What Is Meperidine?

Colorless liquid. It smells like pepper. Miscible with water, soluble in ethanol, ether, acetone and benzene. The boiling point of the 35% piperidine azeotropic solution is 92.8 ° C; pKa11.1; slightly more basic than pyridine. It forms a salt with an acid. Its chemical properties are similar to those of a secondary fatty amine. Can volatilize with steam. Used in pharmaceuticals, mainly piperidine hydrochloride and piperidine nitrate (flaky crystals, melting point 110 ° C). It is also used in other organic synthesis and as a curing agent for epoxy resins. Prepared from pyridine by hydrogenation. Has strong reduction. [1]

Chinese name
Piperidine
English name
Piperidine
Chinese alias
Hexahydropyridine
English alias
Piperidine solution; Piperidine (Controlled Chemical); Hexahydropyridine; Piperidine, 99%; Piperidine, polymer-bound
CAS number
110-89-4
EINECS number
203-813-0
Molecular formula
C 5 H 11 N; (CH 2 ) 5 NH
Molecular weight
85.15
InChI
InChI = 1 / C5H11N / c1-2-4-6-5-3-1 / h6H, 1-5H2
Melting point
-13
density
Relative density (water = 1) 0.86;
Boiling point
106
Flash point
16
Water soluble
Miscible
use
Used as intermediates in synthetic drugs, raw materials for rubber accelerators, epoxy resin curing agents, etc.
Safety term
S16 :;
Appearance and properties: colorless, clear liquid with ammonia-like odor.
Relative vapor density (air = 1): 3.0
Saturated vapor pressure (kPa): 5.33 (29.2 ° C)
Combustion heat (kJ / mol): 3455.2
Solubility: soluble in water, ethanol,
Reactions that generate piperidine:
Reaction to generate piperidine (full)
Reactant
Product
Reaction conditions
references

pyridine

piperidine
Reaction condition 1
Reagent: osmium asbestos
Reaction temperature: 150
Other conditions: Hydrogenation
Reaction condition 2
Other conditions: Electrolysis
Reaction condition 3
Reaction temperature: 250
Other conditions: Hydrogenation.unter Druck
Reaction conditions 4
Reagent: H2SO4
Other conditions: bei der elektrochemischen Reduktion an einer Blei-Kathode
Reaction condition 5
Reaction temperature: 160
Reaction pressure 76000-114000
Other conditions: Hydrogenation.an Nickel auf Traegersubstanzen
Reaction condition 6
Reaction temperature: 130-180
Reaction pressure 30400-45600
Other conditions: Hydrogenation.an Nickel auf Traegersubstanzen
Reaction condition 7
Reaction temperature: 175-225
Reaction pressure 57000
Other conditions: Hydrogenation.an chromhaltigen Nickel-Katalysatoren
Reaction condition 8
Reagent: Raney nickel
Reaction temperature: 200
Reaction pressure 110326.2-220652.3
Other conditions: Hydrogenation
Reaction condition 9
Reagent: palladium
nickel / silica gel
Reaction temperature: 130-150
Other conditions: Hydrogenation
Reaction conditions 1 0
Reagent: H2SO4
water
Other conditions: bei der elektrochemischen Reduktion an einer Blei-Kathode
Reaction conditions 1 1
Reagent: ethanol
sodium
hydrogen
Reaction temperature: 130
Reaction conditions 1 2
Reagent: sodium
ethanol
Reaction conditions 1 3
Reagent: sodium
NH3
ammonium chloride
Reaction temperature: -80--50
Reaction conditions 1 4
Reaction temperature: 180
Reaction pressure 25080
Other conditions: Hydrogenation .an aktivierten Nickel-Spaenen
Reaction conditions 1 5
Reagent: tin
HCl
Reaction conditions 1 6
Reagent: SmI2
Solvent: tetrahydrofuran
H2O
Response time: 8.5 min
Yield: 96%
Research purpose: Mechanism // Product distribution
Other conditions: Ambient temperature // other pyridine derivatives, var. Amt. Of reagents, and time
Reaction conditions 1 7
Reagent: Ni (100)
Solvent: gas
Reaction temperature: 6.9-376.9
Research purpose: Product distribution
Other conditions: other mono and dimethyl substituted derivatives, other products
Reaction conditions 1 8
Reagent: hydrogen
Catalyst: Raney nickel
Solvent: H2O
Reaction temperature: 149.9
Reaction pressure
Yield: 87.4%
Research purpose: Product distribution // Kinetics // Thermodynamic data
Other conditions: effect of further hydrogen pressures, temperatures, $ DE (excit.)
Reaction conditions 1 9
Reagent: H2
Catalyst: Pt black
Solvent: H2O
Reaction temperature: 149.9
Reaction pressure
Yield: 97.9%
Research purpose: Mechanism
Other conditions: various pressure, temperature
Reaction conditions 2 0
Reagent: Hydrogen
Catalyst: Rh on polyacrylic acid
Solvent: methanol
H2O
Reaction temperature: 45
Yield: 100% Chromat.
Research purpose: Product distribution
Other conditions: Atmospheric pressure. Number of molecules of the substrate converted per metal atom per hour (Table 3). Other temperatures. Aq. Isopropanol. Rh on a copolymer of styrene with maleic acid.
Reaction conditions 2 1
Reagent: 2-propanol
Catalyst: Raney nickel
Response time: 12 hour (s)
Yield: 88%
Other conditions: Heating
Reaction conditions 2 2
Reagent: SmI2
Solvent: tetrahydrofuran
H2O
Response time: 8.5 min
Yield: 96%
Other conditions: Ambient temperature
Reaction conditions 2 3
Reagent: H2SO4
water
Other conditions: bei der elektrolytischen Reduktion an einer Blei- oder Quecksilber-Kathode
Reaction conditions 2 4
Reagent: Sm, 20percent aq. HCl
Response time: 10 min
Yield: 94%
Research purpose: Product distribution
Other conditions: Ambient temperature // other substituted pyridines, quinolines and isoquinolines; var. Metals
Reaction conditions 2 5
Reagent: platinum
acetic acid
Other conditions: Hydrogenation
Reaction conditions 2 6
Reagent: platinum
HCl
water
Other conditions: Hydrogenation
Reaction conditions 2 7
Reagent: H2SO4
water
Other conditions: bei der elektrolytischen Reduktion an einer Thallium-Kathode
Reaction conditions 2 8
Reagent: platinum
Other conditions: Hydrogenation
Reaction conditions 2 9
Reagent: palladium asbestos
Reaction temperature: 150
Reaction conditions 3 0
Reagent: iridium asbestos
Reaction temperature: 150
Other conditions: Hydrogenation
[4-53]
Calculated chemical data:
1. Reference value for calculation of hydrophobic parameters (XlogP): 0.8
2,
Flammable liquids
High toxicity
Acute toxicity oral-rat LD50: 400 mg / kg; oral-mouse LD50: 30 mg / kg
Stimulation data Skin-Rabbit 5 mg / 24 hours severe; Eyes-Rabbit 250 g / 24 hours severe
Flammability hazard characteristics Flammable when exposed to fire, high temperature, oxidant; Decomposes toxic oxidizing nitrogen gas when heated
Storage and transportation characteristics: storeroom is ventilated, low temperature and dry; stored separately from oxidants and acids
Fire extinguishing agent dry powder, dry sand, carbon dioxide, foam [3]
Dangerous goods mark T, F
Danger category code 61-10-20 / 21-34-23 / 24-11-52-24-20 / 22
Safety Instructions 53-16-26-36 / 37 / 39-45-27
Dangerous Goods Transport Number UN 3286 3 / PG 2
WGK Germany 3
RTECS number TM3500000
F 3-34
HazardClass 8
PackingGroup I
110-89-4 (Hazardous Substances Data) [3]
1. Edible spices.
2.Used as a condensing agent and solvent in organic synthesis
3.Used as analytical reagent
4. Hexahydropyridine, also known as piperidine, is an intermediate of mepidolium, a plant growth regulator.
5. Piperidine, also known as hexahydropyridine, is an intermediate between the fungicide fenpropidin and the plant growth regulator mepiperium.
6. Piperidine is used in the manufacture of local anesthetics, analgesics, bactericides, wetting agents, epoxy resin curing agents, rubber vulcanization accelerators, etc.
7, used as intermediates in synthetic drugs, raw materials for rubber accelerators and epoxy resin curing agents. [198]
1. Acute toxicity:
Oral LD50 in rats: 50mg / kg; Percutaneous LD50 in rabbits: 320mg / kg; LC50 in mice: 6000mg / m3 / 2H;
2. Medium toxicity, strong irritant to eyes and skin and a booster. Small doses can stimulate sympathetic and parasympathetic ganglia, but large doses can inhibit it. Mistakes can cause weakness, nausea, salivation, dyspnea, muscle paralysis and suffocation. Poisoned animals show nausea, vomiting, salivation, dyspnea, increased heart rate, increased blood pressure, weakness, convulsions, and paralysis. Guinea pigs are skin-skinned and cause severe irritation. Instillation into rabbit eyes produces severe irritation with permanent corneal damage.
3. Acute toxicity
LD50: 400mg / kg (rat oral); 276mg / kg (rabbit percutaneous)
LC50: 6000mg / m 3 (inhaled in mice, 2h)
4.Irritating
Transdermal rabbit: 5mg (24h), severe irritation.
Rabbit eyes: 250g (24h), severe irritation. [199]
1.No data on ecological toxicity
2. Biodegradable MITI-I test, initial concentration of 100ppm, sludge concentration of 30ppm, 26.9% degradation after 2 weeks
3. No information on non-biodegradability [199]
1. Molar refractive index: 26.40
2. Molar volume (cm3 / mol): 102.4
3. Isometric Zhang Rong (90.2K): 233.0
4. Surface tension (dyne / cm): 26.7
5. Polarizability (10-24cm3): 10.46 [199]
1. Chemical properties are alkaline (pK a 11.1), and form salts with hydrochloric acid, hydrobromic acid, etc. Reacts with an acylating agent to form an N-acyl derivative. It reacts with a haloalkane to form an N-alkyl derivative, and further reacts to obtain an ammonium salt. Piperidine can be formed by catalytic oxidation or heating with concentrated sulfuric acid.
2. Stable and stable
3. Incompatibility acids, anhydrides, strong oxidants
4. Polymerization hazards without polymerization [199]
Precautions for storage
Store in a cool, ventilated warehouse. Keep away from fire and heat sources. The storage temperature should not exceed 37 ° C. Keep the container sealed. It should be stored separately from oxidants, acids, and edible chemicals. Use explosion-proof lighting and ventilation facilities. Prohibit the use of spark-prone machinery and tools. The storage area should be equipped with spill emergency treatment equipment and suitable containment materials. [199]
Gas chromatography with reference to the Handbook of Analytical Chemistry (fourth volume, chromatographic analysis), Chemical Industry Press [2]
Maximum allowable concentration of harmful substances in the air of the former Soviet Union workshop 0.2mg / m 3 [pelf] [2]
S16Keep away from sources of ignition.
Keep away from fire.
S26In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
After accidental contact with eyes, rinse immediately with plenty of water and seek medical advice.
S27Take off immediately all contaminated clothing.
Remove your clothing as soon as it becomes contaminated.
S45In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
In case of accident or if you feel unwell, seek medical advice immediately (show the label if possible). [200]
R11Highly flammable.
Highly flammable.
R34Causes burns.
Causes burns. [200]

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