Can green nitrocellulose-based propellants be made through the replacement of diphenylamine by the natural product curcumin?

Rodrigues, Rodrigo Leonard Barboza; Buitrago, Pedro Augusto Gomes; Nakano, Nami Lavigne; Peixoto, Fernando Cunha; Lemos, Maurício Ferrapontoff; França, Tanos C. C.; Filho, Letivan G. Mendonça

doi:10.1080/07370652.2020.1859646

Cited by 16 publications

(17 citation statements)

References 33 publications

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“…Dejeaifve and co-workers (2020), in adition to their previous works, analyzed potential (natural) substances, such as alpha-tocopherol, alphaionone and curcumin for replacing DPA, using Heat Flow Microcalorimetry (HFC) to predict their shelf life when compared to AK-II. In previous works of our research group, we also found promising results for NCbased propellants stabilized with 1.0% of curcumin (Rodrigues et al, 2019(Rodrigues et al, , 2021, while very recent research on the use of alpha-ionone as stabilizer (Damseaux et al, 2021), has demonstrated its effectiveness, with the main derivative products identi ed as: 3-oxo-α-ionone, 4-oxo-β-ionone and 4,5epoxy-α-ionone.…”

Section: Introductionmentioning

confidence: 53%

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On the replacement of traditional stabilizers by guaiacol in environmentally safe nitrocellulose-based propellants

Rodrigues

Silva²,

Rosato

et al. 2022

Clean Techn Environ Policy

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In this work we investigated the possibility of substituting diphenylamine (DPA) by the natural product guaiacol, as a stabilizer for nitrocellulose (NC)-based propellants. Stability evaluation, using heat-ux calorimetry (HFC), revealed lower heat ows associated with our guaiacol-stabilized propellant samples when compared to those of propellants stabilized with the traditional stabilizers. Also, pressure-vacuum stability tests (PVST) showed that our propellant exhibited lower evolved gas volumes. Traditional tests, such as the German Test, and the Bergmann-Junk Test, scored a NO volume, after titration, of 0.87 ml (below the limit-value for acceptance, which is 2.0 ml), and the Storage Test, showed that our samples are stable and do not degrade for more than 3 days when submitted to a constant temperature of 100°C. The homogeneity, stability and compatibility of our samples were evaluated through scanning electron microscopy (SEM), differential scanning calorimetry (DSC), and isothermal thermogravimetry (TG).Ballistic parameters were estimated using a closed vessel along with ad hoc codes, for comparison purposes. Finally, a high-performance liquid chromatography (HPLC) method developed before allowed inferring the stabilizer consumption after arti cial ageing of samples. Such method also showed that the material met the correspondent stability criteria (AOP-48). In short, our results clearly indicate that guaiacol is an effective and e cient substitute for DPA as a propellant stabilizer for single base nitrocellulose-based propellants, making them more environmentally friendly.

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Section: Introductionmentioning

confidence: 53%

“…The procedure of HPLC-UV used for the determination of DPA and guaiacol in propellants was successfully established before (Rodrigues, 2021) and within this work showed again to be pertinent, fast, simple and speci c for DPA and guaiacol analysis, which standard peaks can be found in Figures 8 and 9.…”

Section: Stabilizer Concentration Depletionmentioning

confidence: 62%

On the replacement of traditional stabilizers by guaiacol in environmentally safe nitrocellulose-based propellants

Rodrigues

Silva²,

Rosato

et al. 2022

Clean Techn Environ Policy

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“…For many years, new less harmful stabilisers have been studied. REACh (Registration, Evaluation and Authorisation of Chemicals) regulation requires that old phthalate deterrents be replaced by "greener" molecules [16][17][18][19]. It is important to continue this work and to make propellant powder as "green" as possible.…”

Section: Introductionmentioning

confidence: 99%

Identification of the Degradation Products from α‐Tocopherol Used as Stabiliser in “Green” Propellants through its Lifetime

Damseaux

Scholl

Damblon

et al. 2022

Propellants Explo Pyrotec

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Stabilisers are added to gun and rocket propellants to react with species responsible for nitrate ester degradation during storage. The degradation products can be toxic and therefore harmful. There is a need to replace such stabilisers by "green" molecules and to study their degradation patterns through ageing. Propellant powders must remain chemically stable for a minimum of ten years when stored at temperatures equivalent to 25 °C [1]. α-Tocopherol is a natural product that has been known for decades in other fields (Vitamin E) such as the pharmaceutical, food and cosmetics industries. It can act as a 'green' stabiliser" for smokeless powders because its heat flow is stable over time. In this paper, we characterise its stabilisation mechanism by identifying its main degradation products that could form within the propellant in an oxidising environment and in the presence of nitric acid. Liquid chromatog-raphy (LC) and gas chromatography (GC) separations are performed in order to dissociate the compounds formed during ageing. Compounds are then analysed by APCI-timsTOF to obtain the molecular ion masses and then perform fragmentation spectra (MS/MS) to characterise their structure. In addition, using preparative HPLC-UV, the degradation products are collected and analysed by NMR, with the aim of identifying the molecules. These identification methods help to unravel the stabilisation mechanism under accelerated ageing conditions. A time-related fluctuation of the degradation products amounts is also observed, which indicates that the decomposition products also have a stabilisation effect. The three major α-tocopherol degradation products are identified as: 2,3-epoxy-α-tocopherylquinone, 5,6-epoxy-α-tocopherylquinone and α-tocored.

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“…It is therefore necessary to study and develop new generations of stabilisers that have the main properties of being slowly consumed and that are even not toxic. This last criterion is essential in the light of the current REACh regu-lation, which requires that old stabilisers be replaced by "greener" products [14,[26][27][28]. Dejeaifve et al demonstrate that stabiliser such as 2,3,5-trimethylphenol, 1,2,3-trimethoxybenzene, α-ionone, curcumin and α-tocopherol are able to stabiliser nitrate esters [2,26,29].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Identification of the Degradation Products from α‐Ionone Used as Stabiliser in “Green” Propellants through its Lifetime

Damseaux

Scholl

Damblon

et al. 2021

Propellants Explo Pyrotec

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A stabiliser is added to gun and rocket propellants to react with species responsible for degradation during decomposition. Propellant powder manufacturers and army personnel are confronted with toxicity during powder degradation and must replace current stabilisers with nontoxic molecules. According to the STANAG 4582 (North Atlantic Treaty Organization (NATO) Standardisation Agreement [1]), propellant powders must remain chemically stable for a minimum of ten years when stored at temperatures equivalent to an isothermal storage (25 °C). Single and double base smokeless powders with α-ionone as a "green" stabiliser are tested and the results show that the heat flow is stable over time and that the autocatalysis occurs 2 to 3 times later than in powders with conventional stabilisers. This stabiliser is efficient for all nitrate esterbased propellants. In the present paper, we identify and monitor the evolution of the main degradation products over time by nuclear magnetic resonance (NMR), mass spectrometry (MS) to unravel the stabilisation mechanism under accelerated aging conditions. A time-related fluctuation of their respective amounts (increasing then decreasing, then re-increasing, …) is observed, which indicates that the daughter products have also a stabilisation effect. The three major α-ionone daughter products are identified as: 3-oxo-α-ionone, 4-oxo-β-ionone and 4,5-epoxy-α-ionone.

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Can green nitrocellulose-based propellants be made through the replacement of diphenylamine by the natural product curcumin?

Cited by 16 publications

References 33 publications

On the replacement of traditional stabilizers by guaiacol in environmentally safe nitrocellulose-based propellants

On the replacement of traditional stabilizers by guaiacol in environmentally safe nitrocellulose-based propellants

Identification of the Degradation Products from α‐Tocopherol Used as Stabiliser in “Green” Propellants through its Lifetime

Identification of the Degradation Products from α‐Ionone Used as Stabiliser in “Green” Propellants through its Lifetime

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