CA3090459A1 - Method for producing functional crystalline sweetener - Google Patents
Method for producing functional crystalline sweetener Download PDFInfo
- Publication number
- CA3090459A1 CA3090459A1 CA3090459A CA3090459A CA3090459A1 CA 3090459 A1 CA3090459 A1 CA 3090459A1 CA 3090459 A CA3090459 A CA 3090459A CA 3090459 A CA3090459 A CA 3090459A CA 3090459 A1 CA3090459 A1 CA 3090459A1
- Authority
- CA
- Canada
- Prior art keywords
- allulose
- crystal
- composition
- crystallization
- conversion material
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 30
- 235000003599 food sweetener Nutrition 0.000 title abstract description 14
- 239000003765 sweetening agent Substances 0.000 title abstract description 14
- 239000013078 crystal Substances 0.000 claims abstract description 204
- 238000000034 method Methods 0.000 claims abstract description 152
- 238000002425 crystallisation Methods 0.000 claims abstract description 132
- 230000008025 crystallization Effects 0.000 claims abstract description 127
- 230000001965 increasing effect Effects 0.000 claims abstract description 33
- LKDRXBCSQODPBY-JDJSBBGDSA-N D-allulose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@H]1O LKDRXBCSQODPBY-JDJSBBGDSA-N 0.000 claims description 531
- 239000000463 material Substances 0.000 claims description 127
- 238000006243 chemical reaction Methods 0.000 claims description 122
- 239000000203 mixture Substances 0.000 claims description 56
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 52
- 238000004458 analytical method Methods 0.000 claims description 45
- 238000000926 separation method Methods 0.000 claims description 30
- 239000007787 solid Substances 0.000 claims description 23
- 238000001816 cooling Methods 0.000 claims description 21
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims description 20
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 19
- 238000004587 chromatography analysis Methods 0.000 claims description 18
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims description 17
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 claims description 16
- 239000012141 concentrate Substances 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 12
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 10
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 10
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000441 X-ray spectroscopy Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 8
- DSLRVRBSNLHVBH-UHFFFAOYSA-N 2,5-furandimethanol Chemical compound OCC1=CC=C(CO)O1 DSLRVRBSNLHVBH-UHFFFAOYSA-N 0.000 claims description 8
- JOPTYRBQYCIAFR-UHFFFAOYSA-N 2-formylfuran-3-carboxylic acid Chemical compound OC(=O)C=1C=COC=1C=O JOPTYRBQYCIAFR-UHFFFAOYSA-N 0.000 claims description 8
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 8
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000010828 elution Methods 0.000 claims description 6
- 229940040102 levulinic acid Drugs 0.000 claims description 5
- PXJJKVNIMAZHCB-UHFFFAOYSA-N 2,5-diformylfuran Chemical compound O=CC1=CC=C(C=O)O1 PXJJKVNIMAZHCB-UHFFFAOYSA-N 0.000 claims description 4
- WXFWXFIWDGJRSC-UHFFFAOYSA-N 2,5-dimethoxy-2,5-dihydrofuran Chemical compound COC1OC(OC)C=C1 WXFWXFIWDGJRSC-UHFFFAOYSA-N 0.000 claims description 4
- JTABRXOUWGPDKM-UHFFFAOYSA-N 2-methyl-5-[(5-methylfuran-2-yl)methoxymethyl]furan Chemical compound O1C(C)=CC=C1COCC1=CC=C(C)O1 JTABRXOUWGPDKM-UHFFFAOYSA-N 0.000 claims description 4
- UBLUFCRWIXJFEJ-UHFFFAOYSA-N 5-[(5-carboxyfuran-2-yl)methyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)O1 UBLUFCRWIXJFEJ-UHFFFAOYSA-N 0.000 claims description 4
- QVYAWBLDJPTXHS-UHFFFAOYSA-N 5-hydroxyfuran-2-carbaldehyde Chemical compound OC1=CC=C(C=O)O1 QVYAWBLDJPTXHS-UHFFFAOYSA-N 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000012535 impurity Substances 0.000 abstract description 40
- 239000000243 solution Substances 0.000 description 62
- 239000002245 particle Substances 0.000 description 52
- 239000006188 syrup Substances 0.000 description 51
- 235000020357 syrup Nutrition 0.000 description 51
- 230000001276 controlling effect Effects 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 16
- 150000002500 ions Chemical class 0.000 description 16
- 238000000746 purification Methods 0.000 description 15
- 239000002994 raw material Substances 0.000 description 15
- 239000013081 microcrystal Substances 0.000 description 14
- 230000003247 decreasing effect Effects 0.000 description 13
- 238000006297 dehydration reaction Methods 0.000 description 13
- 235000008504 concentrate Nutrition 0.000 description 12
- 230000018044 dehydration Effects 0.000 description 11
- 238000009826 distribution Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000000376 reactant Substances 0.000 description 10
- 239000005715 Fructose Substances 0.000 description 9
- 229930091371 Fructose Natural products 0.000 description 9
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 9
- 238000007669 thermal treatment Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 7
- 238000004566 IR spectroscopy Methods 0.000 description 6
- 239000000498 cooling water Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 230000006355 external stress Effects 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- -1 crystalline fructose Chemical class 0.000 description 4
- 239000011549 crystallization solution Substances 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 229910001415 sodium ion Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000010170 biological method Methods 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000010183 spectrum analysis Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002402 hexoses Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000004376 Sucralose Substances 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- FTSSQIKWUOOEGC-RULYVFMPSA-N fructooligosaccharide Chemical compound OC[C@H]1O[C@@](CO)(OC[C@@]2(OC[C@@]3(OC[C@@]4(OC[C@@]5(OC[C@@]6(OC[C@@]7(OC[C@@]8(OC[C@@]9(OC[C@@]%10(OC[C@@]%11(O[C@H]%12O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%12O)O[C@H](CO)[C@@H](O)[C@@H]%11O)O[C@H](CO)[C@@H](O)[C@@H]%10O)O[C@H](CO)[C@@H](O)[C@@H]9O)O[C@H](CO)[C@@H](O)[C@@H]8O)O[C@H](CO)[C@@H](O)[C@@H]7O)O[C@H](CO)[C@@H](O)[C@@H]6O)O[C@H](CO)[C@@H](O)[C@@H]5O)O[C@H](CO)[C@@H](O)[C@@H]4O)O[C@H](CO)[C@@H](O)[C@@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O FTSSQIKWUOOEGC-RULYVFMPSA-N 0.000 description 1
- 229940107187 fructooligosaccharide Drugs 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 235000014109 instant soup Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000013365 molecular weight analysis method Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Seasonings (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20170083905 | 2017-06-30 | ||
| PCT/KR2018/001829 WO2019004554A1 (ko) | 2017-06-30 | 2018-02-12 | 결정형 기능성 감미료의 제조방법 |
| KRPCT/KR2018/001829 | 2018-02-12 | ||
| KR1020180172864A KR102424913B1 (ko) | 2017-06-30 | 2018-12-28 | 결정형 기능성 감미료의 제조방법 |
| KR10-2018-0172864 | 2018-12-28 | ||
| PCT/KR2019/001536 WO2019156483A1 (ko) | 2018-02-12 | 2019-02-07 | 결정형 기능성 감미료의 제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3090459A1 true CA3090459A1 (en) | 2019-08-15 |
Family
ID=65017283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3090459A Pending CA3090459A1 (en) | 2017-06-30 | 2019-02-07 | Method for producing functional crystalline sweetener |
Country Status (6)
| Country | Link |
|---|---|
| JP (3) | JP7178417B2 (zh) |
| KR (3) | KR102016701B1 (zh) |
| CN (1) | CN111741962B (zh) |
| AU (3) | AU2019217136A1 (zh) |
| CA (1) | CA3090459A1 (zh) |
| TW (2) | TWI713821B (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114031649A (zh) * | 2021-07-16 | 2022-02-11 | 山东福洋生物科技股份有限公司 | 一种提高阿洛酮糖晶体粒度和流动性的方法 |
| US11780870B2 (en) | 2020-12-04 | 2023-10-10 | Shandong Bailong Chuangyuan Bio-tech Co., Ltd. | Method for preparing crystalline D-psicose |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102016701B1 (ko) * | 2017-06-30 | 2019-09-06 | 주식회사 삼양사 | 결정형 기능성 감미료의 제조방법 |
| KR102590473B1 (ko) * | 2019-10-31 | 2023-10-17 | 주식회사 삼양사 | 개선된 알룰로스의 제조 방법 |
| CA3156624A1 (en) * | 2019-10-31 | 2021-05-06 | Jae-Kyung Yang | Improved method for manufacturing allulose |
| KR102616151B1 (ko) * | 2022-12-28 | 2023-12-20 | 주식회사 삼양사 | 알룰로스 결정 |
| KR102631972B1 (ko) * | 2022-12-29 | 2024-01-31 | 주식회사 삼양사 | 개선된 특성을 갖는 알룰로스 시럽 |
| KR102666581B1 (ko) * | 2022-12-30 | 2024-05-16 | 주식회사 삼양사 | 결정형 케스토스 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4761424B2 (ja) * | 2004-03-17 | 2011-08-31 | 株式会社希少糖生産技術研究所 | Ｌ−プシコース結晶、その製造方法および、糖試薬キット |
| KR101189640B1 (ko) | 2010-03-26 | 2012-10-12 | 씨제이제일제당 (주) | Ｄ-사이코스 결정을 제조하는 방법 |
| JP5922880B2 (ja) * | 2011-04-28 | 2016-05-24 | 松谷化学工業株式会社 | 結晶糖質、その製造方法ならびに用途 |
| KR101749527B1 (ko) * | 2014-10-20 | 2017-06-21 | 씨제이제일제당(주) | D-사이코스 결정을 제조하는 방법 |
| JP6982499B2 (ja) * | 2015-02-24 | 2021-12-17 | テート アンド ライル イングリーディエンツ アメリカズ エルエルシー | アルロースシロップ |
| KR101617379B1 (ko) * | 2015-05-13 | 2016-05-02 | 주식회사 삼양사 | 혼합당 과립 분말 및 이의 제조방법 |
| KR101981388B1 (ko) * | 2017-06-14 | 2019-05-22 | 씨제이제일제당 (주) | D-사이코스 결정을 제조하는 방법 |
| KR102016701B1 (ko) * | 2017-06-30 | 2019-09-06 | 주식회사 삼양사 | 결정형 기능성 감미료의 제조방법 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11780870B2 (en) | 2020-12-04 | 2023-10-10 | Shandong Bailong Chuangyuan Bio-tech Co., Ltd. | Method for preparing crystalline D-psicose |
| CN114031649A (zh) * | 2021-07-16 | 2022-02-11 | 山东福洋生物科技股份有限公司 | 一种提高阿洛酮糖晶体粒度和流动性的方法 |
Also Published As
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|---|---|
| TWI713821B (zh) | 2020-12-21 |
| KR20220110671A (ko) | 2022-08-09 |
| KR20190003308A (ko) | 2019-01-09 |
| KR20190098040A (ko) | 2019-08-21 |
| JP2023001356A (ja) | 2023-01-04 |
| AU2023201711A1 (en) | 2023-04-13 |
| CN111741962B (zh) | 2023-09-15 |
| JP2022118140A (ja) | 2022-08-12 |
| JP2021512882A (ja) | 2021-05-20 |
| CN111741962A (zh) | 2020-10-02 |
| TW201904445A (zh) | 2019-02-01 |
| KR102016701B1 (ko) | 2019-09-06 |
| AU2021286421B2 (en) | 2022-12-22 |
| KR102643143B1 (ko) | 2024-03-04 |
| AU2021286421A1 (en) | 2022-01-20 |
| KR102424913B1 (ko) | 2022-07-25 |
| AU2019217136A1 (en) | 2020-09-03 |
| TW202003538A (zh) | 2020-01-16 |
| JP7178417B2 (ja) | 2022-11-25 |
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