US1982160A - Manufacture of acetic acid from alcohol - Google Patents
Manufacture of acetic acid from alcohol Download PDFInfo
- Publication number
- US1982160A US1982160A US688258A US68825833A US1982160A US 1982160 A US1982160 A US 1982160A US 688258 A US688258 A US 688258A US 68825833 A US68825833 A US 68825833A US 1982160 A US1982160 A US 1982160A
- Authority
- US
- United States
- Prior art keywords
- alcohol
- acetic acid
- acid
- solvent
- solution
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 75
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title description 33
- 238000004519 manufacturing process Methods 0.000 title description 12
- 235000019441 ethanol Nutrition 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000002253 acid Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 20
- 238000005868 electrolysis reaction Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 239000007800 oxidant agent Substances 0.000 description 12
- 230000001172 regenerating effect Effects 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000010533 azeotropic distillation Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000008929 regeneration Effects 0.000 description 6
- 238000011069 regeneration method Methods 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 5
- 235000005985 organic acids Nutrition 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 1
- 241000973887 Takayama Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
Definitions
- one contents one- 19 self with determining the consumption of oxidizing agent in order to deduce therefrom the alcohol that was present in the liquid treated, without in addition endeavouring to estimate or to isolate the acid that is formed.
- the alcohol is oxidized with almost quantitative yields by I **d and submitting the spent solution containing the reduced salts to the action of electrolysis to bring the salts back to the desired degree of oxidation in order to enable them to exert a fresh action on the alcohol.
- an oxidizing salt as for example potassium bichromate
- a hydro-alcoholic solution so as to have, after the reaction, as small an excess of oxidizing solution as possible.
- the dilute acetic solution obtained in this way is then treated in the cold in an extraction battery of known type by a solvent such as ethyl acetate or a mixture of benzene and methylethyl ketone or any other solvent which is only slightly sensitive to the action of the small quantity of, oxidizing agent that may remain in solution.
- the extract of acetic acid in the solvent is distilled ,by the known azeotropic method; the acid is separated in the anhydrous form whilst the recovered solvent can be repeatedly used indefinitely.
- the spent aqueous solution leaving the extraction battery may, without disadvantage, contain a small proportion of acetic acid, the latter having the property of resisting sufliciently well in a very dilute, solution the subsequent operations of electrolytic oxidation carried out with a view to the regeneration of the oxidizing agent (Takayama, Zoc. cit).
- This possibility of contenting oneself with an exhaustion that is not far advanced and is consequently fairly inexs5 pensive forms one of the advantages and one of the features of the invention.
- the aqueous solution that has been roughly freed from acetic acid and from solvent and that contains chromous salts, is then treated, advantageously by electrolysis, with a view to the regeneration of the original chromic solution.
- it is in no way essential to carry the operation to the end as is usually necessary in the manufacture of chromates. There is thus obtained a very high yield of utilization of the oxygen produced by the current, which yield is of the order of 95% to 98%.
- the alcohol that is used as initial material can, no
- the method of maufacturing organic acids from alcohols consisting in treating the alcohol withan aqueous-solution of a bichromate salt, extracting the produced acid by ethyl acetate, regenerating the residual spent salt solution by electrolysis for re-use and separating the acid from the ethyl acetate by azeotropic distillation and re-using the latter in the process.
- the method of manufacturing organic acids from alcohols consisting in treating the alcohol with an aqueous solution of a biohromate salt, extracting the produced acid by a mixture of benzene and methylethyl ketone, regenerating the residual spent salt solution by electrolysis for reuse and separating the acid from said mixture by azeotropic distillation and re-using the mixture in the process.
- the method of manufacturing acetic acid from ethyl alcohol consisting in treating the alcohol with an aqueous solution of a bichromate salt, extracting the acetic acid by a mixture of benzene and methylethyl keto'ne, regenerating the spent salt solution by electrolysis, re-using the regenerated solution in the process, separating the acetic acid from the benzene and methylethyl ketone by azeotropic distillation, and reusing the recovered benzene and methylethyl ketone in the process.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR757155T | 1932-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1982160A true US1982160A (en) | 1934-11-27 |
Family
ID=9165957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US688258A Expired - Lifetime US1982160A (en) | 1932-09-16 | 1933-09-05 | Manufacture of acetic acid from alcohol |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US1982160A (fr) |
| FR (1) | FR757155A (fr) |
| GB (1) | GB410373A (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2455405A (en) * | 1946-10-17 | 1948-12-07 | Du Pont | Preparation of monochloroacetic acid |
| US2530512A (en) * | 1947-06-13 | 1950-11-21 | Celanese Corp | Oxidation of aliphatic esters |
| US3008985A (en) * | 1957-04-11 | 1961-11-14 | Renault | Methods of synthesizing 2-4-4-4 tetrachlorobutyric acid |
| US3946068A (en) * | 1968-10-12 | 1976-03-23 | Societa Italiana Resine S.I.R. S.P.A. | Process for the production of vinyl acetate from ethylene |
| US3985794A (en) * | 1968-10-12 | 1976-10-12 | Societa' Italiana Resine S.I.R. S.P.A. | Process for the production of vinyl acetate from ethylene |
| US3989742A (en) * | 1968-10-12 | 1976-11-02 | Societa' Italiana Resine S.I.R. S.P.A. | Process for the production of vinyl acetate from ethylene |
-
1932
- 1932-09-16 FR FR757155D patent/FR757155A/fr not_active Expired
-
1933
- 1933-09-04 GB GB24484/33A patent/GB410373A/en not_active Expired
- 1933-09-05 US US688258A patent/US1982160A/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2455405A (en) * | 1946-10-17 | 1948-12-07 | Du Pont | Preparation of monochloroacetic acid |
| US2530512A (en) * | 1947-06-13 | 1950-11-21 | Celanese Corp | Oxidation of aliphatic esters |
| US3008985A (en) * | 1957-04-11 | 1961-11-14 | Renault | Methods of synthesizing 2-4-4-4 tetrachlorobutyric acid |
| US3946068A (en) * | 1968-10-12 | 1976-03-23 | Societa Italiana Resine S.I.R. S.P.A. | Process for the production of vinyl acetate from ethylene |
| US3985794A (en) * | 1968-10-12 | 1976-10-12 | Societa' Italiana Resine S.I.R. S.P.A. | Process for the production of vinyl acetate from ethylene |
| US3989742A (en) * | 1968-10-12 | 1976-11-02 | Societa' Italiana Resine S.I.R. S.P.A. | Process for the production of vinyl acetate from ethylene |
Also Published As
| Publication number | Publication date |
|---|---|
| FR757155A (fr) | 1933-12-21 |
| GB410373A (en) | 1934-05-17 |
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