Diethyl phthalate Diethyl phthalate

Structural formula

• Numbering system
• Physical property data
• Toxicological data
• Ecological data
• Molecular structure data
• Computing chemical data
• More
  • Properties and Stability
  • Storage method
  • Synthesis method
  • Purpose

Numbering system

CAS number:84-66-2

MDL number:MFCD00009111

EINECS number:201-550-6

RTECS number:TI1050000

BRN number:1912500

PubChem ID:None

Physical property data

1. Properties: colorless, odorless, transparent, slightly aromatic liquid.

2. Relative density (g/mL, 25/4℃): 1.1160

3. Relative density (20℃, 4℃): 1.232

4. Melting point (ºC): -40.5

5. Boiling point (ºC, normal pressure): 295~299

6. Boiling point (ºC, 1.6KPa): 172

7. Refractive index (25ºC): 1.502

8. Flash point (ºC, closed): 117

9. Flash point (ºC, open): 140

10. Autoignition point or ignition temperature (ºC): 155

11. Vapor pressure (kPa, 163ºC): 1.867

12. Viscosity (mPa· s, 25ºC): 10.06

13. Heat of evaporation (KJ/mol): 67.0

14. Freezing point (ºC): -40

15. Normal temperature Refractive index (n²⁰): 1.5022

16. Conductivity (S/m, 25ºC): 1.1×10^-9

17. Gas phase standard combustion heat (enthalpy) (kJ·mol^-1): -6034.6

18. Gas phase standard claimed heat (enthalpy) (kJ·mol^-1): -688.4

19. Solubility: Insoluble in water, soluble in ethanol, ether, acetone and other organic solvents.

20. Liquid phase standard combustion heat (enthalpy) (kJ·mol^-1): -5946.3

21. Liquid phase standard claimed heat (enthalpy) )( kJ·mol^-1): -776.6

22. Liquid phase standard hot melt (J·mol^-1·K ^-1): 375.0

Toxicological data

Diethyl phthalate irritates mucous membranes, but its acute and chronic toxicity is very low, and it does not have any obvious irritating or allergic effects on the skin. The maximum allowable concentration in the air is 5 mg/m3. This product has low toxicity. The oral LD50 of rabbits is 1000 mg/kg.

Ecological data

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Molecular structure data

1. Molar refractive index: 59.06

2. Molar volume (cm³/mol): 198.2

3. Isotonic specific volume (90.2K): 496.5

4. Surface tension (dyne/cm): 39.3

5. Polarizability (10^-24cm³): 23.41

Compute chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): None

2. Number of hydrogen bond donors: 0

3. Number of hydrogen bond acceptors: 4

4. Number of rotatable chemical bonds: 6

5. Number of tautomers: none

6. Topological molecule polar surface area 52.6

7. Number of heavy atoms: 16

8. Surface charge: 0

9. Complexity: 223

10. Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 0

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Properties and stability

1. Miscible with ethanol, ether, acetone, and benzene organic solvents, but insoluble in water. Chlorinated rubber, rosin, nitrocellulose, benzyl abietate, coumarone resin, glycerol trirosinate, polystyrene, polymethyl methacrylate, polyvinyl acetate, ethyl cellulose, vinyl chloride Vinyl acetate copolymer, etc. have good solubility. But cellulose acetate is not very soluble. Combustible. In case of fire, use foam fire extinguishing agent, carbon dioxide or carbon tetrachloride to extinguish the fire.

2. Chemical properties: Diethyl phthalate is boiled in a carbon dioxide atmosphere for 8 hours and decomposes into ethylene, ethanol, phthalic anhydride, monoethyl phthalate, etc. It has no reaction when placed with water at room temperature. It generates o-toluic acid, phthalic acid and a small amount of benzoic acid, methane, carbon dioxide, etc. at 250~325℃ and 10MPa. In sodium hydroxide alcohol solution, when hydrolyzed at 25°C, 10% will be hydrolyzed in 5 minutes, 30% will be hydrolyzed in 25 minutes, and 60% will be hydrolyzed in 4 hours.

3. Diethyl phthalate reacts with a methanol solution of ammonia to form phthalamide. It reacts with urea and sodium ethoxide in boiling alcohol to form phthalimide. Reacts with phenylmagnesium bromide to form 10,10-diphenylanthrone. When heated together with ethylene glycol in a vacuum, the reaction starts above 190°C and generates a polymer of ethylene glycol phthalate at 300°C.

4. Diethyl phthalate and metal salt form crystalline molecular compounds. For example, it forms a crystal with a melting point of 104°C with tin tetrachloride, which is easily hydrolyzed.

5. Exists in flue-cured tobacco leaves, burley tobacco leaves and smoke.

6. Irritate mucous membranes and cause anesthesia at high concentrations.

Storage method

Stored in a cool, dry warehouse. Keep away from sources of fire and strong oxidants. Severe impacts should be prevented during transportation.

Synthesis method

1. Use phthalic anhydride and ethanol as raw materials, excess ethanol as a water-carrying agent, and perform esterification at the ethanol reflux temperature. The crude ester is neutralized, washed, and distilled to obtain the finished product.

2. Add phthalic anhydride and excess ethanol to the reaction pot, then add concentrated sulfuric acid as a catalyst, and reflux with water. The crude ester obtained is neutralized, washed, and distilled to obtain the finished product. Each ton of product consumes 760kg of phthalic anhydride and 700kg of ethanol. The technical process can be referred to dioctyl phthalate.

3.In a round-bottomed flask equipped with a water flow condensation reflux device with a water separator, add the solid acid catalyst ferric chloride, phthalic anhydride and Ethanol [like (phthalic anhydride): like (ethanol) = 1:1.5], and then add the water-carrying agent cyclohexane. Heat to reflux and react for about 1.5 hours. Stop the reaction when the volume of the water layer in the water separator no longer increases. After cooling, move the reactant to a distillation flask, first evaporate cyclohexane under normal pressure, and then distill under reduced pressure to collect the 156°C/1.41kPa colorless liquid fraction, which is the finished product. The esterification reaction formula is as follows

4. Tobacco: BU, 14; FC, 40.

Purpose

1. Used as plasticizer, solvent, lubricant, fixative, foaming agent for non-ferrous or rare metal mine flotation, gas chromatography stationary solution, alcohol denaturant, and spray insecticide. This product is compatible with cellulose acetate, cellulose acetate butyrate, polyvinyl acetate, nitrocellulose, ethylcellulose, polymethyl methacrylate, polystyrene, polyvinyl butyral, vinyl chloride-vinyl acetate Most resins such as copolymers have good compatibility. It is mainly used as a plasticizer for cellulose resin, but its high volatility limits its wide application.

2. This product is a plasticizer with strong compatibility. It is compatible with cellulose acetate, nitrocellulose, ethyl cellulose, polyvinyl acetate, polystyrene, and organic glass, and has good film-forming, adhesive and waterproof properties. Better low temperature flexibility and durability than dimethyl phthalate. Together with dimethyl phthalate and used in cellulose acetate, it helps to improve the elasticity and waterproof ability of products. Used in nitrocellulose, products with high strength, good wear resistance and no odor can be obtained. This product is non-toxic and can be used as a plasticizer for non-toxic adhesives in food packaging films. It can also be used as a plasticizer for alkyd resin and nitrile rubber. This product is used in polyvinyl acetate emulsion adhesive to improve adhesion. In cosmetics, it is used as a plasticizer for nail polish.

3.Used as a plasticizer for adhesives, it can improve the adhesion of polyvinyl acetate. Used as a plasticizer for plastics and cellulose resins, its low-temperature softness and durability are better than those of dimethyl phthalate. It is often used together with dimethyl phthalate to improve the water resistance, elasticity and light resistance of products. and hardness. It is also used as a plasticizer for alkyd resin, nitrile rubber and chloroprene rubber. Its main disadvantage is its high volatility, which makes operation difficult. It can also be used as a tackifier for polyvinyl acetate emulsion, a plasticizer for food packaging film adhesives, an alcohol denaturant, a fragrance retention agent for spices, a spray insecticide, a solvent for spices, a stabilizer for rocket propellant, etc. . Used as solvents and lubricants in pharmaceutical manufacturing.

Mixture can improve adhesion. In cosmetics, it is used as a plasticizer for nail polish.

3.Used as a plasticizer for adhesives, it can improve the adhesion of polyvinyl acetate. Used as a plasticizer for plastics and cellulose resins, its low-temperature softness and durability are better than those of dimethyl phthalate. It is often used together with dimethyl phthalate to improve the water resistance, elasticity and light resistance of products. and hardness. It is also used as a plasticizer for alkyd resin, nitrile rubber and chloroprene rubber. Its main disadvantage is its high volatility, which makes operation difficult. It can also be used as a tackifier for polyvinyl acetate emulsion, a plasticizer for food packaging film adhesives, an alcohol denaturant, a fragrance retention agent for spices, a spray insecticide, a solvent for spices, a stabilizer for rocket propellant, etc. . Used as solvents and lubricants in pharmaceutical manufacturing.