Oxydation von Oelsäure durch Permanganat bei Gegenwart geringer Mengen Alkali

Holde, D.; Marcusson, J.

doi:10.1002/cber.19030360303

Cited by 15 publications

(2 citation statements)

References 7 publications

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“…However, to the best of our knowledge, lipidic compounds bearing -hydroxyketone moiety have never been used as polyols for the preparation of polyurethanes. These compounds were previously produced by oxidation of oleic acid with neutral KMnO 4 [30], ring-opening with DMSO as oxidant of epoxidized fatty acids in presence of BF 3 Et 2 O [31] or by oxidation of the diol obtained after hydroxylation of the lipidic acid [32]. These routes are of great interest to access the fatty α-hydroxyketone derivatives even if stoichiometric (toxic) reagents were usually implied.…”

Section: Introductionmentioning

confidence: 99%

Polyurethane Thermosets Using Lipidic Poly(α‐Hydroxyketone)

Briou

Caillol

et al. 2019

J Americ Oil Chem Soc

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Lipidic polyols based on -hydroxyketone reactive groups were investigated for polyurethane thermosets. The reactivity of this peculiar secondary alcohol group in triglyceride structure was compared, without use of catalyst, to that of poly(1,2-diol)triglyceride and castor oil to demonstrate the influence of ketone in  position of alcohol group in presence of HDMI for urethanisation rate. The kinetic effect of ketone group was also studied on various lipidic architectures: mono(-hydroxyketone) ester, di(-hydroxyketone) diester and tri(hydroxyketone) triglyceride. The presence of hydrogen bonds in the network coming from urethane, residual alcohol and ketone in hard segments of PU was discussed and correlated to the thermal stability and the soft mechanical properties of the resulting polyurethane thermosets.

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Section: Introductionmentioning

confidence: 99%

Polyurethane Thermosets Using Lipidic Poly(α‐Hydroxyketone)

Briou

Caillol

et al. 2019

J Americ Oil Chem Soc

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“…The oxidative cleavage of ozonides, epoxides, and 1,2-diols has been intensively studied, − notably for the preparation of aldehydes, acids, and esters. However, only very little attention has been devoted to fatty α-hydroxyketones − and 1,2-diketones, − even though these compounds are usually proposed as reaction intermediates.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Cleavage of Fatty 1,2-Diketones to Esters

Chavallard

Miguel

et al. 2019

ACS Sustainable Chem. Eng.

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The cleavage of a fatty 1,2-diketone derived from methyl oleate into the corresponding esters, i.e., methyl nonanoate and dimethyl azelate was studied by organocatalysis using oxygen as a clean oxidant. Only carbene generated from thiazolium salts and K 2 CO 3 could efficiently catalyze this transformation. It was found that, under the optimized conditions, the oxidative cleavage leads to the formation of a 1:1 mixture of esters and potassium carboxylates.An acidic treatment of the mixture, followed by esterification with methanol, led to the desired 2 esters with 75 and 77% yield. This protocol was extended to a range of symmetrical and unsymmetrical fatty 1,2-diketones and the corresponding esters were isolated with 61-84% yield.

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Zur Frage des Trocknens fetter Öle

Eibner¹

1926

Angewandte Chemie

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Oxydation von Oelsäure durch Permanganat bei Gegenwart geringer Mengen Alkali

Cited by 15 publications

References 7 publications

Polyurethane Thermosets Using Lipidic Poly(α‐Hydroxyketone)

Polyurethane Thermosets Using Lipidic Poly(α‐Hydroxyketone)

Organocatalytic Cleavage of Fatty 1,2-Diketones to Esters

Zur Frage des Trocknens fetter Öle

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