2-Propenoic acid butyl ester
Butyl Acrylate
CAS: 141-32-2
Molecular Formula: C7H12O2
2-Propenoic acid butyl ester - Names and Identifiers
| Name | Butyl Acrylate |
| Synonyms | BA Butyl Acrylate Butyl acrylate n-Butyl Acrylate BUTYL-2-ACRYLATE Butyl 2-Propenoate butyl prop-2-enoate Acrylsure-n-butylester 2-methylidenehexanoate Propenoic acid n-butyl ester 2-Propenoic acid butyl ester BUTYL ACRYLATE (STABILISED WITH HYDROQUI N-BUTYL ACRYLATE , STABILIZED WITH 50PPM 4-METHOXYPHENOL |
| CAS | 141-32-2 |
| EINECS | 205-480-7 |
| InChI | InChI=1/C7H12O2/c1-3-4-5-6(2)7(8)9/h2-5H2,1H3,(H,8,9)/p-1 |
| InChIKey | CQEYYJKEWSMYFG-UHFFFAOYSA-N |
2-Propenoic acid butyl ester - Physico-chemical Properties
| Molecular Formula | C7H12O2 |
| Molar Mass | 128.17 |
| Density | 0.894 g/mL at 25 °C(lit.) |
| Melting Point | -69 °C |
| Boling Point | 61-63°C60mm Hg(lit.) |
| Flash Point | 63°F |
| Water Solubility | 1.4 g/L (20 ºC) |
| Solubility | 1.7g/l |
| Vapor Presure | 3.3 mm Hg ( 20 °C) |
| Vapor Density | >1 (vs air) |
| Appearance | Liquid |
| Color | Clear Colorless |
| Odor | Fruity |
| Exposure Limit | TLV-TWA 10 ppm (～55 mg/m3) (ACGIH). |
| Merck | 14,1539 |
| BRN | 1749970 |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, strong bases. |
| Sensitive | Light Sensitive |
| Explosive Limit | 1.1-7.8%(V) |
| Refractive Index | n20/D 1.410(lit.) |
| Physical and Chemical Properties | Character: colorless liquid. melting point -64.6 ℃ boiling point 146~148 ℃ relative density 0.894 refractive index 1.4174 flash point 39 ℃ solubility, ethyl ether, acetone and other organic solvents. Almost insoluble in water, 20 degrees in water solubility of 0.14g/100ml. |
| Use | Mainly used in the preparation of synthetic resin, synthetic fiber, synthetic rubber, plastics, coatings, adhesives, etc |
2-Propenoic acid butyl ester - Risk and Safety
| Risk Codes | R11 - Highly Flammable R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R37/38 - Irritating to respiratory system and skin. R43 - May cause sensitization by skin contact R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/37/38 - Irritating to eyes, respiratory system and skin. R10 - Flammable |
| Safety Description | S16 - Keep away from sources of ignition. S25 - Avoid contact with eyes. S37 - Wear suitable gloves. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S9 - Keep container in a well-ventilated place. S36/37 - Wear suitable protective clothing and gloves. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 1993 3/PG 2 |
| WGK Germany | 2 |
| RTECS | UD3150000 |
| FLUKA BRAND F CODES | 10 |
| TSCA | Yes |
| HS Code | 29161230 |
| Hazard Class | 3 |
| Packing Group | III |
| Toxicity | LD50 orally in rats: 3.73 g/kg (Smyth) |
2-Propenoic acid butyl ester - Upstream Downstream Industry
| Raw Materials | Acrylic acid 1-Butanol |
| Downstream Products | Acrylic acid Polymers |
2-Propenoic acid butyl ester - Nature
Open Data Verified Data
colorless liquid. The relative density was 0. 894. Melting Point -64.6 °c. Boiling Point 146~148 degrees C; 69 degrees C (6.7kPa). Flash point (closed cup) 39 °c. Refractive index 4174. Soluble in ethanol, ether, acetone and other organic solvents. Almost insoluble in water, 20 degrees in water solubility of 0.14g/lOOmL.
Last Update：2024-01-02 23:10:35
2-Propenoic acid butyl ester - Preparation Method
Open Data Verified Data
- the esterification of acrylic acid and n-butanol by methyl acrylate method is carried out under the catalysis of sulfuric acid, followed by neutralization, water washing, alcohol removal and distillation to obtain the finished butyl acrylate. Acrylic acid is obtained by oxidation of propylene or hydrolysis of acrylonitrile (see Methyl Acrylate Production method).
- acrylonitrile hydrolysis method acrylonitrile is heated to 90 ° C. Together with sulfuric acid to hydrolyze acrylonitrile to a sulfate of acrylamide, and the sulfate is further esterified to form an acrylic acid ester. In recent years, there are patent reports that the yield of Ester can reach 95% by using acrylonitrile as raw material and one-step production.
- β-propiolactone method using acetic acid as raw material and triethyl phosphate as catalyst, ketene was synthesized by pyrolysis at 625~730 ℃, the gas phase reaction with anhydrous formaldehyde is then carried out in the presence of AICl3 or BF3 catalysts to form beta propiolactone. Beta propiolactone directly with butanol and sulfuric acid instead of butyl acrylate.
Last Update：2022-01-01 10:32:53
2-Propenoic acid butyl ester - Use
Open Data Verified Data
high molecular polymer monomer. Mainly used for fiber, rubber, plastic, coatings, adhesives, Textile Auxiliaries, can also be used as leather and paper processing agent.
Last Update：2022-01-01 10:32:53
2-Propenoic acid butyl ester - Safety
Open Data Verified Data
- the toxicity of this product is similar to that of methyl acrylate. The oral LD50 in rats was 3730mg/kg. Irritation to eyes and skin. The maximum allowable concentration is 10-5. Air should be circulated at the operating site. The operator should wear protective equipment.
- galvanized iron drum packaging. Store in a cool, dry and ventilated place. Polymerization inhibitor should be added before storage and transportation
Last Update：2022-01-01 10:32:54
2-Propenoic acid butyl ester - Reference Information
| olfactory threshold (Odor Threshold) | 0.00055ppm |
| LogP | 2.38 at 25℃ |
| (IARC) carcinogen classification | 3 (Vol. 39, Sup 7, 71) 1999 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | butyl acrylate is mainly used to make polymer monomers of fibers, rubber and plastics. The organic industry is used to make adhesives, emulsifiers and as intermediates in organic synthesis. The paper industry is used to make paper reinforcers. The coating industry is used to make acrylate coatings. Butyl acrylate (butyl acrylate) is the most important variety of acrylates. In the existing continuous production process, direct esterification of butyl acrylate is the main production method in the world at this stage. The main process flow is: The raw materials acrylic acid and n-butanol are esterified in two series reactors, organic acids are used as catalysts, and the method of dehydration while reacting is adopted, so that the reversible esterification equilibrium reaction is carried out in the direction of butyl ester formation as far as possible. |
| Application | Butyl acrylate is a more active variety in general acrylates. It is a soft monomer with strong reactivity and can be used with a variety of hard monomers (Hydroxyalkyl, glycidyl, methylamide) produce crosslinking, copolymerization and calibration to form emulsions, water-soluble copolymerization and other polymers, and can prepare plastic and cross-linked polymers to obtain many products with different characteristics such as viscosity, hardness, durability, and glass transition temperature. Butyl acrylate is an important intermediate with high application consumption. It is widely used in coatings, textile adhesives, plastic synthetic fibers, detergents, super absorbent materials, chemical additives (dispersion, flocculation, thickening, etc.), synthetic rubber and other industries. Especially as MMA and MBS resin modifiers, it has attracted much attention abroad. |
| Preparation | A purification method of butyl acrylate crude product, comprising the following steps: 1) Extraction: using water as an extractant, the butyl acrylate crude product obtained by esterification reaction and the extractant are continuously extracted in countercurrent; the organic acid catalyst in the butyl acrylate crude product enters the aqueous phase, and the butyl acrylate and by-products enter the residual organic phase for separation, the extracted organic phase continuously enters the static mixer; 2) Mixing and neutralization: the liquid alkali continuously enters the static mixer, continuously and fully mixes with the extracted organic phase, carries out the neutralization reaction, and removes the organic acids in the by-product to obtain the reaction mixed material with a pH of 9~12;3) Washing and recovery: the reaction mixed material in step 2) enters the washing tower for washing, the butyl acrylate in the reaction mixture and the by-products that remove organic acids flow out from the upper part of the washing tower, the salt produced by the neutralization reaction and the impurities dissolved in water flow out from the bottom of the washing tower, and the organic components in the bottom liquid of the tower are recovered; 4) Separation and purification: Butyl acrylate and the by-products that remove organic acids are distilled to remove light components and heavy components to obtain butyl acrylate products. |
| uses | mainly used to make synthetic resins, synthetic fibers, synthetic rubber, plastics, coatings, adhesives, etc. acrylic acid and its esters are widely used in industry. In the process of use, acrylates are often polymerized into polymers or copolymers. Butyl acrylate (as well as methyl ester, ethyl ester, 2-ethylhexyl ester) is a soft monomer, which can be combined with various hard monomers such as methyl methacrylate, styrene, acrylonitrile, vinyl acetate, etc., and functional monomers such as (meth) hydroxyethyl acrylate, hydroxypropyl ester, glycidyl ester, (meth) acrylamide and base derivatives are copolymerized, crosslinked, grafted, etc., to make more than 200-700 acrylic resin products (mainly emulsion type, solvent-based and water-soluble), widely used in coatings, adhesives, acrylic fiber modification, plastic modification, fiber and fabric processing, paper treatment agents, leather processing and acrylic rubber and many other aspects. Used as a monomer and organic synthesis intermediate for polymers and resins Industrially, it is prepared by direct esterification of acrylic acid and butanol under sulfuric acid catalysis. It is a monomer for synthesizing acrylic resin, which is mainly used for preparing coatings, adhesives, resins and acrylic rubber. Butyl acrylate is a soft monomer, which can be used with various hard monomers such as methyl methacrylate, styrene, acrylonitrile, ethylene acetate, etc. and functional monomers such as hydroxyethyl acrylate (propyl), hydroxyethyl methacrylate (propyl) ester, glycidyl ester, acrylamide, etc. are copolymerized to make acrylic resins with different properties. 1. Polymerizable monomer, used for soft polymers, plays an internal plasticizing role in copolymers. For the preparation of coatings, textiles, papermaking, leather, building adhesives and other industrial resins. 2. Organic synthesis. |
| production method | the production methods of acrylate include acrylonitrile hydrolysis method, β-propiolactone method, repee method and improved repee method, cyanoethanol method and propylene direct oxidation method. 1. Cyanoethanol method uses chloroethanol and sodium cyanide as raw materials to react to generate cyanoethanol, and cyanoethanol is hydrolyzed in the presence of sulfuric acid to generate acrylic acid. 2. Acrylonitrile hydrolysis method Due to the abundant sources of acrylonitrile, a method of producing acrylate from acrylonitrile has been developed. Now industrialized methods include Societe Ugine method and Standard Oil Co(O-hio) method. Acrylonitrile and sulfuric acid are heated to 90°C to hydrolyze acrylonitrile to acrylamide sulfate, which is further esterified to form acrylate. In recent years, there have been patent reports that acrylonitrile is used as raw material and produced by one-step method, and the yield of ester can reach 95%. 3. The beta-propanolactone method uses acetic acid (or acetone) as raw material and triethyl phosphate as catalyst, and cleaves to generate ketene at 625-730°C. Then it reacts with anhydrous methyl vinegar in the presence of AICI3 or BF3 catalyst in the gas phase at 25°C to produce β-propiolactone: if the target product is acrylic acid, the propiolactone is contacted with hot 100% phosphoric acid to form acrylic acid; If the target product is acrylate, crude propiolactone can directly react with the corresponding alcohol and sulfuric acid without purification. 4. During the Second World War, Reppe discovered two methods in its research work to synthesize acrylic acid or propylene ester by reacting acetylene, carbon monoxide with water or alcohol. The "stoichiometric method" and the "catalytic method" were later developed into the improved Repee method used by Rohm & Hass in production and the high-pressure Repee method used by Dow-Badiche. (1) stoichiometric method This method is to react acetylene, nickel carbonyl (providing carbon monoxide) with water or alcohol under relatively mild conditions (40 ℃,0.101MPa) to produce acrylic acid or acrylate:(2) catalytic method acetylene, carbon monoxide, alcohol in the presence of nickel carbonyl catalyst, acrylate is prepared by reacting at 150 ℃ and 1.50-3MPa:(3) Improved Leipe method This method is a combination of the above two methods. After the stoichiometric reaction starts, carbon monoxide and acetylene are introduced, and the reaction can be continued. The carbon monoxide required for the reaction is 80% available gas carbon monoxide, while nickel carbonyl only needs to provide 20%. (4) High-pressure Rippe method This method is characterized by using tetrahydrofuran as a solvent to dissolve the acetylene required for the reaction in tetrahydrofuran first, which can reduce the risk of high-pressure treatment of acetylene. At the same time, nickel carbonyl is not used, and nickel salt is only used as a catalyst to react at 200-225 ℃ and 8.11-10.13MPa. (5) Propylene direct oxidation propylene gas phase air catalytic oxidation is the latest method to produce acrylic acid and its esters. Raw material consumption quota: 770kg/t acrylic acid and 610kg/t n-butanol. Uses: Acrylic acid and its esters are widely used in industry. In the process of use, acrylates are often polymerized into polymers or copolymers. Butyl acrylate (as well as methyl ester, ethyl ester, 2-ethylhexyl ester) is a soft monomer, which can be combined with various hard monomers such as methyl methacrylate, styrene, acrylonitrile, vinyl acetate, etc., and functional monomers such as (meth) hydroxyethyl acrylate, hydroxypropyl ester, glycidyl ester, (meth) acrylamide and base derivatives are copolymerized, crosslinked, grafted, etc., to make more than 200-700 acrylic resin products (mainly emulsion type, solvent-based and water-soluble), widely used in coatings, adhesives, acrylic fiber modification, plastic modification, fiber and fabric processing, paper treatment agents, leather processing and acrylic rubber and many other aspects. |
| category | flammable liquid |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 900 mg/kg; Oral-mouse LD50:7561 mg/kg |
| stimulation data | skin-rabbit 10 mg/24 hours mild; Eye-rabbit 50 mg/24 hours mild |
| flammability hazard characteristics | flammable in case of open flame, high temperature and strong oxidant; Combustion emission stimulating liquid |
| storage and transportation characteristics | complete packaging, light loading and unloading; warehouse ventilation, away from open flames, high temperature, separate storage from oxidant |
| fire extinguishing agent | foam, dry powder, carbon dioxide |
| occupational standard | TWA 10 PPM ( 55 mg/m3); STEL 20 PPM (110 mg/m3) |
| auto-ignition temperature | 559 °F |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
| immediate life-threatening and health concentration | 113 ppm |
Last Update：2024-06-12 11:39:18
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