USRE15783E - Process of dehydrating organic liquids - Google Patents
Process of dehydrating organic liquids Download PDFInfo
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- USRE15783E USRE15783E US15783DE USRE15783E US RE15783 E USRE15783 E US RE15783E US 15783D E US15783D E US 15783DE US RE15783 E USRE15783 E US RE15783E
- Authority
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- United States
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- water
- vapors
- dehydrating
- contact
- organic liquids
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- 239000007788 liquid Substances 0.000 title description 23
- 238000000034 method Methods 0.000 title description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 229910001868 water Inorganic materials 0.000 description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 238000009835 boiling Methods 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000012024 dehydrating agents Substances 0.000 description 15
- 208000005156 Dehydration Diseases 0.000 description 13
- 238000006297 dehydration reaction Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 150000002170 ethers Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- BZKPWHYZMXOIDC-UHFFFAOYSA-N Acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N 3-Pentanone Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000750 progressive Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
Images
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
-
- 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
Definitions
- This invention relates to a process of dehydrating organic liquids and more particularly to a process of dehydrating ethyl ether.
- dehydrating many organic liquids by the use of the known dehydrating agents difiiculties have been encountered in secur- 16 in a substantially complete deh dration.
- the invention has as an object the avoidance of the above mentioned difliculties in the case of distillation by preventing the 80 formation, as far as possible, of constant boiling mixtures, and avoiding the simultaneous distillation of water and organic liquid. It has also as an object a dehydration and purification by a reagent which is inexpensive and easy to handle.
- a still further ob ect is to thoroughly dehydrate organic liquids of various kinds so as to remove the last traces of water.
- a dehydrating agent in a distillation process in such. a manner as to remove it from con-- tact with theorganic liquid after it has ab-l sorbed quantities of Water so that the latter n will not be able to again become admixed with the organic liquid and form constant boiling mi xtures or redistill therewith.
- a flask 1 is shown immersed in a liquid or water bath 2 placed on ahot plate 3, and this flask is closed with a stopper 4 provided with three holes, one for the insertion of an inlet tube 5, another for a siphon tube 6, and the third for the end of a column 7.
- a test tube 8 positioned to receive the siphon tube 6 and to catch liquid falling from the column 7.
- the latter is filled with glass beads and pieces of sodium hydroxide in alternate layers.
- a condenser 9 surrounds the exit tube 10 leading from the top of the column and a thermometer 11 is inserted in the tube 10 to indicate the distillation temperatures.
- a branch tube 12 leads to a condenser 13 which is cooled by water or other cooling fluid in the usual way.
- Ethyl ether is admitted through the tube 5 to the flask 1 and distilled so that its vapors ascend in the column 7 and come into contact with the successive layers of sodium hydroxide, .with the result that they pass out to the condenser completel dehydrated.
- the sodium hydroxide absor s the water and ultimately forms a solution therewith which descends into the test tube 8 and is siphoned off as desired through the tube 6.
- a large excess of sodium hydroxide is always maintained so that the ether vapors will at some point in the column have to contact with solid sodium hydroxide in substantially anhydrous condition. The upper layer of the latter will of course remain the driest and should'be so maintained.
- the ether as it loses its Water is not continually kept in admixture with an aqueous dehydrating agent and be formed with water once removed nor can this water again be distilled with the ether in any form. .
- the water is removed from further contact with the etherand the pro'c-' ess may proceed to a complete dehydration.
- Ether is a su possible to market stance which tenaciously clings to water, even resisting the most owerful dehydrating agents as long as it ias an opportunity for establishing a state of equilibrium with them and the water, but when this state .is continually upset by progressive removal of the water, the ether is gradually deprived of the last aqueous portions. The dehydration may proceed to' about .01% water.
- ethers may be dehydrated b this r0ce$ such as propyl, eth l propy and utyl ethers, and others.
- arious ketones may also be dehydrated, for example, diethyl ketone and methyl ethyl ketone.
- Alcohol ma be dehydrated in this way and hydrocar ons, either aliphatic or aromatic maybe dehydrated by this process.
- any organic liquid containin water and having a oiling oint below t e boiling point of water, or orming constant boiling mixtures therewith having boiling points below that of water, and which are not decomposed by the dehydrating agent, may be treated by the process of this invention.
- the process may be continuously operated by admitting the ether or other liquid in tube 5 at approximately the same rate as it is distilled away in the flask 1.
- dehydrating agents may be used as potassium hydroxide or other alkali hydroxide soluble in water, alkali oxides soluble in water, alkali carbonates soluble in water, metallic sodium, phosphorus pentoxide, many other solid acid anhydrides soluble in water, calcium chloride, sodium chloride, cqlpper sulphate, and anhydrous sodium sulate.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
March 4 1924. R 15,783
J. A. s. HAMMOND PROCESS OF DEHYDRATING ORGANIC LIQUIDS Original Filed Deo 29, 1921 Reissued Mar. 4, 1924.
UNITED sTA Es PATENT OFFICE.
JOHN A. S. HAMMOND, OF WOODLAWN, MARYLAND, ASSI GNOB TO U. S. INDUSTRIAL ALCOHOL CO., A CORPORATION OF WEST VIRGINIA.
PROCESS OF DEHYDRATING ORGANIC LIQUIDS.
Original No. 1,486,485, dated August 28, 1923, Serial No. 525,797, flled December 29, 1921. Application for reissue filed December 15, 1923. Serial No. 680,916.
To all whom it may concern:
Be it known that I, J oHN'A. S. HAMMOND; a citizen of the United States, a resident of Woodlawn, in the county ofBaltimore and 5 State of Maryland, have invented a certain new and useful Process of Dehydrating Organic Liquids, of which the following is a specification.
This invention relates to a process of dehydrating organic liquids and more particularly to a process of dehydrating ethyl ether. In dehydrating many organic liquids by the use of the known dehydrating agents, difiiculties have been encountered in secur- 16 in a substantially complete deh dration. View it has been endeavored to ac iieve the latter by means of the simple addition of a dehydrating agent to the liquid, it has been found that all of the water could not be 20 wholly abstracted, and where a separation by distillation from the dehydratin agent has been tried, it has been found t at the water accompanies the organic li uid owing either to the closeness of their boi ing points 26 or to the formation of constant boiling mixtures.
The invention has as an object the avoidance of the above mentioned difliculties in the case of distillation by preventing the 80 formation, as far as possible, of constant boiling mixtures, and avoiding the simultaneous distillation of water and organic liquid. It has also as an object a dehydration and purification by a reagent which is inexpensive and easy to handle.
A still further ob ect is to thoroughly dehydrate organic liquids of various kinds so as to remove the last traces of water.
. These objects are in part accomplished by the use of a dehydratin agent in sufficient uantities to effect dehy ration and to at all times provide anhydrous portions to contact with the vapors or liquids just prior to their exit from the apparatus.
furthermore accomplished by the use of a dehydrating agent in a distillation process in such. a manner as to remove it from con-- tact with theorganic liquid after it has ab-l sorbed quantities of Water so that the latter n will not be able to again become admixed with the organic liquid and form constant boiling mi xtures or redistill therewith.
As a specific embodiment the dehydration of ethyl other will' be described in connec- These objects are I therefore no constant boiling mixtures can tion with the accompanying drawing which is of course adapted for use with other organic liquids.
In the drawing is shown an apparatus for distilling an organic liquid through a column containing sodium hydroxide and thereafter condensing it.
A flask 1 is shown immersed in a liquid or water bath 2 placed on ahot plate 3, and this flask is closed with a stopper 4 provided with three holes, one for the insertion of an inlet tube 5, another for a siphon tube 6, and the third for the end of a column 7. Within the flask is a test tube 8 positioned to receive the siphon tube 6 and to catch liquid falling from the column 7. The latter is filled with glass beads and pieces of sodium hydroxide in alternate layers. A condenser 9 surrounds the exit tube 10 leading from the top of the column and a thermometer 11 is inserted in the tube 10 to indicate the distillation temperatures. A branch tube 12 leads to a condenser 13 which is cooled by water or other cooling fluid in the usual way.
Ethyl ether is admitted through the tube 5 to the flask 1 and distilled so that its vapors ascend in the column 7 and come into contact with the successive layers of sodium hydroxide, .with the result that they pass out to the condenser completel dehydrated. The sodium hydroxide absor s the water and ultimately forms a solution therewith which descends into the test tube 8 and is siphoned off as desired through the tube 6. A large excess of sodium hydroxide is always maintained so that the ether vapors will at some point in the column have to contact with solid sodium hydroxide in substantially anhydrous condition. The upper layer of the latter will of course remain the driest and should'be so maintained.
In this manner the ether as it loses its Water is not continually kept in admixture with an aqueous dehydrating agent and be formed with water once removed nor can this water again be distilled with the ether in any form. .The water is removed from further contact with the etherand the pro'c-' ess may proceed to a complete dehydration.
The accomplishment of this object by this practical process makes it an ether,v free from water, and incidentall free from other impurities Ether is a su possible to market stance which tenaciously clings to water, even resisting the most owerful dehydrating agents as long as it ias an opportunity for establishing a state of equilibrium with them and the water, but when this state .is continually upset by progressive removal of the water, the ether is gradually deprived of the last aqueous portions. The dehydration may proceed to' about .01% water. The
resence of water in ether in amounts as ow as a fraction of 1% causes the formation in the course of standing of other impurities which constitute a serious objection where the ether is to be used for producing anaesthesia. The value of the above process is therefore ap arent in view of the resistance which et er manifests to ordinary methods of dehydration.
Other ethers may be dehydrated b this r0ce$ such as propyl, eth l propy and utyl ethers, and others. arious ketones may also be dehydrated, for example, diethyl ketone and methyl ethyl ketone. Alcohol ma be dehydrated in this way and hydrocar ons, either aliphatic or aromatic maybe dehydrated by this process. In fact, any organic liquid containin water and having a oiling oint below t e boiling point of water, or orming constant boiling mixtures therewith having boiling points below that of water, and which are not decomposed by the dehydrating agent, may be treated by the process of this invention.
The process may be continuously operated by admitting the ether or other liquid in tube 5 at approximately the same rate as it is distilled away in the flask 1.
, Other dehydrating agents may be used as potassium hydroxide or other alkali hydroxide soluble in water, alkali oxides soluble in water, alkali carbonates soluble in water, metallic sodium, phosphorus pentoxide, many other solid acid anhydrides soluble in water, calcium chloride, sodium chloride, cqlpper sulphate, and anhydrous sodium sulate. I p As many apparently widely different embodiments'of this invention may be made without departihg from the spirit'thereof, it is to be understood thatI do not intend to limit myself to the specific embodiment thereof except as indicated in the appended claims.
I claim:
1. The process of dehydratm organic liquids whose boiling points, an the boilmg points of their constant boiling mixtures with water, are less than that of water, comprising distilling them and assing their vapors in contact with a dehy atmg agent in such a manner that the vapors are finally exposedto substantially anhydrous portions of, the dehydrating agent to accomplish dehydration. v
2. The process of dehydrating ethers whose boiling points, and the boiling" points of their constant boiling mixtures with water, are less than that of Water, compris ing distilling them and passing their vapors in contact with a dehydrating agent in such a manner that the vapors are finally exposed to substantially anhydrous portions of the dehydrating agent to accomplish dehydration.
3. The process of dehydrating ethers. whose boiling points, and the boiling points of their constant boiling mixtures with water, are less than that of Water, comprising distilling them and passing their vapors in contact with sodium hydroxide in such a manner that the vapors are finally exposed to substantially anhydrous portions of the sodium hydroxide to accomplish dehydra tion.
4. The process of dehydrating an organic liquld comprising treating it with a dehydrating agent to remove most of the Water contained therein, and thereafter giving it a final treatment with a sufiicient quantity of a strictly anhydrous dehydrating agent to remove the last traces of water. I
5. The process of dehydrating organic liquids whose boiling points, and the boiling points of their constant boiling mixtures with water, are less than that of water, comprising distilling them and passing their vapors in contact with a dehydrating agent in such a manner that portions which deliquesce are removed from contact With the organic liquids and vapors, and the vapors are finally exposed to substantially anhydrous portions of the dehydrating agent to accom lish dehydration.
6. he process of dehydrating ethers whose boiling points and the boiling points of their constant boiling mixtures with water, are less than that of water, comprising distilling them and passing their vapors in contact with a dehydrating agent in such a manner that portions which deliquesce are removed from contact with the ethereal liquids and vapors,and the vapors are finally exposed to substantially anhydrous portions of the dehydrating agent to accomplish dehydration.
7. The process of dehydrating ethers whose boiling points, and the boiling points of their constant boiling mixtures with water, are less than that of water, compris ing distilling them and passing their vapors in contact with sodium hydroxide in such a manner that portions which deliquesce are removed from contact with the ethereal liquids and vapors, and the vapors are finally exposed to substantially anhydrous portions of the sodium hydroxide to accomplish dehydration.
8. The process of dehydrating ethyl ether comprising distilling it and passing the vapors in contact with sodium hydroxide in "uesce are removed from contact with the organic liquids and vapors.
10. The process of dehydrating ethers whose boiling points, and the boiling points of their constant boiling mixtures with water, are less than that of water, comprising distilling them and passing their vapors in contact with a dehydrating agent in. such a manner that portions which deliquesce are removed from contact with the ethereal liquidsand vapors.
11. The process of dehydrating ethyl ether comprising distilling it and passing the vapors in contact with sodium h droxide in such, a manner that portions whic deliquesce are removed from contact with the ether liquid and vapors.
12. The process of dehydratin organic liquids whose boiling ponts, and t eboiling points of their constant boiling mixtures with water, are less than that of water, comprising continuously distilling them and passing their vapors in contact with a de ydrating a ent in such a manner that the vapors are nally exposed to substantially anhydrous portions of the dehydrating agent to accomplish dehydration.
13. The process of dehydrating ethyl ether comprising continuously distilling it and passing the vapors in contact with sodium hydroxide in such a manner that portions which deliquesce are removed from contact with the ether liquid and vapors, and the vapors are finally exposed to substantially anhydrous portions of the hydroxide to accomplish dehydration.
JOHN A. S. HAMMOND.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE15783E true USRE15783E (en) | 1924-03-04 |
Family
ID=2076862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US15783D Expired USRE15783E (en) | Process of dehydrating organic liquids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE15783E (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2595544A (en) * | 1946-06-18 | 1952-05-06 | Du Pont | Dehydration of organic fluids |
| US2967825A (en) * | 1957-12-26 | 1961-01-10 | Makhtsavei Israel | Process for the athermal removal of water from aqueous liquors by an organic solvent |
| US3138545A (en) * | 1955-05-10 | 1964-06-23 | Fmc Corp | Dehydration of nu, nu-dimethylhydrazine by distillation in the presence of an alkali |
| US3584737A (en) * | 1967-06-19 | 1971-06-15 | Gold Und Silbia Scheideanstalt | Process for drying organic solvents by sodium monoxide treatment and distillation |
-
0
- US US15783D patent/USRE15783E/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2595544A (en) * | 1946-06-18 | 1952-05-06 | Du Pont | Dehydration of organic fluids |
| US3138545A (en) * | 1955-05-10 | 1964-06-23 | Fmc Corp | Dehydration of nu, nu-dimethylhydrazine by distillation in the presence of an alkali |
| US2967825A (en) * | 1957-12-26 | 1961-01-10 | Makhtsavei Israel | Process for the athermal removal of water from aqueous liquors by an organic solvent |
| US3584737A (en) * | 1967-06-19 | 1971-06-15 | Gold Und Silbia Scheideanstalt | Process for drying organic solvents by sodium monoxide treatment and distillation |
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