US837083A - Process for the manufacture of glycolic acid - Google Patents
Process for the manufacture of glycolic acid Download PDFInfo
- Publication number
- US837083A US837083A US837083DA US837083A US 837083 A US837083 A US 837083A US 837083D A US837083D A US 837083DA US 837083 A US837083 A US 837083A
- Authority
- US
- United States
- Prior art keywords
- acid
- glycolic acid
- manufacture
- cathodic
- oxalic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- AEMRFAOFKBGASW-UHFFFAOYSA-N glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 title description 44
- 238000000034 method Methods 0.000 title description 26
- 238000004519 manufacturing process Methods 0.000 title description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 90
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 36
- 229940116315 Oxalic Acid Drugs 0.000 description 30
- 235000006408 oxalic acid Nutrition 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 229940032330 Sulfuric acid Drugs 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- 229960000443 hydrochloric acid Drugs 0.000 description 8
- 235000011167 hydrochloric acid Nutrition 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- AYJRCSIUFZENHW-UHFFFAOYSA-L Barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 4
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 4
- 235000015450 Tilia cordata Nutrition 0.000 description 4
- 235000011941 Tilia x europaea Nutrition 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000005868 electrolysis reaction Methods 0.000 description 4
- 239000004571 lime Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 241001527902 Aratus Species 0.000 description 2
- 101710004359 CYP86A1 Proteins 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/25—Reduction
Definitions
- This invention relates to an economical, easy, and effective process of manufacturing glycolic acid.
- glycolic acid can be manufactured on a large scale from monochloracetic acid; but this process is notan easy one and is very expensive.
- An electrode not having a high cathodic overvoltage would give insufficient yields, and a too dilute acid would cause the oxalic acid, being highly ionized, to take too great a part in the conductivity of the current and to cause it to go to the anode, where it would be oxidized.
- the density of the current at the cathode may vary greatly for instance, from twenty-five to two hundred and fifty amperes per square meter of surface of cathode.
- the presence of the diaphragm in connection with the use of a not too dilute acid largely prevents the anodic oxidation of the oxalic acid.
- the anodic solution may be used in preparing a fresh charge of the cathodic liquor.
- sulfuric acid of a strength below fifteen parts concentrated sulfuric acid to one hundred parts of water, as otherwise the current yield and the nature of the product will be affected.
- the sulfuric acid can in the examples given be substituted for by about a twentypercent. hydrochloric acid.
- carbon or graphite can be used; but in using carbon a proportionately larger amount of current will have to be provided. Besides this other undesirable reactions seem to take place simultaneously.
- glycolic acid In order to produce glycolic acid from the electrolyzed solution in case sulfuric acid has been used, the solution is neutralized with lime, best added while stirring, until all the sulfuric acid and oxalic acid present is neutralized by the lime. In order to remove the last traces of sulfate of calcium, I use barium carbonate and oxalic acid in the usual way. In case hydrochloric acid has been used instead of the sulfuric acid during the electrolysis it is onlynecessary to evaporate the hydrochloric acid in order to get glycolic acid. The glycolic acid obtained by this process may be'used for technical as well as pharmaceutic purp oses.
- a process for the manufacture of glycolic acid from oxalic acid consisting in the electrolytic reduction of oxalicacid in the cathode-compartment of anelectrolytic app aratus in the presence-of electrodes having a cathodic overvoltag'e, the oxalic acid being dissolved in a suitable dilute acid kept Warm during the reduction and of such a degree of concentration that it excludes the oxalic acid from substantial participation in the conductivity.
- a process for the manufacture ofglfycolic acid consisting in the electrolytic reduction of oxalic acid in the cathodecompartment of an electrolytic apparatusin the pres- 'ence of lead e1ectrodes,the oxalic acid being dissolved in a dilute sulfuric acid kept Warm 1 5 during the reduction and of such a degree of concentration that it excludes the oxalic acid from substantial participation in the conductivity.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Description
the technical manufacture of the same.
UNITED STATES PATENT OFFICE.
OTTO LIEBKN-EGHT, OF FRANKFORT-ON-THE-MAIN, GERMANY, ASSIGNOR TO THE ROESSLER & HASSLAOHER CHEMICAL COMPANY, OF NEW YORK, N. Y., A CORPORATION OF NEW YORK;
' PROCESS FOR THE MANUFACTURE OF GLYCOLIC ACID.
To all whom it nwby concern.-
Be it known that I, OTTO LIEBKNEOHT, a subject of the GermanEmperor, and a resident of Frankfort-on-the-Main, Germany, have invented a certain new and useful Process for the Manufacture of Glycolic Acid, of which the following is a specification.
This invention relates to an economical, easy, and effective process of manufacturing glycolic acid.
The processes heretofore practiced of manufacturing glycolic acid are not adapted for For instance, it is known that glycolic acid can be manufactured on a large scale from monochloracetic acid; but this process is notan easy one and is very expensive. As a further illustration, it is impossible to economically produce glycolic acid from oxalic acid and zinc-dust because the yield is poor and the zinc-dust very expensive.
I have discovered that oxalic acid in sul furic-acid or hydrochloric-acid solution is reduced electrolytically nearly quantitatively and with a very good current yield. In practicing my process I have found it most satisfactory in reducing the oxalic acid electrolytically to use electrodes having a high cathodic overvoltageas, for instance, lead electrodesand to use a diaphragm to separate the anodic and cathodic liquors. Both of these features are import ant, as well as the use of a not too dilute acid. An electrode not having a high cathodic overvoltage would give insufficient yields, and a too dilute acid would cause the oxalic acid, being highly ionized, to take too great a part in the conductivity of the current and to cause it to go to the anode, where it would be oxidized.
As an example illustrative of my process I give the following: Seven hundred parts of crystallized oxalic acid are dissolved in about three thousand three hundred parts of water and eleven hundred parts of thirty-per-cent. sulfuric acid are added while stirring. This solution forms a cathodic liquor, which it is of advantage to keep warm during the process of electrolyzation.
should be placed in the cathodic compartment of a suitable electrolytic apparatus provided with a suitable diaphragm, and the anodic liquor, comprising a thirty-per-cent. sulfuric acid, should be placed on the other Specification of Letters Patent. Application filed June 1A, 1906. Serial No. 321.669.
The cathodic liquor Patented Nov. 27, 1906.
side ofthe diaphragm. The density of the current at the cathode may vary greatly for instance, from twenty-five to two hundred and fifty amperes per square meter of surface of cathode. The presence of the diaphragm in connection with the use of a not too dilute acid largely prevents the anodic oxidation of the oxalic acid. On completion of the electrolysis the anodic solution may be used in preparing a fresh charge of the cathodic liquor.
It is preferable to stir the cathodic liquor during the electrolyzing, and, furthermore,
to add fresh acid in case the acid in the cathodic liquor becomes too weak, a too concentrated solution, however, being avoided at the cathode on account of the resulting low conductivity. It is advisable not to use sulfuric acid of a strength below fifteen parts concentrated sulfuric acid to one hundred parts of water, as otherwise the current yield and the nature of the product will be affected. The sulfuric acid can in the examples given be substituted for by about a twentypercent. hydrochloric acid. In place of lead electrodes carbon or graphite can be used; but in using carbon a proportionately larger amount of current will have to be provided. Besides this other undesirable reactions seem to take place simultaneously.
In order to produce glycolic acid from the electrolyzed solution in case sulfuric acid has been used, the solution is neutralized with lime, best added while stirring, until all the sulfuric acid and oxalic acid present is neutralized by the lime. In order to remove the last traces of sulfate of calcium, I use barium carbonate and oxalic acid in the usual way. In case hydrochloric acid has been used instead of the sulfuric acid during the electrolysis it is onlynecessary to evaporate the hydrochloric acid in order to get glycolic acid. The glycolic acid obtained by this process may be'used for technical as well as pharmaceutic purp oses.
As it is obvious that the process may be practiced in a number of different ways with considerable variation, I do not restrict my.- self to the steps or proportions described; but
What I claim, and desire to secure by Letters Patent of the United States, is
1. A process for the manufacture of glycolic acid from oxalic acid consisting in the electrolytic reduction of oxalicacid in the cathode-compartment of anelectrolytic app aratus in the presence-of electrodes having a cathodic overvoltag'e, the oxalic acid being dissolved in a suitable dilute acid kept Warm during the reduction and of such a degree of concentration that it excludes the oxalic acid from substantial participation in the conductivity.
2. A process for the manufacture ofglfycolic acid consisting in the electrolytic reduction of oxalic acid in the cathodecompartment of an electrolytic apparatusin the pres- 'ence of lead e1ectrodes,the oxalic acid being dissolved in a dilute sulfuric acid kept Warm 1 5 during the reduction and of such a degree of concentration that it excludes the oxalic acid from substantial participation in the conductivity.
In Witness whereof I have hereunto signed 20 my name in the presence of'tWo subscribing OTTO LIEBKNECHT.
Witnesses.
Witnesses HORST ZIEGLER," JEAN GRUND.
Publications (1)
Publication Number | Publication Date |
---|---|
US837083A true US837083A (en) | 1906-11-27 |
Family
ID=2905557
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US837083D Expired - Lifetime US837083A (en) | Process for the manufacture of glycolic acid |
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US (1) | US837083A (en) |
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- US US837083D patent/US837083A/en not_active Expired - Lifetime
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