Back to results
US 2005/0033083 A1Published application
Process for the synthesis of iodopropynyl butylcarbamate in an aqueous solution of a suitable surfactant
AssigneeH & S Chemical Company, Inc.
InventorsDavid Schneider, Charles Schneider, Kurt Jones, Martin Heineke
Life of this patent
Estimating the term…
Abstract
A process for the manufacture of iodopropynyl butylcarbamate (IPBC) is disclosed wherein the subject reaction is carried out in an aqueous solution of a suitable surfactant. The iodination reactant is metallic iodide salt which serves as a donor of I+ ions. The I+ ion is generated on an as needed basis, during the reaction sequence, hence the formation of undesirable isomers of IPBC are minimized. The process of this invention produces a highly purified IPBC having, preferably, a low moisture content (wet-cake). The IPBC produced by such a process is also disclosed herein.
Claims14
A process for producing 3-iodo-2-propynyl butylcarbamate which comprises reacting propynyl butylcarbamate with a source of the iodide+ion, wherein the reaction is carried out in an aqueous solution of a nonionic surfactant.
A process for the production of IPBC, which comprises the steps of:
- a. charging a reactor with an aqueous solution of a nonionic surfactant,
- b. cooling the reaction mass to a temperature of less than about 12° C.,
- c. adding to the reaction mass an aqueous solution of a metallic iodide salt,
- d. adjusting the pH of the reaction mass to greater than 7 with a molar excess of a akali metal hydroxide, wherein the molar excess is based on the propynyl butylcarbamate to be added,
- e. charging the reaction mass with an effective amount of propynyl butylcarbamate,
- f. charging the reaction mass with a solution of an oxidizing agent while maintaining the temperature at less than about 11° C.,
- g. agitating the reaction mass for an effective period of time and, during this period, allowing the temperature of the reaction mass to ramp up to a temperature of about 20° C.,
- h. ramping the temperature of the reaction mass up to a temperature of less than about 40° C.,
- i. adjusting the pH with an organic acid such that the pH of the reaction mass is slightly acidic,
- j. adjusting the pH to about 6.6,
- k. ramping the temperature of the reaction mass up to a temperature of less than 59° C.,
- l. ramping the temperature down to a temperature of about 25 to about 30° C.,
- m. ramping, with agitation, the temperature of the reaction mass down to room temperature,
- n. filtering and washing the reaction mass with water and drying to a constant weight.
11 more elements
A process for the production of 3-iodo-2 propynyl butylcarbamate which comprises the steps of:
- a. charging a reaction vessel with an aqueous solution of a nonionic surfactant wherein the concentration of the nonionic surfactant is from about 15 to about 20 weight percent of the below set forth propynyl butylcarbamate charge,
- b. cooling the solution to a temperature of from about 0 to about 8° C.,
- c. adding to the reaction mass from about 1.0 to about 1.03 weight percent of an iodide metal salt which is a member selected from the group consisting of sodium iodide and potassium iodide,
- d. adjusting the pH of the reaction mass to greater than 7 with an alkali metal hydroxide and providing an excess of from about 0.8 to about 1.0 moles of alkali based on the n-propynyl butylcarbamate to be added,
- e. while stirring, adding to the reaction mass from about 1 mole weight percent of n-propynyl butylcarbamate while maintaining the temperature of the reaction mass at from about 0 to about 8° C.,
- f. while stirring, charging the reaction mass with from about 1.1 to about 1.3 mole percent of sodium hypochlorite, while maintaining the temperature at from about 6 to about 11° C.,
- g. allowing the temperature of the reaction mass to ramp up to from about 15 to about 20° C. and continue the agitation for a period of time of from about 60 to about 120 minutes,
- h. ramping the temperature up to from about 35 to about 40° C. at a rate of from about 0.25 to about 0.75 degrees per minute,
- i. adjusting the pH of the reaction mass to about 6.9 with acetic acid,
- j. adjusting the pH to about 6.6 with sodium bisulfite,
- k. ramping the temperature up to a temperature of from about 55 to about 59° C. at a rate of from about 0.25 to about 0.75 degrees per minute,
- l. ramping the temperatures of the reaction mass down to a temperature of from about 25 to about 30° C. at a rate of from about 0.35 to about 0.75 degrees per minute,
- m. washing the reaction mass with water, and
- n. drying the reaction mass at a temperature of from about 25 to about 45° C. to a constant weight.
11 more elements
A process for the production of 3-iodo-2-propynyl butylcarbamate comprising the steps of:
- a. charging a reaction vessel with an aqueous solution of a nonionic surfactant wherein the concentration of the nonionic surfactant is from about 15 to about 20 weight percent of the below set forth propynyl butylcarbamate charge,
- b. cooling the solution to a temperature of from about 0 to about 8° C.,
- c. adding to the reaction mass from about 1.0 to about 1.03 weight percent of an iodide metal salt which is a member selected from the group consisting of sodium iodide and potassium iodide,
- d. adjusting the pH of the reaction mass to greater than 7 with an alkali metal hydroxide and providing an excess of from about 0.8 to about 1.0 moles of alkali based on the n-propynyl butylcarbamate to be added,
- e. while stirring, adding to the reaction mass from about 1 mole percent of n-propynyl butylcarbamate while maintaining the temperature from about 6 to about 11° C.,
- f. while stirring, charging the reaction mass with from about 1.1 to about 1.3 mole percent of sodium hypochlorite, while maintaining the temperature at from about 6 to about 11° C.,
- g. allowing the temperature of the reaction mass to ramp up from about 15 to about 20° C. and continuing the stirring for a period of time of from about 60 to about 120 minutes,
- h. ramping the temperature up to from about 35 to about 40° C., at a rate of from about 0.25 to about 0.75 degrees per minute,
- i. adjusting the pH of the reaction mass to about 6.9 with acetic acid,
- j. adjusting the pH to about 6.6 with sodium bisulfite,
- k. ramping the temperature up to a temperature from about 55 to about 59° C. at a rate of from about 0.25 to about 0.75 degrees per minute,
- l. ramping the temperatures of the reaction mass down to a temperature from about 25 to about 30° C. at a rate of from about 0.35 to about 0.75 degrees per minute,
- m. washing the reaction mass with water, and
- n. drying the reaction mass at a temperature from about 25 to about 45° C. to a constant weight.
11 more elements
Dependencies are inferred from the claim text.