Crotonic acid

Crotonic acid Property

Melting point:

70-72 °C (lit.)

Boiling point:

180-181 °C (lit.)

Density 

1.027 g/mL at 25 °C (lit.)

bulk density

543kg/m3

vapor density 

2.97 (vs air)

vapor pressure 

0.19 mm Hg ( 20 °C)

refractive index 

1.4228

FEMA 

3908 | (E)-2-BUTENOIC ACID

Flash point:

190 °F

storage temp. 

Store below +30°C.

solubility 

H2O: soluble

pka

4.69(at 25℃)

form 

Crystalline Flakes

color 

White to light yellow

PH

3 (10g/l, H2O, 20℃)

Odor

at 1.00 %. milky

Odor Type

milky

explosive limit

15.1%, 171°F

Water Solubility 

94 g/L (25 ºC)

Merck 

14,2597

JECFA Number

1371

BRN 

1719943

InChIKey

LDHQCZJRKDOVOX-NSCUHMNNSA-N

LogP

0.85 at 25℃

CAS DataBase Reference

107-93-7(CAS DataBase Reference)

NIST Chemistry Reference

Crotonic acid(107-93-7)

EPA Substance Registry System

2-Butenoic acid, (2E)- (107-93-7)

Safety

Hazard Codes 

C,N,Xi

Risk Statements 

21/22-34-50/53-36/37/38

Safety Statements 

26-36/37/39-45-61-37/39

RIDADR 

UN 2823 8/PG 3

WGK Germany 

3

RTECS 

GQ2900000

Autoignition Temperature

744 °F

HazardClass 

8

PackingGroup 

III

HS Code 

29161940

Toxicity

LD50 orally in rats: 1.0 g/kg (Smyth, Carpenter)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Crotonic acid Chemical Properties,Usage,Production

Chemical Properties

Crotonic acid is a white to light yellow crystalline flakes with a pungent odor. It is moderately soluble in water but highly soluble in organic solvents such as ethanol and ether.

Uses

trans-Crotonic acid is used in the copolymerization of crotonic acid hydrogel systems by using gamma-rays. The crosslinked copolymeric crotonic acid hydrogels release fertilizers and drugs that help to prevent environmental pollution.

Preparation

(E)-2-Butenoic acid may be formed by oxidation of crotonaldehyde, 2-butenal. If (Z)-butenoic acid is heated at 180°C, it is converted to (E)-2-butenoid acid.

Definition

ChEBI: Crotonic acid is a but-2-enoic acid with a trans- double bond at C-2. It has been isolated from Daucus carota. It has a role as a plant metabolite. It is a conjugate acid of a crotonate.

Application

Crotonic acid is an unsaturated fatty acid containing a double bond and a carboxyl group in its molecular structure, rendering it highly reactive. It serves various industrial applications, primarily in the preparation of resins, fungicides, surface coatings, plasticisers, and pharmaceuticals.

General Description

Crotonic acid undergoes esterification with butan-2-ol by following second order reaction kinetics.

Flammability and Explosibility

Not classified

storage

Store at RT

Purification Methods

Distil the acid under reduced pressure and/or recrystallise it from pet ether (b 60-80o) or water, or by partial freezing of the melt. [Beilstein 2 IV 1498.]

References

[1] VAHIDEH ELHAMI Mark A H, BOELO SCHUUR* Crotonic Acid Production by Pyrolysis and Vapor Fractionation of Mixed Microbial Culture-Based Poly(3-hydroxybutyrate-co-3-hydroxyvalerate)[J]. Industrial & Engineering Chemistry Research, 2023, 62 2: 916-923. DOI:10.1021/acs.iecr.2c03791.
[2] ZHIQUN YU*, JIADI ZHOU Continuous Flow Synthesis of Crotonic Acid from Crotonaldehyde[J]. Organic Process Research & Development, 2024, 28 5: 1773-1782. DOI:10.1021/acs.oprd.3c00376.
[3] KANG S, CHEN R, FU J, et al. Catalyst-free valorization of poly-3-hydroxybutyrate to crotonic acid†[J]. Reaction Chemistry & Engineering, 2021, 10: 1791-1795. DOI:10.1039/D1RE00273B.