CH206595A - Process for the preparation of a mixture of ring-alkylated aromatic compounds. - Google Patents
Process for the preparation of a mixture of ring-alkylated aromatic compounds.Info
- Publication number
- CH206595A CH206595A CH206595DA CH206595A CH 206595 A CH206595 A CH 206595A CH 206595D A CH206595D A CH 206595DA CH 206595 A CH206595 A CH 206595A
- Authority
- CH
- Switzerland
- Prior art keywords
- mixture
- ring
- preparation
- aromatic compounds
- alkylated aromatic
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 12
- 150000001491 aromatic compounds Chemical class 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229960004424 carbon dioxide Drugs 0.000 claims description 3
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 eines Gemisches kernalkylierter aromatischer Verbindungen. Bei der katalytischen Reduktion des Koh lenoxydes bezw. kohlenoxydhaltiger Gase mit Wasserstoff entstehen neben Methanol eine Reihe höherer Alkohole mit verzweigter Koh- lenstoffkette und einer Kettenlänge von etwa C5-C12, aus denen sich durch Dehydrati- sierung und Polymerisierung ein Gemisch höherer Olefine herstellen lässt.
Es wurde gefunden, dass man durch Ein wirkung der von 180-2200 C siedenden Fraktion eines solchen polymerisierten Ole- fingemisches auf Phenoxyessigsäure in guter Ausbeute ein Gemisch kernalkylierter Phen- oxyessigsäuren erhält.
Als Katalysatoren können die bekannten Substanzen, wie Borfluorid und seine Mole külverbindungen, Aluminiumchlorid, Schwe felsäure u. a., dienen.
Das so erhaltene Säuregemisch kann als Textilhilfsmittel oder als Ausgangsmaterial hierfür verwendet werden. Beispiel: 152 Gewichtsteile Phenoxyessigsäure wer den bei<B>700</B> C in 800 Gewichtsteilen Tetra chlorkohlenstoff gelöst und 30 Gewichtsteile Borfiuorid eingeleitet.
Dann werden bei 60 C 185 Gewichtsteile Olefin von den Siedegren zen 180--2200, das durch Dehydratisierung und Polymerisierung der bei der katalytischen Reduktion von Kohlenoxyd oder kohlenoxyd- haltiger Gase entstehenden Alkohole mit etwa 5-12 C-Atomen gewonnen wird, eingetragen. Man rührt zwei Stunden lang bei 60 C und 15 Stunden lang bei Zimmertemperatur. Nach dem Waschen des Reaktionsproduktes mit Wasser und dem Trocknen geht das Gemisch der Alkylplsenoxyessigsäureri im Vakuum von 2 mm bei 170-225 C über.
Ausbeute 87'/0 der Theorie.
Das so gebildete Alkylphenoxyessigsäure- gemisch bildet ein hellgelbes, viskoses<B>01,</B> das in Sodalösung löslich ist.
Process for the preparation of a mixture of ring-alkylated aromatic compounds. In the catalytic reduction of the Koh lenoxydes respectively. Carbon-oxide-containing gases with hydrogen, in addition to methanol, produce a number of higher alcohols with a branched carbon chain and a chain length of around C5-C12, from which a mixture of higher olefins can be produced by dehydration and polymerisation.
It has been found that the action of the fraction boiling from 180-2200 C of such a polymerized olefin mixture on phenoxyacetic acid gives a mixture of ring-alkylated phenoxyacetic acids in good yield.
As catalysts, the known substances such as boron fluoride and its Mole külverbindungen, aluminum chloride, sulfuric acid and. a., serve.
The acid mixture thus obtained can be used as a textile auxiliary or as a starting material for this. Example: 152 parts by weight of phenoxyacetic acid are dissolved in 800 parts by weight of carbon tetrachloride at 700 C and 30 parts by weight of boron fluoride are introduced.
Then 185 parts by weight of olefins with a boiling point of 180--2200, which is obtained by dehydrating and polymerizing the alcohols with about 5-12 carbon atoms formed during the catalytic reduction of carbon oxides or gases containing carbon oxides, are introduced at 60 C. The mixture is stirred for two hours at 60 ° C. and for 15 hours at room temperature. After the reaction product has been washed with water and dried, the mixture of alkylplsenoxyacetic acids passes over in a vacuum of 2 mm at 170-225 ° C.
Yield 87% of theory.
The resulting alkylphenoxyacetic acid mixture forms a pale yellow, viscous 01, which is soluble in soda solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE206595X | 1936-09-09 | ||
| CH200981T | 1937-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH206595A true CH206595A (en) | 1939-08-15 |
Family
ID=25723611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH206595D CH206595A (en) | 1936-09-09 | 1937-09-03 | Process for the preparation of a mixture of ring-alkylated aromatic compounds. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH206595A (en) |
-
1937
- 1937-09-03 CH CH206595D patent/CH206595A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2088018A (en) | Oxygenated compounds derived from butyraldehyde and its derivatives | |
| DE941909C (en) | Process for the preparation of N, N'-diaethanol-piperazine | |
| CH206595A (en) | Process for the preparation of a mixture of ring-alkylated aromatic compounds. | |
| CH206596A (en) | Process for the preparation of a mixture of ring-alkylated aromatic compounds. | |
| US1717105A (en) | Process for preparing hexylresorcinol | |
| CH206606A (en) | Process for the preparation of a mixture of ring-alkylated aromatic compounds. | |
| DE965696C (en) | Process for the preparation of esters of glycol mono- (oxymethyl) ethers | |
| EP0128489B1 (en) | Process for the preparation of dialkyl esters of succinylsuccinic acid | |
| DE2332064C2 (en) | Process for the preparation of 2-hydroxynaphthalene-3-carboxylic acid | |
| CH200981A (en) | Process for the preparation of a mixture of ring-alkylated aromatic compounds. | |
| DE1470264C3 (en) | Process for the preparation of 1-phenyl-1 - square brackets on thienyl- (2) square brackets to -carbinols | |
| DE881340C (en) | Process for the production of adipic dinitrile | |
| DE922167C (en) | Process for the preparation of cyclohexylidenecyclohexanones | |
| DE947966C (en) | Process for the preparation of 2,6-di-tert-butylnaphthalene | |
| AT201582B (en) | Process for the preparation of new dimethylaminopropoxybenzenes | |
| CH206607A (en) | Process for the preparation of a mixture of ring-alkylated aromatic compounds. | |
| DE767014C (en) | Process for the preparation of alkylated aromatic sulfonic acid salts | |
| CH217132A (en) | Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. | |
| DE819400C (en) | Process for the preparation of 1-phenyl-2-aminopropane or its N-substituted derivatives | |
| DE947308C (en) | Process for the production of hydroquinone | |
| CH394241A (en) | Process for the production of D-tocopherol | |
| AT227387B (en) | Process for the preparation of new 1-methyl-17α-alkyl-δ <1> -androsten-17β-ol-3-ones | |
| CH204700A (en) | Process for the production of a condensation product. | |
| CH118005A (en) | Process for the production of an amorphous mass from acetylene and crude benzene. | |
| DE2031921B2 (en) | Process for the production of isoprene by dehydrating 3-methyl-3-buten-1-ol |