DE2947741C2 - Verfahren zur Herstellung von 2-Ketogulonsäure oder deren Salzen - Google Patents
Verfahren zur Herstellung von 2-Ketogulonsäure oder deren SalzenInfo
- Publication number
- DE2947741C2 DE2947741C2 DE2947741A DE2947741A DE2947741C2 DE 2947741 C2 DE2947741 C2 DE 2947741C2 DE 2947741 A DE2947741 A DE 2947741A DE 2947741 A DE2947741 A DE 2947741A DE 2947741 C2 DE2947741 C2 DE 2947741C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- diketogluconate
- borane
- reduction
- amine
- 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
- 239000002253 acid Substances 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 25
- 150000003839 salts Chemical class 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 29
- 229910000085 borane Inorganic materials 0.000 claims description 23
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- RXMWXENJQAINCC-DMTCNVIQSA-N 2,5-didehydro-D-gluconic acid Chemical compound OCC(=O)[C@@H](O)[C@H](O)C(=O)C(O)=O RXMWXENJQAINCC-DMTCNVIQSA-N 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 2
- RKFLKNFLAJISPF-OGXRZFKVSA-L calcium;(3s,4s)-3,4,6-trihydroxy-2,5-dioxohexanoate Chemical compound [Ca+2].OCC(=O)[C@@H](O)[C@H](O)C(=O)C([O-])=O.OCC(=O)[C@@H](O)[C@H](O)C(=O)C([O-])=O RKFLKNFLAJISPF-OGXRZFKVSA-L 0.000 description 33
- 238000006722 reduction reaction Methods 0.000 description 22
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- VBUYCZFBVCCYFD-JJYYJPOSSA-N 2-dehydro-D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-JJYYJPOSSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 11
- 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 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 229960005070 ascorbic acid Drugs 0.000 description 9
- 235000010323 ascorbic acid Nutrition 0.000 description 9
- 239000011668 ascorbic acid Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000003638 chemical reducing agent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 5
- 238000000855 fermentation Methods 0.000 description 5
- 230000004151 fermentation Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000001030 gas--liquid chromatography Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- -1 sodium Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000007787 solid Substances 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- RJTANRZEWTUVMA-UHFFFAOYSA-N boron;n-methylmethanamine Chemical compound [B].CNC RJTANRZEWTUVMA-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011946 reduction process Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JYHRLWMNMMXIHF-UHFFFAOYSA-N (tert-butylamino)boron Chemical compound [B]NC(C)(C)C JYHRLWMNMMXIHF-UHFFFAOYSA-N 0.000 description 1
- GGZZISOUXJHYOY-UHFFFAOYSA-N 8-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1O GGZZISOUXJHYOY-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- JBANFLSTOJPTFW-UHFFFAOYSA-N azane;boron Chemical compound [B].N JBANFLSTOJPTFW-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- QFLVHLKRNQNMGT-UHFFFAOYSA-N boron;methanamine Chemical compound [B].NC QFLVHLKRNQNMGT-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- KPHIBLNUVRGOGU-WDCZJNDASA-N methyl (3s,4r,5r)-3,4,5,6-tetrahydroxy-2-oxohexanoate Chemical compound COC(=O)C(=O)[C@@H](O)[C@H](O)[C@H](O)CO KPHIBLNUVRGOGU-WDCZJNDASA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000011916 stereoselective reduction Methods 0.000 description 1
- 239000012607 strong cation exchange resin Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96562678A | 1978-12-01 | 1978-12-01 | |
| US06/024,284 US4212988A (en) | 1979-03-26 | 1979-03-26 | Preparation of 2-ketogulonic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2947741A1 DE2947741A1 (de) | 1980-06-04 |
| DE2947741C2 true DE2947741C2 (de) | 1982-07-01 |
Family
ID=26698275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2947741A Expired DE2947741C2 (de) | 1978-12-01 | 1979-11-27 | Verfahren zur Herstellung von 2-Ketogulonsäure oder deren Salzen |
Country Status (10)
| Country | Link |
|---|---|
| CA (1) | CA1140147A (fr) |
| CH (1) | CH641472A5 (fr) |
| DE (1) | DE2947741C2 (fr) |
| DK (1) | DK154649C (fr) |
| FR (1) | FR2442855A1 (fr) |
| GB (1) | GB2036740B (fr) |
| IE (1) | IE49219B1 (fr) |
| IT (1) | IT1126454B (fr) |
| LU (1) | LU81936A1 (fr) |
| NL (1) | NL177313C (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX4533E (es) * | 1976-12-10 | 1982-06-03 | Pfizer | Procedimiento para preparar una mezcla de 2-cetogulonato y2-cetogluconato |
-
1979
- 1979-11-06 DK DK470179A patent/DK154649C/da not_active IP Right Cessation
- 1979-11-27 GB GB7940847A patent/GB2036740B/en not_active Expired
- 1979-11-27 DE DE2947741A patent/DE2947741C2/de not_active Expired
- 1979-11-29 CH CH1063179A patent/CH641472A5/fr not_active IP Right Cessation
- 1979-11-29 IE IE2294/79A patent/IE49219B1/en not_active IP Right Cessation
- 1979-11-29 CA CA000340867A patent/CA1140147A/fr not_active Expired
- 1979-11-29 LU LU81936A patent/LU81936A1/fr unknown
- 1979-11-30 FR FR7929467A patent/FR2442855A1/fr active Granted
- 1979-11-30 IT IT27761/79A patent/IT1126454B/it active
- 1979-11-30 NL NLAANVRAGE7908678,A patent/NL177313C/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| IE792294L (en) | 1980-06-01 |
| GB2036740A (en) | 1980-07-02 |
| NL7908678A (nl) | 1980-06-03 |
| NL177313B (nl) | 1985-04-01 |
| LU81936A1 (fr) | 1980-06-05 |
| CA1140147A (fr) | 1983-01-25 |
| FR2442855B1 (fr) | 1983-02-25 |
| FR2442855A1 (fr) | 1980-06-27 |
| DK470179A (da) | 1980-06-02 |
| IE49219B1 (en) | 1985-08-21 |
| DE2947741A1 (de) | 1980-06-04 |
| GB2036740B (en) | 1983-01-19 |
| DK154649C (da) | 1989-05-08 |
| IT1126454B (it) | 1986-05-21 |
| DK154649B (da) | 1988-12-05 |
| IT7927761A0 (it) | 1979-11-30 |
| CH641472A5 (fr) | 1984-02-29 |
| NL177313C (nl) | 1985-09-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |