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Acids

Q: What are the different types of acids and their characteristics?

Acids can be classified into two main categories: organic acids and inorganic acids. Organic acids, such as acetic acid (found in vinegar) and citric acid (found in citrus fruits), are carbon-based and are typically weaker in strength. Inorganic acids, such as sulfuric acid and hydrochloric acid, are not carbon-based and tend to be stronger in strength. Acids can also be classified by their ionization strength, with strong acids (e.g., hydrochloric acid) completely dissociating in water, while weak acids (e.g., acetic acid) only partially dissociate. Understanding these acid characteristics is important when selecting the appropriate acid for your research needs.

Q: What are some common applications of acids in research and industry?

Acids have a wide range of applications in research and industry. In chemistry and biochemistry, acids are used in various analytical techniques, such as titrations, to determine the concentration of substances. They are also used in the synthesis of organic compounds and the purification of materials. In the pharmaceutical industry, acids are used in the production of certain drugs and in the formulation of medications. In the food industry, acids like citric acid are used as preservatives and flavorings. In the mining and metallurgy industries, acids are used for etching, cleaning, and extracting metals from ores. Understandign the diverse applications of acids is crucial for optimizing your research and industrial processes.

Q: How can PubCompare.ai help researchers when working with acids?

PubCompare.ai can be a valuable tool for researchers working with acids. The platform allows you to efficiently screen the protocol literature and leverage AI to pinpoint critical insights. By using PubCompare.ai, you can identify the most effective protocols related to acids for your specific research goals. The platform's AI-driven analysis can highlight key differences in protocol effectiveness, enabling you to choose the best option for reproducibility and accuracy. This can save you time and effort, and help you optimize your research workflow when working with acids.

Acids are a class of chemical compounds characterized by their ability to donate hydrogen ions (H+) or accept electron pairs in chemical reactions.
They are widely found in nature and play crucial roles in various biological and chemical processes.
Acids can be organic (e.g., acetic acid, citric acid) or inorganic (e.g., sulfuric acid, hydrochloric acid), and they can be classified based on their strength, structure, or source.
The study of acids is fundamental to the fields of chemistry, biochemistry, and physiology, as they are involved in numerous essential functions, such as pH regulation, metabolism, and catalysis.
Researchers can utilize PubCompare.ai to efficiently locate and analyze the best protocols for working with acids from the literature, preprints, and patents, optimizing their research workflow and enhancing reproducibility in acids analysis through AI-driven protocol comparisons.

Most cited protocols related to «Acids»

Metabolite Derivatization for GC-MS Analysis

All metabolite reference standards underwent a two-step derivatization procedure. Therefore 1 mg of each standard was dissolved in a solution of 1 ml methanol:water:isopropanol (2.5:1:1 v/v). Then 10 μl of each standard solution were taken out and evaporated to dryness. First, methoximation was performed to inhibit the ring formation of reducing sugars, protecting also all other aldehydes and ketones. A solution of 40 mg/ml O-methylhydroxylamine hydrochloride, (CAS: [593-56-6]; Formula CH5NO.HCl; Sigma-Aldrich No. 226904 (98%)) in pyridine (99.99%) was prepared. The dried standards and 10 μl of the O-methylhydroxylamine reagent solution were mixed for 30 s in a vortex mixer and subsequently shaken for 90 minutes at 30°C. Afterwards, 90μl of N-methyl-N-trimethylsilyltrifluoroacetamide (MSTFA) with 1% trimethylchlorosilane (TMCS) (1 ml bottles, Pierce, Rockford IL) was added and shaken at 37°C for 30 min for trimethylsilylation of acidic protons to increase volatility of metabolites. A mixture of internal retention index (RI) markers was prepared using fatty acid methyl esters (FAME markers) of C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28 and C30 linear chain length, dissolved in chloroform at a concentration of 0.8 mg/ml (C8-C16) and 0.4 mg/ml (C18-C30). 2 μl of this RI mixture were added to the reagent solutions, transferred to 2 mL glass crimp amber autosampler vials. Data acquisition parameters are given in table 1. Subsequent to data processing using the instrument manufacturer’s software programs, spectra and retention indices were manually curated into the new Leco FiehnLib (359-008-100) or automatically transferred by Agilent to the new Agilent FiehnLib (G1676AA).

Kind T., Wohlgemuth G., Lee D.Y., Lu Y., Palazoglu M., Shahbaz S, & Fiehn O. (2009). FiehnLib – mass spectral and retention index libraries for metabolomics based on quadrupole and time-of-flight gas chromatography/mass spectrometry. Analytical chemistry, 81(24), 10038-10048.

Publication 2009

Acids Aldehydes Amber Cardiac Arrest Chloroform Esters Fatty Acids Isopropyl Alcohol Ketones Methanol methoxyamine Protons pyridine Retention (Psychology) Sugars trimethylchlorosilane Volatility

Quantitative Proteomics of HeLa-E. coli Mixture

An Escherichia coli K12 strain was grown in standard LB medium, harvested, washed in PBS, and lysed in BugBuster (Novagen Merck Chemicals, Schwalbach, Germany) according to the manufacturer's protocol. HeLa S3 cells were grown in standard RPMI 1640 medium supplemented with glutamine, antibiotics, and 10% FBS. After being washed with PBS, cells were lysed in cold modified RIPA buffer (50 mm Tris-HCl, pH 7.5, 1 mm EDTA, 150 mm NaCl, 1% N-octylglycoside, 0.1% sodium deoxycholate, complete protease inhibitor mixture (Roche)) and incubated for 15 min on ice. Lysates were cleared by centrifugation, and after precipitation with chloroform/methanol, proteins were resuspended in 6 m urea, 2 m thiourea, 10 mm HEPES, pH 8.0. Prior to in-solution digestion, 60-μg protein samples from HeLa S3 lysates were spiked with either 10 μg or 30 μg of E. coli K12 lysates based on protein amount (Bradford assay). Both batches were reduced with dithiothreitol and alkylated with iodoacetamide. Proteins were digested with LysC (Wako Chemicals, GmbH, Neuss, Germany) for 4 h and then trypsin digested overnight (Promega, GmbH, Mannheim, Germany). Digestion was stopped by the addition of 2% trifluroacetic acid. Peptides were separated by isoelectric focusing into 24 fractions on a 3100 OFFGEL Fractionator (Agilent, GmbH, Böblingen, Germany) as described in Ref. 45 (link). Each fraction was purified with C₁₈ StageTips (46 (link)) and analyzed via liquid chromatography combined with electrospray tandem mass spectrometry on an LTQ Orbitrap (Thermo Fisher) with lock mass calibration (47 (link)). All raw files were searched against the human and E. coli complete proteome sequences obtained from UniProt (version from January 2013) and a set of commonly observed contaminants. MS/MS spectra were filtered to contain at most eight peaks per 100 mass unit intervals. The initial MS mass tolerance was 20 ppm, and MS/MS fragment ions could deviate by up to 0.5 Da (48 (link)). For quantification, intensities can be determined alternatively as the full peak volume or as the intensity maximum over the retention time profile, and the latter method was used here as the default. Intensities of different isotopic peaks in an isotope pattern are always summed up for further analysis. MaxQuant offers a choice of the degree of uniqueness required in order for peptides to be included for quantification: “all peptides,” “only unique peptides,” and “unique plus razor peptides” (42 (link)). Here we chose the latter, because it is a good compromise between the two competing interests of using only peptides that undoubtedly belong to a protein and using as many peptide signals as possible. The distribution of peptide ions over fractions and samples is shown in supplemental Fig. S1.

Cox J., Hein M.Y., Luber C.A., Paron I., Nagaraj N, & Mann M. (2014). Accurate Proteome-wide Label-free Quantification by Delayed Normalization and Maximal Peptide Ratio Extraction, Termed MaxLFQ. Molecular & Cellular Proteomics : MCP, 13(9), 2513-2526.

Publication 2014

Acids Antibiotics, Antitubercular Biological Assay Buffers Cells Centrifugation Chloroform Cold Temperature Deoxycholic Acid, Monosodium Salt Digestion Dithiothreitol Edetic Acid Escherichia coli Escherichia coli K12 Glutamine HeLa Cells HEPES Homo sapiens Immune Tolerance Iodoacetamide Ions Isotopes Liquid Chromatography Methanol Peptides Promega Protease Inhibitors Proteins Proteome Radioimmunoprecipitation Assay Retention (Psychology) Sodium Chloride Staphylococcal Protein A Tandem Mass Spectrometry Thiourea Tromethamine Trypsin Urea

Molecular Dynamics Simulations of Peptides

Simulations of Ala₅ were run using the simulation package Gromacs^{28 ,29} using a protocol similar to that used in our previous work,^{15 (link)} and with the implementation of the Amber force fields by Sorin and Pande.^{30 (link)} The peptide was unblocked and protonated at both N and C termini, corresponding to the experimental conditions of pH 2.^{14 (link)} Molecular dynamics simulations of each peptide in a 30 Å cubic simulation box of explicit TIP3P water³¹ were run at a constant temperature of 300 K and a constant pressure of 1 atm, with long range electrostatic terms evaluated using particle-mesh Ewald (PME) using a 1.0 Å grid spacing and a 9 Å cutoff for short-range interactions. For each force field, four runs of 50 ns each were initiated from different starting configurations. Further details of the simulation protocols are as published.^{15 (link)}Replica exchange molecular dynamics (REMD) simulations of the blocked peptide Ac-(AAQAA)₃-NH₂ were run using Gromacs^{28 ,29} with 32 replicas spanning a temperature range of 278 K to 595 K. The peptide was solvated in a truncated octahedron simulation cell of 1022 TIP3P water molecules with an initial distance of 35 Å between the nearest faces of the cell. This cell was equilibrated for 200 ps at 300 K and a constant pressure of 1 atm. Subsequently, all REMD simulations were done at constant volume, with long range electrostatics calculated using PME with a 1.2 Å grid spacing and 9 Å cutoff. Dynamics was propagated with a Langevin integration algorithm using a friction of 1 ps⁻¹, and replica exchange attempts every 1 ps (every 500 steps with a time step of 2 fs). Typical acceptance probabilities for the replica exchange were in the range 0.1–0.5. All replica exchange runs used the same set of initial configurations, which were taken from the final configurations of a preliminary replica exchange simulation with ff99SB. The simulations were run for at least 30 ns per replica, of which the first 10 ns were discarded in the analysis (with an aggregate of ≈ 1 µs for each force field). To test for possible system size dependence, additional simulations of Ac-(AAQAA)₃-NH₂ in a 45 Å truncated octahedron box solvated by 2268 water molecules were run for 30 ns using a similar protocol, in this case with 32 replicas at 5 K intervals between 278 and 433 K.
Additional simulations were performed for the unblocked peptide HEWL19, derived from hen egg-white lysozyme with sequence KVFGRC(SMe)ELAAAMKRHGLDN. The structure and parameters for the S-methylated Cys 6 were adapted from those for methionine and are given in Supporting Information (SI) Figure 1 and Table 1 respectively. Both termini as well as all acidic side chains were protonated, corresponding to the experimental conditions of pH 2.^{14 (link)} The peptide was solvated in a truncated octahedron simulation cell with a 42 Å distance between nearest faces, and equilibrated at constant pressure for 200 ps at 300 K. Constant volume REMD was run with 32 replicas spanning the temperature range 278 K to 472 K, for 27 ns, of which the first 10 ns were discarded in the analysis. All other parameters were the same as for Ac-(AAQAA)₃-NH₂.
Native state simulations of ubiquitin were run starting from the crystal structure 1UBQ.^{32 (link)} The protein was solvated by 2586 explicit TIP3P water molecules in a cubic simulation box of 45 Å length with long range electrostatics calculated using PME with a 1.2 Å grid spacing and 9 Å cutoff. To neutralize the system charge, 7 sodium and 8 chloride ions were added. Dynamics was propagated for 30 ns at constant pressure (1 atm) and temperature (300 K) using a Nosé-Hoover thermostat³³ and Parrinello-Rahman barostat.³⁴

Best R.B, & Hummer G. (2009). Optimized molecular dynamics force fields applied to the helix-coil transition of polypeptides. The journal of physical chemistry. B, 113(26), 9004-9015.

Publication 2009

Acids Amber Cells Chlorides Cuboid Bone Electrostatics Face Friction hen egg lysozyme Ions Methionine Molecular Dynamics Peptides Pressure Proteins Sodium Ubiquitin

Quantitative Proteomics of Yeast Metabolism

We showcased our method using a TMT10-plex of yeast (S. cerevisiae wild-type strain BY4716) grown in synthetic complete media supplemented with 2% glucose (n=5) or 2% pyruvate (n=5) as the carbon source. We harvested the cells at OD_600nm=0.8. Cells were lysed by bead-beating in 8 M urea 200mM EPPS (4-(2-Hydroxyethyl)-1-piperazinepropanesulfonic acid), pH 8.5 and with protease and phosphatase inhibitors. Protein concentration was determined with the BCA assay. The BCA assay was performed according to manufacturer’s instructions with samples that were diluted at least 1:20, to ensure that the 8M urea has been diluted far below its compatibility limit. Samples were reduced with 5mM TCEP, alkylated with 10 mM iodoacetamide that was quenched with 10 mM DTT. A total of 100 μg of protein were chloroform-methanol precipitated. Protein was reconstituted in 200 mM EPPS pH 8.5 and digested by Lys-C overnight and trypsin for 6 h, both at a 1:100 protease-to-peptide ratio. Directly to the digest, we added a final volume of 30% acetonitrile and labelled 100 μg of peptide with 200 μg of TMT. To check mixing ratios, 2 μg of each sample were pooled, desalted, and analyzed by mass spectrometry. Using normalization factors calculated from this “label check,” samples were mixed 1:1 across all channels and desalted using a 100 mg Sep-Pak solid phase extraction column. The Pierce High-Select Fe-NTA Phosphopeptide Enrichment Kit was used to enrich phosphopeptides from the pooled TMT-labeled mixture. The unbound fraction and washes from this enrichment were combined and fractionated with basic pH reversed-phase (BPRP) HPLC, collected in a 96-well plate and combined down to 12 fractions prior to desalting and subsequent LC-MS/MS processing (14 (link), 15 ).

Navarrete-Perea J., Yu Q., Gygi S.P, & Paulo J.A. (2018). SL-TMT: A Streamlined Protocol for Quantitative (Phospho)proteome Profiling using TMT-SPS-MS3. Journal of proteome research, 17(6), 2226-2236.

Publication 2018

acetonitrile Acids Biological Assay Carbon Cells Chloroform ferric nitrilotriacetate Glucose High-Performance Liquid Chromatographies inhibitors Iodoacetamide Mass Spectrometry Methanol Peptide Hydrolases Peptides Phosphopeptides Phosphoric Monoester Hydrolases Proteins Pyruvate Saccharomyces cerevisiae Solid Phase Extraction Staphylococcal Protein A Strains Tandem Mass Spectrometry tris(2-carboxyethyl)phosphine Trypsin Urea Yeast, Dried

Oxylipin Quantification Protocol

Two different types of compounds (Table S-6) were used as internal standards. Type I internal standards were added to samples before extraction to mimic the extraction of prostaglandins, diols, epoxides and other oxylipins. The type I internal standards include 6-keto-PGF_1α-d4_, PGE₂-d4, 10,11 DHHep, 20 HETE-d6, 9 (S) HODE-d4, 5 HETE-d8, 11,12 EET-d8 and non-endogenous odd chain length monounsaturated fatty acids, 10,11 dihydroxynondecanoic acid 10,11-DHN. Type II internal standard was added at the last step before analysis to account for changes in volume and instrument variability. A synthetic acid, 1-cyclohexyl-dodecanoic acid urea (CUDA), was selected as type II internal standard.
The analytes were linked to their corresponding Type I internal standards for the purpose of quantification.

Yang J., Schmelzer K., Georgi K, & Hammock B.D. (2009). Quantitative Profiling Method for Oxylipin Metabolome by Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometry. Analytical Chemistry, 81(19), 8085-8093.

Publication 2009

5-hydroxy-6,8,11,14-eicosatetraenoic acid 6-Ketoprostaglandin F1 alpha 20-hydroxy-5,8,11,14-eicosatetraenoic acid Acids Dinoprostone Epoxy Compounds Fatty Acids, Monounsaturated lauric acid Oxylipins Prostaglandins Urea

Most recents protocols related to «Acids»

Chitosan Nanofiber Membranes for Tissue Regeneration

Not available on PMC !

Example 12

There has been a growing interest in the fabrication of nanofibers derived from natural polymers due to their ability to mimic the structure and function of extracellular matrix. Electrospinning is a simple technique to obtain nano-micro fibers with customized fiber topology and composition (FIGS. 33A and 33B). The chitosan electrospun nanofibers have recently been extensively studied due to the favorable properties of chitosan such as controllable biodegradation, good biocompatibility and high mechanical strength. Currently, chitosan can be electrospun from a solution of chitosan dissolved in either trifluoroacetic acid (TFA) or acetic acid (HAc). However, processes to remove residual acid and acid salts from the electrospun material generally resulted in a swelling of fibers and deterioration of the nano-fibrous structure. Crosslinking in combination with neutralization methods also had not been effective at preventing loss of nano-fibrous structure.

The current study aimed to improve and maintain nano-fibrous and porous structure of the electrospun membranes by introducing a new post electrospinning chemical treatment. Membrane thickness was tripled in this research in order to increase the general tearing strength. Scanning electron micrograph (SEM) examination (FIG. 33C) and transmission electron micrograph (TEM) examination (FIG. 33D) showed Fiber diameters of the triethanolamine/N-tert-butoxycarbonyl (TEA/t-BoC) treated membranes ranged from 40 nm to 130 nm while fiber diameters were not able to be determined for the Na₂CO₃group. Membranes treated by TEA/tboc (FIG. 34A) exhibited more nano-scale fibrous structure than membranes treated by saturated Na₂CO₃(FIGS. 35B-35D, as seen demonstrated in scanning electron micrographs. After immersion in PBS for 24 hours, membranes treated by TEA/tboc exhibited less than 30% swelling (FIG. 34B) and retained their nanofibrous structure, compared with membranes treated by Na₂CO₃(FIGS. 35B-35D) or compared with the non-treated chitosan membrane (FIG. 35A). After soaking the TEA/tBoc treated membranes in water overnight, membranes still kept the porous structure. In both, the before and after water status, fibers kept diameters in the nanometer range (FIG. 35C). TEA/tBoC modified nanofiber membranes also well preserved their fibrous structure over 4 weeks in physiological solution compared with Na₂CO₃treated membranes (FIG. 35D).

Chitosan membranes treated by TEA/tboc showed better nano-fiber morphology characteristics than membranes neutralized by saturated Na₂CO₃solution before and after being soaked in PBS. Retention of the nanofibrous structure for guided tissue regeneration applications may be of benefit for enabling nutrient exchange between soft gingival tissue and bone compartments and for mimicking the natural nanofibrillar components of the extracellular matrix during regeneration.

US11878088B2. Chitosan nanofiber compositions, compositions comprising modified chitosan, and methods of use (2024-01-23). The University of Memphis Research Foundation [US]. Inventors: Joel D. Bumgardner [US], Hengjie Su [US], Tomoko Fujiwara [US], Daniel G. Abebe [US], Kwei-Yu Liu [US].

Full text: Click here

Patent 2024

Acetic Acid Acids Bones Chitosan Electrons Environmental Biodegradation Extracellular Matrix Fibrosis Gingiva Guided Tissue Regeneration Hydrochloric acid Nutrients physiology Polymers Regeneration Retention (Psychology) Submersion TERT protein, human Tissue, Membrane Tissues Transmission, Communicable Disease triethanolamine Trifluoroacetic Acid Vision

Optimizing Secondary Battery Pouch Film Production

Not available on PMC !

Example 1

A secondary battery pouch film is produced, after the drying process temperature of the two-component type solvent-based emulsion having a start temperature of 175° C. to 190° C. is set to 100° C.

A secondary battery pouch film is produced, after the process temperature of the two-component type solvent-based emulsion having a start temperature lowered to 135° C. to 150° C. is set to 100° C.

Example 2

A secondary battery pouch film is produced, after the drying process temperature of the two-component type solvent-based emulsion having a start temperature of 175° C. to 190° C. is set to 120° C.

Example 3

A secondary battery pouch film is produced, after the drying process temperature of the two-component type solvent-based emulsion having a start temperature of 175° C. to 190° C. is set to 135° C.

Example 4

A secondary battery pouch film is produced, after the drying process temperature of the two-component type solvent-based emulsion having a start temperature of 175° C. to 190° C. is set to 150° C.

Example 5

A secondary battery pouch film is produced, after the drying process temperature of the two-component type solvent-based emulsion having a start temperature of 175° C. to 190° C. is set to 165° C.

Example 6

A secondary battery pouch film is produced, after the drying process temperature of the two-component type solvent-based emulsion having a start temperature of 175° C. to 190° C. is set to 180° C.

Example 7

A secondary battery pouch film is produced, after the drying process temperature of the two-component type solvent-based emulsion having a start temperature of 175° C. to 190° C. is set to 200° C.

Example 8

Example 9

Example 10

TABLE 1

Start Drying process

No.temperature (° C.)temperature (° C.)

Comparative Example 1175~190100

Comparative Example 2120

Comparative Example 3135

Comparative Example 4150

Comparative Example 5165

Comparative Example 6180

Comparative Example 7200

Example 1135~150100

Example 2120

Example 3135

Example 4150

Comparative Example 8165

Comparative Example 9180

Comparative Example 10200

Evaluation of Properties

Evaluation of Initial Peel Strength

- (1) An experimental sample is prepared by cutting the secondary battery pouch film to have a size of 1.5 cm by 15 cm in width and length, respectively.
- (2) The metal layer and the sealant layer are peeled off, and the peel strength is measured.

Evaluation of Hydrofluoric Acid Resistance

- (1) After the secondary battery pouch film is cut to have a size of 10 cm by 20 cm, two surfaces on both sides thermally adhered to each other.
- (2) A manufacturing solution (electrolyte+water (10,000 ppm (about 1%) of concentration of water in the solution)) is put inside the secondary battery pouch having the two surfaces adhering to each other, thermal adhering is performed, and a pack is manufactured.
- (3) The pack is stored at a high-temperature condition (85° C.) for 24 hours.
- (4) The electrolyte inside the pack is removed, and the sample is prepared (width 1.5 cm and length 15 cm) in the same manner as in the evaluation of initial peel strength.
- (5) The peel strength between the metal layer and the sealant layer is measured.

Evaluation of Electrolyte Resistance

- (1) An experimental sample is prepared by cutting the secondary battery pouch film to have a size of 1.5 cm by 15 cm in width and length, respectively.
- (2) The prepared sample is impregnated with a standard electrolyte (1.0 M LiPF6(EC/DEC/EMC: 1/1/1)) and is stored at a high temperature condition (85° C.) for 24 hours.
- (3) After the electrolyte is washed off, the metal layer and the sealant layer are peeled off, and the peel strength is measured.

Evaluation of Formability

- (1) A sample is prepared by cutting the produced secondary battery pouch film to have a size of 15 cm by 15 cm.
- (2) The prepared samples are formed by using a test die (size of 3 cm×4 cm) manufactured by Youlchon Chemical, Co., Ltd.
- (3) Evaluation of formability is repeatedly performed by changing the setting of the forming depth and is performed until ten or more samples are not broken.
- (4) A forming depth, in ten or more samples are not broken, is measured.

Evaluation of Penetration Strength

- (1) A sample having a width of 35 mm and a length of 600 mm is produced from the secondary battery pouch film.
- (2) The penetration strength is measured at intervals of about 40 mm in a direction from the outer layer toward the inner layer.
- (3) After the strength is measured ten times, an average value thereof is recorded.

In this case, the higher the formability, a forming process range may be wider during manufacturing of a battery. It is appropriate that the electrolyte resistance strength is equal to or higher than 90% of the initial peel strength, and the hydrofluoric acid resistance strength should be equal to or higher than 5 N/15 mm. Since the electrolyte resistance strength and the hydrofluoric acid resistance strength are much affected by the initial peel strength, it is appropriate that the initial peel strength is equal to or higher than 14 N/15 mm.

Table 2 shows evaluation of physical properties based on the curing start temperature and the drying process temperature.

TABLE 2

Hydrofluoric

DryingInitialElectrolyteacid

StartprocesspeelresistanceresistancePenetration

temperaturetemperaturestrengthstrengthstrengthstrengthFormability

No.(° C.)(° C.)(N/15 mm)(N/15 mm)(N/15 mm)(N)(mm)

Comparative1751002PeelingPeeling18.46.5

Example 1~190

Comparative1202.3PeelingPeeling19.26.6

Example 2

Comparative1352.2PeelingPeeling19.36.6

Example 3

Comparative1506.4PeelingPeeling19.36.5

Example 4

Comparative16514.514.15.824.26.3

Example 5

Comparative18014.814.35.724.66.1

Example 6

Comparative20015.614.85.824.56.1

Example 7

Example 11351009.2 8.13.919.46.8

Example 2~15012012.411.64.320.26.7

Example 313514.614.26.221.86.7

Example 415015.014.36.422.36.8

Comparative16515.114.86.423.86.3

Example 8

Comparative18015.715.16.224.26.1

Example 9

Comparative20016.115.46.524.76.0

Example 10

As known from the above, when an emulsion having a start temperature of 175° C. to 190° C. (Comparative Examples 1, 2, 3, and 4) is applied, the initial peel strength is relatively very low to be 10 N or lower when the drying process temperature is 150° C. or lower. The low initial peel strength resulted in a phenomenon where the sealant layer and the metal layer are completely separated from each other during evaluation of the electrolyte resistance strength and the hydrofluoric acid resistance strength.

When the drying process temperature is 165° C. to 200° C. (Comparative Examples 5, 6, and 7), the initial peel strength, the electrolyte resistance strength, and the hydrofluoric acid resistance strength are all good. However, the penetration strength increased to 24 N or higher. As well, a result that the formability does not reach 6.5 mm is obtained.

When the emulsion having a start temperature lowered to 135° C. to 150° C. is applied, the initial peel strength is 10 N/15 mm or lower only when the drying process temperature is 100° C. (Example 1), and the initial peel strength is 12 N/15 mm or higher in a drying process condition of 120° C. or higher (Examples and Comparative Examples 8 to 10). It is confirmed that a decrease in start temperature improves the adhesiveness even at a low drying process temperature.

However, the hydrofluoric acid resistance strength does not reach 5 N/15 mm in the 120° C. condition (Example 2), and the initial peel strength, the electrolyte resistance strength, and the hydrofluoric acid resistance strength are all good in conditions of 135° C. or higher (Examples 3 and 4 and Comparative Examples 8 to 10).

Similar to Comparative Examples 1 to 7, results of an increase in penetration strength in a condition of 165° C. to 200° C. (Comparative Examples 8, 9, 10) and the result of formability smaller than 6.5 mm is obtained.

The penetration strength increased to 20 N or higher at a condition of 135° C. to 150° C. (Examples 3 and 4), but has the best of the formability of 6.5 mm or more.

Therefore, only in a drying process temperature condition corresponding to the start temperature, all the properties of the initial peel strength, the electrolyte resistance strength, the hydrofluoric acid resistance strength are appropriate. When the drying process temperature is above 150° C., and particularly 165° C. or higher as found in an experiment, the penetration strength of the secondary battery pouch film significantly increases, and thus the formability decreases.

Therefore, in order to appropriately obtain all the physical properties, it is preferable to lower the drying process temperature to 150° C. or below, and to this end, it is preferable to lower the start temperature of the solvent-based emulsion to 150° C. or below.

According to the exemplary embodiments of the invention, when the secondary battery pouch film is manufactured, the primer layer composition that is interposed between the metal layer and the melt-extrusion resin layer or the sealant layer is made of a two-component curing-type organic solvent-based emulsion composition containing acid-modified polypropylene and a curing agent, wherein the curing start temperature and the drying process temperature are adjusted, and thermal lamination is not performed. Thereby, good formability, as well as good initial peel strength, hydrofluoric acid resistance, electrolyte resistance, etc. may be achieved.

The present invention was made under Project ID 20007148 from the Ministry of Trade, Industry and Energy, Korea Evaluation Institute of Industrial Technology under research project “Development of Technology of Materials and Components—Materials and Components Packaging Type”, research title “Performance Evaluation of Medium and Large Size Secondary Battery Pouch and Empirical Research for Application to Demand Companies” granted to Youl Chon Chemical Co., Ltd. For the period 2019 Sep. 1-2021 Feb. 28.

While the present invention has been described with respect to the specific embodiments, it will be apparent to those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention as defined in the following claims.

US11876235B2. Primer layer composition, secondary battery pouch film using the same, and method of manufacturing the same (2024-01-16). Youlchon Chemical Co., Ltd. [KR]. Inventors: Nok Jung Song [KR], Han Chul Park [KR], Hee Sik Han [KR], Ji Min Lee [KR].

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Patent 2024

Acids Adhesiveness Cold Temperature Electrolytes Emulsions Fever Hydrofluoric acid Metals Oligonucleotide Primers Physical Processes Polypropylenes Resins, Plant Solvents Technology Assessment

Enhancing Chalcopyrite Leaching with Thiourea

Not available on PMC !

Example 1

The effect of Tu on the electrochemical behavior of a chalcopyrite electrode was studied in a conventional 3-electrode glass-jacketed cell. A CuFeS₂electrode was using as working electrode, a saturated calomel electrode (SCE) was used as reference, and a graphite bar was used as counter-electrode. The CuFeS₂electrode was polished using 600 and 1200 grit carbide paper. All experiments were conducted at 25° C. using a controlled temperature water bath. The electrolyte composition was 500 mM H₂SO₄, 20 mM Fe₂SO₄and 0-100 mM Tu. Before starting any measurement, solutions were bubbled with N₂for 30 minutes to reduce the concentration of dissolved 02. Open circuit potential (OCP) was recorded until changes of no more than 0.1 mV/min were observed. After a steady OCP value was observed, electrochemical impedance spectroscopy (EIS) was conducted at OCP using a 5 mV a.c. sinusoidal perturbation from 10 kHz to 10 mHz. Linear polarization resistance (LPR) tests were also conducted using a scan rate of 0.05 mV/s at ±15 mV from OCP.

Linear potential scans were conducted at electrode potentials ±15 mV from the OCP measured at each Tu concentration. All scans showed a linear behavior within the electrode potential range analyzed. An increase in the slope of the experimental plots was observed with increasing Tu concentration. The slope of these curves was used to estimate the value of the polarization resistance (Ret) at each concentration. These values were then used to estimate the values of the dissolution current density using equation 1:

$\begin{matrix} i_{dissol} \approx \frac{RT}{{nFR}_{ct}} & Eq . (1) \end{matrix}$

FIG. 3 shows the effect of Tu on the dissolution current density and mixed potential of the CuFeS₂electrode, and indicates that a maximum dissolution current density was achieved when Tu concentration is 30 mM. Increasing Tu concentration to 100 mM resulted in a decrease in the current density and mixed potential of the CuFeS₂electrode. Moreover, after immersing the CuFeS₂electrode in the 100 mM Tu solution, a copper-like film was observed on the surface of the electrode, which film could only be removed by polishing the electrode with carbide paper.

FIG. 4 is a bar graph showing the effect of initial Tu or FDS concentration on the electrochemical dissolution of a chalcopyrite electrode in sulfuric acid solution at pH 2 and 25° C. A concentration of 10 mM Tu in the leach solution resulted in a six fold increase in dissolution rate compared to no Tu, and a concentration of 5 mM FDS resulted in a six fold increase relative to 10 mM Tu. A concentration of 10 mM Tu in leach solution also containing 40 mM Fe(III) resulted in a thirty fold increase in dissolution rate compared to 40 mM Fe(III) alone.

A column leach of different acid-cured copper ores was conducted with Tu added to the leach solution. A schematic description of the column setup is shown in FIG. 5. The column diameter was 8.84 cm, the column height was 21.6 cm, and the column stack height was 15.9 cm. The irrigation rate was 0.77 mL/min or 8 L/m²/h. The pregnant leach solution emitted from these columns was sampled for copper every 2 or 3 days using Atomic Absorption Spectroscopy (AAS).

The specific mineralogical composition of these ores are provided in Table 1. The Cu contents of Ore A, Ore B, and Ore C were 0.52%, 1.03%, and 1.22% w/w, respectively. Prior to leaching, ore was “acid cured” to neutralize the acid-consuming material present in the ore.

That is, the ore was mixed with a concentrated sulfuric acid solution composed of 80% concentrated sulfuric acid and 20% de-ionized water and allowed to sit for 72 hours. For one treatment using Ore C, Tu was added to the sulfuric acid curing solutions.

The initial composition of the leaching solutions included 2.2 g/L Fe (i.e. 40 mM, provided as ferric sulfate) and pH 2 for the control experiment, with or without 0.76 g/L Tu (i.e. 10 mM). The initial load of mineral in each column was 1.6 to 1.8 kg of ore. The superficial velocity of solution through the ore column was 7.4 L m⁻²h⁻¹. The pH was adjusted using diluted sulfuric acid. These two columns were maintained in an open-loop or open cycle configuration (i.e. no solution recycle) for the entire leaching period.

The results of leaching tests on the Ore A, Ore B and Ore C are shown in FIGS. 6, 7, and 8, respectively. The presence of Tu in the lixiviant clearly has a positive effect on the leaching of copper from the chalcopyrite. On average, the leaching rate in the presence of Tu was increased by a factor of 1.5 to 2.4 compared to the control tests in which the leach solutions did not contain Tu. As of the last time points depicted in FIGS. 6 to 8, copper extractions for columns containing Ore A, Ore B, and Ore C leached with a solution containing sulfuric acid and ferric sulfate alone, without added Tu, were 21.2% (after 198 days), 12.4% (after 50 days), and 40.6% (after 322 days), respectively. With 10 mM of added Tu, these extractions were 37.9%, 32.0%, and 72.3%, respectively.

Referring to FIG. 8, 2 mM Tu was added to the leach solution originally containing no Tu from day 322 onward, after which the leach rate increased sharply. From day 332 to day 448, the copper leached from this column increased from 40% to 58%, and rapid leaching was maintained throughout that period.

The averages for the last 7 days reported in FIG. 9 indicate that the leaching rate for acid-cured Ore C leached in the presence of 10 mM Tu is 3.3 times higher than for acid-cured Ore C leached in the absence of Tu, and 4.0 times higher than acid-cured and Tu-cured Ore C leached in the absence of Tu.

FIG. 10 shows the effect of Tu on solution potential. All potentials are reported against a Ag/AgCl (saturated) reference electrode. The solution potential of the leach solutions containing Tu was generally between 75 and 100 mV lower than the solution potential of leach solution that did not include Tu. Lower solution potentials are consistent with Tu working to prevent the passivation of chalcopyrite.

“Bottle roll” leaching experiments in the presence of various concentrations of Tu were conducted for coarse Ore A and Ore B. The tests were conducted using coarsely crushed (100% passing ½ inch) ore.

Prior to leaching, the ore was cured using a procedure similar to what was performed on the ore used in the column leaching experiments. The ore was mixed with a concentrated sulfuric acid solution composed of 80% concentrated sulfuric acid and 20% de-ionized water and allowed to settle for 72 hours to neutralize the acid-consuming material present in the ore. For several experiments, different concentrations of Tu were added to the ore using the sulfuric acid curing solutions.

The bottles used for the experiments were 20 cm long and 12.5 cm in diameter. Each bottle was loaded with 180 g of cured ore and 420 g of leaching solution, filling up to around one third of the bottle's volume.

The leaching solution from each bottle was sampled at 2, 4, 6 and 8 hours, and then every 24 hours thereafter. Samples were analyzed using atomic absorption spectroscopy (AAS) for their copper content.

The conditions for the bottle roll experiments are listed in Table 2. Experiments #1 to #6 were conducted using only the original addition of Tu into the bottles. For experiments #7 to #11, Tu was added every 24 hours to re-establish the Tu concentration.

A positive effect of Tu on copper leaching was observed. For the coarse ore experiments, a plateau was not observed until after 80 to 120 hours. Tu was added periodically to the coarse ore experiments, yielding positive results on copper dissolution.

The effect of different concentrations of Tu in the leach solution on the leaching of coarse ore (experiments #1 to #11 as described in Table 2) is shown in FIGS. 11 and 10.

For ore B, Tu was periodically added every 24 hours to re-establish the thioruea concentration in the system and thus better emulate the conditions in the column leach experiments. As may be observed from FIG. 9, 8 mM and 10 mM Tu yielded higher copper dissolution results than the other Tu concentrations tested for ore A. A plateau in dissolution is not observed until after approximately 120 hours, which varied with Tu concentration as shown in FIG. 11.

TABLE 1

MineralIdeal FormulaOre AOre BOre C

ActinoliteCa₂(Mg,Fe²⁺)₅Si₈O₂₂(OH)₂—1.8—

BiotiteK(Mg,Fe²⁺)₃AlSi₃O₁₀(OH)₂—4.2—

CalciteCaCO₃—19.3 —

ChalcopyriteCuFeS₂ 1.43.52.6

Clinochlore(Mg,Fe²⁺)₅Al(Si₃Al)O₁₀(OH)₈—15.0 —

DiopsideCaMgSi₂O₆—3.5—

GalenaPbS——0.1

GypsumCaSO₄2H₂O—1.2—

Hematiteα-Fe₂O₃—0.2—

K-feldsparKAlSi₃O₈17.910.8 —

KaoliniteAl₂Si₂O₅(OH)₄ 2.3—2.3

MagnetiteFe₃O₄—0.8—

MolybdeniteMoS₂<0.1——

MuscoviteKAl₂AlSi₃O₁₀(OH)₂21.96.041.6

PlagioclaseNaAlSi₃O₈—CaAlSi₂O₈13.625.4 —

PyriteFeS₂ 2.3—8.0

QuartzSiO₂40.08.344.4

RutileTiO₂ 0.5—0.9

SideriteFe²⁺CO₃—0.1—

Total100 100 100

As may be observed from FIG. 12, 5 mM Tu yielded higher copper dissolution results than the other Tu concentrations tested for ore B. As with ore A, a plateau in dissolution is not observed until after approximately 80 to 120 hours, which varied with Tu concentration as shown in FIG. 12. Periodic addition of Tu resulted in increased copper dissolutions and produced a delay in the dissolution plateau.

Interestingly, solutions containing 100 mM Tu did not appear to be much more effective on copper extraction than those containing no Tu, and even worse at some time points. This is consistent with the results of Deschenes and Ghali, which reported that solutions containing 200 mM Tu (i.e. 15 g/L) did not improve copper extraction from chalcopyrite. Tu is less stable at high concentrations and decomposes. Accordingly, it is possible that, when initial Tu concentrations are somewhat higher than 30 mM, sufficient elemental sulfur may be produced by decomposition of Tu to form a film on the chalcopyrite mineral and thereby assist in its passivation. It is also possible that, at high Tu dosages, some copper precipitates from solution (e.g. see FIG. 17) to account for some of the low extraction results.

US11859263B2. Process for leaching metal sulfides with reagents having thiocarbonyl functional groups (2024-01-02). Jetti Resources, LLC [US]. Inventors: David Dixon [CA], Edouard Asselin [CA], Zihe Ren [CA], Nelson Mora Huertas [US].

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Patent 2024

Acids actinolite Bath biotite Calcite calomel Carbonate, Calcium Cells chalcopyrite Chemoradiotherapy Copper Dielectric Spectroscopy diopside Electrolytes factor A feldspar ferric sulfate ferrous disulfide galena Graphite Gypsum hematite Kaolinite Magnetite Minerals muscovite Oxide, Ferrosoferric plagioclase Quartz Radionuclide Imaging Recycling rutile siderite Sinusoidal Beds Spectrophotometry, Atomic Absorption Suby's G solution Sulfur sulfuric acid TU-100

Synthesis of Triazolopyrimidine Derivatives

Not available on PMC !

Example 2

[Figure (not displayed)]

N-(2-chloro-4-(trifluoromethyl)phenyl)-2-(5-ethyl-2-morpholino-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide (Intermediate B) (200 mg, 352 μmol) was suspended in DMF (5 mL). Perfluorophenyl 3-hydroxypicolinate (Intermediate CT) (215 mg, 703 μmol) and Et₃N (97.0 μL, 703 μmol) were added and the RM was stirred at 70° C. for 3 hours. The RM was concentrated under reduced pressure. The crude product was first purified by column chromatography (Silica gel column: Silica 12 g, eluent DCM:MeOH 100:0 to 90:10). Then a second purification by reverse phase preparative HPLC (RP-HPLC acidic 9: 40 to 50% B in 2 min, 50 to 55% B in 10 min) afforded the title compound.

LC-MS: Rt=0.98 min; MS m/z [M+H]⁺ 690.6/692.6, m/z [M−H]⁻ 688.4/690.3; UPLC-MS 1

LC-MS: Rt=4.84 min; MS m/z [M+H]⁺ 690.2/692.2 m/z [M−H]⁻ 688.3/690.3; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.37 (s, br, 1H), 10.34 (s, br, 1H), 8.05 (m, 2H), 7.96 (d, J=2.1 Hz, 1H), 7.72 (dd, J=2.1 Hz, 8.7 Hz, 1H), 7.28 (m, 2H), 5.21 (s, 2H), 4.53 (m, 1H), 3.66 (m, 4H), 3.46 (m, 3H), 3.38 (m, 4H), 3.20 (m, 1H), 2.92 (m, 3H), 2.76 (m, 1H), 2.58 (m, 1H), 1.16 (t, J=7.5 Hz, 3H)

Example 24

[Figure (not displayed)]

To the stirred solution of N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)-2-(5-ethyl-2-(4-methoxycyclohex-1-en-1-yl)-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide (Intermediate Y) (300 mg, 504 μmol), 4-chloro-3-hydroxypicolinic acid (140 mg, 807 μmol), HOBt (136 mg, 1.01 mmol) and EDC.HCl (193 mg, 1.01 mmol) in DCM (20 mL) was added pyridine (122 μL, 1.51 mmol) at 0° C. The RM was stirred at RT for 16 hours. The RM was quenched with NaHCO₃and extracted with DCM. The organic layer was dried over Na₂SO₄and concentrated under reduced pressure. The crude product was purified by column chromatography (Silica gel column: Silica 4 g, eluent DCM:MeOH 100:0 to 98:2). The residue was purified by preparative chiral HPLC (instrument: Agilent 1200 series, with single quad mass spectrometer; column: LUX CELLULOSE-4, 250 mm×21.1 mm, 5.0 μm; eluent: A=hexane, B=0.1% HCOOH in EtOH; flow rate: 15 mL/min; detection: 210 nm; injection volume: 0.9 mL; gradient: isocratic: 50(A):50(B)).

Example 24a: The product containing fractions were concentrated at 40° C. and washed with n-pentane (5×10 mL), decanted and dried to give the title compound as an off-white solid—first eluting stereoisomer.

Chiral HPLC (C-HPLC 2): Rt=10.764 min

LC-MS: Rt=1.08 min; MS m/z [M+H]⁺ 750.5/752.5, m/z [M−H]⁻ 748.4/750.4; UPLC-MS 1

LC-MS: Rt=5.29 min; MS m/z [M+H]⁺ 750.2/752.2, m/z [M−H]⁻ 748.2/750.2; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.68 (s, br, 2H), 8.56 (d, J=8.1 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.94 (d, J=8.1 Hz, 1H), 7.50 (d, J=5.1 Hz, 1H), 6.72 (m, 1H), 5.34 (s, 2H), 4.53 (m, 1H), 3.52 (m, 4H), 3.28 (m, 4H), 2.98 (m, 3H), 2.80 (m, 1H), 2.63 (m, 1H), 2.55 (m, 1H), 2.46 (m, 1H), 2.16 (m, 2H), 1.95 (m, 1H), 1.68 (m, 1H), 1.17 (t, J=7.3 Hz, 3H)

Example 24b: The product containing fractions were concentrated at 40° C. and washed with n-pentane (5×10 mL), decanted and dried to give the title compound as an off-white solid—second eluting stereoisomer.

Chiral HPLC (C-HPLC 2): Rt=18.800 min

LC-MS: Rt=1.08 min; MS m/z [M+H]⁺ 750.1/752.1, m/z [M−H]⁻ 748.2/750.2; UPLC-MS 1

LC-MS: Rt=5.30 min; MS m/z [M+H]⁺ 750.1/752.1, m/z [M−H]⁻ 748.2/750.2; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.83 (s, br, 1H), 10.55 (s, br, 1H), 8.56 (d, J=8.2 Hz, 1H), 8.06 (d, J=5.3 Hz, 1H), 7.92 (d, J=8.2 Hz, 1H), 7.55 (d, J=5.3 Hz, 1H), 6.72 (m, 1H), 5.35 (s, 2H), 4.54 (m, 1H), 3.54 (m, 4H), 3.28 (m, 3H), 3.25 (m, 1H), 2.99 (m, 3H), 2.81 (m, 1H), 2.62 (m, 1H), 2.41 (m, 2H), 2.16 (m, 2H), 1.96 (m, 1H), 1.66 (m, 1H), 1.18 (t, J=7.3 Hz, 3H)

Example 25

[Figure (not displayed)]

N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)-2-(5-ethyl-2-(4-methoxycyclohex-1-en-1-yl)-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide.HCl (Intermediate Y) (120 mg, 190 μmol) and DIPEA (166 μL, 950 μmol) were dissolved in DCM (5 mL) and then 3-hydroxypicolinoyl chloride (Intermediate CV) (59.9 mg, 380 μmol) was added at 0° C. and stirred for 2 hours. 3-hydroxypicolinoyl chloride (Intermediate CV) (59.9 mg, 380 μmol) was added again and the reaction was continued under stirring for 12 hours. The RM was diluted with DCM and washed with water and aq NaHCO₃(2×20 mL), washed with water and brine, dried over Na₂SO₄, filtered and concentrated. The crude product was combined with another experiment and purified by column chromatography (Silica gel column: Silica 4 g, eluent DCM:MeOH 100:0 to 99:1) then further purified by reverse phase preparative HPLC (RP-HPLC acidic 10: 40 to 50% B in 2 min, 50 to 60% B in 8 min) to give the title compound as an off-white solid.

The racemate was purified by preparative chiral HPLC (instrument: Agilent 1200 series, with single quad mass spectrometer; column: CELLULOSE-4, 250 mm×21.2 mm; eluent: A=hexane, B=0.1% HCOOH in MeOH:EtOH 1:1; flow rate: 20 mL/min; detection: 210 nm; injection volume: 0.9 mL; gradient: isocratic 60(A):40(B)).

Example 25a: First eluting stereoisomer, off-white solid.

Chiral HPLC (C-HPLC 1): Rt=10.070 min

LC-MS: Rt=0.98 min; MS m/z [M+H]⁺ 716.5/718.6, m/z [M−H]⁻ 714.3/716.3; UPLC-MS 1

LC-MS: Rt=4.76 min; MS m/z [M+H]⁺ 716.2/718.2, m/z [M−H]⁻ 714.2/716.2; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.46 (s, br, 2H), 8.56 (d, J=8.5 Hz, 1H), 8.05 (m, 1H), 7.90 (d, J=8.4 Hz, 1H), 7.28 (m, 2H), 6.72 (m, 1H), 5.30 (s, 2H), 4.54 (m, 1H), 3.47 (m, 4H), 3.27 (s, 3H), 3.21 (m, 1H), 2.96 (m, 3H), 2.79 (m, 1H), 2.59 (m, 3H), 2.43 (m, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.67 (m, 1H), 1.17 (t, J=7.2 Hz, 3H)

Example 25b: Second eluting stereoisomer, off-white solid.

Chiral HPLC (C-HPLC 1): Rt=16.023 min

LC-MS: Rt=0.96 min; MS m/z [M+H]⁺ 716.3/718.3, m/z [M−H]⁻ 714.3/716.3; UPLC-MS 1

LC-MS: Rt=4.77 min; MS m/z [M+H]⁺ 716.2/718.2, m/z [M−H]⁻ 714.2/716.2; UPLC-MS 2

¹H NMR (400 MHz, DMSO-d₆) δ 10.39 (s, br, 2H), 8.56 (d, J=8.0 Hz, 1H), 8.06 (m, 1H), 7.93 (d, J=8.1 Hz, 1H), 7.28 (m, 2H), 6.72 (m, 1H), 5.32 (s, 2H), 4.54 (m, 1H), 3.46 (m, 4H), 3.27 (s, 3H), 3.20 (m, 1H), 2.96 (m, 3H), 2.79 (m, 1H), 2.59 (m, 3H), 2.41 (m, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.68 (m, 1H), 1.17 (t, J=7.1 Hz, 3H)

US11878973B2. Bicyclic compounds and their uses (2024-01-23). NOVARTIS AG [CH]. Inventors: Vincent Bordas [FR], Jvan Brun [CH], Markus Furegati [CH], Jacques Hamon [FR], Jürgen Hans-Hermann Hinrichs [DE], Philipp Holzer [CH], Fatma Limam [FR], Henrik Möbitz [DE], Sandro Nocito [CH], Simone Plattner [DE], Niko Schmiedeberg [CH], Joseph Schoepfer [CH], Ross Sinclair Strang [FR], Frédéric Zecri [US].

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Patent 2024

1-hydroxybenzotriazole 1H NMR acetamide Acids Bicarbonate, Sodium Bicyclo Compounds brine Cellulose Chlorides Chromatography DIPEA Ethanol H 718 Hexanes High-Performance Liquid Chromatographies Morpholinos pentane Piperazine Pressure pyridine Silica Gel Silicon Dioxide Stereoisomers Sulfoxide, Dimethyl Tandem Mass Spectrometry

Synthesis of Fluorescent Labeling Probe

Not available on PMC !

Example 125

[Figure (not displayed)]

Methyl 4-((5-(benzyloxy)-2-methoxyphenyl)(ethyl)amino)butanoate (184). 5-(Benzyloxy)-N-ethyl-2-methoxyaniline (146) (0.681 g, 2.65 mmol), DIEA (0.92 mL, 5.3 mmol), and methyl 4-iodobutyrate (0.72 mL, 5.3 mmol) in DMF (5 mL) were stirred at 70° C. for 5 days. The reaction mixture was cooled to rt, diluted with EtOAc (60 mL), washed with water (4×50 mL), brine (75 mL), dried over Na₂SO₄and evaporated. The residue was purified by chromatography on a silica gel column (2.5×30 cm bed, packed with CHCl₃), eluant: 5% MeOH in CHCl₃to get compound 184 (0.72 g, 76%) as a dark amber oil.

Methyl 4-(ethyl(5-hydroxy-2-methoxyphenyl)amino)butanoate (186). Ester 184 (0.72 g, 2.0 mmol) was stirred under reflux with 6 mL of water and 6 mL of conc HCl for 1.5 hrs and then evaporated to dryness to give acid 185 as a brown gum. The crude acid was dissolved in 50 mL of methanol containing 1 drop (cat.) of methanesulfonic acid ant the solution was kept for 2 hrs at rt. After that the mixture was concentrated in vacuum and the residue was mixed with 20 mL of saturated NaHCO₃. The product was extracted with EtOAc (3×40 mL). The extract was washed with brine (40 mL), dried over Na₂SO₄and evaporated. The residue was purified by chromatography on a silica gel column (2.5×30 cm bed, packed with CHCl₃), eluant: 5% MeOH in CHCl₃to get compound 186 (0.444 g, 83%) as a brown oil.

N-(6-(dimethylamino)-9-(4-(ethyl(4-methoxy-4-oxobutyl)amino)-2-hydroxy-5-methoxyphenyl)-3H-xanthen-3-ylidene)-N-methylmethanaminium chloride (187). To a stirred suspension of tetramethylrhodamine ketone 101 (0.234 g, 0.830 mmol) in 10 mL of dry chloroform was added oxalyl chloride (72 μL, 0.82 mmol) upon cooling to 0-5° C. The resulting red solution was stirred for 0.5 h at 5° C., and the solution of compound 186 (0.222 g, 0.831 mmol) in dry chloroform (5 mL) was introduced. The reaction was allowed to heat to rt, stirred for 72 h, diluted with CHCl₃(100 mL and washed with sat. NaHCO₃solution (2×30 mL) The organic layer was extracted with 5% HCl (3×25 mL). The combined acid extract was washed with CHCl₃(2×15 mL; discarded), saturated with sodium acetate and extracted with CHCl₃(5×30 mL). The extract was washed with brine (50 mL), dried over Na₂SO₄and evaporated. The crude product was purified by chromatography on silica gel column (2×50 cm bed, packed with CHCl₃/MeOH/AcOH/H₂O (100:20:5:1)), eluant: CHCl₃/MeOH/AcOH/H₂O (100:20:5:1) to give the product 187 (0.138 g, 29%) as a purple solid.

4-((4-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)-5-hydroxy-2-methoxyphenyl)(ethyl)amino)butanoate (188). Methyl ester 187 (0.136 g, 0.240 mmol) was dissolved in 5 mL of 1M KOH (5 mmol). The reaction mixture was kept at rt for 1.5 hrs and the acetic acid (1 mL) was added. The mixture was extracted with CHCl₃(4×30 mL), and combined extract was washed with brine (20 mL), filtered through the paper filter and. The crude product was purified by chromatography on silica gel column (2×50 cm bed, packed with MeCN/H₂O (4:1)), eluant: MeCN/H₂O/AcOH/(4:1:1) to give the product 188 (0.069 g, 98%) as a purple solid.

N-(6-(dimethylamino)-9-(4-((4-(2,5-dioxopyrrolidin-1-yloxy)-4-oxobutyl)(ethyl)amino)-2-hydroxy-5-methoxyphenyl)-3H-xanthen-3-ylidene)-N-methylmethanaminium chloride (189). To a solution of the acid 188 (69 mg, 0.12 mmol) in DMF (2 mL) and DIEA (58 μL, 0.33 mmol) was added N-hydroxysuccinimide trifluoroacetate (70 mg, 0.33 mmol). The reaction mixture was stirred for 30 min, diluted with chloroform (100 mL) and washed with water (5×50 mL), brine (50 mL), filtered through paper and concentrated in vacuum. The crude product was purified by precipitation from CHCl₃solution (5 mL) with ether (20 mL) to give compound 189 (55 mg, 67%) as a purple powder.

US11867698B2. Fluorogenic pH sensitive dyes and their method of use (2024-01-09). Life Technologies Corporation [US]. Inventors: Jeffrey Dzubay [US], Kyle Gee [US], Vladimir Martin [US], Aleksey Rukavishnikov [US], Daniel Beacham [US].

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Patent 2024

Acetic Acid Acids Amber Anabolism Bicarbonate, Sodium brine Chlorides Chloroform Chromatography Esters Ethyl Ether Hydroxyl Radical Ketones methanesulfonic acid Methanol N,N-diisopropylethylamine N-hydroxysuccinimide oxalyl chloride Powder Silica Gel Sodium Acetate tetramethylrhodamine Trifluoroacetate Vacuum

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DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.

Hydrochloric acid (hcl) by Merck Group

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Hydrochloric acid is a commonly used laboratory reagent. It is a clear, colorless, and highly corrosive liquid with a pungent odor. Hydrochloric acid is an aqueous solution of hydrogen chloride gas.

Acetonitrile by Merck Group

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Acetonitrile is a colorless, volatile, flammable liquid. It is a commonly used solvent in various analytical and chemical applications, including liquid chromatography, gas chromatography, and other laboratory procedures. Acetonitrile is known for its high polarity and ability to dissolve a wide range of organic compounds.

Gallic acid by Merck Group

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Gallic acid is a naturally occurring organic compound that can be used as a laboratory reagent. It is a white to light tan crystalline solid with the chemical formula C6H2(OH)3COOH. Gallic acid is commonly used in various analytical and research applications.

Formic acid by Merck Group

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Formic acid is a colorless, pungent-smelling liquid chemical compound. It is the simplest carboxylic acid, with the chemical formula HCOOH. Formic acid is widely used in various industrial and laboratory applications.

Penicillin streptomycin by Thermo Fisher Scientific

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Penicillin/streptomycin is a commonly used antibiotic solution for cell culture applications. It contains a combination of penicillin and streptomycin, which are broad-spectrum antibiotics that inhibit the growth of both Gram-positive and Gram-negative bacteria.

What are the different types of acids and their characteristics?

Acids can be classified into two main categories: organic acids and inorganic acids. Organic acids, such as acetic acid (found in vinegar) and citric acid (found in citrus fruits), are carbon-based and are typically weaker in strength. Inorganic acids, such as sulfuric acid and hydrochloric acid, are not carbon-based and tend to be stronger in strength. Acids can also be classified by their ionization strength, with strong acids (e.g., hydrochloric acid) completely dissociating in water, while weak acids (e.g., acetic acid) only partially dissociate. Understanding these acid characteristics is important when selecting the appropriate acid for your research needs.

What are some common applications of acids in research and industry?

Acids have a wide range of applications in research and industry. In chemistry and biochemistry, acids are used in various analytical techniques, such as titrations, to determine the concentration of substances. They are also used in the synthesis of organic compounds and the purification of materials. In the pharmaceutical industry, acids are used in the production of certain drugs and in the formulation of medications. In the food industry, acids like citric acid are used as preservatives and flavorings. In the mining and metallurgy industries, acids are used for etching, cleaning, and extracting metals from ores. Understandign the diverse applications of acids is crucial for optimizing your research and industrial processes.

How can PubCompare.ai help researchers when working with acids?

PubCompare.ai can be a valuable tool for researchers working with acids. The platform allows you to efficiently screen the protocol literature and leverage AI to pinpoint critical insights. By using PubCompare.ai, you can identify the most effective protocols related to acids for your specific research goals. The platform's AI-driven analysis can highlight key differences in protocol effectiveness, enabling you to choose the best option for reproducibility and accuracy. This can save you time and effort, and help you optimize your research workflow when working with acids.

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