GB938644A - Vapour phase nitration of cyclohexane - Google Patents
Vapour phase nitration of cyclohexaneInfo
- Publication number
- GB938644A GB938644A GB6163/62A GB616362A GB938644A GB 938644 A GB938644 A GB 938644A GB 6163/62 A GB6163/62 A GB 6163/62A GB 616362 A GB616362 A GB 616362A GB 938644 A GB938644 A GB 938644A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexane
- stages
- nitrating agent
- proportion
- added
- 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title abstract 6
- 238000006396 nitration reaction Methods 0.000 title abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 7
- 230000000802 nitrating effect Effects 0.000 abstract 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract 4
- 229910017604 nitric acid Inorganic materials 0.000 abstract 4
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 238000004508 fractional distillation Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 238000010494 dissociation reaction Methods 0.000 abstract 1
- 230000005593 dissociations Effects 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- 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
Mononitrocyclohexane is prepared by passing cyclohexane and nitric acid or nitrogen dioxide in the vapour phase through a reaction zone at 250-375 DEG C. for a period of at least 10 seconds, preferably 10-150 seconds, the proportion of cyclohexane being 4-10 mols, per mol. of nitric acid (calculated as HNO3) or 1-5 mols. per mol. of nitrogen dioxide (calculated as NO2). The cyclohexane and the nitrating agent are preferably mixed in the vapour phase, e.g. at 120-180 DEG C., before they are passed to the reaction zone. The reaction mixture may also contain 0.5-1 mol. of nitric oxide, which may be added to the nitrating agent or to the reaction mixture at any stage before the nitrogen dioxide undergoes appreciable dissociation. The products may be condensed and cyclohexane may be separated therefrom by fractional distillation and returned to the process. The residue may be treated for the recovery of nitrocyclohexane by fractional distillation or conversion to the ammonium salt. The uncondensible portion of the products may be oxidized, e.g. with hydrogen peroxide, to form nitric acid. Alternatively, the process may be effected in stages, e.g. four stages, with addition of fresh nitrating agent between the stages. In this case the proportion of nitrating agent added between the stages may be 0.8-1.2 mols, based on the proportion of nitrating agent added at the first stage, so that the proportion of cyclohexane to nitrating agent may fall below that prescribed for the first stage. Nitric oxide may be added as the nitration agent added between the stages. Examples are given.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89613A US3133123A (en) | 1961-02-16 | 1961-02-16 | Vapor phase nitration of cyclohexane |
| US89652A US3133124A (en) | 1961-02-16 | 1961-02-16 | Multi-stage nitration of cyclohexane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB938644A true GB938644A (en) | 1963-10-02 |
Family
ID=26780766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6163/62A Expired GB938644A (en) | 1961-02-16 | 1962-02-16 | Vapour phase nitration of cyclohexane |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH397656A (en) |
| DE (1) | DE1230789B (en) |
| FR (1) | FR1316080A (en) |
| GB (1) | GB938644A (en) |
| NL (1) | NL274926A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114685279A (en) * | 2020-12-25 | 2022-07-01 | 南京理工大学 | Preparation method of short-chain nitroalkane |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2206813A (en) * | 1940-07-02 | Pbocess of nitbamng hedbocabbong | ||
| FR1137467A (en) * | 1954-08-05 | 1957-05-29 | Olin Mathieson | Improvements relating to the manufacture of nitrocyclohexane |
| GB824540A (en) * | 1957-04-16 | 1959-12-02 | Du Pont | Improvements in or relating to the preparation of nitro compounds |
-
1962
- 1962-02-08 CH CH154362A patent/CH397656A/en unknown
- 1962-02-12 FR FR887697A patent/FR1316080A/en not_active Expired
- 1962-02-14 DE DEA39461A patent/DE1230789B/en active Pending
- 1962-02-16 NL NL274926D patent/NL274926A/de unknown
- 1962-02-16 GB GB6163/62A patent/GB938644A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114685279A (en) * | 2020-12-25 | 2022-07-01 | 南京理工大学 | Preparation method of short-chain nitroalkane |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1230789B (en) | 1966-12-22 |
| NL274926A (en) | 1964-09-25 |
| FR1316080A (en) | 1963-01-25 |
| CH397656A (en) | 1965-08-31 |
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