AW-ene and when it is an enol ether, the
compound will be a A 3 A 5-daene.
The function of this 3-substituent is to protect the 3-keto, group
from reactions such as 60 oxidation and addition, and the manner of
its introduction forms part of the invention claimed in our copending
Application No.
29358/55 (Serial No 763,208).
The novel compounds of the invention are 65 useful as starting
materials in the process described and claimed in the specification of
cur copending Application No 9553/56 (Serial No 785,683), the compound
forming the subject of that application being treated to form 70
derivatives of 1 l-dehydrocorticosterone by processes described and
claimed in the speci785681 fication of our copending Application No.
9554/56 (Serial No 785,684).
In accordance with the present invention, derivatives of 11-keto
progesterone in which the 3-keto substituent is blocked or protected
by a suitable radical convertible to keto by acid hydrolysis can be
converted to derivatives of etienoylpyruvic acid having the Formulh I
and II hereinbefore by reacting the 11-keto progesterone derivative
with an oxalic acid diester in the presence of a strong alkali The
said derivatives of 11-keto progesterone form part of the invention
claimed in the specification of our copending application No 7716/56
I(Serial No 777,691) and methods for their preparation are described
and claimed in the specifications of our copending applications
Nos 7716/56 and 9552/56 (Serial Nos.
777,691 and 777,693).
Thus, for example, 3-ethylenedioxy-11-keto progesterone, may be

reacted with an oxalic acid diester in the presence of a strong alkali
in a suitable inert medium to obtain 3-ethylsnedioxy-11-keto
etienoylpyruvic acid The d or dl-form of 3-tthylenedioxy-11-keto
progesteroane may be used In carrying out this reaction, it is usually
preferred to use an oxalic acid diester of a lower alkanol, such as
dimethyl oxalate or diethyl oxalate, since these esters are readily
and conveniently obtained.
Preferred strong alkalis are alkali metal alkoxides such as sodium
methoxide and potassium ethoxide although other strong alkalis, such
as sodamide, sodium hydride, and sodium triphenylmethyl, are also
suitable Inert organic solvents, such as benzene, toluene, xylene and
petroleum hydrocarbons are satisfactory for use as solvent mediums in
carrying out this reaction Thus the preparation of A4 o
3-ethylenedioxy-11-keto-etienoylpyruvic acid is most conveniently
effected by reacting the 3-ethylenedioxy derivative of l 1-keto
progesterone with dimerhyl oxalate in the presence of sodium methoxide
in a benzene medium.
The resulting mixture is permitted to stand at room temperature for
about 10-20 hours in order to complete the formation of the desired
etienoylpyruvic acid compound Upon completion of the reaction, the
mixture is cautiously acidified and the pyruvic acid compound can, be
readily recovered by extraction with a water-immiscible solvent such
as ether and evaporation of the solvent extracts.
The following example illustrates methods of carrying out the process
of the invention.
EXAMPLE.
A 5-3-Ethylenedioxy-11-Keto-Etienoylpyruvic Acid.
A mixture of 1 3 g of dry sodium methoxide, 3 0 g of dimethyl oxalate
and 2 50 g.
of the 3-ethylenedioxy derivative of d-11-keto progesterone was
dissolved in 20 cc of dry benzene The solution was permitted to stand
at room temperature for 20 hours, poured into ite waters and carefully
acidified with dilute sulphuric acid and excess sodium dihydrogen
phosphate The liberated organic product was dissolved in ether, and
the ethereal layer extracted with 55 cc of aqueous IN potassium
hydroxide After standing at room temperature for one hour, the
alkaline extract was cooled and acidified as before The liberated acid
was extracted twice with ether, the ethereal solution washed and
concentrated to dryness inz vacuo Crystallization of the residue from
ether yielded d-:1-3-ethylenedioxy-11keto-etienoylpyruvic acid, dec
180-182 ' C.
The above procedure was repeated using as starting material dl-S
-3-ethylenedioxy-11,20diketo-pregnene obtained by total synthesis.
The product, dl-L-3-ethiylenedicxy-11-ketoetienoylpyruvic acid, was

crystallized from ether (m p 174-7 C dec).
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* GB785682 (A)
Description: GB785682 (A) ? 1957-11-06
Steroid compounds
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The EPO does not accept any responsibility for the accuracy of data
and information originating from other authorities than the EPO; in
particular, the EPO does not guarantee that they are complete,
up-to-date or fit for specific purposes.
785 682 Date of Application and filing Complete Specification: Sept
21, 1953.
No 25992153.
Application made in United States of America on Sept 20, 1952.
Complete Specification Published: Nov 6, 1957.
Index at acceptance:-Class 2 ( 3), U 31 U 4 (A 1; A 2; B 1; C 4; CX).
International Classification:-CO 7 c, COMPLETE SPECIFICATION
Steroid Compounds; We, MERCK & CO INC, a corporation duly organised
and existing under the laws of the Stare of New Jersey, United States
of America, of Rahway, New Jersey, United States of America, do hereby
declare the invention, for which we pray that a patent may be granted
to us, and the method by which it is to be performed, to be

particularly described in and by the following statement:-
This invention is concerned with novel
cyclopentanopolyhydrophenanthene compounds and processes for preparing
them.
In brief, this invention provides novel 20-cyano-pregneneus compounds
having the formula:
and II R represents an acyloxy group.
Examples of bivalent groups which may occupy the 3-position in the
compounds of Formula I are cyclic ketal groups, e g ethylenedioxy,
ethylene dithioketal, and ethylene hemithiolketal; pairs of univalent
groups which may occupy the 3-position in the compounds of Formula I
include non-cyclic ketals such as dimethyl ketal; single univalent
groups which may occupy the 3-position in the consp'ounids of Formula
II include enel ethers such as ethyl enol ether The preferred groupi
is the ethylenedioxy group, which gives a compound of Formula II in
which the 3-position has a 3 6 Formula I in which the 3-position is
occupied either by a bivalent group, convertible to keto by acid
hydrolysis or by a pair of univalent groups together convertible to a
single keto groups by acid hydrolysis; and novel 20-cyano-pregnene
compounds having the formula Formula II in which the 3-position is
occupied by a univalent group' which is convertible to' keto by acid
hydrolysis In the foregoing Formulx I C,, O substituent.
C#2 -0 o In the subsequent description, for convenience and to, avoid
repetition, reference will be made to, the As-3-ethylenedioxy-1
l-keto20-cyano-20-hydroxy-21-acetoxy pregnene and 45 to the
A'-3-ethylenedioxy-11,20-diketo-21acetoxy-pregnene from which it is
prepared.
It is to' be understood, however, that the reactions described for
such compounds apply also, to the analogous compounds in which 50
there is a different 21-acyloxy group' and/or in which the 3-position
of the molecule is substituted in any of the ways mentioned above in
connection with, the definition of Formulas I and II, so that the
compounds in 55 question may have one or two' nuclear double bonds,
depending on how the 3-position is substituted, i e when the
3-substituent is a ketal or cyclic ketal, the compound will be a 5-ene
and when it is an enol ether, the Gcon 60 pound will be a A"' -diene.
The function of this 3-substituent is to protect the 3-keto, group
from, reactions such as oxidation and addition, and the manner of its
introductionb forms part of the invention 65 claimed in our copending
Application No 29358/55 (Serial No 763,208).
The novel compounds of the invention are useful as starting materials
in the process described and claimed in the specification of our
copending Application No 9817/56 (Serial No 785,685) the compound
forming the subject of that application being treated to form

cortisone esters by processes described and claimed in the
specification of our copending Application No 9818/56 (Serial No.
785,686).
The novel 3-ethylenedioxy compounds are prepared from steroid
compounds of formula CO, C Al in which R represents an acyloxy
substituent.
In this process, A'-3-ethylenedioxy-11,20diketc-21-acetoxypregnene is
converted to AW 3 -ethylenedioxy 11 -keto 20-cyano
20hydroxy-21-acetoxypregnene, by bringing a solution of the starting
material into intimate contact with hydrogen cyanide Solvents for the
starting material which are inert to the action of hydrogen cyanide,
such as hydrocarbons, halogenated hydrocarbons and ethers, are
suitable media for carrying out this reaction Generally, it is found
that it is desirable to add a small amount of an organic base such as
triethylamine to the reaction mixture to, obtain maximum yields,
although the reaction can also be carried out without the addition of
the organic base.
The following example illustrates a method of carrying out the
invention.
EXAMPLE.
Preparation of
A'-3-Ethylenedioxy-11-keto-20hydroxy-20-cyano-21-acetoxypregnene A
solution of 380 mg of
A'-3-ethylenedioxy-11,20-diketo-21-acetoxypregnene in 3 cc.
of ethylene dichloride was treated with 0 3 cc.
of liquid hydrogen cyanide and 0 05 cc of triethylamine After ten
niinutes, 3 0 cc of absolute ether was added The partially crystalline
mixture was treated with an additional 3 0 cc of ether after 1 hour At
the end of three hours, the product A'-3-ethylenedioxy 11 -keto 20
-hydroxy 20 -cyano 21acetoxypregnene, was filtered Recrystallization
from chloroform-ether gave the pure cyanhydrin, mnp 220-224 C (dec).
When the racemic mixture, dl-A'1-3-ethylenedioxy 11,20 -diketo 21
-acetoxypregnene, was reacted in the manner described above, d I-A
5-3-ethylenedioxy 11 -keto 20 -hydroxy20-cyano-21-acetoxypregnenel, mp
220-225 C (dec) was obtained.
which form part of the subject of our copending Application No 9554/56
(Serial No 15 785,684) by a process which can be represented
chemically as follows:
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