Process for the manufacture of peroxycarboxylic acids

Claim 2

In a process for the manufacture of a peroxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a carboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said carboxylic acid present in the reaction mixture, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the peroxycarboxylic acid to selectively remove from said aqueous phase the peroxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide.

Claim 3

The process of claim 1 wherein the strong acid is methanesulfonic acid.

Claim 4

The process of claim 1 wherein the inert, water-immiscible solvent is monochlorobenzene.

Claim 5

The process of claim 1 wherein the water-immiscible solvent is ortho-dichlorobenzene.

Claim 6

In a process for the manufacture of a peroxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a long chain carboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said carboxylic acid present in the reaction mixture, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the peroxycarboxylic acid to selectively remove from said aqueous phase the peroxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide; separating by decantation the aqueous phase from the water-immiscible solvent; and crystallizing from said solvent the peroxycarboxylic acid.

Claim 7

In a process for the manufacture of a peroxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a long chain carboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said carboxylic acid present in the reaction mixture, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the peroxycarboxylic acid to selectively remove from said aqueous phase the peroxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide; separating by decantation the aqueous phase from the water-immiscible solvent; and crystallizing from said solvent the peroxycarboxylic acid.

Claim 8

In a process for the manufacture of a diperoxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a long chain dicarboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said carboxylic acid present in the reaction mixture, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the diperoxycarboxylic acid to selectively remove from said aqueous phase the peroxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide; separating by decantation the aqueous phase from the water-immiscible solvent; and crystallizing from said solvent the diperoxycarboxylic acid.

Claim 9

In a process for the manufacture of a diperoxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a long chain dicarboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said carboxylic acid present in the reaction mixture, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the diperoxycarboxylic acid to selectively remove from said aqueous phase the peroxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide; separating by decantation the aqueous phase from the water-immiscible solvent; and crystallizing from said solvent the diperoxycarboxylic acid.

Claim 10

The process of claim 6 wherein the strong acid is 96% sulfuric acid.

Claim 11

The process of claim 6 wherein said diperoxycarboxylic acid is diperoxydodecanedioic acid.

Claim 12

The process of claim 6 wherein said diperoxycarboxylic acid is diperoxyazelaic acid.

Claim 13

The process of claim 6 wherein said diperoxycarboxylic acid is diperoxysebacic acid.

Claim 14

The process of claim 6 wherein said diperoxycarboxylic acid is diperoxytetradecanedioic acid.

Claim 15

The process of claim 6 wherein said reaction is carried out at the refluxing temperature of the inert, water-immiscible solvent.

Claim 16

The process of claim 6 wherein the inert, water-immiscible solvent is chloroform.

Claim 17

The process of claim 6 wherein the inert, water-immiscible solvent is carbon tetrachloride.

Claim 18

The process of claim 6 wherein the inert, water-immiscible solvent is 1,2-dichloroethane.

Claim 19

The process of claim 6 wherein the inert, water-immiscible solvent is 1,1,2,2-tetrachloroethane.

Claim 20

The process of claim 6 wherein the inert, water-immiscible solvent is trichloro-trifluoro ethane.

Claim 21

The process of claim 6 wherein the inert, water-immiscible solvent is methylene chloride.

Claim 22

In a process for the manufacture of a peroxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a carboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said carboxylic acid, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the peroxycarboxylic acid to selectively remove from said aqueous phase the peroxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide; adding water to the reaction mixture at the conclusion of the reaction; distilling off the water-immiscible solvent at a temperature below the decomposition temperature of the peroxycarboxylic acid and separating the peroxycarboxylic acid crystals from the residual aqueous phase.

Claim 23

In a process for the manufacture of a peroxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a carboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said carboxylic acid, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the peroxycarboxylic acid to selectively remove from said aqueous phase the peroxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide; adding water to the reaction mixture at the conclusion of the reaction; distilling off the water-immiscible solvent at a temperature below the decomposition temperature of the peroxycarboxylic acid and separating the peroxycarboxylic acid crystals from the residual aqueous phase.

Claim 24

The process of claim 19 wherein the strong acid is methanesulfonic acid.

Claim 25

The process of claim 19 wherein said immiscible solvent is monochlorobenzene.

Claim 26

The process of claim 19 wherein said immiscible solvent is ortho-dichlorobenzene.

Claim 27

In a process for the manufacture of a peroxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a long chain carboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said carboxylic acid present in the reaction mixture, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the peroxycarboxylic acid to selectively remove from said aqueous phase the peroxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide; adding water to the reaction mixture at the conclusion of the reaction; distilling off the water-immiscible solvent at a temperature below the decomposition temperature of the peroxycarboxylic acid and separating the peroxycarboxylic acid crystals from the residual aqueous phase.

Claim 28

In a process for the manufacture of a peroxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a long chain carboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said carboxylic acid present in the reaction mixture, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the peroxycarboxylic acid to selectively remove from said aqueous phase the peroxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide; adding water to the reaction mixture at the conclusion of the reaction; distilling off the water-immiscible solvent at a temperature below the decomposition temperature of the peroxycarboxylic acid and separating the peroxycarboxylic acid crystals from the residual aqueous phase.

Claim 29

In a process for the manufacture of a diperoxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a long chain dicarboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said dicarboxylic acid present in the reaction mixture, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the diperoxycarboxylic acid to selectively remove from said aqueous phase the diperoxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide; adding water to the reaction mixture at the conclusion of the reaction; distilling off the water-immiscible solvent at a temperature below the decomposition temperature of the diperoxycarboxylic acid and separating the diperoxycarboxylic acid crystals from the residual aqueous phase.

Claim 30

In a process for the manufacture of a diperoxycarboxylic acid in crystalline form by the oxidation in an aqueous phase of a long chain dicarboxylic acid with hydrogen peroxide, the improvement which comprises: conducting the reaction in the presence of a strong acid selected from the group consisting of oleum, sulfuric acid, trifluoromethanesulfonic acid, methanesulfonic acid and toluenesulfonic acid; the amount of said strong acid being in the range of from about 1.3 to about 5 moles for each mole of said dicarboxylic acid present in the reaction mixture, and intimately dispersing throughout said aqueous phase a sufficient quantity of an inert, water-immiscible solvent for the diperoxycarboxylic acid to selectively remove from said aqueous phase the diperoxycarboxylic acid as it is formed said solvent having been mixed with the carboxylic acid and the strong acid prior to the addition of the hydrogen peroxide; adding water to the reaction mixture at the conclusion of the reaction; distilling off the water-immiscible solvent at a temperature below the decomposition temperature of the diperoxycarboxylic acid and separating the diperoxycarboxylic acid crystals from the residual aqueous phase.

Claim 31

The process of claim 24 wherein the strong acid is 96% sulfuric acid.

Claim 32

The method of claim 24 wherein said diperoxycarboxylic acid is diperoxydodecanedioic acid.

Claim 33

The process of claim 24 wherein said diperoxycarboxylic acid is diperoxyazelaic acid.

Claim 34

The process of claim 24 wherein said diperoxycarboxylic acid is diperoxysebacic acid.

Claim 35

The method of claim 24 wherein said diperoxycarboxylic acid is diperoxytetradecanedioic acid.

Claim 36

The process of claim 24 wherein said reaction is carried out in the refluxing temperature of the water-immiscible solvent.

Claim 37

The process of claim 23 wherein said immiscible solvent is carbon tetrachloride.

Claim 38

The process of claim 23 wherein said immiscible solvent is 1,2-dichloroethane.

Claim 39

The process of claim 23 wherein said immiscible solvent is 1,1,2,2-tetrachloroethane.

Claim 40

The process of claim 23 wherein said immiscible solvent is trichloro-trifluoro ethane.

Claim 41

The process of claim 23 wherein said immiscible solvent is methylene chloride.

Claim 42

The process of claim 5 wherein the strong acid is 5% oleum.

Claim 43

The process of claim 6 wherein the strong acid is 5% oleum.

Claim 44

The process of claim 19 wherein the strong acid is 5% oleum.

Claim 45

The process of claim 24 wherein the strong acid is 5% oleum.

Claim 46

The process of claim 5 wherein the strong acid is 10% oleum.

Claim 47

The process of claim 6 wherein the strong acid is 10% oleum.