US1876454A - humphkjey - Google Patents
humphkjey Download PDFInfo
- Publication number
- US1876454A US1876454A US1876454DA US1876454A US 1876454 A US1876454 A US 1876454A US 1876454D A US1876454D A US 1876454DA US 1876454 A US1876454 A US 1876454A
- Authority
- US
- United States
- Prior art keywords
- fenchone
- pine oil
- oxidation
- nitric acid
- produced
- 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
- LHXDLQBQYFFVNW-XCBNKYQSSA-N (+)-Fenchone Natural products C1C[C@]2(C)C(=O)C(C)(C)[C@H]1C2 LHXDLQBQYFFVNW-XCBNKYQSSA-N 0.000 description 188
- 229930006735 fenchone Natural products 0.000 description 94
- 230000003647 oxidation Effects 0.000 description 80
- 238000007254 oxidation reaction Methods 0.000 description 80
- 239000010665 pine oil Substances 0.000 description 80
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 64
- 229930006727 (-)-endo-fenchol Natural products 0.000 description 38
- IAIHUHQCLTYTSF-MRTMQBJTSA-N (-)-endo-fenchol Chemical compound C1C[C@]2(C)[C@H](O)C(C)(C)[C@H]1C2 IAIHUHQCLTYTSF-MRTMQBJTSA-N 0.000 description 38
- 239000002253 acid Substances 0.000 description 28
- 238000009835 boiling Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 12
- 230000001590 oxidative Effects 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000011149 sulphuric acid Nutrition 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 10
- 239000001117 sulphuric acid Substances 0.000 description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 4
- 235000011613 Pinus brutia Nutrition 0.000 description 4
- 241000018646 Pinus brutia Species 0.000 description 4
- -1 as for example Substances 0.000 description 4
- 230000005591 charge neutralization Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000001264 neutralization Effects 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- VKJKEPKFPUWCAS-UHFFFAOYSA-M Potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 2
- 229940046063 Potassium chlorate Drugs 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
Definitions
- My invention relates to a method for producing fenchone, and more particularly relates to the production of. fenchone by the use of pine oil through the oxidation of fenchyl alcohol contained therein, the pine oil being first fractionated for concentration of the fenchyl alcohol.
- the nitric acid or the mixture of acids used are diluted with water and may be heated at least initially, to promote oxidation. After the oxidation has started, it may not be necessary to continue the application of heat and since the reaction with nitric acid is preferably carried out at a temperature within about the range O.99 C. it may be necessary to cool the reaction mixture. 7
- pine oil fraction is utilized.
- pine oil may be fractionated, or, if desired, fractionated and refractionated, to
- a pine oil fraction may-be obtained by fractionating pine oil to obtain a fraction boiling largely between about 196 C. and 207 C. It will be understood that in thecarrying out of my method a pine oil out having a wider boiling range than that indicated as preferable may be used. The boiling range of the pine oil fraction treated, it will be understood, is dictated mainly by considerations of economy.
- the nitric acid may be used withinawide range of-concentration, i. e. 15-40% I-INO' but preferably thedilute nitric acid will be of a concentration within about the range 2O35% HNO I I
- mixed acids are used for the oxidation of a pine oil cut, for example, a pine oil out boiling within. aboutthe range 198 (1-207 C.
- the acid mixture is held at a temperature of about 85 F.
- the temperature of the acid is raised to about 100 F. and maintained at that temperature for say about 4 hours, in order to insure completion of the oxidation.
- crude fenchone is separated from the spent acids, treated with an alkaline solution for neutralization and steam distilled-from the alkaline solution.
- a yield of about 80 g. of refined fenchone, boiling point 192 198 C. is obtained, which, if desired, may be further refined by treatment with, for example, alcoholic sodium hydroxide or with aqueous sodium hydroxide.
- the proportions of acidsand water in the mixture may be varied within relatively wide limits.
- the sulphuric acid is preferably present in amounts within about therange l()%60% and the water, while it may be present in amount less than 30%, is preferably present in amount within about the range 25 l0%.
- the fenchone produced by the oxidation of a pine oil cut by the use of nitric acid or mixed acidcontaining nitric acid is comparable with fenchone produced by the oxidation of crystalline fenohyl alcohol and, for exthe colloiding action of the product in accordance with the method of my invention, on nitrocotton is, from the practical standpoint as good as that of fenchone derived from crystalline fenchyl alcohol.
- fenchone may be produced at a substantial saving of time and expense, since the necessity for obtaining relatively pure or crystalline fenchyl alcohol, and which involves substantial: difficulty and expense, is avoided.
- sulphuric acid which acts in a sense catalytically to promote the liberation of nitric oxide, is preferably used with the nitric acid.
- sulphuric acid may be replaced by other mineral acids, as for example, phosphoric acid.”
- nitric acid oxides of nitrogen may mg agent in the presence of oxygen and water be employed as the oxidizand it will be further understood that small amounts of a halogen salt, as ferric chloride,
- the method of producing fenchone which includes subjecting a pine oil out containing fenohyl alcohol to heat in the presence of dilute nitric acid to efiect oxidation thereof and separating fenchone produced from other oxidation products.
- the method of producing fenchone which includes fractionating pine oil to obtain a fraction containing about 75% fenchyl alcohol, subjecting the fraction to oxidation with nitric acid and separating the fenchone roduced from other oxidation products by distillation.
- the method of producing fenchone which includes fractionating pine oil to obtain a fraction boiling within about the range 196 C.-207 0., subjecting the fraction to oxidation with nitric acid and separating the fenchone produced from other oxidation products.
- the method of producing fenchone which includes fractionating pine oil to obtain a fraction boiling within about the range 196 (1-207 C., subjecting the fraction to heat in the presence of nitric acid and separating the fenchone produced from other oxidation products.
- the method of producing fenchone which includes fractionating pine oil to obtain a fraction boiling within about the range 196 C.2O7"v 0., subjecting the fraction to heat in the presence of nitric acid of a concentration within about the range 15%4:0% and separating the fenchone produced from other oxidation products.
- the method which includes fractionating pine oil to obtain a fraction boiling within about the range 196 C.207 0., and oxidizing with a mixture of nitric and sulphuric acids and separating fenchone produced from other oxidation products. 7
- the method of producing fenchone which includes subjecting a pine oil out rich in fenchyl alcohol to oxidation with a mixture of nitric acid and a mineral acid, and separating fenchone from other oxidation products produced.
- the method of producing fenchone which includes subjecting a pine oil out rich in fenchyl alcohol to'oxidation with nitric acid in the presence of a substance which acts to promote the liberation of nitric oxide and separating fenchone from other oxidation products produced.
- the method of producing fenchone which includes subjecting a pine oil out rich in fenchyl alcohol to oxidation with nitric acid in the presence of a substance which acts catalytically to promote the liberation of nitric oxide and separating fenchone from other oxidation products produced.
- the method of producing fenchone which includes subjecting a pine oil cut rich in fenchyl alcohol to oxidation with nitric acid in the presence of a mineral acid and separating fenchone from other oxidation products produced.
- the method of producing fenchone which includes subjecting a pine oil out rich in fenchyl alcohol to oxidation With an oxidizing mixture including about 55% sul-' phuric acid, about 14% nitric acid and about 31% water and separating fenchone from other oxidation products produced.
- a method of producing fenchone which includes oxidizing a pine oil out containing fenchyl alcohol with nitric acid of a concentration within and separating fenchone produced from other oxidation products by distillation.
- a method of producing fenchone which includes oxidizing a pine oil out boilin within about the range 196207 C. and containing fenchyl alcohol with nitric acid of a concentration within about the range 15 %40% and separating fenchone produced from other oxidation products.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
Description
obtain a fraction having a Patented Sept. 6, 1932 Invr'n w. HUMPHBEY, on wHAR'roN,
NEW JERSEY, ASSIGNOR TO HERCULES rownnn COMPANY, on WILMINGTON, nnnnwnnn, A CORPORATION OEDELAWARE iunrnonor PRODUCING rnncHoNE No Drawing.
My invention relates to a method for producing fenchone, and more particularly relates to the production of. fenchone by the use of pine oil through the oxidation of fenchyl alcohol contained therein, the pine oil being first fractionated for concentration of the fenchyl alcohol.
I The method according to myv inv ention de pends upon the disco-very that ifa pine oil fraction containing fenchylalcohol be subjected to oxidation, fenchone will be produced through oxidation ofthe fenchylalcohol present in the pine oil out and the fenchone produced may bereadily-separated from other oxidation products produced due to the fact that the fenchone may be volatilized with steam, whereas theoxidation.prodnets of the other pine oil components of the cut are'nonevolatile with steam. Hence, after the oxidation of the pine oil fraction, ,the fenchone produced, may be readily. recovered. Thus, it will be noted thatby virtue of my invention the necessity for obtaining fenchyl alcohol substantially pureor in crystalline form before oxidation to fenchone isavoided. This separation involves substantial difiiculty due to the solubility of the fenchyl alcohol in pine oil and the nearness of its boiling point to the boiling points of certain other ingredients of the plne oil; I I r In carrying out the method in accordance with my invention, a pine oil fraction contalning'fenchyl alcoholis oxidized with nitric acid or with a mixed acid containing nitric acid, as a mixtureof nitric acid and-sulphuric acid. The nitric acid or the mixture of acids used are diluted with water and may be heated at least initially, to promote oxidation. After the oxidation has started, it may not be necessary to continue the application of heat and since the reaction with nitric acid is preferably carried out at a temperature within about the range O.99 C. it may be necessary to cool the reaction mixture. 7
In the carrying'out ofthe method inaccordance with my invention,as has been indicated, a pine oil fraction is utilized. For example, pine oil may be fractionated, or, if desired, fractionated and refractionated, to
fenchyl alcohol Application filed January 14,1928; Serial No. 246,905.
concentration of say ple, a, suitable pine oil fraction may-be obtained by fractionating pine oil to obtain a fraction boiling largely between about 196 C. and 207 C. It will be understood that in thecarrying out of my method a pine oil out having a wider boiling range than that indicated as preferable may be used. The boiling range of the pine oil fraction treated, it will be understood, is dictated mainly by considerations of economy.
' In carrying out the method in accordance with my invention, using for example, nitric acid, the pine oil out boiling within about therange 196 C.205
or more. For exam- C. is obtainedand say about 160 parts of such cut, whichcontainsabout 75% of fenchyl alcohol, is added in the course of about 2 hours, withagitation, to about 500 parts of dilute nitric acid (20.53% I-INO The nitric acid during the addition of the pine oilcut should be heated to a temperature of. about 190 F. 'On completion of the addition of the pine oil out to the nitric acid, heating is continued for about hours in order to complete the oxidation. On completion of the oxidation, the crude fenchone is separated from the spentacid, treated with an alkaline solution to effect neutralization and then steam distilled from the alkaline solution. --A yieldof about parts of fenchone will be obtained. v
In the carrying out of the method in accordance with my invention with theme of dilute nitric acid, it will be understood that the nitric acidmay be used withinawide range of-concentration, i. e. 15-40% I-INO' but preferably thedilute nitric acid will be of a concentration within about the range 2O35% HNO I I In the carrying out of the method in accordance with my invention Where mixed acidsare used for the oxidation of a pine oil cut, for example, a pine oil out boiling within. aboutthe range 198 (1-207 C. is ob- .tained and say about 160 parts of such out isadded overa period of about 3 hours, with agitation, to about 7O0 parts of an acid mixture containing, for example, about 55.1% sulphuricacid, about 14.3% nitric acid and'about 305% water,
During the-addition of the pine lot the mixed acids for oxidation 'fample,
economy in that alcohol is treated, larger "as compared with the yield of other oil cut, the acid mixture is held at a temperature of about 85 F. After the completion of the addition of the pine oil cut, the temperature of the acid is raised to about 100 F. and maintained at that temperature for say about 4 hours, in order to insure completion of the oxidation. When the oxidation is complete crude fenchone is separated from the spent acids, treated with an alkaline solution for neutralization and steam distilled-from the alkaline solution. A yield of about 80 g. of refined fenchone, boiling point 192 198 C. is obtained, which, if desired, may be further refined by treatment with, for example, alcoholic sodium hydroxide or with aqueous sodium hydroxide. In the use of of the pine oil out, it will be understood that the proportions of acidsand water in the mixture may be varied within relatively wide limits. However, the sulphuric acid is preferably present in amounts within about therange l()%60% and the water, while it may be present in amount less than 30%, is preferably present in amount within about the range 25 l0%.
The fenchone produced by the oxidation of a pine oil cut by the use of nitric acid or mixed acidcontaining nitric acid, is comparable with fenchone produced by the oxidation of crystalline fenohyl alcohol and, for exthe colloiding action of the product in accordance with the method of my invention, on nitrocotton is, from the practical standpoint as good as that of fenchone derived from crystalline fenchyl alcohol.
It will be noted that in accordance with the methodof my invention, fenchone may be produced at a substantial saving of time and expense, since the necessity for obtaining relatively pure or crystalline fenchyl alcohol, and which involves substantial: difficulty and expense, is avoided.
It will be understood that when a pine oil out is used the boiling range of such cut .45 i
may vary within wide limits, since the selection of the pine oil out is dictated merely by where a cut rich in fenohyl the yield of fenchone is oxidation products than when a pine oil out poorer in fenohyl alcohol is treated. Hence, the treatment of a cut rich in fenchyl alcohol results in the saving of nitric acid.
In the use of mixed acids according to my invention, sulphuric acid, which acts in a sense catalytically to promote the liberation of nitric oxide, is preferably used with the nitric acid. However, it will be understood that sulphuric acid may be replaced by other mineral acids, as for example, phosphoric acid." Further, in place of nitric acid oxides of nitrogen may mg agent in the presence of oxygen and water be employed as the oxidizand it will be further understood that small amounts of a halogen salt, as ferric chloride,
" which includes and the like, or an oxygenated salt, as potas sium chlorate and the like, may be used and which act catalytically to promote the liberation of oxides from the nitric acid.
It will be understood that in carrying out the method of my invention the degree of con centration of nitric acid used or the proportions of acid and water of the acid mixture and the temperatures, may be varied within wide limits without departing from my invention.
Having now fully what I claim and desire Patent is 1. The method of producing fenchone which includes oxidizing a pine oil out containing fenohyl alcohol with nitric acid and separating fenchone produced from other oxidation products.
2. The method of producing fenchone which includes subjecting a pine oil out containing fenohyl alcohol to heat in the presence of dilute nitric acid to efiect oxidation thereof and separating fenchone produced from other oxidation products.
3. The method of producing fenchone which includes fractionating pine oil to obtain a fraction containing about 75% fenchyl alcohol, subjecting the fraction to oxidation with nitric acid and separating the fenchone roduced from other oxidation products by distillation.
4.. The method of producing fenchone which includes fractionating pine oil to obtain a fraction boiling within about the range 196 C.-207 0., subjecting the fraction to oxidation with nitric acid and separating the fenchone produced from other oxidation products.
5. The method of producing fenchone which includes fractionating pine oil to obtain a fraction boiling within about the range 196 (1-207 C., subjecting the fraction to heat in the presence of nitric acid and separating the fenchone produced from other oxidation products.
6. The method of producing fenchone which includes fractionating pine oil to obtain a fraction boiling within about the range 196 C.2O7"v 0., subjecting the fraction to heat in the presence of nitric acid of a concentration within about the range 15%4:0% and separating the fenchone produced from other oxidation products.
7. The method of producing fenchone which includes oxidizing a pine oil out containing fenohyl alcohol with a mixture of nitric and sulphuric acids and separating described my invention, to protect by Letters products. 7
8. The method of producing fenchone fractionating pine oil to obtain a fraction rich in fenohyl alcohol, subjecting the, fraction to heat in the presence of a mixture of nitric and sulphuric acidsand 1 separating fenchone produced from other oxidation products.
9. The method which includes fractionating pine oil to obtain a fraction boiling within about the range 196 C.207 0., and oxidizing with a mixture of nitric and sulphuric acids and separating fenchone produced from other oxidation products. 7
10. The method of producing fenchone which includes subjecting a pine oil out rich in fenchyl alcohol to oxidation with a mixture of nitric acid and a mineral acid, and separating fenchone from other oxidation products produced.
11. The method of producing fenchone which includes subjecting a pine oil out rich in fenchyl alcohol to'oxidation with nitric acid in the presence of a substance which acts to promote the liberation of nitric oxide and separating fenchone from other oxidation products produced. a
12. The method of producing fenchone which includes subjecting a pine oil out rich in fenchyl alcohol to oxidation with nitric acid in the presence of a substance which acts catalytically to promote the liberation of nitric oxide and separating fenchone from other oxidation products produced.
13. The method of producing fenchone which includes subjecting a pine oil cut rich in fenchyl alcohol to oxidation with nitric acid in the presence of a mineral acid and separating fenchone from other oxidation products produced.
14. The method of producing fenchone which includes subjecting a pine oil out rich in fenchyl alcohol to oxidation With an oxidizing mixture including about 55% sul-' phuric acid, about 14% nitric acid and about 31% water and separating fenchone from other oxidation products produced.-
15. A method of producing fenchone which includes oxidizing a pine oil out containing fenchyl alcohol with nitric acid of a concentration within and separating fenchone produced from other oxidation products by distillation.
16. A method of producing fenchone which includes oxidizing a pine oil out boilin within about the range 196207 C. and containing fenchyl alcohol with nitric acid of a concentration within about the range 15 %40% and separating fenchone produced from other oxidation products.
In testimony of which invention, I have hereunto set my hand, at Kenvil, New Jersey, on this 9th day of January, 1928.
' IRVIN W. HUMPHREY. V
of producing fenchone the range 15%-40%'
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1876454A true US1876454A (en) | 1932-09-06 |
Family
ID=3424420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1876454D Expired - Lifetime US1876454A (en) | humphkjey |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1876454A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2894040A (en) * | 1953-09-28 | 1959-07-07 | Glidden Co | Isomerization of terpenic alcohols |
-
0
- US US1876454D patent/US1876454A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2894040A (en) * | 1953-09-28 | 1959-07-07 | Glidden Co | Isomerization of terpenic alcohols |
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