(2E)-2-Butenoic acid
Trans-crotonic acid
CAS: 107-93-7
Molecular Formula: C4H6O2
(2E)-2-Butenoic acid - Names and Identifiers
| Name | Trans-crotonic acid |
| Synonyms | (e)-crotonicaci but-2-enoic acid (e)-crotonicacid (E)-Crotonic acid (2E)-but-2-enoate (e)-2-butenoicaci TRANS-CROTONIC ACID Trans-crotonic acid (2E)-2-Butenoic acid (2E)-but-2-enoic acid TRANS-2-BUTENOIC ACID trans-3-Methylacrylic acid |
| CAS | 107-93-7 |
| EINECS | 203-533-9 |
| InChI | InChI=1/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/p-1/b3-2+ |
| InChIKey | LDHQCZJRKDOVOX-NSCUHMNNSA-N |
(2E)-2-Butenoic acid - Physico-chemical Properties
| Molecular Formula | C4H6O2 |
| Molar Mass | 86.09 |
| Density | 1.027 g/mL at 25 °C (lit.) |
| Melting Point | 70-72 °C (lit.) |
| Boling Point | 180-181 °C (lit.) |
| Flash Point | 190°F |
| JECFA Number | 1371 |
| Water Solubility | 94 g/L (25 ºC) |
| Solubility | H2O: soluble |
| Vapor Presure | 0.19 mm Hg ( 20 °C) |
| Vapor Density | 2.97 (vs air) |
| Appearance | Crystalline Flakes |
| Color | White to light yellow |
| Merck | 14,2597 |
| BRN | 1719943 |
| pKa | 4.69(at 25℃) |
| PH | 3 (10g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Explosive Limit | 15.1%, 171°F |
| Refractive Index | 1.4228 |
| Physical and Chemical Properties | Trait: monoclinic needle-like or prismatic crystal. melting point 71.4~71.7 ℃ boiling point 184.7 ℃ relative density 1.108 refractive index 1.4228 soluble in ethanol, ether and acetone. |
| Use | Trans-butenoic acid is mainly used for the preparation of synthetic resins, plasticizers, drugs, but also for other organic synthesis |
(2E)-2-Butenoic acid - Risk and Safety
| Risk Codes | R21/22 - Harmful in contact with skin and if swallowed. R34 - Causes burns R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S37/39 - Wear suitable gloves and eye/face protection |
| UN IDs | UN 2823 8/PG 3 |
| WGK Germany | 3 |
| RTECS | GQ2900000 |
| HS Code | 29161940 |
| Hazard Class | 8 |
| Packing Group | III |
| Toxicity | LD50 orally in rats: 1.0 g/kg (Smyth, Carpenter) |
(2E)-2-Butenoic acid - Upstream Downstream Industry
| Downstream Products | Crotamiton |
(2E)-2-Butenoic acid - Nature
Open Data Verified Data
monoclinic needle-like or prismatic crystals. There are cis and trans isomers.
CIS: Melting point 15.5 °c. Boiling point 169 °c (look kPa). The relative density was 1.0265. Refractive index 4456. The solubility in lOOmL (20 °c) water was 7.61g. Soluble in ethanol. Co-heating with 60% sulfuric acid, Trace Hydrochloric acid or hydrogen bromide can be converted into trans-butenoic acid with a melting point of 71.4-71.7 °c. Boiling point 184.7 °c. Relative density (d15)1. 018. Refractive index (nD7) 1.4228 (80 °c). The solubility in lOOmL water (25 °c) was 9.4g. Soluble in ethanol, ether and acetone. It can be converted into cis-butenoic acid in toluene solution.
Last Update：2024-01-02 23:10:35
(2E)-2-Butenoic acid - Preparation Method
Open Data Verified Data
crotonaldehyde can be prepared by oxidation with air or oxygen in the presence of a mixture of copper acetate and cobalt acetate as catalysts.
In addition, a small amount of butenoic acid can be obtained from wood dry distillation, and can also be prepared by condensation of acetaldehyde and malonic acid in the experiment.
Last Update：2022-01-01 10:31:20
(2E)-2-Butenoic acid - Use
Open Data Verified Data
It is mainly used for resin, bactericide, coating, plasticizer and medicine. Its primary use is as a raw material for polyvinyl acetate coatings. In addition, the vinyl acetate-butenic acid copolymer can be used as a hot-melt adhesive for bookbinding books, and can also be used as a coating material for wallpaper, a Adhesive for paper, a laminate, and a film developer and an xerographic liquid component.
Last Update：2022-01-01 10:31:19
(2E)-2-Butenoic acid - Safety
Open Data Verified Data
- crotonic acid (1% in food) showed no significant toxicity in mice for 41 days. However, crotonic acid is irritating to the skin, and its irritation is similar to that of acrylic acid. Wear protective glasses and rubber gloves during operation.
- packed in paper or galvanized iron barrels lined with plastic bags. According to the "general chemical regulations" for storage and transportation.
Last Update：2022-01-01 10:31:20
(2E)-2-Butenoic acid - Reference Information
| FEMA | 3908 | (E)-2-BUTENOIC ACID |
| LogP | 0.85 at 25℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | crotonic acid, also known as crotonic acid, has cis and trans isomers. The usual crotonic acid is trans-butenoic acid, which is converted to cis-form in toluene solution. It is an unsaturated fatty acid, the molecule contains double bonds and carboxyl groups, has a strong reactivity, crotonic acid is an important chemical intermediate, widely used in the preparation of resins, coatings, fungicides, plasticizers and drugs, etc. |
| preparation | in a reaction flask equipped with a stirrer, a reflux condenser (with a calcium chloride drying tube), 25g(32,mL,0.57mol) of freshly distilled acetaldehyde (2) are added, 59.5g(0.57mol) of malonic acid in dry powder form, 67g of dry pyridine and 0.5 of piperidine are dried. Ice water bath or refrigerator for 24h. The steam bath is then heated until no carbon dioxide gas has evolved. After cooling in an ice bath, 60ml of 1:1 dilute sulfuric acid was added, and the mixture was placed in an ice bath for 3-4 hours. The precipitated crystals were filtered out. The mother liquor was extracted three times with ether, dried over anhydrous sodium sulfate, and the ether was distilled off to obtain a partial solid. The two solids were combined and recrystallized from petroleum ether to obtain 20g of crotonic acid (1) at MP 72 ° C. In 41% yield. |
| uses | trans-butenoic acid is mainly used in the preparation of synthetic resins, plasticizers, also used in other organic synthesis used as a synthetic rubber softener, also used in the synthesis of resin and medicine crotonic acid is unsaturated fatty acid, the molecule contains double bonds and carboxyl groups, therefore, it has strong reactivity and has various industrial applications, mainly for the preparation of various resins, fungicides, surface coatings, plasticizers and drugs. Its primary use is as a raw material for polyvinyl acetate coatings. In addition, the vinyl acetate-crotonic acid copolymer can be used as a hot-melt adhesive for binding books, and can also be used as a coating for wallpaper and an adhesive for paper and laminate, as well as a film developer and an xerographic liquid component. Crotonic acid series products: crotonic acid amide: from the acid or its acid chloride and ammonia reaction. Crotonoyl aniline: obtained from the reaction of an enoic acid chloride or butene anhydride with aniline and used in insecticides. Butenic anhydride: from the acid chloride and sodium butenate reaction, can also be produced by the reaction of acetic anhydride and acetic acid or ketene, used for the preparation of cellulose butenate and its derivatives. Crotonoyl chloride: derived from the action of enoic acid with carbon trichloride or phosphorus pentachloride, benzoyl chloride or thionyl chloride, etc., for the preparation of butenoates and their derivatives. The important butenic acid esters are methyl methacrylate, ethyl butenoate, n-butyl butenoate, vinyl butene, allyl butenoate. Amyl Esters of crotonic acid, gallyl Ester, 2-methylallyl Ester and 2-ethylethyl ester are all used in perfumes, of which benzyl esters, methyl cyanide and trimethylglycol esters are insecticides. Peroxycrotonic acid is a catalyst for the polymerization of vinyl chloride and vinylidene chloride. Crotonic acid is also used as a softening agent for synthetic rubber. A softening agent for preparing a synthetic rubber. Preparation of DL-threonine and vitamin A. for the preparation of various resins, fungicides, surface coatings, fungicides, plasticizers. |
| production method | using crotonaldehyde as raw material, it can be obtained by air or oxygen oxidation in the presence of a mixture of copper acetate and cobalt acetate as catalysts. There are continuous and batch processes. In addition, a small amount of butenoic acid can be obtained from wood dry distillation, and can also be prepared by condensation of acetaldehyde and malonic acid in the experiment. |
| autoignition temperature | 744 ° F. |
Last Update：2024-04-09 02:00:04
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