GB1061700A - The preparation of ?-caprolactone - Google Patents
The preparation of ?-caprolactoneInfo
- Publication number
- GB1061700A GB1061700A GB445766A GB445766A GB1061700A GB 1061700 A GB1061700 A GB 1061700A GB 445766 A GB445766 A GB 445766A GB 445766 A GB445766 A GB 445766A GB 1061700 A GB1061700 A GB 1061700A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iron
- reaction mixture
- caprolactone
- ferric
- hydrocarbon
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 abstract 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 4
- 150000002505 iron Chemical class 0.000 abstract 4
- 239000011541 reaction mixture Substances 0.000 abstract 4
- 239000005711 Benzoic acid Substances 0.000 abstract 3
- 235000010233 benzoic acid Nutrition 0.000 abstract 3
- ITAUHKJMPRCVIH-UHFFFAOYSA-K iron(3+);tribenzoate Chemical compound [Fe+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 ITAUHKJMPRCVIH-UHFFFAOYSA-K 0.000 abstract 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 2
- 229910001882 dioxygen Inorganic materials 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 150000002506 iron compounds Chemical class 0.000 abstract 2
- 159000000014 iron salts Chemical class 0.000 abstract 2
- HOIQWTMREPWSJY-GNOQXXQHSA-K iron(3+);(z)-octadec-9-enoate Chemical compound [Fe+3].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O HOIQWTMREPWSJY-GNOQXXQHSA-K 0.000 abstract 2
- 239000007791 liquid phase Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000005609 naphthenate group Chemical group 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
- C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen
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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
Abstract
e -Caprolactone is prepared by oxidizing cyclohexanone in the liquid phase by means of a gas containing molecular oxygen in the presence of benzaldehyde and an iron salt catalyst dissolved in the reaction mixture. The iron salt may be ferric benzoate produced by introducing into the reaction mixture an iron compound capable of reacting with benzoic acid therein to produce ferric benzoate, e.g. iron oxide. Other useful iron salts are ferric oleate, naphthenate and acetate. The temperature should be kept below 100 DEG C., preferably between 20 DEG and 50 DEG C. A solvent may be used, e.g. a hydrocarbon, chlorinated hydrocarbon or an ester. Benzoic acid and adipic acid are also produced in the process.ALSO:Polymerized caprolactone is prepared in a process for making e -caprolactone (see Division C2) which comprises oxidizing cyclohexanone in the liquid phase by means of a gas containing molecular oxygen, in the presence of benzaldehyde and an iron salt catalyst dissolved in the reaction mixture. The iron salt may be ferric benzoate produced by introducing into the reaction mixture an iron compound capable of reacting with benzoic acid, e.g. iron oxide. Other useful iron salts are ferric oleate, naphthenate and acetate. The temperature should be kept below 100 DEG C., preferably between 20 DEG and 50 DEG C. A solvent may be used, e.g. a hydrocarbon, chlorinated hydrocarbon or an ester.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6501333A NL6501333A (en) | 1965-02-03 | 1965-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1061700A true GB1061700A (en) | 1967-03-15 |
Family
ID=19792262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB445766A Expired GB1061700A (en) | 1965-02-03 | 1966-02-01 | The preparation of ?-caprolactone |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT260890B (en) |
| BE (1) | BE675887A (en) |
| CH (1) | CH462795A (en) |
| DE (1) | DE1593529A1 (en) |
| ES (1) | ES322528A1 (en) |
| GB (1) | GB1061700A (en) |
| IL (1) | IL25069A (en) |
| NL (1) | NL6501333A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0548774A1 (en) * | 1991-12-25 | 1993-06-30 | Sumitomo Chemical Company, Limited | Process for producing a lactone or an ester |
| RU2326861C1 (en) * | 2007-01-10 | 2008-06-20 | Курский государственный технический университет (КГТУ) | Method of obtaining iron benzoate (iii) |
| RU2398758C1 (en) * | 2008-12-22 | 2010-09-10 | Государственное образовательное учреждение высшего профессионального образования Курский государственный технический университет (КурскГТУ) | Lead (ii) acetate synthesis method |
| RU2412153C2 (en) * | 2007-02-13 | 2011-02-20 | Государственное образовательное учреждение высшего профессионального образования "Юго-Западный государственный университет" | Method of producing iron (iii) benzoate |
-
1965
- 1965-02-03 NL NL6501333A patent/NL6501333A/xx unknown
-
1966
- 1966-01-30 IL IL2506966A patent/IL25069A/en unknown
- 1966-02-01 AT AT89266A patent/AT260890B/en active
- 1966-02-01 BE BE675887D patent/BE675887A/xx unknown
- 1966-02-01 CH CH135266A patent/CH462795A/en unknown
- 1966-02-01 GB GB445766A patent/GB1061700A/en not_active Expired
- 1966-02-02 ES ES0322528A patent/ES322528A1/en not_active Expired
- 1966-02-02 DE DE19661593529 patent/DE1593529A1/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0548774A1 (en) * | 1991-12-25 | 1993-06-30 | Sumitomo Chemical Company, Limited | Process for producing a lactone or an ester |
| US5405974A (en) * | 1991-12-25 | 1995-04-11 | Sumitomo Chemical Company, Limited | Process for producing a lactone or an ester |
| RU2326861C1 (en) * | 2007-01-10 | 2008-06-20 | Курский государственный технический университет (КГТУ) | Method of obtaining iron benzoate (iii) |
| RU2412153C2 (en) * | 2007-02-13 | 2011-02-20 | Государственное образовательное учреждение высшего профессионального образования "Юго-Западный государственный университет" | Method of producing iron (iii) benzoate |
| RU2398758C1 (en) * | 2008-12-22 | 2010-09-10 | Государственное образовательное учреждение высшего профессионального образования Курский государственный технический университет (КурскГТУ) | Lead (ii) acetate synthesis method |
Also Published As
| Publication number | Publication date |
|---|---|
| ES322528A1 (en) | 1966-11-16 |
| CH462795A (en) | 1968-09-30 |
| NL6501333A (en) | 1966-08-04 |
| IL25069A (en) | 1969-05-28 |
| DE1593529A1 (en) | 1970-10-22 |
| AT260890B (en) | 1968-03-25 |
| BE675887A (en) | 1966-08-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1061700A (en) | The preparation of ?-caprolactone | |
| GB1313083A (en) | Process for producing para-toliuc acid and monomethyl terephthalate | |
| GB1156573A (en) | Method of making diacyl peroxides | |
| GB1368309A (en) | Process for producing a pyridine carboxylic acid | |
| ES8104178A1 (en) | PROCEDURE TO PREPARE AROMATIC CARBOXYL ACIDS BY OXIDATION OF AN ALCOHYL-AROMATIC HYDROCARBON | |
| US3176039A (en) | Process of preparing carboxylic esters | |
| ES463559A1 (en) | TEREFTALIC ACID PREPARATION PROCEDURE. | |
| GB1445116A (en) | Process for the preparation of aromatic carboxylic acids | |
| ES348640A1 (en) | Preparation of aromatic disubstituted carboxylic acids | |
| GB1291968A (en) | Process for the production of manganic carboxylates | |
| GB907926A (en) | Improvements in or relating to the production of trimellitic acid and trimellitic anhydride | |
| GB1482064A (en) | Method for producing cyclohexanone and p-cresol or phenol | |
| GB744721A (en) | Process for the manufacture of salts or other derivatives of aromatic dicarboxylic acids, especially of terephthalic acid | |
| GB1388679A (en) | Preparation of benzoquinones | |
| ES350886A1 (en) | Preparation of epsilon-caprolactone | |
| GB1030847A (en) | Process for the preparation of aromatic carboxylic acids | |
| GB1155589A (en) | Improved process for the production of Terephthalic Acid | |
| GB1493644A (en) | Process for producing aromatic polycarboxylic acids | |
| GB892631A (en) | Process for the preparation of aliphatic peracids | |
| GB978870A (en) | Liquid phase oxidation of xylenes | |
| ES361739A1 (en) | Production of phthalic acids | |
| GB894735A (en) | A process for the production of cyclohexanol and cyclohexanone | |
| GB1384110A (en) | Preparation of 2,6-naphthalene dicarboxylic acid | |
| GB1012237A (en) | A process for the preparation of carboxylic acids | |
| GB866042A (en) | Process for the preparation of aromatic phosphinic acids |