3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid
2,2-Bis(hydroxymethyl)propionic acid
CAS: 4767-03-7
Molecular Formula: C5H10O4
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Names and Identifiers
| Name | 2,2-Bis(hydroxymethyl)propionic acid |
| Synonyms | DMPA DMPA(R) dihydroxypivalic acid DIMETHYLOLPROPIONIC ACID Dimethylolpropionic acid 2,2-DIMETHYLOLPROPIONIC ACID 2,2-Dimethylolpropionic acid 2,2-Dimethylol Propionic Acid 2,2-BIS(HYDROXYMETHYL)PROPIONIC ACID 2,2-Bis(hydroxymethyl)propionic acid 2,2-Bis(hydroxymethyl)propanoic acid 2,2-Bis(hydroxymethyl) propionic acid 2,2-DIMETHYLOL PROPIONIC ACID ( BIS DMPA ) 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate 3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid |
| CAS | 4767-03-7 |
| EINECS | 225-306-3 |
| InChI | InChI=1/C5H10O4/c1-5(2-6,3-7)4(8)9/h6-7H,2-3H2,1H3,(H,8,9)/p-1 |
| InChIKey | PTBDIHRZYDMNKB-UHFFFAOYSA-N |
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Physico-chemical Properties
| Molecular Formula | C5H10O4 |
| Molar Mass | 134.13 |
| Density | 0.84 |
| Melting Point | 189-191°C(lit.) |
| Boling Point | 167.23°C (rough estimate) |
| Flash Point | >150°C |
| Water Solubility | soluble |
| Solubility | Soluble in acetone (slightly),methanol,and water. Insoluble in benzene. |
| Vapor Presure | 7.26E-07mmHg at 25°C |
| Vapor Density | <1 (vs air) |
| Appearance | White crystal |
| Color | White |
| Merck | 14,3253 |
| BRN | 1756385 |
| PH | 2.6 (50g/l, H2O, 20℃) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Stability | Stable. Hygroscopic. |
| Sensitive | Hygroscopic |
| Refractive Index | 1.4240 (estimate) |
| MDL | MFCD00004199 |
| Physical and Chemical Properties | appearance tasteless, free-flowing white crystals |
| Use | For the preparation of polyurethane emulsion leather finishing agent, photosensitive resin, magnetic recording material and its adhesive |
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R36/37 - Irritating to eyes and respiratory system. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | UA2465265 |
| FLUKA BRAND F CODES | 3-9 |
| TSCA | Yes |
| HS Code | 29159000 |
| Hazard Note | Irritant |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Upstream Downstream Industry
| Raw Materials | Propionaldehyde |
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Reference
| Reference Show more | 1. Zhang Shuang, Zhang Zhicheng, supeng, Hao Haibin, Li Wanli. Factors affecting paste and viscosity of MDI waterborne polyurethane [J]. Polyester Industry, 2021,34(01):45-47. 2. Wen, Wen, et al. "Synthesis of a Hein-Schiff base compound and its antibacterial activity on cotton fabrics. Cellose 27 (2020): 7243-7254. 3. [IF = 2.153] Wen Wen et al." High Antibacterial effect of a Cotton Fabric Treated with Piperazinyl Schiff Base."Fibers And Polymers. 2021 Jul 21 |
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Chemical properties
Open Data Unverified Data
odorless, free-flowing white crystals. Easily soluble in water, methanol, dimethylformamide, etc., hardly soluble in acetone, benzene, toluene, etc. Melting point 175~185 ℃.
Last Update：2024-04-09 19:43:38
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Reference Information
Open Data Unverified Data
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Use | 2,2-dimethylol propionic acid (also known as dimethylol propionic acid, the same below), is an important intermediate in chemical production. It is a type of multifunctional compound and a very valuable chemical product. Used as an important raw material for coatings, adhesives, resins and other chemical products. Used as an important raw material for coatings, adhesives, resins and other chemical products. It can also be applied to leather materials, liquid crystals, inks, food additives and adhesive chemicals. It is used to prepare polyurethane water emulsion leather finishing agent, photosensitive resin, magnetic recording material and its adhesive, etc. Used to prepare polyurethane water emulsion leather finishing agent, photosensitive resin, magnetic recording material and its adhesive, etc. |
| Structure and properties | 2,2-dihydroxymethylpropionic acid was first synthesized in 1901. It has a neopentyl structure and connects a carboxyl group and two primary hydroxyl groups to the quaternary carbon atom. The neopentyl structure gives it good heat resistance and light stability. It can be used as a crosslinking agent, emulsifier, dispersant and curing agent, it is widely used in electrodeposition coatings, epoxy coatings, inks, chemical intermediates, photography and other fields; the two hydroxyl groups determine that it has typical glycol properties and can participate in polycondensation reactions. In the reaction, low-activity carboxyl groups can be preserved, making polymers have high hydrophilicity, and can also be used to make fuels and pesticides and synthesize their lipids and metal salt derivatives. |
| the preparation method of | 2,2-dihydroxypropionic acid is as follows: 980Kg of pure water is added into 3000L reactor, 16Kg of sodium hydroxide is loaded with activated carbon, 1000Kg of formaldehyde is added, 300Kg of n-propionaldehyde is added dropwise, and the constant temperature at 20-60 ℃ is 6-14h after dropwise addition; adding 10Kg of formic acid and neutralizing PH value between 6 and 7.2; transfer the material to the oxidation kettle, concentrate under reduced pressure in the oxidation kettle, and recover some unreacted formaldehyde; add 580Kg of hydrogen peroxide dropwise to the temperature, and perform a constant temperature of 60-90 ℃ for 6-10h after the dropwise addition; add 400Kg of water to 800Kg, and concentrate under reduced pressure; concentrate until the water content is between 5-8%, cool and crystallize, and centrifuge to obtain crude 2,2-dihydroxymethylpropionic acid. Filtration mother liquor is used for cyclic recrystallization; add 1000kg of water to 1000kg of crude product, raise the temperature to 50-60 ℃ under stirring, add a small amount of iron remover and about 5kg of activated carbon, filter after half an hour to remove activated carbon. Then concentrated at normal pressure to water content between 25wt%~ 30wt%, cooling crystallization, centrifugation, drying and sieving to obtain 2, 2-dihydroxymethylpropionic acid product. the crude mother liquor is re concentrated and then recrystallized, and the product is extracted again. The fine mother liquor is then concentrated, decolorized, crystallized, centrifuged and dried to recover the product again. The refined mother liquor is returned to crude mother liquor after re-recovery treatment. The crude mother liquor after re-extraction of the product is finally treated as wastewater. The mother liquor after each filtration was well treated, 2, 2-dihydroxymethylbutyric acid in the mother liquor was recovered, and the product yield was improved. |
| spontaneous combustion temperature | >300°C |
Last Update：2024-04-09 19:43:38
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - [Physical and Chemical Properties]]
Open Data Unverified Data
| melting point | 189-191 °C(lit.) |
| boiling point | 167.23°C (rough estimate) |
| density | 0.84 |
| vapor density | <1 (vs air) |
| refractive index | 1.4240 (estimate) |
| flash point | >150°C |
| storage conditions | Inert atmosphere,Room Temperature |
| solubility | H2O: soluble |
| morphology | Crystalline Powder |
| color | White |
| PH value | 2.6 (50g/l, H2O, 20℃) |
| water solubility | soluble |
| sensitivity | Hygroscopic |
| Merck | 14,3253 |
| BRN | 1756385 |
| stability | Stable. Hygroscopic. |
| InChIKey | PTBDIHRZYDMNKB-UHFFFAOYSA-N |
| NIST chemical information | 2,2-Bis(hydroxymethyl)propionic acid(4767-03-7) |
| EPA chemical information | Dimethylolpropionic acid (4767-03-7) |
Last Update：2024-04-09 19:43:38
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Uses and synthesis methods
Open Data Unverified Data
| use |
2, 2-dimethylol propionic acid (also known as dimethylol propionic acid, the same below), is an important intermediate in chemical production. It is a kind of multifunctional compound and a very valuable chemical product. |
| structure and performance | 2, 2-dihydroxymethylpropionic acid was first synthesized in 1901. It has a neopentyl structure. A carboxyl group and two primary hydroxyl groups are connected to the quaternary carbon atom. The neopentyl structure gives it good heat resistance and light stability. It can be used as a crosslinking agent, emulsifier, dispersant and curing agent. It is widely used in electrodeposition coatings, epoxy coatings, inks, chemical intermediates; the two hydroxyl groups determine that it has typical diol properties and can participate in the polycondensation reaction. In the reaction, the low-activity carboxyl group can be preserved, making the polymer highly hydrophilic, and it can also be used to make fuel and Insecticides and synthesize their lipids and metal salt derivatives. |
Last Update：2024-04-09 19:43:38
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Preparation
Open Data Unverified Data
The preparation method of 2, 2-dihydroxypropionic acid is as follows:
980Kg of pure water is added into 3000L reactor, 16Kg of sodium hydroxide is loaded with activated carbon, 1000Kg of formaldehyde is added, 300Kg of n-propionaldehyde is added dropwise, and the constant temperature at 20-60 ℃ is 6-14h after dropwise addition.
Add formic acid 10Kg and neutralize PH between 6 and 7.2;
Transfer to the oxidation kettle, concentrate under reduced pressure in the oxidation kettle, and recover part of the unreacted formaldehyde;
add 580Kg of hydrogen peroxide dropwise after heating, and perform a constant temperature of 60-90 ℃ for 6-10h after dropwise addition;
add 400Kg to 800Kg of water and concentrate under reduced pressure;
Concentrate until the moisture is between 5-8%, cool and crystallize, and centrifuge to obtain crude 2,2-dihydroxymethylpropionic acid. Filtered mother liquor for cyclic recrystallization;
add 1000kg of water to 1000kg of crude product, raise the temperature to 50-60 ℃ under stirring, add a small amount of iron remover and about 5kg of activated carbon, filter after half an hour to remove activated carbon. Then concentrated at normal pressure to water content between 25wt%~ 30wt%, cooling and crystallization, and then centrifuging, drying and sieving to obtain 2, 2-dihydroxymethylpropionic acid products.
crude mother liquor is reconcentrated and recrystallized to extract the product again. The fine mother liquor is then concentrated, decolorized, crystallized, centrifuged and dried to recover the product again. The refined mother liquor is returned to crude mother liquor after re-recovery. The crude mother liquor after re-extraction of the product is finally treated as wastewater. The mother liquor after each filtration was well treated, 2, 2-dihydroxymethylbutyric acid in the mother liquor was recovered, and the product yield was improved.
Last Update：2024-04-09 19:43:38
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Security information
Open Data Unverified Data
| dangerous goods mark | Xi |
| hazard category code | 36/37/38-36/37 |
| safety instructions | 26-37/39 |
| WGK Germany | 3 |
| RTECS number | UA2465265 |
| F | 3-9 |
| auto-ignition temperature | >300 °C |
| Hazard Note | Irritant |
| TSCA | Yes |
| customs code | 29159000 |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
Last Update：2024-04-09 19:43:38
3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid - Use
Open Data Unverified Data
Important raw materials for chemical products such as coatings, adhesives, and resins. It can also be applied to leather materials, liquid crystals, inks, food additives and adhesive chemicals. It is used to prepare polyurethane water emulsion leather finishing agent, photosensitive resin, magnetic recording material and its adhesive, etc. It is used to prepare polyurethane water emulsion leather finishing agent, photosensitive resin, magnetic recording material and its adhesive, etc.
Last Update：2024-04-09 19:43:38
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Raw Materials for 3-Hydroxy-2-(hydroxymethyl)-2-methyl-propanoic acid