US1583314A - Process of obtaining alcohols, etc. - Google Patents
Process of obtaining alcohols, etc. Download PDFInfo
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- US1583314A US1583314A US461302A US46130221A US1583314A US 1583314 A US1583314 A US 1583314A US 461302 A US461302 A US 461302A US 46130221 A US46130221 A US 46130221A US 1583314 A US1583314 A US 1583314A
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- Prior art keywords
- alcohol
- water
- mixture
- constant boiling
- column
- Prior art date
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- 238000000034 method Methods 0.000 title description 22
- 150000001298 alcohols Chemical class 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 94
- 235000019441 ethanol Nutrition 0.000 description 65
- 239000000203 mixture Substances 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
- 239000007788 liquid Substances 0.000 description 41
- 238000009835 boiling Methods 0.000 description 40
- 150000002148 esters Chemical class 0.000 description 26
- 239000000470 constituent Substances 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- -1 benzol Chemical compound 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
Definitions
- My. invention relates particularly to a process designed for obtaining alcohols havence to the production of abso ute alcohol.
- the object of my invention is to provide 95%, and particularly absolute alcohol, may be obtained. 4
- A- further object is toobtain this end by distilling an alcohol with a second liquid, as, for example,water, and arthll'd constituent that is miscible with the alcohol but substantially immiscible with the second liqu d, as, for example, ethyl acetate, thus obtam ing a vapor mixture having d1fi'eren-t proportions of the constituents than the liquid being distilled and preferably so as-to obtain, as a result of the distillation, a constant boiling mixture of the three liquids and as well as an alcohol of a high strength.
- a second liquid as, for example,water
- arthll'd constituent that is miscible with the alcohol but substantially immiscible with the second liqu d, as, for example, ethyl acetate
- Another object is to provide such a proc-.
- a further object is to distill these- .two liquids separately in such a manner as to obtain from one of them the third constituent, as a residue, of substantially 100% strength as well as a condensate comprising said constant boiling mixture and from the other liquid a residue of water together with a condensate'of said constant boiling mixture.
- the object of my invention is to provide a continuous process in which the aforesaid distillations are conducted simul-' ing a high strength and has especial refer-- Application am April 14, 1921. swarm. 401302.
- Figure 1 is a diagrammatic representation of an apparatus used in accordance with my invention.
- Figure 2 is a vertical section of the measuring receptacle
- Figure 3 is a section of one of the columns.
- t e measuring receptacles 2 and 6 are comprised of a centoa tral inlet pi e 8 connected at the to feed- 1 near the top thereof a slot 13 to carry ofi' 7 approximately the overflow from the measuring receptacle and indicate by the height of-the outflowing liquidon a scale 14 at the edge of the slot 13 the rate of flow of the liquid from the measuring receptacle.
- the rates of flow of the water and the constant boiling solution are regulated so that the volumes of the two liquids fed during a given interval of time are substantially equal.
- the liquids pass into-a separating tank 15 where an upper layer 16 separates out containing by weight 93% ethyl acetate, 51/ water and 1.5% alcohol, and where a lower layer 17 is formed containing 8% ethyl acetate, 86% water, and 6% ethyl alcohol.
- the upper layer 16 is drawn off by a pipe 18, and is fed thereby into the side of a column 19 made up of a plurality of pans 20 carrying liquid which overflows from each pan to the next pan below by a series ofpipes 21, while the vapors are caused to pass through the bodies of liquid on the pans through liquid sealed bells 22 and pipes 23 leading into the same.
- Steam is provided for the column 19 by means of aheater 24 located at the bottom thereof comprising tube sheets 25 and26 carrying tubes 27 an supplied with heating steam by inlet and outlet pipe 28 and 29. From the base of this column there is a drawofi' pipe 30 for ethyl acetate having a strength of 100% which leads to a. sight glass 31 having a vent pipe 32leading back to the column 19, and
- the lower layer of liquid 17, is conducted by a pipe 46 to the side of a second collumn 47 constructed the same as the column 19, except that thereis aninlet pipe 48 at the bottom thereofzprovided with perforations to inject live steam instead of utilizi ing indirect heat.
- the steam thus injected maintains the lower end of the column 47 at a temperature of approximately 100 0.
- a discharge pipe 52 conveys away the condensed liquid which is approximately the constant boiling solution comprising 83% ethyl acetate, 8% water, and 9% alcohol to the tank 1.
- an outlet pipe 53 is provided for conveyingmwalyl the excess ethyl alcohol having substantia a 95% strength to the side of a third column 54.
- the col-' umn 54 is constructed the same as the column 19, except that in addition to the inlet pipe 53, there is an inlet pipe 54* com lower end of this column 54 is maintained 1l0 at a temperature of substantially 78 0,, and the top of the tower is maintained at a temperature of about 70 C. 'From the lower end of-this tower there is drawn off alcohol having a high strength, for example, 115
- I claim: q l 1. The process of eliminating a constltuent of a binary liquid mixture whose ingredients form a constant boiling mixture, comprising the addition thereto of a third liquid that forms a ternary constant boiling mixture with the. other two ingredients and thedistillation of the ternary mixture to evolve the ternary constant boiling mixture and leave as a residue the constituent of the the constituent to be eliminated; to the ten nary constant boiling distillate, and allowing liquid layers to separate out; distilling each layer -to evolve constant boiling mixtures and leave as residues liquids containing as principal constituents respectively the added liquid and the liquid desired to be re-- covered, and returning these residues to the original mixture undergoing distillation.
- the process of obtaining an absolute alcohol from an aqipeous alcohol which comprises: distilling t e latter with a substance miscible with the' alcohol but immiscible with water, to form a constant boiling mix ture of said substance, alcohol and water, and thereby obtaining an absolute alcohol as a residue; mixing'thesaid constant boiling mixture with water to formliquid layers; separately distilling each layer to evolve ternary constant boiling mixtures and to recover a substantial quantity of the said substance and "aqueous alcohol; and returning the said substance and aqueous alcohol to the first named aqueous alcohol.
- the process of obtaining absolute alcohol from aqueous ethyl alcohol which comprises: distilling the latter with ethyl acetate to form a constant boiling mixture of ester, alcohol and water and thereby obtaining absolute alcohol as a residue; mixing the said constant boiling mixture with water to form liquid layers; separately distilling each layer to recover a substantial quantity of the ester and aqueous alcohol; and returning the ester and alcohol to the ethyl alcohol undergoing distillation.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Description
May 4 ,"1926.
w. H. RODEBUSH I PROCESS O-F OBTAINING ALGQHOLS, ETC
2 Sheets-Sheet 1 Filed April 14, 1921 May 4 1-926.
W. H. RODEBUSH PROCESS OF OBTAINING ALCOHOLS, ETC
Filed April 14., 1921 2 Sheets-Sheet 2 Patented May 4, 1926.
' UNITED STATES PATENT eerie IE.
WORTH E.- LODEBUSH OI' mum-cannula, A88IGNOR TO U. BL INDUSTRIAL ALCOHOL 00., A CORPORATION OF WEST VIRGINIA.
rnocnss'or on'umme- ALCOBOLB, are.
. To all whom it may comem:
a citizen of the United States, residing at Berkeley, in the county of Alameda and .State of California, have invented certain new and useful Improvements in Processes of Obtaining Aloohols, Etc., of which the' following is a specification.
My. invention relates particularly to a process designed for obtaining alcohols havence to the production of abso ute alcohol. The object of my invention is to provide 95%, and particularly absolute alcohol, may be obtained. 4
A- further object is toobtain this end by distilling an alcohol with a second liquid, as, for example,water, and arthll'd constituent that is miscible with the alcohol but substantially immiscible with the second liqu d, as, for example, ethyl acetate, thus obtam ing a vapor mixture having d1fi'eren-t proportions of the constituents than the liquid being distilled and preferably so as-to obtain, as a result of the distillation, a constant boiling mixture of the three liquids and as well as an alcohol of a high strength.
Another object is to provide such a proc-.
ess wherein the vapors evolved in vthe distillation may be condensed and separated into two immiscible liquids containing, respecti-yely, high and low percentages of the third constituent, as by the addltionof a further quantity of the second liquid to the condensate.
Again, a further object is to distill these- .two liquids separately in such a manner as to obtain from one of them the third constituent, as a residue, of substantially 100% strength as well as a condensate comprising said constant boiling mixture and from the other liquid a residue of water together with a condensate'of said constant boiling mixture. I
Further, the object of my invention is to provide a continuous process in which the aforesaid distillations are conducted simul-' ing a high strength and has especial refer-- Application am April 14, 1921. swarm. 401302.
taneously while the distillates are collected together and separated continuously in the manner described.
Further objects of my invention will appear fromithe detailed description thereof contained hereinafter. I y
While my invention is capable of being carried out in many different ways, for the purpose of illustration I shall describe only certain ways of carrying 'out the same hereinafter, and while it is capable of bein carried out in connection with many di ferent types of apparatus, I have shown only one type of apparatus for use in connection therewith in the accompanying drawings, in which:
Figure 1 is a diagrammatic representation of an apparatus used in accordance with my invention; a
Figure 2 is a vertical section of the measuring receptacle, and
Figure 3 is a section of one of the columns. B
For example, in carrying out my invention, assuming that the same is a plied to the production of ethyl alcohol aving a high strength, as, for example, "absolute alcohol fromalcohol havin a lower strength and incidentally ethy acetate of 100%. strength, 95% strength alcohol is continually fed into a reservoir 1, the feeding of the alcohol vbeing begun as soon as a quantity of ethyl acetate, which is supplied initially to a reservoir 1, has .passed measuring receptacle 2 and therefrom the.
mixture flows'by a pipe 3 to a mixing coil 4, where the constant boiling mixtureis brought into contact with a current of water fed from a water supply 5 to a measur- 55 of water passing through inlet and outlet ing receptacle 6, and thence b a pipe 7 to said-mixing coil 4. Each of t e measuring receptacles 2 and 6 is comprised of a centoa tral inlet pi e 8 connected at the to feed- 1 near the top thereof a slot 13 to carry ofi' 7 approximately the overflow from the measuring receptacle and indicate by the height of-the outflowing liquidon a scale 14 at the edge of the slot 13 the rate of flow of the liquid from the measuring receptacle. The rates of flow of the water and the constant boiling solution are regulated so that the volumes of the two liquids fed during a given interval of time are substantially equal. From the mixing coil 4 the liquids pass into-a separating tank 15 where an upper layer 16 separates out containing by weight 93% ethyl acetate, 51/ water and 1.5% alcohol, and where a lower layer 17 is formed containing 8% ethyl acetate, 86% water, and 6% ethyl alcohol. These percentages wlll vary, however, to a considerable extent. The upper layer 16 is drawn off by a pipe 18, and is fed thereby into the side of a column 19 made up of a plurality of pans 20 carrying liquid which overflows from each pan to the next pan below by a series ofpipes 21, while the vapors are caused to pass through the bodies of liquid on the pans through liquid sealed bells 22 and pipes 23 leading into the same. Steam is provided for the column 19 by means of aheater 24 located at the bottom thereof comprising tube sheets 25 and26 carrying tubes 27 an supplied with heating steam by inlet and outlet pipe 28 and 29. From the base of this column there is a drawofi' pipe 30 for ethyl acetate having a strength of 100% which leads to a. sight glass 31 having a vent pipe 32leading back to the column 19, and
an outlet pipe 33 leadin from the bottom thereof. By means of t e steam roduced in'the heater 24, the lower end o the 'column 19 is maintained at a temperature of substantially 77 (1., while the top of said column is maintained at a temperature of C. From the top of the ere is a vapor mixture concolumn 19, t
, tain ethyl acetate, water, and alcohol carwhich the con ried over, which is conveyed by a pipe 34 to a dephlegmator 35 cooled by a current pipes 36 and 37 and from which dephlegmator any condensed liquid passes back by a'pipe 38 to the tower 19; From the dephlegmator 35, the uncop densed vapors of ethyl acetate, alcohol, an "water pass by a pipe 39 to a condenser 40, cooled by a current of water provided with the aid of inlet and outlet ipes 41 and 42, and from disused liquid passes into a 11 beneath which there sight glass 43 havin a vent 44 and a draw- 0 pipe 45; .Fromt is pipe 45 there is conveyed away a solution containing approximately 83% ethyl acetate, 8% 7 water, and
9% alcohol, which is discharged into thezo 'tank 1.
The lower layer of liquid 17, is conducted by a pipe 46 to the side of a second collumn 47 constructed the same as the column 19, except that thereis aninlet pipe 48 at the bottom thereofzprovided with perforations to inject live steam instead of utilizi ing indirect heat. The steam thus injected maintains the lower end of the column 47 at a temperature of approximately 100 0.,
and the upper end of the column at a temperature of about 70 C. From the bottom of the column an outlet pi e 49 conve s away the water, and from t e top of-tlle.
column, which is provided with a dephlegmator 50 and a condenser 51, constructed the same as in the case of the column- 19, a discharge pipe 52 conveys away the condensed liquid which is approximately the constant boiling solution comprising 83% ethyl acetate, 8% water, and 9% alcohol to the tank 1. Near the top of the column 47 where the temperature in the column is substantially 78 6., an outlet pipe 53 is provided for conveyingmwalyl the excess ethyl alcohol having substantia a 95% strength to the side of a third column 54. The col-' umn 54 is constructed the same as the column 19, except that in addition to the inlet pipe 53, there is an inlet pipe 54* com lower end of this column 54 is maintained 1l0 at a temperature of substantially 78 0,, and the top of the tower is maintained at a temperature of about 70 C. 'From the lower end of-this tower there is drawn off alcohol having a high strength, for example, 115
absolute alcohol, by means of a pipe 55, and from the upperend of the tower which is provided with a dephlegmator 56 and a condenser 57, there is conveyed away by means of a pipe 58 a constant boiling solution containing 83% ethyl acetate, 8% water, and 9% ethyl alcohol, which is discharged by said pipe into the tank 1.
The process as thus conducted will result in the production of absolute alcohol which 5 is discharged by the pipe 55, eth l acetate having a strength of 100% whic may, if desired, be disc arged from the pipe 33, and water which is discharged by the, pipe 49.
t It will be understood that the amount of 9 there is an inlet in water but is soluble in the alcohol such as benzol, or any other suitable material Where that may beused for this purpose. propyl alcohol is used propyl acetate could be the third constituent used therewlth.
above in detail, I wish it to be understood that man changes may be made therein without eparting from the spirit thereof.
I claim: q l 1. The process of eliminating a constltuent of a binary liquid mixture whose ingredients form a constant boiling mixture, comprising the addition thereto of a third liquid that forms a ternary constant boiling mixture with the. other two ingredients and thedistillation of the ternary mixture to evolve the ternary constant boiling mixture and leave as a residue the constituent of the the constituent to be eliminated; to the ten nary constant boiling distillate, and allowing liquid layers to separate out; distilling each layer -to evolve constant boiling mixtures and leave as residues liquids containing as principal constituents respectively the added liquid and the liquid desired to be re-- covered, and returning these residues to the original mixture undergoing distillation.
2. The process of claim 1 wherein the constant boiling mixtures evolved from the distillation of the layers, are added to the first named constant boiling mixture. v
3. The process which comprises distilling a ternary minimum boiling point mixture from a mixture of ethyl alcohol, ethyl acetate and water; adding water thereto and allowing the distillate to separate into two layers; distilling each layer to evolve constant boiling mixtures and adding them to the condensed distillate of the primary distilling process, and obtaining the ethyl acetate and alcohol of low aqueous content as residues of said distillations and returning them to the first liquid mixture undergoing distillation.
4. The process which comprises rectifying a mixture ofan ester, water, and an alcohol, containing a larger percentage of the alcohol 'than would be contained in a constant boiling water to the latter and allowing liquid layers to separate out; distilling the layer richer in ester to evolve a constant boiling mixture and leave a large proportion of the ester as a residue, and, adding the latter to the primary mixture undergoing distillation.
5. The process which comprises rectifying ing mixture of these constituents, and thereby obtaining alcohol substantially free from water, rectifyinga mixture of an ester, water and an alcohol, containing a larger percentage of-the ester than would be contained in a constant boiling mixture of these three constituents so as to obtain some of the ester- While I have described my mvention substantially free from water, feeding the latter into the rectifier in which the alcohol percentage of the ester is being rectified and distllllng .the second layer to recover valcohol of low. aqueous content, and returning it to the primary mixture undergoing distillation.
6. The process which comprises rectifying a mixture of an ester, water, and an alcohol, containing a larger percentage of the alcohol than would be contained in a constant boiling mixture of these constituents, and thereby obtaining alcohol substantially free from water, rectifying a mixture of anester, water and alcohol, containing a larger percentage of the ester than would be contained in a constant boiling mixture of these three constituents so as to obtain some of "the ester substantially free from water, feeding'the latter into the rectifier in which the alcohol substantially free from water is being obtained, obtaining a constant boiling mixture of the ester, the alcohol and water from such rectification, feeding suchconstant boiling mixture into contact with a body of water. separating the two bodies of liquid formed to form a liquid layer containing a high percentage of the ester and a liquid layer containing a low percentage of the ester, feeding the first mentioned liquid layer into the rectifier in which the mixture containing a higher percentage of the ester is being rectified, rectifying the other liquid layer to-recover a more concentrated aqueous alcohol and feeding it into the rectifier in which the alcohol substantially free from water is ob.- tained.
7 The process which comprises rectifying a mixture of an ester, water, and an alcohol,
containin a larger percentage of the alcohol I obtained, obtaining a constant boiling mixture of the ester, the alcohol, and water from such rectification, feeding such constant boiling mixture into contact with a body of water, separating the two bodies of 1i uid formed to form a liquid layer contaming a high percentage of the ester and a liquid layer containing a low percentage of the ester, feeding the first mentioned liquid layer into the rectifier in which the mixture containing a higher percentage of the ester is being rectified, rectifying the other liquid layer to recover a more concentrateda ueous alcohol, and feeding it into the recti er in which the alcohol substantially free from water is obtained, the process being conducted so as to produce a constant boiling mixture of the ester, the alcohol and water in the three rectifications, and bringing the combined constant boiling mixtures from these rectifications into contact with the body of water above specified.
8 The process which comprises distilling a ternary mixture in a column to separate out one ingredient at the bottom thereof and to evolve a constant boiling mixture of the three ingredients, condensing the constant boiling mixture and treating it with an additional quantity of one of the ingredients 7 to form two immiscible liquids, passing one of the latter liquids to a second column, distilling it therein to recover one of said ingredients, and returning the latter to the rst-column; passing the other liquid to a 7 third column, distilllng it therein to recover another of said ingredients, and returning the latter to the first column.
9 The invention in claim8 wherein the mixture comprises ethyl alcohol, ethyl acetate, and water.
10. The process which comprises distilling a ternary mixture in acolumn' to separate out one ingredient at the \bottom thereof and to evolve a constant boilin mixture of the three ingredients; condensing the constant boiling mixture and treating it with an additional quantity of oneof the ingredicuts to form two immiscible liquids, passing the latter to a second and a third distilling column respectively, distilling them therein,
condensing the constant boiling mixtures formed and adding them to that of the first column for separation, and recovering from of the ingredients and returning themto the first column.
11. The process which comprises distilling ethyl alcohol, ethyl acetate and water, in a column to separate out the alcohol at the bottom thereof while evolving a constant boiling mixture of the three ingredients; condensing the latter and treatingrit with an additional quantity of water to form two liquid layers; passing the latter to a second and a third column respectively, rectifyin them therein, condensing the constant iE ing mixtures formed and adding them to that from the first column, and recovering from said columns substantial quantities of alcohol and ester and returning them to the first column.
12. The process of obtaining alsolute alcohol, from an aqueous alcohol, whichas a residue; mixing the said constant boil- I mg mixture with waterto form liquid layers; separately distilling each layer to recover the said substance and e ueous alcohol; and returning the said su stance and aqueous alcohol to the aqueous alcohol undergoing distillation.
13. The process of obtaining an absolute alcohol from an aqipeous alcohol, which comprises: distilling t e latter with a substance miscible with the' alcohol but immiscible with water, to form a constant boiling mix ture of said substance, alcohol and water, and thereby obtaining an absolute alcohol as a residue; mixing'thesaid constant boiling mixture with water to formliquid layers; separately distilling each layer to evolve ternary constant boiling mixtures and to recover a substantial quantity of the said substance and "aqueous alcohol; and returning the said substance and aqueous alcohol to the first named aqueous alcohol.
1.4. The invention in claim 13 wherein the constantboilin mixtures evolved from the secondary distillations are added to the first constant boiling mixture for subsequent separation. Y 1
15. The process of obtaining absolute alcohol from aqueous ethyl alcohol which comprises: distilling the latter with ethyl acetate to form a constant boiling mixture of ester, alcohol and water and thereby obtaining absolute alcohol as a residue; mixing the said constant boiling mixture with water to form liquid layers; separately distilling each layer to recover a substantial quantity of the ester and aqueous alcohol; and returning the ester and alcohol to the ethyl alcohol undergoing distillation. a
16. The process of obtaining absolute alco- III.
" hol from aqueous ethyl alcohol, which cornboiling mixtures and to'recover pure ester prises: distilling thelatter with ethyl aceand aqueous alcohol; and returning the ester 10 tate to form a constant boiling mixture of and alcohol to'the ethyl alcohol undergoing ester, alcohol and water, and thereby obdistillation.
taining absolute alcohol as a residue; mix- In testimony that I claim the foregoing, I
ing the said constant boiling 'mixture with have hereunto set my hand this 5th day of water to' form -liquidlayers, separately dis- April, 1921. tilling each layer to evolve ternary constant WORTH H. RODEBUSH.
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US461302A US1583314A (en) | 1921-04-14 | 1921-04-14 | Process of obtaining alcohols, etc. |
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US461302A US1583314A (en) | 1921-04-14 | 1921-04-14 | Process of obtaining alcohols, etc. |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2702783A (en) * | 1952-03-14 | 1955-02-22 | Gulf Research Development Co | Process of separating mixtures of organic compounds |
-
1921
- 1921-04-14 US US461302A patent/US1583314A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2702783A (en) * | 1952-03-14 | 1955-02-22 | Gulf Research Development Co | Process of separating mixtures of organic compounds |
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