Structure of 2,4,6-Triisopropylphenol
CAS No.: 2934-07-8
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CAS No. : | 2934-07-8 |
Formula : | C15H24O |
M.W : | 220.35 |
SMILES Code : | OC1=C(C(C)C)C=C(C(C)C)C=C1C(C)C |
MDL No. : | MFCD19302639 |
* 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 |
---|---|---|
Example 9Unless otherwise indicated, the reactants were added to the reactor under constant agitation and the reactor's content remained under this agitation until recovery of the alkylated triaryl phosphate ester began.A 246 g sample of the material described in Table 5, above, was combined with 800 g (5.22 mole) of POCl3 and 2.56 grams (0.46 mole %) of tetrabutyl ammonium bromide. The mixture was heated to 114 C. and refluxed at that temperature until evolution of HCl slowed. The temperature was gradually increased to 135 C. and held at that temperature until HCl evolution ceased. The excess POCl3 was recovered in vacuo stripping to an end point of 135 C. and <1.0 mmHg.The reactor was allowed to cool and then charged with 2.96 g of MgCl2 (1.8 mole %) and heated to 110 C. 622.5 g (6.61 moles) of Phenol (99.6%) was fed to the reactor while gradually and simultaneously increasing the temperature of the reactor's content from 110 to 135 C. over a 3-hour period. Within one hour after the completion of the feed, P-31 NMR analysis indicated complete conversion of the monoaryl dichlorophosphate to triaryl phosphates. The pressure was reduced to 10 mmHg and unreacted phenol partially removed overhead at 140 C.The alkylated triaryl phosphate ester was recovered from the reactor and analyzed, and the alkylated triaryl phosphate ester was found to have the characteristics outlined in Table 9, below. Normalized or relative weight percents are based on the total weight of phenol and the alkylated triaryl phosphate ester as is indicated in the table. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 5Unless otherwise indicated, the reactants were added to the reactor under constant agitation and the reactor's content remained under this agitation until recovery of the alkylated phenyl phosphate began. A 150 g charge of the mixture (1.1 mole of reactive isopropylated phenols prepared via ortho alkylation of phenol with propylene and AlCl3), described in Table 4 below was combined with 640 g (4.17 mole) of POCl3 and 1.5 grams of tetrabutyl ammonium bromide in a reactor. The mixture was heated under constant agitation to about 114 C. and refluxed at that temperature until evolution of HCl ceased, thus indicating the formation of the intermediate product. Excess POCl3 was recovered from the intermediate product (95% of theoretical amount) by first heating it at atmospheric pressure to about 130 C. and then heating it to about 135 C. at 1 mmHg. Heating of the reactor's content was discontinued, the reactor's content allowed to cool, and the reactor charged with 0.3 g of MgCl2 and 188 g of phenol (2.0 mole, 99.6%).After the addition of the MgCl2 and phenol, the temperature of the reactor's content was increased to about 110 C., and the reaction mixture in the reactor was then heated from about 110 to about 130 C. over a period of about 3 hours under agitation. 31P-NMR indicated complete conversion of the mono aryl dichlorophosphate and about a 55/45 mixture of the diaryl to triaryl intermediate and the alkylated triaryl phosphate ester product.An additional 0.9 g of MgCl2 was then added to the reactor and the reaction was conducted for an additional 4 hours, during which moderate HCl evolution was observed, until HCl evolution ceased. After HCl evolution ceased, 12.00 g of fresh phenol (0.13 mole, 99.6%) was charged to the reactor and the reaction was run with a nitrogen sparge at 130 C. until complete (about 2 hrs). Pressure was reduced to 10 mmHg and unreacted phenol removed overhead at 130 C. The alkylated triaryl phosphate ester thus produced was analyzed, and the alkylated triaryl phosphate ester was found to have the characteristics outlined in Table 5, below. Normalized, or relative weight percents, are based on the total weight of phenol and the alkylated triaryl phosphate ester as is indicated in the table. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With molybdenum(VI) oxide; In ethanol; at 280℃; for 4h;Inert atmosphere; | General procedure: 2.0 g of guaiac acid (purchased in Tianjin Guangfu Technology Co., Ltd.), 0.5 g of MOS catalyst and 100 ml of ethanol were placed in a 300 ml reaction vessel, and the air in the reaction vessel was replaced with nitrogen. The temperature was raised to 280 C, and the reaction was stirred for 4 h. After the reaction was completed, the mixture was filtered under suction and rotary evaporated. The liquid product was subjected to qualitative analysis on a gas chromatography-mass spectrometer (GC6890-MS5973, Agilent), and the internal standard was added. Quantitative analysis by gas chromatography. The chromatogram was performed on an HP-5ms, 30m X 0.25mm X 0.25mum capillary column. The conversion of the raw guaiacol is calculated by (initial guaiacol moles - residual guaiacol moles) / (initial guaiacol moles) X100%, and the selectivity of the product hydrocarbyl phenol is (hydrocarbyl phenol) The number of moles / (molar guaiacol moles) X 100 % was calculated. Among the guaiacol conversion products, ethyl phenols include o-ethyl phenol, 2,5-diethyl phenol, 3,5-diethyl phenol, and propyl phenols include 2,6-diisopropyl phenol. , 2,4-diisopropylphenol, 2,4,6-triisopropylphenol, butyl phenols including 2,5-di-sec-butylphenol, 2,6-di-tert-butylphenol, 2, 4-di-tert-butylphenol, 2,6-di-tert-butyl-p-ethylphenol, pentanols include 2,4-di-tert-amylphenol, others include o-ethoxyphenol, o-ethoxybenzene Methyl ether, p-ethyl guaiacol, 2,6-diisopropylanisole). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With molybdenum(VI) oxide; In ethanol; at 280℃; for 4h;Inert atmosphere; | General procedure: 2.0 g of guaiac acid (purchased in Tianjin Guangfu Technology Co., Ltd.), 0.5 g of MOS catalyst and 100 ml of ethanol were placed in a 300 ml reaction vessel, and the air in the reaction vessel was replaced with nitrogen. The temperature was raised to 280 C, and the reaction was stirred for 4 h. After the reaction was completed, the mixture was filtered under suction and rotary evaporated. The liquid product was subjected to qualitative analysis on a gas chromatography-mass spectrometer (GC6890-MS5973, Agilent), and the internal standard was added. Quantitative analysis by gas chromatography. The chromatogram was performed on an HP-5ms, 30m X 0.25mm X 0.25mum capillary column. The conversion of the raw guaiacol is calculated by (initial guaiacol moles - residual guaiacol moles) / (initial guaiacol moles) X100%, and the selectivity of the product hydrocarbyl phenol is (hydrocarbyl phenol) The number of moles / (molar guaiacol moles) X 100 % was calculated. Among the guaiacol conversion products, ethyl phenols include o-ethyl phenol, 2,5-diethyl phenol, 3,5-diethyl phenol, and propyl phenols include 2,6-diisopropyl phenol. , 2,4-diisopropylphenol, 2,4,6-triisopropylphenol, butyl phenols including 2,5-di-sec-butylphenol, 2,6-di-tert-butylphenol, 2, 4-di-tert-butylphenol, 2,6-di-tert-butyl-p-ethylphenol, pentanols include 2,4-di-tert-amylphenol, others include o-ethoxyphenol, o-ethoxybenzene Methyl ether, p-ethyl guaiacol, 2,6-diisopropylanisole). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With molybdenum(VI) oxide; In ethanol; at 280℃; for 4h;Inert atmosphere;Catalytic behavior; | General procedure: 2.0 g of guaiac acid (purchased in Tianjin Guangfu Technology Co., Ltd.), 0.5 g of MOS catalyst and 100 ml of ethanol were placed in a 300 ml reaction vessel, and the air in the reaction vessel was replaced with nitrogen. The temperature was raised to 280 C, and the reaction was stirred for 4 h. After the reaction was completed, the mixture was filtered under suction and rotary evaporated. The liquid product was subjected to qualitative analysis on a gas chromatography-mass spectrometer (GC6890-MS5973, Agilent), and the internal standard was added. Quantitative analysis by gas chromatography. The chromatogram was performed on an HP-5ms, 30m X 0.25mm X 0.25mum capillary column. The conversion of the raw guaiacol is calculated by (initial guaiacol moles - residual guaiacol moles) / (initial guaiacol moles) X100%, and the selectivity of the product hydrocarbyl phenol is (hydrocarbyl phenol) The number of moles / (molar guaiacol moles) X 100 % was calculated. Among the guaiacol conversion products, ethyl phenols include o-ethyl phenol, 2,5-diethyl phenol, 3,5-diethyl phenol, and propyl phenols include 2,6-diisopropyl phenol. , 2,4-diisopropylphenol, 2,4,6-triisopropylphenol, butyl phenols including 2,5-di-sec-butylphenol, 2,6-di-tert-butylphenol, 2, 4-di-tert-butylphenol, 2,6-di-tert-butyl-p-ethylphenol, pentanols include 2,4-di-tert-amylphenol, others include o-ethoxyphenol, o-ethoxybenzene Methyl ether, p-ethyl guaiacol, 2,6-diisopropylanisole). |