GB1134851A - Improvements relating to the production of n-hydroxy compounds - Google Patents
Improvements relating to the production of n-hydroxy compoundsInfo
- Publication number
- GB1134851A GB1134851A GB1435065A GB1435065A GB1134851A GB 1134851 A GB1134851 A GB 1134851A GB 1435065 A GB1435065 A GB 1435065A GB 1435065 A GB1435065 A GB 1435065A GB 1134851 A GB1134851 A GB 1134851A
- Authority
- GB
- United Kingdom
- Prior art keywords
- azeotrope
- oxide
- water
- preferred
- alkyl
- 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
- 150000001204 N-oxides Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000001336 alkenes Chemical class 0.000 abstract 2
- 150000002443 hydroxylamines Chemical class 0.000 abstract 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- PAZXUKOJTOTKBK-UHFFFAOYSA-N n,n-dibutylhydroxylamine Chemical compound CCCCN(O)CCCC PAZXUKOJTOTKBK-UHFFFAOYSA-N 0.000 abstract 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 abstract 1
- MXXMJJSIJDMYJZ-UHFFFAOYSA-N n-(2-phenylethyl)hydroxylamine Chemical compound ONCCC1=CC=CC=C1 MXXMJJSIJDMYJZ-UHFFFAOYSA-N 0.000 abstract 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Landscapes
- Hydrogenated Pyridines (AREA)
Abstract
1,134,851. Hydroxylamines. NATIONAL RESEARCH DEVELOPMENT CORP. 25 March, 1966 [5 April, 1965], No. 14350/65. Heading C2C. Hydroxylamines of the formula R<SP>1</SP>R<SP>2</SP>N-OH, where R<SP>1</SP> and R<SP>2</SP> are alkyl or aryl groups or together with the nitrogen atom represent a 5- or 6-membered heterocyclic ring, which may contain other hetero atoms, are made by oxidizing a tertiary amine of the formula R<SP>1</SP>R<SP>2</SP>N-Y, where Y is an alkyl or cycloalkyl group of 2 or more carbon atoms, with hydrogen peroxide to form a water-containing N-oxide and heating the N-oxide with an inert solvent which forms an azeotrope with water and so distilling-off the water as an azeotrope and decomposing the N-oxide to form the hydroxylamine and the olefin corresponding to Y. It is preferred to use an inert azeotrope-forming solvent having a boiling- point sufficiently high to enable the olefin elimination reaction to proceed during the distillation of the azeotrope. Solvents boiling in the range 90-130‹ C. are preferred. Preferred reactants are those in which Y is a C 2-4 alkyl group, e.g. ethyl. Examples relate to the preparation of N-hydroxypiperidine, dibutylhydroxylamine,dimethylhydroxylamine, N - hydroxymorpholine and phenylethylhydroxylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1435065A GB1134851A (en) | 1965-04-05 | 1965-04-05 | Improvements relating to the production of n-hydroxy compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1435065A GB1134851A (en) | 1965-04-05 | 1965-04-05 | Improvements relating to the production of n-hydroxy compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1134851A true GB1134851A (en) | 1968-11-27 |
Family
ID=10039616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1435065A Expired GB1134851A (en) | 1965-04-05 | 1965-04-05 | Improvements relating to the production of n-hydroxy compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1134851A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5144075A (en) * | 1991-01-17 | 1992-09-01 | Ciba-Geigy Corporation | Process for the preparation of n,n-dihydrocarbylhydroxylamines |
| CN116947684A (en) * | 2023-06-14 | 2023-10-27 | 中国原子能科学研究院 | A purification process of N,N-dimethylhydroxylamine |
| CN117342973A (en) * | 2022-06-28 | 2024-01-05 | 中国石油化工股份有限公司 | A method for preparing dihydroxypropylhydroxylamine |
-
1965
- 1965-04-05 GB GB1435065A patent/GB1134851A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5144075A (en) * | 1991-01-17 | 1992-09-01 | Ciba-Geigy Corporation | Process for the preparation of n,n-dihydrocarbylhydroxylamines |
| CN117342973A (en) * | 2022-06-28 | 2024-01-05 | 中国石油化工股份有限公司 | A method for preparing dihydroxypropylhydroxylamine |
| CN117342973B (en) * | 2022-06-28 | 2025-12-12 | 中国石油化工股份有限公司 | A method for preparing dihydroxypropyl hydroxylamine |
| CN116947684A (en) * | 2023-06-14 | 2023-10-27 | 中国原子能科学研究院 | A purification process of N,N-dimethylhydroxylamine |
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