CH206406A - Process for the preparation of isooctylphenoxyacetic acid. - Google Patents
Process for the preparation of isooctylphenoxyacetic acid.Info
- Publication number
- CH206406A CH206406A CH206406DA CH206406A CH 206406 A CH206406 A CH 206406A CH 206406D A CH206406D A CH 206406DA CH 206406 A CH206406 A CH 206406A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- isooctylphenoxyacetic
- agents
- preparation
- parts
- Prior art date
Links
- MDWYCQRDUIDRDN-UHFFFAOYSA-N 8-methyl-2-phenoxynonanoic acid Chemical compound C(CCCCC(C)C)C(C(=O)O)OC1=CC=CC=C1 MDWYCQRDUIDRDN-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 2
- 239000012459 cleaning agent Substances 0.000 claims description 2
- 238000006471 dimerization reaction Methods 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229910015900 BF3 Inorganic materials 0.000 description 4
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- MFFYGSJLZRPNLQ-UHFFFAOYSA-N 2-phenoxydecanoic acid Chemical compound CCCCCCCCC(C(O)=O)OC1=CC=CC=C1 MFFYGSJLZRPNLQ-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung -von Isooctylphenogyessigsäure. Es wurde gefunden, dass man Isooctyl- phenoxyessigsäure entsprechend der Formel:
EMI0001.0005
in besonders vorteilhafter Weise herstellen kann, wenn man das bei der Dimerisation von tert. Isobutylen entstehende Gemisch von isomeren Diisobutylenen, welchen die Formeln
EMI0001.0011
zukommen, in Gegenwart von Kondensations mitteln auf Phenoxyessigsäure einwirken lässt.
Die erhaltene Isooctylphenoxyessigsäure bil- det nach dem Umkristallisieren aus Benzin feine weisse Nadeln (P. P. 106-108') und stellt auch als Rohprodukt ein mit Vorteil zu verwendendes Textilhilfsmittel, z. B. Netz-, Reinigungs- oder Dispergiermittel dar.
Das Verfahren wird zum Beispiel so aus geführt, dass molekulare Mengen Phenoxyessig- , säure und Diisobutylen zusammen erhitzt werden, bis eine klare Lösung entsteht. Dann wird das Kondensationsmittel, z. B. Bortri- fluorid oder dessen Molekülverbindungen oder Zinkchlorid, zugegeben. Nachdem einige Zeit nacherhitzt worden ist, wird abgekühlt und mit Wasser gewaschen. Bei der Reaktion können auch indifferente Lösungsmittel mit verwendet werden, wobei man das Konden sationsmittel entweder vor dem Eintragen des Diisobutylens oder danach zugeben kann.
<I>Beispiele:</I> 1. 152 Gewichtsteile Phenoxyessigsäure werden in 500 Volumteilen Tetrachlorkohlen- stoff bei 80 gelöst und 8 Gewichtsteile Bor- fluorid eingeleitet. Dann gibt man 112 Ge wichtsteile Diisobutylen vom Siedepunkt 101-1040 zu und rührt 8 Stunden bei 60 bis<B>70'</B> nach. Mit Wasser wird das Bor- fluorid ausgewaschen und der Tetrachlor- kohlenstoff abgedampft.
Die nach dem Ab dampfen des Tetrachlorkohlenstoffes häufig schon kristallin anfallende Octylphenoxy- essigsäure kann durch Vakuumdestillation ge reinigt werden.
Die durch Umkristallisieren aus Benzin (Kp. 60-100 ) gereinigte Octylpherroxyessig- säure fällt in feinen weissen Nadeln vom F. 106-1081' aus. Der Mischschmelzpunkt mit Octylpherroxyessigsäure, die aus p-Octyl- phenol und Cl-CH,-COOH dargestellt wurde, ergab keine Depression. Die Bestim mung der Säurezahl ergab 214,2 gegenüber einem berechneten Wert von 212,1.
2. 152 Gewichtsteile Phenoxyessigsäure werden mit 112 Gewichtsteilen Diisobrrtylen auf<B>100-1050</B> erhitzt. Dann werden 8 Teile Bortrifluorid eingeleitet, wobei man durch Kühlung die Temperatur nicht über<B>1100</B> steigen lässt. Bei fallender Temperatur rührt man 5 Stunden nach und arbeitet dann in der im Beispiel 1 beschriebenen Weise auf.
Process for the production of isooctylphenogyacetic acid. It was found that isooctylphenoxyacetic acid according to the formula:
EMI0001.0005
can be produced in a particularly advantageous manner if the tert in the dimerization of. Isobutylene resulting mixture of isomeric diisobutylenes, which the formulas
EMI0001.0011
come to act in the presence of condensation agents on phenoxyacetic acid.
The isooctylphenoxyacetic acid obtained forms fine white needles after recrystallization from gasoline (P. P. 106-108 ') B. wetting agents, cleaning agents or dispersants.
The process is carried out, for example, in such a way that molecular amounts of phenoxyacetic acid, acid and diisobutylene are heated together until a clear solution is obtained. Then the condensing agent, e.g. B. boron trifluoride or its molecular compounds or zinc chloride added. After heating for some time, it is cooled and washed with water. Indifferent solvents can also be used in the reaction, and the condensation agent can be added either before the diisobutylene is introduced or afterwards.
<I> Examples: </I> 1. 152 parts by weight of phenoxyacetic acid are dissolved in 500 parts by volume of carbon tetrachloride at 80 and 8 parts by weight of boron fluoride are introduced. 112 parts by weight of diisobutylene with a boiling point of 101-1040 are then added and the mixture is subsequently stirred for 8 hours at 60 to 70 '. The boron fluoride is washed out with water and the carbon tetrachloride is evaporated.
The octylphenoxyacetic acid, which often occurs in crystalline form after the carbon tetrachloride has evaporated, can be purified by vacuum distillation.
The octylpherroxyacetic acid, purified by recrystallization from gasoline (bp 60-100), precipitates in fine white needles with a mp of 106-1081 '. The mixed melting point with octylpherroxyacetic acid, which was prepared from p-octylphenol and Cl-CH, -COOH, did not result in any depression. The determination of the acid number was 214.2 compared to a calculated value of 212.1.
2. 152 parts by weight of phenoxyacetic acid are heated to <B> 100-1050 </B> with 112 parts by weight of diisocyanate. 8 parts of boron trifluoride are then introduced, the temperature not being allowed to rise above 1100 by cooling. As the temperature falls, the mixture is subsequently stirred for 5 hours and then worked up in the manner described in Example 1.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE270237X | 1937-02-27 | ||
| CH206406T | 1938-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH206406A true CH206406A (en) | 1939-08-15 |
Family
ID=25724298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH206406D CH206406A (en) | 1937-02-27 | 1938-01-24 | Process for the preparation of isooctylphenoxyacetic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH206406A (en) |
-
1938
- 1938-01-24 CH CH206406D patent/CH206406A/en unknown
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