GB1393845A - Process for the production of 1,12-dodecanedioic acid - Google Patents
Process for the production of 1,12-dodecanedioic acidInfo
- Publication number
- GB1393845A GB1393845A GB3141973A GB3141973A GB1393845A GB 1393845 A GB1393845 A GB 1393845A GB 3141973 A GB3141973 A GB 3141973A GB 3141973 A GB3141973 A GB 3141973A GB 1393845 A GB1393845 A GB 1393845A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- cyclohexanone
- coupling reaction
- adduct
- cyclohexanol
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1393845 Production of 1,12-dodecanedioic acid E I DU PONT DE NEMOURS & CO 2 July 1973 [3 July 1972] 31419/73 Heading C2C 1,12-Dodecanedioic acid is obtained by reductively coupling the adduct of cyclohexanone and hydrogen peroxide with a reducing agent at 20‹ to 100‹ C. and separating the desired acid from the oxidized reducing agent and by-products of the coupling reaction; the reductive coupling reaction being effected with an aqueous solution maintained at pH 1 to 6 and containing ferrous iron combined with a chelating agent, the latter containing at least one carboxylic acid group and at least one basic nitrogen-containing group selected from aminoid and heteroaromatic nitrogen, the carboxylic acid and basic nitrogencontaining groups being separated by at least one but no more than two carbon atoms. The oxidized coupling agent may be regenerated by catalytic hydrogenation (e.g. 0-35À2 Kg./cm.<SP>2</SP> gauge pressure H 2 at 25-100‹ C. over a catalyst comprising one or more of Pd, Pt, Rh and Ru) and recycled to the coupling reaction. The cyclohexanone -H 2 O 2 adduct, viz. the peroxyhemiketal of cyclohexanone, is obtained by reaction of H 2 O 2 with cyclohexanone, a cyclohexanone-cyclohexanol mixture or a cyclohexanone-cyclohexanol-cyclohexane mixture or by air oxidation of cyclohexanol. Exemplified chelating agents are nitrolotriacetic acid, α-benzyl and α-isobutyl-nitrilotriacetic acids, iminodiacetic acid, nitrilotripropionic acid, nitrilopropionic-diacetic acid, ethylenediaminetetraacetic acid, N-(2-picolyl)- iminodiacetic acid and picolinic acid. Example (2-9)a describes the preparation and isolation of cyclohexanone -H 2 O 2 adduct and caproic acid is the major by-product of the reductive coupling reaction.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26876972A | 1972-07-03 | 1972-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1393845A true GB1393845A (en) | 1975-05-14 |
Family
ID=23024403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3141973A Expired GB1393845A (en) | 1972-07-03 | 1973-07-02 | Process for the production of 1,12-dodecanedioic acid |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS57294B2 (en) |
| BE (1) | BE801828A (en) |
| CA (1) | CA1000292A (en) |
| DE (1) | DE2333598C2 (en) |
| FR (1) | FR2236832B1 (en) |
| GB (1) | GB1393845A (en) |
| IT (1) | IT998190B (en) |
| NL (1) | NL176775C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610040A (en) * | 2015-01-22 | 2015-05-13 | 郑州大学 | Preparation method of 1, 12-lauryl binary acid |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58137093A (en) * | 1982-02-09 | 1983-08-15 | 植村 厚一 | Alarming method and apparatus |
-
1973
- 1973-06-28 CA CA175,144A patent/CA1000292A/en not_active Expired
- 1973-06-28 JP JP7238573A patent/JPS57294B2/ja not_active Expired
- 1973-07-02 DE DE19732333598 patent/DE2333598C2/en not_active Expired
- 1973-07-02 GB GB3141973A patent/GB1393845A/en not_active Expired
- 1973-07-02 IT IT2610273A patent/IT998190B/en active
- 1973-07-03 BE BE133047A patent/BE801828A/en not_active IP Right Cessation
- 1973-07-03 FR FR7324468A patent/FR2236832B1/fr not_active Expired
- 1973-07-03 NL NL7309271A patent/NL176775C/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610040A (en) * | 2015-01-22 | 2015-05-13 | 郑州大学 | Preparation method of 1, 12-lauryl binary acid |
| CN104610040B (en) * | 2015-01-22 | 2016-04-27 | 郑州大学 | One prepares the method for 1,12-dodecanedioic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1000292A (en) | 1976-11-23 |
| JPS4942607A (en) | 1974-04-22 |
| DE2333598C2 (en) | 1985-07-18 |
| NL176775C (en) | 1985-06-03 |
| NL176775B (en) | 1985-01-02 |
| IT998190B (en) | 1976-01-20 |
| FR2236832A1 (en) | 1975-02-07 |
| BE801828A (en) | 1974-01-03 |
| FR2236832B1 (en) | 1977-05-13 |
| JPS57294B2 (en) | 1982-01-06 |
| DE2333598A1 (en) | 1974-01-24 |
| NL7309271A (en) | 1974-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |