Amoco Corporation

Bp Corporation North America Inc.

Bp Amoco Corporation

John M Weis

Thomas G Smith

Yenamandra Viswanath

Gary P Hagen

Gregory E Schmidt

Edward E Paschke

Juergen K Holzhauer

Bruce I Rosen

Mark W Meszaros

John A Macek

John S Bramlet

Lawrence L Lang

Stefanos L Sakellarides

David J Schneider

Larry D Lillwitz

The synthesis of dimethyl-1,5-naphthalenedicarboxylate and polymers and articles formed therefrom is disclosed, as well as applications for dimethyl-1,5-naphthalenedicarboxylate, its corresponding acid 1,5-NDA, and various synthesis intermediates.

Synthesis and use of dimethyl 1,5-naphthalenedicarboxlyates and intermediates therefrom

A method for recovering crystalline 2,6-dimethylnaphthalene comprising crystallizing in a scraped-wall crystallizer apparatus at crystallization temperature T, a mixture of low melting components, LM, having melting points of 70.degree. F. and below, and high melting components (HM), including 2,6-dimethylnaphthalene, having melting points above 70.degree. F, such that: ##EQU1## where HM is the total weight percent of high melting components, including 2,6-dimethylnaphthalene, in the mixture, and LM is the total weight percent of low melting components in the mixture, and where T is the temperature of the crystallization in degrees Fahrenheit, and where A is at least 1.0.

Crystallization of 2,6-dimethylnaphthalene

A method for recovering crystalline 2,6-dimethylnaphthalene comprising crystallizing in a scraped-wall crystallizer apparatus at crystallization temperature T, a mixture of low melting components, LM, having melting points of 70.degree. F. and below, and high melting components (HM), including 2,6-dimethylnaphthalene, having melting points above 70.degree. F., such that: ##EQU1## where HM is the total weight percent of high melting components, including 2,6-dimethylnaphthalene, in the mixture, and LM is the total weight percent of low melting components in the mixture, and where T is the temperature of the crystallization in degrees Fahrenheit, and where A is at least 1.0.

Crystallizaiton of 2,6-dimethylnaphthalene

A regioselective acylation process is provided for coverting a 2-methylnaphthalene compound to a 2-acetyl-6-methylnaphthalene compound. The process is conducted under liquid phase conditions in an acylation inert solvent using a complexing agent which is regiospecific for the beta position of naphthalene and which is a thermally stable nitrohydrocarbon compound. Preferred such agents are nitrobenzene, o-nitrotoluene, and mesitylene. Also provided is a novel method for producing a 2-acetyl-6-methylnaphthalene compound of relatively high purity from isomer mixtures by recrystallization from a hydrocarbon solvent, such as n-octane, isooctane, or n-nonane.

2-acyl-6-methylnaphthalene preparation

A regioselective acetylation process is provided for converting a 2-methylnaphthalene compound to a 2-acetyl-6-methylnaphthalene compound. The process is conducted under liquid phase conditions using a new complexing agent which is regiospecific for the beta position of naphthalene and which is an electron-rich, carbon-based compound. A preferred such agent is hexamethylbenzene. Also provided is a novel method for producing a 2-acetyl-6-methylnaphthalene compound of relative high purity from isomer mixtures by recrystallization from a hydrocarbon solvent, such as n-octane, isooctane, or n-nonane.

Preparation of 2-acyl-6-methylnaphthalenes

A method of separating 3,3',4,4'-tetramethyldiphenyl ether from its solid mixture with 2,3,3',4'-tetramethyldiphenyl ether.

Separation of 3,3'4,4'- and 2,3,3',4'-tetramethyldiphenyl ether

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Naperville, IL, United States of America

John M Weis