In situ monitoring of the crystalline state of active pharmaceutical ingredients during high-shear wet granulation using a low-frequency Raman probe

Nomura, Kazuya; Titapiwatanakun, Varin; Hisada, Hiroshi; Koide, Tatsuo; Fukami, Toshiro

doi:10.1016/j.ejpb.2019.12.004

Cited by 22 publications

(19 citation statements)

References 36 publications

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“…In a case study of 1:1 caffeine22 glutaric acid cocrystal, ball milling induced polymorphic transformation from the stable form II to the metastable form I [16]. In other studies of 1:1 theophyllineglutaric acid and 1:1 caffeine-glutaric acid cocrystals, low-frequency Raman spectra and powder X-ray diffraction were used to monitor the dissociation of cocrystals and conversion to theophylline or caffeine monohydrate [17]. The case of scalable spray-drying and hot-melt extrusion for a cocrystal formation approach sometimes resulted in a low cocrystal yield due to partial amorphization [15,18].…”

Section: Introductionmentioning

confidence: 99%

Complete Cocrystal Formation during Resonant Acoustic Wet Granulation: Effect of Granulation Liquids

et al. 2021

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The manufacturing of solid pharmaceutical dosage forms composed of cocrystals requires numerous processes during which there is risk of dissociation into parent molecules. Resonant acoustic wet granulation (RAG) was devised in an effort to complete theophylline–citric acid (THPCIT) cocrystal formation during the granulation process, thereby reducing the number of operations. In addition, the influence of granulation liquid was investigated. A mixture of anhydrous THP (drug), anhydrous CIT (coformer), and hydroxypropyl cellulose (granulating agent) was processed by RAG with water or ethanol as a granulation liquid. The purposes were to (i) form granules using RAG as a breakthrough method; (ii) accomplish the cocrystallization during the integrated unit operation; and (iii) characterize the final solid product (i.e., tablet). The RAG procedure achieved complete cocrystal formation (>99%) and adequately sized granules (d50: >250 μm). The granulation using water (GW) facilitated formation of cocrystal hydrate which were then transformed into anhydrous cocrystal after drying, while the granulation using ethanol (GE) resulted in the formation of anhydrous cocrystal before and after drying. The dissolution of the highly dense GW tablet, which was compressed from granules including fine powder due to the dehydration, was slower than that of the GE tablet.

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Section: Introductionmentioning

confidence: 99%

Complete Cocrystal Formation during Resonant Acoustic Wet Granulation: Effect of Granulation Liquids

et al. 2021

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“…The granulator's acrylic wall has no effect on the LF-Raman. 32,33) Polytetrafluoroethylene (PTFE) tape (5490; 3 M Japan Limited, Tokyo, Japan) was attached to the spray unit outlet to prevent powder leakage. The exposure time and integration time were measured at 3 s and 5 acc, respectively, and the measurement interval was set to 1 min.…”

Section: Experimental Materialsmentioning

confidence: 99%

“…They suggested that water adsorbed on the surface and mechanical loading due to grinding were the factors causing lattice disorder that triggered cocrystal dissociation. Duggirala et al 31) reported that when tablets containing caffeine-oxalic acid (OXA) cocrystals were stored under humidified conditions, the cocrystal dissociated due to water adsorption on the surface. For these reports, Nomura et al 32) succeeded in monitoring cocrystal dissociation in wet granulation, a unit operation, using LF-Raman.…”

Section: Introductionmentioning

confidence: 99%

“…Duggirala et al 31) reported that when tablets containing caffeine-oxalic acid (OXA) cocrystals were stored under humidified conditions, the cocrystal dissociated due to water adsorption on the surface. For these reports, Nomura et al 32) succeeded in monitoring cocrystal dissociation in wet granulation, a unit operation, using LF-Raman. 33) However, it is hard to say that the LF-Raman system Nomura et al 32) used could monitor cocrystal dissociation in real time because it took 5 min to obtain an LF-Raman spectrum.…”

Section: Introductionmentioning

confidence: 99%

“…For these reports, Nomura et al 32) succeeded in monitoring cocrystal dissociation in wet granulation, a unit operation, using LF-Raman. 33) However, it is hard to say that the LF-Raman system Nomura et al 32) used could monitor cocrystal dissociation in real time because it took 5 min to obtain an LF-Raman spectrum. Furthermore, no reports have evaluated the effect of coformers and disintegrants, which are used in solid dosages as typical additives, on the dissociation of cocrystals in the manufacturing process to select the optimized solid-state form.…”

Section: Introductionmentioning

confidence: 99%

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Monitoring of Cocrystal Dissociation during the Wet Granulation Process in the Presence of Disintegrants by Using Low-Frequency Raman Spectroscopy

Suzuki

Fukui

Otaka

et al. 2021

CHEMICAL & PHARMACEUTICAL BULLETIN

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The aim of this study was to evaluate the effect of three coformers and five disintegrants in the granulation formulation on the dissociation of cocrystal during the granulation process by monitoring wet granulation with probe-type low-frequency Raman (LF-Raman) spectroscopy. As model cocrystals, paracetamol (APAP)-oxalic acid (OXA), APAP-maleic acid (MLA), and APAP-trimethylglycine (TMG) were used. The monitoring of the granulation recipe containing cocrystals during wet granulation was performed over time with high-performance LF-Raman spectrometry and the dissociation rate was calculated from the results of multivariate analysis of LF-Raman spectra. The dissociation rate decreased in the order of APAP-TMG, APAP-OXA, and APAP-MLA, showing the same order as observed in Powder X-ray diffraction measurements. Furthermore, to compare the effect of disintegrants on the dissociation rate of APAP-OXA, LF-Raman monitoring was performed for the granulation recipes containing five typical disintegrants (two lowsubstitution hydroxypropyl cellulose (HPC), cornstarch (CSW), carmellose sodium (CMC), and crospovidone (CRP)). The dissociation rate of APAP-OXA decreased in the order of CSW, HPCs, CMC, and CRP. This difference in the dissociation rate of APAP-OXA was thought to be due to the disintegration mechanism of the disintegrants and the water absorption ratio, which was expected to affect the water behavior on the disintegrant surface during wet granulation. These results suggested that probe-type LF-Raman spectroscopy is useful to monitor the dissociation behavior of cocrystals during wet granulation and can compare the relative stability of cocrystal during wet granulation between different formulations.

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Simple Construction of Multistage Stable Silicon–Graphite Hybrid Granules for Lithium‐Ion Batteries

Zhang

Wang

Yuan

et al. 2023

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volume change (≈300%) during the lithiation process causes severe electrode pulverization. [7] On the contrary, graphite offers high initial Coulombic efficiency (ICE), good electrical conductivity, and structural stability. [8][9][10] The synergy of graphite and Si not only significantly improves the energy density, but ensures long battery life by effectively alleviating the lithiation-induced volumetric expansion of Si. [11] The main challenge of SGC is the large difference between Si and graphite in volume change, causing an electrical contact loss of graphite in composite easily. [12] More seriously, the intrinsic disparity between Si and graphite anodes (including the anodic potential peak range and lithium-ion diffusion kinetics) causes extremely continuous stress on graphite during the cycle process. [13][14][15] To solve this problem, commercial SGC anodes are typically prepared by a twosection process that first preparing a modified Si seed and then combining it with graphite. [4,16] Many researches focus on the preparation of modified silicon with promising results. [17][18][19] Xu et al. prepared a fullerene carbon layer coating on the surface of Si nanoparticles (Si NPs) by controlling the association of polyaromatic molecules, effectively alleviating the volume changes of Si. [20] Yang et al. created a polyaniline layer coating on Si NPs by aniline bridge and assisted self-assembly. [21] Modified Si NPs possessed competitive electrochemical performance with a reversible capacity over 1000 mAh g −1 after 300 cycles. Although these modified Si composites greatly improve electrochemical stability, the complex modification process severely limits their industrial production when cost effectiveness is taken into account. On the other hand, many combining methods, such as mechanical mixing, [22,23] high energy ball milling, [24][25][26] liquid solidification, [27,28] and spray drying, [29,30] are commonly used to produce commercial SGC electrodes. [3,4,31] However, the above methods cannot guarantee uniform dispersion of Si in the graphite matrix. The stress concentration caused by aggregated Si domains will lead to the generation and propagation of cracks in composite electrodes, eventually resulting in electrode failure. Therefore, it is critical to design a cost-effective route to improve the dispersion of Si and fabricate SGC with a stable structure.Because of its high specific capacity, the silicon-graphite composite (SGC) is regarded as a promising anode for new-generation lithium-ion batteries. However, the frequently employed two-section preparation process, including the modification of silicon seed and followed mixture with graphite, cannot ensure the uniform dispersion of silicon in the graphite matrix, resulting in a stress concentration of aggregated silicon domains and cracks in composite electrodes during cycling. Herein, inspired by powder engineering, the two independent sections are integrated to construct multistage stable silicon-graphite hybrid granules (SGHGs) through wet granulation...

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In situ monitoring of the crystalline state of active pharmaceutical ingredients during high-shear wet granulation using a low-frequency Raman probe

Cited by 22 publications

References 36 publications

Complete Cocrystal Formation during Resonant Acoustic Wet Granulation: Effect of Granulation Liquids

Complete Cocrystal Formation during Resonant Acoustic Wet Granulation: Effect of Granulation Liquids

Monitoring of Cocrystal Dissociation during the Wet Granulation Process in the Presence of Disintegrants by Using Low-Frequency Raman Spectroscopy

Simple Construction of Multistage Stable Silicon–Graphite Hybrid Granules for Lithium‐Ion Batteries

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