Anhydrides of the Normal Aliphatic Saturated Monobasic Acids

Wallace, James M.; Copenhaver, J. E.

doi:10.1021/ja01848a017

Cited by 26 publications

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“…10,12-Tricosadiynoic anhydride ( 1 ) was prepared by heating commercially available 10,12-tricosadiynoic acid with acetic anhydride; it has been reported previously but spectral characterization data are unavailable. It is a colorless microcrystalline powder (form 1A ) when precipitated from cold diethyl ether but is converted entirely into microcrystalline helical ribbons (form 1B , Figure ) when crystallized rapidly (∼5 min) in the cold (∼5 °C) from petroleum ether (bp 40−60 °C).…”

Section: Resultsmentioning

confidence: 99%

Macroscopic Helical and Cylindrical Morphologies from Achiral 1,3-Diynes

et al. 2000

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Diacetylenes containing an anhydride function (1) or two s-triazine groups (2) precipitate from organic solvents in large helical or cylindrical forms, respectively, which have been studied by optical and scanning electron microscopy. X-ray diffraction studies on helices of 10,12-tricosadynoic anhydride, {n-C10H21C⋮CC⋮C(CH2)8CO}2O (1), show a lamellar crystalline phase with layer spacing of 42.5 ± 0.5 Å and support a noninterdigitated bilayer structure. The crystal structure of a related amphiphilic diacetylene, n-C10H21C⋮CC⋮C(CH2)8CH2OSO2C6H4Me-4 (3), is also reported and discussed: triclinic, P1̄, a = 5.9730(10) Å, b = 8.0690(10) Å, c = 29.524(3) Å; α = 95.020(10)°, β = 93.260(10)°, γ = 97.480(10)°. The nonamphiphilic, α,ω-difunctionalized diacetylene, 6,6‘-(deca-4,6-diyne-1,10-diyl)di-2,4-diamino-1,3,5-triazine, 2-{4,6-(NH2)2C3N3}(CH2)3C⋮CC⋮C(CH2)3-{C3N3(NH2)2-4,6}-2 (2), forms solid cylindrical particles of mean length ∼0.5 mm, which may derive from helix formation. The origin of macroscopic chirality in the solid-state morphology of the achiral anhydride (1) is discussed.

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Section: Resultsmentioning

confidence: 99%

Macroscopic Helical and Cylindrical Morphologies from Achiral 1,3-Diynes

et al. 2000

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“…Nonanoic anhydride was synthesized from commercially available nonanoic acid and acetic anhydride following the procedure of Wallace & Copenhaver (1941). The acetic acid and excess acetic anhydride were removed through distillation, resulting in the anhydride as an oil (96% yield).…”

Section: Methodsmentioning

confidence: 99%

Nonanoic acid, other alkanoic acids, and related compounds as antifeedants in Hylobius abietis pine weevils

Månsson

Schlyter

Eriksson

et al. 2006

Entomologia Exp Applicata

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A medium‐length, straight‐chain alkanoic acid, nonanoic acid, is known from laboratory microassays to be an antifeedant in adults of the large pine weevil, Hylobius abietis (L.) (Coleoptera: Curculionidae). Our hypothesis was that we could find new, less volatile alkanoic acids or related compounds suitable for field application and with improved long‐term duration. Alkanoic acids of varying chain lengths (C6–C13) were tested for antifeedant activity in H. abietis adults. Microassay choice tests showed that straight‐chain (C6–C11) alkanoic acids were active. However, high activities were restricted to the (C6–C10) acids, with the C9 (nonanoic acid) at 4 µmol cm−2 being the most active one. In a no‐choice test on pine twigs, the antifeedant effect of C10 acid was lower than that of the C8 and C9 acids. In microassays, less volatile methyl‐branched alkanoic acids exhibited lower antifeedant activities than did the corresponding straight‐chain ones. However, the most active of the methyl‐branched acids, 2‐methyldecanoic acid, had an activity similar to that of nonanoic acid. Compounds related to nonanoic acid were either active (1‐nonanol), weakly active (nonanoic anhydride), or inactive (nonanal, sodium nonanoate). The anhydride was highly active in the microassay, but less active on twigs. The antifeedant effects of the straight chain (C8–C10) alkanoic acids against pine weevil feeding were tested in the field. In contrast to the results from the twig tests, the less volatile C10 acid was more active in the field for the protection of transplants on fresh clear cuts over a 3‐month period than both the C8 and C9 acids. Phytotoxic effects of the alkanoic acids were observed both in the field and in laboratory studies. If a protective layer of paraffin was applied to the stem prior to application of the alkanoic acids, these undesired side effects were reduced.

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“…These methods require solvents and expensive and/or hazardous reagents such as thionyl chloride. Instead, dehydration of the fatty acids (caprylic, capric, lauric, and palmitic) to their anhydrides was effected by heating in excess acetic anhydride followed by distillative decomposition of the intermediate acetic–fatty acid mixed anhydride (Albitzky, ; Wallace Jr. and Copenhaver, ). NMR spectra ( 1 H and 13 C) of the fatty acid anhydrides can be found in the Figs S12–S15.…”

Section: Resultsmentioning

confidence: 99%

Potential Vegetable‐Based Diesel Fuels from Perkin Condensation of Furfuraldehyde and Fatty Acid Anhydrides

Baldwin

Davis

Hughes

et al. 2019

J Americ Oil Chem Soc

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Domestically produced biofuels may help to reduce dependence on imported oil for powering transportation and infrastructure in the future. In this report, we reacted medium-chain and long-chain fatty anhydrides (capric, caprylic, lauric, and palmitic) with furfuraldehyde by the Perkin condensation to produce 2-n-alkenylfurans. In the second step, the 2-n-alkenylfurans were hydrogenated to form 2-n-alkyltetrahydrofurans. Basic fuel property testing (melting point, density, kinematic viscosity, derived cetane number, and calorific value) of the 2-nalkyltetrahydrofurans indicates they are potentially useful as fuels for diesel engines. The mixture composed of 2-octyl-and 2-decyltetrahydrofuran had the best combination of fuel properties including a low melting point (−39 C), high cetane number (63.1), high flash point (98.2 C), and low viscosity (2.26 mm 2 s −1 , 40 C), which compares favorably with specifications for diesel #2 and biodiesel.

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Anhydrides of the Normal Aliphatic Saturated Monobasic Acids

Abstract: Anhydrides of Normal Aliphatic Acids 699 in ultrachromatograms and in checking the purity of these compounds.4. An inexpensive and rapid method for viewing fluorescent materials in solution and chromatograms has been given. Adrian, Michigan

Cited by 26 publications

References 0 publications

Macroscopic Helical and Cylindrical Morphologies from Achiral 1,3-Diynes

Macroscopic Helical and Cylindrical Morphologies from Achiral 1,3-Diynes

Nonanoic acid, other alkanoic acids, and related compounds as antifeedants in Hylobius abietis pine weevils

Potential Vegetable‐Based Diesel Fuels from Perkin Condensation of Furfuraldehyde and Fatty Acid Anhydrides

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