Purification of secondary alkyl amines

Claim 2

A PROCESS FOR SEPARATING SECONDARY ALKYL PRIMARY AMINES CONTAINING 8 TO 40 CARBON ATOMS FROM MIXTURES CONTAINING FROM ABOUT 5 TO 30 PERCENT BY WEIGHT OF SAID AMINES FROM THEIR CONTAMINANTS, INCLUDING INERT NON-POLAR PARAFFINIC CONTAMINANTS BY TREATMENT OF SAID AMINES CONTAINED IN THE MIXTURE WITH CARBON DIOXIDE TO FORM SECONDARY ALKYL PRIMARY AMINECARBON DIOXIDE COMPLEXES, AND EXTRACTING SAID COMPLEXES INTO INERT POLAR SOLVENT SELECTED FROM THE GROUP CONSISTING OF ALKANOLS CONTAINING 1 TO 4 CARBON ATOMS, MIXTURES OF ALKANOLS CONTAINING 1 TO 4 CARBON ATOMS AND MIXTURE OF ALKANOLS CONTAINING 1 TO 4 CARBON ATOMS WITH WATER, SAID PROCESS CONSISTING ESSENTIALLY OF: A. ADMIXING SAID MIXTURE OF SECONDARY ALKYL PRIMARY AMINES AND SAID CONTAMINANTS AT ABOUT 15* TO 100*C UNDER PRESSURES OF CARBON DIOXIDE, RANGING FROM ABOUT 0 PSIG TO 500 PSIG, IN AN AMOUNT AND FOR A TIME SUFFICIENT TO FORM SUBSTANTIAL AMOUNTS OF SAID AMINE-CARBON DIOXIDE COMPLEXES, IN THE PRESENCE OF SAID INERT POLAR SOLVENT TO FORM TWO PHASES, AN INERT POLAR SOLVENT PHASE WHICH CONTAINS SUBSTANTIALLY ALL OF SAID AMINE-CARBON DIOXIDE COMPLEXES, AND A PARAFFINIC PHASE WHICH CONTAINS SUBSTANTIALLY ALL OF SAID CONTAMINANTS, B. SEPARATING SAID TWO PHASES FROM EACH OTHER AND SPRINGING SAID SECONDARY ALKYL PRIMARY AMINE FROM SAID AMINECARBON DIOXIDE COMPLEXES IN SAID INERT POLAR SOLVENT PHASE.

Claim 3

The process of claim 1 wherein the admixture of amines and contaminants is treated with carbon dioxide in the absence of inert polar solvent until substantially all of said secondary alkyl primary amine present is converted to said complex, then adding the inert polar solvent substantially saturated with carbon dioxide, to from said two phases.

Claim 4

The process of claim 1 wherein the inert polar solvent is saturated with carbon dioxide prior to contacting it with the mixture of secondary alkyl primary amines and contaminants.

Claim 5

The process of claim 1 wherein the admixture of amines and contaminants including paraffinics is treated with carbon dioxide in the absence of said inert polar solvent, and the inert polar solvent is subsequently added to the carbon-dioxide treated mixture of amine-carbon dioxide complexes and contaminants to form the two phases.

Claim 6

A process for separating secondary alkyl primary amines containing 10 to 25 carbon atoms from amine-contaminant mixture including paraffins of 10 to 25 carbon atoms, said mixture containing from about 8 to 20 percent by weight of said amines, by the treatment of the amines contained in the contaminant mixtures with carbon dioxide to form secondary alkyl primary amine-carbon dioxide complexes from the secondary alkyl primary amines contained in said mixtures, followed by preferential extraction into alkanol-water solvents at least partially immiscible with said paraffinic contaminants contained in said mixture, said process consisting essentially of: a. admixing said mixture of secondary alkyl primary amines at about 15* to 50*C at superatmospheric pressures ranging from 100 to 500 psig and treating said admixture with about 1 or more moles of CO2 based upon each mole of said amine present in said admixture until substantial quantities of said amine-carbon dioxide complexes are formed, b. contacting said amine-carbon dioxide complexes and contaminants of said admixture with at least 1 to about 5 parts by weight of an alkanol-water solvent mixture substantially saturated with carbon dioxide, wherein the alkanol contains 1 to 4 carbon atoms, until an alkanol-water solvent phase containing substantially all of said amine-carbon dioxide complex and a contaminant phase containing substantially all of said contaminants is formed, c. separating said solvent phase from said contaminant phase, and d. springing substantially all of the secondary alkyl primary amine contained in said alkanol-water solvent phase.

Claim 7

A process for separating secondary alkyl primary amines containing 10 to 25 carbon atoms from amine-contaminant mixture including paraffins of 10 to 25 carbon atoms, said mixture containing from about 8 to 20 percent by weight of said amines, by the treatment of the amines contained in the contaminant mixtures with carbon dioxide to form secondary alkyl primary amine-carbon dioxide complexes from the secondary alkyl primary amines contained in said mixtures, followed by preferential extraction into alkanol-water solvents at least partially immiscible with said paraffinic contaminants contained in said mixture, said process consisting essentially of: a. admixing said mixture of secondary alkyl primary amines at about 15* to 50*C at superatmospheric pressures ranging from 100 to 500 psig and treating said admixture with about 1 or more moles of CO2 based upon each mole of said amine present in said admixture until substantial quantities of said amine-carbon dioxide complexes are formed, b. contacting said amine-carbon dioxide complexes and contaminants of said admixture with at least 1 to about 5 parts by weight of an alkanol-water solvent mixture substantially saturated with carbon dioxide, wherein the alkanol contains 1 to 4 carbon atoms, until an alkanol-water solvent phase containing substantially all of said amine-carbon dioxide complex and a contaminant phase containing substantially all of said contaminants is formed, c. separating said solvent phase from said contaminant phase, and d. springing substantially all of the secondary alkyl primary amine contained in said alkanol-water solvent phase.

Claim 8

The process of claim 5 wherein the alkanol is methanol.

Claim 9

The process of claim 5 wherein the alkanol is ethanol.

Claim 10

The process of claim 5 wherein the alkanol is a propanol.

Claim 11

The process of claim 5 wherein the alkanol is butanol.

Claim 12

The process of claim 5 wherein the springing is accomplished by heating the complex.

Claim 13

A process for separating secondary alkyl primary amines from a one-phase mixture consisting essentially of about 8 to 20 parts by weight of secondary alkyl primary amine containing 10 to 14 carbon atoms, from 92 to 80 parts by weight of paraffin diluent containing 10 to 14 carbon atoms and from 0 to 12 parts by weight of amine contaminant of said secondary alkyl primary amines, by the treatment of said secondary alkyl primary amines contained in said one-phase mixture with carbon dioxide to form secondary alkyl primary amine-carbon dioxide complexes of said secondary alkyl primary amines contained in said mixtures, followed by preferential extraction into methol-water solvent at least partially immiscible with the paraffinic diluents of said mixture, said process consisting essentially of: a. treating said one-phase mixture of secondary alkyl primary amines and paraffinic diluents containing 10 to 14 carbon atoms, at about 15* to 50*C at pressures ranging from 0 to 525 psig, with about 0.5 to 5.0 moles of CO2 based upon each mole of said amine present in said admixture until substantial quantities of said amine-carbon dioxide complexes are formed, b. contacting said one-phase admixture of amine-carbon dioxide complex, contaminants and paraffinic diluents with from 50 to 500 parts by weight of methanol-water solvent substantially saturated with carbon dioxide until a two phase system is formed, one phase the methanol-water phase containing substantially all of said amine-carbon dioxide complex and the second phase, a contaminant-paraffinic diluent phase containing substantially all of said contaminants initially in the mixture is formed, c. separating said methanol-water phase containing said complex from said contaminant phase, and d. springing substantially all of the secondary alkyl primary amine present as amine-carbon dioxide complex that is contained in said methanol-water phase.

Claim 14

A process for separating secondary alkyl primary amines from a one-phase mixture consisting essentially of about 8 to 20 parts by weight of secondary alkyl primary amine containing 10 to 14 carbon atoms, from 92 to 80 parts by weight of paraffin diluent containing 10 to 14 carbon atoms and from 0 to 12 parts by weight of amine contaminant of said secondary alkyl primary amines, by the treatment of said secondary alkyl primary amines contained in said one-phase mixture with carbon dioxide to form secondary alkyl primary amine-carbon dioxide complexes of said secondary alkyl primary amines contained in said mixtures, followed by preferential extraction into methol-water solvent at least partially immiscible with the paraffinic diluents of said mixture, said process consisting essentially of: a. treating said one-phase mixture of secondary alkyl primary amines and paraffinic diluents containing 10 to 14 carbon atoms, at about 15* to 50*C at pressures ranging from 0 to 525 psig, with about 0.5 to 5.0 moles of CO2 based upon each mole of said amine present in said admixture until substantial quantities of said amine-carbon dioxide complexes are formed, b. contacting said one-phase admixture of amine-carbon dioxide complex, contaminants and paraffinic diluents with from 50 to 500 parts by weight of methanol-water solvent substantially saturated with carbon dioxide until a two phase system is formed, one phase the methanol-water phase containing substantially all of said amine-carbon dioxide complex and the second phase, a contaminant-paraffinic diluent phase containing substantially all of said contaminants initially in the mixture is formed, c. separating said methanol-water phase containing said complex from said contaminant phase, and d. springing substantially all of the secondary alkyl primary amine present as amine-carbon dioxide complex that is contained in said methanol-water phase.

Claim 15

The process of claim 11 wherein the amine in the amine-carbon dioxide complex is sprung by heating the complex between about 60* to 150*C.

Claim 16

The process of claim 11 wherein the secondary alkyl primary amine in the amine-carbon dioxide complex is sprung by depressurizing the amine-carbon dioxide complex.

Claim 17

The process of claim 11 wherein the methanol-water solvent is substantially saturated with carbon dioxide before contacting the secondary alkyl primary amine with carbon dioxide.