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2,2-Bis(hydroxymethyl)butyric acid is a chemical substance with the molecular formula C6H12O4, which is white crystal. Soluble in water, methanol, acetone, etc. It contains multiple functional groups and has similar chemical properties with dihydroxymethylbutyric acid. There are two hydroxymethyl groups attached to a quaternary carbon atom, and the four groups and the quaternary carbon atoms form a covalent structure similar to diamond in space, which determines the relative stability; The hydroxyl and carboxyl groups are reactive functional groups, which make the molecule have the characteristics of both alcohols and acids. The lipophilic carbon skeleton and hydrophilic functional group structure make it have unique solubility and become an excellent cross-linking agent and organic intermediate, which can be widely used in water-soluble polyurethane, polyester, epoxy resin, cross-linking agent and other aspects.
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Chemical Formula |
C6H12O4 |
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Exact Mass |
148 |
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Molecular Weight |
148 |
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m/z |
148 (100.0%), 149 (6.5%) |
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Elemental Analysis |
C, 48.64; H, 8.16; O, 43.19 |
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2,2-dihydroxymethylbutyric acid (DMBA) is a white crystal with the molecular formula C6H12O4, containing two primary hydroxyl groups and one carboxyl group in its molecular structure, possessing the characteristics of both alcohol and acid compounds. This multifunctional property makes it a core raw material in the field of water-based polymer materials, especially in the context of stricter environmental policies and the trend of water-based materials replacing oil-based materials, its application value is increasingly prominent.
DMBA is a key raw material in the manufacturing of waterborne polyurethane, and its core advantage lies in the ability to achieve self emulsification without the need for organic solvents. Traditional chain extender DMPA has a high melting point (180 ℃ -185 ℃) and relies on high boiling point solvents such as N-methylpyrrolidone (NMP) to assist in dissolution, resulting in high energy consumption and high risk of organic residue. DMBA has a low melting point (108 ℃ -115 ℃) and can be directly dissolved in polyols. The reaction is complete and does not require desolvation, significantly reducing production energy consumption and safety hazards.
The methylene group (- CH ₂ -) in its molecular structure increases the spatial distance between carboxyl groups and isocyanates, leading to a threefold increase in reaction rate (reducing the reaction time of the prepolymer from 150-180 minutes to 50-60 minutes). The waterborne polyurethane lotion prepared with DMBA as chain extender has a finer particle size (average particle size<100nm) and narrower distribution (PDI<0.2). The tensile strength of the adhesive film is increased by 20% -30%, the elongation at break is increased by 15% -25%, and the gloss is increased by 10% -15%. Its comprehensive performance is better than that of DMPA based products.
The application of DMBA in the field of adhesives includes epoxy resins, unsaturated polyester resins, and polyurethane adhesives. Its dihydroxy structure can undergo cross-linking reaction with carboxyl or epoxy groups in the resin, forming a three-dimensional network structure, significantly improving the water resistance, drug resistance, and thermal stability of the adhesive. For example, in fiberglass manufacturing, the temperature resistance of DMBA based adhesives has been increased from 120 ℃ to 180 ℃, and their acid and alkali corrosion resistance (pH 2-12) is better than traditional products.
In the field of coatings, DMBA as an additive can improve the leveling and adhesion of coatings. Its carboxyl group can chelate with metal ions to form stable complexes, preventing the coating from layering and precipitating during storage. Experimental data shows that the addition of 0.5% DMBA to water-based epoxy coatings extends storage stability from 3 months to 12 months, and the coating hardness (pencil hardness ≥ 3H) and impact resistance (50kg · cm) meet industry standards.
Traditional leather finishing agents are mainly water-based polyacrylic esters, which have problems such as poor water resistance and susceptibility to yellowing. DMBA based waterborne polyurethane leather coating agent introduces hydrophilic carboxyl groups into the hard segment structure through molecular design, making the coating both flexible and water-resistant. Leather treated with DMBA has a dry rub fastness (≥ level 4) and wet rub fastness (≥ level 3) that are superior to national standards, and maintains flexibility at low temperatures of -20 ℃. It is suitable for high-end leather products such as outdoor equipment and car seats.
Organic synthesis: green chemical intermediates
The hydroxyl and carboxyl groups of DMBA can participate in various organic reactions, such as:
Esterification reaction: Condensation with alcohols under acidic conditions to produce ester derivatives, which are used for synthesizing fragrances and plastic plasticizers;
Cyclic condensation: Under the action of acyl chloride, lactone products are generated, which are used as pharmaceutical intermediates for the synthesis of antibiotics and anti-inflammatory drugs;
Aggregation reaction: Participate as a comonomer in the synthesis of water-soluble polymer materials, such as sodium polyacrylate and polyvinyl alcohol derivatives.
DMBA acts as a chain extender in room temperature vulcanized silicone rubber, which can adjust the crosslinking density and mechanical properties of silicone rubber. Adding 2% DMBA silicone rubber increased the tensile strength from 0.8MPa to 1.5MPa, the elongation at break from 300% to 500%, and the vulcanization time was shortened to one-third of the traditional formula. In addition, DMBA can also be used in the manufacturing of composite materials such as artificial marble and fiberglass. By crosslinking with unsaturated polyester resin, the impact resistance and weather resistance of the materials can be improved.
Preparation of 2,2-bis(hydroxymethyl)butyric acid:
Method 1:
Add 72g butyraldehyde and 60g polyformaldehyde into a 500mL three-mouth flask equipped with stirrer, reflux condenser and thermometer, start stirring and heating, preheat to 45 ℃, add 19.7g of 30% trimethyl glue aqueous solution, control the reaction temperature at 45~50 ℃, and react for 60min.
After the reaction, remove the catalyst and by-products by vacuum distillation at 60 ℃, add 113g hydrogen peroxide dropwise under the heating condition of 50 ℃, and then add 40g sodium hydroxide for neutralization after holding at 70 ℃ for 1 hour, remove the water by vacuum distillation, add an appropriate amount of ethanol, filter and remove the inorganic salt, adjust the pH of the mother liquor to 4 with sulfuric acid, and remove the ethanol to obtain 104.4g white crystal product of 2,2-dimethylolbutyric acid with purity of 99.5%, The yield was 70.5%.
Method 2:
A process method for continuous production of 2,2-dihydroxymethylbutyric acid using a microreactor includes the following steps:
S1. Measure a certain amount of formaldehyde, butyraldehyde and triethylamine with a metering pump and place them in the mixer for forced mixing, and then enter the micro-reactor for condensation reaction. The flow rates of triethylamine, formaldehyde and n-butyraldehyde are 250ml/min, 2000ml/min and 1100ml/min respectively. The flow rates of triethylamine, formaldehyde and n-butyraldehyde are 0.1m/s, the reaction temperature is 50 ℃, the pressure is 0.2MPa, and the reaction residence time is 70 seconds, The mixer is connected with three metering pumps and a micro-reactor. The materials of the mixer and micro-reactor can be any one or more of glass, stainless steel, resin and silicon carbide. The micro-reactor can be one or more in series. The micro-reactor is installed with a heat exchanger inside to obtain the reaction liquid mainly containing 2,2-dihydroxymethylbutyraldehyde;
S2. The reaction solution mainly containing 2,2-dihydroxymethylbutyraldehyde obtained from S1 is continuously distilled and concentrated through a thin film rotary evaporator, and the low-boiling matter is recycled and applied to obtain the concentrated solution of 2,2-dihydroxymethylbutyraldehyde;
S3. Then pump hydrogen peroxide into the micro-reactor containing the concentrated solution of dimethylol butyraldehyde through a metering pump for oxidation reaction. The flow rate of hydrogen peroxide for oxidation reaction is 1200 ml/min, the residence time is 360 seconds, and the pressure is 0.2 MPa to obtain the reaction solution of 2,2-bis(hydroxymethyl)butyric acid;
S4. Take the reaction solution of 2,2-dihydroxymethylbutyric acid obtained in S3 and put it in a concentration kettle for concentration to obtain the concentrated solution of 2,2-dihydroxymethylbutyric acid, and then extract the concentrated solution of 2,2-dihydroxymethylbutyric acid three times with methyl isobutyl ketone, triethylamine and hydrogen peroxide can be recovered by low boiling, and methyl isobutyl ketone can be recovered by solvent, combined with the extracted solution, concentrated at atmospheric pressure, and then refrigerated and cooled, The separated product is centrifugally dried to obtain qualified 2,2-dihydroxymethylbutyric acid product.
Method 3:
Preparation of activated carbon-supported alkali catalyst:
Add the activated carbon into 30% liquid alkali, stir for 24 hours, filter, dry the activated carbon, put it into a muffle furnace under the protection of nitrogen at 600 ℃, and activate for 5 hours, which is the catalyst.
Preparation of 2,2-dihydroxymethylbutyric acid:
Add 45g of formaldehyde, 72g of butyraldehyde and 3.6g of catalyst into the flask. After reaction at 50 ℃ for 10 hours, remove the catalyst by filtration. After the unreacted formaldehyde and butyraldehyde are evaporated, reduce to normal temperature. Add 72g of water, heat to 80 ℃, add 34g of hydrogen peroxide, react for 2 hours, evaporate the unreacted substances, and cool down to obtain white crystals, namely, 2,2-dimethylolbutyric acid.
Method 4:
(1) Add 1000kg of water into the condensation kettle, add 12kg of soda ash and 5kg of sodium hydroxide, add 650kg of formaldehyde after mixing, cool to 10-15 ℃, add 240kg of n-butyraldehyde dropwise, and maintain a constant temperature for 16 hours after dropwise addition;
(2) Pump to the oxidation kettle, add formic acid water and, adjust the PH value to 6-7, reduce the pressure and concentration vacuum to -0.085MPa, recover n-butyraldehyde in the second stage, use water for cooling in the first stage, and use brine for cooling in the second stage.
(3) When the temperature rises to 50 ℃, add 500Kg of hydrogen peroxide by dropping. After dropping, keep the temperature at 60~62 ℃ for 4 hours and 70~72 ℃ for 4 hours;
(4) Maintain a vacuum of -0.060MPa for concentration, add 200Kg of water every 2 hours, add a total of 600Kg of water for azeotropic removal of formic acid, and recover 50% of the total amount of formic acid water for neutralization of soda ash and sodium hydroxide.
(5) Concentrate until the water content is below 1.0%, and add 100Kg of dichloroethane as diluent.
(6) After cooling, centrifuge and recover dichloroethane from mother liquor at atmospheric pressure.
(7) Primary refining: put methanol and crude products in the ratio of 1.5 ∶ 1, filter to remove insoluble substances, concentrate the filtrate, cool and crystallize, and obtain a high-quality product after centrifugation. The mother liquor of primary refining is treated with methyl isobutyl ketone.
(8) Secondary refining: put primary refined products and water in a ratio of 2:1, and cool them to recrystallize. The second best product of Lixinde. Apply the secondary refining mother liquor.
(9) Drying: control the temperature of the drying room at 80 ℃, cool it in the drying room after passing the moisture detection, and then take it out for crushing and screening.
(10) Put the primary refining mother liquor and methyl isobutyl ketone in the proportion of 5:1, cool and crystallize, and recover the product - 2.2 - dihydroxymethyl butyric acid by centrifugation, and then refine it again.
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