Decalin
Structural formula
| Business number | 0238 |
|---|---|
| Molecular formula | C10H18 |
| Molecular weight | 138.25 |
| label |
Decalin, Bicyclo(4.4.0)decane, Decalin, Bicyclo(4,4,0)decane, Decalin, Solvent for greases and resins, For shoe polish synthesis, paint remover, vapor recovery agent, Lubricant |
Numbering system
CAS number:91-17-8
MDL number:MFCD00004130
EINECS number:202-046-9
RTECS number:QJ3150000
BRN number:878165
PubChem ID:None
Physical property data
1. Properties: colorless liquid with slight menthol smell.
2. Boiling point (ºC, 101.3kPa): 195.815 (cis); 187.310 (trans)
3. Melting point (ºC): -42.98 (cis); – 30.382 (trans form)
4. Relative density (g/mL, 20/4ºC): 0.8967 (cis form); 0.86969 (trans form)
5. Refractive index (20ºC) ): 1.48098 (cis); 1.46932 (trans)
6. Viscosity (mPa·s, 20ºC): 3.381 (cis); 2.128 (trans)
7 .Flash point (ºC): 58 (mixture)
8. Fire point (ºC): 262 (mixture)
9. Heat of vaporization (KJ/mol, 25ºC): 51.38 ( cis form); 49.91 (trans form)
10. Heat of evaporation (KJ/mol, b.p.): 41.026 (cis form); 40.26 (trans form)
11. Heat of fusion (KJ/mol): 9.49 (cis); 14.424 (trans)
12. Heat of formation (KJ/mol, 25ºC): -219.59 (cis); -230.86 (trans)
13. Heat of combustion (KJ/mol, 25ºC): 5896.02 (cis); 5884.75 (trans)
14. Specific heat capacity (KJ/(kg·K), 25ºC, Liquid, constant pressure): 1.68 (cis); 1.65 (trans)
15. Critical temperature (ºC): 429.0 (cis); 413.8 (trans)
16. Critical pressure (MPa): 2.74 (cis); 2.74 (trans)
17. Thermal conductivity (W/(m·K), 62.8ºC, mixture): 107.182×10-3
18. Aniline point (ºC): 35.3 (cis); 35.3 (trans)
19. Lower explosion limit (%, V/ V): 0.7 (cis); 0.4 (trans)
20. Explosion upper limit (%, V/V): 4.9 (cis); 4.9 (trans)
21. Solubility: Insoluble in water. Miscible with various organic solvents such as methanol, ethanol, chloroform, benzene, acetone and esters.
Toxicological data
1. Acute toxicity[1]
LD50: 4170mg/kg (rat oral); 5900mg/kg (rabbit dermal )
LC50: 710ppm (rat inhalation, 4h)
2. Irritation No information available
3 .Subacute and chronic toxicity [2] Guinea pig skin 6cm2, apply this product for 2 days, cause death 10 days after application. Three guinea pigs were exposed to a concentration of 1.8g/m3 for 8 hours a day. One died on the first day, the second died after 21 days, and the third died after 23 days. Pathological changes include pulmonary congestion and liver and kidney damage.
Ecological data
1. Ecotoxicity[3] LC50: 4.3mg/L (48h) (high body yarrow); 1.84mg/L (48h) (green Medaka)
2. Biodegradability [4] MITI-I test, initial concentration 100ppm, sludge concentration 30ppm, degradation 2 after 4 weeks %.
3. Non-biodegradability No data yet
4. Bioaccumulation [5] BCF: 660 (Theory).
Cis isomer:
839~2380 (carp, contact concentration 2.1mg/L, contact time 8 weeks);
1290~2400 ( Carp, contact concentration 0.21mg/L, contact time 8 weeks)
Trans isomer:
1170~3050 (carp, contact concentration 2.8mg/L, contact time 8 weeks);
1300~2510 (carp, exposure concentration 0.28mg/L, exposure time 8 weeks)
Molecular structure data
1. Molar refractive index: 44.16
2. Molar volume (cm3/mol): 158.4
3. Isotonic specific volume (90.2K ): 369.1
4. Surface tension (dyne/cm): 29.4
5. Dielectric constant (F/m): 2.15
6. Polar Chemical rate (10-24cm3): 17.51
Compute chemical data
1. Reference value for hydrophobic parameter calculation (XlogP): 4.6
2. Number of hydrogen bond donors: 0
3. Number of hydrogen bond acceptors: 0
4. Number of rotatable chemical bonds: 0
5. Number of tautomers: none
6. Topological molecule polar surface area 0
7. Number of heavy atoms: 10
8. Surface charge: 0
9. Complexity: 80.6
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. High flash point flammable liquid, non-corrosive to metals, and quick to rubber. Avoid using rubber products in valves and gaskets. Insoluble in water. Miscible with various organic solvents such as methanol, ethanol, chloroform, benzene, acetone and esters. The dissolving capacity is smaller than that of tetralin, and it can dissolve dammar resin, frankincense, oleoresin, alkyd resin, grease, wax and latex, etc. Does not dissolve nitrocellulose, ethylcellulose, cellulose ester, resin and New Zealand soft resin. Liquid sulfur dioxide is insoluble, but gaseous sulfur dioxide can be absorbed by decalin. Vapors of organic compounds such as benzene, ethanol, and ethyl acetate are also soluble in decalin.
2. Decalin has two isomers, cis and trans, which usually exist in mixtures. Oxidation produces peroxide. Phthalic acid is generated by shaking in acidic potassium permanganate aqueous solution for a long time. Using tin vanadate as a catalyst, it is oxidized to phthalic anhydride by air. Relatively stable to acids and alkalis. Trans-decalin is treated with nitric acid to undergo nitration reaction. Sulfonation reaction occurs with fuming sulfuric acid. It reacts with chlorine in the presence of a small amount of iodine to produce monochlorine or polychlorinated decahydronaphthalene.
3. Stability[6] Stable
4. Incompatible substances[7] Strong oxidizing agent
5. Conditions to avoid contact[8] Air, light
6. Hazards of aggregation[9] No aggregation
Storage method
Storage Precautions[10] Store in a cool, ventilated warehouse. The storage temperature should not exceed 37℃. Keep away from fire and heat sources. Keep container tightly sealed. should be kept away from oxidizer, do not store together. Use explosion-proof lighting and ventilation facilities. It is prohibited to use mechanical equipment and tools that are prone to sparks. The storage area should be equipped with emergency release equipment and suitable containment materials.
Synthesis method
In industry, an equal mixture of two isomers is obtained by catalytic hydrogenation of naphthalene in the presence of a nickel catalyst. If a purer isomer is required, industrial grade decalin can be washed with concentrated sulfuric acid until the acid layer is colorless. Then wash with alkali and water, separate the water layer, and dry with a desiccant. Under reduced pressure distillation, in a tower with 130 theoretical plates, the reflux ratio is close to 145:1, and the cis isomer with a purity of 99.93% (weight) can be obtained; in a tower with 200 theoretical plates, the reflux ratio The ratio is 160:1, and the trans isomer with a purity of 99.97% can be obtained.
Purpose
1. Used as solvent, paint remover and lubricant for oil, grease, resin, rubber, etc. [11]
