HRP20200135T1 - Metoda odvajanja izoprenskih sastojaka guayule - Google Patents
Metoda odvajanja izoprenskih sastojaka guayule Download PDFInfo
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- HRP20200135T1 HRP20200135T1 HRP20200135TT HRP20200135T HRP20200135T1 HR P20200135 T1 HRP20200135 T1 HR P20200135T1 HR P20200135T T HRP20200135T T HR P20200135TT HR P20200135 T HRP20200135 T HR P20200135T HR P20200135 T1 HRP20200135 T1 HR P20200135T1
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- argentatin
- guayulin
- subjected
- precipitate
- purified
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- 238000000034 method Methods 0.000 title claims 21
- 238000000926 separation method Methods 0.000 title claims 7
- LOVYCUYJRWLTSU-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(Cl)C(Cl)=C1 LOVYCUYJRWLTSU-UHFFFAOYSA-N 0.000 title claims 3
- 241001495453 Parthenium argentatum Species 0.000 title claims 3
- 239000000470 constituent Substances 0.000 title claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 21
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 16
- 239000003208 petroleum Substances 0.000 claims 14
- 239000002244 precipitate Substances 0.000 claims 14
- JYEVPOCBZDNGDL-UHFFFAOYSA-N Guayulin A Natural products C1C(C)=CCCC(C)=CC(C2(C)C)C2C1OC(=O)C=CC1=CC=CC=C1 JYEVPOCBZDNGDL-UHFFFAOYSA-N 0.000 claims 13
- JYEVPOCBZDNGDL-ISCJZRRASA-N [(1s,2z,6z,9s,10r)-3,7,11,11-tetramethyl-9-bicyclo[8.1.0]undeca-2,6-dienyl] (e)-3-phenylprop-2-enoate Chemical compound O([C@@H]1[C@@H]2[C@@H](C2(C)C)\C=C(C)/CC/C=C(C1)/C)C(=O)\C=C\C1=CC=CC=C1 JYEVPOCBZDNGDL-ISCJZRRASA-N 0.000 claims 13
- IMZLIOGSDVHHAJ-UHFFFAOYSA-N argentatin D Natural products C12C(C)CCC(C(C)(C)O)OC2CC2(C)C1(C)CCC13CC3(CCC(O)C3(C)C)C3CCC12 IMZLIOGSDVHHAJ-UHFFFAOYSA-N 0.000 claims 13
- 229930189678 Guayulin Natural products 0.000 claims 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- BRSJEZNEKATFHB-UHFFFAOYSA-N argentatin B Natural products CC1CCCC(OC2CC3(C)C4CCC5C(C)(C)C(=O)CCC56CC46CCC3(C)C12)C(C)(C)O BRSJEZNEKATFHB-UHFFFAOYSA-N 0.000 claims 11
- KCYOWUNRFWIOTH-UHFFFAOYSA-N dethio-tetra(methylthio)chetomin Natural products C12C(C)CCC(C(C)(C)O)OC2CC2(C)C1(C)CCC13CC3(CCC(=O)C3(C)C)C3CCC12 KCYOWUNRFWIOTH-UHFFFAOYSA-N 0.000 claims 11
- 239000012454 non-polar solvent Substances 0.000 claims 11
- AHOBTXNYSMZYDP-UHFFFAOYSA-N argentatin C Natural products CC(CCC(O)C(C)(C)O)C1C(O)CC2(C)C3CCC4C(C)(C)C(=O)CCC45CC35CCC12C AHOBTXNYSMZYDP-UHFFFAOYSA-N 0.000 claims 9
- 238000002425 crystallisation Methods 0.000 claims 9
- 230000008025 crystallization Effects 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 238000001816 cooling Methods 0.000 claims 8
- 239000000284 extract Substances 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- RBRKRLQNZMJOLD-VXNHWSESSA-N CC(C)(O)[C@H]1CC[C@](C)(O1)[C@H]1[C@@H](O)C[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CCC(=O)C4(C)C Chemical compound CC(C)(O)[C@H]1CC[C@](C)(O1)[C@H]1[C@@H](O)C[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CCC(=O)C4(C)C RBRKRLQNZMJOLD-VXNHWSESSA-N 0.000 claims 7
- CGCTVTOHSPHPNF-UHFFFAOYSA-N argentatin A Natural products CC(C)(O)C(O)CCC(C)(O)C1C(O)CC2(C)C3CCC4C(C)(C)C(CCC45CC35CCC12C)OC6OC(CO)C(O)C(O)C6OC7OC(CO)C(O)C(O)C7O CGCTVTOHSPHPNF-UHFFFAOYSA-N 0.000 claims 7
- RBRKRLQNZMJOLD-UHFFFAOYSA-N beta-Mono-Me ester ‘«Ù(Z)-Aconitic acid Natural products O1C(C(C)(O)C)CCC1(C)C1C2(C)CCC34CC4(CCC(=O)C4(C)C)C4CCC3C2(C)CC1O RBRKRLQNZMJOLD-UHFFFAOYSA-N 0.000 claims 7
- 239000013078 crystal Substances 0.000 claims 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 239000007788 liquid Substances 0.000 claims 6
- 239000002798 polar solvent Substances 0.000 claims 5
- 239000011347 resin Substances 0.000 claims 5
- 229920005989 resin Polymers 0.000 claims 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- QKHYXKLHIXEAGP-UHFFFAOYSA-N Partheniol Natural products CC(=C)C1CCC(C)(O)C2CC=C(C)C2C1 QKHYXKLHIXEAGP-UHFFFAOYSA-N 0.000 claims 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 4
- 239000011159 matrix material Substances 0.000 claims 4
- DYXWUZXSAMLWND-UHFFFAOYSA-N partheniol Natural products OC1CC(C)=CCCC(C)=CC2C(C)(C)C12 DYXWUZXSAMLWND-UHFFFAOYSA-N 0.000 claims 4
- 238000001556 precipitation Methods 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 238000006722 reduction reaction Methods 0.000 claims 3
- 239000012279 sodium borohydride Substances 0.000 claims 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 3
- 239000006228 supernatant Substances 0.000 claims 3
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims 2
- 241000196324 Embryophyta Species 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 230000008020 evaporation Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- 229910010084 LiAlH4 Inorganic materials 0.000 claims 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000000287 crude extract Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- -1 lithium aluminum hydride Chemical compound 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 238000005192 partition Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000000935 solvent evaporation Methods 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
- B01D17/02—Separation of non-miscible liquids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0018—Evaporation of components of the mixture to be separated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/005—Selection of auxiliary, e.g. for control of crystallisation nuclei, of crystal growth, of adherence to walls; Arrangements for introduction thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C1/00—Treatment of rubber latex
- C08C1/02—Chemical or physical treatment of rubber latex before or during concentration
- C08C1/04—Purifying; Deproteinising
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/32—All rings being cycloaliphatic the ring system containing at least eleven carbon atoms
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- Polymers & Plastics (AREA)
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- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
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Claims (20)
1. Metoda za odvajanje najmanje jednog izoprenskog sastojka iz smole biljke guayule i/ili tipa guayula obuhvaća korake:
a) osiguravanje odmašćene smole guayule i/ili tipa guayule;
b) podvrgavanje navedene odmašćene smole podjeli tekuće-tekućeg tipa sa otapalima koji se međusobno ne miješaju čime se dobiva nepolarni ekstrakt koji sadrži izoprenske sastojke guayulin A, guayulin B i argentatin B; i polarni ekstrakt koji sadrži izoprenske sastojke argentatin A, argentatin C i argentatin D; i
c) odvajanje najmanje jednog izoprenskog sastojka iz navedenog polarnog ekstrakta i/ili iz navedenog nepolarnog ekstrakta tako dobivenih, pri čemu korak c) sadrži korak u kojem je navedeni polarni ekstrakt podvrgnut podjeli tekuće-tekućeg tipa sa otapalima koji se međusobno ne miješaju i/ili korak u kojem je navedeni nepolarni ekstrakt podvrgnut podjeli čvrsto-tekućeg tipa.
2. Metoda prema patentnom zahtjevu 1, gdje navedeni najmanje jedan izoprenski sastojak je izabran iz grupe koja sadrži guayulin A, guayulin B, argentatin A, argentatin B, argentatin C, argentatin D, i njihove smjese.
3. Metoda prema patentnom zahtjevu 1 ili 2, gdje se navedena odmašćena smola iz koraka a) dobiva korakom odmašćivanja, poželjnije korakom frakcione kristalizacije, sirovog ekstrakta biljke guayule ili tipa guayule.
4. Metoda prema bilo kojem od prethodnih patentnih zahtjeva, gdje, u koraku b), otapala koja se međusobno ne miješaju sadrže polarno otapalo i nepolarno otapalo, pri čemu poželjno polarno otapalo je izabran iz grupe koja sadrži vodu, metanol, etanol, izopropanol, terc-butanol, etil acetat, i njihove kombinacije, poželjnije otapalo metanola i vode; a nepolarno otapalo je izabran između naftnog etera, n-heksana i njihovih kombinacija, poželjnije naftni eter.
5. Metoda prema bilo kojem od prethodnih patentnih zahtjeva, gdje, u koraku c), podjela čvrsto-tekućeg tipa sadrži korake podvrgavanja nepolarnog ekstrakta dobivenog u koraku b), otopljenog u kombinaciji dva otapala koji se međusobno miješaju, adsorpciji na čvrstoj matrici, poželjno selektivnim hvatanjem; i obrade, poželjno ispiranja, navedene čvrste matrice tako dobivene kombinacijom dva otapala koji se međusobno miješaju, čime se dobiva otapalo koje sadrži smjesu guayulina A i guayulina B, i čvrstu matricu koja sadrži argentatin B.
6. Metoda prema patentnom zahtjevu 5, gdje navedena čvrsta matrica koja sadrži argentatin B je podvrgnuta daljoj obradi, poželjno ispiranju polarnim otapalom, čime se dobiva otopina argentatina B.
7. Metoda prema bilo kojem od prethodnih patentnih zahtjeva, gdje, u koraku c), podjela tekuće-tekućeg tipa sadrži korak podvrgavanja polarnog ekstrakta dobivenog u koraku b) odvajanju u kombinaciji polarnog otapala i nepolarnog otapala čime se dobiva organska faza koja sadrži argentatin A i vodena faza koja sadrži smjesu argentatina C i argentatina D.
8. Metoda prema patentnom zahtjevu 7, gdje u koraku podjele tekuće-tekućeg tipa iz koraka c), nepolarno otapalo je izabran iz grupe koja sadrži cikloheksan, n-heksan, naftni eter, i njihove kombinacije, poželjnije cikloheksan; a polarno otapalo je izabrano iz grupe koja sadrži vodu, metanol, etanol, izopropanol, terc-butanol, i njihove kombinacije, poželjno metanol i vodu.
9. Metoda prema bilo kojem od prethodnih patentnih zahtjeva, gdje nakon koraka c) sledi najmanje jedan korak d) prečišćavanja najmanje jednog navedenog izoprenskog sastojka.
10. Metoda prema patentnom zahtjevu 9 gdje korak prečišćavanja d) sadrži korak kristalizacije najmanje jednog izoprenskog sastojka, čime se dobiva najmanje jedan izoprenski sastojak smole u suštinski čistom kristalnom obliku.
11. Metoda prema patentnom zahtjevu 9 ili 10, gdje korak d) sadrži korak d1) pri čemu navedena smjesa guayulina A i guayulina B dobivena u koraku c) je podvrgnuta taloženju guayulina A tretmanom sa nepolarnim otapalom, poželjno izabranim iz grupe koja sadrži naftni eter, n-heksan i njihove kombinacije, poželjnije n-heksan, uz hlađenje, čime se dobiva talog pročišćenog guayulina A i supernatant koji sadrži smjesu guayulina A i guayulina B; i gdje poželjno, navedeni talog pročišćenog guayulina A je podvrgnut kristalizaciji tako da se dobiju kristali čistog guayulina A.
12. Metoda prema bilo kojem od patentnih zahtjeva 9 do 11, gdje spomenuti korak d) sadrži korak d2) pri čemu navedeni argentatin B dobiven u koraku c) je podvrgnut taloženju sa nepolarnim otapalom, poželjno izabranim iz grupe koja sadrži naftni eter, n-heksan i njihove kombinacije, poželjnije naftni eter, uz hlađenje, čime se dobiva talog pročišćenog argentatina B; i gdje poželjno navedeni talog pročišćenog argentatina B je podvrgnut kristalizaciji tako da se dobiju kristali čistog argentatina B.
13. Metoda prema bilo kojem od patentnih zahtjeva 9 do 12, gdje navedeni korak d) sadrži korak d3) pri čemu navedeni argentatin A dobiven u koraku c) je podvrgnut taloženju sa nepolarnim otapalom, poželjno izabranim iz grupe koja sadrži cikloheksan, n-heksan, etil eter, naftni eter, i njihove kombinacije, poželjnije etil eter i n-heksan, uz hlađenje, čime se dobiva talog pročišćenog argentatina A; i gdje poželjno navedeni talog pročišćenog argentatina A je podvrgnut kristalizaciji tako da se dobiju kristali čistog argentatina A.
14. Metoda prema bilo kojem od patentnih zahtjeva 9 do 13, gdje navedeni korak d) sadrži korak d4) pri čemu navedena smjesa argentatina C i argentatina D dobivena u koraku c) je podvrgnuta taloženju argentatina D sa nepolarnim otapalom, poželjno izabranim iz grupe koja sadrži naftni eter, n-heksan i njihove kombinacije, poželjnije naftni eter, uz hlađenje, čime se dobiva talog pročišćenog argentatina D i supernatant koji sadrži argentatin C; i gdje poželjno navedeni talog pročišćenog argentatina D je podvrgnut kristalizaciji tako da se dobiju kristali čistog argentatina D.
15. Metoda prema patentnom zahtjevu 14, gdje navedeni korak d4) je praćen korakom d5) pri čemu navedeni supernatant koji sadrži argentatin C je podvrgnut uparivanju otapala a ostatak se otapa u nepolarnom otapalu, poželjno izabranom iz grupe koja sadrži cikloheksan, naftni eter, etil eter, n-heksan i njihove kombinacije, poželjnije etil eter, uz hlađenje, čime se dobiva talog pročišćenog argentatina C; i gdje poželjno navedeni talog pročišćenog argentatina C je podvrgnut kristalizaciji tako da se dobiju kristali čistog argentatina C.
16. Metoda prema bilo kojem od patentnih zahtjeva 5 do 15, gdje navedeni korak c) je praćen korakom e1) koji sadrži reakciju bazne hidrolize guayulina A dobivenog u koraku d1) i/ili smjese guayulina A i guayulina B dobivene u koraku c) čime se dobiva otopina koji sadrži parteniol; gdje poželjno navedena reakcija bazne hidrolize je izvedena u reakcijskoj smjesi koja sadrži navedeni guayulin A i/ili navedenu smjesu guayulina A i guayulina B i bazno otapalo; i gdje poželjno navedena otopina koji sadrži parteniol je podvrgnut kristalizaciji, uz hlađenje, čime se dobiva čist parteniol.
17. Metoda prema patentnom zahtjevu 16, gdje navedeni korak e1) je praćen korakom e2) esterifikacije tako dobivenog parteniola, poželjno sa anisnom kiselinom ili anizoil kloridom čime se dobiva otopina koji sadrži guayulin B.
18. Metoda prema patentnom zahtjevu 17, gdje navedena otopina koji sadrži guayulin B tako dobiven u koraku e2) se podvrgava uparivanju a ostatak se otapa u nepolarnom otapalu, poželjno izabranom iz grupe koja sadrži cikloheksan, n-heksan, etil eter, naftni eter i njihove kombinacije, poželjnije naftni eter, čime se dobiva talog pročišćenog guayulina B; i gdje poželjno spomenuti talog pročišćenog guayulina B je podvrgnut kristalizaciji, uz hlađenje, čime se dobivaju kristali čistog guayulina B.
19. Metoda prema bilo kojem od patentnih zahtjeva 5 do 18 gdje navedeni korak c) je praćen korakom e3) koji sadrži reakciju redukcije argentatina B dobivenog u koraku c) i/ili u koraku d2), poželjno gdje je reakcija redukcije izvedena u reakcijskoj smjesi koja sadrži navedeni argentatin B i litij aluminij hidrid LiAlH4 ili natrij borohidrid, poželjnije natrij borohidrid NaBH4, čime se dobiva otopina koji sadrži argentatin D.
20. Metoda prema patentnom zahtjevu 19, gdje, nakon spomenute reakcije redukcije, spomenuta otopina koji sadrži argentatin D tako dobiven je podvrgnut uparivanju i ostatak je otopljen u nepolarnom otapalu, poželjno izabranom iz grupe koja sadrži cikloheksan, etil eter, n-heksan, naftni eter i njihove kombinacije, poželjnije naftni eter, tako dobivajući talog pročišćenog argentatina D; i gdje poželjno navedeni talog pročišćenog argentatina D je podvrgnut kristalizaciji, uz hlađenje, čime se dobivanju kristali čistog argentatina D.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITUB2015A002746A ITUB20152746A1 (it) | 2015-07-31 | 2015-07-31 | Metodo per la separazione dei costituenti isoprenici del guayule. |
| PCT/IB2016/054578 WO2017021852A1 (en) | 2015-07-31 | 2016-07-29 | Method for the separation of the isoprenic constituents of guayule |
| EP16757959.8A EP3328874B1 (en) | 2015-07-31 | 2016-07-29 | Method for the separation of the isoprenic constituents of guayule |
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| HRP20200135T1 true HRP20200135T1 (hr) | 2020-08-21 |
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| HRP20200135TT HRP20200135T1 (hr) | 2015-07-31 | 2020-01-29 | Metoda odvajanja izoprenskih sastojaka guayule |
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| US (1) | US10570312B2 (hr) |
| EP (1) | EP3328874B1 (hr) |
| JP (1) | JP6776326B2 (hr) |
| CN (1) | CN107709346B (hr) |
| BR (1) | BR112017026757B1 (hr) |
| CY (1) | CY1122620T1 (hr) |
| DK (1) | DK3328874T3 (hr) |
| ES (1) | ES2770005T3 (hr) |
| HR (1) | HRP20200135T1 (hr) |
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| ITUB20159400A1 (it) * | 2015-12-14 | 2017-06-14 | Versalis Spa | Procedimento per l?estrazione di lattice, resina e gomma da piante di guayule. |
| CN109096112B (zh) * | 2018-09-20 | 2021-06-18 | 上海诗丹德标准技术服务有限公司 | 款冬酮的制备方法 |
| JP2024501212A (ja) * | 2020-12-17 | 2024-01-11 | 株式会社ブリヂストン | グアユール樹脂の抽出 |
| CN117443077B (zh) * | 2023-10-27 | 2024-03-15 | 临沂广辰化工有限公司 | 一种菊酸乙酯提纯加工装置及方法 |
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| US4739038A (en) * | 1987-01-30 | 1988-04-19 | The Firestone Tire & Rubber Company | Process for the controlled partition of guayule resin |
| US20090099309A1 (en) * | 2007-10-16 | 2009-04-16 | Yulex Corporation | Guayule resin multipolymer |
| WO2016062753A1 (en) | 2014-10-22 | 2016-04-28 | Versalis S.P.A. | Integrated process for processing and utilising the guayule plant |
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| LT3328874T (lt) | 2020-04-10 |
| ES2770005T3 (es) | 2020-06-30 |
| JP2018522890A (ja) | 2018-08-16 |
| CN107709346B (zh) | 2020-11-03 |
| EP3328874B1 (en) | 2019-11-06 |
| RU2704821C2 (ru) | 2019-10-31 |
| US20180171178A1 (en) | 2018-06-21 |
| CN107709346A (zh) | 2018-02-16 |
| DK3328874T3 (da) | 2020-02-10 |
| PL3328874T3 (pl) | 2020-07-27 |
| US10570312B2 (en) | 2020-02-25 |
| RS59889B1 (sr) | 2020-03-31 |
| SI3328874T1 (sl) | 2020-04-30 |
| WO2017021852A1 (en) | 2017-02-09 |
| RU2018105348A (ru) | 2019-08-29 |
| MY185910A (en) | 2021-06-14 |
| MX2018001048A (es) | 2018-06-07 |
| JP6776326B2 (ja) | 2020-10-28 |
| RU2018105348A3 (hr) | 2019-08-29 |
| EP3328874A1 (en) | 2018-06-06 |
| BR112017026757B1 (pt) | 2021-09-28 |
| PT3328874T (pt) | 2020-02-10 |
| HUE048056T2 (hu) | 2020-05-28 |
| CY1122620T1 (el) | 2021-03-12 |
| BR112017026757A2 (pt) | 2018-08-21 |
| ITUB20152746A1 (it) | 2017-01-31 |
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