An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.

Provided is a method for producing an organic compound, the method making it possible to ensure an adequate reaction time and obtain a targeted substance at a high yield even in an organic reaction that requires a relatively long time to complete the reaction. A method for producing an organic compound, wherein the method is characterized in that: a fluid processing apparatus F used in the production method is equipped with an upstream processing unit that processes a fluid to be processed between at least two processing surfaces 1 and 2 that relatively rotate, and a downstream processing unit disposed downstream of the upstream processing unit, the downstream processing unit being provided with a plurality of labyrinth seals that function to retain and stir the fluid to be processed that has been processed by the upstream processing unit; due to the fluid to be processed, which contains at least one type of organic compound, being passed through the upstream processing unit, the fluid to be processed is subjected to upstream processing; due to the fluid to be processed that has been subjected to upstream processing being passed through the downstream processing unit, the fluid to be processed that has been subjected to upstream processing is subjected to downstream processing; and the upstream processing and the downstream processing are performed continuously.

Provided is a method for producing an organic compound, the method making it possible to ensure an adequate reaction time and obtain a targeted substance at a high yield even in an organic reaction that requires a relatively long time to complete the reaction. A method for producing an organic compound, wherein the method is characterized in that: a fluid processing apparatus F used in the production method is equipped with an upstream processing unit that processes a fluid to be processed between at least two processing surfaces 1 and 2 that relatively rotate, and a downstream processing unit disposed downstream of the upstream processing unit, the downstream processing unit being provided with a plurality of labyrinth seals that function to retain and stir the fluid to be processed that has been processed by the upstream processing unit; due to the fluid to be processed, which contains at least one type of organic compound, being passed through the upstream processing unit, the fluid to be processed is subjected to upstream processing; due to the fluid to be processed that has been subjected to upstream processing being passed through the downstream processing unit, the fluid to be processed that has been subjected to upstream processing is subjected to downstream processing; and the upstream processing and the downstream processing are performed continuously.

Provided is a method for producing an organic compound, the method making it possible to ensure an adequate reaction time and obtain a targeted substance at a high yield even in an organic reaction that requires a relatively long time to complete the reaction. A method for producing an organic compound, wherein the method is characterized in that: a fluid processing apparatus F used in the production method is equipped with an upstream processing unit that processes a fluid to be processed between at least two processing surfaces 1 and 2 that relatively rotate, and a downstream processing unit disposed downstream of the upstream processing unit, the downstream processing unit being provided with a plurality of labyrinth seals that function to retain and stir the fluid to be processed that has been processed by the upstream processing unit; due to the fluid to be processed, which contains at least one type of organic compound, being passed through the upstream processing unit, the fluid to be processed is subjected to upstream processing; due to the fluid to be processed that has been subjected to upstream processing being passed through the downstream processing unit, the fluid to be processed that has been subjected to upstream processing is subjected to downstream processing; and the upstream processing and the downstream processing are performed continuously.

A process for the reactivation of an acidic ion exchange resin is described. The invention relates to the treatment of an at least partially deactivated resin which has been deactivated by contact with an impure ethylenically unsaturated acid or ester containing target impurities. The reactivation includes the step of contacting the at least partially deactivated resin with an alcohol to thereby increase the activity thereof. The invention extends to reactivating a resin deactivated by contact with an impure ethylenically unsaturated acid, ester or nitrile containing target impurities by contacting the at least partially deactivated resin with an alcohol and a carboxylic acid to thereby increase the activity thereof. A reactivated resin and a process for preparing and purifying an ethylenically unsaturated acid or ester of the following formula:
R.sup.1—C(═(CH.sub.2).sub.m)—COOR.sup.2
are also described.

A process for the reactivation of an acidic ion exchange resin is described. The invention relates to the treatment of an at least partially deactivated resin which has been deactivated by contact with an impure ethylenically unsaturated acid or ester containing target impurities. The reactivation includes the step of contacting the at least partially deactivated resin with an alcohol to thereby increase the activity thereof. The invention extends to reactivating a resin deactivated by contact with an impure ethylenically unsaturated acid, ester or nitrile containing target impurities by contacting the at least partially deactivated resin with an alcohol and a carboxylic acid to thereby increase the activity thereof. A reactivated resin and a process for preparing and purifying an ethylenically unsaturated acid or ester of the following formula:
R.sup.1—C(═(CH.sub.2).sub.m)—COOR.sup.2
are also described.

A process for the reactivation of an acidic ion exchange resin is described. The invention relates to the treatment of an at least partially deactivated resin which has been deactivated by contact with an impure ethylenically unsaturated acid or ester containing target impurities. The reactivation includes the step of contacting the at least partially deactivated resin with an alcohol to thereby increase the activity thereof. The invention extends to reactivating a resin deactivated by contact with an impure ethylenically unsaturated acid, ester or nitrile containing target impurities by contacting the at least partially deactivated resin with an alcohol and a carboxylic acid to thereby increase the activity thereof. A reactivated resin and a process for preparing and purifying an ethylenically unsaturated acid or ester of the following formula:
R.sup.1—C(═(CH.sub.2).sub.m)—COOR.sup.2
are also described.

A method of producing an ethylenically unsaturated carboxylic acid or ester such as (meth) acrylic acid or alkyl esters thereof, for example, methyl methacrylate is described. The process comprises the steps of contacting formaldehyde or a suitable source thereof with a carboxylic acid or ester, for example, propionic acid or alkyl esters thereof in the presence of a catalyst and optionally an alcohol. The catalyst comprises group II metal phosphate crystals having rod or needle like morphology or a suitable source thereof. The phosphate may be a hydroxyapatite, pyrophosphate, hydroxyphosphate, PO.sub.4.sup.2− phosphate or mixtures thereof. The group II metal may be selected from Ca, Sr, Ba or mixtures thereof, for example, strontium hydroxyapatite and calcium hydroxyapatite. A catalyst system comprising a crystalline metal phosphate catalyst and a catalyst support is also described. The metal phosphate has rod/needle like morphology.

A method of producing an ethylenically unsaturated carboxylic acid or ester such as (meth) acrylic acid or alkyl esters thereof, for example, methyl methacrylate is described. The process comprises the steps of contacting formaldehyde or a suitable source thereof with a carboxylic acid or ester, for example, propionic acid or alkyl esters thereof in the presence of a catalyst and optionally an alcohol. The catalyst comprises group II metal phosphate crystals having rod or needle like morphology or a suitable source thereof. The phosphate may be a hydroxyapatite, pyrophosphate, hydroxyphosphate, PO.sub.4.sup.2− phosphate or mixtures thereof. The group II metal may be selected from Ca, Sr, Ba or mixtures thereof, for example, strontium hydroxyapatite and calcium hydroxyapatite. A catalyst system comprising a crystalline metal phosphate catalyst and a catalyst support is also described. The metal phosphate has rod/needle like morphology.

A method of producing an ethylenically unsaturated carboxylic acid or ester such as (meth) acrylic acid or alkyl esters thereof, for example, methyl methacrylate is described. The process comprises the steps of contacting formaldehyde or a suitable source thereof with a carboxylic acid or ester, for example, propionic acid or alkyl esters thereof in the presence of a catalyst and optionally an alcohol. The catalyst comprises group II metal phosphate crystals having rod or needle like morphology or a suitable source thereof. The phosphate may be a hydroxyapatite, pyrophosphate, hydroxyphosphate, PO.sub.4.sup.2− phosphate or mixtures thereof. The group II metal may be selected from Ca, Sr, Ba or mixtures thereof, for example, strontium hydroxyapatite and calcium hydroxyapatite. A catalyst system comprising a crystalline metal phosphate catalyst and a catalyst support is also described. The metal phosphate has rod/needle like morphology.