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5-Sulfoisophthalic acid monosodium salt, molecular formula C8H7NaO7S, CAS 6362-79-4, is a stable white powder under normal temperature and pressure. It dissolves in water, has irritant and corrosive properties, and has a certain harmful effect on water bodies. With its unique ionic properties and multifunctional structure, it has become a core raw material in the fields of polymer material modification, pharmaceutical synthesis, and environmentally friendly coatings. Its technological advantages (low cost, good environmental friendliness) and performance breakthroughs (high hardness, strong weather resistance) have jointly promoted its deepening application in traditional fields and expansion in emerging fields. With the deepening of green chemistry and sustainable development concepts, 5-SSIPA is expected to become one of the key materials for the transformation and upgrading of the chemical industry in the future.

|
Chemical Formula |
C8H5NaO7S |
|
Exact Mass |
268 |
|
Molecular Weight |
268 |
|
m/z |
268 (100.0%), 269 (8.7%), 270 (4.5%), 270 (1.4%) |
|
Elemental Analysis |
C, 35.83; H, 1.88; Na, 8.57; O, 41.76; S, 11.96 |

5-Sulfoisophthalic acid monosodium salt(5-SSIPA, molecular formula C ₈ H ₅ NaO ₇ S) is an aromatic dicarboxylic acid derivative with sodium sulfonate group as its functional core. Its unique molecular structure endows it with ionic properties, making it irreplaceable in fields such as dyes, pharmaceuticals, polymer materials, and environmentally friendly coatings.
1. Polyester dyeing modification: breaking through the limitations of traditional dyes
Sodium isophthalice-5-sulfonate, as the third monomer of polyester fibers, introduces sodium sulfonate groups through copolymerization to form permanent negative charge centers on the fiber surface. This characteristic increases its adsorption capacity for cationic dyes (such as Disperse Red and Disperse Blue) by 3-5 times, increases the dyeing depth by 20% -30%, and has significantly better wash fastness (≥ 4 levels) and light fastness (≥ 6 levels) than conventional polyester.
For example, winter clothing fabrics made of 5-SSIPA modified polyester can achieve high saturation dyeing of dark colors (such as navy blue and dark green), and after 50 washes, the color difference Δ E is ≤ 1.5, meeting the strict durability requirements of the high-end clothing market.
2. Synthesis of waterborne polyester resin: the cornerstone of environmentally friendly coatings
Traditional polyester resins rely on organic solvents such as toluene and xylene for dissolution, while 5-SSIPA can directly form a stable dispersion system with water through the ionic properties of sodium sulfonate groups. The synthesis process is divided into two steps:
Preparation of high acid value resin: Using 5-SSIPA, PTA, and ethylene glycol (EG) as raw materials, condensation is carried out at 220-240 ℃ to obtain a water-soluble polyester resin with an acid value (AV) of 60-80 mgKOH/g;
Amine neutralization reaction: triethylamine (TEA) or ammonia water is added to convert carboxyl group into ammonium salt to form nanometer lotion with particle size less than 50nm. After the lotion is coated on the metal substrate, the hardness of the formed coating can reach 3H (pencil hardness), the gloss (60 ° angle) ≥ 90, and the VOC (volatile organic compounds) content is less than 50g/L, which conforms to the European Union REACH regulations and the U.S. EPA standards.
3. Water based polyurethane dispersion: a breakthrough in high hardness coatings
5-SSIPA, as a hydrophilic chain extender, can replace traditional DMPA and significantly improve the stability of polyurethane dispersions. Its mechanism of action is as follows:
Molecular design optimization: The sodium sulfonate group is located between the benzene rings, with low steric hindrance and high reactivity with isocyanates (NCO). The reaction rate is twice that of DMPA;
Particle size control: By adjusting the dosage of 5-SSIPA (3% -8% of the polyol mass), the particle size of the dispersion can be controlled within the range of 80-120nm, forming a transparent or semi transparent system;
Performance improvement: The coating hardness can reach 4H, and its impact resistance (50kg · cm) and chemical resistance (resistance to soaking in 5% hydrochloric acid and 10% sodium hydroxide solution for 24 hours without change) are significantly better than solvent based polyurethane.
Pharmaceutical and Pesticide Intermediates: A Synthesis Platform for Bioactive Molecules
1. Drug delivery system (DDS) carrier
The sodium sulfonate group of 5-SSIPA can form nanocomposites with biomolecules such as proteins and peptides through electrostatic interactions, achieving targeted drug delivery. For example:
Antitumor drug carrier: 5-SSIPA was copolymerized with chitosan to prepare nanoparticles with particle size<200nm. After loading doxorubicin (DOX), the inhibition rate on breast cancer cells (MCF-7) increased by 40% compared with free drugs;
Gene therapy vector: By binding sodium sulfonate groups to the phosphate backbone of DNA, a stable core-shell structure is formed, and the transfection efficiency is 2-3 times higher than traditional polyethyleneimine (PEI) vectors.
2. Synthesis of bioactive molecules
The benzene ring structure of 5-SSIPA can be used as a synthetic platform to introduce halogens such as fluorine and chlorine through substitution reactions of sulfonic acid groups, or to connect long-chain alkyl groups through esterification reactions to prepare compounds with specific biological activities. For example:
Antibacterial agent: 5-SSIPA is reacted with cetylammonium bromide (CTAB) to prepare a surfactant antibacterial agent, with a minimum inhibitory concentration (MIC) of 16 μ g/mL against Staphylococcus aureus (ATCC 6538);
Anti inflammatory drugs: 5-mercapto-isophthalic acid is prepared through the reduction reaction of sulfonic acid groups, and thiazolidinone anti-inflammatory drugs are further synthesized. Its anti-inflammatory activity (IC ₅₀=0.5 μ M) is superior to dexamethasone (IC ₅₀=1.2 μ M).
Environmentally friendly Coatings and Food Packaging: Practitioners of Green Chemistry
1. Amine free water-based coatings: replacing traditional solvent based coatings
Traditional water-based polyester resins require the use of organic amines (such as triethylamine) to neutralize carboxyl groups, resulting in residual amine substances in the coating and the release of irritating odors. 5-Sulfoisophthalic acid monosodium salt achieves "amination free" synthesis through direct ionization of sodium sulfonate groups:
Process simplification: Omitting the amine neutralization step, reducing reaction time by 30% and energy consumption by 20%;
Performance optimization: The coating's water resistance (no foaming after 24 hours of immersion) and weather resistance (no powdering after 500 hours of QUV accelerated aging) have been significantly improved;
Application expansion: It has been widely used in automotive OEM paint, building exterior wall coatings, and industrial anti-corrosion coatings, and its market share has been increasing year by year.
2. Food packaging adhesive: FDA certified safety guarantee
The polyester resin synthesized by 5-SSIPA has been certified by FDA 21 CFR 175.300 and can be used for packaging materials that come into direct contact with food, such as beverage bottle labels and fast food box adhesives. Its security stems from:
Low mobility: The sodium sulfonate group is covalently bonded to the polyester main chain, and under 40 ℃ and 100% humidity conditions, the migration amount is less than 0.1mg/dm ²;
High temperature resistance: Glass transition temperature (Tg) of 80-100 ℃, able to withstand pasteurization (65 ℃, 30min) and hot filling (85 ℃) processes;
Non toxic by-products: No heavy metal catalysts (such as tin compounds) are required during the synthesis process to avoid the risk of heavy metal residue.
1. Magnetic tape adhesive: high-performance data storage medium
The adhesive prepared by copolymerization of 5-SSIPA and acrylic ester can be used for fixing the magnetic powder layer of magnetic tapes (such as data backup tapes and audio tapes). Its advantages include:
High bonding strength: The peel strength (180 °) reaches 5N/25mm, which is 30% higher than traditional polyurethane adhesives;
Wear resistance: After 500 cycles of friction testing, the magnetic powder detachment rate is less than 0.5%;
Temperature resistance: Can be used for a long time within the range of -40 ℃ to 80 ℃, suitable for extreme environmental storage needs.
2. Ink additives: improve printing quality
5-SSIPA, as a dispersant and stabilizer, can improve the rheological properties and printing adaptability of ink:
Particle size control: Disperse pigment particles to<1 μ m to improve ink transparency and color saturation;
Anti settling property: After 6 months of ink storage, the pigment settling rate is less than 5% to avoid clogging during printing;
Fast drying: By utilizing the water absorption of sodium sulfonate groups, it accelerates the drying of ink on the surface of the substrate, resulting in a 20% increase in printing speed.

5-Sulfoisophthalic acid monosodium salt Synthesis method:
Method 1:
Reaction of sodium terephthalate and 5-nitroisobenzene (or 5-nitroisophthalic acid):
This method is one of the most versatile for the synthesis of product. First, sodium terephthalate is dissolved in water and then converted to its acid form using 10% sulfuric acid as a catalyst. Next, 1.2 equivalents of sodium nitrite was used for nitration reaction to prepare 5-nitroisophthalic acid. Finally, purification and neutralization treatment to obtain it.
Method 2:
Synthesis of p-toluenesulfonic acid and carbene:
The method is obtained by tosylation of terephthalic acid. First, terephthalic acid was dissolved in anhydrous methanol and reacted with toluenesulfonic acid to form an intermediate (C6H4(CO2CH3)2CH2SO3H2). The intermediate is then converted to product by adding a base such as sodium hydroxide or sodium carbonate. During the neutralization process, due to the acidity generated, the amount of alkali used is a little more than the theoretical value.

Method 3:
The carboxylation reaction of isobutyl terephthalate:
Different from Method 1, Method 3 is based on the synthesis of terephthalic acid ester groups rather than acid groups. First, isobutyl terephthalate reacts with bromoacetic acid to produce 123-trimethyl-1,4-dibromobenzene diacetate. Excess acrylic acid and hydroxypropanesulfonic acid are then rearranged by Reißert to convert to it.
Method 4:
Reaction of terephthalamide and 2,3-dichlorobenzenesulfonic acid:
The method uses terephthalamide and 2,3-dichlorobenzenesulfonic acid to react with absolute ethanol as a solvent. The intermediates produced by the reaction are exposed to the air to form metal carbonyl complexes by autoxidation. Finally, the complex was reduced by dropwise addition of methylene blue solution and neutralized so that the carboxylic acid moiety yielded product.
Method 5:
The reaction of terephthalate and benzoxanesulfonyl chloride:
This method is esterified to tert-butyl sulfate and subsequently reacted with benzoxanesulfonyl chloride in dichloromethane. The reaction produces high molecular weight benzoxane sulfate. Finally, through neutralization, 5-Sulfoisophthalic acid monosodium salt is generated.
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