CA1292988C - Procede de separation de la psicose d'autres cetoses - Google Patents

Procede de separation de la psicose d'autres cetoses

Info

Publication number: CA1292988C
Authority: CA; Canada
Prior art keywords: psicose; adsorbent; extract; fructose; raffinate
Prior art date: 1987-08-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA000544233A

Other languages

English (en)

Inventor

Chin-Hsiung Chang

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Honeywell UOP LLC

Original Assignee

UOP LLC

Priority date (The priority date 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 date listed.)

1987-08-11

Filing date

1987-08-11

Publication date

1991-12-10

1987-08-11 Application filed by UOP LLC filed Critical UOP LLC

1987-08-11 Priority to CA000544233A priority Critical patent/CA1292988C/fr

1991-12-10 Application granted granted Critical

1991-12-10 Publication of CA1292988C publication Critical patent/CA1292988C/fr

2008-12-10 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 62
230000008569 process Effects 0.000 title claims abstract description 52
LKDRXBCSQODPBY-JDJSBBGDSA-N D-allulose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@H]1O LKDRXBCSQODPBY-JDJSBBGDSA-N 0.000 title claims abstract description 51
208000007976 Ketosis Diseases 0.000 title claims abstract description 25
150000002584 ketoses Chemical class 0.000 title claims abstract description 25
239000003463 adsorbent Substances 0.000 claims abstract description 109
239000000203 mixture Substances 0.000 claims abstract description 58
238000000926 separation method Methods 0.000 claims abstract description 39
239000010457 zeolite Substances 0.000 claims abstract description 36
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims abstract description 35
229930091371 Fructose Natural products 0.000 claims abstract description 34
239000005715 Fructose Substances 0.000 claims abstract description 34
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 31
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 31
238000003795 desorption Methods 0.000 claims abstract description 21
238000001179 sorption measurement Methods 0.000 claims abstract description 19
-1 calcium cations Chemical class 0.000 claims abstract description 15
150000002772 monosaccharides Chemical class 0.000 claims abstract description 15
239000011575 calcium Substances 0.000 claims abstract description 13
229910052791 calcium Inorganic materials 0.000 claims abstract description 12
125000002091 cationic group Chemical group 0.000 claims abstract description 3
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 claims description 16
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 claims description 16
239000008103 glucose Substances 0.000 claims description 14
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
BJHIKXHVCXFQLS-ZXEDONINSA-N L-psicose Chemical compound OC[C@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-ZXEDONINSA-N 0.000 claims description 7
LKDRXBCSQODPBY-NSHGFSBMSA-N L-fructose Chemical compound OCC1(O)OC[C@H](O)[C@H](O)[C@H]1O LKDRXBCSQODPBY-NSHGFSBMSA-N 0.000 claims description 6
WQZGKKKJIJFFOK-ZZWDRFIYSA-N L-glucose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-ZZWDRFIYSA-N 0.000 claims description 5
LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 claims description 3
WQZGKKKJIJFFOK-JFNONXLTSA-N L-mannopyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-JFNONXLTSA-N 0.000 claims description 3
ZAQJHHRNXZUBTE-NQXXGFSBSA-N D-ribulose Chemical compound OC[C@@H](O)[C@@H](O)C(=O)CO ZAQJHHRNXZUBTE-NQXXGFSBSA-N 0.000 claims description 2
ZAQJHHRNXZUBTE-UHFFFAOYSA-N D-threo-2-Pentulose Natural products OCC(O)C(O)C(=O)CO ZAQJHHRNXZUBTE-UHFFFAOYSA-N 0.000 claims description 2
BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 claims description 2
150000001323 aldoses Chemical class 0.000 abstract description 12
BJHIKXHVCXFQLS-PUFIMZNGSA-N D-psicose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C(=O)CO BJHIKXHVCXFQLS-PUFIMZNGSA-N 0.000 abstract description 3
230000007717 exclusion Effects 0.000 abstract 1
239000000463 material Substances 0.000 description 65
150000001768 cations Chemical group 0.000 description 12
230000000274 adsorptive effect Effects 0.000 description 11
239000007787 solid Substances 0.000 description 11
238000006317 isomerization reaction Methods 0.000 description 10
235000000346 sugar Nutrition 0.000 description 10
239000012071 phase Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
230000000694 effects Effects 0.000 description 6
239000012530 fluid Substances 0.000 description 6
239000002245 particle Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
150000008163 sugars Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 5
230000014759 maintenance of location Effects 0.000 description 5
239000000700 radioactive tracer Substances 0.000 description 5
229910000323 aluminium silicate Inorganic materials 0.000 description 4
150000001720 carbohydrates Chemical class 0.000 description 4
235000014633 carbohydrates Nutrition 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000006073 displacement reaction Methods 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000011148 porous material Substances 0.000 description 4
238000011144 upstream manufacturing Methods 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
229930182830 galactose Natural products 0.000 description 3
150000004676 glycans Chemical class 0.000 description 3
150000002574 ketohexoses Chemical class 0.000 description 3
150000002581 ketopentoses Chemical class 0.000 description 3
229920001282 polysaccharide Polymers 0.000 description 3
239000005017 polysaccharide Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000001320 aldopentoses Chemical class 0.000 description 2
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000005341 cation exchange Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
150000003839 salts Chemical group 0.000 description 2
230000003068 static effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012546 transfer Methods 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
239000011800 void material Substances 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical group C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
GZCGUPFRVQAUEE-UHFFFAOYSA-N 2,3,4,5,6-pentahydroxyhexanal Chemical compound OCC(O)C(O)C(O)C(O)C=O GZCGUPFRVQAUEE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
WQZGKKKJIJFFOK-WHZQZERISA-N D-aldose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-WHZQZERISA-N 0.000 description 1
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
ZAQJHHRNXZUBTE-WUJLRWPWSA-N D-xylulose Chemical compound OC[C@@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-WUJLRWPWSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
150000001299 aldehydes Chemical group 0.000 description 1
150000001312 aldohexoses Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
238000013459 approach Methods 0.000 description 1
PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000013461 design Methods 0.000 description 1
230000009881 electrostatic interaction Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012013 faujasite Substances 0.000 description 1
238000004858 feed analysis Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000002402 hexoses Chemical class 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052909 inorganic silicate Inorganic materials 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000004001 molecular interaction Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
150000002972 pentoses Chemical class 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000010926 purge Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000001223 reverse osmosis Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000021309 simple sugar Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000002336 sorption--desorption measurement Methods 0.000 description 1

Landscapes

Treatment Of Liquids With Adsorbents In General (AREA)

CA000544233A 1987-08-11 1987-08-11 Procede de separation de la psicose d'autres cetoses Expired - Fee Related CA1292988C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000544233A CA1292988C (fr)	1987-08-11	1987-08-11	Procede de separation de la psicose d'autres cetoses

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000544233A CA1292988C (fr)	1987-08-11	1987-08-11	Procede de separation de la psicose d'autres cetoses

Publications (1)

Publication Number	Publication Date
CA1292988C true CA1292988C (fr)	1991-12-10

Family

ID=4136241

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000544233A Expired - Fee Related CA1292988C (fr)	1987-08-11	1987-08-11	Procede de separation de la psicose d'autres cetoses

Country Status (1)

Country	Link
CA (1)	CA1292988C (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2156751A1 (fr)	2007-05-18	2010-02-24	Matsutani Chemical Industry Co., Ltd.	Edulcorant inédit au goût de sucre, son procédé de fabrication et son utilisation
US9854827B2 (en)	2013-03-15	2018-01-02	Tate & Lyle Ingredients Americas Llc	Sweetener
WO2018116272A1 (fr) *	2016-12-23	2018-06-28	Petiva Private Ltd.	Procédé de séparation de cétoses
WO2019231393A1 (fr) *	2018-05-31	2019-12-05	Ngee Ann Polytechnic	Production de d-psicose en utilisant des micro-organismes probiotiques

1987
- 1987-08-11 CA CA000544233A patent/CA1292988C/fr not_active Expired - Fee Related

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2156751A1 (fr)	2007-05-18	2010-02-24	Matsutani Chemical Industry Co., Ltd.	Edulcorant inédit au goût de sucre, son procédé de fabrication et son utilisation
US20100204346A1 (en) *	2007-05-18	2010-08-12	Matsutani Chemical Industry Co., Ltd.	Novel sweetener having sucrose-like taste, method for producing the same, and use of the same
EP2156751B1 (fr) *	2007-05-18	2018-10-03	Matsutani Chemical Industry Co., Ltd.	Edulcorant inédit au goût de sucre, son procédé de fabrication et son utilisation
US9854827B2 (en)	2013-03-15	2018-01-02	Tate & Lyle Ingredients Americas Llc	Sweetener
WO2018116272A1 (fr) *	2016-12-23	2018-06-28	Petiva Private Ltd.	Procédé de séparation de cétoses
WO2019231393A1 (fr) *	2018-05-31	2019-12-05	Ngee Ann Polytechnic	Production de d-psicose en utilisant des micro-organismes probiotiques
US11401536B2 (en)	2018-05-31	2022-08-02	Ngee Ann Polytechnic	D-psicose production using probiotic microorganisms

Legal Events

Date	Code	Title	Description
1994-06-12	MKLA	Lapsed

Publication	Publication Date	Title
US4692514A (en)	1987-09-08	Process for separating ketoses from alkaline- or pyridine-catalyzed isomerization products
CA1152501A (fr)	1983-08-23	Separation du fructose dans un melange de sucres
US4248737A (en)	1981-02-03	Technique to reduce the zeolite molecular sieve solubility in an aqueous system
CA1217782A (fr)	1987-02-10	Separation en vrac de l'inositol et du sorbitol par adsorption selective sur des tamis moleculaires zeolitiques
FI73240B (fi)	1987-05-29	Separation av arabinos genom selektiv adsorption i zeolitmolekylsaoll.
US4238243A (en)	1980-12-09	Technique to reduce the zeolite molecular sieve solubility in an aqueous system
US4372876A (en)	1983-02-08	Zeolite molecular sieve adsorbent for an aqueous system
US4319929A (en)	1982-03-16	Simulated countercurrent sorption process employing ion exchange resins with periodic backflushing
US4295994A (en)	1981-10-20	Cellulose acetate butyrate bound zeolite adsorbents
US4373025A (en)	1983-02-08	Process for the isomerization of glucose
US4857642A (en)	1989-08-15	Process for separating arabinose from a mixture of other aldoses
US4337171A (en)	1982-06-29	Organic bound adsorbents
US4405377A (en)	1983-09-20	Process for the separation of monosaccharides
US4316819A (en)	1982-02-23	Technique to reduce the zeolite molecular sieve solubility in an aqueous system
US4431456A (en)	1984-02-14	Technique to reduce the zeolite molecular sieve solubility in an aqueous system
US4340724A (en)	1982-07-20	Process for separating a ketose from an aldose by selective adsorption
US4880920A (en)	1989-11-14	Process for separating ketoses from alkaline-or pyridine-catalyzed isomerization products
US4664718A (en)	1987-05-12	Process for separating arabinose from a pentose/hexose mixture
US4298501A (en)	1981-11-03	Technique to reduce the zeolite molecular sieve solubility in an aqueous system
US4345946A (en)	1982-08-24	Process for use of a zeolite molecular sieve adsorbent in an aqueous system
US5000794A (en)	1991-03-19	Process for separating glucose and mannose with dealuminated Y zeolites
US4226639A (en)	1980-10-07	Silica guard bed for adsorbent used in an aqueous system
US4421567A (en)	1983-12-20	Separatory process using organic bound adsorbents
US4325742A (en)	1982-04-20	Rare earth cation exchanged adsorbents for carbohydrate separations
US4442285A (en)	1984-04-10	Process for separating glucose from fructose by selective adsorption