← Back to Patent Explorer
US3852273A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing and recovering lactams

Assignee: Stamicarbon BV
•
Filing: 1972-05-02
•
Granted: 1974-12-03
•
Expires: 1992-05-02
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract A process for preparing and recovering lactams by the so-called Beckmann rearrangement of the corresponding ketoximes in a sulfuric acid medium is disclosed, wherein the mixture of lactam and sulfuric acid medium obtained from the Beckmann rearrangement is mixed with an aqueous solution of ammonium sulfate obtained as a by-product in the synthesis of hydroxylammonium sulfate in the preparation of said ketoximes. The lactam is then extracted from the resulting less acidic solution and the remaining acid solution, comprising an aqueous solution of ammonium hydrogen sulfate, is thermally decomposed to produce recoverable sulphur dioxide. The process of this invention can be used in the production of lactams while avoiding the production of ammonium sulfate byproduct.

Inventors

  • 👤 Rooij A H De

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 09:49
CPC Classifications
C; C07; C07D; C07D201/00; C07D201/16; C07D201/02; C07D201/04

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 269 words
A PROCESS FOR PREPARING LACTAMS WITHOUT REQUIRING THE SUBSTANTIAL ADDITION OF DISCHARGE OF SULPHURIC ACID OR OTHER SULFUR-CONTAINING COMPOUNDS TO THE PROCESS, SAID PROCESS COMPRISING THE FOLLOWING STEPS: A. REACTING A FIRST AMOUNT OF SO2, AMMONIUM HYDROXIDE AND AMMONIUM NITRITE TO FORM A SOLUTION OF AMMONIUM HYDROGEN SULFATE AND HYDROXYLAMMONIUM SULFATE, B. NEUTRALIZING THE REACTION MIXTURE IN STEP (A) ABOVE WITH AMMONIA TO FORM A SOLUTION OF AMMONIUM SULFATE AND HYDROXYLAMMONIUM SULFATE, C. REACTING THE NEUTRALIZED PRODUCT OBTAINED IN STEP (B) WITH A KETONE AND ADDITIONAL AMMONIA TO PRODUCE THE CORRESPONDING KETOXIME AND A SOLUTION OF AMMONIUM SULFATE, D. SEPARATING THE KETOXIME FROM THE AMMONIUM SULFATE SOLUTION OF STEP (C), E. MAKING OLEUM FROM A SECOND AMOUNT OF SO2, F. SUBJECTING THE OXIME SEPARATED IN STEP (D) TO THE BECKMANN REARRANGEMENT WITH THE OLEUM OF STEP (E) TO PRODUCE A SOLUTION OF LACTAM AND SULFURIC ACID, G. PARTIALLY NEUTRALIZING THE SULPHURIC ACID IN THE SOLUTION OBTAINED IN STEP (F) WITH THE AMMONIUM SULFATE SOLUTION OBTAINED IN STEP (D), WHEREIN THE RATIO OF AMMONIUM SULFATE TO THE SUM OF AMMONIUM SULFATE AND SULPHIRIC ACID IS ABOUT 0.45:1 TO ABOUT 0.63:1, TO PRODUCE A SOLUTION OF LACTAM IN AMMONIUM HYDROEN SULFATE, H. SEPARATING THE REACTION PRODUCT OF STEP (G) INTO LACTAM PRODUCT AND A SOLUTION OF AMMONIUM HYDROGEN SULFATE, I. THERMALLY DECOMPOSING THE SOLUTION OF AMMONIUM HYDROGEN SULFATE IN STEP (H) TO PRODUCE SO2 IN AN AMOUNT WHICH IS SUBSTANTIALLY THE SUM OF SAID FIRST AMOUNT AND SAID SECOND AMOUNT, J. RECYCLING SAID FIRST AMOUNT OF SO2 TO STEP (A), AND K. RECYCLING SAID SECOND AMOUNT OF SO2 TO STEP (E).
Claim 2
Dependent Claim 269 words
A PROCESS FOR PREPARING LACTAMS WITHOUT REQUIRING THE SUBSTANTIAL ADDITION OF DISCHARGE OF SULPHURIC ACID OR OTHER SULFUR-CONTAINING COMPOUNDS TO THE PROCESS, SAID PROCESS COMPRISING THE FOLLOWING STEPS: A. REACTING A FIRST AMOUNT OF SO2, AMMONIUM HYDROXIDE AND AMMONIUM NITRITE TO FORM A SOLUTION OF AMMONIUM HYDROGEN SULFATE AND HYDROXYLAMMONIUM SULFATE, B. NEUTRALIZING THE REACTION MIXTURE IN STEP (A) ABOVE WITH AMMONIA TO FORM A SOLUTION OF AMMONIUM SULFATE AND HYDROXYLAMMONIUM SULFATE, C. REACTING THE NEUTRALIZED PRODUCT OBTAINED IN STEP (B) WITH A KETONE AND ADDITIONAL AMMONIA TO PRODUCE THE CORRESPONDING KETOXIME AND A SOLUTION OF AMMONIUM SULFATE, D. SEPARATING THE KETOXIME FROM THE AMMONIUM SULFATE SOLUTION OF STEP (C), E. MAKING OLEUM FROM A SECOND AMOUNT OF SO2, F. SUBJECTING THE OXIME SEPARATED IN STEP (D) TO THE BECKMANN REARRANGEMENT WITH THE OLEUM OF STEP (E) TO PRODUCE A SOLUTION OF LACTAM AND SULFURIC ACID, G. PARTIALLY NEUTRALIZING THE SULPHURIC ACID IN THE SOLUTION OBTAINED IN STEP (F) WITH THE AMMONIUM SULFATE SOLUTION OBTAINED IN STEP (D), WHEREIN THE RATIO OF AMMONIUM SULFATE TO THE SUM OF AMMONIUM SULFATE AND SULPHIRIC ACID IS ABOUT 0.45:1 TO ABOUT 0.63:1, TO PRODUCE A SOLUTION OF LACTAM IN AMMONIUM HYDROEN SULFATE, H. SEPARATING THE REACTION PRODUCT OF STEP (G) INTO LACTAM PRODUCT AND A SOLUTION OF AMMONIUM HYDROGEN SULFATE, I. THERMALLY DECOMPOSING THE SOLUTION OF AMMONIUM HYDROGEN SULFATE IN STEP (H) TO PRODUCE SO2 IN AN AMOUNT WHICH IS SUBSTANTIALLY THE SUM OF SAID FIRST AMOUNT AND SAID SECOND AMOUNT, J. RECYCLING SAID FIRST AMOUNT OF SO2 TO STEP (A), AND K. RECYCLING SAID SECOND AMOUNT OF SO2 TO STEP (E).
Claim 3
Dependent Claim 15 words
Process according to claim 1, wherein said ketone is cyclohexanone and said lactam is caprolactam.
Claim 4
Dependent Claim 66 words
Process according to claim 1 wherein a portion of the gas containing sulphur dioxide is cooled, with water vapor condensation, and then washed with a solution of the hydroxylamine disulphonic acid intermediate product from the hydroxylammonium sulphate synthesis, and thereafter the resulting gas having a molar ratio of SO2:H2O greater than 1:1 is utilized for the preparation of sulphuric acid or oleum for the Beckmann rearrangement.
Claim 5
Dependent Claim 52 words
Process accoRding to claim 1 wherein a part of said gas is, after cooling with water vapor condensation, washed, with water vapor condensation, with a solution of ammonium hydrogen sulphate, to produce a gas having a molar ratio of SO2:H2O greater than 1:1, which is used to prepare oleum or sulphuric acid.
Claim 6
Dependent Claim 14 words
The process according to claim 4 wherein said molar ratio is at least 1.5:1.

References Cited (Backward Citations)

US3133055A Cited
US3275407A Cited
DE1206404B Cited
US3292996A Cited
US3321275A Cited
US3383170A Cited
US3336298A Cited
US3404947A Cited
US3694433A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1977-12-02 1978-06-03 1978-12-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1981-12-02 1982-06-03 1982-12-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1985-12-02 1986-06-03 1986-12-03 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag