Sodium acrylate

solid

Liquid|WHITE POWDER WITH CHARACTERISTIC ODOUR.

3, 000 g of acrylic acid, 1, 470 g of dipentaerythritol (hereinafter referred to as 'DPET'), 70 g of 78percent sulfuric acid, 10 g of hydroquinone (hereinafter referred to as 'HQ') and 2, 450 g of toluene were charged in a 10 L reaction kettle and heated to 100 ° C. under a pressure of 53 kPa The mixture was heated in a set oil bath and reacted for 10 hours while removing the condensed water as azeotropic water with toluene. The weight of the reaction solution at this time was 6, 400 g.After completion of the reaction, 3, 500 g of toluene was added. Subsequently, 325 g of pure water was added thereto, followed by stirring, and the mixture was allowed to stand to separate phases in the upper layer (organic phase) and the lower layer (aqueous phase).To this upper layer (organic phase), 1, 700 g of a 20percent aqueous solution of sodium hydroxide was added and stirred, followed by standing to obtain 9, 280 g of the upper layer (organic phase) and 2, 270 g of the lower layer (aqueous phase) .This lower layer (aqueous phase) (hereinafter referred to as 'neutralized wastewater') was extracted from the reaction kettle and used for Examples 2 to 4 and Comparative shown below.The neutralized wastewater thus obtained was analyzed by absolute calibration curve method using liquid chromatography (product name: LC-10A, manufactured by Shimadzu Corporation) to find that sodium acrylate was 32.8percent (acrylic acid 25.1percent as an acid). The upper layer (organic phase) was further separated into an upper layer (organic phase) and a lower layer (aqueous phase) by adding 1, 360 g of a 20percent aqueous solution of sodium hydroxide to the mixture, (Organic phase) and the lower layer (aqueous phase), and the resulting upper layer (organic phase) was subjected to hydrolyzed monomethyl ether (hereinafter referred to as ' , Hereinafter referred to as 'MQ') was added thereto, and the toluene was distilled off under reduced pressure to obtain 2, 990 g of acrylate.To the 300 g of the neutral wastewater obtained above, 98percent sulfuric acid was gradually added until the pH reached 3. The added 98percent sulfuric acid was 49.2 g, the temperature being 22 to 37 ° C Next, the solution after the addition of sulfuric acid was cooled to 10 ° C while stirring the solution, the sodium sulfate was gradually precipitated, and sodium nitrite (solid phase), acrylyl acid and sodium nitrite (hereinafter referred to as ' (Aqueous phase) containing acrolein (acid) (salt) .) Separation of sodium sulfate (solid phase) by filtration yielded an aqueous solution (aqueous phase) containing acylic acid .The aqueous solution containing the acylic acid (salt) thus obtained was 169.6 g, and acrilic acid (salt) was contained in an amount of 37.4percent in terms of acetic acid. The acylic acid contained in the neutralized wastewater (Salt) was recovered as 84.2percent of the acylic acid in terms of acetic acid, and the concentration of sodium nitrite in the acylic acid (salt) aqueous solution was measured using an ion chromatograph [ICS1000 type manufactured by Nippon Diane Co., The result was 2.5percent.Note that the precipitated and recovered sodium nitrite was in a state of decahydrate, and 179.6 gWas obtained.Method (Unzue, M. et al., J. Appl. Polym. ScI, 1997, 66:1803): Sodium hydroxide (276.6 g, 0.69 mol) dissolve un-deionized water was placed in a round-bottom flask and kept in a bath for 10 minutes. Acrylic acid (59.75 g., 0.69 mol) was added drop wise under stirring to the above solution. After 30 minutes, the reaction mixture was freeze - dried. The product was dissolved in methanol and precipitated with diethyl ether. After filtering, a white powder (71.14 g, 0.65 mol) was obtained in 95percent yield.Example 4 details conversion of salts of 3-hydroxypropionic acid forming important conversion products, including, but not limited to, acrylates. The term 'melt' or as used herein describes the state of a source material introduced to a reactor at a temperature near, greater than, or equal to the melting point temperature. In exemplary tests, the sodium salt of 3-hydroxypropionic acid was mixed with a dehydration catalyst, e.g., Zr(OH)Example 6 This example describes the preparation of sodium acrylate from the sodium salt of 3-HP. A 21 g aqueous solution of the sodium salt of 3-HP, made from 5.027 g 30percent 3-HP and 0.69 g NaOH, was heated at 220°C in a Parr reactor for 2 hours. After cooling down to room temperature, the solution was analyzed by GC and HPLC for acrylic acid and 3- HP. The yield of and conversion to sodium acrylate from the sodium salt of 3-HP were 41.8percent and 61.3percent, respectively. This gave a 68.2percent selectivity from the sodium salt of 3- HP to sodium acrylate. The carbon balance of the reaction was 80.6percent.Example 7 (inventive example): Catalytic formation of sodium acrylate 1 , 2-bis(Di-ferf-butylphosphino)ethane (79.5 mg, 0.25 mmol) and Ni(COD)Example 5 (use in a catalytic reaction):An autoclave (inner volume = 160 mL) was made inert overnight (100 00, vacuum), and then purged with ethylene until the inner atmosphere was fully replaced. 1500 mgof the solid support with covalently immobilized dcpe (loading of 1, 2- bis(dicyclohexylphosphino)ethane = 0.0194 mmolig) from example 3, Ni(COD)2 (0.1 mmol, 28 mg) and triethylamine (10 mmol, 1011.9 mg) were suspended in THF (45 mL). The suspension was mixed with fine powdered NaH (10 mmol, 240 mg) and thenimmediately transferred under inert conditions into the autoclave at room temperature. The autoclave was pressurized with ethylene (5 bar) and 002 (10 bars) at room temperature, heated to 100 00 and stirred at 2000 rpm. After 68 hours of reaction the autoclave was cooled to room temperature and the excess pressure was released within 10 mm. To the reaction mixture a mixture of D20 -THF (15 mLilO mL) was added drop-wise. The resulting mixture was diluted with D20 (15 mL) and the biphasic liquid was extracted with diethyl ether (2 x 20 mL). The aqueous phase was mixed with 2, 2, 3, 3-d4- 3-(trimethylsilyl)propionic acid (0.167 mmol, 28.7 mg) and analyzed by 1H-NMR spectroscopy. Content: 0.192 mmol sodium acrylate (TON = 0.9).Example 4 details conversion of salts of 3-hydroxypropionic acid forming important conversion products, including, but not limited to, acrylates. The term 'melt' or as used herein describes the state of a source material introduced to a reactor at a temperature near, greater than, or equal to the melting point temperature. In exemplary tests, the sodium salt of 3-hydroxypropionic acid was mixed with a dehydration catalyst, e.g., Zr(OH)4, prepared internally, and a polymer inhibitor, e.g., 2, 6 dimethoxyphenol (DMP) (Sigma-Aldrich, St. Louis, Mo.) in a 1:1:1 (salt: catalyst: inhibitor) weight ratio and melted in vials in a batch reactor open to air atmosphere at 200° C. for 1, 2, 3, and 4 hours, respectively. Zr(OH)4 was prepared via ammonium hydroxide precipitation of zirconyl nitrate (Spectrum Chemicals, Gardena, Calif.) followed by drying in a vacuum oven at 50° C. Quantity of conversion products was determined by HPLC. Results are tabulated in Table 1.; Results for tests 1 through 4 showed an 86percent conversion with 90percent selectivity to Example 4 details conversion of salts of 3-hydroxypropionic acid forming important conversion products, including, but not limited to, acrylates. The term 'melt' or as used herein describes the state of a source material introduced to a reactor at a temperature near, greater than, or equal to the melting point temperature. In exemplary tests, the sodium salt of 3-hydroxypropionic acid was mixed with a dehydration catalyst, e.g., Zr(OH)4, prepared internally, and a polymer inhibitor, e.g., 2, 6 dimethoxyphenol (DMP) (Sigma-Aldrich, St. Louis, Mo.) in a 1:1:1 (salt:catalyst:inhibitor) weight ratio and melted in vials in a batch reactor open to air atmosphere at 200° C. for 1, 2, 3, and 4 hours, respectively. Zr(OH)4 was prepared via ammonium hydroxide precipitation of zirconyl nitrate (Spectrum Chemicals, Gardena, Calif.) followed by drying in a vacuum oven at 50° C. Quantity of conversion products was determined by HPLC. Results are tabulated in Table 1; Results for tests 1 through 4 showed an 86percent conversion with 90percent selectivity to Example 4 details conversion of salts of 3-hydroxypropionic acid forming important conversion products, including, but not limited to, acrylates. The term 'melt' or as used herein describes the state of a source material introduced to a reactor at a temperature near, greater than, or equal to the melting point temperature. In exemplary tests, the sodium salt of 3-hydroxypropionic acid was mixed with a dehydration catalyst, e.g., Zr(OH)4, prepared internally, and a polymer inhibitor, e.g., 2, 6 dimethoxyphenol (DMP) (Sigma-Aldrich, St. Louis, Mo.) in a 1:1:1 (salt:catalyst:inhibitor) weight ratio and melted in vials in a batch reactor open to air atmosphere at 200° C. for 1, 2, 3, and 4 hours, respectively. Zr(OH)4 was prepared via ammonium hydroxide precipitation of zirconyl nitrate (Spectrum Chemicals, Gardena, Calif.) followed by drying in a vacuum oven at 50° C. Quantity of conversion products was determined by HPLC. Results are tabulated in Table 1; Results for tests 1 through 4 showed an 86percent conversion with 90percent selectivity to Example 6 This example describes the preparation of

Intermediates|Surface active agents

Paints and coatings|Agricultural products (non-pesticidal)

10,000,000 - 50,000,000 lb

Molecular Weight:94.04
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:94.00307362
Monoisotopic Mass:94.00307362
Topological Polar Surface Area:40.1
Heavy Atom Count:6
Complexity:59.8
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes