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Diantipyrylmethane CAS 1251-85-0, also known as bis-antipyrine methane, is a chemical agent with specific physical and chemical properties. Structural formula: C23H24N4O2; Molecular weight: 388.46 or 406.48. It is primarily used as a sensitive detection reagent for titanium and iron. It is also used as a weight and solvent extractant for various metal ions.
Appearance: White flaky crystals; Melting point: 179°C; Boiling point: 514.17°C; Solubility: insoluble in water, ether and alkali, but soluble in acid, ethanol and trichloromethane. Water solubility at 20°C is 439mg/L; Storage at 4°C or -4°C is recommended to maintain its stability and performance.
It is often used as a sensitive reagent for the determination of titanium and iron content, and this property makes it valuable for chemical analysis and laboratory testing; It can be used as a sensitive color developer for the determination of Au³⁺, Ti⁴⁺, Ir, Fe(III), Molybdenum, Neodymium, Uranium(VI), Iridium, Platinum, Rhenium and other metal ions by Spectrophotometric and Extractive Photometric methods; In weighing analysis, it can be used as a precipitant for the determination of silicon content for the accurate determination of silicon content; it can also be used as an extractant for various ions, which is an important application value in the chemical separation and purification process.
As a chemical reagent, it has important applications in a variety of fields such as metal ion detection, analysis, silicon content determination and ion extraction. These applications are based on its unique chemical properties and reaction characteristics with various ions.
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Chemical Formula |
C23H24N4O2 |
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Exact Mass |
388 |
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Molecular Weight |
388 |
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m/z |
388 (100.0%), 389 (24.9%), 390 (2.7%), 389 (1.5%) |
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Elemental Analysis |
C, 71.11; H, 6.23; N, 14.42; O, 8.24 |
Used as a colorimetric reagent for titanium detection. It forms a yellow color complex with Ti in 0.5-4.0 M HCl solution, and the detection range is 0.2-3.0 ppm.
Reaction of diantipyrylmethane with titanium
Reaction conditions:
In a 0.5-4.0 M HCl solution, diantipyrylmethane reacts with Ti.
Reaction product:
Formation of a yellow complex with a specific absorption spectrum, λ max=385~390 nm, ε=15000.
Detection range:
The concentration range of titanium that can be detected by colorimetric method is 0.2~3.0 ppm.
The use of diantipyrylmethane
Titanium detection:
Used as a colorimetric reagent for sensitive detection of titanium.
Extractant:
It can also be used for weight and solvent extraction of various metal ions.
Chromogenic reagent:
Used for the determination of multiple elements by spectrophotometry and extraction photometry by forming specific colored complexes or associations.
It can be used as the weight and solvent extractant of various metal ions, such as Au³⁺, Ti⁴⁺, Ir, Fe(III), Mo, Nd, U(VI), Iridium, Platinum, Rhenium and so on.
used as precipitant for the determination of silicon in weighing analysis.
Diantipyrylmethane has multiple uses in chemical analysis, particularly in the following areas:
(1) Silicon precipitant:
In weighing analysis, diantipyrylmethane can be used as a precipitant for determining silicon. Through specific chemical reactions, silicon ions are precipitated to achieve accurate quantitative analysis.
(2) Sensitive chromogenic reagent:
It is also widely used as a sensitive chromogenic reagent for the determination of elements such as Au3+, Ti4+, Ir, iron (III), molybdenum, neodymium, uranium (VI), iridium, platinum, rhenium, etc. by spectrophotometry and extraction photometry. After reacting with diantipyrylmethane, these elements will form specific colored complexes or associations, which can be determined by spectrophotometry or extraction photometry.
(2) Extractant:
In addition, diantipyrylmethane can also be used as an extractant for various ions, transferring target ions from one solvent to another through extraction, achieving ion separation and enrichment.
Used as sensitive color developer in spectrophotometry and extraction photometry.
Diantipyrylmethane is a multifunctional chemical reagent, widely used in the detection of titanium and other metal ions, weighing analysis and other fields, and used as a sensitive color developer. When used, its safety information and storage conditions should be observed.
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Significant Applications in Titanium Detection
Diantipyrylmethane has significant applications in titanium detection. The following is a list of specific applications and information about its use in titanium detection:
- It is a colorimetric reagent commonly used in titanium testing. It is capable of forming stable complexes with titanium ions under specific conditions and producing specific color changes.
- In 0.5-4.0 M HCl solution, it forms a yellow complex with Ti with a maximum absorption wavelength (λmax) of 385-390 nm and a molar absorption coefficient (ε) of up to 15,000.
- It showed high sensitivity in the titanium assay with a detection range of 0.2-3.0 ppm.
- The detection accuracy and range can be further improved by optimizing the analytical conditions, such as using the highly sensitive and stable spectrophotometric method.
In the presence of I-, SCN-, tartaric acid or catechol, the resulting Ti complexes can be extracted by organic solvents, further simplifying the titanium detection process
4.Standard Methods and Practical Applications:
- The GB/T 13747.19-2017 standard specifies the methods for the determination of titanium content in zirconium and zirconium alloys, which includes the spectrophotometric method.
- The method is suitable for the determination of titanium content in zirconium sponge, zirconium and zirconium alloys with certain detection range and accuracy.
5.Optimization and Application Promotion:
- By reasonably optimizing the analytical conditions, the diamantipyrine methane photometric method is able to be used with a high-range spectrophotometer for the determination of titanium dioxide content in titanium concentrates, vanadium-titanium magnetite and high titanium slag.
- The method is fast and simple to analyze, and its precision is better than the existing industry standards, so it is worth to be popularized and applied.
synthesis Methods
Reagent preparation
- Diantipyrylmethane: Used as a colorimetric reagent to form stable complexes with titanium ions.
- Inorganic acids (e.g. HCl): used to adjust the acidity of the solution, usually analyzed in 0.5-4.0 M HCl solution.
Analyzing conditions
- Solution pH: usually performed under weakly acidic conditions to ensure stable complexation with titanium ions.
- Wavelength: the maximum absorption wavelength (λmax) of the complex is 385-390 nm.
- Molar absorption coefficient: ε=15,000, showing high sensitivity.
Analytical steps
- Sample treatment: Depending on the nature of the sample, appropriate dissolution and dilution steps may be required.
- Complex formation: It is added to the sample solution at the specified HCl concentration to form a yellow complex with titanium ions.
- Extraction (optional): The resulting Ti complex can be extracted by organic solvents in the presence of I-, SCN-, tartaric acid, or catechol to improve analytical accuracy and selectivity.
- Photometric measurements: the absorbance of the complexes was measured at λmax = 385-390 nm using a spectrophotometer.
Calculation of results
- From the measured absorbance and the known molar absorption coefficient, the concentration of titanium ions in the sample can be calculated.
- Quantitative analysis can be performed using standard curves or regression equations, e.g. A = 1.5684 × w + 0.0141 (where A is the absorbance and w is the concentration of titanium).
Precautions
Other ions that may be present in the sample may interfere with the analysis and require proper masking or separation. The purity of the reagents and the storage conditions of the solution may affect the accuracy of the analytical results. By following the above steps and points, titanium can be analyzed accurately and reliably using it.
Stability and safety of the Diantipyrylmethane
- Physical stability: It is a white flaky crystal at room temperature with a melting point of 156°C (dec.) (lit.) or 179°C (depending on the reference). The boiling point is 515.177°C at 760 mmHg or 515.2±60.0°C at 760 mmHg, indicating good thermal stability under conventional conditions.
- Chemical Stability: It is stable when stored under sealed, dry and room temperature conditions. However, it should be noted that it is not compatible with strong oxidizing agents.
- Hazardous Material Marking: It is labeled as a hazardous material and therefore requires special care in handling and use.
- Safety Instructions: According to references, safety instructions for it include 22-24/25, these numbers correspond to specific safety precautions and first aid measures.
- Storage Conditions: Storage at low temperatures between 4°C and -4°C is recommended to optimize its preservation.
- Toxicity Information: Although specific toxicity data are not mentioned in the referenced article, it can be assumed that it may be toxic due to its classification as a hazardous material. Therefore, it is necessary to wear appropriate protective equipment and follow relevant safety procedures when handling and using it.
In summary, it has good physical and chemical stability under conventional conditions, but special attention should still be paid to its safety and incompatibility with strong oxidizing agents during storage and use. To ensure its safety and stability, it is recommended to keep it under proper storage conditions and follow the relevant safety operation procedures when handling and using it.
Diantipyrylmethane (DAM) is an important organic compound and a derivative of antipyrine. It has a wide range of applications in fields such as analytical chemistry, medicinal chemistry, and materials science, especially exhibiting excellent coordination ability in metal ion colorimetric analysis and photometric determination. The discovery of Antipyrine, a precursor compound of Diantipyrylmethane, can be traced back to the late 19th century. In 1883, German chemist Ludwig Knorr first synthesized antipyrine while studying pyrazole compounds. Knorr's original goal was to study the synthesis method of quinoline alkaloids, but during the experiment, a compound with significant antipyretic and analgesic effects, namely antipyretic pyrine, was unexpectedly discovered. The synthesis route of Knorr is as follows:
- Phenylhydrazine (C ₆ H ₅ NHNH ₂) condenses with ethyl acetoacetate (CH ∝ COCH ₂ COOEt) to form 1-phenyl-3-methyl-5-pyrazolone.
- Further methylation yields 1,5-dimethyl-2-phenyl-3-pyrazolone, also known as antipyrine.
- This discovery not only advances the research of pyrazole compounds, but also promotes the widespread application of antipyrine in the pharmaceutical field.
Antipyrine quickly became an important drug in the late 19th and early 20th centuries due to its excellent antipyretic and analgesic effects. It was widely used to treat fever, headache, and rheumatic pain, and became one of the most commonly used nonsteroidal anti-inflammatory drugs at that time. However, with a deeper understanding of the side effects of antipyrine, such as neutropenia, its clinical use has gradually decreased, but its derivatives, such as aminopyrine and metamaterial, still hold a place in the pharmaceutical field. At the beginning of the 20th century, with the development of antipyrine chemistry, researchers began to explore the synthesis and application of its derivatives. The synthesis of Diantipyrylmethane (DAM) originated from the study of the active sites in antipyrine molecules. Due to the high reactivity of the pyrazolone ring of antipyrine, especially its ability to undergo condensation reactions under acidic conditions, scientists have attempted to construct new molecular structures by reacting antipyrine with aldehyde compounds. In the 1930s, Soviet chemist Ivan Pavlovich Alimarin and his team first reported the synthesis of Diantipyrylmethane while studying the derivatization reaction of antipyrine. They found that under acidic conditions (such as sulfuric acid or hydrochloric acid catalysis), two molecules of antipyrine can condense with formaldehyde (HCHO) to form DAM. The key to this reaction lies in the strong nucleophilicity of the 4-position carbon atom of antipyrine, which can undergo nucleophilic addition with the carbonyl carbon of formaldehyde, followed by dehydration to form a symmetrical molecule connected by a methylene bridge (- CH ₂ -).
Dimethoxyantipyrine methane (DAPM), as a class of organically unique compounds, has established a comprehensive knowledge system encompassing its chemical properties, synthetic methods, and application scenarios. From serving as color developers and precipitating agents in traditional analytical chemistry to emerging roles as fluorescent probes and antitumor drug carriers, DAPM continues to push the boundaries of scientific exploration. Looking ahead, breakthroughs in green synthesis technologies and deepening interdisciplinary research hold promise for this classic compound to catalyze more disruptive applications across energy, environmental, and medical fields, contributing fresh chemical insights to human societal progress.
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