DE1543823B - Process for the preparation of 2,4-dihydroxybenzophenone - Google Patents
Process for the preparation of 2,4-dihydroxybenzophenoneInfo
- Publication number
- DE1543823B DE1543823B DE1543823B DE 1543823 B DE1543823 B DE 1543823B DE 1543823 B DE1543823 B DE 1543823B
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen chloride
- resorcinol
- reaction
- mixture
- dihydroxybenzophenone
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 30
- JFDZBHWFFUWGJE-UHFFFAOYSA-N Benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 235000005074 zinc chloride Nutrition 0.000 claims description 7
- 239000011592 zinc chloride Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000007792 addition Methods 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- 238000006460 hydrolysis reaction Methods 0.000 claims 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims 3
- 239000007795 chemical reaction product Substances 0.000 claims 3
- 238000003309 Hoesch reaction Methods 0.000 claims 2
- -1 aryl carboxylic acid Chemical class 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-dimethylhexa-2,4-diene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 claims 1
- DWVXFVWWARTDCQ-UHFFFAOYSA-N 2-ethylbenzene-1,3-diol Chemical compound CCC1=C(O)C=CC=C1O DWVXFVWWARTDCQ-UHFFFAOYSA-N 0.000 claims 1
- 229960000583 Acetic Acid Drugs 0.000 claims 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N Benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
- CODNYICXDISAEA-UHFFFAOYSA-N Bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- 241000282941 Rangifer tarandus Species 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000006053 organic reaction Methods 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000002194 synthesizing Effects 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
Description
Nach dem Abtreiben von flüchtigen Stoffen aus dem Reaktionsgemisch, vorzugsweise durch Wasserdampfdestillation, wird das Gemisch gekühlt und filtriert. Das als Filterrückstand erhaltene 2,4-Dihydroxybenzophenon wird mit Wasser gewaschen und getrocknet.After driving off volatile substances from the reaction mixture, preferably by steam distillation, the mixture is cooled and filtered. The 2,4-dihydroxybenzophenone obtained as filter residue is washed with water and dried.
Die Menge an Benzonitril muß bei dem erfindungsgemäßen Verfahren mindestens 2 Mol je Mol Resorcin betragen. Eine Menge von 2 Mol reicht aus, um die höchsten Ausbeuten zu erzielen, und wird daher bevorzugt. Wenn sich Schwierigkeiten beim Rühren des Reaktionsgemisches ergeben, kann man auch größere Mengen als 2 Mol Benzonitril je Mol Resorcin zusetzen, in welchem Fall das überschüssige Benzonitril als Verdünnungsmittel wirkt. Der Zusatz von mehr als 4 Mol Benzonitril je Mol Resorcin ist gewöhnlich unnötig.The amount of benzonitrile in the process according to the invention must be at least 2 moles per mole of resorcinol be. An amount of 2 moles is sufficient to achieve the highest yields and is therefore preferred. If there are difficulties in stirring the reaction mixture, larger ones can be used Add amounts of more than 2 moles of benzonitrile per mole of resorcinol, in which case the excess benzonitrile as a diluent works. The addition of more than 4 moles of benzonitrile per mole of resorcinol is usually unnecessary.
Die einzusetzende Menge an Zinkchlorid beträgt 0,3 bis 1 Mol je Mol Resorcin.The amount of zinc chloride to be used is 0.3 to 1 mole per mole of resorcinol.
2,4-Dihydroxybenzophenon wird als Absorptionsmittel für ultraviolettes Licht in Harzen und Kunststoffen, wie Polystyrol, Polymerisaten des Acrylsäurenitrils sowie Polymerisaten und Mischpolymerisaten von Acrylsäure- und Methacrylsäureestern, verwendet. Es eignet sich auch als Zwischenprodukt für die Herstellung anderer Ultraviolett-Absorptionsmittel, z. B. verschiedener Ätherderivate.2,4-Dihydroxybenzophenone is used as an absorbent for ultraviolet light in resins and plastics, such as polystyrene, polymers of acrylonitrile and polymers and copolymers of acrylic acid and methacrylic acid esters, used. It is also suitable as an intermediate for manufacturing other ultraviolet absorbers, e.g. B. various ether derivatives.
In dem folgenden Beispiel beziehen sich die Teile auf Gewichtsmengen.In the following example, the parts refer to amounts by weight.
165 Teile (1,5 Mol) Resorcin und 120Teile (0,74 Mol) wasserfreies Zinkchlorid werden zu 309 Teilen (3,0 Mol) Benzonitril zugesetzt, und das Gemisch wird 1J2 Stunde bei etwa 25 bis 30° C gerührt. Dann wird im Verlauf mehrerer Stunden gasförmiger Chlorwasserstoff eingeleitet, bis das Reaktionsgemisch gesättigt ist oder insgesamt etwa 95 bis 109 Teile (2,6 bis 3,0 Mol) Chlorwasserstoff absorbiert hat. Das Reaktionsgemisch wird 8 Stunden auf 50°C gehalten, wobei man den sich entwickelnden Chlorwasserstoff entweichen läßt. Dann setzt man allmählich 800 Teile kaltes Wasser zu und rührt das Reaktionsgemisch mehrere Stunden bei Raumtemperatur. Hierauf wird das Reaktionsgemisch der Wasserdampfdestillation unterworfen, um flüchtige Produkte abzutreiben. Dann wird das Gemisch gekühlt und das 2,4-Dihydroxybenzophenon abfiltriert, mit Wasser gewaschen und getrocknet. Man erhält 300 Teile 2,4-Dihydroxybenzophenon (Ausbeute 93,3 %> bezogen auf dss eingesetzte Resorcin) mit einem Schmelzpunkt von 143 bis 144° C und einem Rein-165 parts (1.5 moles) of resorcinol and 120Teile (0.74 mole) of anhydrous zinc chloride are added to 309 parts (3.0 mol) of benzonitrile, and the mixture is stirred for 1 J 2 hours at about 25 to 30 ° C. Gaseous hydrogen chloride is then passed in over the course of several hours until the reaction mixture is saturated or a total of about 95 to 109 parts (2.6 to 3.0 mol) of hydrogen chloride has been absorbed. The reaction mixture is kept at 50 ° C. for 8 hours, during which the hydrogen chloride which is evolved is allowed to escape. 800 parts of cold water are then gradually added and the reaction mixture is stirred for several hours at room temperature. The reaction mixture is then subjected to steam distillation in order to drive off volatile products. The mixture is then cooled and the 2,4-dihydroxybenzophenone is filtered off, washed with water and dried. 300 parts of 2,4-dihydroxybenzophenone are obtained (yield 93.3%> based on the resorcinol used) with a melting point of 143 to 144 ° C and a pure
heitsgrad von 97 %· "degree of 97% "
Claims (2)
von Acylresorcinen durch Kondensieren von Säure- Beim Zusatz des Chlorwasserstoffs wird die Tempe-From Recueil des Travaux chimiques des Pays-bas 50, decisive and can rise within the limits set by the Reak-1931, pp. 848 to 850 is a method for the production of 45 tion vessel,
of acylresorcins by condensation of acid- When the hydrogen chloride is added, the temperature
Family
ID=
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0154092A1 (en) * | 1984-03-02 | 1985-09-11 | Gaf Corporation | Process for the preparation of 2,4-dihydroxybenzophenones |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0154092A1 (en) * | 1984-03-02 | 1985-09-11 | Gaf Corporation | Process for the preparation of 2,4-dihydroxybenzophenones |
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