Isobutyraldehyde

Product Name:

Isobutyraldehyde

CAS:

78-84-2

MF:

C4H8O

MW:

72.11

EINECS:

201-149-6

Product Categories:

Carbonyl Compounds;Chemical Synthesis;Aldehydes;Building Blocks;C1 to C6;Organic Building Blocks

Mol File:

78-84-2.mol

Melting point 

−65 °C(lit.)

Boiling point 

63 °C(lit.)

density 

0.79 g/mL at 25 °C(lit.)

vapor density 

2.5 (vs air)

vapor pressure 

66 mm Hg ( 4.4 °C)

FEMA 

2220 | ISOBUTYRALDEHYDE

refractive index 

n20/D 1.374(lit.)

Fp 

−40 °F

storage temp. 

2-8°C

solubility 

water: soluble11g/100mL at 20°C(lit.)

form 

Liquid

color 

Clear

Odor

Pungent.

Odor Threshold

0.00035ppm

explosive limit

1.6-11.0%(V)

Water Solubility 

75 g/L (20 ºC)

Sensitive 

Air Sensitive

JECFA Number

252

Merck 

14,5154

BRN 

605330

Stability:

Stable. Refrigerate. Highly flammable. Incompatible with strong oxidizing agents, strong bases, strong acids, strong reducing agents.

CAS DataBase Reference

78-84-2(CAS DataBase Reference)

NIST Chemistry Reference

Propanal, 2-methyl-(78-84-2)

EPA Substance Registry System

Isobutyraldehyde (78-84-2)

Hazard Codes 

F,Xn,Xi

Risk Statements 

11-22-36

Safety Statements 

16-36/37-9-33-29-26

RIDADR 

UN 2045 3/PG 2

WGK Germany 

1

RTECS 

NQ4025000

F 

9-13-23

Autoignition Temperature

384 °F

TSCA 

Yes

HS Code 

2912 19 00

HazardClass 

3

PackingGroup 

II

Hazardous Substances Data

78-84-2(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 3.7 g/kg (Smyth)

Description

Isobutyraldehyde, also known as 2-Methylpropanal, is an organic compound belonging to the family of aldehydes, which can be found in alcoholic beverages, tea, breads, cooked pork, spearmint oil as well as fresh fruits, such as apple, banana, cherry, etc. It is manufactured by the hydroformylation of propene, usually obtained as a side-product. It can be applied as a source for producing other chemicals, including isobutyl alcohol, neopentyl glycol as well as isobutanoic acid production and used to produce amino acids such as valine and leucine. Besides, isobutyraldehyde commonly serves as an intermediate in the field of chemical industry for manufacture of pharmaceuticals (such as Vitamin B5), crop protection products, pesticides, synthetic resins, antioxidants, vulcanisation accelerators, textile auxiliaries, perfumery and flavors.

References

https://pubchem.ncbi.nlm.nih.gov/compound/isobutyraldehyde#section=Top
http://chemindustry.ru/Isobutyraldehyde.php
http://product-finder.basf.com/group/corporate/product-finder/en/brand/ISOBUTYRALDEHYDE
https://en.wikipedia.org/wiki/Isobutyraldehyde

Description

Isobutyraldehyde has a characteristic odor. Synthesized via oxidation of isobutyl alcohol with potassium dichromate and concentrated sulfuric acid.

Chemical Properties

Isobutyraldehyde has a characteristic sharp, pungent odor.

Chemical Properties

colourless liquid with an extremely unpleasant smell

Occurrence

Reported found in apple and currant aromas and in the essential oils from tobacco leaves and tea leaves, also in the essential oils of Pinus jeffreyi Murr. leaves, Citrus aurantium leaves, and Datura stramonium. Reported found in apple, banana, sweet and sour cherry, currants, kohlrabi, carrots, celery, peas, potato, tomato, peppermint, corn mint and spearmint oil, vinegar, wheat and rye breads, cheeses, butter, yogurt, egg, caviar, fatty fish, meats, hop oil, beer, brandy, rum, sherry, cider, whiskies, grape wines, cocoa, coffee, tea, filberts, peanuts, popcorn, oats, soybeans, honey, mushrooms, macadamia nuts, cauliflower, pear and apple brandy, rice, sukiyaki, malt, loquat, clary sage, shrimps, truffle, scallops and squid

Uses

Isobutyraldehyde is used in the synthesisof cellulose esters, resins, and plasticizers;in the preparation of pantothenic acid andvaline; and in flavors.

Uses

In the synthesis of pantothenic acid, valine, leucine, cellulose esters, perfumes, flavors, plasticizers, resins, gasoline additives.

Definition

ChEBI: A member of the class of propanals that is propanal substituted by a methyl group at position 2.

Preparation

By oxidation of isobutyl alcohol with potassium dichromate and concentrated sulfuric acid.

Aroma threshold values

Detection: 0.4 to 43 ppb

General Description

A clear colorless liquid with a pungent odor. Flash point of -40°F. Less dense than water and insoluble in water. Hence floats on water. Vapors are heavier than air. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Oxidizes slowly on exposure to air. Stable (less than 10% decomposition) for four hours when exposed to light and air in a closed system. Stable for two weeks when stored under nitrogen at temperatures up to 77°F. Insoluble in water.

Reactivity Profile

Isobutyraldehyde can react vigorously with reducing agents, with oxidizing agents, strong bases and mineral acids. Can undergo exothermic self-condensation or polymerization reactions that are often catalyzed by acid. Generates flammable and/or toxic gases in combination with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Reacts slowly when exposed to air with air to give peroxides and other products. These reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by their products). The addition of stabilizers (antioxidants) retards autoxidation.

Hazard

Highly flammable, dangerous fire and explosion risk. Irritant to skin and eyes.

Health Hazard

Vapor is irritating to the eyes and mucous membranes.

Health Hazard

Isobutyraldehyde is a moderate skin and eyeirritant; the effect may be slightly greaterthan that of n-butyraldehyde. An amounttotaling 500 mg in 24 hours produced severeskin irritation in rabbits; 100 mg causedmoderate eye irritation.
The toxicity of isobutyraldehyde determinedon test animals was very low. Exposureto 8000 ppm (23,600 mg/m3) for 4 hours waslethal to rats.
LD50 value, oral (rats): 2810 mg/kg.

Fire Hazard

Behavior in Fire: Vapors are heavier than air and may travel considerable distance to a source of ignition and flash back. Fires are difficult to control due to ease of reignition.

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Carcinogenicity

Isobutyraldehyde is not mutagenic in various strains of S. typhimurium and is noncarcinogenic in rats and mice.

Purification Methods

Dry isobutyraldehyde with CaSO4 and use it immediately after distillation under nitrogen because of the great difficulty in preventing oxidation. It can be purified through its acid bisulfite derivative. [Beilstein 1 IV 3262.]

Waste Disposal

Isobutyraldehyde is burned in a chemicalincinerator equipped with an afterburner andscrubber.

Preparation Products

1-Butanol-->2-Methyl-1-propanol-->Isobutyric acid-->Methyl methacrylate-->Butyraldehyde-->2,2-Dimethyl-1,3-propanediol-->Isobutyronitrile-->L-Valine-->3-(4-ISOPROPYLPHENYL)ISOBUTYRALDEHYDE-->3-Methyl-2-butanone-->Rifapentine-->D-(+)-Pantothenic acid calcium salt-->DL-Pantolactone-->ALDICARB-OXIME-->Carbosulfan-->2,5-Dimethyl-2,4-hexadiene-->2-AMINO-3-METHYLBUTANENITRILE-->FENPROPIMORPH-->2-ISOPROPYL-6-METHYL-4-PYRIMIDINOL-->D-(-)-PANTOLACTONE-->Isobutylamine-->3-Hydroxy-2,2-dimethylpropanal-->DL-Valine-->2-Methylbutyl 2-methylbutyrate-->1-CHLORO-2-METHYLPROPYL CHLOROFORMATE-->1-CHLORO-2-METHYL-1-PROPENE-->2,6-Dimethyl-5-heptenal-->N,N''-(isobutylidene)diurea-->GERANYL ISOBUTYRATE-->2,2,4-Trimethyl-1,3-pentanediolmono(2-methylpropanoate)-->5-METHYL-3-HEXEN-2-ONE-->Neopentyl glycol monoester hydropivalicate

Raw materials

CARBON MONOXIDE-->Potassium dichromate-->2-Methyl-1-propanol-->PROPYLENE-->Butyraldehyde-->2-Amino-3-chlorobenzoic acid