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Paraldehyde

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Paraldehyde Basic information

Product Name:
Paraldehyde
Synonyms:
  • FEMA 2003
  • ETHYL ALDEHYDE
  • ACETALDEHYDE TRIMER
  • ACETIC ALDEHYDE
  • ALDEHYDE C2
  • ALDEFRESH
  • ALDEHYDE
  • 2,4,6-TRIMETHYL-1,3,5-TRIOXANE
CAS:
123-63-7
MF:
C6H12O3
MW:
132.16
EINECS:
204-639-8
Product Categories:
  • Aldehydes
  • Bioactive Small Molecules
  • Building Blocks
  • C1 to C6
  • Carbonyl Compounds
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Chemical Synthesis
  • Neurobiology
  • Neuroscience
  • Organic Building Blocks
  • P
  • Pharmacologicals
  • Sedative/Hypnotics
  • Intermediates
  • Organics
  • Aldehyde
  • Organoborons
  • Pyridine
  • Organohalides
  • Quinoline
  • Benzothiophene
  • K00001
Mol File:
123-63-7.mol
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Paraldehyde Chemical Properties

Melting point:
12 °C
Boiling point:
65-82 °C
Density 
0.994 g/mL at 20 °C (lit.)
vapor density 
1.52 (vs air)
vapor pressure 
25.89 psi ( 55 °C)
refractive index 
n20/D 1.39
FEMA 
4010 | PARALDEHYDE
Flash point:
30 °F
storage temp. 
2-8°C
solubility 
120g/l
pka
16(at 25℃)
form 
solution
color 
Colorless liquid
Specific Gravity
0.994
Odor
disagreeable taste, aromatic odor
explosive limit
1.3-17.0%(V)
Water Solubility 
125 g/L (25 ºC)
Merck 
13,7098
BRN 
80142
Dielectric constant
14.5(20℃)
Stability:
Stable. Flammable. Incompatible with strong oxidizing agents, mineral acids.
InChIKey
SQYNKIJPMDEDEG-UHFFFAOYSA-N
LogP
0.670
CAS DataBase Reference
123-63-7(CAS DataBase Reference)
NIST Chemistry Reference
Paraldehyde(123-63-7)
EPA Substance Registry System
Paraldehyde (123-63-7)
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Safety Information

Hazard Codes 
F
Risk Statements 
11-R11-10
Safety Statements 
9-16-29-33-S9-S33-S29-S16
RIDADR 
UN 1993 3/PG 2
WGK Germany 
1
RTECS 
YK0525000
Autoignition Temperature
235 °C
HazardClass 
3.2
PackingGroup 
III
HS Code 
29125000
Hazardous Substances Data
123-63-7(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 1.65 g/kg (Figot)

MSDS

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Paraldehyde Usage And Synthesis

Description

Paraldehyde was first synthesized in 1829 by Wildenbusch and introduced into clinical practice in the United Kingdom by the Italian physician Vincenzo Cervello in 1882. Paraldehyde, a polymer of acetaldehyde, is a clear colorless or slightly yellow transparent liquid with a strong aromatic as well as a disagreeable taste that at low temperatures, it solidifies into a crystalline mass. This agent decomposes with strong into toxic products that may be released into water, soil, or atmosphere.

Chemical Properties

Paraldehyde has a characteristic aromatic odor and warm, but disagreeable burning taste.

Chemical Properties

Paraldehyde is a colourless to yellowish clear liquid. Pleasant, sweet odor. Less dense than water. Vapors are heavier than air.

Uses

Paraldehyde is used in ethanol hangover prevention. It is also used in the treatment of rectal diseases in patients with delirium tremens.

Uses

Paraldehyde is used as solvent for fats, oils, waxes, rubber and resins; as substitute for acetaldehyde; as intermediate for organic chemicals, dyestuffs, accelerators for vulcanizations, rubber oxidants, etc. Product Data Sheet

Uses

Reactant involved in:• ;Modified Sanford reaction1• ;Synthesis of N-arylbenzoquinaldinium derivatives with antimicrobial activity2• ;Hydroformylation of alkenylamines3• ;Studies of molecules with inhibitory activity against HIV-1 integrase4• ;Irregular Wittig reactions for the formation of α-hydroxyketones5

Uses

manufacture of organic compounds.

Preparation

Prepared by the polymerization of acetaldehyde catalyzed by hydrochloric acid and sulfuric acid at medium to high temperatures.

Definition

ChEBI: Paraldehyde is a trioxane that is 1,3,5-trioxane substituted by methyl groups at positions 2, 4 and 6. It has a role as a sedative.

brand name

Paral (Forest).

Aroma threshold values

Recognition at 0.02 to 0.025 mg/m3 (air).

General Description

Paraldehyde is recognizable as the cyclictrimer of acetaldehyde. It is a liquid with a strong characteristicodor detectable in the expired air and an unpleasanttaste. These properties limit its use almost exclusively toan institutional setting (e.g., in the treatment of deliriumtremens). In the past, when containers were opened and airadmitted and then reclosed and allowed to stand, fatalitiesoccurred because of oxidation of paraldehyde to glacialacetic acid.

Air & Water Reactions

Highly flammable. Slightly soluble in water. Decomposed by light and air, on prolonged storage, to acetaldehyde and acetic acid.

Reactivity Profile

Paraldehyde is an aldehyde. Paraldehyde is decomposed by light and air, on prolonged storage, to acetaldehyde and acetic acid. Incompatible with alkalis, hydrocyanic acid iodides and oxidizers.

Health Hazard

INHALATION AND INGESTION: Irritation, headache, bronchitis, pulmonary edema. Irritating to digestive tract. Hypnotic and analgesic properties. Incoordination and drowsiness, followed by sleep. Larger doses-coma-weak pulse and shallow respiration, cyanosis-death from respiratory paralysis. EYES: irritation-can cause serious injury. SKIN: Dermatitis (skin inflammation).

Safety Profile

A human poison by rectal route. Moderately toxic to humans by intramuscular route. Moderately toxic experimentally by inhalation, ingestion, intraperitoneal, and subcutaneous routes. Human systemic effects by rectal route: necrotic changes. A skin and severe eye irritant. Low doses produce hypnotic and analgesic effects. Larger doses depress the nervous system with loss of reflexes, coma, and respiratory depression leadmg to respiratory paralysis and death. Chronic effects include weight loss, muscular weakness, and mental fatigue. However, poisoning is rare. A hypnotic agent. Dangerous fire hazard when exposed to heat, flame, or oxidzers. Slight explosion hazard when exposed to heat or flame. Dangerous; keep away from heat and open flame. To fight fire, use alcohol foam, CO2, dry chemical. Potentially violent reaction with nitric acid. Incompatible with alkahes, hydrocyanic acid, iodides, oxidzers. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES

Synthesis

Paraldehyde, 2,4,6-trimethyl-1,3,5-trioxane (4.3.2), is a trimeric acetaldehyde which is synthesized by the acid-catalyzed polymerization of acetaldehyde and at moderate and high temperatures [32,33].

Potential Exposure

Paraldehyde is used primarily in medicine. It is used as a hypnotic agent, in delirium tremens; and in treatment of psychiatric states characterized by excitement when drugs must be given over a long period of time. It also is administered for intractable pain which does not respond to opiates and for basal and obstetrical anesthesia. It is effective against experimentally induced convulsions and has been used in emergency therapy of tetanus, eclampsia, status epilepticus; and poisoning by convulsant drugs. Since it is used primarily in medicine, the chance of accidental human exposure or environmental contamination is low. However, paraldehyde decomposes to acetaldehyde and acetic acid; these compounds have been found to be toxic. In this case, occupational exposure or environmental contamination is possible. Since paraldehyde is prepared from acetaldehyde by polymerization in the presence of an acid catalyst, there exists a potential for adverse effects, although none have been reported in the available literature. It is also used in the manufacture of organic compounds.

Environmental Fate

Paraldehyde is used in resin manufacture, as a preservative, and in other processes as a solvent. Paraldehyde may enter to the environment via industrial effluents or hospital wastes. Acetaldehyde and acetic acid are two products of degradation of paraldehyde. This compound and its degradation products may be released into water, soil, or atmosphere and then they may be removed from the atmosphere by precipitation.

Shipping

UN1264 Paraldehyde, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Wash paraldehyde with water and fractionally distil it. Alternatively, it is purified by drying with anhydrous Na2SO4, then cooled to 5o, and the frozen material is separated by decantation. The solid is distilled (b 121-124o/atm), the distillate is collected, stored over anhydrous Na2SO4 for several days and re-distilled at atmospheric pressure before use [Le Fevre et al. J Chem Soc 290 1950]. The 2r,4c,6t-trimethyl-1,3,5-trioxane has m 14.5o, b 125o/760mm. [Beilstein 19 II 394, 19 III/IV 4715. 19/9 V 112.]

Incompatibilities

Vapor or liquid may form explosive mixture with air. Incompatible with strong oxidants, strong acids; alkalis, ammonia, amines, iodides, hydrocyanic acid. Violent reaction with liquid oxygen. Contact with acids form acetaldehyde. Attacks rubber and plastics.

Waste Disposal

Incineration in added solvent. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

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