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Phenol / BF3 / HgO, CH-=CH; |
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Specific examples of bisphenols described by the above formulainclude bis(hydroxyaryl)alkanes such as 1,1-bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, 1,1-bis(4-hydroxyphenyl)propane 1,1-bis(4-hydroxyphenyl)-n-butane, bis(4-hydroxyphenyl)phenylmethane 2,2-bis(4-hydroxy-1-methylphenyl)propane, ... |
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Exemplary suitable aromatic dihydroxy compounds include: bis(hydroxyaryl) alkanes such as bis(4-hydroxyphenyl) methane, 1,1-bis(4'-hydroxyphenyl) ethane, 1,2-bis(4'-hydroxyphenyl) ethane, bis(4-hydroxyphenyl) phenylmethane, bis(4-hydroxyphenyl) diphenylmethane, bis(4-hydroxyphenyl)-1-naphthylmethane, 1,1-bis(4'-hydroxyphenyl)-1-phenylethane, 2,2-bis(4'-hydroxyphenyl) propane ["bisphenol A"], 2-(4'-hydroxyphenyl)-2-(3'-hydroxyphenyl) propane, ... |
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2 Production of Clathrate Compound of Cl-MIT and 4,4'-Ethylidene-Bisphenol (By Methanol Solvent Method)
EXAMPLE 2 Production of Clathrate Compound of Cl-MIT and 4,4'-Ethylidene-Bisphenol (By Methanol Solvent Method) The same process as in Example 1 was repeated, except that 0.5 g (3.34 mmol) of Cl-MIT and the same molar amount of 4,4'-ethylidene-bisphenol were used, and the product was analyzed in the same manner as in Example 1. The product was identified to be a clathrate compound of 4,4'-ethylidene-bisphenol/Cl-MIT of nearly 1/1 (by mol), having a Cl-MIT content of 37.84% by weight. |
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The following dihydroxyaromatic compounds are illustrative: ... 2,6-Dihydroxynaphthalene Bis(4-hydroxyphenyl)methane Bis(4-hydroxyphenyl)diphenylmethane Bis(4-hydroxyphenyl)-1-naphthylmethane 1,1-Bis(4-hydroxyphenyl)ethane 1,2-Bis(4-hydroxyphenyl)ethane 1,1-Bis(4-hydroxyphenyl)-1-phenylethane 2,2-Bis(4-hydroxyphenyl)propane ("bisphenol A") ... |
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The A1 values may be considered as being derived from dihydroxyaromatic compounds of the formula HO--A1 --OH, preferably bisphenols of the formula HO--A2 --Y--A3 --OH. The following dihydroxy compounds are illustrative: ... 2,6-Dihydroxynaphthalene Bis(4-hydroxyphenyl)methane Bis(4-hydroxyphenyl)diphenylmethane Bis(4-hydroxyphenyl)-1-naphthylmethane 1,1-Bis(4-hydroxyphenyl)ethane 1,2-Bis(4-hydroxyphenyl)ethane 1,1-Bis(4-hydroxyphenyl)-1-phenylethane 2,2-Bis(4-hydroxyphenyl)propane ("bisphenol A") ... |
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...ay be considered as being derived from dihydroxy compounds of the formula HO--R4 --OH, especially dihydroxyaromatic compounds and preferably bisphenols of the formula HO--A2 --Y3 --A3 --OH. The following dihydroxy compounds are illustrative: Ethylene glycol ... 2,6-Dihydroxynaphthalene Bis(4-hydroxyphenyl)methane Bis(4-hydroxyphenyl)diphenylmethane Bis(4-hydroxyphenyl)-1-naphthylmethane 1,1-Bis(4-hydroxyphenyl)ethane 1,2-Bis(4-hydroxyphenyl)ethane 1,1-Bis(4-hydroxyphenyl)-1-phenylethane 2,2-Bis(4-hydroxyphenyl)propane ("bisphenol A") ... |
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The following may be mentioned for example: 4,4'-methylene-bis(phenol), 4,4'-ethylidene-bis(phenol), 4,4'-thio-bis(phenol), 4,4'-thionyl-bis(phenol), 4,4'-dithio-bis(phenol), 4,4'-dihydroxystilbene, |
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3 EXAMPLE 3
EXAMPLE 3 Into a solution of 697 g of diethyl acetal (5.9 moles) and 3764 g (40 moles) of phenol was introduced at 40° C. with stirring a slow stream of anhydrous hydrogen chloride gas. External cooling was applied to maintain the reaction temperature between 36° and 48° C. After 2.5 hours solids began to separate out from the solution, at which point the introduction of HCl was stopped and the reaction mixture allowed to crystallize at ambient temperature during a 12 hour period. The solids, which were filtered, washed with cyclohexane and air-dried, weighed 890 g and consisted of the 1:1 adduct of 4,4'-ethylidenediphenol and phenol. Separation of the phenol by vacuum distillation at 14 mm pressure left behind the diphenol, that was 98.3% pure by gas chromatographic analysis. One recrystallization from benzene yielded 4,4'-ethylidenediphenol, 99.8% pure by gas chromatography, melting point 123°-125° C. |
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Specific examples of the bisphenol of the formula above include bis(hydroxyaryl)alkanes such as 1,1-bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane (referred to in the following as bisphenol A), 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, 1,1-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)n-butane, bis(4-hydroxyphenyl)phenylmethane, 2,2-bis(4-hydroxy-1-methylphenyl)propane, ... |
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Typical examples of the aromatic diol represented by formula (4) include hydroquinone, resorcinol, catechol, ... 2,4'-dihydroxybiphenyl, 2,2'-dihydroxybiphenyl, 4,4'-dihydroxydiphenylmethane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane, ... |
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Specific examples of the bisphenol of formula above include bis(hydroxyaryl)alkanes such as: 1,1-bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane (referred to in the following as bisphenol A), 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, 1,1-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)n-butane, bis(4-hydroxyphenyl)phenylmethane, 2,2-bis(4-hydroxy-1-methylphenyl)propane, ... |
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Specific examples of bisphenols include: bis(4-hydroxylphenyl)methane; bis(4-hydroxy-2-methylphenyl)methane; 1,1-bis(4-hydroxyphenyl)ethane; 1,1-bis(4-hydroxy-3-methyl-5-t-butylphenyl)butane; bis(4-hydroxy-2-chlorophenyl)methane; ... |
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1 EXAMPLE 1
One recrystallization from benzene yielded 4,4'-ethylidenediphenol, melting point 123° to 125° C., that was 99.8% pure by gas chromatography. |
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Diacetoxyethan, Phenol; |
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Phenol, Diacetoxyethan; |
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With dodecatungstosilic acid; 1-dodecylthiol at 40 - 50℃; for 6h; |
3 Synthesis of 1,1-bis(3-methyl-4-hydroxyphenyl)ethane (p-120)
General procedure: Aftero-cresol (10.8 g, 100 mmol) was heated to 40 ° C. and melted. Silicotungstic acid (33.1 mg, 0.0100 mmol) and n-dodecyl mercaptan (0.202 g, 1.00 mmol) were added.Then, paraldehyde (0.880 g, 6.67 mmol) was added dropwise over 4 hours while maintaining the internal temperature at 50 ° C.After the dropping, the mixture was heated and stirred for 2 hours for aging.A part of the obtained reaction solution was taken and subjected to LC and GC analysis.The paraldehyde conversion was 100% and the 4,4'-substituent selectivity was 92%. |
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