N-Butyric Acid

Product Name:

N-butyric acid

CAS:

107-92-6

MF:

C4H8O2

MW:

88.11

EINECS:

203-532-3

Mol File:

107-92-6.mol

Melting point 

−6-−3 °C(lit.)

Boiling point 

162 °C(lit.)

density 

0.964 g/mL at 25 °C(lit.)

vapor density 

3.04 (vs air)

vapor pressure 

0.43 mm Hg ( 20 °C)

refractive index 

n20/D 1.398(lit.)

FEMA 

2221 | BUTYRIC ACID

Fp 

170 °F

storage temp. 

-20°C

pka

4.83(at 25℃)

form 

Liquid

color 

Clear colorless

Specific Gravity

0.960 (20/4℃)

PH

2.5 (100g/l, H2O, 20℃)

Odor Threshold

0.00019ppm

explosive limit

2-12.3%(V)

Water Solubility 

MISCIBLE

JECFA Number

87

Merck 

14,1593

BRN 

906770

Stability:

Stability Flammable. Incompatible with strong oxidizing agents, aluminium and most other common metals, alkalies, reducing agents.

InChIKey

FERIUCNNQQJTOY-UHFFFAOYSA-N

CAS DataBase Reference

107-92-6(CAS DataBase Reference)

NIST Chemistry Reference

Butanoic acid(107-92-6)

EPA Substance Registry System

Butyric acid (107-92-6)

Hazard Codes 

C,Xi

Risk Statements 

34

Safety Statements 

26-36-45

RIDADR 

UN 2820 8/PG 3

WGK Germany 

1

RTECS 

ES5425000

F 

13

Autoignition Temperature

824 °F

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

2915 60 19

HazardClass 

8

PackingGroup 

III

Hazardous Substances Data

107-92-6(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 8.79 g/kg (Smyth)

Description

Butyric acid is a carboxylic acid also classified as a fatty acid. It exists in two isomeric forms as shown previously, but this entry focuses on n-butyric acid or butanoic acid. It is a colorless, viscous, rancid-smelling liquid that is present as esters in animal fats and plant oils. Butyric acid exists as a glyceride in butter, with a concentration of about 4%; dairy and egg products are a primary source of butyric acid. When butter or other food products go rancid, free butyric acid is liberated by hydrolysis, producing the rancid smell. It also occurs in animal fat and plant oils.

Chemical Properties

Butyric acid is a combustible, oily liquid with an unpleasant odor. The Odor Threshold is 0.0001 ppm.

Chemical Properties

Butyric acid, C3H7COOH, a colorless liquid with an obnoxious odor, occurring in spoiled butter.It miscible with water, alcohol, and ether.It is used in the synthesis of butyrate ester perfume and flavor ingredients and in disinfectants and pharmaceuticals,

Chemical Properties

n-Butyric acid has a persistent, penetrating, rancid, butter-like odor and burning, acid taste.

Uses

Butyric Acid is a fatty acid that is commonly obtained from butter fat. it has an objectionable odor which limits its uses as a food acid- ulant or antimycotic. it is an important chemical reactant in the manufacture of synthetic flavoring, shortening, and other edible food additives. in butter fat, the liberation of butyric acid which occurs during hydrolytic rancidity makes the butter fat unusable. it is used in soy milk-type drinks and candies.

Uses

It is used in plastics as a raw material for the cellulose acetate butyrate (CAB). Other uses of butyric acid are in disinfectants, pharmaceuticals, and feed supplements for plant and animals. Butyric acid derivatives play an important role in plant and animal physiology.

Uses

Butyric acid is used in the preparation of various butyrate esters. Low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes. As a consequence, they find use as food and perfume additives. It is also used as an animal feed supplement, due to the ability to reduce pathogenic bacterial colonization. It is an approved food flavoring in the EU FLAVIS database (number 08.005).
Due to its powerful odor, it has also been used as a fishing bait additive. Many of the commercially available flavors used in carp (Cyprinus carpio) baits use butyric acid as their ester base; however, it is not clear whether fish are attracted by the butyric acid itself or the substances added to it. Butyric acid was, however, one of the few organic acids shown to be palatable for both tench and bitterling. The substance has also been used as a stink bomb by Sea Shepherd Conservation Society to disrupt Japanese whaling crews, as well as by anti-abortion protesters to disrupt abortion clinics.

Production Methods

Butyric Acid is industrially prepared by the fermentation of sugar or starch, brought about by the addition of putrefying cheese, with calcium carbonate added to neutralize the acids formed in the process. The butyric fermentation of starch is aided by the direct addition of Bacillus subtilis. Salts and esters of the acid are called butyrates or butanoates.
Butyric acid or fermentation butyric acid is also found as a hexyl ester hexyl butyrate in the oil of Heracleum giganteum (a type of hogweed) and as the octyl ester octyl butyrate in parsnip (Pastinaca sativa); it has also been noticed in skin flora and perspiration.

Preparation

Obtained by fermentation of starches and molasses with selective enzymes (Granulo saccharobutyricum); it is subsequently isolated as the calcium salt.

Definition

ChEBI: A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.

Production Methods

Butyric acid is produced by oxidation of butyraldehyde (CH3(CH2)2CHO) or butanol (C4H9OH). It can also be formed biologically by the oxidation of sugar and starches using bacteria.

Definition

A colorless liquid carboxylic acid. Esters of butanoic acid are present in butter.

Aroma threshold values

Detection: 240 ppb to 4.8 ppm

Taste threshold values

Taste characteristics at 250 ppm: acidic, sour, cheesy, dairy, creamy with a fruity nuance.

General Description

A colorless liquid with a penetrating and unpleasant odor. Flash point 170°F. Corrosive to metals and tissue. Density 8.0 lb /gal.

Air & Water Reactions

Water soluble.

Reactivity Profile

(3R,4S)-1-Benzoyl-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone can react with oxidizing agents. Incandescent reactions occur with chromium trioxide above 212°F. Also incompatible with bases and reducing agents. May attack aluminum and other light metals .

Hazard

Strong irritant to skin and tissue.

Health Hazard

Inhalation causes irritation of mucous membrane and respiratory tract; may cause nausea and vomiting. Ingestion causes irritation of mouth and stomach. Contact with eyes may cause serious injury. Contact with skin may cause burns; chemical is readily absorbed through the skin and may cause damage by this route.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Safety Profile

Moderately toxic by ingestion, skin contact, subcutaneous, intraperitoneal, and intravenous routes. Human mutation data reported. Severe skin and eye irritant. A corrosive material. Combustible liquid. Could react with oxidizing materials. Incandescent reaction with chromium trioxide above 100'. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Shipping

UN2820 Butyric acid, Hazard class: 8; Labels: 8—Corrosive material. UN2529 Isobutyric acid, Hazard Class: 3; Labels: 3—Flammable liquid, 8—Corrosive material

Purification Methods

Distil the acid, them mix it with KMnO4 (20g/L), and fractionally redistil, discarding the first third of the distillate [Vogel J Chem Soc 1814 1948]. [Beilstein 2 IV 779.]

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Preparation Products

Acetic acid glacial-->Isobutyric acid-->Phenvalerate-->Butyryl chloride-->(2S,3S)-2-Amino-3-methylpentanoic acid-->Butyric anhydride-->Ethyl butyrate-->Direct Blue 71-->ALPHA-KETOBUTYRIC ACID SODIUM SALT-->Reactive Red Brown K-B3r-->Butyramide-->Progabide-->1,4-Bis(4-cyanostyryl)benzene-->4-Heptanone-->disodium 3-[[4'-[(6-amino-1-hydroxy-3-sulphonato-2-naphthyl)azo]-3,3'-dimethoxy[1,1'-biphenyl]-4-yl]azo]-4-hydroxynaphthalene-1-sulphonate-->Vat Orange 9-->Reactive Orange 1-->Isoamyl butyrate-->1-OCTEN-3-YL BUTYRATE-->CIS-3-HEXENYL BUTYRATE-->CYCLOHEXYL BUTYRATE-->2-Ethyl-1,3-cyclopentanedione-->Benzyldimethylcarbinyl butyrate-->Phenethyl butyrate-->FEMA 2686-->ALLYL BUTYRATE-->2-Bromobutyric acid-->Leather Black-->PANTOTHENIC ACID CALCIUM SALT MONOHYDRATE-->FEMA 2368-->FEMA 3332

Raw materials

Nitric acid-->tert-Butanol-->Oxygen-->Vanillin-->1-Pentanol-->Butyraldehyde-->Molasses-->Cobalt acetate-->Manganese triacetate dihydrate-->BUTTER