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[ CAS No. 7446-81-3 ]

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Chemical Structure| 7446-81-3
Chemical Structure| 7446-81-3
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CAS No. :7446-81-3 MDL No. :MFCD00067207
Formula : C3H3NaO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :94.04 g/mol Pubchem ID :4068533
Synonyms :

Safety of [ 7446-81-3 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P305+P351+P338-P273 UN#:3077
Hazard Statements:H315-H318-H335-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7446-81-3 ]

  • Upstream synthesis route of [ 7446-81-3 ]
  • Downstream synthetic route of [ 7446-81-3 ]

[ 7446-81-3 ] Synthesis Path-Upstream   1~11

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Reference: [1] Russian Journal of Physical Chemistry, 1984, vol. 58, # 11, p. 1650 - 1652[2] Zhurnal Fizicheskoi Khimii, 1984, vol. 58, p. 2719 - 2721
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YieldReaction ConditionsOperation in experiment
32.8 %Chromat.
Stage #1: With Dipentaerythritol; sulfuric acid; hydroquinone In toluene at 100℃; for 10 h;
Stage #2: With sodium hydroxide In water; toluene
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 Example 1 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.
Reference: [1] Patent: JP5720528, 2015, B2, . Location in patent: Paragraph 0060-0063; 0065-0067
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YieldReaction ConditionsOperation in experiment
96.8% With sodium hydroxide In water; acetone Example 1
Preparation of Sodium Acrylate
12.01 g (0.3003 mol) sodium hydroxide and 10 ml water were added to a 50-ml Erlenmayer flask equipped with a magnetic stirring bar, and the mixture was stirred to dissolution.
The sodium hydroxide solution was then carefully added to a 250-ml beaker containing 28.03 g (0.3893 mol) acrylic acid (exothermic reaction), with continuous stirring.
The mixture was allowed to cool, 50 ml of acetone were added, and the precipitate vacuum filtered.
The wet sodium acrylate was first air dried and subsequently dried in an oven at 55°-60° C. for 12-15 hours to obtain 27.31 g (96.8percent yield) of sodium acrylate.
A similar procedure was used for the preparation of potassium acrylate, except that potassium hydroxide was used instead of sodium hydroxide.
95% With sodium hydroxide In water for 0.666667 h; 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.
Reference: [1] Patent: US5491244, 1996, A,
[2] Patent: WO2008/85556, 2008, A2, . Location in patent: Page/Page column 24
[3] Patent: US5072028, 1991, A,
[4] Patent: US2004/115251, 2004, A1,
[5] Patent: US2004/115251, 2004, A1,
[6] Patent: US2008/194863, 2008, A1, . Location in patent: Page/Page column 6-7
[7] Materials Research Bulletin, 2010, vol. 45, # 1, p. 56 - 62
[8] Russian Journal of Applied Chemistry, 2011, vol. 84, # 7, p. 1253 - 1256
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YieldReaction ConditionsOperation in experiment
61.8% at 200℃; for 1 - 4 h; Example 4; 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 sodium acrylate within 1 hour. Only slight increases in conversion were obtained at periods longer than 1 hour. Mass balances were approximately 100percent. Results further showed that while dimers (e.g., ether and ester dimers of 3-hydroxypropionic acid) and polymers form during heating, these moieties are still converted to acrylate products. Rates for conversion of ether dimers and ester dimers to acrylates are lower than for conversion of the 3-hydroxypropionic acid monomer. In other melt tests using ECS-3.(R). catalyst (Engelhard, Iselin N.J.), after 2 hours, combined yield of sodium acrylate and polymer was 91.2percent, with a 94.5percent conversion and a sodium acrylate selectivity of 96.4percent.
41.8 %Chromat. at 220℃; for 2 h; 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.
Reference: [1] Patent: US2007/219397, 2007, A1, . Location in patent: Page/Page column 10-11
[2] Patent: US2007/219391, 2007, A1, . Location in patent: Page/Page column 10
[3] Patent: US2007/219391, 2007, A1, . Location in patent: Page/Page column 10
[4] Patent: WO2003/82795, 2003, A2, . Location in patent: Page/Page column 11
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Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2011, vol. 54, # 12, p. 743 - 748
[2] Patent: US2013/79554, 2013, A1, . Location in patent: Paragraph 0057-0064
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YieldReaction ConditionsOperation in experiment
2.55 mmol
Stage #1: With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis(di-tert-butyl)phosphinoethane In chlorobenzene at 45℃; for 0.5 h; Autoclave
Stage #2: at 20 - 60℃;
Stage #3: With sodium t-butanolate In chlorobenzene for 1 h;
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)2 (69 mg, 0.25 mmol) were suspended in chlorobenzene (10 ml). The mixture was stirred until a red solution formed. The mixture was transferred to an autoclave and diluted with chlorobenzene (10 ml). The autoclave was charged with ethylene to 20 bar. The mixture was stirred (600 rpm) at 45°C for 30 minutes. In step 1 , the mixture was cooled to room temperature and the ethylene pressure was reduced to 10 bar. CO2 was injected until a final pressure of 50 bar had been established. The mixture was stirred (600 rpm) at 60°C for 2 h. The pressure was released, the mixture was cooled to room temperature, and the reactor was charged with ethylene (20 bar) and stirred for 1 min, in the course of which the pressure fell to 1 bar. This step was repeated three times. At ethylene pressure 1 bar, NaOfBu (48 mg, 0.5 mmol) was added to the mixture in step 2 and stirred for 1 h. The autoclave was charged with ethylene (20 bar), and the mixture was stirred at 45°C for a further hour. After 18 cycles (steps 1 and 2), the pressure was released. D2O (46 ml) with Me4l (25.1 mg, 0.125 mmol) was added as an internal standard. 1 H NMR and HPLC analysis of the aqueous extract showed a superstoichiometric content of sodium acrylate (2.55 mmol, 1020percent yield based on Ni(COD)2). H NMR (300 MHz, TH F-c/8): δ (ppm) = 1 .24 (m, 36H, C(CH3)3), 1 .65-1 .85 (m, 4H, CH2), 2.18 (m, 1 H, olefin CH), 2.72 (br, 1 H, olefin CH), 10.84 (br, 1 H, COOH). 3 P{ H} NMR (81 MHz, CD2CI2, 298 K), δ (ppm) = 87.73 (d, JP,P = 55.56 Hz), 95.98 (d, JP,P = 55.56 Hz). HPLC (Shodex RSpak KC-81 1 300 χ 8 mm (2 columns), 40°C, injection volume 100 μΙ_, flow rate: 1 ml/min, detection: λ = 205 nm, eluent: 0.1 percent phosphoric acid): 0.88percent by weight of acrylic acid.
0.284 mmol With sodium hydride; triethylamine In tetrahydrofuran at 20 - 100℃; for 68 h; Autoclave 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).
Reference: [1] Patent: WO2013/98772, 2013, A1, . Location in patent: Page/Page column 22-23
[2] Patent: US2013/172616, 2013, A1, . Location in patent: Paragraph 0142; 0143
[3] Chemistry - A European Journal, 2014, vol. 20, # 51, p. 16858 - 16862
[4] Chemical Communications, 2015, vol. 51, # 54, p. 10907 - 10909
[5] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 7122 - 7130
[6] Patent: WO2015/173277, 2015, A1, . Location in patent: Page/Page column 34; 35; 39
[7] Patent: WO2015/173295, 2015, A1, . Location in patent: Page/Page column 37
[8] Patent: WO2015/173276, 2015, A1, . Location in patent: Page/Page column 30
[9] Patent: WO2016/180775, 2016, A1, . Location in patent: Page/Page column 34
[10] Chemical Science, 2017, vol. 8, # 2, p. 1463 - 1468
[11] Patent: WO2017/178282, 2017, A1, . Location in patent: Page/Page column 41; 42; 44
[12] ChemCatChem, 2017, vol. 9, # 12, p. 2269 - 2274
[13] Organometallics, 2018, vol. 37, # 20, p. 3573 - 3580
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Reference: [1] Patent: US2007/219390, 2007, A1, . Location in patent: Page/Page column 10-11
[2] Patent: US2007/219390, 2007, A1, . Location in patent: Page/Page column 11
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Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 44, p. 14017 - 14025
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Reference: [1] Chemical Communications, 2015, vol. 51, # 54, p. 10907 - 10909
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Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 44, p. 14017 - 14025
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Reference: [1] Russian Journal of Applied Chemistry, 1998, vol. 71, # 9, p. 1611 - 1614
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