GB376356A - Improvements in the isolation or purification of menthols - Google Patents
Improvements in the isolation or purification of mentholsInfo
- Publication number
- GB376356A GB376356A GB1062131A GB1062131A GB376356A GB 376356 A GB376356 A GB 376356A GB 1062131 A GB1062131 A GB 1062131A GB 1062131 A GB1062131 A GB 1062131A GB 376356 A GB376356 A GB 376356A
- Authority
- GB
- United Kingdom
- Prior art keywords
- menthol
- menthols
- neomenthol
- orthophosphoric acid
- isolation
- 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
- 238000002955 isolation Methods 0.000 title abstract 4
- 238000000746 purification Methods 0.000 title abstract 3
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 abstract 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 10
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 abstract 8
- 238000000034 method Methods 0.000 abstract 7
- 239000000203 mixture Substances 0.000 abstract 6
- 235000011007 phosphoric acid Nutrition 0.000 abstract 5
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 abstract 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 abstract 4
- NOOLISFMXDJSKH-LPEHRKFASA-N Isomenthol Natural products CC(C)[C@@H]1CC[C@H](C)C[C@H]1O NOOLISFMXDJSKH-LPEHRKFASA-N 0.000 abstract 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract 3
- 229940041616 menthol Drugs 0.000 abstract 3
- 239000005844 Thymol Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 238000006317 isomerization reaction Methods 0.000 abstract 2
- 150000002729 menthone derivatives Chemical class 0.000 abstract 2
- 229960000790 thymol Drugs 0.000 abstract 2
- YSTPAHQEHQSRJD-UHFFFAOYSA-N 3-Carvomenthenone Chemical compound CC(C)C1CCC(C)=CC1=O YSTPAHQEHQSRJD-UHFFFAOYSA-N 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 abstract 1
- 235000019477 peppermint oil Nutrition 0.000 abstract 1
- 229930006968 piperitone Natural products 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000001256 steam distillation Methods 0.000 abstract 1
- 239000000126 substance Substances 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
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
- C07C35/12—Menthol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Menthol or one of its stereoisomers is separated from mixtures of menthols with one another or with other substances by treating the mixture with orthophosphoric acid and decomposing the resulting addition product, e.g. by heating it alone or with water, into its constituents. In the treatment of mixtures of menthols, a selective isolation of one of the isomers may result from the use of insufficient phosphoric acid to combine with all the menthols present. The addition compound of the menthol may be purified, or the addition compounds with two or more menthol stereoisomers separated, by fractional distillation, recrystallization, fractional steam distillation, or by further treatment with orthophosphoric acid, and the process may be combined with the purification method described in Specification 297,019, [Class 2 (iii), Dyes &c.]. The process is particularly applicable to the crude mixture of isomeric menthols obtained by hydrogenation of thymol, menthones, menthenols and menthenones or by isomerization of these mixtures--see Specifications 213,991 and 238,314, [both in Class 2 (iii), Dyes &c.]. Examples are given of (1) the isolation of racemic menthol from a mixture thereof with racemic isomenthol obtained from the hydrogenation of piperitone; (2) the separation of neomenthol from a mixture containing it, which has been partially purified by the process of Specification 297,019; (3) the isolation of l-menthol from Japanese peppermint oil, and (4) the purification of the racemic menthol product of (1) by the method of Specification 297,019. The Specification also states that the crude hydrogenation or isomerization products of thymol, menthones, &c. may be treated by one of the processes described in Specification 297,019 to remove the neomenthol and the product treated with orthophosphoric acid to remove isomenthol and any residual neomenthol and yield a purified inactive menthol; or the same crude starting material may first be treated with orthophosphoric acid to remove isomenthol and the product freed from neomenthol by one of the processes described in Specification 297,019. Specification 374,893 also is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1062131A GB376356A (en) | 1931-04-10 | 1931-04-10 | Improvements in the isolation or purification of menthols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1062131A GB376356A (en) | 1931-04-10 | 1931-04-10 | Improvements in the isolation or purification of menthols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB376356A true GB376356A (en) | 1932-07-11 |
Family
ID=9971225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1062131A Expired GB376356A (en) | 1931-04-10 | 1931-04-10 | Improvements in the isolation or purification of menthols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB376356A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3014080A (en) * | 1955-04-04 | 1961-12-19 | Glidden Co | Preparation of menthenyl and menthanyl compounds |
| US8785698B2 (en) | 2009-02-17 | 2014-07-22 | Nagaoka & Co., Ltd. | Methods and apparatus for production of natural L-menthol |
-
1931
- 1931-04-10 GB GB1062131A patent/GB376356A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3014080A (en) * | 1955-04-04 | 1961-12-19 | Glidden Co | Preparation of menthenyl and menthanyl compounds |
| US8785698B2 (en) | 2009-02-17 | 2014-07-22 | Nagaoka & Co., Ltd. | Methods and apparatus for production of natural L-menthol |
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