Tokuyama Corporation

Daikin Industries, Ltd.

Masao Yamaguchi

Hiromasa Yamamoto

Yoshihiro Hirota

Hideki Kikuchi

Shozo Kato

Toshio Kitajima

Fumihiko Yamaguchi

Takashi Kobayakawa

Noriyuki Fukada

Kenji Tanaka

Seiji Nagata

Hirofumi Shiigi

Norihiro Tanaka

Tadashi Kobutani

Masahiko Ishizaki, Deceased

Makiko Furuki

Hidenobu Itahana

Atsushi Kadokura

Eiji Ohshima

Takashi Matsumura

Hirohumi Shiigi

The present invention discloses a method for producing a fluorine-containing alkyl (meth)acrylate represented by the following general formula (2):Rf&#x2014;(CH)-[-A-(CH)&#x2014;]&#x2014;OCOCR&#x2550;CH&#x2003;&#x2003;(2)(wherein R is a hydrogen atom or a methyl group), characterized by reacting

Method for producing fluorine-containing alkyl (meth)acrylate

According to the present invention there is provided a process for producing an acid anhydride by reacting a carboxylic acid, preferably a carboxylic acid having a polymerizable group, with a sulfonyl halide compound in the presence of a tertiary amine or in the presence of a tertiary amine and an inorganic base, wherein the tertiary amine or the tertiary amine and the inorganic base are used in an amount of 0.9 to 1.2 equivalents relative to the acid generated from the sulfonyl halide compound.

Process for production of acid anhydride

A spirofluorenol such as 3',9&#x2032;-dimethoxy-5&#x2032;-hydroxyspiro[(1H-cyclopent[d,e,f]phenanthrene)-1,7&#x2032;-benzo[c]fluorene] is produced by protecting a hydroxyl group bonded to a particular fluorenone compound such as 3,9-dimethoxy-5-hydroxybenzo[c]fluorene-7-one with 'a substituted silyl group in which the sum of carbon atoms of substituents bonded to a silicon atom is 5 to 12', such as a t-butyldimethylsilyl group, then, reacting the fluorenone compound with a particular organometal compound such as 1-lithiophenanthrene so as to be transformed into a spiro form and, then, removing the protection therefrom. This method makes it possible to efficiently produce the spirofluorenol which is useful as a starting material for producing photochromic compounds.

Process for preparation of spirofluorenols

A magnesium halide salt of a 2-alkyl-2-adamantanol is reacted with a carboxylic acid halide such as acrylic chloride or the like in the presence of a tertiary amine to produce a 2-alkyl-2-adamantyl ester (the first invention). A 2-alkyl-2-adamantanol is reacted with a carboxylic acid such as acrylic acid or the like in the presence of an acid catalyst such as concentrated sulfuric acid or the like and a drying agent composed of an acidic or neutral inorganic compound (e.g. magnesium sulfate) which is a solid at ordinary temperature in a dried state or of a water-absorbing high-molecular compound, to produce a 2-alkyl-2-admantyl ester (the second invention). The above ester is important as a raw material for a resist for semiconductor production.

Processes for preparation of 2-alkyl-2-adamantyl esters

There is provided a method for obtaining a high-purity alkyladamantyl ester from an alkyladamantyl ester composition containing a large quantity of alkyladamantyl halide obtained by, for example, alkylating raw material 2-adamantanone obtained through oxidation of adamantane by use of an organic metal reagent and then causing an acid halide to react with the resulting product, efficiently by a simple process. To an alkyladamantyl ester composition containing an alkyladamantyl halide such as 2-chloro-2-methyladamantane in an amount of larger than 0.5 parts by weight based on 100 parts by weight of alkyladamantyl ester such as 2-methyl-2-adamantyl methacrylate, a mixed solution of, for example, methanol and a sodium hydroxide aqueous solution is added. By bringing the alkali compound into contact with the alkyladamantyl halide in a homogeneous system so as to convert the halide into a compound which produces no acid when heated, the amount of the alkyladamantyl halide in the composition is reduced to 0.5 parts by weight or less based on 100 parts by weight of the alkyladamantyl ester, after which distillation is carried out.

Process for preparing alkyladamantyl esters and compositions

This invention discloses a process for preparing a dihalogenated adamantane by reacting an adamantane optionally substituted with alkyl at 1-position with a halosulfonic acid, comprising the first stage of monohalogenation conducted at &#x2212;5 to 15&#xb0; C. and then the second stage of dihalogenation conducted at 17 to 35&#xb0; C., preferably in the absence of an organic solvent.

Process for preparing dihalogenated adamantanes

The present invention discloses an adamantyl ester monomer composition characterized by containing at least an adamantyl ester monomer having at least one polymerizable unsaturated bond in the molecule, and a compound represented by the following general formula (1):(in the formula, Ris an alkyl group of 1 to 5 carbon atoms, Ris an alkyl group of 1 to 5 carbon atoms, Ris a hydrogen atom or an alkyl group of 1 to 5 carbon atoms, and Ris a hydrogen atom or a methyl group). The composition has high storage stability and, by subjecting it to distillation, an adamantyl ester monomer of high purity can be obtained easily.

Adamantyl ester monomer composition

There is provided a method for obtaining a target organic compound such as an alkyladamantyl ester efficiently by purifying a crude organic compound which contains, as impurities, sublimable materials which start to sublime at temperatures lower than a boiling point of the target organic compound by use of such a simple method as distillation during its production process, without being adversely affected by adherence of the sublimable materials. The distillation is carried out in the presence of a compound having a boiling point which is lower than a boiling point of the target organic compound, e.g., a carbonyl-group-containing compound. For example, 2-methyl-2-adamantyl methacrylate (boiling point: 92&#xb0; C./0.3 mmHg) containing sublimable impurities such as adamantane (sublimation starting temperature: room temperature or lower) is distilled in the presence of 1,3-dimethyl-2-imidazolidinone (boiling point: 225&#xb0; C.).

Production method of high purity organic compound

A high-purity alicyclic ketone which is a raw material for an alkyl-substituted alicyclic ester such as an alkyl adamantyl ester compound which is useful as a resist raw material can be obtained by a simple operation such as extraction without a special purification step such as distillation or recrystallization. In this process, when an alicyclic hydrocarbon is oxidized with concentrated sulfuric acid or fuming sulfuric acid, the reaction solution after oxidation is poured into water and a solid is extracted with an organic solvent, the concentration of sulfuric acid in the water layer at the time of extraction is adjusted to 60 to 90 wt % to carry out extraction so as to obtain an alicyclic ketone.

Process for the preparation of alicyclic ketones and an alkyl-substituted alicyclic esters

This invention discloses a process for preparing an 2-alkyl-2-adamantyl ester comprising the steps of combining a solution or suspension of 2-adamantanone and an alkyl halide with lithium metal for reacting them to generate an lithium 2-alkyl-2-adamantyl alcoholate, and then reacting the lithium 2-alkyl-2-adamantyl alcoholate with an acid halide.

Process for producing 2-alkyl-2-adamantyl ester

Process of the preparation of high-purity alkyladamantyl esters

Ketonitrile derivatives and antibacterial agent and drugs containing the

A cyanoketone derivatives of the following formula (1) ##STR1## which are characterized by excellent herbicidal activity and effectiveness against a variety of broad leafed weeds, including barnyard grass, green foxtail, velvet leaf, livid amaranth and hairy beggar ticks.

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Yamaguchi, Japan

Masao Yamaguchi