CH391710A - Verfahren zur Herstellung von w-Lactamen - Google Patents

Verfahren zur Herstellung von w-Lactamen

Info

Publication number: CH391710A
Authority: CH; Switzerland
Prior art keywords: acid; lactams; ring; temperature; cycloalkanecarboxylic
Prior art date: 1961-05-10

Application number

CH551161A

Other languages

German (de)

English (en)

Inventor

Clau Dr Berther

Original Assignee

Inventa Ag

Priority date (The priority date 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 date listed.)

1961-05-10

Filing date

1961-05-10

Publication date

1965-05-15

1961-05-10 Application filed by Inventa Ag filed Critical Inventa Ag

1961-05-10 Priority to CH551161A priority Critical patent/CH391710A/de

1962-02-28 Priority to ES0275027A priority patent/ES275027A1/es

1962-03-02 Priority to DK98262AA priority patent/DK109693C/da

1962-03-19 Priority to SE3046/62A priority patent/SE307951B/xx

1962-03-30 Priority to BE615831A priority patent/BE615831A/fr

1962-05-07 Priority to GB17487/62A priority patent/GB1003577A/en

1965-05-15 Publication of CH391710A publication Critical patent/CH391710A/de

Links

238000000034 method Methods 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
150000003951 lactams Chemical class 0.000 claims description 5
230000008707 rearrangement Effects 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000006237 Beckmann rearrangement reaction Methods 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000001924 cycloalkanes Chemical class 0.000 description 2
JWIPDQOXAJMVHL-UHFFFAOYSA-N cyclododecanecarboxylic acid Chemical compound OC(=O)C1CCCCCCCCCCC1 JWIPDQOXAJMVHL-UHFFFAOYSA-N 0.000 description 2
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
URAXDCBRCGSGAT-UHFFFAOYSA-N cyclooctanecarboxylic acid Chemical compound OC(=O)C1CCCCCCC1 URAXDCBRCGSGAT-UHFFFAOYSA-N 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
239000004157 Nitrosyl chloride Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
-1 caprylic lactam Chemical class 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
229910002090 carbon oxide Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
150000003950 cyclic amides Chemical class 0.000 description 1
150000001925 cycloalkenes Chemical class 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
238000007034 nitrosation reaction Methods 0.000 description 1
VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
235000019392 nitrosyl chloride Nutrition 0.000 description 1
VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
239000001272 nitrous oxide Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007157 ring contraction reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000007306 turnover Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/02—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH551161A 1961-05-10 1961-05-10 Verfahren zur Herstellung von w-Lactamen CH391710A (de)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
CH551161A CH391710A (de)	1961-05-10	1961-05-10	Verfahren zur Herstellung von w-Lactamen
ES0275027A ES275027A1 (es)	1961-05-10	1962-02-28	Procedimiento para la prepaciën de omega-lactamos
DK98262AA DK109693C (da)	1961-05-10	1962-03-02	Fremgangsmåde til fremstilling af ω-lactamer.
SE3046/62A SE307951B (da)	1961-05-10	1962-03-19
BE615831A BE615831A (fr)	1961-05-10	1962-03-30	Procédé de préparation de omega-lactames
GB17487/62A GB1003577A (en)	1961-05-10	1962-05-07	Process for the manufacture of omega-lactams

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH551161A CH391710A (de)	1961-05-10	1961-05-10	Verfahren zur Herstellung von w-Lactamen

Publications (1)

Publication Number	Publication Date
CH391710A true CH391710A (de)	1965-05-15

Family

ID=4294836

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH551161A CH391710A (de)	1961-05-10	1961-05-10	Verfahren zur Herstellung von w-Lactamen

Country Status (5)

Country	Link
BE (1)	BE615831A (da)
CH (1)	CH391710A (da)
DK (1)	DK109693C (da)
ES (1)	ES275027A1 (da)
SE (1)	SE307951B (da)

1961
- 1961-05-10 CH CH551161A patent/CH391710A/de unknown
1962
- 1962-02-28 ES ES0275027A patent/ES275027A1/es not_active Expired
- 1962-03-02 DK DK98262AA patent/DK109693C/da active
- 1962-03-19 SE SE3046/62A patent/SE307951B/xx unknown
- 1962-03-30 BE BE615831A patent/BE615831A/fr unknown

Also Published As

Publication number	Publication date
SE307951B (da)	1969-01-27
BE615831A (fr)	1962-07-16
DK109693C (da)	1968-06-10
ES275027A1 (es)	1962-05-01

Publication	Publication Date	Title
CH391710A (de)	1965-05-15	Verfahren zur Herstellung von w-Lactamen
US2883377A (en)	1959-04-21	Production of lactams from oxime
CH397650A (de)	1965-08-31	Verfahren zur Herstellung von Oximinoketonen
CH627430A5 (en)	1982-01-15	Process for preparing alpha -ketocarboxylic acids
DE2110439B2 (de)	1974-09-05	Verfahren zur Herstellung von Aceto-, Diphenylaceto- oder Benzonitril
DE741038C (de)	1943-11-03	Verfahren zur Herstellung von Lactamen
AT233545B (de)	1964-05-11	Verfahren zur Herstellung von ω-Lactamen
AT401174B (de)	1996-07-25	Verfahren zur herstellung von 5h-dibenz-(b,f)-azepin-5-carboxamid
GB740891A (en)	1955-11-23	Improvements in the production of amides
DE929368C (de)	1955-06-27	Verfahren zur Herstellung von Acrylsaeure
AT209325B (de)	1960-05-25	Verfahren zur Herstellung des ß-Hydromuconsäure-Halbnitrils und dessen Ester
US3637761A (en)	1972-01-25	Process for the preparation of high purity trimellitic anhydride from trimellitic acid by the chemical reduction of nitro-compound impurities prior to dehydration and distillation
DE2301206A1 (de)	1974-07-18	Verfahren zur herstellung von omegaureidocarbonsaeuren
DE930445C (de)	1955-07-18	Verfahren zur Herstellung von ªŠ-Caprolactam
DE881647C (de)	1953-07-02	Verfahren zur Herstellung von Dicarbonsaeuren, insbesondere Adipinsaeure
DE1192650B (de)	1965-05-13	Verfahren zur Herstellung von eta-Capryllactam
DE1670781A1 (de)	1970-12-23	Verfahren zur Herstellung von Lactamen
CH334311A (de)	1958-11-30	Verfahren zur Herstellung von e-Caprolactam
DE1620478C3 (de)	1976-11-11	Verfahren zur Herstellung von omega-Laurinolactam
AT255399B (de)	1967-07-10	Verfahren zur Herstellung von substituierten oder unsubstituierten Adipinsäuren
DE1136690B (de)	1962-09-20	Verfahren zur Herstellung von 2, 6-Dichlorbenzonitril
US3341590A (en)	1967-09-12	Process for preparing oximes
DE977706C (de)	1968-07-11	Verfahren zur Herstellung von 1, 3, 5-Trinitro-2, 4, 6-Trichlorbenzol
DE2351219C3 (de)	1977-09-08	Verfahren zur Herstellung von Hydrazonen
CH402870A (de)	1965-11-30	Verfahren zur Herstellung von Dodecyllactam