EP1636202A1 - Verfahren zur herstellung einer organischen verbindung, die wenigstens eine oxygenierte funktionelle gruppe enthält - Google Patents

Verfahren zur herstellung einer organischen verbindung, die wenigstens eine oxygenierte funktionelle gruppe enthält

Info

Publication number
EP1636202A1
EP1636202A1 EP04741703A EP04741703A EP1636202A1 EP 1636202 A1 EP1636202 A1 EP 1636202A1 EP 04741703 A EP04741703 A EP 04741703A EP 04741703 A EP04741703 A EP 04741703A EP 1636202 A1 EP1636202 A1 EP 1636202A1
Authority
EP
European Patent Office
Prior art keywords
process according
reaction
carried out
oxidizable
imidoaromatic
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.)
Withdrawn
Application number
EP04741703A
Other languages
English (en)
French (fr)
Inventor
Olivier Buyle
Véronique Mathieu
Karol Lorent
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.)
Solvay SA
Original Assignee
Solvay SA
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
Application filed by Solvay SA filed Critical Solvay SA
Publication of EP1636202A1 publication Critical patent/EP1636202A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides

Definitions

  • the present invention relates to a process for the manufacture of an organic compound comprising at least one oxygen-containing functional group.
  • Compounds containing at least one oxygen-containing functional group can be used, for example, as monomers, as constituents of cosmetic compositions or as surfactants.
  • the invention aims to remedy the problems mentioned above.
  • the invention therefore relates to a process for the manufacture of an organic compound comprising at least one oxygenated functional group, according to which an organic precursor comprising an oxidizable functionality is subjected to a reaction with an idoarornatic percarboxylic acid.
  • the imidoarornatic percarboxylic acid often corresponds to the formula
  • A represents an optionally substituted benzene or napthalenic ring
  • the group or groups R which may be identical or different, represent hydrogen, an optionally substituted alkyl group, COOH or COOOH and n is an integer from 1 to S .
  • all of the groups R are H.
  • n is preferably 4 or 5.
  • the reaction is generally carried out at a temperature of at least -100 ° C. Often this temperature is at least 0 ° C. Preferably, it is at least 20 ° C. In the process according to the invention, the reaction is generally carried out at a temperature of at most 150 ° C.
  • this temperature is at most 80 ° C. Preferably, it is at most 60 ° C.
  • the reaction is generally carried out at a pressure of at least 0.5 bar. Preferably, this pressure is greater than or equal to about 1 bar (atmospheric pressure). In the process according to the invention, the reaction is generally carried out at a pressure of at most 100 bar. Often this pressure is at most 25 bar. Preferably, it is at most 15 bar.
  • the reaction is generally carried out in a reaction medium having a content of imidoarornatic percarboxylic acid of at least 0.1% by weight relative to the total weight of the reaction medium. Often this content is at least 5%. Preferably, it is at least 7%. In the process according to the invention, this content is generally at most 90%. Often this content is at most 80%. Preferably, it is at most 70%.
  • the reaction is generally carried out in a reaction medium having an organic precursor content of at least 1% by weight relative to the total weight of the reaction medium. Often this content is at least 10%. Preferably, it is at least 30%. In the process according to the invention, this content is generally at most 80%. Often this content is at most 75%. Preferably it is at most 70%.
  • the process according to the invention can be carried out in the presence of an organic solvent, preferably a polar organic solvent such as for example dioxane or tetrahydrofuran.
  • the process according to the invention can also be carried out in the absence of solvent, the imidoarornatic percarboxylic acid being generally soluble in the organic precursor. This allows the reaction to be carried out with a lower volume of reaction medium and a high volume productivity.
  • a progressive addition of the imidoaromatic percarboxylic acid is carried out to the reaction medium.
  • a continuous addition of the imidoaromatic percarboxylic acid is carried out to the reaction medium.
  • the imidoaromatic percarboxylic acid can be introduced into the reaction, for example in the form of a solution in an organic solvent or in pure form.
  • the reaction is generally carried out for a period of at least 10 min. Often this duration is at least 30 min. Preferably, it is at least 1 hour.
  • the reaction is generally carried out for a period of at most 50 hours. Often, this duration is at most 20 hours. Preferably, it is at most 10 h. A duration of at most 5 hours is more particularly preferred. It has been found that imidoaromatic percarboxylic acid is capable of reacting quickly with the precursor.
  • the reaction is carried out in the substantial absence of water.
  • the reaction is generally carried out in a reaction medium having a water content of at most 10% by weight relative to the total weight of the reaction medium. Often this content is at most 5%. Preferably, it is at most 1%.
  • a reaction medium having a water content of greater than or equal to about 100 mg / kg gives good results.
  • the oxygenated compound can be separated from the reaction medium by techniques known per se, such as distillation or crystallization.
  • the imidoaromatic carboxylic acid by-product of the reaction can optionally be removed from the reaction medium, for example, by aqueous extraction.
  • the organic precursor is often chosen from cyclic or acyclic olefins substituted or not, cyclic or acyclic ketones substituted or not, compounds containing at least one oxidizable sulfur atom, compounds containing at least one oxidizable selenium atom, compounds containing at least one nitrogen atom oxidizable, compounds containing at least one oxidizable phosphorus atom and compounds containing at least one oxidizable iodine atom.
  • the organic precursor is an oxidizable fluorinated compound.
  • the organic precursor is an acyclic olefin
  • it generally comprises from 2 to 100, preferably from 2 to 20 carbon atoms. Often, it includes a double bond in position 1 or 2. Preferably, it comprises a double bond in position 1 (terminal).
  • acyclic olefins are ethylene, propylene, 1-butene, 2-butene and their substituted derivatives such as allyl chloride, allyl alcohol, vinyl choride, vinylidene chloride, vinyl fluoride, vinylidene fluoride and hexafluoropropylene.
  • the organic precursor when it is a cyclic olefin, it generally comprises from 3 to 100, preferably from 4 to 20 carbon atoms. Often, it comprises a cycle comprising from 4 to 8, preferably from 5, 6 or 7 atoms.
  • the cycle can be a carbocycle or a heterocycle.
  • Specific examples of cyclic olefins are cyclopropene, cyclobutene, cyclopentene, cyclohexene, norbornene, dicyclopentadiene, ⁇ -pinene, and their substituted derivatives.
  • the organic precursor when it is an acyclic ketone, it generally comprises from 3 to 100, preferably from 3 to 20 carbon atoms.
  • acyclic ketones are acetone, butanone, pentanone, hexanone and their substituted derivatives such as for example trifluoroacetone, hexafluoroacetone or 4,4'difluorobenzophenone.
  • the organic precursor when it is a cyclic ketone, it generally comprises from 4 to 100, preferably from 4 to 20 carbon atoms.
  • cyclic ketones are cyclobutanone, cyclopentanone, cyclohexanone, cycloheptanone and their substituted derivatives.
  • the organic precursor is chosen from compounds containing at least one oxidizable sulfur atom, it is often chosen from symmetrical or asymmetrical thioethers and mercaptatis, in particular alkyl or aryl thioethers and mercaptans, generally comprising 1 to 100, preferably from 1 to 20 carbon atoms.
  • specific examples are methyl, ethyl, propyl or n-butyl mercaptan, among dimethyl, diethyl, dipropyl or di n-butyl sulfide, among methyl ethyl or methyl sulfide.
  • the method according to the invention provides access to a variety of organic compounds containing sulfur, which can optionally also serve as an organic precursor, such as, for example, disulfides, sulfenic or sulfinic acids, and disulfoxides.
  • organic precursor such as, for example, disulfides, sulfenic or sulfinic acids, and disulfoxides.
  • the organic precursor is chosen from compounds containing at least one oxidizable nitrogen atom, it is often chosen from amines, in particular alkyl- or arylamines and imines, generally comprising from 1 to 100, preferably from 1 to 20 carbon atoms.
  • Primary, secondary or tertiary amines can be used.
  • the method according to the invention provides access to a variety of organic compounds containing nitrogen, which can optionally also serve as an organic precursor, such as, for example, hydroxylamines and oximes.
  • organic precursor such as, for example, hydroxylamines and oximes.
  • the organic precursor is chosen from compounds containing at least one oxidizable iodine atom, it is often chosen from aryl or heteroaryl iodides generally comprising from 5 to 100, preferably from 6 to 24 carbon atoms and their substituted derivatives.
  • aryl or heteroaryl iodides generally comprising from 5 to 100, preferably from 6 to 24 carbon atoms and their substituted derivatives.
  • a specific example is iodobenzene.
  • the organic precursor is chosen from compounds containing at least one oxidizable phosphorus atom, it is often chosen from phosphines, in particular alkyl- or arylphosphines, phosphine oxides and phosphonates, generally comprising from 3 to 100, from preferably from 3 to 20 carbon atoms and their substituted derivatives.
  • phosphines in particular alkyl- or arylphosphines, phosphine oxides and phosphonates, generally comprising from 3 to 100, from preferably from 3 to 20 carbon atoms and their substituted derivatives.
  • phosphines in particular alkyl- or arylphosphines, phosphine oxides and phosphonates, generally comprising from 3 to 100, from preferably from 3 to 20 carbon atoms and their substituted derivatives.
  • Specific examples are trialkylphosphines and triarylphosphines
  • Example 1 A solution of peracid was previously prepared by dissolving 277 g of PAP in 700 ml of dioxane contained in a one-liter volumetric flask.
  • Example 3 By following procedures analogous to Example 1 but replacing dioxane by tetiahydrofuran, glycidol was obtained from allyl alcohol. The glycidol was hydrolyzed to glycerin in the presence of sulfuric acid.
  • Example 3
  • the synthesis was carried out in a 25 cm 3 flask heated to 60 ° C by means of an oil bath and surmounted by a condenser cooled to -10 ° C by circulation of a water / ethylene glycol mixture. No agitation system was used.
  • the synthesis of dibutylsulfone by oxidation of dibutyl sulfide was carried out in the presence of PAP dissolved in dioxane (see Example 1).
  • the synthesis was carried out in a three-necked 100 cm flask maintained at 20 ° C. by immersion in a thermostatically controlled water bath.
  • the flask was surmounted by a condenser cooled to -10 ° C by circulation of a water / ethylene glycol mixture.
  • a CaCl 2 cartridge was located at the outlet of the condenser to avoid humidity entry.
  • the reaction medium was homogenized by magnetic stirring.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Pyrane Compounds (AREA)
EP04741703A 2003-06-03 2004-06-02 Verfahren zur herstellung einer organischen verbindung, die wenigstens eine oxygenierte funktionelle gruppe enthält Withdrawn EP1636202A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0306718A FR2855824A1 (fr) 2003-06-03 2003-06-03 Procede pour la fabrication d'un compose organique comprenant au moins un groupement fonctionnel oxygene
PCT/EP2004/050990 WO2004106313A1 (fr) 2003-06-03 2004-06-02 Procede pour la fabrication d'un compose organique comprenant au moins un groupement fonctionnel oxygene

Publications (1)

Publication Number Publication Date
EP1636202A1 true EP1636202A1 (de) 2006-03-22

Family

ID=33443125

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04741703A Withdrawn EP1636202A1 (de) 2003-06-03 2004-06-02 Verfahren zur herstellung einer organischen verbindung, die wenigstens eine oxygenierte funktionelle gruppe enthält

Country Status (6)

Country Link
US (1) US20070037990A1 (de)
EP (1) EP1636202A1 (de)
JP (1) JP2006526593A (de)
CN (1) CN1802365A (de)
FR (1) FR2855824A1 (de)
WO (1) WO2004106313A1 (de)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1233846B (it) * 1988-01-20 1992-04-21 Ausimont Spa Perossiacidi immido aromatici
DE3906768A1 (de) * 1989-03-03 1990-09-06 Henkel Kgaa Peroxycarbonsaeuren und deren verwendung
GB9626778D0 (en) * 1996-12-23 1997-02-12 Procter & Gamble Hair coloring compositions
GB2330358A (en) * 1997-10-15 1999-04-21 Contract Chemicals Limited Epoxidation of Alkenes
EP1034801A1 (de) * 1999-03-05 2000-09-13 The Procter & Gamble Company Ein Oxidationsmittel und ein Chelatbildungsmittel enthaltender Artikel mit einem Geruchskontrollsystem
CN1349562A (zh) * 1999-04-26 2002-05-15 宝洁公司 血液检测组合物

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
None *
See also references of WO2004106313A1 *

Also Published As

Publication number Publication date
WO2004106313A1 (fr) 2004-12-09
US20070037990A1 (en) 2007-02-15
JP2006526593A (ja) 2006-11-24
FR2855824A1 (fr) 2004-12-10
CN1802365A (zh) 2006-07-12

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