CN101134719A - Method for preparing tetrahydrochysene isohumulone by hop concrete or lupulone oil - Google Patents
Method for preparing tetrahydrochysene isohumulone by hop concrete or lupulone oil Download PDFInfo
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- CN101134719A CN101134719A CNA2006101123790A CN200610112379A CN101134719A CN 101134719 A CN101134719 A CN 101134719A CN A2006101123790 A CNA2006101123790 A CN A2006101123790A CN 200610112379 A CN200610112379 A CN 200610112379A CN 101134719 A CN101134719 A CN 101134719A
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- humulone
- lupulone
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Abstract
The present invention relates to process of preparing tetrahydro isohumulon from hop extractum or lupulone oil. The process includes separating lupulone from hop extractum or lupulone oil, hydrogenating lupulone to obtain tetrahydro humulon, and final fast oxidation and isomerization with air or pure oxygen in alkaline alcohol solution in the presence of palladium-containing carbon powder or active carbon as catalyst to obtain tetrahydro isohumulon. The process with catalyst action has high speed and high yield. The product is applied in beer or other food, and has enhanced foaming function, bacteriostasis function, light resistance and bitter taste over one time higher than that of isohumulon.
Description
Technical field
The present invention relates to the brewage field, more specifically, the present invention relates to a kind of method for preparing tetrahydro-iso-humulone from hop extract or lupulone oil.
Background technology
Hops or Hops Extract in the process of beer brewing (being called for short hops or hop extract) are added in the Wort boiling pot, humulone composition in hops or the hop extract (claiming α acid again), be isomerizated into isohumulone (claiming isomery humulone or isohumulone again) through chemical reaction and dissolve in the wheat juice, wheat juice is promptly becoming beer through behind the yeast fermentation.Isohumulone can be given beer with distinctive bitter taste, suppresses the growth of spoilage microorganisms, strengthens the foam characteristic of beer.Another main component of hops or hop extract is that lupulone (claiming β acid again) is insoluble in the wheat juice, can be deposited in usually wheat poor in and abandon it.So lupulone does not almost have economic worth in brewage.
Because humulone or isohumulone are to the auroral poles instability in the beer, be easy to wine in the sulfide react with, the general beer of brewageing with hops or hop extract is if be packaged in green or the clear vial, when being exposed under daylight or the light, can produce a kind of foreign odor flavor (being the smelly or skunk flavor of daylight) that is unfavorable for beer flavor and freshness.For addressing this problem, in recent years after deliberation and technique improvement, invented that a kind of it is stable and still have the hop product of the various functions of isohumulone to auroral poles, this product is the derivative of humulone processing, being called tetrahydro-iso-humulone, also is the product that U.S. food management board is firmly believed.In beer or other many beverage/foods, be particularly suitable for brewageing the beverage/food product of clear-glass bottle or Green Glass Green glass bottles and jars only packing, tetrahydro-iso-humulone is except having very strong light resistance, also has further feature, as strengthening lathering property, anti-microbial property, its stability is stronger than isohumulone.Especially the bitter taste of tetrahydro-iso-humulone is the twice of isohumulone, can save the use of hops or hops greatly.
In the world brewing industry the widespread use tetrahydro-iso-humulone in brewage as the bitter taste additive after the fermentation to regulate the beer acerbity value, strengthen holding property of beer bubble, increase ability that beer suppresses spoilage organism, to improve light resistance and increase beer stability.Beer acerbity with this products production is preferable, beer quality stable, and economical and practical (except two times of bitter tastes, its utilization ratio in beer is higher than 60%).
Tetrahydro-iso-humulone removes and can also can prepare from lupulone directly from the humulone manufacturing, makes the method for tetrahydro-iso-humulone from humulone and has made know document and the domestic and international patent document.Lupulone is one of main component in hops or the hop extract, but is waste material basically in the brewage process, does not have how many use, if can be apt to add utilization, then can improve the utilization ratio and the added value of hops or beer medicinal extract.In document and patent, announced and put down in writing basic theories and several preparation methods.Such as U.S. Patent number 3,552,975 (1971) disclose a kind of method is hydrogenated to tetrahydrochysene anaerobic humulone with the lupulone hydrogenation and can proposes the tetrahydrochysene humulone through the air or oxygen oxidation in plumbic acid solution again, promptly changes into tetrahydro-iso-humulone through isomerization again.The shortcoming of this method is a lot of when being the oxidation construction cost, and might be in product residual deleterious lead compound.U.S. Patent number 3,923,897 (1975) disclose the another kind of method for preparing tetrahydro-iso-humulone, this method be in organic solvent with various peroxide oxidation tetrahydrochysene anaerobic humulone become behind the tetrahydrochysene humulone re-isomerization tetrahydro-iso-humulone.The shortcoming of this method is might residue in the product kind with superoxide and organic solvent food and environment are harmful to.U.S. Patent number 4,644 in 1987, and 084 discloses a kind ofly to food and the environment preparation method of safety, only uses safe crude substance such as air, ethanol, water and alkali and acid.This method is to separate humulone and two kinds of compositions of isohumulone from the hop extract of carbon dioxide abstraction earlier, and it is recorded and narrated in detail in U.S. Patent number 4,590,296 (1986) and 4,666,731 (1987).Lupulone hydrogenation in alcoholic solution then filters out palladium carbon dust catalyzer and adds alkaline aqueous solution and/or organic alkali salt, and logical oxygen or atmospheric oxygen change into the tetrahydrochysene humulone, also heating is isomerizated into tetrahydro-iso-humulone simultaneously.China Patent No. 94100149.0 disclosed a kind of humulone and lupulone mixture in the hop extract that do not need to separate earlier in 1997, directly humulone and lupulone was changed into tetrahydro-iso-humulone simultaneously.In the method, after the hydrogenation, evaporate alcoholic solution, other adds ethane or methylene dichloride and the palladium carbon dust that stays and air or oxygen and be oxidized to the tetrahydrochysene humulone in organic solvent, adds the alkaline aqueous solution re-isomerization then and becomes tetrahydro-iso-humulone.This method is not only with unsafe organic solvent and be that two-step approach is separately carried out in oxidation and isomerization.Above-mentioned all methods all are that palladium carbon dust that U.S. food management board is permitted is as the hydrogenant catalyzer.
Summary of the invention
The present invention proposes in order to solve above-mentioned problems of the prior art, and be different from the above-mentioned United States Patent (USP) 4 that does not add catalyzer, 644,084 method, the two-step approach that also is different from Chinese patent 94100149.0, but adopted the single stage method of catalyzer, therefore method of the present invention has the following advantages:
Substantially be to prepare tetrahydrochysene anaerobic humulone in the lupulone of waste material from the brewage process, improved the utilization ratio and the added value of hops or beer medicinal extract.
After using palladium carbon dust hydrogenated lupulone in the method for the present invention, tetrahydrochysene anaerobic humulone in the alcoholic solution of the reaction product of filtered also easily is oxidized to the tetrahydrochysene humulone under the situation of no air insulated, confirm through test, under alkaline condition, contain the efficient that the palladium carbon dust helps to improve oxidation.
Palladium carbon dust among the present invention is the dual catalytic agent, needn't filter out after the hydrogenation, add alkali in alcohol mixture, continue performance oxidation catalysis function and under alkaline condition, be oxidized to tetrahydrochysene anaerobic humulone simultaneously synchronously to become the tetrahydrochysene humulone and be isomerizated into tetrahydro-iso-humulone immediately by the palladium carbon dust.The present invention not only uses the ethanol for food safety, confirms that also oxidizing reaction is feasible in the neutralized alcohol solution.In the alkaline condition alcoholic solution by catalyzer not only oxidizing reaction fast and can carry out isomerization reaction simultaneously, it is easy to save time, and need not exchange solvent.The present invention not only output improves, and has more advantage on productive value and the cost.
Method of the present invention may further comprise the steps:
(1) step of separation lupulone from hop extract or lupulone oil;
(2) be the step of tetrahydrochysene anaerobic humulone with lupulone hydrogenation under the effect of catalyzer;
And directly the tetrahydrochysene anaerobic humulone oxidation that contains catalyzer in the step (2) is isomerizated into step (3) but filtration catalizer, into tetrahydro-iso-humulone.
Wherein step (1) is undertaken by following flow process:
Hop extract and alkaline aqueous solution are stirred under 25～100 ℃, regulate pH between 8～9.5, the lower floor's water that obtains is the humulone aqueous solution, and upper oil phase is a lupulone oil;
Lupulone oil and the alkaline aqueous solution that obtains stirred under 25～100 ℃ again, regulate pH between 9.5～12, the lower floor's water that obtains is the lupulone aqueous solution, and upper oil phase is a hop essential oil;
With after the humulone aqueous solution and the acidifying of lupulone aqueous solution difference, upper oil phase is respectively humulone and lupulone again.
Wherein used alkaline aqueous solution is one or more the aqueous solution that is selected from the following compound: KOH, NaOH, K
2CO
3, Na
2CO
3, Ca (OH)
2And Mg (OH)
2Wherein employed acid is selected from one or more in phosphoric acid, hydrochloric acid, sulfuric acid, nitric acid and the carbonic acid.
The process of step (2) is as follows:
Lupulone is dissolved in one or more blended alcoholic solvents that are selected from methyl alcohol, ethanol and propyl alcohol, in prepared alcoholic solution, add 0.1～5% aforesaid acid based on whole alcoholic solution weight, under hydrogen and catalyst action, carry out hydrogenation, temperature of reaction is 20～80 ℃, reaction times is 1～4 hour, hydrogen pressure is 0～2MPa, obtains the alcoholic solution of tetrahydrochysene anaerobic lupulone.Described catalyzer is palladium carbon dust catalyzer or activated carbon; Wherein metallic palladium content is 0～20% of total catalyst weight, and catalyst consumption is 0.1～20% of the middle lupulone weight of step (2).
The flow process of step (3) is as follows:
After the hydrogenation through step (2), the material that the alcoholic solution that does not filter out the reaction product tetrahydrochysene anaerobic humulone of catalyzer adds alkaline aqueous solution and is selected from one of group of comprising alkaline earth salt, alkaline earth metal oxide or both mixtures direct Hybrid Heating under air or oxygen, thereby make the humulone oxidation of tetrahydrochysene anaerobic and be isomerizated into tetrahydro-iso-humulone, acidifying filters out catalyzer, evaporates alcoholic solvent and promptly obtains tetrahydro-iso-humulone.
Wherein said alkaline earth salt or its oxide compound are selected from and comprise CaCO
3, MgCO
3, CaO, CaCl
2, CaSO
4, MgO, MgCl
2And MgSO
4In one or more.Above in 3 steps used acid be the conventional acid of using in this area.
Embodiment
Following examples only are to be used to illustrate method of the present invention, and do not limit the present invention.
Embodiment 1
With the tetrahydrochysene anaerobic humulone after the lupulone hydrogenation is the raw material of present embodiment, in room temperature and following table, test under four kinds of different conditions, wherein at first the 0.20 tetrahydrochysene anaerobic humulone that restrains is dissolved in 10 milliliters of ethanol, difference 1) condition in is for to carry out in neutral alcoholic solution (pH approximates 7), do not add alkaline aqueous solution and regulate the pH value, do not add catalyzer yet; 2) add in the tetrahydrochysene anaerobic humulone of NaOH solution to 0.20 gram of 2 milliliters of 1N, make pH greater than 8, and then add in 10 milliliters of ethanol, do not add catalyzer; 3) and 4) respectively 1) and 2) condition under add catalyzer (10 milligrams of activated carbon powders that contain 5 weight % palladium metal) and react.Blowing air oxidation under agitation 1 hour, with the product in the efficient liquid phase chromatographic analysis alcoholic solution, calculate tetrahydrochysene humulone product and the ratio of the tetrahydrochysene anaerobic humulone original and mutual speed of reaction, result such as following table 1:
Table 1
| Alcoholic solution | Tetrahydrochysene humulone/tetrahydrochysene anaerobic humulone | The speed of reaction ratio | |
| 1) | Neutral | 0.028 | 1 |
| 2) | Alkalescence | 1.03 | 36 |
| 3) | Neutrality+palladium carbon dust | 0.057 | 2 |
| 4) | Alkalescence+palladium carbon dust | 2.60 | 92 |
Embodiment 2:
At room temperature, 0.02 the tetrahydrochysene anaerobic humulone of gram is dissolved in 10 milliliters of ethanol, stir and also to add 0.23 milliliter of 1N NaOH, react under described three kinds of different activated carbon or the situation of palladium carbon dust as following table not adding catalyzer or add 0.02 gram respectively then as catalyzer.Wherein 2) used activated carbon A is Colgon used activated carbon powder is common activated carbon powder (XHC coal-based) in, 3),
12 * 40, coal-based, 4) in used activated carbon B be Colgon, Centaur 12 * 40, coal-based, 5) in used palladium carbon dust be the activated carbon powder that contains the metallic palladium composition of 5% weight.After the blowing air oxidation 1 hour, analyze composition in these alcoholic solutions, calculate ratio and the relative reaction rate of tetrahydrochysene humulone, result such as following table 2 tetrahydrochysene anaerobic humulone with high performance liquid chromatograph:
Table 1
| Alcoholic solution | Tetrahydrochysene humulone/tetrahydrochysene anaerobic humulone | The speed of reaction ratio |
| 1) | Catalyst-free | 1.03 | 1 |
| 2) | Activated carbon powder | 1.13 | 1.1 |
| 3) | Activated carbon powder A | 1.56 | 1.5 |
| 4) | Activated carbon powder B | 2.00 | 1.9 |
| 5) | The palladium carbon dust | 2.60 | 2.5 |
Embodiment 3:
50 gram lupulone are dissolved in and contain in 5 milliliters of sulfuric acid and the 200 milliliters of ethanolic solns, add 1 gram and contain palladium carbon dust (wherein palladium accounts for 5% weight), place the hydrogenation groove hydrogen pressure be under 0.14MPa and the room temperature condition reaction after 1 hour hydrogenation finish.Get rid of remaining hydrogen, add the NaOH aqueous solution of 120 milliliters of 1N and sal epsom to the logical oxygen of alkalescence (pH8～9) or air (pressure is 1.4MPa) in reactive tank, be warming up to 75～80 ℃ gradually, 2.5 a hour afterreaction is finished, cooling off, being acidified to pH is 2.0, divide dried up oily two-phase after evaporating alcoholic solution, upper oil phase is dissolved in the ethanolic soln again, filter out catalyzer, revaporization falls alcohol and promptly gets 48 gram oily products, after the high performance liquid chromatograph analysis, contain 72% tetrahydro-iso-humulone in the fluid, ultimate production is 78%.
Embodiment 1 has clearly illustrated the catalysis of palladium carbon dust, and the speed that tetrahydrochysene anaerobic humulone is oxidized to the tetrahydrochysene humulone has increased by 2～3 times than catalyst-free, or bigger.Some activated carbon in embodiment 2 (not containing palladium) also has the effect of promotes oxidn reaction.Embodiment 3 is begun by lupulone, does the dual catalytic agent with the palladium carbon dust, and to be isomerizated into the reaction times of tetrahydro-iso-humulone be 2～2.5 hours in oxidation synchronously after hydrogenation, and relatively prior art is fast more than 1 times without the reaction times of catalyzer.This shows that method of the present invention has obvious improvement than prior art.
Claims (12)
1. one kind prepares the method for tetrahydro-iso-humulone from hop extract or lupulone oil, and this method may further comprise the steps:
(1) step of separation lupulone from hop extract or lupulone oil;
(2) be the step of tetrahydrochysene anaerobic humulone with lupulone hydrogenation under the effect of catalyzer;
And directly the tetrahydrochysene anaerobic humulone oxidation that contains catalyzer in the step (2) is isomerizated into step (3) but filtration catalizer, into tetrahydro-iso-humulone.
2. according to the process of claim 1 wherein that step (1) undertaken by following flow process:
Hop extract and alkaline aqueous solution are stirred under 25～100 ℃, regulate pH between 8～9.5, the lower floor's water that obtains is the humulone aqueous solution, and upper oil phase is a lupulone oil;
Lupulone oil and the alkaline aqueous solution that obtains stirred under 25～100 ℃ again, regulate pH between 9.5～12, the lower floor's water that obtains is the lupulone aqueous solution, and upper oil phase is a hop essential oil;
With after the humulone aqueous solution and the acidifying of lupulone aqueous solution difference, upper oil phase is respectively humulone and lupulone again.
3. according to the method for claim 2, wherein said alkaline aqueous solution is one or more the aqueous solution that is selected from following compound: KOH, NaOH, K
2CO
3, Na
2CO
3, Ca (OH)
2And Mg (OH)
2Wherein said acid is selected from one or more in phosphoric acid, hydrochloric acid, sulfuric acid, nitric acid and the carbonic acid.
4. according to the method for claim 1, the process that it is characterized in that step (2) is as follows: lupulone is dissolved in one or more blended alcoholic solvents that are selected from methyl alcohol, ethanol and propyl alcohol, in prepared alcoholic solution, add 0.1～5% acid based on whole alcoholic solution weight, wherein said acid is selected from one or more in phosphoric acid, hydrochloric acid, sulfuric acid, nitric acid and the carbonic acid, under hydrogen and catalyst action, carry out hydrogenation, temperature of reaction is 20～80 ℃, reaction times is 1～4 hour, hydrogen pressure is 0～2MPa, obtains the alcoholic solution of tetrahydrochysene anaerobic lupulone.
5. according to the method for claim 4, it is characterized in that described catalyzer is palladium carbon dust catalyzer or activated carbon; Wherein metallic palladium content is 0～20% of total catalyst weight, and catalyst consumption is 0.1～20% of the middle lupulone weight of step (2).
6. according to the method for claim 1, the flow process of step (3) is as follows: after the hydrogenation through step (2), the material that the alcoholic solution that does not filter out the reaction product tetrahydrochysene anaerobic humulone of catalyzer adds alkaline aqueous solution and is selected from one of group of comprising alkaline earth salt, alkaline earth metal oxide and both mixtures direct Hybrid Heating under air or oxygen, thereby make the humulone oxidation of tetrahydrochysene anaerobic and be isomerizated into tetrahydro-iso-humulone, acidifying filters out catalyzer, evaporates alcoholic solvent and promptly obtains tetrahydro-iso-humulone.
7. according to the method for claim 6, it is characterized in that wherein used alkaline earth salt or its oxide compound are selected from and comprise CaCO
3, MgCO
3, CaO, CaCl
2, CaSO
4, MgO, MgCl
2And MgSO
4In one or more; Described alkaline aqueous solution is one or more the aqueous solution that is selected from the following compound: KOH, NaOH, K
2CO
3, Na
2CO
3, Ca (OH)
2And Mg (OH)
2Wherein employed acid is selected from one or more in phosphoric acid, hydrochloric acid, sulfuric acid, nitric acid and the carbonic acid.
8. according to the method for claim 6, it is characterized in that air and oxygen pressure are 0～2MPa; Temperature of reaction is 50～80 ℃; The pH value of reaction soln is between 7～12.
9. according to the method for claim 1, the effect simultaneously synchronously oxidation of the tetrahydrochysene anaerobic humulone alcoholic solution that step (2) is obtained by catalyzer be isomerizated into into the process of tetrahydro-iso-humulone as follows: after the hydrogenation, in filtering out the reaction product alcoholic solution of catalyzer, add alkaline aqueous solution and alkaline earth salt, the activated carbon that adds catalytic amount again, directly mix and stir, heating makes its oxidation isomerization synchronously simultaneously under air or oxygen pressure, through acidifying and filtration, the evaporative removal alcoholic solution promptly obtains the tetrahydro-iso-humulone product.
10. according to the method for claim 9, it is characterized in that, make the catalyzer of oxidizing reaction with activated carbon powder, its consumption be in the step (2) lupulone weight 0.1～20%.
11. according to the method for claim 9, it is characterized in that air and oxygen pressure are 0～2MPa, temperature of reaction is 50～80 ℃, the pH value of solution is between 7～12.
12. according to the method for claim 9, wherein used alkaline earth salt or its oxide compound are selected from and comprise CaCO
3, MgCO
3, CaO, CaCl
2, CaSO
4, MgO, MgCl
2And MgSO
4In one or more; Described alkaline aqueous solution is one or more the aqueous solution that is selected from the following compound: KOH, NaOH, K
2CO
3, Na
2CO
3, Ca (OH)
2And Mg (OH)
2Wherein employed acid is selected from one or more in phosphoric acid, hydrochloric acid, sulfuric acid, nitric acid and the carbonic acid.
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|---|---|---|---|
| CN2006101123790A CN101134719B (en) | 2006-08-31 | 2006-08-31 | Method for preparing tetrahydrochysene isohumulone by hop concrete or lupulone oil |
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| CN2006101123790A CN101134719B (en) | 2006-08-31 | 2006-08-31 | Method for preparing tetrahydrochysene isohumulone by hop concrete or lupulone oil |
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| CN101134719B CN101134719B (en) | 2010-08-18 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102510898A (en) * | 2009-09-22 | 2012-06-20 | 卡拉马祖控股股份有限公司 | Process for the preparation of isohumulone compositions |
| CN102686548A (en) * | 2009-11-13 | 2012-09-19 | 卡拉马祖控股股份有限公司 | Process for the preparation of tetrahydroisohumulone compositions |
| CN105732347A (en) * | 2014-12-11 | 2016-07-06 | 北京理博兆禾酒花有限公司 | Method of hydrogenating and hydrogenolyzing mixture of [alpha]-acid derivative and [beta]-acid without solvent |
| CN107109314A (en) * | 2014-09-12 | 2017-08-29 | 公众有限责任公司 | When exposed to daylight or other UV and/or VIS light sources to skunk taste mercaptan local flavor degrade with reduction sensitiveness, especially insensitivity UV VIS transmit bottle in storage, provide, supply or consumption beer and its manufacture method |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4644084A (en) * | 1984-01-25 | 1987-02-17 | Miller Brewing Company | Preparation of tetrahydroisohumulones |
| CN1035993C (en) * | 1994-01-15 | 1997-10-01 | 沈阳佳源国际医疗科技有限公司 | Method for preparing tetrahydro-iso-humulone from hop extract |
| US6020019A (en) * | 1996-03-26 | 2000-02-01 | Miller Brewing Company | Hydrogenation of hop soft resins using CO2 |
| CN1058699C (en) * | 1998-10-06 | 2000-11-22 | 新疆大学 | Preparation of tetrahydroisoalpha acid from hops extract |
| AU778857B2 (en) * | 1999-11-18 | 2004-12-23 | S S Steiner Inc. | Process for the hydrogenation of hop resin acids |
-
2006
- 2006-08-31 CN CN2006101123790A patent/CN101134719B/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102510898A (en) * | 2009-09-22 | 2012-06-20 | 卡拉马祖控股股份有限公司 | Process for the preparation of isohumulone compositions |
| CN102510898B (en) * | 2009-09-22 | 2014-05-21 | 卡拉马祖控股股份有限公司 | Process for the preparation of isohumulone compositions |
| CN102686548A (en) * | 2009-11-13 | 2012-09-19 | 卡拉马祖控股股份有限公司 | Process for the preparation of tetrahydroisohumulone compositions |
| CN107109314A (en) * | 2014-09-12 | 2017-08-29 | 公众有限责任公司 | When exposed to daylight or other UV and/or VIS light sources to skunk taste mercaptan local flavor degrade with reduction sensitiveness, especially insensitivity UV VIS transmit bottle in storage, provide, supply or consumption beer and its manufacture method |
| US10988719B2 (en) | 2014-09-12 | 2021-04-27 | Ifast Nv | Method for producing beers stored, offered, served or consumed in UV-VIS-transmittant bottles with reduced sensitivity, in particular no sensitivity, to skunky thiol flavor degradation upon exposure to sunlight or other sources of UV and/or VIS light, and beers stored, offered, served or consumed in UV-VIS-transmittant bottles with reduced sensitivity, in particular no sensitivity, to skunky thiol flavor degradation upon exposure to sunlight or other sources of UV and/or VIS light |
| CN107109314B (en) * | 2014-09-12 | 2021-07-30 | 公众有限责任公司 | Beer stored, served or consumed in a UV-VIS-transmission bottle and method of making same |
| CN105732347A (en) * | 2014-12-11 | 2016-07-06 | 北京理博兆禾酒花有限公司 | Method of hydrogenating and hydrogenolyzing mixture of [alpha]-acid derivative and [beta]-acid without solvent |
| CN105732347B (en) * | 2014-12-11 | 2018-09-18 | 北京理博兆禾酒花有限公司 | The method of Solvent-free hydrogenation and hydrogenolysis alpha-acid derivative and the mixture of β acid |
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