GB942968A - Improvements in the production of epsilon-caprolactam - Google Patents
Improvements in the production of epsilon-caprolactamInfo
- Publication number
- GB942968A GB942968A GB846462A GB846462A GB942968A GB 942968 A GB942968 A GB 942968A GB 846462 A GB846462 A GB 846462A GB 846462 A GB846462 A GB 846462A GB 942968 A GB942968 A GB 942968A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxime
- hydrochloride
- hydrogen chloride
- sulphuric acid
- temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 4
- 150000002923 oximes Chemical class 0.000 abstract 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract 3
- 239000001117 sulphuric acid Substances 0.000 abstract 3
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 abstract 2
- 230000008707 rearrangement Effects 0.000 abstract 2
- 239000002002 slurry Substances 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004157 Nitrosyl chloride Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 abstract 1
- 235000019392 nitrosyl chloride Nutrition 0.000 abstract 1
- -1 oxime hydrochloride Chemical class 0.000 abstract 1
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/10—Preparation of lactams from cycloaliphatic compounds by simultaneous nitrosylation and rearrangement
Abstract
Caprolactam is prepared from a crude, oily hydrochloride of cyclohexanone oxime containing between 1.5 and 2 mols of hydrogen chloride per mol of oxime by stripping hydrogen chloride and volatile impurities from the crude hydrochloride in the presence of a saturated hydrocarbon liquid boiling between 65 DEG C. and 150 DEG C. at atmospheric pressure until between 1 and 1.5 mols of hydrogen chloride per mol of oxime remains and the resulting hydrochloride is crystallisable as a free flowing slurry in the remaining hydrocarbon at 15 DEG to 50 DEG C., cooling and crystallising to a free flowing slurry, mixing with sulphuric acid in a molecular ratio of 1:1 at a temperature at which hydrogen chloride is evolved, separating off the solution of oxime in sulphuric acid and subjecting the oxime to conditions of temperature and time, and a further catalyst if desired, such that Beckmann re-arrangement occurs. Concentrated sulphuric acid is preferably used and is added to the hydrochloride at a temperature between 15 DEG and 45 DEG C., and effecting the Beckmann re-arrangement at 80 DEG to 200 DEG C. The oxime hydrochloride may be obtained by reacting nitrosyl chloride with cyclohexane in the presence of actinic light.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9384161A | 1961-03-07 | 1961-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB942968A true GB942968A (en) | 1963-11-27 |
Family
ID=22241113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB846462A Expired GB942968A (en) | 1961-03-07 | 1962-03-05 | Improvements in the production of epsilon-caprolactam |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH399470A (en) |
| GB (1) | GB942968A (en) |
-
1962
- 1962-03-05 CH CH263862A patent/CH399470A/en unknown
- 1962-03-05 GB GB846462A patent/GB942968A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH399470A (en) | 1965-09-30 |
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