CA1217782A - Bulk separation of inositol and sorbitol by selective adsorption on zeolitic molecular sieves - Google Patents
Bulk separation of inositol and sorbitol by selective adsorption on zeolitic molecular sievesInfo
- Publication number
- CA1217782A CA1217782A CA000436042A CA436042A CA1217782A CA 1217782 A CA1217782 A CA 1217782A CA 000436042 A CA000436042 A CA 000436042A CA 436042 A CA436042 A CA 436042A CA 1217782 A CA1217782 A CA 1217782A
- Authority
- CA
- Canada
- Prior art keywords
- inositol
- zeolite
- sorbitol
- adsorbent
- mixture
- 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.)
- Expired
Links
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 title claims abstract description 102
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 title claims abstract description 102
- 229960000367 inositol Drugs 0.000 title claims abstract description 100
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 title claims abstract description 93
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 title claims abstract description 47
- 239000000600 sorbitol Substances 0.000 title claims abstract description 47
- 238000000926 separation method Methods 0.000 title claims abstract description 29
- 238000001179 sorption measurement Methods 0.000 title claims abstract description 20
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 title claims description 37
- 239000002808 molecular sieve Substances 0.000 title abstract description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 title abstract description 8
- 239000010457 zeolite Substances 0.000 claims abstract description 76
- 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 73
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 59
- 239000003463 adsorbent Substances 0.000 claims abstract description 47
- 150000001768 cations Chemical class 0.000 claims abstract description 21
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 9
- 229910052788 barium Inorganic materials 0.000 claims abstract description 8
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 47
- 150000001720 carbohydrates Chemical class 0.000 claims description 35
- 235000014633 carbohydrates Nutrition 0.000 claims description 35
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 13
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 8
- 239000011575 calcium Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 8
- 150000005846 sugar alcohols Chemical class 0.000 claims description 8
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 235000000346 sugar Nutrition 0.000 claims description 6
- -1 zeolite cations Chemical class 0.000 claims description 6
- 239000002156 adsorbate Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 229930091371 Fructose Natural products 0.000 description 14
- 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 14
- 239000005715 Fructose Substances 0.000 description 14
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 11
- 229930006000 Sucrose Natural products 0.000 description 11
- 239000005720 sucrose Substances 0.000 description 11
- 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 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000010828 elution Methods 0.000 description 10
- 239000008103 glucose Substances 0.000 description 10
- 230000014759 maintenance of location Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 5
- 244000144725 Amygdalus communis Species 0.000 description 4
- 235000011437 Amygdalus communis Nutrition 0.000 description 4
- 235000020224 almond Nutrition 0.000 description 4
- 229910052681 coesite Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052906 cristobalite Inorganic materials 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052682 stishovite Inorganic materials 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 229910052905 tridymite Inorganic materials 0.000 description 4
- 239000011800 void material Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 3
- 229920001202 Inulin Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 235000005822 corn Nutrition 0.000 description 3
- 238000003795 desorption Methods 0.000 description 3
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(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(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 3
- 229940029339 inulin Drugs 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 229940068041 phytic acid Drugs 0.000 description 3
- 235000002949 phytic acid Nutrition 0.000 description 3
- 239000000467 phytic acid Substances 0.000 description 3
- 239000002594 sorbent Substances 0.000 description 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- 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 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
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- PJVXUVWGSCCGHT-ZPYZYFCMSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-ZPYZYFCMSA-N 0.000 description 1
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229930091051 Arenine Natural products 0.000 description 1
- HQOWCDPFDSRYRO-CDKVKFQUSA-N CCCCCCc1ccc(cc1)C1(c2cc3-c4sc5cc(\C=C6/C(=O)c7ccccc7C6=C(C#N)C#N)sc5c4C(c3cc2-c2sc3cc(C=C4C(=O)c5ccccc5C4=C(C#N)C#N)sc3c12)(c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1 Chemical compound CCCCCCc1ccc(cc1)C1(c2cc3-c4sc5cc(\C=C6/C(=O)c7ccccc7C6=C(C#N)C#N)sc5c4C(c3cc2-c2sc3cc(C=C4C(=O)c5ccccc5C4=C(C#N)C#N)sc3c12)(c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1 HQOWCDPFDSRYRO-CDKVKFQUSA-N 0.000 description 1
- GUBGYTABKSRVRQ-UHFFFAOYSA-N D-Cellobiose Natural products OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 description 1
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- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 description 1
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- FGFCSHCXBYAKOL-UHFFFAOYSA-N cyclohexane-1,1,2,2,3,3-hexol Chemical class OC1(O)CCCC(O)(O)C1(O)O FGFCSHCXBYAKOL-UHFFFAOYSA-N 0.000 description 1
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 229940046001 vitamin b complex Drugs 0.000 description 1
- 238000001238 wet grinding Methods 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
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- 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
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41757782A | 1982-09-13 | 1982-09-13 | |
| IS417,577 | 1982-09-13 | ||
| US457,427 | 1983-01-12 | ||
| US06/457,427 US4482761A (en) | 1982-09-13 | 1983-01-12 | Bulk separation of inositol and sorbitol by selective adsorption on zeolitic molecular sieves |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1217782A true CA1217782A (en) | 1987-02-10 |
Family
ID=27023776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000436042A Expired CA1217782A (en) | 1982-09-13 | 1983-09-02 | Bulk separation of inositol and sorbitol by selective adsorption on zeolitic molecular sieves |
Country Status (7)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE33105E (en) * | 1982-12-30 | 1989-10-31 | Uop | Separation of mannose by selective adsorption on zeolitic molecular sieves |
| US4664718A (en) * | 1985-03-18 | 1987-05-12 | Uop Inc. | Process for separating arabinose from a pentose/hexose mixture |
| US4588847A (en) * | 1985-06-26 | 1986-05-13 | E. I. Du Pont De Nemours And Company | Process for separation of ethylene glycol and propylene glycol on selected zeolites |
| US5160756A (en) * | 1987-03-24 | 1992-11-03 | Itd Corporation | Extraction of products from almond fruit |
| US5064762A (en) * | 1987-05-07 | 1991-11-12 | Rabinowitz Israel N | Increasing the inositol yield from almond hulls |
| EP0327016B1 (en) * | 1988-02-02 | 1993-12-08 | Mitsubishi Kasei Corporation | Process for isolating and recovering erythritol from culture medium containing the same |
| US4997489A (en) * | 1989-05-08 | 1991-03-05 | Rabinowitz Israel N | Extraction of products from almond fruit |
| US5096594A (en) * | 1990-12-20 | 1992-03-17 | Israel Rabinowitz | Chromatographic method of purifying cyclitols |
| TW211560B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1991-03-14 | 1993-08-21 | Peilly Ind Inc | |
| IT1248012B (it) * | 1991-06-07 | 1995-01-05 | Mediolanum Farmaceutici Spa | Impiego del fosfatidilinositolo per la terapia dei disturbi della depressione. |
| FR2679229B1 (fr) * | 1991-07-16 | 1994-08-05 | Commissariat Energie Atomique | Procede de preparation du cis-inositol, du meso-inositol, de l'epi-inositol et/ou du cis-quercitol eventuellement deuteres. |
| FI96225C (fi) | 1993-01-26 | 1996-05-27 | Cultor Oy | Menetelmä melassin fraktioimiseksi |
| US6663780B2 (en) | 1993-01-26 | 2003-12-16 | Danisco Finland Oy | Method for the fractionation of molasses |
| US5387347A (en) * | 1993-09-15 | 1995-02-07 | Rothchild; Ronald D. | Method and apparatus for continuous chromatographic separation |
| US5795398A (en) | 1994-09-30 | 1998-08-18 | Cultor Ltd. | Fractionation method of sucrose-containing solutions |
| US5482631A (en) * | 1994-10-06 | 1996-01-09 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Separation of inositols from sugars and sugar alcohols |
| US6224776B1 (en) | 1996-05-24 | 2001-05-01 | Cultor Corporation | Method for fractionating a solution |
| CA2236641C (en) * | 1997-05-07 | 2008-07-15 | Cornell Research Foundation, Inc. | Preparation of fagopyritols and uses therefor |
| US6492341B1 (en) | 1997-05-07 | 2002-12-10 | Cornell Research Foundation, Inc. | Preparation of fagopyritols and uses therefor |
| JP4151089B2 (ja) * | 1997-10-07 | 2008-09-17 | 三菱化学株式会社 | 高純度エリスリトール結晶の製造方法 |
| FI20010977A7 (fi) | 2001-05-09 | 2002-11-10 | Danisco Sweeteners Oy | Kromatografinen erotusmenetelmä |
| CA2483550C (en) | 2002-05-09 | 2016-06-28 | Cornell Research Foundation, Inc. | Fagopyrum esculentum fagopyritol synthase gene and use thereof |
| EP2194140A2 (en) | 2005-03-02 | 2010-06-09 | Metanomics GmbH | Process for the production of fine chemicals |
| JP5734459B2 (ja) | 2011-12-20 | 2015-06-17 | 本田技研工業株式会社 | 自動車用繊維強化樹脂部材 |
| KR101447579B1 (ko) | 2012-09-26 | 2014-10-15 | 주식회사 디와이내츄럴 | 미생물을 이용한 ｄ-카이로 이노시톨의 생산 방법 |
| CN108866247A (zh) * | 2018-09-18 | 2018-11-23 | 上海立足生物科技有限公司 | 连续大规模分离制备d-阿洛酮糖的方法和设备 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2746957A (en) * | 1952-09-23 | 1956-05-22 | Benjamin Clayton | Recovery of water soluble inositol compounds and sterol glycosides |
| US3270064A (en) * | 1961-01-26 | 1966-08-30 | Toyo Koatsu Ind Inc | Method for preparation of i-inositol |
| JPS51106688A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1975-03-17 | 1976-09-21 | Toray Industries | |
| US4238243A (en) * | 1979-05-29 | 1980-12-09 | Uop Inc. | Technique to reduce the zeolite molecular sieve solubility in an aqueous system |
-
1983
- 1983-01-12 US US06/457,427 patent/US4482761A/en not_active Expired - Fee Related
- 1983-09-02 CA CA000436042A patent/CA1217782A/en not_active Expired
- 1983-09-13 GR GR72435A patent/GR81957B/el unknown
- 1983-09-13 IT IT67947/83A patent/IT1203678B/it active
- 1983-09-13 ES ES525568A patent/ES8600187A1/es not_active Expired
- 1983-09-13 PT PT77337A patent/PT77337B/pt not_active IP Right Cessation
-
1988
- 1988-05-17 JP JP63118409A patent/JPS646227A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS646227A (en) | 1989-01-10 |
| PT77337B (en) | 1986-02-06 |
| IT8367947A0 (it) | 1983-09-13 |
| PT77337A (en) | 1983-10-01 |
| ES525568A0 (es) | 1985-09-16 |
| IT1203678B (it) | 1989-02-15 |
| GR81957B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-12-12 |
| US4482761A (en) | 1984-11-13 |
| ES8600187A1 (es) | 1985-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |