EP1071651A1 - Procede de preparation de carbonates de dibenzyle - Google Patents

Procede de preparation de carbonates de dibenzyle

Info

Publication number
EP1071651A1
EP1071651A1 EP99919186A EP99919186A EP1071651A1 EP 1071651 A1 EP1071651 A1 EP 1071651A1 EP 99919186 A EP99919186 A EP 99919186A EP 99919186 A EP99919186 A EP 99919186A EP 1071651 A1 EP1071651 A1 EP 1071651A1
Authority
EP
European Patent Office
Prior art keywords
formula
catalyst
process according
carbonates
basic
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Withdrawn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
EP99919186A
Other languages
German (de)
English (en)
Inventor
Edwin Ritzer
Claus Dreisbach
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.)
Bayer Chemicals AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of EP1071651A1 publication Critical patent/EP1071651A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates

Definitions

  • Dibenzyl carbonates are required as precursors for benzyl carbazates.
  • benzyl carbazates are used as intermediates for the production of crop protection agents and pharmaceuticals. They are used in particular for peptide syntheses (see EP-A 106 282).
  • hydrazinosuccinate an inhibitor of aspartate aminotransferase, can be prepared from benzyl carbazate.
  • EP-A 143 078 describes the use of benzyl carbazate for the production of crop protection agents.
  • R 'in each case represents a C 1 -C 4 -alkyl radical
  • R and n have the meaning given for formula (I),
  • the two benzyl groups occurring in formula (I) are generally identical. If there are several radicals R in a benzyl group in the formulas (I) and (III), these can be the same or different.
  • R preferably represents C j -C 4 alkyl, phenyl, fluorine or
  • Chlorine and n preferably for zero, 1 or 2.
  • unsubstituted dibenzyl carbonate is particularly preferably prepared from a dialkyl carbonate of the formula (II) and unsubstituted benzyl alcohol.
  • R ' is preferably methyl or ethyl.
  • the most diverse basic reacting compounds are suitable as catalysts for the process according to the invention.
  • Solid base compounds are preferred as catalysts for reasons of easier separation after the process according to the invention has ended. Examples are: alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, alkali metal and alkaline earth metal carbonates and hydrogen carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate and alkali metal or earth alkali metal methanolate.
  • alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide
  • alkaline earth metal hydroxides such as calcium hydroxide
  • alkali metal and alkaline earth metal carbonates and hydrogen carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate and alkali metal or earth alkali metal methanolate.
  • Amino compounds with higher molecular weights of, for example, 100 to 200 can also be used as catalysts. Examples of these are bicyclic - 4 -
  • Amino compounds such as 1,5-diazabicyclo [4.3.0] non-5-ene and 1,8-diazabicyclo- [5.4.0] -undec-7-ene. It is also possible to use basic titanium compounds such as titanium (IV) isopropylate and basic tin compounds such as dibutyltin oxide and dimethyltin diodecanate.
  • Preferred catalysts are:
  • the catalyst can e.g. in amounts of 0.0001 to 20 mol%, based on the dialkyl carbonate used.
  • the particular dialkyl carbonate of the formula (II) with the particular benzyl alcohol of the formula (III) and the catalyst for example in a molar ratio of 1: (20 to 1.6) :( 0.1 to 0.0001), before - moves 1: (8 to 1.8) :( 0.01 to 0.0003) and particularly preferably 1: (5 to 2) :( 0.01 to
  • 0.001 can be implemented. If appropriate, one can in the presence of a solvent stable under the reaction conditions, e.g. work in the presence of aromatic hydrocarbons or cycloaliphatic hydrocarbons. It is preferred to work in the presence of toluene.
  • a solvent stable under the reaction conditions e.g. work in the presence of aromatic hydrocarbons or cycloaliphatic hydrocarbons. It is preferred to work in the presence of toluene.
  • the process according to the invention can be carried out, for example, at temperatures of 50 to 150 ° C., preferably at 60 to 160 ° C. and a pressure of, for example, 1 to 0.001 bar.
  • This process can optionally be promoted by adding an azeotrope, such as an aromatic hydrocarbon, especially toluene.
  • reaction mixture can, for example, be worked up by, if appropriate, any remaining light - 5 -
  • the starting compounds of the formulas (II) and (III) are initially introduced together with the catalyst and, if appropriate, a solvent or azeotrope, the mixture is warmed to the reaction temperature and alcohol R'OH already formed during the reaction is removed, e.g. by distillation, optionally under reduced pressure and / or optionally together with an azeotrope. Residual alcohol R'OH and any solvent or azeotroping agent still present can be removed after the reaction has ended, for example at 100 to 160 ° C and decreasing pressures, e.g. up to 0.001 bar. Then, but of course also immediately after the reaction has ended, the catalyst can be removed; if it is a solid catalyst e.g. by filtration or decantation, otherwise e.g. by extraction with water.
  • the dibenzyl carbonate of the formula (I) i.a. in purities of over 90%, often over 95%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne des carbonates de dibenzyle, obtenus par réaction d'un carbonate de dibenzyle avec un alcool de benzyle en présence d'un catalyseur basique et par séparation hors du mélange réactionnel, des constituants faiblement volatiles et du catalyseur. Ce procédé permet de préparer des carbonates de benzyle de manière simple, dans de bons rendements et sans impliquer de complexité particulière en termes de technologie de sécurité.
EP99919186A 1998-04-14 1999-04-01 Procede de preparation de carbonates de dibenzyle Withdrawn EP1071651A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19816497 1998-04-14
DE19816497A DE19816497A1 (de) 1998-04-14 1998-04-14 Verfahren zur Herstellung von Dibenzylcarbonaten
PCT/EP1999/002287 WO1999052853A1 (fr) 1998-04-14 1999-04-01 Procede de preparation de carbonates de dibenzyle

Publications (1)

Publication Number Publication Date
EP1071651A1 true EP1071651A1 (fr) 2001-01-31

Family

ID=7864480

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99919186A Withdrawn EP1071651A1 (fr) 1998-04-14 1999-04-01 Procede de preparation de carbonates de dibenzyle

Country Status (6)

Country Link
US (1) US6350893B1 (fr)
EP (1) EP1071651A1 (fr)
JP (1) JP2002511443A (fr)
AU (1) AU3705199A (fr)
DE (1) DE19816497A1 (fr)
WO (1) WO1999052853A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19859290A1 (de) * 1998-12-22 2000-06-29 Bayer Ag Verfahren zur Herstellung von Diarylcarbonaten
US6420588B1 (en) * 2001-07-24 2002-07-16 General Electric Company Interfacial method of preparing ester-substituted diaryl carbonates

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5967254A (ja) 1982-10-08 1984-04-16 Shionogi & Co Ltd セルレイン中間体の製造法
US4734119A (en) 1983-11-15 1988-03-29 Ciba-Geigy Corporation Novel phosphorus compounds for protecting cultivated plants from the phytotoxic action of herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9952853A1 *

Also Published As

Publication number Publication date
DE19816497A1 (de) 1999-10-21
JP2002511443A (ja) 2002-04-16
WO1999052853A1 (fr) 1999-10-21
AU3705199A (en) 1999-11-01
US6350893B1 (en) 2002-02-26

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