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EP0000162B1 - Verfahren zur Herstellung von Aralkyl- und Alkyl-phenol-äthern - Google Patents

Verfahren zur Herstellung von Aralkyl- und Alkyl-phenol-äthern Download PDF

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Publication number
EP0000162B1
EP0000162B1 EP19780100182 EP78100182A EP0000162B1 EP 0000162 B1 EP0000162 B1 EP 0000162B1 EP 19780100182 EP19780100182 EP 19780100182 EP 78100182 A EP78100182 A EP 78100182A EP 0000162 B1 EP0000162 B1 EP 0000162B1
Authority
EP
European Patent Office
Prior art keywords
parts
radical
radicals
carbonate
carbon atoms
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
Application number
EP19780100182
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0000162A1 (de
Inventor
Franz Dr. Merger
Friedrich Dr. Towae
Ludwig Dr. Schroff
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE19772729031 external-priority patent/DE2729031A1/de
Priority claimed from DE19782807762 external-priority patent/DE2807762A1/de
Application filed by BASF SE filed Critical BASF SE
Publication of EP0000162A1 publication Critical patent/EP0000162A1/de
Application granted granted Critical
Publication of EP0000162B1 publication Critical patent/EP0000162B1/de
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form

Definitions

  • the invention relates to a new process for the preparation of phenol ethers by reacting phenols with dialkyl carbonates in the presence of tertiary amines and / or phosphines.
  • the reaction can be represented by the following formulas: Compared to the known processes, the process according to the invention provides a large number of phenol ethers in good yield and purity in a simpler and more economical way. Cumbersome separation and neutralization operations as well as corrosion problems are avoided.
  • the dialkyl carbonates can be prepared in a known manner, for example by the processes specified in German Offenlegungsschrift 2,160,111 or more expediently, in particular for reasons of environmental protection, by reacting an alcohol with carbon monoxide and oxygen in the presence of copper catalysts in accordance with that described in German Offenlegungsschrift 2,334,736 Process to be produced.
  • the starting phenols can carry 3 or 2 hydroxyl groups and preferably a convertible hydroxyl group.
  • Preferred starting materials II and III and accordingly preferred end products I are those in the formulas of which the individual radicals R 'can be the same or different and each represent a hydrogen atom, a hydroxyl group or the radical -OR 2 , or both radicals R t together with two each other neighboring carbon atoms of the benzene ring can also represent a fused phenylene radical, the individual radicals R 2 can be the same or different and each denotes an aralkyl radical with 7 to 12 carbon atoms or in particular an alkyl radical with 1 to 7, advantageously 1 to 4 carbon atoms, the individual R 3 radicals can be the same or different and each represents a phenyl radical, an aralkyl radical with 7 to 12 carbon atoms or in particular an alkyl radical with 1 to 12, advantageously 1 to 6 carbon atoms, an alkenyl radical with 2 to 12, advantageously with 2 to 6 carbon atoms and preferably a double bond, an Al substituted by 2 oxo groups kylrest
  • radicals can also be substituted by groups which are inert under the reaction conditions, for example alkyl groups or alkoxy groups each having 1 to 4 carbon atoms.
  • Aliphatic radicals are also those whose alkyl radicals are substituted by oxo groups, for example acyl, aldehydo and carbalkoxy groups.
  • the starting materials 11 are reacted with the starting materials III in a stoichiometric amount or in excess or deficit, advantageously in the case of the reaction of monohydroxy compounds II from 1 to 10 moles, in particular from 1.2 to 5 moles of starting material III per mole of starting material II or in the case of Conversion of dihydroxy compounds II to monohydroxymonoether compounds I from 0.1 to 2, in particular from 0.2 to 1 mole of starting material III per mole of starting material II, or in the case of converting dihydroxy compounds II to diether I from 2 to 10, in particular from 2 to 5, moles Starting material III per mole of starting material II or in the case of the conversion of trihydroxy compounds II to dihydroxymonoether compounds I from 0.1 to 2, in particular from 0.2 to 1 mole of starting material III per mole of starting material II or in the case of the reaction of trihydroxy compounds II to monohydroxy diethyl compounds I of 2 , 01 to 4, in particular from 2.1 to 3 moles of starting material III per mole of starting material II or in the case e the conversion
  • Examples of possible starting materials II are: phenol; in 2-position, 3-position, 4-position, 5-position and / or 6-position single, double, triple or quadruple with the same or different substituents by the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, benzyl, phenyl, cyano, nitro, formyl, acetyl, propionyl, butyryl group, by bromine.
  • Chlorine through the ⁇ -formylethyl, ⁇ -formylpropyl, 8-formylbutyl, ß-acetylethyl, y-acetylpropyl, ⁇ -acetylbutyl, ⁇ -propionylethyl, yPropionylpropyl, b-propionylbutyl, methylcarbonylcarbonyloxy, -, Propylcarbonyloxy-, Isopropylcarbonyloxy-, Butylcarbonyloxy-, Isobutylcarbonyloxy-, sec.-Butylcarbonyloxy-, tert.-Butylcarbonyloxy-, Phenylcarbonyloxy-, Carbmethoxy-, Carbäthoxy-, Carbpropoxy-, Carbisopropoxy-, Carbbutoxy-, Carbisobutoxy- .-Butoxy, carb-tert-butoxy, carbphenoxy, methylthio, e
  • Preferred starting materials ii are: phenol, o-, m-, p-cresol, o-, m-, p-ethylphenol, 2,3-, 2,4-, 2,5-, 2,6-, 3,5 -, 3,4-xylenol, o-, m-, p-isopropylphenol, 2,4-, 2,6-dimethylphenol, 2,4,6-trimethylphenol, 2-methyl-5-isopropylphenol, 3-methyl-6 -isopropylphenol, o-, m-, p-tert-butylphenol, p-tert-butylphenol, octylphenol, nonylphenol, dodecylphenol, 2,6-, 2,4-di-tert-butylphenol, 3-methyl-4 , 6-di-tert-butylphenol, salicyl alcohol, salicylaldehyde, methyl salicylic acid, vanillin, methyl gallic acid, eugen
  • Possible starting materials III are: dimethyl carbonate, diethyl carbonate, di-n-propyl carbonate, di-n-butyl carbonate, diisobutyl carbonate, dibenzyl carbonate, methyl ethyl carbonate, methyl propyl carbonate, ethyl propyl carbonate; dimethyl carbonate, diethyl carbonate, di-n-propyl carbonate, methyl ethyl carbonate, dibenzyl carbonate are preferred.
  • the reaction is carried out at a temperature above 100 ° C, generally between 100 ° C and 350 ° C, preferably from 120 to 300 ° C, in the case of monohydroxy compounds II advantageously from 120 to 200, in particular from 130 to 180 ° C; in the case of the production of monoether compounds I, starting from dihydroxy compounds II or trihydroxy compounds II, advantageously from 100 to 170, in particular from 110 to 150 ° C; in the case of the manufacture of Diether I and Triusch I, starting from.
  • Dihydroxy compounds II or trihydroxy compounds II advantageously from 120 to 200, in particular from 140 to 180 ° C., unpressurized or under pressure, preferably under the vapor pressure of the reaction mixture which is established in the autoclave at the aforementioned temperatures, advantageously from 1 to 200 bar, continuously or batchwise .
  • the reaction mixture expediently serves simultaneously as a solution medium or suspension medium. In such cases it is sometimes advantageous to add an excess of starting material III and / or to add an amount of the alcohol formed during the reaction at the beginning.
  • solvents which are inert under the reaction conditions can be used, in particular when preparing the monohydroxy compounds from the dihydroxy compounds. Examples of solvents are in question: aromatic hydrocarbons, e.g.
  • Heptane nonane, gasoline fractions within a boiling point interval of 70 to 190 ° C, cyclohexane, methylcyclohexane, decalin, petroleum ether, hexane, ligroin, 2,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane , Octane; and corresponding mixtures.
  • the solvent is expediently used in an amount of 100 to 2,000 percent by weight, based on starting material III.
  • a tertiary amine is used as the catalyst, advantageously in an amount of 0.1 to 10, in particular 1 to 5, mol percent, based on starting material II. Mixtures of the catalysts mentioned are also suitable for the reaction.
  • the amine can also be used in the form of diamines, corresponding salts or a quaternary salt.
  • Suitable catalysts are trimethylamine, dimethylamino-neopentanol, N, N'-tetramethyldiamino-neopentane, ethyldimethylamine, lauryldimethylamine, stearyldimethylamine, pyridine, ⁇ -, ⁇ - and ⁇ -picoline, quinoline, isoquinoline, quinazoline, quinoxaline, amyldimethylamine, amyldimethylamine , N-methylimidazole, N-methylpyrrole, 2,6- and 2,4-lutidine, triethylenediamine, p-dimethylaminopyridine, N, N-dimethylcyclohexylamine, pyrimidine, acridine; Di- (methyl) -, di (ethyl) -, di- (n-propyl) -, di- (n-butyl) -, di- (pentyl) -, di- (n
  • Trimethylamine, pyridine, ⁇ -picoline are particularly advantageous.
  • 4-pyrrolidino (1 ') pyridine and other pyridine derivatives such as o-methyl, m-methyl, o-ethyl, m-ethyl, p-ethyl, o-propyl, m-propyl, p -Propylpyridine, dimethylamino-neopentanol, N, N'-tetramethyldiamino-neopentane, p-methoxy, p-ethoxy, p-propoxy-pyridine, p-dimethylaminopyridine, p-diethyl aminopyridine, p-dipropylaminopyridine, 4-polyvinylpyridine.
  • a tertiary phosphine is also used as the catalyst, advantageously in an amount of 0.1 to 10, in particular 1 to 5, mol percent of tertiary phosphine, based on starting material 11. Mixtures of the catalysts mentioned are also suitable for the reaction.
  • the phosphine can also be used in the form of diphosphine.
  • Suitable catalysts are those of the formula wherein the individual radicals R B can be the same or different and each an aliphatic or aromatic radical, preferably an alkyl radical having 1 to 6 carbon atoms, an alkyl radical substituted by several cyano groups or preferably a cyano group having 2 to 9 carbon atoms, a phenyl radical or one by one or 2 alkyl groups each having 1 to 4 carbon atoms and / or one or 2 alkoxy groups each having 1 to 4 carbon atoms substituted phenyl radical, R 7 denotes an aliphatic radical, preferably an alkylene radical with 1 to 6 carbon atoms.
  • radicals can also be substituted by groups which are inert under the reaction conditions, for example by alkyl groups or alkoxy groups each having 1 to 4 carbon atoms, carboxy groups having 2 to 4 carbon atoms.
  • phosphines IV and V are suitable as catalysts: trimethylphosphine, triethylphosphine, tripropylphosphine, triisopropylphosphine, tributylphosphine, triisobutylphosphine, tri-sec-butylphosphine, triphenylphosphine; P, P-dimethyl-P-neopentylphosphine, P-ethyl-P, P-dimethylphosphine, P-lauryl-P, P-dimethylphosphine, P-stearyl-P, P-dimethylphosphine, P-amyl-P, P-dimethylphosphine, P-prop
  • the reaction can be carried out as follows: A mixture of the starting materials II, 111, the catalyst and optionally the solvent is kept at the reaction temperature for 1 to 20 hours. The end product is then made from the mixture in a conventional manner, e.g. by fractional distillation.
  • aralkylaryl and alkylaryl ethers which can be prepared by the process of the invention are valuable starting materials for the production of dyes, crop protection agents and fragrances.
  • the reaction is carried out analogously to Example 1 with 18.4 parts of methyl gallate and 80 parts of dimethyl carbonate. 16.5 parts (76% of theory) of 3,4,5-trimethoxybenzoic acid methyl ester of bp 60 to 63 ° C./0.07 mbar are obtained. The turnover is 96 percent.
  • the reaction is carried out analogously to Example 1 with 22.8 parts of 5-methylresorcinol and 9 parts of dimethyl carbonate. 9 parts (98%) of theory) of 5-methylresorcinol monomethyl ether of bp 63 to 65 ° C./0.4 mbar are obtained. The turnover is 36 percent.
  • hydroquinone 22 parts are kept at 190 ° C. for 15 hours with 18 parts of dimethyl carbonate and one part of triphenylphosphine.
  • Working up is carried out analogously to Example 23. 3 parts (97% of theory, based on converted hydroquinone) of hydroquinone monomethyl ether, mp 57 ° C., are obtained. The turnover is 12 percent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP19780100182 1977-06-28 1978-06-19 Verfahren zur Herstellung von Aralkyl- und Alkyl-phenol-äthern Expired EP0000162B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19772729031 DE2729031A1 (de) 1977-06-28 1977-06-28 Verfahren zur herstellung von aralkyl- und alkyl-phenolaethern
DE2729031 1977-06-28
DE19782807762 DE2807762A1 (de) 1978-02-23 1978-02-23 Verfahren zur herstellung von aralkyl- und alkyl-phenolaethern
DE2807762 1978-02-28

Publications (2)

Publication Number Publication Date
EP0000162A1 EP0000162A1 (de) 1979-01-10
EP0000162B1 true EP0000162B1 (de) 1980-08-20

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP19780100182 Expired EP0000162B1 (de) 1977-06-28 1978-06-19 Verfahren zur Herstellung von Aralkyl- und Alkyl-phenol-äthern

Country Status (5)

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US (1) US4192949A (it)
EP (1) EP0000162B1 (it)
JP (1) JPS5412331A (it)
DE (1) DE2860227D1 (it)
IT (1) IT1096588B (it)

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JP3870385B2 (ja) * 1997-10-20 2007-01-17 冨士薬品工業株式会社 水溶性フォトレジスト組成物
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US6596877B2 (en) * 2001-10-17 2003-07-22 Novartis Ag Accelerated process for preparing O-methyl phenols, N-methyl heteroaromatic compounds, and methylated aminophenols
US6686507B2 (en) 2002-03-06 2004-02-03 Pfizer Inc Purification of 2-methoxy-5-trifluoromethoxybenzaldehyde
WO2009158644A2 (en) * 2008-06-27 2009-12-30 Futurefuel Chemical Company Systems and methods for the preparation of alkyl aryl ethers
CN102351663B (zh) * 2011-09-29 2015-03-04 南京林业大学 一种丁香酚甲醚的合成方法
CN105849080A (zh) * 2013-12-20 2016-08-10 阿彻丹尼尔斯米德兰德公司 直接合成生物基烷基和呋喃二元醇醚、乙酸酯、醚-乙酸酯以及碳酸酯
CN103709039B (zh) * 2013-12-25 2015-04-22 南京龙源天然多酚合成厂 Cu-丝光沸石催化合成没食子酸甲(乙)酯的方法
CN105622377A (zh) * 2014-11-05 2016-06-01 上海爱普植物科技有限公司 藜芦醛的制备方法
CN108373403A (zh) * 2018-05-14 2018-08-07 上海华堇生物技术有限责任公司 一种邻苯二甲醚的新制备方法
CN109134207A (zh) * 2018-08-29 2019-01-04 阜新汉道化工有限责任公司 一种苯甲醚的催化合成方法
CN113185476B (zh) * 2021-04-29 2023-09-12 郑州大学 一种合成儿茶酚硫醚类化合物的方法

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Also Published As

Publication number Publication date
EP0000162A1 (de) 1979-01-10
IT1096588B (it) 1985-08-26
JPS5412331A (en) 1979-01-30
IT7824771A0 (it) 1978-06-20
US4192949A (en) 1980-03-11
DE2860227D1 (en) 1980-12-04
JPS6143334B2 (it) 1986-09-26

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