CA1052784A - Procede de preparation des lactames a partir d'oximes correspondantes - Google Patents
Procede de preparation des lactames a partir d'oximes correspondantesInfo
- Publication number
- CA1052784A CA1052784A CA232,550A CA232550A CA1052784A CA 1052784 A CA1052784 A CA 1052784A CA 232550 A CA232550 A CA 232550A CA 1052784 A CA1052784 A CA 1052784A
- Authority
- CA
- Canada
- Prior art keywords
- oxime
- solution
- solvent
- alicyclic
- group
- 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
- 150000003951 lactams Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 13
- 150000002923 oximes Chemical class 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- -1 alicyclic oximes Chemical class 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 8
- 238000009835 boiling Methods 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 238000004821 distillation Methods 0.000 claims abstract description 6
- 230000007935 neutral effect Effects 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 150000001805 chlorine compounds Chemical class 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 239000011593 sulfur Substances 0.000 claims abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 4
- 239000011574 phosphorus Substances 0.000 claims abstract description 4
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- 150000001925 cycloalkenes Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 5
- 230000017105 transposition Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000002955 isolation Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- FXTTXRHGRZVUAG-UHFFFAOYSA-N P.Cl.Cl.Cl.Cl.Cl Chemical compound P.Cl.Cl.Cl.Cl.Cl FXTTXRHGRZVUAG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XSIDCAOQNLRQEL-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine;hydrochloride Chemical compound Cl.ON=C1CCCCCCCCCCC1 XSIDCAOQNLRQEL-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000003716 rejuvenation Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7426702A FR2283128A1 (fr) | 1974-08-01 | 1974-08-01 | Procede de preparation des lactames a partir d'oximes correspondantes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052784A true CA1052784A (fr) | 1979-04-17 |
Family
ID=9141968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,550A Expired CA1052784A (fr) | 1974-08-01 | 1975-07-30 | Procede de preparation des lactames a partir d'oximes correspondantes |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5141376A (esLanguage) |
| BE (1) | BE831948A (esLanguage) |
| CA (1) | CA1052784A (esLanguage) |
| CH (1) | CH609044A5 (esLanguage) |
| DE (1) | DE2534538C3 (esLanguage) |
| FR (1) | FR2283128A1 (esLanguage) |
| GB (1) | GB1467565A (esLanguage) |
| IT (1) | IT1045041B (esLanguage) |
| LU (1) | LU73102A1 (esLanguage) |
| NL (1) | NL168508C (esLanguage) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3538859A1 (de) * | 1985-11-02 | 1987-05-07 | Huels Chemische Werke Ag | Verfahren zum herstellen von lactamen mit 8 bis 15 kohlenstoffatomen aus den entsprechenden oximen |
| JP3200292B2 (ja) * | 1994-08-05 | 2001-08-20 | 三菱鉛筆株式会社 | 焼成色鉛筆芯及びその製造方法 |
| JPH08259874A (ja) * | 1995-03-27 | 1996-10-08 | Mitsubishi Pencil Co Ltd | 焼成色鉛筆芯及びその製造方法 |
| EP1312604A1 (en) * | 2001-11-02 | 2003-05-21 | National Institute of Advanced Industrial Science and Technology | Method of production of lactams |
| JP2008162935A (ja) * | 2006-12-28 | 2008-07-17 | Daicel Chem Ind Ltd | アミド又はラクタムの製造法 |
| US8354527B2 (en) | 2008-05-02 | 2013-01-15 | Ube Industries, Ltd. | Process for producing amide or lactam |
| 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 |
| CN102639507B (zh) * | 2009-09-24 | 2014-08-06 | 宇部兴产株式会社 | 新型化合物和使用其制备酰胺化合物的方法 |
| CN105315213B (zh) | 2010-03-15 | 2018-04-20 | 宇部兴产株式会社 | 制备酰胺化合物的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1430780A (fr) * | 1964-04-22 | 1966-03-04 | Stamicarbon | Lactames obtenus à partir de cétoximes cyclo-aliphatiques |
| FR2110716A5 (esLanguage) * | 1970-10-28 | 1972-06-02 | Aquitaine Total Organico |
-
1974
- 1974-08-01 FR FR7426702A patent/FR2283128A1/fr active Granted
-
1975
- 1975-07-28 GB GB3149475A patent/GB1467565A/en not_active Expired
- 1975-07-30 CA CA232,550A patent/CA1052784A/fr not_active Expired
- 1975-07-30 LU LU73102A patent/LU73102A1/xx unknown
- 1975-07-30 JP JP9215775A patent/JPS5141376A/ja active Pending
- 1975-07-31 IT IT2594675A patent/IT1045041B/it active
- 1975-07-31 CH CH1003475A patent/CH609044A5/xx not_active IP Right Cessation
- 1975-07-31 BE BE158791A patent/BE831948A/xx not_active IP Right Cessation
- 1975-08-01 NL NL7509239A patent/NL168508C/xx not_active IP Right Cessation
- 1975-08-01 DE DE19752534538 patent/DE2534538C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2534538A1 (de) | 1976-02-19 |
| GB1467565A (en) | 1977-03-16 |
| IT1045041B (it) | 1980-04-21 |
| JPS5141376A (en) | 1976-04-07 |
| NL7509239A (nl) | 1976-02-03 |
| CH609044A5 (en) | 1979-02-15 |
| LU73102A1 (esLanguage) | 1976-03-02 |
| BE831948A (fr) | 1975-11-17 |
| DE2534538C3 (de) | 1986-03-27 |
| FR2283128B1 (esLanguage) | 1977-03-18 |
| DE2534538B2 (de) | 1979-10-31 |
| NL168508C (nl) | 1982-04-16 |
| NL168508B (nl) | 1981-11-16 |
| FR2283128A1 (fr) | 1976-03-26 |
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