Provided is a process for the preparation of certain 1,4-bicyclo[2.2.2]octane derivatives. The new synthetic procedure involves treating 1,4-dimethylene cyclohexane with an oxidizing agent in the presence of a transition metal catalyst to afford an oxo-substituted bicyclo[2.2.2]octane species. This intermediate structure can then be further derivatized. The processes of this disclosure thus affords a novel and simplified means for the commercial production of a wide variety of bicyclo[2.2.2]octane derivatives.

Provided is a process for the preparation of certain 1,4-bicyclo[2.2.2]octane derivatives. The new synthetic procedure involves treating 1,4-dimethylene cyclohexane with an oxidizing agent in the presence of a transition metal catalyst to afford an oxo-substituted bicyclo[2.2.2]octane species. This intermediate structure can then be further derivatized. The processes of this disclosure thus affords a novel and simplified means for the commercial production of a wide variety of bicyclo[2.2.2]octane derivatives.

A fixed-bed multi-tubular reactor for producing an alkenyl acetate by a gas phase catalytic oxidation reaction of a lower olefin, acetic acid and oxygen including a plurality of reaction tubes, a thermometer protection tube inserted into at least one of the plurality of reaction tubes, a thermometer inserted into the thermometer protection tube, and a shield disposed above the reaction tube into which the thermometer protection tube is inserted and attached to the thermometer protection tube, wherein an effective projection region of the shield entirely covers the inlet opening of the reaction tube into which the thermometer protection tube is inserted.

A fixed-bed multi-tubular reactor for producing an alkenyl acetate by a gas phase catalytic oxidation reaction of a lower olefin, acetic acid and oxygen including a plurality of reaction tubes, a thermometer protection tube inserted into at least one of the plurality of reaction tubes, a thermometer inserted into the thermometer protection tube, and a shield disposed above the reaction tube into which the thermometer protection tube is inserted and attached to the thermometer protection tube, wherein an effective projection region of the shield entirely covers the inlet opening of the reaction tube into which the thermometer protection tube is inserted.

A fixed-bed multi-tubular reactor for producing an alkenyl acetate by a gas phase catalytic oxidation reaction of a lower olefin, acetic acid and oxygen including a plurality of reaction tubes, a thermometer protection tube inserted into at least one of the plurality of reaction tubes, a thermometer inserted into the thermometer protection tube, and a shield disposed above the reaction tube into which the thermometer protection tube is inserted and attached to the thermometer protection tube, wherein an effective projection region of the shield entirely covers the inlet opening of the reaction tube into which the thermometer protection tube is inserted.

A fixed-bed multi-tubular reactor for producing an alkenyl acetate by a gas phase catalytic oxidation reaction of a lower olefin, acetic acid and oxygen including a plurality of reaction tubes, a thermometer protection tube inserted into at least one of the plurality of reaction tubes, a thermometer inserted into the thermometer protection tube, and a shield disposed above the reaction tube into which the thermometer protection tube is inserted and attached to the thermometer protection tube, wherein an effective projection region of the shield entirely covers the inlet opening of the reaction tube into which the thermometer protection tube is inserted.

A fixed-bed multi-tubular reactor for producing an alkenyl acetate by a gas phase catalytic oxidation reaction of a lower olefin, acetic acid and oxygen including a plurality of reaction tubes, a thermometer protection tube inserted into at least one of the plurality of reaction tubes, a thermometer inserted into the thermometer protection tube, and a shield disposed above the reaction tube into which the thermometer protection tube is inserted and attached to the thermometer protection tube, wherein an effective projection region of the shield entirely covers the inlet opening of the reaction tube into which the thermometer protection tube is inserted.

A method for producing a 1-acyloxy-2-methyl-2-propene represented by the following general formula (II), including reacting a carboxylic acid represented by the following general formula (I), isobutylene, and oxygen, in the presence of a catalyst, in a liquid phase, with an amount of the isobutylene used of more than 1 mol and 50 mol or less per 1 mol of the carboxylic acid. ##STR00001##

A method for producing a 1-acyloxy-2-methyl-2-propene represented by the following general formula (II), including reacting a carboxylic acid represented by the following general formula (I), isobutylene, and oxygen, in the presence of a catalyst, in a liquid phase, with an amount of the isobutylene used of more than 1 mol and 50 mol or less per 1 mol of the carboxylic acid. ##STR00001##

A method for producing a 1-acyloxy-2-methyl-2-propene represented by the following general formula (II), including reacting a carboxylic acid represented by the following general formula (I), isobutylene, and oxygen, in the presence of a catalyst, in a liquid phase, with an amount of the isobutylene used of more than 1 mol and 50 mol or less per 1 mol of the carboxylic acid. ##STR00001##