Structure of 7446-81-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Alley, Katelyn R ; Wyatt, Katelyn M ; Fries, Adam C ; DeRose, Victoria J ;
Abstract: The nucleolus, a membraneless organelle crucial for ribosome production, has a unique nanoscale structure whose organization is responsive to cell signals and disease progression. Here, we highlight the potential of Expansion Microscopy (ExM) for capturing intricate spatial and functional information about membraneless organelles such as the nucleolus and nuclear foci. We apply dual protein Expansion Microscopy (dual-proExM) in combination with click Expansion Microscopy (click-ExM) to capture images at the highest resolution reported for the nucleolus of ∼45 ± 2 nm. Inhibition of nucleolar processes triggers a nucleolar stress response, causing distinct structural rearrange_x005f_x0002_ments whose molecular basis is an area of active investigation. We investigate time-dependent changes in nucleolar structure and function under nucleolar stress induced by oxaliplatin, actinomycin D, and other platinum-based compounds. Our findings reveal new stages that occur prior to the complete sequestration of RNA Pol I into nucleolar caps, shedding light on the early mechanisms of the nucleolar stress response. RNA transcription is linked to nanoscale protein rearrangements using a combination of click-ExM and pro-ExM, revealing locations of active transcripts during the early stages of nucleolar stress reorganization. With prolonged stress, fibrillarin and NPM1 segregate from the nucleolus into nucleoplasmic foci that are for the first time imaged at nanometer resolution. In addition to revealing new morphological information about the nucleolus, this study demonstrates the potential of ExM for imaging membraneless organelles with nanometer-scale precision.
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Selectively Detachable Hydrogel Adhesion Enabled by Stimulus-Specific Cleavable Cross-Linkers
Yoon, Young Bin ; Cho, In ; Koo, Hye Been ; Jung, Hoeyun ; Chang, Jae-Byum ;
Abstract: The development of detachable hydrogel adhesion presents an advancement in the fields of soft electronics and bioengineering as it offers additional functionalities to these applications. However, conventional methods typically rely on a single detachment trigger, so it is unclear whether unintentional detachment might occur in the specific environments of other detachment systems. This makes it difficult to directly introduce two independent detachment triggers directly. In this article, we present a strategy for selective detachable adhesion based on two types of cleavable cross-linkers, N,N'-bis(acryloyl)cystamine(BAC) and N,N′-(1,2-dihydroxyethylene)bis(acrylamide)(DHEBA), each with an independent cleavage trigger. BAC can be cleaved through the reduction of disulfide bonds using reducing agents, while DHEBA can be hydrolyzed through heating. We constructed stitching polymer networks for topological adhesion using two types of cleavable cross-linkers, allowing the networks to be selectively degraded depending on which cross-linker was used. Our findings show that the use of cleavable cross-linkers achieved selectively detachable adhesion in various hydrogels, with adhesion energy that reached up to 1223 J m−2 in polyacrylamide-alginate (PAAm-alginate) tough hydrogel. This strategy also proved versatile as it led to effective adhesion with various substrates, including aluminum, copper, glass, and polyester film (PET). Furthermore, we took advantage of the high programmability of this approach to construct hydrogel-based YES and AND logic gates, whose output changed depending on the applied input triggers. In addition, we designed a selective-release capsule model capable of dual-solution release, which emphasizes the potential of our strategy in creating programmable and responsive soft materials.
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Keywords: hydrogel ; detachable hydrogel adhesion ; cleavable cross-linker ; hydrogel logic gates ; selective-release capsule
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Hye Been Koo ; Eunseok Heo ; In Cho ; Sun Hong Kim ; Jiheong Kang ; Jae-Byum Chang
Abstract: Human hands are highly versatile. Even though they are primarily made of materials with high water content, they exhibit a high load capacity. However, existing hydrogel grippers do not possess a high load capacity due to their innate softness and mechanical strength. This work demonstrates a human hand-inspired all-hydrogel gripper that can bear more than 47.6 times its own weight. This gripper is made of two hydrogels: poly(methacrylamide-co-methacrylic acid) (P(MAAm-co-MAAc)) and poly(N-isopropylacrylamide) (PNIPAM). P(MAAm-co-MAAc) is extremely stiff but becomes soft above its transition temperature. By taking advantage of the difference in the kinetics of the stiff–soft transition of P(MAAm-co-MAAc) hydrogels and the swelling–shrinking transition of PNIPAM hydrogels, this gripper can be switched between its stiff-bent and stiff-stretched states by simply changing the temperature. The assembly of these two hydrogels into a gripper necessitated the development of a new hydrogel adhesion method, as existing topological adhesion methods are not applicable to such stiff hydrogels. A new hydrogel adhesion method, termed split-brushing adhesion, has been demonstrated to satisfy this need. When applied to P(MAAm-co-MAAc) hydrogels, this method achieves an adhesion energy of 1221.6 J m[−2], which is 67.5 times higher than that achieved with other topological adhesion methods.
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Dae-Hyeon Song ; Chang Woo Song ; Jinkyoung Chung ; Eun-Hae Jang ; Hyunwoo Kim ; Yongsuk Hur , et al.
Abstract: In biological studies and diagnoses, brightfield (BF), fluorescence, and electron microscopy (EM) are used to image biomolecules inside cells. When compared, their relative advantages and disadvantages are obvious. BF microscopy is the most accessible of the three, but its resolution is limited to a few microns. EM provides a nanoscale resolution, but sample preparation is time-consuming. In this study, we present a new imaging technique, which we termed decoration microscopy (DecoM), and quantitative investigations to address the aforementioned issues in EM and BF microscopy. For molecular-specific EM imaging, DecoM labels proteins inside cells using antibodies bearing 1.4 nm gold nanoparticles (AuNPs) and grows silver layers on the AuNPs' surfaces. The cells are then dried without buffer exchange and imaged using scanning electron microscopy (SEM). Structures labeled with silver-grown AuNPs are clearly visible on SEM, even they are covered with lipid membranes. Using stochastic optical reconstruction microscopy, we show that the drying process causes negligible distortion of structures and that less structural deformation could be achieved through simple buffer exchange to hexamethyldisilazane. Using DecoM, we visualize the nanoscale alterations in microtubules by microtubule-severing proteins that cannot be observed with diffraction-limited fluorescence microscopy. We then combine DecoM with expansion microscopy to enable sub-micron resolution BF microscopy imaging. We first show that silver-grown AuNPs strongly absorb white light, and the structures labeled with them are clearly visible on BF microscopy. We then show that the application of AuNPs and silver development must follow expansion to visualize the labeled proteins clearly with sub-micron resolution.
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Lee, Wonseok ; Heo, Eunseok ; Koo, Hye Been ; Cho, In ; Chang, Jae-Byum ;
Abstract: Achieving strong adhesion between hydrogels and diverse materials is greatly significant for emerging technologies yet remains challenging. Existing methods using non-covalent bonds have limited pH and ion stability, while those using covalent bonds typically lack on-demand detachment capability, limiting their applications. In this study, a general strategy of covalent bond-based and detachable adhesion by incorporating amine-rich proteins in various hydrogels and inducing the interfacial crosslinking of the hydrogels using a protein-crosslinking agent is demonstrated. The protein crosslink offers topol. adhesion and can reach a strong adhesion energy of ≈750 J m-2. The chem. of the adhesion is characterized and that the inclusion of proteins inside the hydrogels does not alter the hydrogels' properties is shown. The adhesion remains intact after treating the adhered hydrogels with various pH solutions and ions, even at an elevated temperature The detachment is triggered by treating proteinase solution at the bonding front, causing the digestion of proteins, thus breaking up the interfacial crosslink network. In addition, that this approach can be used to adhere hydrogels to diverse dry surfaces, including glass, elastomers and plastics, is shown. The stable chem. of protein crosslinks opens the door for various applications in a wide range of chem. environments.
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Keywords: covalent adhesion ; detachable adhesion ; hydrogels ; otein crosslinks
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Haeseong Im ; Eunseok Heo ; Dae-Hyeon Song ; Jeongwon Park ; Hyeonbin Park ; Kibum Kang , et al.
Abstract: Curved hydrogel surfaces bearing chemical patterns are highly desirable in various applications, including artificial blood vessels, wearable electronics, and soft robotics. However, previous studies on the fabrication of chemical patterns on hydrogels employed two-photon lithography, which is still not widely accessible to most laboratories. This work demonstrates a new patterning technique for fabricating curved hydrogels with chemical patterns on their surfaces without two-photon microscopy. In this work, we show that exposing hydrogels in fluorophore solutions to single photons via confocal microscopy enables the patterning of fluorophores on hydrogels. By applying this technique to highly stretchable hydrogels, we demonstrate three applications: (1) improving pattern resolution by fabricating patterns on stretched hydrogels and then returning the hydrogels to their initial, unstretched length; (2) modifying the local stretchability of hydrogels at a microscale resolution; and (3) fabricating perfusable microchannels with chemical patterns by winding chemically patterned hydrogels around a template, embedding the hydrogels in a second hydrogel, and then removing the template. The patterning method demonstrated in this work may facilitate a better mimicking of the physicochemical properties of organs in tissue engineering and may be used to make hydrogel robots with specific chemical functionalities.
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CAS No. : | 7446-81-3 |
Formula : | C3H3NaO2 |
M.W : | 94.04 |
SMILES Code : | C=CC([O-])=O.[Na+] |
MDL No. : | MFCD00067207 |
InChI Key : | NNMHYFLPFNGQFZ-UHFFFAOYSA-M |
Pubchem ID : | 4068533 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H315-H318-H335-H410 |
Precautionary Statements: | P261-P305+P351+P338-P273 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
Num. heavy atoms | 6 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 15.89 |
TPSA ? Topological Polar Surface Area: Calculated from |
40.13 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
-5.59 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.35 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.08 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.08 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.23 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-1.32 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.58 |
Solubility | 24.9 mg/ml ; 0.264 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.76 |
Solubility | 16.5 mg/ml ; 0.175 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
0.44 |
Solubility | 259.0 mg/ml ; 2.75 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.63 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.27 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Using reverse microemulsion techniques, nanoarticles were made with APMA containing free amines that can react with the isothiocyanate moiety of the MeODOTA chelator and/or of fluorescein isothiocyanate (FITC). These APMA-containing articles (comprising IMMA/APMA/NaA in the ratio 14: 2: 1) were dissolved in 0.1 M bicarbonate buffer, pH 9.4 at 65 mg/mL. A two-fold excess of MeODOTA-NCS/HCI and 1 mg of FITC were added and allowed to react for 1.5 hours. Unreacted MeODOTA and FITC were removed by size exclusion chromatography (PD-10 column equilibrated with water). One equivalent of gadolinium chloride (GdCl3) was added directly to the DOTA-containing articles in water and was allowed to chelate for 4 hours at 50°C. Unchelated gadolinium was removed by size exclusion chromatography. The FITC-labeled Gd-DOTA-containing articles were lyophilized to quantitate yield. Ligand attachment, if desired, follows. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.0%Chromat. | Aliquat 336; sodium iodide; In water; at 50℃; for 2.5h; | In Example 8, benzyl acrylate was prepared by dissolving <strong>[7446-81-3]sodium acrylate</strong> (10 mmoles = 0.95 g) in water (101.3 g). The reaction flask was immersed in the water bath at 50°C and magnetically stirred. Then, a mixture consisting of benzyl chloride (50 mmoles = 6.29 g), Aliquat 336 (2 mmoles = 0.85 g), and sodium iodide (2 mmoles = 0.30 g) was added to the water phase. The reaction mixture was stirred magnetically at 50°C. The reaction mixture after 150 minutes consisted of benzyl acrylate in a 85.0percent theoretical yield based on <strong>[7446-81-3]sodium acrylate</strong>. Analysis was done with an external standard of Durene (tetramethylbenzene) on a Gas Chromatograph. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59.0%Chromat. | With 2,6-di-tert-butyl-4-methyl-phenol; hydroquinone;Aliquat 336; In water; at 69℃; for 3h; | In Example 3, butyl acrylate was prepared by dissolving <strong>[7446-81-3]sodium acrylate</strong> (30 mmoles = 2. 82 g) in water (300.04 g) in a three neck flask for 500 mL. The reaction flask was immersed in the water bath at 70. 5°C and stirred mechanically (about 600 rpm). Then, a mixture consisting of butyl bromide (120 mmoles = 16.46 g), Aliquat 336 (3 mmoles = 1.30 g), durene (chromatographic standard, 5 mmoles = 0.67 g) and traces of hydroquinone and DTBMP (2,6-di-t-butyl-4- methylphenol, to prevent polymerization) was added to the water phase. The reaction mixture was stirred mechanically at 69°C (measured inside the flask) at the rate of about 620 rpm (measured periodically). Aliquots of the organic (lower) phase were taken after 0,10, 30,60, 120 and 180 minutes from the time of mixing the phases. The organic reaction mixture after 180 minutes consisted of 29.1 percent of unreacted butyl bromide by GC. The theoretical yield of butyl acrylate based on limiting reactant <strong>[7446-81-3]sodium acrylate</strong> was 59.0percent. Analysis was done with an internal standard of Durene (tetramethylbenzene) on a Gas Chromatograph. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | Example 21 Making a Compound I from Method B 6.123 g (0.0651 mol) <strong>[7446-81-3]sodium acrylate</strong> is dissolved to 25 mL THF and cooled to -70° C. 12.8 mL (0.0651 mol, 12.938 g) chlorotriethoxysilane in THF (15 mL) is added dropwise to reaction solution. The solution is stirred for over night allowing it to warm up to room temperature. NaCl is removed by filtration and solution evaporated to dryness to result clear liquid, acryltriethoxysilane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 4 Synthesis of Bis(trimethylsilyl)methylacrylate Bis(trimethylsilyl)chloromethane (Aldrich) 39 g, 0.2 mole), <strong>[7446-81-3]sodium acrylate</strong> (28 g, 0.3 mole), Adogen 464 (Aldrich) (6.96 g), and phenothiazine (0.10 grams) were placed in a round bottom flask equipped with a condenser, mechanical stirrer and a nitrogen inlet. The flask was charged with 100 ml of butyronitrile and heated to reflux while stirring. After 6 hours, the mixture was diluted with 150 ml hexanes and filtered to remove the solids. The solvents were removed under reduced pressure. Fractional distillation of the residue under reduced pressure gave 35.5 grams 975percent) of the desired product at 45-58° C. at 0.5 mm pressure. |
Yield | Reaction Conditions | Operation 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 (96.8% 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 0.666667h; | 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 95% yield. |
With sodium hydroxide; In chlorobenzene; | EXAMPLE 1 Preparation of Pentabromobenzyl acrylate To a 500 ml three-necked flask equipped with mechanical stirrer, thermometer and a condenser there are added 290 ml of chlorobenzene, 8.3 gr. NaOH (0.21 mole), and 15 gr. acrylic acid (0.21 mole) were added in small portions. The mixture was heated during 30 minutes at 30-50 C., to give the sodium salt of acrylic acid. |
With sodium hydroxide; In water; | Example 1 Approximately 31.96 parts of acrylic acid (BASF) are slowly dissolved, with stirring in approximately 25.02 parts of water. To the cooled solution is slowly added, with stirring and cooling, approximately 3.55 parts of 50% sodium hydroxide (NaOH; Aldrich), which is sufficient to convert approximately 10 mole % of the acrylic acid to sodium acrylate. | |
With sodium hydroxide; In water; | Example 5 The procedure described in Example 3 is followed except that approximately 24.88 parts of acrylic acid are dissolved in approximately 13.54 parts of water. Approximately 13.82 parts of 50% NaOH is added, which is sufficient to convert approximately 50 mole % of the acrylic acid to sodium acrylate. Approximately 47.84 parts of glycerol are added. | |
With sodium hydroxide; In water; at 15 - 69℃;Product distribution / selectivity; | For Examples 1 to 6, an apparatus as described in FIG. 1 was assumed. For the calculation, the diameter of the ring line R was set at 20 cm, the diameter of the feeds Z1 to Z3 each at 5 cm, the mass flow rate in the ring line R before feed Z3 at 349 t/h, the temperature of the mass flow rate in ring line R before feed Z3 at 26 C., the distance between feed Z3 and feed Z1 at 20 cm, the distance between feed Z1 and feed Z2 at 20 cm, the mass flow rate of acrylic acid at 11.5 t/h, the mass flow rate of 50% by weight sodium hydroxide solution at 8.4 t/h and the mass flow rate of water at 5 t/h.Examples 1 to 3 demonstrate the influence of the metering sequence.In Examples 4 to 6, sodium hydroxide solution and water are premixed. In Examples 5 and 6, the calculation was additionally supplemented by cooling of the sodium hydroxide solution/water mixture to the temperature specified before entry into the ring line R.The examples demonstrate how the peak temperature can be influenced via the metering sequence; Examples 7 to 9 were calculated analogously to Examples 1 to 6.For the calculation of Examples 7 to 9, it was assumed that an NaOH/H2O mixture and acrylic acid are metered into a common Venturi tube. The length of the Venturi tube was set at 93.2 cm, the Venturi tube narrowing to a diameter of 10 cm over a distance of 8.4 cm, retaining the diameter of 10 cm over a distance of 27.6 cm and widening again to a diameter of 20 cm over a distance of 57 cm. The distance of the feed Z1 from the point where the Venturi tube has narrowed to 10 cm was assumed to be 5 cm, the distance of feed Z2 from feed Z1 to be 8 cm and the diameter of the two feeds Z1 and Z2 in each case to be 3.5 cm. The two feeds Z1 and Z2 in each case are arranged opposite one another, the connecting axis of the two feeds Z1 being rotated by 90 relative to the connecting axis of the two feeds Z2.In Examples 7 to 9, the influence of the mass flow rate in the ring line R was additionally examined. In Examples 8 and 9, the mass flow rate in the ring line R was therefore reduced by 50% and 90% respectively in the calculation; The calculations also demonstrate the advantages of the Venturi tube over simple metering (comparison of Examples 6 and 7). | |
With sodium hydroxide; In water; at 40℃; | Configuration of sodium acrylate solution:181.5 g of acrylic acid was slowly added to an aqueous solution of sodium hydroxide (104 g, 32percent).Stirring at the same time, the temperature is controlled below 40 °C,Formulated as a sodium acrylate solution. |