DE820302C - Process for the production of a new collection of trimethyl acetic acid (pivalic acid) - Google Patents
Process for the production of a new collection of trimethyl acetic acid (pivalic acid)Info
- Publication number
- DE820302C DE820302C DE1949P0036735 DEP0036735D DE820302C DE 820302 C DE820302 C DE 820302C DE 1949P0036735 DE1949P0036735 DE 1949P0036735 DE P0036735 D DEP0036735 D DE P0036735D DE 820302 C DE820302 C DE 820302C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- production
- acetic acid
- trimethyl acetic
- new collection
- 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
Links
- 238000000034 method Methods 0.000 title claims description 4
- OIKWZAMGBNHJCU-UHFFFAOYSA-N 2,2-dimethylpropanoic acid Chemical compound CC(C)(C)C(O)=O.CC(C)(C)C(O)=O OIKWZAMGBNHJCU-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- QEJPOEGPNIVDMK-UHFFFAOYSA-N 3-bromo-2,2-bis(bromomethyl)propan-1-ol Chemical compound OCC(CBr)(CBr)CBr QEJPOEGPNIVDMK-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VZHWENAYTHUKAS-UHFFFAOYSA-N 3,3,3-tribromo-2,2-dimethylpropanoic acid Chemical compound OC(=O)C(C)(C)C(Br)(Br)Br VZHWENAYTHUKAS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical class CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
-
- 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
- C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Abkömmlings der Trimethylessigsäure (Pivalinsäure) Symm. Tribromtrimethylessigsäure (a, y-Dibromß-brommethylpropan-ß-carbonsäure) war bisher noch nicht bekannt.Process for the preparation of a new derivative of trimethyl acetic acid (Pivalic acid) Symm. Tribromotrimethyl acetic acid (a, y-dibromos-bromomethylpropane-ß-carboxylic acid) was not yet known.
Es wurde gefunden, daß man diese Verbindung erhält, wenn man Pentaerythrittribromhydrin mit sauren Oxydationsmitteln, vorzugsweise mit Salpetersäure, oxydiert.It has been found that this compound is obtained by using pentaerythritol tribromohydrin oxidized with acidic oxidizing agents, preferably with nitric acid.
Der nach vorliegendem Verfahren zugängliche neue Abkömmling der Pivalinsäure soll als Zwischenprodukt zur Herstellung therapeutisch verwertbarer Stoffe dienen.The new derivative of pivalic acid accessible by the present process is intended to serve as an intermediate product for the manufacture of therapeutically usable substances.
Beispiel 16,2g Pentaerythrittribromhydrin werden in ein Gemisch aus 6o g 98 bis ioo°!oiger Salpetersäure und 20 g Wasser unter gutem Rühren bei 8o bis 9o° portionsweise eingetragen. Dann wird noch so lange weiter erwärmt, bis die Entwicklung von Stickoxyden praktisch aufgehört hat. Beim Erkalten erstarrt die in der Wärme zum Teil als 01 ausgeschiedene symm. Tribrompivalinsäure vollkommen kristallin. Man verdünnt mit etwa ioo ccm Wasser, saugt ab, wäscht gut mit Wasser nach und trocknet. Ausbeute 13,5 g. Durch Umkristallisieren aus Benzol oder Gasohn erhält man sie rein vom F. = 98 bis 99°. Das Säurechlorid schmilzt nach dem Umkristallisieren aus Petrolä.ther bei 112 bis 114'; der Methylester aus dem Chlorid in üblicher Weise gewonnen, hat den F. = 47 bis 49°.Example 16.2 g of pentaerythritol tribromohydrin are added in portions to a mixture of 60 g of 98 to 100% nitric acid and 20 g of water with thorough stirring at 80 to 90 °. Then the heating continues until the development of nitrogen oxides has practically stopped. When it cools down, the symm, partly excreted as 01 in the warmth, solidifies. Tribromopivalic acid completely crystalline. It is diluted with about 100 cc of water, filtered off with suction, washed thoroughly with water and dried. Yield 13.5g. Recrystallization from benzene or gasoline gives them a pure temperature of 98 to 99 °. After recrystallization from petroleum ether, the acid chloride melts at 112 to 114 '; the methyl ester obtained from the chloride in the usual way has a F. = 47 to 49 °.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1949P0036735 DE820302C (en) | 1949-03-15 | 1949-03-15 | Process for the production of a new collection of trimethyl acetic acid (pivalic acid) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1949P0036735 DE820302C (en) | 1949-03-15 | 1949-03-15 | Process for the production of a new collection of trimethyl acetic acid (pivalic acid) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE820302C true DE820302C (en) | 1951-11-08 |
Family
ID=578919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1949P0036735 Expired DE820302C (en) | 1949-03-15 | 1949-03-15 | Process for the production of a new collection of trimethyl acetic acid (pivalic acid) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE820302C (en) |
-
1949
- 1949-03-15 DE DE1949P0036735 patent/DE820302C/en not_active Expired
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