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Xylenol Orange disodium salt, The Chinese name is xylenol orange disodium salt, also known as xylenol orange yellow, S-dioxane xylenol orange, or xylenol orange yellow disodium salt. The appearance is usually a reddish brown to dark red powder or crystal, easily soluble in water and insoluble in anhydrous ethanol. It appears red in aqueous solution, lemon yellow in acidic solution, bright red in metal complexes, and reddish purple in alkaline solution. When preparing, xylenol orange is usually used as a 0.2% aqueous solution, and the concentration can be adjusted as needed. When preparing, it should be ensured that it is fully dissolved and stored under appropriate conditions. It is used as an indicator for titrating various metals such as zinc, bismuth, cadmium, cobalt, copper, iron, mercury, indium, lanthanide elements, nickel, lead, scandium, thorium, zirconium, thallium, uranium (VI), vanadium, etc. Under specific pH conditions, xylenol orange can display different colors and can therefore also be used as an acid-base indicator.
Additional information of chemical compound:
|
Chemical Formula |
C31H30N2O13S2- |
|
Exact Mass |
670.15 |
|
Molecular Weight |
670.64 |
|
m/z |
335.07(100.0%),335.58(33.5%),336.08(5.4%),336.07(4.5%), 336.08 (1.6%), 336.57 (1.5%), 336.08 (1.0%) |
|
Elemental Analysis |
C, 55.52; H, 4.51; N, 4.18; O, 31.01; S, 4.78 |
|
Melting point |
195 °C (dec.)(lit.) |
|
Density |
250kg/m3 |
 |
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Xylenol Orange disodium salt is an important chemical reagent with multiple uses. The following is a detailed explanation of its uses:
This substance, as a sensitive photometric reagent, is widely used in photometric determination of various metal ions. Its metal complex has a distinct color change, making it an ideal choice for detecting metal ions. Through photometry, the content of metal ions in samples can be accurately and quickly determined, providing strong data support for scientific research and production. Specifically, it can be used to determine various metal ions such as zinc, aluminum, beryllium, bismuth, lanthanum, niobium, nickel, palladium, thorium, yttrium, zirconium, etc. During the measurement process, the substance forms a stable complex with metal ions and is measured by colorimetric or spectrophotometric methods. This method has the advantages of easy operation, high sensitivity, and good accuracy, and is therefore widely used in fields such as environmental monitoring, food safety, pharmaceuticals, and chemical engineering.
Complexation indicator
This substance is also a commonly used chelating indicator and has a wide range of applications in complexometric titration. Complexation titration is a method of determining the content of metal ions by forming metal chelating agent complexes. As an indicator, it can sensitively indicate the endpoint of titration, thereby improving the accuracy and reliability of the determination. In complexometric titration, xylenol orange is usually used together with chelating agents such as EDTA. When metal ions form stable complexes with chelating agents such as EDTA, the color of xylenol orange yellow disodium salt changes, indicating the endpoint of titration. This method has the advantages of easy operation, high sensitivity, and good accuracy, and is therefore widely used for the determination of various metal ions.
In addition to being used as a photometric reagent and chelating indicator, xylenol orange can also be used as an acid-base indicator. In acid-base titration, the color of xylenol orange yellow changes with the pH value of the solution, indicating the endpoint of the titration. This method has the advantages of intuitiveness and simplicity, and is therefore widely used in various acid-base titration experiments.
other purposes
In addition to the main uses mentioned above, xylenol orange yellow also has other potential applications. For example, it can be used as a dye in the textile industry; Used as a raw material for fluorescent whitening agents in the paper industry; Used as a raw material for antioxidants in the food industry, etc. In addition, xylenol orange can also be used to prepare other chemical reagents and pharmaceutical intermediates.
Application examples
Application in environmental monitoring
Xylenol orange yellow disodium salt has a wide range of applications in environmental monitoring. For example, when measuring heavy metal ions in water, the spectrophotometric method using xylenol orange yellow disodium salt can be used for detection. By using colorimetric or spectrophotometric methods, the content of heavy metal ions in water can be accurately and quickly determined, providing strong data support for environmental protection. In addition, xylenol orange yellow disodium salt can also be used to determine the content of pollutants in the atmosphere. For example, when measuring sulfur dioxide in the atmosphere, the acid-base indicator properties of Xylenol orange yellow disodium salt can be used for detection. By observing the changes in solution color, the content of sulfur dioxide in the atmosphere can be determined, providing scientific basis for environmental pollution control.
Application in food safety
Xylenol orange yellow disodium salt also has a wide range of applications in the field of food safety. For example, when determining the content of metal elements in food, the photometric method of Xylenol orange yellow disodium salt can be used for detection. By using colorimetric or spectrophotometric methods, the content of metal elements in food can be accurately and quickly determined, providing strong guarantees for food safety. In addition, xylenol orange yellow disodium salt can also be used to detect the content of additives in food. For example, when determining the preservative content in food, the chelating indicator properties of Xylenol orange yellow disodium salt can be used for detection. By observing the changes in solution color, the content of preservatives in food can be determined, providing scientific basis for food quality control.
Application in Pharmaceutical and Chemical Industry
Xylenol orange yellow disodium salt also has a wide range of applications in the pharmaceutical and chemical industries. For example, in the preparation of pharmaceutical intermediates, the chemical properties of Xylenol orange yellow disodium salt can be utilized for synthesis reactions. By optimizing reaction conditions and controlling the reaction process, high-purity and high-yield drug intermediates can be obtained, providing strong support for drug development and production. In addition, xylenol orange yellow disodium salt can also be used to prepare other chemical reagents and dyes. For example, in the preparation of fluorescent whitening agents, the fluorescence properties of Xylenol orange yellow disodium salt can be utilized for synthesis reactions. By adjusting reaction conditions and selecting appropriate solvents, fluorescent whitening agent products with good fluorescence performance can be obtained.
Precautions for use
- Solubility: Xylenol orange disodium salt is easily soluble in water, but insoluble in anhydrous ethanol. Therefore, appropriate solvents should be selected when preparing the solution to ensure complete dissolution.
- Stability: Xylenol orange yellow disodium salt has a certain degree of stability in aqueous solution, but may decompose or deteriorate after prolonged storage or high temperature conditions. Therefore, before use, it should be checked for deterioration or failure, and stored and used correctly according to the requirements in the instructions.
- Safety: Xylenol orange yellow disodium salt has certain toxicity and irritation, and personal protection should be taken when using it. Avoid direct contact with sensitive areas such as skin and eyes, and wear appropriate protective equipment such as gloves, masks, etc. Meanwhile, attention should be paid to ventilation and air exchange during use to avoid inhaling harmful gases or vapors.
- Compatibility taboos: Under certain conditions, it may react or interact with other chemicals, leading to adverse effects such as color changes or precipitation formation. Therefore, before use, it is necessary to understand which substances it is incompatible with and avoid simultaneous use or contact.
- Environmental requirements: During use, pollutants such as waste or wastewater may be generated. Therefore, after use, it should be treated and discharged according to relevant environmental protection requirements to reduce pollution and damage to the environment.
What should be noted for this compound in environmental testing?
Solubility and stability
Ensure the solubility and stability of xylenol orange disodium salt in the measurement medium to avoid inaccurate measurement results due to incomplete dissolution or decomposition.
Interference factors
Pay attention to excluding other factors that may interfere with the measurement, such as coexisting ions, organic compounds, etc. These interfering factors may affect the complexation reaction or color change between xylenol orange yellow disodium salt and metal ions, leading to measurement result bias.
Safety protection
Xylenol orange yellow disodium salt may have certain toxicity and irritation. During use, laboratory safety regulations should be followed, appropriate protective equipment should be worn, and direct contact with sensitive areas such as skin and eyes should be avoided.
Calibration and validation
Before using xylenol orange disodium salt for measurement, calibration and validation experiments should be conducted to ensure the accuracy and reliability of the measurement results. This includes using standard solutions for calibration, comparing and verifying with other analytical methods, etc.
Adverse reactions
Chemical stimulation
Xylenol orange disodium salt is a chemical reagent with certain chemical activity. When in contact with the skin, eyes, or inhaling their dust, it may cause irritation to the skin, mucous membranes, etc., causing local discomfort such as skin redness, itching, eye pain, tears, etc. However, this stimulation can usually be relieved after timely cleaning or removal from contact, and there is currently no clear evidence to suggest that it causes serious, irreversible damage.
Allergic reactions
Some individuals may be allergic to xylenol orange disodium salt and may experience allergic reactions such as rash, urticaria, etc. upon contact. The occurrence of allergic reactions is related to the individual's immune system, and the degree and manifestations of allergic reactions may vary among different people. For individuals known to be allergic to the substance, contact should be strictly avoided.
Protective measures
Appropriate personal protective equipment, such as protective gloves, goggles, etc., should be worn when handling dimethyl phenol orange disodium salt to reduce direct contact between the skin and eyes and the substance. Follow the safety operating procedures of the laboratory or workplace, ensure that the operation is carried out in a well ventilated environment, and avoid inhaling its dust or gas. If you accidentally come into contact with xylenol orange disodium salt, immediately rinse the contact area with plenty of water and seek medical attention promptly.
Xylenol Orange Disodium Salt (XO) is a classic metal ion chromogenic reagent widely used in analytical chemistry, biological staining, and environmental monitoring. Its discovery history integrates accidental chemical synthesis, systematic structural optimization, and interdisciplinary application expansion. In the 1930s, German chemists devoted themselves to developing new color reagents, especially azo compounds containing sulfonic acid groups.
In 1935, Hans H. Schlubach of IG Farben (predecessor of Bayer) first reported the coupling reaction of ortho cresol derivatives with diazonium salts, laying the foundation for the subsequent synthesis of XO.
In 1942, Swiss chemist Gerold Schwarzenbach discovered that certain azo dyes could form stable complexes with metal ions and undergo color changes while studying EDTA (ethylenediaminetetraacetic acid). This discovery led to the birth of the concept of "metal color indicators".
In 1955, L á szl ó Erdey and Ferreg Gr ü n from Budapest Polytechnic University accidentally obtained an orange red compound while synthesizing a methylthymol blue analogue. Through elemental analysis and UV spectroscopy, they confirmed its structure as 3,3 '- bis [N, N-di (carboxymethyl) aminomethyl] - o-cresol sulfophthalein (i.e. Xylenol Orange).
The original XO had poor water solubility. In 1957, Karl Heinz Gump from Merck, Germany, prepared a more water-soluble form of disodium salt (C ③₁ H ₂ ₈ N ₂ Na ₂ O ₁ ∝ S) through a sulfonic acid group salt formation reaction, and found that its chelating ability with heavy metal ions (such as Bi ³ ⁺, Zr ⁴) was significantly improved.
In 1963, Soviet scientist Yuri A. Zolotov confirmed through X-ray diffraction that the sulfonic acid group and carboxymethyl amino group of XO form an octadentate coordination structure, which forms a 1:1 complex with metal ions (such as log Kf=15.2 with Fe ³ ⁺). The color development mechanism of XO is highly dependent on pH:
Acidic conditions (pH<3): Protonated form (H ₆ XO ² ⁺), yellow (λ max=440nm)
Neutral conditions (pH 6-7): turns reddish purple after binding with metal ions (λ max=560nm)
In the 1970s, XO became the preferred indicator for the EDTA titration method to determine Bi ³ ⁺ and Th ⁴⁺. Its advantages include:
Detection limit as low as 10 ⁻⁷ M
Strong anti-interference ability (not affected by alkaline earth metals)
Cellular calcium imaging: The zinc chelation properties of XO were used as a fluorescent probe for neuronal Zn ² ⁺ (improved by Tsien Laboratory in 1998)
Environmental Monitoring: In 2015, Japan developed a rapid lead pollution detection test strip based on XO (detection limit of 0.1ppm)
In 2009, the EU REACH regulation listed XO as a "potential mutagen" and promoted the development of low toxicity alternatives such as Calcein. Despite the challenges posed by new fluorescent probes such as the Zinpyr series, XO remains irreplaceable in industrial detection due to its low cost and high stability.
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