Introduction：Basic information about Crotonic acid CAS 107-93-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Crotonic acid Basic information
| Product Name: | Crotonic acid |
| Synonyms: | TRANS-2-BUTENOIC ACID;TRANS-CROTONIC ACID;(2E)-2-Butenoic acid;(e)-2-butenoicaci;(E)-CH3CH=CHCOOH;(E)-Crotonic acid;(e)-crotonicaci;(e)-crotonicacid |
| CAS: | 107-93-7 |
| MF: | C4H6O2 |
| MW: | 86.09 |
| EINECS: | 203-533-9 |
| Product Categories: | organic chemical;107-93-7 |
| Mol File: | 107-93-7.mol |
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Crotonic acid Chemical Properties
| Melting point | 70-72 °C (lit.) |
| Boiling point | 180-181 °C (lit.) |
| bulk density | 543kg/m3 |
| density | 1.027 g/mL at 25 °C (lit.) |
| vapor density | 2.97 (vs air) |
| vapor pressure | 0.19 mm Hg ( 20 °C) |
| refractive index | 1.4228 |
| FEMA | 3908 | (E)-2-BUTENOIC ACID |
| Fp | 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 |
| InChI | 1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+ |
| InChIKey | LDHQCZJRKDOVOX-NSCUHMNNSA-N |
| SMILES | [H]\C(C)=C(\[H])C(O)=O |
| 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 Information
| 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 |
| Storage Class | 8A - Combustible corrosive hazardous materials |
| Hazard Classifications | Eye Dam. 1 |
| Toxicity | LD50 orally in rats: 1.0 g/kg (Smyth, Carpenter) |
Crotonic acid Usage And Synthesis
| 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, itis 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. |
Crotonic acid Preparation Products And Raw materials
| Raw materials | Malonic acid-->Copper (II) acetate monohydrate-->Crotonaldehyde (trans predominantly)-->Cobalt acetate-->Crotonic acid |
| Preparation Products | DL-3-Hydroxybutyric acid sodium salt-->3-PHENYLBUTYRIC ACID-->DL-3-HYDROXYBUTYRIC ACID SODIUM SALT-->Crotamiton-->4-BROMOCROTONIC ACID-->BETA-METHYLLEVULINIC ACID-->2,3-DIBROMOBUTYRIC ACID-->3-Mercaptobutyric acid-->DL-3-Aminobutyric acid-->2-Butenoic acid, cyclohexyl ester, (2E)--->HEPTYL-CROTONATE-->HEXYLCROTONATE |
