NL8201095A - In meerdere trappen uitgevoerde katalytische omzetting van aldosen in alditolen. - Google Patents
In meerdere trappen uitgevoerde katalytische omzetting van aldosen in alditolen. Download PDFInfo
- Publication number
- NL8201095A NL8201095A NL8201095A NL8201095A NL8201095A NL 8201095 A NL8201095 A NL 8201095A NL 8201095 A NL8201095 A NL 8201095A NL 8201095 A NL8201095 A NL 8201095A NL 8201095 A NL8201095 A NL 8201095A
- Authority
- NL
- Netherlands
- Prior art keywords
- catalyst
- reaction zone
- feed
- reactor
- reaction
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 title claims description 128
- 230000003197 catalytic effect Effects 0.000 title claims description 24
- 150000005846 sugar alcohols Chemical class 0.000 title claims description 16
- 150000001323 aldoses Chemical class 0.000 title claims description 11
- 239000003054 catalyst Substances 0.000 claims description 108
- 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 58
- 229960001031 glucose Drugs 0.000 claims description 58
- 239000007788 liquid Substances 0.000 claims description 58
- 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 56
- 239000008103 glucose Substances 0.000 claims description 56
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 44
- 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 claims description 41
- 239000000600 sorbitol Substances 0.000 claims description 41
- 230000008569 process Effects 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000000243 solution Substances 0.000 claims description 25
- 238000002156 mixing Methods 0.000 claims description 23
- 229910052759 nickel Inorganic materials 0.000 claims description 23
- 239000000047 product Substances 0.000 claims description 23
- 239000012670 alkaline solution Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 229920001223 polyethylene glycol Polymers 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000012530 fluid Substances 0.000 claims description 8
- 238000006555 catalytic reaction Methods 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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 4
- 229930195725 Mannitol Natural products 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000003247 decreasing effect Effects 0.000 claims description 4
- 239000000594 mannitol Substances 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 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 2
- 244000061456 Solanum tuberosum Species 0.000 claims description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
- 238000011144 upstream manufacturing Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims 1
- 238000012258 culturing Methods 0.000 claims 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 229910052814 silicon oxide Inorganic materials 0.000 claims 1
- 239000000811 xylitol Substances 0.000 claims 1
- 235000010447 xylitol Nutrition 0.000 claims 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims 1
- 229960002675 xylitol Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 10
- 150000002772 monosaccharides Chemical class 0.000 description 9
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 6
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000174 gluconic acid Substances 0.000 description 6
- 235000012208 gluconic acid Nutrition 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- -1 glucose Chemical class 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 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 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 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 2
- 239000005715 Fructose Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940077731 carbohydrate nutrients Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000003541 multi-stage reaction Methods 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 238000013021 overheating Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920002488 Hemicellulose Polymers 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
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000013736 caramel Nutrition 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 244000221110 common millet Species 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000159 nickel phosphate Inorganic materials 0.000 description 1
- JOCJYBPHESYFOK-UHFFFAOYSA-K nickel(3+);phosphate Chemical compound [Ni+3].[O-]P([O-])([O-])=O JOCJYBPHESYFOK-UHFFFAOYSA-K 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/26—Hexahydroxylic alcohols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/258,225 US4433184A (en) | 1981-04-27 | 1981-04-27 | Multi-stage catalytic conversion of aldoses to alditols |
| US25822581 | 1981-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8201095A true NL8201095A (nl) | 1982-11-16 |
Family
ID=22979625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8201095A NL8201095A (nl) | 1981-04-27 | 1982-03-16 | In meerdere trappen uitgevoerde katalytische omzetting van aldosen in alditolen. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4433184A (fa) |
| JP (1) | JPS57181029A (fa) |
| BE (1) | BE892968A (fa) |
| CH (1) | CH651538A5 (fa) |
| DE (1) | DE3214432A1 (fa) |
| ES (1) | ES8305782A1 (fa) |
| FR (1) | FR2504523B1 (fa) |
| GB (1) | GB2097390B (fa) |
| NL (1) | NL8201095A (fa) |
| ZA (1) | ZA822326B (fa) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3403973A1 (de) * | 1984-02-04 | 1985-08-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung eines gemisches von (alpha)-d-glucopyranosido-1,6-mannit und (alpha)-d-glucopyranosido-1,6-sorbit aus (alpha)-d-glucopyranosido-1,6-fructose |
| FR2566801B1 (fr) * | 1984-06-29 | 1986-12-26 | Roquette Freres | Procede de preparation de sirops de sorbitol de tres haute purete |
| US4694113A (en) * | 1986-06-04 | 1987-09-15 | Pfizer Inc. | Dual catalyst sequential method for production of sorbitol from hydrolyzed starch solution |
| USH918H (en) | 1988-10-05 | 1991-05-07 | The United States Of America As Represented By The United States Department Of Energy | Decarbonylation and dehydrogenation of carbohydrates |
| DE3934457A1 (de) * | 1989-10-14 | 1991-04-18 | Bayer Ag | Verfahren zur herstellung von sorbitol (d-glucitol) aus (alpha)-d-glucose |
| DE4416115A1 (de) * | 1994-05-06 | 1995-11-09 | Bayer Ag | Verfahren zur Herstellung von alpha-D-Glucopyranosido-1,6-mannit und -sorbit aus alpha-D-Glucopyranosido-1,6-fructose |
| DE4416408A1 (de) * | 1994-05-10 | 1995-11-16 | Bayer Ag | Verfahren zur Hydrierung von Zuckern |
| DE19701991A1 (de) * | 1997-01-22 | 1998-07-23 | Bayer Ag | Verfahren zur Hydrierung von Zuckern |
| DE10024542A1 (de) * | 2000-05-18 | 2001-11-22 | Basf Ag | Verfahren zur Herstellung von gesättigten C3-C20-Alkoholen |
| US7278988B2 (en) | 2000-12-15 | 2007-10-09 | Kimberly-Clark Worldwide, Inc. | Dual-use pantiliner |
| JP5081368B2 (ja) * | 2001-11-29 | 2012-11-28 | ウィスコンシン アルムニ リサーチ ファンデイション | 酸化炭化水素からの低温水素生成 |
| US6699457B2 (en) * | 2001-11-29 | 2004-03-02 | Wisconsin Alumni Research Foundation | Low-temperature hydrogen production from oxygenated hydrocarbons |
| JP4574354B2 (ja) * | 2002-05-10 | 2010-11-04 | ウィスコンシン アルムニ リサーチ ファンデイション | 低温における酸化炭化水素からの炭化水素製造 |
| MY148259A (en) | 2005-12-21 | 2013-03-29 | Virent Inc | Catalysts and methods for reforming oxygenated compounds |
| GB2437517A (en) * | 2006-04-27 | 2007-10-31 | Danisco Sweeteners Oy | Catalytic hydrogenation of sugar to sugar alcohol, using increasing reaction temperature and/or addition of monocarboxylic acid to maintain catalyst activity |
| AU2007353527B2 (en) | 2006-12-20 | 2012-12-20 | Virent, Inc. | Reactor system for producing gaseous products |
| US20100094066A1 (en) * | 2007-01-17 | 2010-04-15 | The Curators Of The University Of Missouri | Gas phase reaction process for polyhydric compounds |
| PL2698416T3 (pl) * | 2007-03-08 | 2021-02-08 | Virent, Inc. | Synteza paliw ciekłych z węglowodorów zawierających tlen |
| US8017818B2 (en) | 2007-03-08 | 2011-09-13 | Virent Energy Systems, Inc. | Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons |
| CN102203034A (zh) | 2008-08-27 | 2011-09-28 | 维仁特能源系统公司 | 从生物质合成液体燃料 |
| WO2011019465A2 (en) * | 2009-08-13 | 2011-02-17 | Catalytic Distillation Technologies | Integrated biodiesel production process |
| WO2014055650A1 (en) * | 2012-10-02 | 2014-04-10 | The Michigan Biotechnology Institute | Integrated systems and methods for organic acid production |
| CN113956301B (zh) * | 2021-11-24 | 2023-06-27 | 浙江大学 | 一种用于糖醇生产的多釜串联连续加氢的方法及装置 |
| CN117603009A (zh) * | 2024-01-24 | 2024-02-27 | 山东天力药业有限公司 | 一种山梨醇的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE889890C (de) * | 1950-04-06 | 1953-09-14 | Bataafsche Petroleum | Verfahren zur Herstellung mehrwertiger Alkohole durch katalytische Reduktion von Kohlehydraten |
| US2650941A (en) * | 1950-04-06 | 1953-09-01 | Shell Dev | Conversion of carbohydrates to polyhydric alcohols |
| NL302696A (fa) * | 1962-12-31 | |||
| DE1268606B (de) * | 1962-12-31 | 1968-05-22 | Atlas Chem Ind | Verfahren zur Herstellung von Mannit und Sorbit |
| DE1300918B (de) * | 1967-07-21 | 1969-08-14 | Ruhrchemie Ag | Verfahren zur Herstellung mehrwertiger Alkohole durch katalytische Hydrierung von Kohlenhydraten |
| US3670035A (en) * | 1968-03-07 | 1972-06-13 | Atlas Chem Ind | Preparation of polyhydric alcohols from carbohydrates |
| US3763246A (en) * | 1970-03-09 | 1973-10-02 | Ici America Inc | Process for producing mannitol |
| AU6339073A (en) * | 1972-12-18 | 1975-06-12 | Colonial Sugar Refining | Catalytic hydrogenation |
| CA1107764A (en) * | 1978-03-30 | 1981-08-25 | Walter M. Kruse | High mannitol process (alkaline hydrogenation in presence of alkali metal carbonate) |
| DE2831719A1 (de) * | 1978-07-19 | 1980-01-31 | Bayer Ag | Verfahren zur herstellung von niedermolekularen polyhydroxylverbindungen |
| DD147842B1 (de) * | 1979-12-14 | 1987-01-07 | Heinz Aring | Verfahren zur kontinuierlichen hydrierung von glucose |
| US4322569A (en) * | 1980-08-01 | 1982-03-30 | Hydrocarbon Research, Inc. | Catalytic hydrogenation of glucose to produce sorbitol |
-
1981
- 1981-04-27 US US06/258,225 patent/US4433184A/en not_active Expired - Fee Related
-
1982
- 1982-03-16 NL NL8201095A patent/NL8201095A/nl not_active Application Discontinuation
- 1982-03-29 GB GB88209203A patent/GB2097390B/en not_active Expired
- 1982-04-05 ZA ZA822326A patent/ZA822326B/xx unknown
- 1982-04-20 DE DE19823214432 patent/DE3214432A1/de not_active Withdrawn
- 1982-04-21 JP JP57065555A patent/JPS57181029A/ja active Granted
- 1982-04-23 ES ES511666A patent/ES8305782A1/es not_active Expired
- 1982-04-26 CH CH2523/82A patent/CH651538A5/de not_active IP Right Cessation
- 1982-04-26 BE BE0/207924A patent/BE892968A/fr not_active IP Right Cessation
- 1982-04-27 FR FR8207248A patent/FR2504523B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH651538A5 (de) | 1985-09-30 |
| DE3214432A1 (de) | 1982-11-18 |
| BE892968A (fr) | 1982-10-26 |
| US4433184A (en) | 1984-02-21 |
| FR2504523B1 (fr) | 1985-11-22 |
| JPH0332533B2 (fa) | 1991-05-13 |
| ES511666A0 (es) | 1983-04-16 |
| JPS57181029A (en) | 1982-11-08 |
| GB2097390B (en) | 1985-05-09 |
| FR2504523A1 (fr) | 1982-10-29 |
| ZA822326B (en) | 1983-03-30 |
| ES8305782A1 (es) | 1983-04-16 |
| GB2097390A (en) | 1982-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: HRI, INC. |
|
| BV | The patent application has lapsed |