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Product Name | 3-Phenylacrylic acid |
Cas Number | 538-51-2 |
Formula | C9H8O2 |
Molar Mass | 148.16 g/mol |
Density | 1.247 g/cm³ |
Melting Point | 171-175 °C |
Boiling Point | 279 °C |
Solubility In Water | Slightly soluble |
Appearance | White crystalline powder |
Pka | 4.23 |
Refractive Index | 1.586 |
Flash Point | 104 °C |
Vapor Pressure | 0.0098 mmHg at 25 °C |
Logp | 1.96 |
Stability | Stable under recommended storage conditions |
What are the applications of 3-Phenylacrylic acid?
3 - Phenylacrylic acid, also known as cinnamic acid, has a wide range of applications in various fields.3 - Cinnamic acid (also known as phenylacrylic) has many applications in different fields.
In the food industry, it is used as a flavoring agent.In the food industry it is used to flavor foods. Its pleasant, spicy - sweet aroma contributes to enhancing the flavor profiles of many products.Its pleasant, spicy-sweet aroma enhances the flavor profiles of a wide range of products. For example, it can be added to beverages, baked goods, and confectionery items to provide a unique and appealing taste.It can be added to baked goods, confectionery, and beverages to give them a unique taste. Cinnamic acid's natural origin and characteristic flavor make it a popular choice for creating natural - tasting food products.Cinnamic Acid's natural origin, characteristic flavor and unique taste make it a popular ingredient for natural-tasting food products.
The cosmetic and personal care industry also benefits from 3 - phenylacrylic acid.3 - Phenylacrylic Acid is also beneficial to the cosmetic and personal care industries. It has antioxidant properties, which can help protect the skin from damage caused by free radicals.It is rich in antioxidants, which protect skin from free radical damage. Free radicals are unstable molecules that can lead to premature aging, wrinkles, and other skin problems.Free radicals are unstable molecules which can cause premature aging, wrinkles and other skin problems. By neutralizing these free radicals, cinnamic acid can contribute to maintaining healthy - looking skin.Cinnamic acid helps maintain healthy-looking skin by neutralizing free radicals. It may be incorporated into skin creams, lotions, and serums.It can be added to skin creams and lotions. Additionally, its antibacterial properties can be useful in preventing the growth of harmful bacteria on the skin, which is beneficial for maintaining skin hygiene.Its antibacterial properties are also useful in preventing harmful bacteria from growing on the skin. This is good for maintaining skin hygiene.
In the pharmaceutical industry, 3 - phenylacrylic acid has potential medicinal applications.3 - Phenylacrylic Acid has potential medicinal uses in the pharmaceutical industry. It has been studied for its anti - inflammatory properties.Its anti-inflammatory properties have been studied. Inflammation is a key factor in many diseases, including arthritis and some cardiovascular diseases.Inflammation plays a major role in many diseases including arthritis and certain cardiovascular diseases. Compounds with anti - inflammatory effects like cinnamic acid may help in developing drugs to treat these conditions.Cinnamic acid and other compounds with anti-inflammatory properties may be useful in the development of drugs to treat these conditions. Some research also indicates its possible role in anti - cancer activities.Some research indicates that it may also play a role in anti-cancer activities. It may interfere with the growth and spread of cancer cells through various mechanisms, although more in - depth research is still needed in this area.It may interfere with cancer cell growth and spread through different mechanisms. However, more in-depth research is needed in this field.
In the field of polymer synthesis, 3 - phenylacrylic acid can be used as a monomer.In the field polymer synthesis 3 - phenylacrylic can be used as monomer. It can be polymerized to form materials with specific properties.It can be polymerized into materials with specific properties. These polymers may have applications in coatings, adhesives, and plastics.These polymers can be used in plastics, adhesives and coatings. The phenyl group in cinnamic acid can impart certain chemical and physical properties to the resulting polymers, such as improved mechanical strength, heat resistance, and solubility characteristics.The phenyl groups in cinnamic acids can impart certain chemical properties and physical characteristics to the resulting materials, such as improved mechanical strengths, heat resistance and solubility.
Finally, in the fragrance industry, cinnamic acid is a valuable ingredient.Cinnamic acid, as a final ingredient, is highly valued in the fragrance industry. Its strong and distinct aroma is used in the formulation of perfumes, colognes, and air fresheners.Its strong and distinct scent is used to formulate perfumes, air fresheners, and colognes. It can be combined with other fragrant compounds to create complex and long - lasting scents, adding a warm, spicy note to the fragrance compositions.It can be mixed with other aromatic compounds to create complex, long-lasting scents. It adds a warm, spice note to fragrance compositions.
How is 3-Phenylacrylic acid synthesized?
3 - Phenylacrylic acid, also known as cinnamic acid, can be synthesized through several methods.Three different methods are available to synthesize phenylacrylic, also known by the name cinnamic. One common approach is the Perkin reaction.Perkin reaction is a common method.
In the Perkin reaction, benzaldehyde reacts with acetic anhydride in the presence of a base, typically sodium acetate.In the Perkin Reaction, benzaldehyde and acetic anhydride react in the presence a base. This is usually sodium acetate. The reaction mechanism involves several steps.The reaction involves several steps. First, the base, sodium acetate, deprotonates acetic anhydride.First, the base sodium acetate deprotonates anhydride acetic. This generates a resonance - stabilized enolate anion.This produces a resonance-stabilized enolate anion. The enolate anion then attacks the carbonyl carbon of benzaldehyde.The enolate anion attacks the carbonyl atom of benzaldehyde. This forms an intermediate alkoxide ion.This produces an intermediate alkoxide. Next, the intermediate undergoes an intramolecular acyl - transfer reaction.The intermediate is then subjected to an intramolecular transfer reaction. This is followed by hydrolysis and decarboxylation steps.Then, the intermediate undergoes hydrolysis and decarboxylation. The hydrolysis step is promoted by the presence of water in the reaction mixture.The presence of water in a reaction mixture promotes the hydrolysis step. The final decarboxylation occurs under the reaction conditions, usually with heating, to yield 3 - phenylacrylic acid.The final decarboxylation takes place under reaction conditions, typically with heating, and yields 3 - phenylacrylic acids.
Another method for the synthesis of 3 - phenylacrylic acid is the Knoevenagel condensation.The Knoevenagel reaction is another method of synthesising 3 - phenylacrylic acids. In this reaction, benzaldehyde reacts with malonic acid in the presence of a basic catalyst, such as pyridine.In this reaction, malonic acid and benzaldehyde are reacting in the presence a basic catalyst such as pyridine. The basic catalyst deprotonates malonic acid, forming a carbanion.The basic catalyst deprotonates the malonic acid to form a carbanion. This carbanion attacks the carbonyl group of benzaldehyde, creating an intermediate.This carbanion attacks benzaldehyde's carbonyl group, creating an intermediary. Through a series of proton - transfer and elimination reactions, the intermediate loses carbon dioxide, resulting in the formation of 3 - phenylacrylic acid.The intermediate loses its carbon dioxide through a series proton-transfer and elimination reactions.
The use of a solid - supported catalyst can also be an efficient way to synthesize 3 - phenylacrylic acid.A solid-supported catalyst can be used to synthesize 3-phenylacrylic acids. For example, some studies have used solid - base catalysts.Some studies have used solid-base catalysts. These catalysts offer advantages such as easy separation from the reaction mixture, recyclability, and potentially higher reaction selectivity.These catalysts have advantages like easy separation from the mixture, recyclability and possibly higher reaction selectivity. The reaction conditions can be optimized to improve the yield and purity of 3 - phenylacrylic acid.The reaction conditions can also be optimized to increase the yield and purity. For instance, controlling the reaction temperature, reaction time, and the molar ratio of reactants is crucial.Controlling the reaction temperature, the reaction time and the molar proportion of reactants are all important. Usually, the reaction temperature for the Perkin reaction is in the range of 150 - 200degC, while for the Knoevenagel condensation, it can be carried out at a relatively lower temperature, often around 80 - 120degC.The reaction temperature of the Perkin reaction usually falls between 150-200degC. However, the Knoevenagel condensate can be carried out in a lower temperature range, typically around 80-120degC. By carefully adjusting these parameters and choosing the appropriate reaction method, a good yield of high - purity 3 - phenylacrylic acid can be obtained.By carefully adjusting the parameters and selecting the appropriate reaction method, it is possible to obtain a high yield of 3 - phenylacrylic acids.
What are the physical and chemical properties of 3-Phenylacrylic acid?
3 - Phenylacrylic acid, also known as cinnamic acid, has the following physical and chemical properties:Phenylacrylic Acid, also known by the name cinnamic acids, has physical and chemical properties as follows:
Physical properties:Physical Properties
Appearance: It usually exists as white to light - yellow needle - like crystals or a crystalline powder.Appearance: It is usually white to light-yellow needle-like crystals or a powder. This form is due to the orderly arrangement of its molecules through intermolecular forces such as hydrogen bonding and van der Waals forces.This is due to an orderly arrangement of the molecules by intermolecular forces, such as hydrogen bonds and van der Waals.
Odor: It has a faint, pleasant balsamic odor.Odor: It emits a pleasant, faint balsamic smell. This odor is characteristic and is often used in the fragrance industry.This odor is a characteristic one and is used often in the fragrance industry.
Melting point: The melting point of 3 - phenylacrylic acid is around 133 - 134 degC.Melting point: 3 - Phenylacrylic Acid melts at 133-134 degrees Celsius. The relatively high melting point is attributed to the strong intermolecular interactions.The strong intermolecular interaction is responsible for the relatively high melting temperature. The planar structure of the phenyl group and the carboxylic acid group allows for efficient packing of molecules in the solid state, resulting in a stable crystal lattice that requires a significant amount of energy to break apart and transition to the liquid state.The planar structure between the carboxylic group and phenyl group allows for efficient packing in the solid state. This results in a crystal lattice which is stable and requires significant energy to transition from the solid to liquid state.
Boiling point: It boils at approximately 300 degC.Boiling point: It boils around 300 degC. The high boiling point further reflects the strength of the intermolecular forces in the liquid state, which must be overcome to convert the substance into the gas phase.The high boiling point reflects the strength intermolecular forces that must be overcome in order to convert the substance from the liquid phase into the gas phase.
Solubility: 3 - phenylacrylic acid is sparingly soluble in water.Solubility: 3 Phenylacrylic Acid is sparingly water soluble. The hydrophobic nature of the phenyl group dominates over the hydrophilic carboxylic acid group, making it less likely to interact favorably with water molecules.The hydrophobic nature dominates the hydrophilic carboxylic group, making it more unlikely to interact favorably. However, it is soluble in many organic solvents such as ethanol, ether, and chloroform.It is soluble in ethanol, chloroform, and ether. The non - polar nature of these organic solvents can better accommodate the non - polar phenyl part of the molecule through van der Waals interactions.These organic solvents are non-polar and can accommodate the non-polar phenyl portion of the molecule better through van der Waals interaction.
Chemical properties:Chemical properties
Acidity: As a carboxylic acid, 3 - phenylacrylic acid exhibits acidic properties.Acidity: 3 - Phenylacrylic Acid is an acidic carboxylic acid. The carboxylic acid group (-COOH) can donate a proton (H+) in an aqueous solution, establishing an equilibrium with its conjugate base, the carboxylate anion.The carboxylic group (-COOH), which is a carboxylic acid, can donate a proton in an aqueous solvent, establishing equilibrium with the carboxylate anion, its conjugate base. The pKa value of cinnamic acid is around 4.44, which indicates that it is a moderately weak acid.Cinnamic acid has a pKa of 4.44 which indicates it is a moderately strong acid. This acidic property allows it to react with bases such as sodium hydroxide (NaOH) to form salts, like sodium cinnamate.This acidic property allows the cinnamic acid to react with bases like sodium hydroxide to form salts such as sodium cinnamate.
Double - bond reactivity: The presence of a carbon - carbon double bond in the molecule imparts reactivity typical of alkenes.Double-bond reactivity: A double carbon-carbon bond in the molecule confers a reactivity characteristic of alkenes. It can undergo addition reactions.It can undergo addition reaction. For example, it can react with bromine (Br2) in an addition reaction across the double bond to form a dibromo - derivative.It can, for example, react with bromine in an addition across the double bond. This reaction is used as a test for the presence of carbon - carbon double bonds.This reaction can be used to test for carbon-carbon double bonds. It can also participate in polymerization reactions under appropriate conditions, where the double bonds break and form long - chain polymers.Under the right conditions, it can also be used in polymerization reactions where double bonds are broken and long-chain polymers are formed.
Esterification: The carboxylic acid group can react with alcohols in the presence of an acid catalyst, such as sulfuric acid, to form esters.Esterification is the reaction of carboxylic acids with alcohols, in the presence an acid catalyst such as sulfuric. This is an important reaction in organic synthesis, as esters of 3 - phenylacrylic acid often have pleasant fragrances and are used in the perfume and flavor industries.This is a very important reaction for organic synthesis. Esters of 3 phenylacrylic acids are often used in the fragrance and flavor industries.
Oxidation: The molecule can be oxidized.Oxidation is the process of oxidizing a molecule. The double bond can be oxidized to form various oxygen - containing functional groups, and the carboxylic acid group can also be further oxidized under more severe conditions.The double bond can be further oxidized in order to form oxygen-containing functional groups. However, the exact oxidation products depend on the oxidizing agent and reaction conditions used.The exact oxidation products are dependent on the oxidizing agents and the reaction conditions.
Is 3-Phenylacrylic acid toxic or harmful to humans and the environment?
3 - Phenylacrylic acid, also known as cinnamic acid, has the following characteristics regarding its impact on humans and the environment:The following characteristics of cinnamic and phenylacrylic acids are related to their impact on humans and the environmental:
Impact on Humans Impact on Humans
1. Toxicity
- In general, 3 - phenylacrylic acid is considered to have low acute toxicity to humans.In general, 3 phenylacrylic acids are considered to be low in acute toxicity for humans. Oral LD50 (lethal dose, 50%) values in animal studies are relatively high.In animal studies, the oral LD50 values (lethal dose at 50%) are relatively high. For example, in rats, the oral LD50 is well above levels that would be typically encountered in normal circumstances.In rats, for example, the oral LD50 levels are well above what would be encountered in normal circumstances. This indicates that a large amount of the substance would need to be ingested to cause death.This means that a large quantity of the substance is required to cause death.
- However, direct contact with concentrated forms of 3 - phenylacrylic acid can cause skin and eye irritation.Direct contact with concentrated forms can cause irritation of the skin and eyes. If it comes into contact with the skin, it may lead to redness, itching, and in more severe cases, dermatitis.It can cause skin irritation, such as redness and itching. In more severe cases, it can lead to dermatitis. In the eyes, it can cause a stinging sensation, watering, and potential damage to the cornea if not promptly washed out.If it gets into the eyes, stinging, watering and possible corneal damage can occur if not washed away immediately.
2. Safety in UseSafety in Use
- It is used in some food products as a flavoring agent and preservative in small amounts.It is used as a flavoring and preservative agent in some food products in small quantities. The US Food and Drug Administration (FDA) has generally recognized it as safe (GRAS) when used in accordance with good manufacturing practices.It is generally considered safe by the US Food and Drug Administration when used according to good manufacturing practices. In the food industry, its use is regulated to ensure that the levels present in food do not pose a risk to human health.In the food industry its use is regulated in order to ensure that levels present in foods do not pose a health risk to humans. It is also used in the cosmetics industry, often in perfumes and skincare products.It is also used by the cosmetics industry in skincare and perfumes. In these applications, proper formulation and dilution are key to preventing any adverse effects on the skin.Proper formulation and dilution is key in these applications to prevent any adverse effects on skin.
Impact on the Environment Impact on the Environment
1. Biodegradability
- 3 - phenylacrylic acid is biodegradable.- 3 phenylacrylic is biodegradable. Microorganisms in the environment, such as bacteria and fungi, can break it down over time.It can be broken down by microorganisms such as bacteria and molds in the environment. This is an important characteristic as it means that when it is released into natural water bodies, soil, or other environmental compartments, it will not persist indefinitely.This is a very important characteristic, as it means it won't persist indefinitely when released into natural water, soil or other environmental compartments. Through a series of biochemical reactions, these microorganisms can convert it into simpler, more environmentally friendly substances such as carbon dioxide, water, and biomass.These microorganisms convert it through a series biochemical reactions into simpler, more eco-friendly substances, such as water, carbon dioxide, and biomass.
2. Ecotoxicity
- While it is biodegradable, 3 - phenylacrylic acid can still have some ecotoxic effects at high concentrations.- Although it is biodegradable phenylacrylic can still have some ecotoxic impacts at high concentrations. For example, in aquatic ecosystems, it may have an impact on fish and other aquatic organisms.In aquatic ecosystems it could have an effect on fish and other organisms. High levels could potentially affect their growth, reproduction, and survival.High levels of this chemical could affect their growth, reproduction and survival. However, in normal environmental conditions where the concentrations are low due to its biodegradability, these ecotoxic effects are likely to be minimal.In normal environmental conditions, where the concentrations of this biodegradable substance are low, ecotoxic effects will likely be minimal. In soil, it may also interact with soil microorganisms and plants.In soil, it can also interact with soil bacteria and plants. But overall, as long as the levels are within the range that can be effectively processed by the natural environment, the impact on the environment is considered to be relatively low.Overall, as long as levels are within a range that is effectively processed by nature, the impact on environment is considered relatively low.
In conclusion, 3 - phenylacrylic acid has low acute toxicity to humans when used properly, and it is biodegradable in the environment, with relatively minor ecotoxic effects at normal environmental levels.Conclusion: 3 - phenylacrylic is a low-acute toxicity chemical for humans when used correctly. It is biodegradable and has relatively minor ecotoxic effects in normal environmental levels. However, precautions should still be taken to avoid direct contact with concentrated forms to prevent skin and eye irritation.To prevent eye and skin irritation, it is important to avoid direct contact with concentrated form.
What are the storage and transportation requirements for 3-Phenylacrylic acid?
3 - Phenylacrylic acid, also known as cinnamic acid, has specific storage and transportation requirements due to its chemical properties.Due to its chemical properties, phenylacrylic, also known by the name cinnamic, acid has specific storage and transport requirements.
Storage Requirements Storage Requirements
1. Container Selection
For storage, it is advisable to use containers made of materials that are resistant to corrosion.It is best to store the chemicals in containers made from materials that resist corrosion. Glass containers are a good option as they do not react with 3 - phenylacrylic acid.Glass containers are an excellent choice as they don't react with 3-phenylacrylic acids. High - density polyethylene (HDPE) containers can also be used, provided they are clean and dry.HDPE containers can be used if they are clean and dried. Avoid using containers that may contain reactive metals such as iron or aluminum, as they could potentially react with the acid over time, leading to contamination or degradation of the product.Avoid using containers containing metals that are reactive, such as aluminum or iron, as these could react with the acid and cause contamination.
2. Storage Environment
The storage area should be cool, dry, and well - ventilated.The storage area must be dry, cool, and well-ventilated. The ideal temperature range for storing 3 - phenylacrylic acid is typically between 2 - 8 degC.The ideal temperature range to store 3 - phenylacrylic is usually between 2 and 8 degC. Higher temperatures can accelerate the rate of any potential chemical reactions or physical changes, such as melting or decomposition.Higher temperatures can speed up any chemical reactions or physical transformations, such as melting and decomposition. Humidity should be kept low to prevent the absorption of moisture, which could affect the purity of the acid.Low humidity is important to prevent moisture absorption, which can affect the purity of acid. A dry environment helps maintain the stability of 3 - phenylacrylic acid.Dry conditions are best for maintaining the stability of 3 phenylacrylic acids. It should be stored away from direct sunlight as ultraviolet light can initiate photochemical reactions that may degrade the compound.It should be kept away from direct sunlight, as ultraviolet light can cause photochemical reactions which may degrade the compound.
3. Separation from Incompatible SubstancesSeparation from Incompatible Substances
3 - phenylacrylic acid should be stored separately from strong oxidizing agents, strong bases, and reactive metals.Store phenylacrylic acids away from strong bases, strong oxidizing agents and reactive metals. Oxidizing agents can react with the acid, potentially leading to combustion or explosion in extreme cases.Oxidizing agents may react with the acid and cause combustion or explosions in extreme cases. Bases will react with the acidic functional group of 3 - phenylacrylic acid, neutralizing it and altering its chemical properties.Bases will react to the acidic functional groups of 3 - Phenylacrylic Acid, neutralizing and altering its chemical property.
Transportation Requirements Transportation Requirements
1. Packaging
During transportation, 3 - phenylacrylic acid must be well - packaged to prevent leakage and damage.The 3 - phenylacrylic acids must be packaged well to prevent leakage or damage during transportation. Inner linings of plastic or other suitable materials can be used inside the outer packaging, which is usually made of sturdy cardboard boxes or wooden crates.In the outer packaging which is typically made of sturdy cardboard boxes and wooden crates, inner linings can be made from plastic or other suitable material. Each package should be labeled clearly with the name of the substance, its chemical properties, and any relevant hazard warnings.Each package should clearly label the name of the substance and its chemical properties as well as any relevant hazards warnings.
2. Regulatory Compliance
Transportation of 3 - phenylacrylic acid needs to comply with local, national, and international regulations.Transport of 3 - Phenylacrylic Acid must comply with local, state, national and international regulations. For example, in international shipping, it must adhere to the guidelines set by the International Maritime Dangerous Goods (IMDG) Code if transported by sea, or the regulations of the International Air Transport Association (IATA) if shipped by air.In international shipping, for example, it must adhere the guidelines set forth by the International Maritime Dangerous Goods Code (IMDG) if transported by ship, or the regulations set forth by the International Air Transport Association(IATA) if transported by air. These regulations ensure the safety of the transportation process and the protection of the environment.These regulations are designed to ensure the safety and protection of the environment during the transportation process.
3. Handling Precautions
Handlers during transportation should be trained to handle chemicals safely.Transporters should be trained in the safe handling of chemicals. They should wear appropriate personal protective equipment, such as gloves, safety glasses, and protective clothing.Wear protective clothing, gloves, safety glasses and other protective equipment. In case of any spill during transportation, immediate steps should be taken to contain and clean it up according to the proper procedures to prevent any environmental contamination or harm to human health.If there is a spillage during transport, it should be cleaned up immediately and contained according to the correct procedures. This will prevent any contamination of the environment or harm to human safety.