The Dow Chemical Company

Dow Global Technolgoies LLC

Marlin E Walters

Emmett L Tasset

W Frank Richey

Richard Michael Wehmeyer

Clark H Cummins

Malcolm F Finlayson

Marius W Sorenson

Robin J Lee

George M St George

Katherine S Clement

Steven L Brewster

Paul M Puckett

V Rao Durvasula

Hong A Nguyen

Richard P Kolonko

The present invention includes a molecular melt composition comprising an antioxidant and a coupling agent. The molecular melt is partially amorphous in nature. The invention also includes a method for making the molecular melt composition and a method for using the molecular melt to produce coupled polymers. The invention further includes a method for using an antioxidant to phlagmatize a coupling agent.

Molecular melt and methods for making and using the molecular melt

A catalyst useful for the condensation of an aldehyde or ketone starting material with a phenol is an insoluble mercaptosulfonic acid compound. The heterogeneous catalysts comprise catalytically-active species represented by the formula: ##STR1## L is an optional linking group and--is a bond, which catalytically-active species is attached by the bond--to an insoluble organic or inorganic support;

Supported mercaptosulfonic acid compounds useful as catalysts for

A catalyst useful for the condensation of an aldehyde or ketone starting material with a phenol is an insoluble mercaptosulfonic acid compound. The heterogeneous catalysts comprise catalytically-active species represented by the formula: ##STR1## L is an optional linking group and -- is a bond, which catalytically-active species is attached by the bond -- to an insoluble organic or inorganic support;

Polymeric substrate containing mercapto and sulfonic groups

A process for the oxidation of a fluorene compound to a corresponding fluorenone compound comprises treating the fluorene compound with an oxidizing gas in the presence of a solid alkali metal or alkaline earth metal oxide or hydroxide or a concentrated aqueous solution thereof in a reaction mixture in a non-aqueous heterocylic nitrogenous solvent, wherein the reaction mixture is free of a phase transfer agent, for a time sufficient and at a temperature sufficient to convert the fluorene compound to the fluorenone compound.

Process for making fluorenones

The invention involves aromatic polyhydroxy compounds, including triaromatic bisphenols and tris-[1,1,1-(4-hydroxyphenyl)] toluenes, and a process for the preparation thereof by reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl, excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene, and a large portion of the yield is para isomer. Suitable halo-compounds include aromatic dihalo-compounds having at least one aliphatic substituent having two alpha-halogen atoms and at least one beta halogen atom, halo-styrenes having structures corresponding to such aromatic dihalo-compounds except that an alpha-halogen atom and a beta hydrogen atom are removed and there is a double bond between the alpha and beta carbon atoms, trihalotoluenes, and dihalocyanotoluenes.

Aromatic polyhydroxy compounds and process for the preparation thereof

A process for the condensation of an aldehyde or ketone starting material with a phenol, unsubstituted in the 4-position, comprises reacting the aldehyde or ketone starting material with the phenol in a reaction mixture in the presence of a soluble or insoluble mercaptosulfonic acid compound under conditions sufficient to bring about formation of a geminal bisphenolic moiety at each aldehyde or ketone moiety in the starting material. A miscible mercaptosulfonic acid compound is characterized by the formula

Process for making polyphenols from ketones or aldehydes and phenols

Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.

Chlorination process, alkylation of products of said process and some

The invention involves aromatic polyhydroxy compounds, including triaromatic bisphenols and tris-1,1,1-(4-hydroxyphenyl)] toluenes, and a process for the preparation thereof by reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene, and a large portion of the yield is para isomer. Suitable halo-compounds include aromatic dihalo-compounds having at least one aliphatic substituent having two alpha-halogen atoms and at least one beta halogen atom, halo-styrenes having structures corresponding to such aromatic dihalo-compounds except that an alpha-halogen atom and a beta hydrogen atom are removed and there is a double bond between the alpha and beta carbon atoms, trihalotoluenes, and dihalocyanotoluenes.

Ketones are prepared by admixing at least one gem-dichloro compound with at least one acid such that the ketone wherein the keto-oxygen replaces the gem-dichloro group is formed. The reaction is exemplified by the reaction of 9,9-dichlorofluorene with an acid such that fluorenone is formed. This process has the advantage that no oxidizing agent is used.

Process of making ketones

Active methine compounds are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylonium hydroxide. Chlorinated products, preferably tertiary alkyl chloro compounds, are produced. The tertiary alkyl chloro compounds are useful in elimination reactions, preferably reactions with base, to form unsaturated compounds, particularly compounds having a vinylidene or exomethylene group.

Chlorination and elimination process and some products thereof

The invention is a process for the preparation of triaromatic bisphenols reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl, excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene and a large portion of the yield is para isomer. Suitable halo-compounds include aromatic dihalo-compounds having at least one aliphatic substituent having two alpha-halogen atoms and at least one beta halogen atom, halo-styrenes having structures corresponding to such aromatic dihalo-compounds except that an alpha-halogen atom and a beta hydrogen atom are removed and there is a double bond between the alpha and beta carbon atoms, trihalotoluenes, and dihalocyanotoluenes.

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West Columbia, TX, United States of America

Marlin E Walters