129188-99-4

Basic information

• Product Name: 1,1-BIS(4-HYDROXYPHENYL)-3,3,5-TRIMETHYLCYCLOHEXANE
• Synonyms: 1,1-BIS(4-HYDROXYPHENYL)-3,3,5-TRIMETHYLCYCLOHEXANE;1,1-BIS(4-HYDROXYPHENYL)PROPANEBIS(2-HYDROXYPROPYL)ETHER;4,4'-(3,3,5-Trimethyl-1,1-cyclohexanediyl)bisphenol;4,4'-(3,3,5-Trimethylcyclohexane-1,1-diyl)bisphenol;4,4'-(3,3,5-Trimethylcyclohexylidene)bisphenol;4,4'-(3,3,5-Trimethylcyclohexylidene)diphenol;3,3,5-TriMethyl-1,1-bis(4-hydroxyphenyl)cyclohexane;Bis(4-hydroxyphenyl)-3,3,5-triMethylcyclohexane
• CAS NO: 129188-99-4
• Molecular Formula: C₂₁H₂₆O₂
• Molecular Weight: 310.43
• EINECS: 603-320-4
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 129188-99-4.mol

Chemical Properties

• Boiling Point: 450.8°C at 760 mmHg
• Flash Point: 202.8°C
• Appearance: /
• Density: 1.075g/cm³
• Vapor Pressure: 9.59E-09mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 9.91±0.30(Predicted)
• BRN: 9785841
• CAS DataBase Reference: 1,1-BIS(4-HYDROXYPHENYL)-3,3,5-TRIMETHYLCYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-BIS(4-HYDROXYPHENYL)-3,3,5-TRIMETHYLCYCLOHEXANE(129188-99-4)
• EPA Substance Registry System: 1,1-BIS(4-HYDROXYPHENYL)-3,3,5-TRIMETHYLCYCLOHEXANE(129188-99-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 129188-99-4(Hazardous Substances Data)

Usage

Uses

Bisphenol TMC(1,1-Bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane) is a bisphenol derivative used in the preparation of polycarbonate, polyester and epoxy resins.

Synthesis

The synthesis of?1,1-BIS(4-HYDROXYPHENYL)-3,3,5-TRIMETHYLCYCLOHEXANE is as follows:112.8 g (1.2 mol) of phenol, 16.9 g of water, 0.5 g of 75% aqueous solution of phosphoric acid and 7.2 g of BPTMCP crystals were placed in a one liter capacity four-necked flask provided with a thermometer, a dropping funnel, a reflux condenser and a stirrer to prepare a slurry. The slurry was adjusted at a temperature of 20° C. After the inside the flask was replaced by nitrogen gas, hydrogen chloride gas was introduced into the flask under stirring. The gas composition in the reaction vessel was analyzed and the volume concentration of hydrogen chloride gas was adjusted at 80%. 4.2 g of 15% aqueous solution of sodium methyl mercaptide was added dropwise to the slurry while the slurry was maintained at a temperature of 20° C., and then a mixture of 112.8 g (1.2 mol) of phenol and 42.0 g (0.3 mol) of TMC was added dropwise to the slurry over a period of six hours. The reaction mixture was found to increase in temperature during the addition, and when the addition was completed, the temperature was found to be 40° C. Then, the reaction was further continued at a temperature of 40° C. for anther three hours under stirring until completion. The reaction mixture was found to be slurry throughout the reaction from the start of the reaction when the mixture of phenol and TMC was added dropwise to the slurry to the completion of the reaction. The resulting reaction mixture was analyzed by liquid chromatography. The production yield (mol of BPTMC produced/mol of starting TMC used) was found 92.9%.

InChI:InChI=1/C21H26O2/c1-15-12-20(2,3)14-21(13-15,16-4-8-18(22)9-5-16)17-6-10-19(23)11-7-17/h4-11,15,22-23H,12-14H2,1-3H3

Upstream product

• 111-88-6 Octanethiol 
• 873-94-9 dihydroisophorone 
• 108-95-2 phenol 
• 112-55-0 1-dodecylthiol 
• 102-09-0 bis(phenyl) carbonate 

Downstream Products

• 1632142-45-0 1,1-bis(3-nitro-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane 

Relevant articles and documents

BISPHENOL COMPOSITION CONTAINING AROMATIC ALCOHOL SULFONATE AND METHOD FOR PRODUCING SAME, POLYCARBONATE RESIN AND METHOD FOR PRODUCING SAME, AND BISPHENOL PRODUCTION METHOD

A bisphenol composition including a specific amount of aromatic alcohol sulfonate, and a simple method of producing it are provided. Also provided is a method of producing a polycarbonate resin in which, by using the bisphenol composition including a specific amount of aromatic alcohol sulfonate, melt polymerization reaction can be efficiently allowed to proceed to produce a polycarbonate resin having an excellent color tone. A bisphenol composition including an aromatic alcohol sulfonate at not less than 0.1 ppb by mass with respect to a bisphenol. A method of producing a bisphenol composition, including reacting a ketone or an aldehyde with an aromatic alcohol in the presence of sulfuric acid to produce a bisphenol composition. A method of producing a polycarbonate resin, including producing a polycarbonate resin using the bisphenol composition. A polycarbonate resin including a specific amount of aromatic alcohol sulfonate.

1, 1-bis (4-hydroxyphenyl)-3, 3, 5-trimethylcyclohexane manufacturing method

PROBLEM TO BE SOLVED: To provide a method capable of industrially stably producing 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane with high selectivity in high yield.SOLUTION: In the method for producing 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane by reacting phenol with 3,3,5-trimethylcyclohexanone in the presence of an acid catalyst, phenol and 3,3,5-trimethylcyclohaxane are started to react in the presence of an acid catalyst in the slurry constituted of a phenol adduct crystal of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane and water-containing phenol; and the reaction is continuously carried out in the slurry.

Method of producing pure 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane

A method of producing 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane comprising: crystallizing a phenol adduct of 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane from a solution comprising 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane and phenol; washing the phenol adduct with a washing solution comprising phenol and water; decomposing by heating the washed phenol adduct in an aqueous solvent to remove phenol from the phenol adduct, thereby obtaining pure 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane.

Process for production of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane

A process for production of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane which comprises reacting phenol with 3,3,5-trimethylcyclohexanone in the presence of an acid catalyst wherein the reaction of phenol with 3,3,5-trimethylcyclohexanone is started in a slurry comprising phenol adduct crystals of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane and hydrated phenol in the presence of an acid catalyst, and then the reaction is continued in the slurry.

Method for producing 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane

The invention provides a process for production of high purity 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (BPTMC) which comprises: (a) a reaction step wherein phenol is reacted with 3,3,5-trimethylcyclohexanone (TMC) in a slurry containing phenol adduct crystals of BPTMC in the presence of an acid catalyst; (b) a neutralization step wherein after the reaction, the resulting reaction mixture in the form of slurry is neutralized with an alkali while heating to convert the slurry to a solution; (c) a primary crystallization and filtration step wherein the resulting solution is cooled and the resulting phenol adduct crystals of BPTMC are collected by filtration; (d) a secondary crystallization and filtration step wherein the adduct crystals obtained in the primary crystallization and filtration step are heated in a crystallization solvent to dissolve the crystals therein to prepare a solution and then the solution is cooled to crystallize BPTMC out of the solution, followed by collecting the crystals of BPTMC by filtration; (e) a filtrate recycling step wherein at least a part of the secondary crystallization filtrate obtained in the secondary crystallization and filtration step is returned to the reaction step. The process provides uncolored high purity BPTMC in high selectivity and in high yield in an industrially stable manner which is substantially free from residual phenol and trace impurities such as sodium, chlorine and sulfur and hence which is suitable for use as raw materials for the production of resins for optical use.

Process for producing 3, 3, 5-trimethylcyclohexylidenebisphenol

A process for producing a 3,3,5-trimethylcyclohexylidenebisphenol, comprising pre-reacting a phenol (A), i.e., phenol whose 2- and 6-positions may be monosubstituted or disubstituted with an alkyl group having 1 to 4 carbon atoms, with 3,3,5-trimethylcyclohexanone (B) at a molar ratio ((A)/(B)) of 3 to 7 in the presence of an acid catalyst until 3,3,5-trimethylcyclohexanone (B) exhibits a degree of conversion of at least 90 mol %; adding the phenol (A) and/or an aromatic hydrocarbon (C) to the thus obtained reaction mixture; and post-reacting the resultant mixture. This process enables not only suppressing a rise of the viscosity of the reaction mixture but also obtaining the desired product at high yield. Therefore, this process is applicable to not only the productivity enhancement in batch processing but also a continuous reaction processing which has been regarded as being difficult.