MXPA96005220A - Recovery of evil - Google Patents
Recovery of evilInfo
- Publication number
- MXPA96005220A MXPA96005220A MXPA/A/1996/005220A MX9605220A MXPA96005220A MX PA96005220 A MXPA96005220 A MX PA96005220A MX 9605220 A MX9605220 A MX 9605220A MX PA96005220 A MXPA96005220 A MX PA96005220A
- Authority
- MX
- Mexico
- Prior art keywords
- maltol
- solvent
- mixture
- aqueous layer
- weight
- Prior art date
Links
- 238000011084 recovery Methods 0.000 title claims description 12
- XPCTZQVDEJYUGT-UHFFFAOYSA-N Maltol Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 claims abstract description 64
- 229940043353 maltol Drugs 0.000 claims abstract description 64
- 239000002904 solvent Substances 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 35
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 27
- 239000011347 resin Substances 0.000 claims description 21
- 229920005989 resin Polymers 0.000 claims description 21
- 239000008079 hexane Substances 0.000 claims description 14
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 13
- 241000218657 Picea Species 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000008601 oleoresin Substances 0.000 claims description 11
- 238000000638 solvent extraction Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 7
- 229930006725 alpha-pinene Natural products 0.000 claims description 4
- 241000894007 species Species 0.000 claims description 3
- 125000003447 alpha-pinene group Chemical group 0.000 claims description 2
- 238000000605 extraction Methods 0.000 abstract description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 241000218631 Coniferophyta Species 0.000 description 4
- 235000011613 Pinus brutia Nutrition 0.000 description 4
- 230000000295 complement Effects 0.000 description 4
- 235000005590 Larix decidua Nutrition 0.000 description 3
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 3
- 241000018646 Pinus brutia Species 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000218652 Larix Species 0.000 description 2
- 102100012174 PIWIL2 Human genes 0.000 description 2
- 101710043199 PIWIL2 Proteins 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 240000002254 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 1
- 241001235216 Larix decidua Species 0.000 description 1
- 240000007182 Ochroma pyramidale Species 0.000 description 1
- 241000218641 Pinaceae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010192 crystallographic characterization Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940093503 ethyl maltol Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- -1 heterocyclic aromatic chemical compound Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Abstract
The present invention relates to pure maltol from a mixture containing maltol by extraction in an aqueous solution, optionally in the presence of a solvent substantially insoluble in water, in which the maltol of the mixture is substantially insoluble.
Description
RECOVERY OF MOLTOL
MEIIORIO DESCRIPTIVR
The present invention is directed to a process for obtaining maltol and more particularly to a process for obtaining pure maltol. Maltol (3-hydroxy-2-methyl-4H-? Iran-4-one) is a heterocyclic aromatic chemical compound broadly used in flavors, fragrances and in some pharmaceutical compositions. Maltol is found naturally in many plant species and its isolation from these sources has been widely described in the literature. In particular, it has been described since the beginning of the century its isolation from conifer trees such as larches (Larix decidua mili), pine and pine needles (ñbis alba mili, pinaceae). U.S. Patent No. 5,221,756 issued June 22, 1993, relates to a process for the recovery of rnaltol from a mixture of rnaltol by a joint distillation with an aliphatic or cycloaltyl hydrocarbon in which the maltol it is substantially insoluble; and then the condensation of the whole distillate to recover substantially pure maltol crystals. Rnal + ol has been obtained from a destructive distillation of wood but such procedures only produce a small amount of inal + ol. This procedure is not economically desirable. Fleisher S Fleisher, "Uater-soluble Fractions of * he
Essential Oils ", Perfumer and Flavorist, Vol 16 (May / June, pages 37-41, 1991) refer to the recovery and characterization of compounds from spruce needles (ñbis balsa ea L.) Patents of the States No. 3,031,204, 4,082,717 and 4,343,697 relate to processes for the synthesis of gamma piñas, such as maltol, ethyl maltol and piromeconic acid The present invention is directed to a process for the recovery of maltol which comprises: a) heating a mixture containing maltol in the presence of a substantial solvent immiscible in water in which the rnaltol is substantially insoluble in said mixture to form an aqueous layer and a layer of solvent; and b) the recovery of said aqueous layer The process in which the maltol is recovered from the aqueous layer is further preferred, the process wherein said solvent is selected from the group consisting of hexane, a-pmeno is preferred. and petroleum ester; and its combinations. Also preferred is the process wherein said solvent is hexane.
Also preferred is the process wherein said solvent is α-pinene. Also preferred is the process wherein said solvent is petroleum ether. The process in which said mixture is a resin is especially preferred. Also preferred is the process in which said resin is obtained from a solvent extraction of a conifer strain, with the needles being a preferred conifer, with the needles being derived from the flbis balsamea spruce being particularly preferred. Also preferred is the process in which the solubility of the maltol in said solvent is less than about 0.3% by weight at room temperature. The present invention is also directed to the substantially pure maltol produced by the process of the present invention. In a further embodiment, the present invention is directed to a process for the recovery of maltol comprising a) heating an oleorhrein containing maltol in the presence of an aqueous solution to form an aqueous layer and a layer of resin; b) the recovery of said aqueous layer. Additionally, the process in which the maltol is recovered from the aqueous layer is preferred.
The procedure in »? that the oleoresin is obtained from the solvent extraction of coniferous species, with the needles being an especially preferred source of conifers, with particularly preferred needles being those obtained from the fíb ß balsamea firs. Also preferred is the process in which the aqueous solution is added in a weight ranging from about 0, 5 and approximately 5 times the weight of the oleoresin. The present invention is directed to a process for the recovery of pure maltol from a mixture containing maltol. The mixture can be any mixture obtained from, for example, plant species or coniferous trees known to contain maltol. Preferably, the mixture is
• a resin obtained from solvent extraction of pine needles, or larch bark, both sources abundant in natural maltol. Preferably, the mixture is obtained from the extraction of the needles obtained from the spruce (ñh s bal amea
L.). The crude resin obtained from, for example, spruces, usually contains 3 to 8% of inaltol. If, for example, a spruce resin is used, the common distillation process referred to in U.S. Patent No. 5,221,756 requires large quantities of hydrocarbon solvent, both in step do? common ilation as in condensation. In the present invention, it has been found that the resin can be heated, for example, in the presence of a solvent in which the maltol is substantially insupportable. The temperature of the heating stage can range from about 35 ° C to about 100 ° C. Preferably, the solubility of the maltol in the solvent is less than about 0.3% by weight at ambient temperature. Suitable solvents are any solvent in which the maltol is substantially insoluble. The preferred solvents are organic solvents such as hexane, a-pinene and petroleum ether. Especially preferred solvents are hexane and a-pinene. The amount of solvent used may vary depending on the material from which the maltol has been extracted. If, for example, maltol is extracted from a spruce needle resin, the weight of solvent will be approximately equal to the weight of the resin. In the process of the present invention, an aqueous solution is added to the above-mentioned product mixture of solvent / maltol. The term aqueous solution includes water, in addition to any other solution containing substantial amounts of water. The amount of aqueous solution used may also vary depending on the material from which the rnaltol is being extracted. If, for example, the inaltol is being extracted from a spire needle resin, the weight of aqueous solution could be approximately equal to the weight of the composition of the solvent / rnaltol mixture formed above. The heating of this product produces a composition with two liquid phases in which the aqueous phase contains maltol. If desired, maltol can be extracted in a series of stages by extraction of the aqueous layer followed by the addition of an aqueous solution to the remaining resin, by
..- jernplo, to create another aqueous layer from which the maltol can be recovered. Further, if the initial mixture of maltol is an oleoresin obtained from, for example, solvent extraction of spruce needles, the maltol can be extracted by heating, for example, to about 80 ° C of the oleoresin in the presence of of an aqueous solution. Having described the invention in general terms,
> and now refers to the specific examples. It will be understood that these examples are not intended to limit the present invention, the scope of which is determined by the appended claims.
EXAMPLE 1 Extraction of Maltol in the Presence of Hexane as a Complementary Solvent Balsamic spruce oleoresin obtained from the solvent extraction of flubis-needles L. with an equal weight of hexane was mixed and the mixture was heated with agitation until uniform. A weight of water equal to the weight of the resin-hexane mixture was added and the mixture was vigorously stirred at the reflux temperature of hexane (69 ° C) for 45 minutes. The mixture was transferred to a separatory funnel equipped with a condenser and a steam jacket, heated again to the reflux temperature of the hexane and allowed to separate. The aqueous layer was collected, weighed and tested for maltol. A second weight of water equal to the initial weight was added to the hexane-resin mixture and the extraction procedure was repeated.
1-Extraction 2 Extraction
Weight of the aqueous layer, 193 194 masters Concentration of maltol 1.46 0.59 in the aqueous layer, percentage Percentage of rnalrol 57.2 23.3 extracted in the aqueous layer The combined yield of rnaltol for the two extractions was 80.5%.
EXAMPLE 2 Extraction of Maltol in the Presence of α-Pinene as Complementary Solvent Balsamic spruce oleoresin obtained from the solvent extraction of ñbis balsamea L. needles was mixed with an equal weight of α-pinene and the mixture was heated with stirring until uniformity. A weight of water equal to the weight of the resin-pinene mixture was added and the mixture was stirred vigorously at 70-80 ° C for 45 minutes. The mixture was transferred to a separatory funnel equipped with a condenser and a steam jacket, heated again and allowed to separate. The aqueous layer was collected, weighed and tested for maltol. A second weight of water equal to the initial weight was added to the pinene-resin mixture and the extraction procedure was repeated.
lExtraction 2SExtraction
Weight of the aqueous layer, 155 187 grams Concentration of maltol 1.56 0.75 in the aqueous layer, percentage Percentage of inaltol 49.8 28.9 extracted in the aqueous layer The combined yield of rnaltoi for the two extractions was 78-7%.
EXAMPLE 3 Degree of Phase Separation for Various Solvents Balsamic spruce oleoresin obtained from the solvent extraction of fíbis fralsamea L. needles was mixed with an equal weight of solvent and heated and stirred to form a uniform mixture. A weight of water equal to the weight of the resin-solvent mixture was added and the mixture was vigorously stirred with heating, then allowed to separate. The following observations were made about the degree of separation:
Solvent Separation
Hexane Good Toluene Bad Oil Ether Good a-pinene Good
Example 4 Solubility of Maltol in Various Solvents The solubility of maltol at room temperature was determined in the solvents of Example 3, by filtration of saturated solutions and testing of the filtrates.
Solvent Maltol concentration, percentage
Hexane 0.043 Toluene 0.46 Petroleum Ether 0.05 a-pinene 0.12
Example 5: Distribution of Maltol in the Water-Solvent Systems Vigorous mixtures of one part solvent, one part resin and two parts water were vigorously stirred for 5 minutes at about 40 ° C, then allowed to separate. The aqueous layers were tested for maltol.
Solvent Concentration of Maltol in the cough layer, percentage
Hexane 1.62 Toluene 1.15 Petroleum Ether 1.24 a-pinene 1.60 Based on these data, hexane and a-pinene are the preferred solvents for the extraction of rnaltol in an aqueous solution.
EXAMPLE 6 Maltol Aqueous Extraction Without Complementary Solvent Balsamic fir oleoresin obtained from the solvent extraction of Pbis alsamea L. needles was mixed with an equal weight of water and the mixture was heated at B0 ° C with stirring during a hour. Agitation was discontinued and the mixture was maintained at 80 ° C for 45 minutes to allow phase separation. The mixture was cooled to 55 ° C and the aqueous and resin layers were isolated. The following data was obtained:
Weight of the aqueous layer 90.0 gr. ^ that of the resin layer 99.3 gr. Concentration of maltol in the aqueous layer 2.2% Concentration of maltol in the resin layer 2.68% Portion of maltol extracted in the aqueous layer 42.8% Portion of maltol extracted in the resin layer 57.2% Example 7 Aqueous Extraction of Maltol Without Complementary Solvent mixed balsamic spruce oleoresin obtained from the solvent extraction of flhis balsame L. needles with 1.5 times their weight of water and the mixture was heated at 80-85 ° C with stirring for one hour. Agitation was discontinued and the mixture was maintained at 80 ~ 85 ° C for 45 minutes to allow phase separation. The brine layer was isolated, weighed and tested for maltol.
Weight of the aqueous layer 127.5 gr. Concentration of maltol in the aqueous layer 1.84% Portion of maltol extracted in the aqueous layer 59.5% Having described the invention as above, the content in the following is declared as property.
Claims (17)
1. A process for the recovery of maltol comprising: a) heating a mixture containing maltol with an aqueous solution and a solvent substantially immiscible with water, in which the maltol is substantially soluble in said mixture, to form a aqueous layer containing maltol and a layer of solvent; and b) recovering said aqueous layer.
2. The process of claim 1 further comprising the step of recovering the maltol from the aqueous layer.
3. The process of claim 1, wherein said solvent is selected from the group consisting of .exane, a-pinene and petroleum ether; and its combinations.
4. The process of claim 3, wherein said solvent is hexane.
5. The process of claim 3, wherein said solvent is α-pinene.
6. The process of claim 3, wherein said solvent is petroleum ether.
7. The method of claim 1, wherein said mixture is a resin.
8. The method of claim 7, wherein said resin is obtained from the solvent extraction of needles of coniferous species.
9. The method of claim 8, wherein said needles are from Abis balsamea L.
10. The method of claim 1, wherein the solubility of maltol in said solvent is less than about 0.3% in weight at room temperature.
11. The substantially pure maltol produced by the process of the claim.
12. A process for the recovery of rnaltol comprising a) heating an oleoresin containing maltol in the presence of an aqueous solution to form an aqueous layer and a resin layer; b) the recovery of said aqueous layer.
13. The process of claim 12 further comprising the step of recovering maltol from the aqueous layer.
14. The process of claim 12, wherein the oleoresin is obtained from solvent extraction of needles of coniferous species.
15. The method of claim 14, wherein said needles are spruce ñbis balsamea L.
16. The method of claim 12, wherein the aqueous solution is added in a weight ranging from about 0.5 to about 5 times the weight of oil re m.
17. - The substantially pure maltol produced by the process of claim 12.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23672394A | 1994-04-29 | 1994-04-29 | |
| US236,723 | 1994-04-29 | ||
| US236723 | 1994-04-29 | ||
| PCT/IB1995/000224 WO1995029908A1 (en) | 1994-04-29 | 1995-04-03 | Maltol recovery |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX9605220A MX9605220A (en) | 1997-09-30 |
| MXPA96005220A true MXPA96005220A (en) | 1998-07-03 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Bento et al. | Humic extracts of hydrochar and Amazonian Dark Earth: molecular characteristics and effects on maize seed germination | |
| EP1948715B1 (en) | Extraction and fractionation of biopolymers and resins from plant materials | |
| JP4386972B2 (en) | Process for producing essential oil by supercritical water treatment and essential oil obtained by supercritical water treatment | |
| US4552666A (en) | Process for the treatment of sewage sludge | |
| US4549990A (en) | Manufacture of non-saponifiable compounds from natural substances and the resulting products | |
| EP2310379B1 (en) | Method for the fractionation of knotwood extract and use of a liquid-liquid extraction for purification of knotwood extract | |
| SK279652B6 (en) | Pharmaceutically active composition from tanacetum parthenium, process of its preparation, and pharmaceutical composition containing thereof | |
| EP0026559A1 (en) | Liquid carbon dioxide extraction of pyrethrins and a purified pyrethrin composition | |
| McLean et al. | The constituents of Nauclea diderrichii. Part II. isolation and classification of constituents; simple β-carboline and pyridine alkaloids | |
| AU680742B2 (en) | Maltol recovery | |
| CA1211123A (en) | Process for removing lecithin | |
| MXPA96005220A (en) | Recovery of evil | |
| EP1171212A2 (en) | Solvent extraction process | |
| EP0058365A1 (en) | Process of obtaining components of camomile by extraction with carbon dioxide | |
| Ozek et al. | Supercritical CO2 extraction of volatile components from leaves of Laurus nobilis L | |
| JP4462789B2 (en) | Heavy metal adsorbent and method for producing the same | |
| US4666498A (en) | Process and apparatus for obtaining raw materials from autumn foliage | |
| AU2001285374B2 (en) | Method of providing an essential oil extract of capsicum, and the extract | |
| CN112358913B (en) | Method and device for processing liquidambar by liquid precipitation separation of liquefied gas | |
| Povh et al. | Extraction of essential oil and oleoresin from chamomile (Chamomila recutita [L.] Rauschert) by steam distillation and extraction with organic solvents: a process design approach | |
| RU2322501C1 (en) | Method for complex processing balsamic poplar vegetative part | |
| US7318940B2 (en) | Method for isolation of silymarin from Sylibum marianum seeds | |
| US2347460A (en) | Process for treating fat-soluble vitamin-containing oils | |
| Menut et al. | Aromatic plants of tropical central Africa. Part XVII. 6, 7‐epoxymyrcene, the major unusual constituent of Lippia multiflora sl moldenke essential oil from the central African Republic | |
| WO2006090953A1 (en) | Extraction method for antioxidants from pine trees using natural solvents and antioxidant extracts thereby |