GB1111892A - Process for preparing an oxime or a hydroxylamine - Google Patents
Process for preparing an oxime or a hydroxylamineInfo
- Publication number
- GB1111892A GB1111892A GB6855/66A GB685566A GB1111892A GB 1111892 A GB1111892 A GB 1111892A GB 6855/66 A GB6855/66 A GB 6855/66A GB 685566 A GB685566 A GB 685566A GB 1111892 A GB1111892 A GB 1111892A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenylethanol
- amine
- hydroperoxide
- hydroperoxides
- carried out
- 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
- 150000002923 oximes Chemical class 0.000 title abstract 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N 4-isopropylbenzyl alcohol Chemical compound CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000002432 hydroperoxides Chemical class 0.000 abstract 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- -1 aralkenyl Chemical group 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- GUQRKZPMVLRXLT-UHFFFAOYSA-N n-cyclohexylhydroxylamine Chemical compound ONC1CCCCC1 GUQRKZPMVLRXLT-UHFFFAOYSA-N 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- HBGGBCVEFUPUNY-UHFFFAOYSA-N cyclododecanamine Chemical compound NC1CCCCCCCCCCC1 HBGGBCVEFUPUNY-UHFFFAOYSA-N 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 abstract 1
- 150000002443 hydroxylamines Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
- C07C15/46—Styrene; Ring-alkylated styrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cumene and ethylbenzene are obtained by hydrogenating cumyl alcohol and a -phenylethanol respectively. Isobutylene, styrene and a -methyl-styrene are obtained by dehydrating t-butyl alcohol, a -phenylethanol and cumyl alcohol respectively over a dehydration catalyst, e.g. titania, silica or alumina.ALSO:Oximes and hydroxylamines are obtained from the corresponding primary amine, the amine group of which is attached to a primary or secondary saturated carbon atom, by treating the amine in the liquid phase with a combination of a dissolved metal catalyst selected from organic titanates and an organic hydroperoxide as the essential oxidizing agent. The amount of oxidizing agent is in the range of 0.01 to 10 mols per mol of amine, and the amount of metal is in the range of 0.00001 to 0.1 mols per mol of hydroperoxide. The preferred reaction temperature is in the range of about - 10 DEG to + 175 DEG C. Specified organic hydroperoxides are those of the formula ROOH wherein R is an aralkyl, aralkenyl, hydroxyalkyl, hydroxyaralkyl, cycloalkyl, cycloalkenyl, hydroxycycloalkyl or alkyl group having 3 to 20 carbon atoms. Analogous hydroxy-hydroperoxides may also be used. Specified amines are those which contain 1 to 20 carbon atoms such as benzylamine, isopropylamine, cyclohexylamine, and cyclododecylamine. The process may be carried out in the presence of an inert solvent and in the substantial absence of water. The reaction is carried out under a pressure sufficient to maintain a liquid reaction phase. The process may be carried out starting with the hydrocarbon from which the hydroperoxide is derived and oxidizing the hydrocarbon e.g. with molecular oxygen in the first step. Cyclohexyl hydroxylamine may be prepared and air oxidized to the oxime. Examples are given for the preparation of cyclohexyl hydroxylamine and cyclohexanone oxime. Alcohols are obtained as by-products in the above reaction from the corresponding hydroperoxides. Specified alcohols being cumyl alcohol, a -phenylethanol and t-butanol. Also acetophenone may be obtained by dehydrogenating the by-product a -phenylethanol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35548564A | 1964-03-27 | 1964-03-27 | |
| US43408965A | 1965-02-19 | 1965-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111892A true GB1111892A (en) | 1968-05-01 |
Family
ID=26998874
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12465/65A Expired GB1100672A (en) | 1964-03-27 | 1965-03-24 | Process for preparing an oxime or a hydroxylamine |
| GB6855/66A Expired GB1111892A (en) | 1964-03-27 | 1966-02-16 | Process for preparing an oxime or a hydroxylamine |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12465/65A Expired GB1100672A (en) | 1964-03-27 | 1965-03-24 | Process for preparing an oxime or a hydroxylamine |
Country Status (6)
| Country | Link |
|---|---|
| BE (2) | BE661500A (en) |
| CH (1) | CH439262A (en) |
| DE (1) | DE1518981A1 (en) |
| GB (2) | GB1100672A (en) |
| LU (2) | LU48273A1 (en) |
| NL (2) | NL6503548A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2505580A1 (en) * | 2011-03-28 | 2012-10-03 | Sumitomo Chemical Company, Limited | Method for producing oxime |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960954A (en) * | 1968-05-27 | 1976-06-01 | Halcon International, Inc. | Process for preparing oximes and hydroxylamines |
| CN107115875B (en) * | 2017-06-29 | 2019-11-12 | 湘潭大学 | A kind of preparation method and application of titanium phosphorus oxygen catalyst |
-
1965
- 1965-03-19 NL NL6503548A patent/NL6503548A/xx unknown
- 1965-03-23 BE BE661500A patent/BE661500A/xx unknown
- 1965-03-24 GB GB12465/65A patent/GB1100672A/en not_active Expired
- 1965-03-26 LU LU48273A patent/LU48273A1/xx unknown
- 1965-03-26 CH CH421965A patent/CH439262A/en unknown
- 1965-03-27 DE DE1965H0055615 patent/DE1518981A1/en active Pending
- 1965-08-26 BE BE668811A patent/BE668811A/xx unknown
- 1965-08-31 LU LU49420A patent/LU49420A1/xx unknown
- 1965-09-02 NL NL6511461A patent/NL6511461A/xx unknown
-
1966
- 1966-02-16 GB GB6855/66A patent/GB1111892A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2505580A1 (en) * | 2011-03-28 | 2012-10-03 | Sumitomo Chemical Company, Limited | Method for producing oxime |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6511461A (en) | 1966-08-22 |
| NL6503548A (en) | 1965-09-28 |
| BE661500A (en) | 1965-09-23 |
| BE668811A (en) | 1966-02-28 |
| DE1518981A1 (en) | 1969-11-27 |
| GB1100672A (en) | 1968-01-24 |
| CH439262A (en) | 1967-07-15 |
| LU49420A1 (en) | 1967-03-01 |
| LU48273A1 (en) | 1966-09-26 |
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