Nickel(II) acetylacetonate
Nickel(II) acetylacetonate
CAS: 3264-82-2
Molecular Formula: C10H14NiO4
Nickel(II) acetylacetonate - Names and Identifiers
Nickel(II) acetylacetonate - Physico-chemical Properties
| Molecular Formula | C10H14NiO4 |
| Molar Mass | 256.91 |
| Density | 0,145 g/cm3 |
| Melting Point | 230°C (dec.)(lit.) |
| Boling Point | 220 °C (11 mmHg) |
| Flash Point | >200°C |
| Water Solubility | soluble |
| Solubility | 4.8g/l |
| Vapor Presure | 2.7 hPa (110 °C) |
| Appearance | Liquid |
| Specific Gravity | 1.455 |
| Color | Clear pale yellow |
| Exposure Limit | NIOSH: IDLH 10 mg/m3; TWA 0.015 mg/m3 |
| Merck | 14,6500 |
| BRN | 4157970 |
| Storage Condition | Store below +30°C. |
| Stability | hygroscopic |
| Sensitive | Hygroscopic |
| Refractive Index | 1.57-1.64 |
| Physical and Chemical Properties | Light green orthorhombic crystal. Relative density (17 C) 1.455. Boiling point 220~235 degrees C (14.67kPa). Insoluble in ether, petroleum, soluble in water, ethanol, chloroform and benzene. In the solid state is present in the form of a trimer, while in the vapor as a single molecule. |
Nickel(II) acetylacetonate - Risk and Safety
| Risk Codes | R49 - May cause cancer by inhalation R22 - Harmful if swallowed R43 - May cause sensitization by skin contact R40 - Limited evidence of a carcinogenic effect |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 3 |
| RTECS | SA2100000 |
| TSCA | Yes |
| HS Code | 29420000 |
| Toxicity | LD50 orally in Rabbit: 587 mg/kg |
Nickel(II) acetylacetonate - Reference Information
| LogP | 0.4 at 20℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | nickel acetylacetonate is a light green orthorhombic crystal, also known as di (acetylacetonate) dihydrate coordination nickel, 2, 4-pentanedione dihydrate nickel. Blue-green orthorhombic crystal system crystals. Slightly soluble in water and methanol, soluble in ethanol. In the warm toluene, it is boiling and dehydrated to produce nickel acetylacetonate anhydrous. When heated to 100 ℃ under vacuum, it is also dehydrated into light green anhydrous. |
| Application | Acetylacetonate Ni(acac)2 can be used to catalyze oligomerization, hydrosilicidation, hydrogenation, reduction, cross coupling, oxidation, and conjugation Addition, addition to unsaturated bonds, and rearrangement and many other types of reactions. |
| Mechanism of action | Nickel acetylacetonate Ni(acac)2 can realize the oligomerization and coupling of olefins, but it does not have strong catalytic activity. Usually, it is necessary to add Lewis acid and suitable ligands to obtain a highly active catalytic system. The added Lewis acids include aluminum alkyl, lithium butyl and sodium borohydride, which are mainly used to reduce Ni(II) salts and form active precursor Ni-H bonds in situ through β-H elimination process. Then the insertion of alkynes to it forms a Ni-C bond, and then the insertion of another molecule of alkene to the Ni-C bond occurs, and finally the Ni-H bond catalytic precursor is obtained again after reduction and elimination, accompanied by the corresponding oligomerization product. |
| Preparation method | A new preparation method of nickel acetylacetonate with convenient operation, simple preparation process and high product yield. The specific preparation method is as follows: a. Soluble nickel salt is dissolved in deionized water in a reactor with jacket and stirring device to prepare a solution with a nickel salt concentration of 10-20wt%, and NaOH is dissolved in water to prepare an alkali solution with a concentration of 5-15wt%. The alkali solution is added to the nickel salt solution at room temperature and under severe stirring to make the pH value of the reaction mixture 7-10, and blue-green nickel hydroxide is generated in the process. The soluble nickel salt used in the reaction is crystalline nickel chloride (NiCl2 · 6H2O) or crystalline nickel nitrate (Ni(NO3)2 · 6H2O). B. Based on the amount of nickel hydroxide precipitate generated in step A, acetylacetone, which is 1 to 5 times more excess according to the chemical reaction measurement ratio, is added to the above reaction mixture, heated to the reflux temperature and refluxed for 5 to 15h at the stirring speed of 600 to 2500 r/min, and light blue nickel acetylacetonate crystals are formed in the process. C. After cooling, the reaction mixture is pumped out, the precipitate is washed with deionized water, and the product is vacuum dried at 40 ℃. The amount of crystal water in nickel acetylacetonate crystal was determined by the weight loss in the first stage on the thermogravimetric (TG) curve. Combined with the analysis results of total carbon content and X-ray fluorescence spectrum, the chemical formula of the product was determined to be Ni(CH3COCHCOCH3)2 · 2H2O. |
| Use | Organic synthesis catalyst Catalyst for organic reactions. |
| Production method | 1. Anhydrous nickel acetylacetonate is obtained by dehydration reaction and vacuum sublimation of nickel acetylacetonate dihydrate, or constant boiling distillation with toluene. 2. Nickel acetylacetonate dihydrate was heated at 100 ℃ for 4h in Abdelhadden dryer and dehydrated and dried at 133.322Pa. If necessary, it can be sublimated and purified at 170~210 ℃ and 26.6644 ~ 53.3288Pa pressure. 3. Through the direct reaction of nickel chloride and acetylacetone. |
Last Update：2024-04-10 22:41:03
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