GB490044A - Improvements in or relating to the preparation of lactones - Google Patents
Improvements in or relating to the preparation of lactonesInfo
- Publication number
- GB490044A GB490044A GB23937A GB23937A GB490044A GB 490044 A GB490044 A GB 490044A GB 23937 A GB23937 A GB 23937A GB 23937 A GB23937 A GB 23937A GB 490044 A GB490044 A GB 490044A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- oxy
- alcohol
- ester
- lactone
- 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
- 150000002596 lactones Chemical class 0.000 title abstract 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 13
- 235000011187 glycerol Nutrition 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- -1 Cyclic lactones Chemical class 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 238000010908 decantation Methods 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 150000002314 glycerols Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Cyclic lactones are produced by heating in the liquid phase an ester of an oxy-acid with an alkaline catalyst such as an alkali alcoholate, the ester being so chosen that the lactone is the most volatile constituent of the reaction mixture or is carried over by the vapour of the alcohol formed in the reaction. An inert liquid may be added to facilitate the separation of the lactone. The alcohol may be monovalent or polyvalent and is preferably used in excess. When the alcohol vapour carries off the lactone, the condensed products are separated by decantation or extraction and the alcohol is returned to the reaction vessel. In examples: (1) the glycerol monoester of 16-oxy-12-oxahexadecanoic acid, HO-(CH2)4-O.(CH2)10\t -CO.O.CH2.CH(OH.CH2OH made by condensing the sodium salt of the acid in glycerin with 1-chlor-propandiol-2-3 is heated with glycerin containing dissolved sodium at 2 mm. pressure; (2) the glycerol ester of 15-oxypentadecanoic acid made in a similar manner, is treated similarly; (3) the glycerol ester of 14-oxy-13-methyl-tetradecanoic acid is heated with sodium methylate and glycerin, the distillate being diluted with water and extracted with ether; (4) and (5) lactones are prepared similarly from the glycerol esters of 15-oxy-3-methyl-13-oxa-pentadecanoic acid and 15-oxy-12-oxa-hexadecanoic acid respectively. Specifications 440,416 and 448,708 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23937A GB490044A (en) | 1937-01-04 | 1937-01-04 | Improvements in or relating to the preparation of lactones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23937A GB490044A (en) | 1937-01-04 | 1937-01-04 | Improvements in or relating to the preparation of lactones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB490044A true GB490044A (en) | 1938-08-04 |
Family
ID=9700862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23937A Expired GB490044A (en) | 1937-01-04 | 1937-01-04 | Improvements in or relating to the preparation of lactones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB490044A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2936310A (en) * | 1960-05-10 | Process of preparing macrocyclic | ||
| EP1097930A1 (en) * | 1999-11-08 | 2001-05-09 | Kao Corporation | Method for producing macrocyclic lactone |
| US6255276B1 (en) | 1997-10-09 | 2001-07-03 | Givauden Roure (International) S.A. | Odorant compositions containing macrocycles and processes for manufacturing the same |
-
1937
- 1937-01-04 GB GB23937A patent/GB490044A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2936310A (en) * | 1960-05-10 | Process of preparing macrocyclic | ||
| US6255276B1 (en) | 1997-10-09 | 2001-07-03 | Givauden Roure (International) S.A. | Odorant compositions containing macrocycles and processes for manufacturing the same |
| EP1097930A1 (en) * | 1999-11-08 | 2001-05-09 | Kao Corporation | Method for producing macrocyclic lactone |
| US6617304B1 (en) | 1999-11-08 | 2003-09-09 | Kao Corporation | Method for producing macrocyclic lactone |
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