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WO2000068192A2 - Procede de preparation d'esters (di)alkylperoxy d'acides (di)carboxyliques - Google Patents

Procede de preparation d'esters (di)alkylperoxy d'acides (di)carboxyliques Download PDF

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Publication number
WO2000068192A2
WO2000068192A2 PCT/EP2000/004393 EP0004393W WO0068192A2 WO 2000068192 A2 WO2000068192 A2 WO 2000068192A2 EP 0004393 W EP0004393 W EP 0004393W WO 0068192 A2 WO0068192 A2 WO 0068192A2
Authority
WO
WIPO (PCT)
Prior art keywords
isomer
process according
tert
dimethyl
hydroperoxide
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.)
Ceased
Application number
PCT/EP2000/004393
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English (en)
Other versions
WO2000068192A3 (fr
Inventor
Manfred Bergfeld
Axel Carstens
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.)
Akzo Nobel NV
Original Assignee
Akzo Nobel NV
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 Akzo Nobel NV filed Critical Akzo Nobel NV
Priority to JP2000617173A priority Critical patent/JP2002544189A/ja
Priority to KR1020017014106A priority patent/KR20020003875A/ko
Publication of WO2000068192A2 publication Critical patent/WO2000068192A2/fr
Publication of WO2000068192A3 publication Critical patent/WO2000068192A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/38—Peroxy compounds the —O—O— group being bound between a >C=O group and a carbon atom, not further substituted by oxygen atoms, i.e. esters of peroxy acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C07C407/003—Separation; Purification; Stabilisation; Use of additives

Definitions

  • the present invention pertains to a process for the preparation of alkylperoxy esters of carboxylic acids and di(alkylperoxy esters) of dicarboxylic acids.
  • the present invention has for its object to provide a process for the preparation of peroxyesters which uses non-corrosive raw materials, does not yield halogenated side products, and despite the use of a base does not lead to the formation of salt waste.
  • a preferred embodiment of the invention pertains to a process to make (di)alkylperoxy (di)carboxylic acid esters of formulae (I) and (II),
  • alkylhydroperoxide of formula (V) [H-O-O] n -R 3 (V) wherein R 1 , R 2 , and R 3 represent hydrocarbon groups that are optionally substituted with a hydroxyl group, and wherein R 1 optionally contains an ester moiety, and n stands for 1 , 2 or 3.
  • R 1 — C-0-CH CH 2 + H-O-O-R 3 ⁇ R 1 — C-O-O-R 3 + CH 3 C(O)H (2)
  • R 3 is chosen such that R 3 OOH is one of the following alkyl (di)hydroperoxides.
  • R 3 is chosen such that R 3 OOH is one of the following alkyl (di)hydroperoxides.
  • R 3 can be chosen such that R 3 OOH is a hydroperoxide obtainable by the reaction of ketones with H 2 O 2 , as described in Organic Peroxides, Vol. 2, Chapter 1 Stamm Hydroperoxides," pp. 1-152 (1971), published by D. Swern, ISBN 0471839612. Furthermore, a mixture of any of the above mentioned hydroperoxides can be used according to this embodiment.
  • Alkylperoxycarboxylic acid esters of formula (I) that are preferably prepared in accordance with the process of the invention include: ⁇ -cumylperoxyneodecanoate, hydrogenated ⁇ -cumylperoxyneodecanoate, 2,4,4-trimethylpentyl-2-peroxyneodecanoate, tert-amylperoxyneodecanoate, tert-butylperoxyneodecanoate, 1 ,1-dimethyl-3-hydroxybutyl-1-peroxy- neodecanoate, ⁇ -cumyiperoxypivalate, hydrogenated ⁇ -cumylperoxypivalate, 2,4,4- trimethylpentyl-2-peroxypivalate, tert-amylperoxypivalate, tert-butylperoxy- pivalate, 1 ,1-dimethyl-3-hydroxybutyl-1-peroxypivalate, ⁇ -cumylperoxy-2-
  • Alkylperoxydicarboxylic acid esters of formula (II) preferably prepared with the process according to the invention are: di-tert-butylperoxy malonate, di-tert-butylperoxy succinate, di-tert-butylperoxy glutarate, di-tert-butylperoxy adipate, di-tert-butylperoxy azelate, di-tert- butylperoxy phthalate, di-tert-amylperoxy malonate, di-tert-amylperoxy succinate, di-tert-amylperoxy glutarate, di-tert-amylperoxy adipate, di-tert-amylperoxy azelate, di-tert- amylperoxy phthalate, di(1 , 1 -dimethyl-3-hydroxybutyl-1 -peroxy) malonate, di(1 , 1 -dimethyl-3- hydroxybutyl-1-peroxy) succinate,
  • a solvent may be advantageous.
  • solvents include water, an organic solvent, and mixtures of such solvents.
  • organic solvent conventional phlegmatizers can be used, such as isododecane, di-tert-butyl phthalate and the like. The use of these conventional phlegmatizers is preferred if the acetaldehyde that is formed can be easily separated from the resulting perester.
  • an (aliphatic) organic solvent with 5 to 8 C-atoms.
  • n-pentane or n-hexane are especially preferred.
  • a low-boiling solvent it may be preferred to use it in combination with a conventional phlegmatizer in order to prevent hazardous situations to occur.
  • the solvent (or part of the solvent) may be present in the reactor before it is charged with one or more of the reactants. However, (part of) the solvent may also be added together with one or both of the reactants.
  • the base suitable for use as a catalyst in the process of the invention preferably is an alkaline (earth) hydroxide or an alkaline (earth) oxide, with the use of calcium hydroxide or sodium hydroxide as alkaline (earth) hydroxide and of calcium oxide or sodium oxide as alkaline (earth) oxide being especially preferred.
  • Such base is used in a conventional way and can be added to the reactor (wholly or partially) prior to, or together with, the other reactants.
  • phase transfer catalyst including compounds like tetra- butyl ammonium chloride, tetra-butyl ammonium bromide, tetra-butyl ammonium hydrosulfate, benzyl tri-ethyl ammonium chloride, benzyl tri-methyl ammonium chloride, dimethyl amino pyridine, and methyl tri-capryl ammonium chloride, can be employed as the phase transfer catalyst optionally used in the process according to the invention.
  • methyl tri-capryl ammonium chloride which is known by the trade designation Aliquat 336, being preferred.
  • the molar ratio of the vinyl groups in the (di)carboxylic acid (di)vinyl ester to the hydroperoxide groups in the alkylhydroperoxide in the process according to the invention preferably is in the range of 0.7 : 1.0 to 1.2 : 1.0.
  • a ratio of 0.8 : 1.0 to 1.0 : 1.0 (mole/mole) is preferred to minimise the contamination of the resulting perester with the starting vinyl ester.
  • the reaction according to the invention preferably is carried out at a temperature in the range of -10 to + 60°C. However, for safety reasons, a lower maximum temperature may have to be used. Therefore a temperature in the range of 0 to + 20°C may be preferred.
  • the process according to the invention preferably is carried out at standard pressure.
  • a further preferred embodiment of the invention relates to a process being worked at a pressure below atmospheric, in which the formed acetaldehyde is removed from the reaction solution by distillation. Because such a process requires lower distillation temperatures, it is less hazardous.
  • a carrier gas can be used to facilitate the removal of the acetaldehyde.
  • the acetaldehyde that is formed is removed from the perester and used in further chemical processes.
  • the (di)alkylperoxy(di)carboxylic acid esters prepared according to the invention can be used as polymerisation initiators, as hardeners for resins, for the modification of polymers, e.g., for cross-linking polyethylene, for the decomposition of polymers, for improving the cetane number in fuels, and as synergist in fireproofing agents.
  • the alkylperoxycarboxylic acid esters can be used in preparatory organic syntheses such as for the epoxidation of olefins.
  • Example 1 The following examples serve to further elucidate the invention.
  • Example 1 The following examples serve to further elucidate the invention.

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  • 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

La présente invention concerne un procédé de préparation d'esters (di)alkylperoxy d'acides (di)carboxyliques consistant à mettre à réagir un ester (di)vinyle d'acide (di)carboxylique avec un alkylhydropéroxide. On utilise de préférence un catalyseur de base, et éventuellement un catalyseur par transfert de phase. On peut également utiliser un ou plusieurs solvants. De préférence, on sépare l'acétaldéhyde obtenu du perester par distillation, et on l'utilise dans d'autres procédés chimiques.
PCT/EP2000/004393 1999-05-05 2000-05-02 Procede de preparation d'esters (di)alkylperoxy d'acides (di)carboxyliques Ceased WO2000068192A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2000617173A JP2002544189A (ja) 1999-05-05 2000-05-02 （ジ）カルボン酸の（ジ）アルキルパーオキシエステルを調製する方法
KR1020017014106A KR20020003875A (ko) 1999-05-05 2000-05-02 (디)카르복시산의 (디)알킬퍼옥시 에스테르의 제조방법

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19920541 1999-05-05
DE19920541.8 1999-05-05

Publications (2)

Publication Number Publication Date
WO2000068192A2 true WO2000068192A2 (fr) 2000-11-16
WO2000068192A3 WO2000068192A3 (fr) 2001-02-01

Family

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Application Number Title Priority Date Filing Date
PCT/EP2000/004393 Ceased WO2000068192A2 (fr) 1999-05-05 2000-05-02 Procede de preparation d'esters (di)alkylperoxy d'acides (di)carboxyliques

Country Status (3)

Country Link
JP (1) JP2002544189A (fr)
KR (1) KR20020003875A (fr)
WO (1) WO2000068192A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115536565A (zh) * 2022-09-23 2022-12-30 山东阳谷华泰化工股份有限公司 一种过氧化苯甲酸叔丁酯的制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102752741B1 (ko) * 2019-11-01 2025-01-08 주식회사 엘지화학 에틸렌-비닐아세테이트 공중합체의 제조방법

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1518740B1 (de) * 1965-01-08 1972-06-29 Peroxid Chemie Gmbh Verfahren zur Herstellung von Percarbonsaeure-tert.-butylestern
US3595898A (en) * 1968-03-11 1971-07-27 Halcon International Inc Peresters by reaction of carboxylic acids with organic hydroperoxides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115536565A (zh) * 2022-09-23 2022-12-30 山东阳谷华泰化工股份有限公司 一种过氧化苯甲酸叔丁酯的制备方法
CN115536565B (zh) * 2022-09-23 2024-04-05 山东阳谷华泰化工股份有限公司 一种过氧化苯甲酸叔丁酯的制备方法

Also Published As

Publication number Publication date
KR20020003875A (ko) 2002-01-15
WO2000068192A3 (fr) 2001-02-01
JP2002544189A (ja) 2002-12-24

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