NO117076B - - Google Patents
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- Publication number
- NO117076B NO117076B NO153247A NO15324764A NO117076B NO 117076 B NO117076 B NO 117076B NO 153247 A NO153247 A NO 153247A NO 15324764 A NO15324764 A NO 15324764A NO 117076 B NO117076 B NO 117076B
- Authority
- NO
- Norway
- Prior art keywords
- lactam
- hydrogen chloride
- reaction
- hydrochloride
- oxime
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 28
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 28
- 150000003951 lactams Chemical class 0.000 claims description 27
- -1 lactam hydrochloride Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 11
- 230000008707 rearrangement Effects 0.000 claims description 7
- 239000000375 suspending agent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 24
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 15
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 10
- 150000002923 oximes Chemical class 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- FRXOYYBDUSFAGK-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane Chemical compound ClN1CN(Cl)CN(Cl)C1 FRXOYYBDUSFAGK-UHFFFAOYSA-N 0.000 description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WVQMNVHWDSLKKT-UHFFFAOYSA-N n-cyclohexylidenehydroxylamine;hydrochloride Chemical compound Cl.ON=C1CCCCC1 WVQMNVHWDSLKKT-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PWXIKGAMKWRXHD-UHFFFAOYSA-N 3-butylaziridin-2-one Chemical compound CCCCC1NC1=O PWXIKGAMKWRXHD-UHFFFAOYSA-N 0.000 description 1
- LHNFFCJQGALMQI-UHFFFAOYSA-N 7-chloro-3,4,5,6-tetrahydro-2h-azepine Chemical compound ClC1=NCCCCC1 LHNFFCJQGALMQI-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- OENGSNXUALAIFP-UHFFFAOYSA-N n-cycloheptylidenehydroxylamine Chemical compound ON=C1CCCCCC1 OENGSNXUALAIFP-UHFFFAOYSA-N 0.000 description 1
- KTPUHSVFNHULJH-UHFFFAOYSA-N n-cyclooctylidenehydroxylamine Chemical compound ON=C1CCCCCCC1 KTPUHSVFNHULJH-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 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
- C07D201/04—Preparation of lactams from or via oximes by Beckmann rearrangement
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL292749 | 1963-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO117076B true NO117076B (da) | 1969-06-30 |
Family
ID=19754700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO153247A NO117076B (da) | 1963-05-15 | 1964-05-13 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3437655A (da) |
| AT (1) | AT252895B (da) |
| BE (1) | BE647780A (da) |
| BR (1) | BR6459203D0 (da) |
| CH (1) | CH449021A (da) |
| DK (1) | DK121024B (da) |
| ES (1) | ES299784A1 (da) |
| GB (1) | GB1052284A (da) |
| NL (1) | NL292749A (da) |
| NO (1) | NO117076B (da) |
| SE (1) | SE322218B (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541080A (en) * | 1966-07-28 | 1970-11-17 | Toray Industries | Process for preparing lactam hydrochloride and a free base thereof |
| US3609142A (en) * | 1966-10-14 | 1971-09-28 | Phillips Petroleum Co | Beckmann rearrangement of cyclic ketoximes to lactams |
| NL6910429A (da) * | 1969-07-08 | 1971-01-12 | ||
| JPS5217034B2 (da) * | 1972-09-08 | 1977-05-12 | ||
| ES2426368T3 (es) * | 2007-02-09 | 2013-10-22 | National University Corporation Nagoya University | Método para la producción de laurolactama |
| JP5446872B2 (ja) * | 2007-11-29 | 2014-03-19 | 宇部興産株式会社 | ラウロラクタムの製造方法 |
| JP5447502B2 (ja) | 2009-03-04 | 2014-03-19 | 宇部興産株式会社 | アミド化合物の製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3094520A (en) * | 1963-06-18 | Process for producing lactams | ||
| US3167542A (en) * | 1965-01-26 | Production of caprylic lactam | ||
| US2883377A (en) * | 1959-04-21 | Production of lactams from oxime | ||
| US2249177A (en) * | 1941-07-15 | Rearrangement reaction of oxevies | ||
| US2234566A (en) * | 1938-07-23 | 1941-03-11 | Du Pont | Catalytic process for the production of caprolactam, amino-capronitrile and hexamethylene diamine |
-
0
- GB GB1052284D patent/GB1052284A/en active Active
- NL NL292749D patent/NL292749A/xx unknown
-
1964
- 1964-05-11 BE BE647780D patent/BE647780A/xx unknown
- 1964-05-11 CH CH609264A patent/CH449021A/de unknown
- 1964-05-12 AT AT415864A patent/AT252895B/de active
- 1964-05-13 US US367212A patent/US3437655A/en not_active Expired - Lifetime
- 1964-05-13 SE SE5882/64A patent/SE322218B/xx unknown
- 1964-05-13 ES ES299784A patent/ES299784A1/es not_active Expired
- 1964-05-13 NO NO153247A patent/NO117076B/no unknown
- 1964-05-14 DK DK242264AA patent/DK121024B/da unknown
- 1964-05-14 BR BR159203/64A patent/BR6459203D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1470327A1 (de) | 1969-08-07 |
| GB1052284A (da) | |
| DE1470327B2 (de) | 1975-08-28 |
| BR6459203D0 (pt) | 1973-08-07 |
| AT252895B (de) | 1967-03-10 |
| NL292749A (da) | |
| DK121024B (da) | 1971-08-23 |
| BE647780A (da) | 1964-11-12 |
| US3437655A (en) | 1969-04-08 |
| CH449021A (de) | 1967-12-31 |
| SE322218B (da) | 1970-04-06 |
| ES299784A1 (es) | 1964-08-16 |
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