Maleic acid powder, also known as cis-butenedioic acid, is an organic dicarboxylic acid with the chemical formula C4H4O4. It exists naturally in certain fruits and plants but is primarily industrially produced through the oxidation of butenes, particularly butene-1 and butene-2. This colorless, crystalline compound has a distinct, acidic odor and is highly soluble in water and various organic solvents.
The molecular structure features a four-carbon chain with two carboxyl (-COOH) groups positioned in a cis configuration, meaning the carbon-carbon double bond and the carboxyl groups are on the same side of the molecule. This configuration gives it unique chemical properties, including its ability to form esters, anhydrides, and salts.
Moreover, maleic acid is utilized in the production of chelating agents, which help remove metal ions from solutions, and as a component in the formulation of dyes and pigments. Its versatility and widespread use underscore its significance in the chemical industry.
|
|
|
|
Chemical Formula |
C4H4O4 |
|
Exact Mass |
116.01 |
|
Molecular Weight |
116.07 |
|
m/z |
116.01 (100.0%), 117.01 (4.3%) |
|
Elemental Analysis |
C, 41.39; H, 3.47; O, 55.13 |
One of the primary applications of maleic acid powder is in the manufacture of polymaleic acid, a polymer extensively utilized in water treatment due to its excellent scale and corrosion inhibition properties. It also serves as a precursor for the synthesis of unsaturated polyester resins, which find uses in the production of fiberglass-reinforced plastics, coatings, and adhesives.
in Polyamide Resins
Polyamide resin, also known as nylon resin, is a type of high-molecular-weight polymer containing repeated amide groups in its macromolecular chain. It can be produced through the polycondensation of diamines and dibasic acids or by the polymerization of a single lactam molecule. This versatile plastic material boasts excellent properties and is widely used. It is categorized into non-reactive (neutral) and reactive polyamides, with applications ranging from inks, hot-melt adhesives, and coatings to epoxy resin hardeners, binders, linings, and encapsulation/molding resins. Neutral polyamides are particularly suited for printing on plastic films, while reactive polyamides excel as epoxy resin curing agents, imparting superior adhesion, flexibility, and chemical resistance.
While itself is not directly used to synthesize polyamide resins, its derivatives and copolymers can play a role in modifying or enhancing the properties of polyamide resins. Polyamide resins are a versatile class of polymers known for their excellent mechanical properties, chemical resistance, and thermal stability. The incorporation of maleic acid derivatives can further tailor these properties to meet specific application requirements.
However, it's worth noting that the direct use in polyamide resin synthesis is uncommon. Instead, researchers and manufacturers often focus on the development of copolymers or grafted polymers that contain the moieties, which can then be used to modify polyamide resins through blending or chemical reactions.
in Amide-Anhydride Copolymers
Amide-anhydride copolymers are a class of advanced polymers characterized by the integration of amide (–CONH–) and anhydride (–CO–O–CO–) linkages within their molecular structure. These copolymers exhibit unique properties stemming from the synergistic effects of both constituent units. The amide groups contribute to enhanced thermal stability, mechanical strength, and resistance to hydrolysis, while the anhydride groups introduce reactivity and the potential for cross-linking, which can further tailor material properties. Amide-anhydride copolymers find applications in diverse fields such as biomedical engineering, where their biodegradability and biocompatibility are advantageous, as well as in advanced coatings, adhesives, and membranes due to their robust performance under harsh conditions. Their tunable properties make them versatile materials for innovative solutions across multiple industries.
Maleic acid is more directly involved in the synthesis of amide-anhydride copolymers. These copolymers are typically obtained by copolymerizing it (or its anhydride form) with various amides, such as those derived from amino acids or aliphatic diamines. The resulting copolymers inherit the properties of both amide and anhydride moieties, leading to materials with unique combinations of properties.
Properties and Applications
Enhanced Adhesion
Amide-anhydride copolymers often exhibit improved adhesion to various substrates, including metals, polyolefins, and other polymers. This makes them ideal for use as adhesives, coatings, and compatibilizers in multilayer structures.
Thermal Stability
The anhydride moiety in these copolymers contributes to their thermal stability, making them suitable for applications where high-temperature performance is required.
Chemical Resistance
The copolymers also offer good chemical resistance, making them resistant to a wide range of chemicals, including acids, bases, and solvents.
The manufacturing of amide-anhydride copolymers typically involves copolymerization reactions. These reactions can be carried out in various solvents and under different reaction conditions, depending on the specific amide and anhydride monomers used. The copolymerization process can be controlled to achieve the desired copolymer composition and molecular weight.
In some cases, grafting reactions can also be employed to introduce the moieties onto the backbone of existing polymers, such as polyolefins or polyamides. This grafting process can be achieved through radical initiation, catalytic reactions, or other methods, depending on the specific polymer and reaction conditions.
With the rapid development of society and the extensive application of petrochemical products, non renewable petrochemical resources have become increasingly strained. Using new technologies and processes to develop new renewable resources to replace non renewable petrochemical resources has become an urgent problem to be solved. Biomass resource is a kind of green renewable resource with abundant reserves and huge potential utilization value. The development and utilization of biomass resources gradually replace the use of petrochemical resources, which has become the main energy strategy of most countries.
Maleic acid powder is an important raw material in many fields of the chemical industry. As one of the 12 important chemical raw materials listed by the U.S. Energy Agency in the future, it has been widely used in resins, pharmaceuticals, plasticizers, copolymers and agricultural chemicals, and can also be used as an intermediate of other chemical products.
At present, maleic acid powder is mainly produced by hydrolysis of maleic anhydride, a fossil fuel. Maleic anhydride is mainly obtained by oxidation of benzene, butane or butene, which is heavily dependent on traditional fossil resources. Therefore, the production from maleic anhydride not only increases the pressure on the environment, but also further worsens the national energy security. Therefore, the synthesis from renewable biomass resources or biomass platform compounds can not only reduce the dependence on traditional fossil energy, but also improve the natural environment, which has great attraction.
Industrial Applications
► Organic Synthesis
Maleic acid serves as a versatile intermediate in organic synthesis, participating in numerous reactions such as esterification, amidation, and Diels-Alder cycloadditions. Its derivatives, including maleic anhydride and maleates, are widely used in the production of unsaturated polyester resins, which are essential components of fiberglass-reinforced plastics, coatings, and adhesives. Maleic anhydride is also a key precursor for the synthesis of glyoxylic acid via ozonolysis, a reaction with applications in the pharmaceutical and agrochemical industries.
► Pharmaceutical Industry
In the pharmaceutical sector, maleic acid plays a crucial role in the formulation of various drugs. It is commonly used as an acidifying agent to adjust the pH of pharmaceutical solutions, ensuring stability and bioavailability. Additionally, maleic acid forms salts with basic drugs, enhancing their solubility and absorption. For instance, maleic acid is combined with chlorpheniramine to form maleic acid chlorpheniramine, an antihistamine used to treat allergic reactions. Similarly, maleic acid nonylamine is utilized as an antiemetic agent.
► Food Industry
Although maleic acid itself is not approved as a food additive, its anhydride form, maleic anhydride, is permitted for limited use in food packaging materials in the United States and the European Union. Maleic anhydride can react with alcohols to form maleates, which are used as emulsifiers and stabilizers in processed foods. However, concerns have been raised regarding the potential migration of maleic anhydride residues into food products, prompting strict regulatory oversight.
► Agricultural Sector
Maleic acid finds applications in agriculture as a herbicide and plant growth regulator. Its ability to inhibit the activity of certain enzymes involved in amino acid metabolism disrupts the growth of weeds and unwanted plants. Maleic acid is also used in the synthesis of agrochemicals, such as fungicides and insecticides, contributing to crop protection and yield enhancement.
► Dental Applications
Research has explored the use of maleic acid in dentistry as an alternative to phosphoric acid for etching tooth enamel prior to bonding orthodontic brackets. Studies suggest that 10% maleic acid can produce similar bond strengths to 37% phosphoric acid while potentially reducing mineral loss from the enamel surface. However, the widespread adoption of maleic acid in dental practice remains limited due to concerns over its long-term effects on tooth structure.
Future Perspectives
The demand for maleic acid is expected to grow in the coming years, driven by its expanding applications in emerging industries such as renewable energy and biodegradable materials. Research efforts are focused on developing greener synthesis methods for maleic acid, utilizing bio-based feedstocks and catalytic systems with reduced environmental impact. Additionally, the exploration of novel derivatives and functionalized maleic acid compounds holds promise for the creation of advanced materials with tailored properties.
adverse reaction
Maleic acid, with the chemical formula C ₄ H ₄ O ₄, is a white crystalline powder with a weak sour taste and pungent odor. As an important organic acid, maleic acid has wide applications in industry, food, medicine and other fields, such as in the production of unsaturated polyester resins, pesticides, dyes, food additives, etc. However, maleic acid powder may cause various adverse reactions to the human body during use, involving multiple organ systems such as the skin, eyes, respiratory tract, and digestive system. In severe cases, it may even endanger life.
Acute toxicity
Maleic acid powder has a certain degree of acute toxicity, and its toxic effects are mainly produced through oral administration, skin contact, and inhalation. Different animal experiments have shown species differences in the acute toxicity of maleic acid, but all indicate its potential harm.
Oral toxicity
The median lethal dose (LD ₅₀) of maleic acid taken orally in rats is 708mg/kg, and in mice it is 2400mg/kg. This means that for rats, ingestion of approximately 708mg/kg body weight of maleic acid can lead to the death of half of the experimental animals. In practical operation, if malic acid powder is accidentally ingested, especially in large quantities, it may cause serious toxic reactions, including vomiting, abdominal pain, diarrhea, difficulty breathing, coma, and even death.
Skin contact toxicity
The LD50 of maleic acid in rabbit skin contact is 1560mg/kg. This indicates that maleic acid has a strong irritant effect on the skin. When the skin comes into direct contact with high concentrations of maleic acid powder or solution, it may cause redness, swelling, pain, burns, and even ulceration. Long term or repeated exposure may lead to dry skin, cracking, allergies, etc.
Inhalation toxicity
The 1-hour median lethal concentration (LC50) of maleic acid powder or vapor inhaled by rats is 0.72mg/L. Inhaling high concentrations of maleic acid vapor or dust can cause respiratory irritation symptoms such as coughing, wheezing, shortness of breath, pharyngitis, etc. In severe cases, it may lead to chemical pneumonia, pulmonary edema, and even respiratory failure.
Skin irritation and allergic reactions
Maleic acid powder has significant irritation and sensitization to the skin, and can cause various skin adverse reactions.
Irritation reaction
After direct contact with maleic acid powder or solution on the skin, a sharp and burning sensation may immediately occur, followed by acute irritant dermatitis symptoms such as erythema, edema, and blisters. These symptoms usually appear within minutes to hours after exposure, and the severity is proportional to the concentration and duration of exposure.
Allergic reactions
Some individuals may experience allergic reactions to maleic acid, manifested as contact dermatitis. Allergic reactions usually occur after repeated exposure, and symptoms include skin itching, erythema, papules, blisters, etc. In severe cases, severe skin damage such as bullous epidermal lysis may occur. People with allergies should be particularly cautious when using maleic acid related products.
Chronic skin damage
Long term or repeated exposure to maleic acid powder may lead to chronic skin damage, such as dryness, cracking, hyperkeratosis, etc. These damages may increase the risk of skin infections and affect the normal function of the skin.
Frequently Asked Questions
What does maleic acid do for hair?
+
-
Maleic acid is a small organic compound used in haircare formulations to strengthen internal hair bonds, smooth the cuticle, and prevent breakage.
What is the pH of maleic acid?
+
-
Maleic Acid (1 M, pH 7.5) Preparation and Recipe | AAT Bioquest. Maleic acid buffer is commonly used for Southern blot preparation and as a washing buffer in numerous applications involving nucleic acids. It has a shelf life of 6 months to a year.
Which fruit has maleic acid?
+
-
Malic acid is the main acid in many fruits, including apricots, blackberries, blueberries, cherries, grapes, mirabelles, peaches, pears, plums, and quince, and is present in lower concentrations in other fruits, such as citrus. It contributes to the sourness of unripe apples.
Hot Tags: maleic acid powder cas 110-16-7, suppliers, manufacturers, factory, wholesale, buy, price, bulk, for sale, s allyl l cysteine, 5 hydroxymethylfurfural synthesis, Hinokitiol powder, Pamoic acid, spermidine powder