CA1058634A - Process for producing pure racemic acid and mesotartaric acid - Google Patents
Process for producing pure racemic acid and mesotartaric acidInfo
- Publication number
- CA1058634A CA1058634A CA246,655A CA246655A CA1058634A CA 1058634 A CA1058634 A CA 1058634A CA 246655 A CA246655 A CA 246655A CA 1058634 A CA1058634 A CA 1058634A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- free
- process according
- hydrolysis
- alkali
- 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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 title claims abstract description 123
- 238000000034 method Methods 0.000 title claims abstract description 69
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 title claims abstract description 54
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 64
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 55
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 54
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000011976 maleic acid Substances 0.000 claims abstract description 51
- DCEMCPAKSGRHCN-UHFFFAOYSA-N oxirane-2,3-dicarboxylic acid Chemical compound OC(=O)C1OC1C(O)=O DCEMCPAKSGRHCN-UHFFFAOYSA-N 0.000 claims abstract description 44
- 230000007062 hydrolysis Effects 0.000 claims abstract description 36
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 30
- 150000001450 anions Chemical class 0.000 claims abstract description 29
- 239000003513 alkali Substances 0.000 claims abstract description 25
- CYUUZGXOQDCCGH-UHFFFAOYSA-N dodecyl dodecanoate Chemical compound CCCCCCCCCCCCOC(=O)CCCCCCCCCCC CYUUZGXOQDCCGH-UHFFFAOYSA-N 0.000 claims abstract description 25
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 239000012452 mother liquor Substances 0.000 claims abstract description 19
- 238000002425 crystallisation Methods 0.000 claims abstract description 18
- 230000008025 crystallization Effects 0.000 claims abstract description 18
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001768 cations Chemical class 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 238000001704 evaporation Methods 0.000 claims abstract description 12
- 150000002688 maleic acid derivatives Chemical class 0.000 claims abstract description 4
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000011347 resin Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 230000008929 regeneration Effects 0.000 claims description 11
- 238000011069 regeneration method Methods 0.000 claims description 11
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 11
- 229910052721 tungsten Inorganic materials 0.000 claims description 11
- 239000010937 tungsten Substances 0.000 claims description 11
- 239000004793 Polystyrene Substances 0.000 claims description 10
- 229920002223 polystyrene Polymers 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 238000006735 epoxidation reaction Methods 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- -1 peroxide compounds Chemical class 0.000 claims description 6
- 238000001640 fractional crystallisation Methods 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- 239000011148 porous material Substances 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052681 coesite Inorganic materials 0.000 claims description 2
- 229910052906 cristobalite Inorganic materials 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 229910052682 stishovite Inorganic materials 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052905 tridymite Inorganic materials 0.000 claims description 2
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims 1
- 239000000243 solution Substances 0.000 description 64
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 21
- 235000002906 tartaric acid Nutrition 0.000 description 21
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 20
- 239000007864 aqueous solution Substances 0.000 description 19
- 229960002163 hydrogen peroxide Drugs 0.000 description 19
- 229960001367 tartaric acid Drugs 0.000 description 16
- 239000011975 tartaric acid Substances 0.000 description 16
- 229940048879 dl tartaric acid Drugs 0.000 description 13
- 239000001530 fumaric acid Substances 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 238000005349 anion exchange Methods 0.000 description 7
- 230000002349 favourable effect Effects 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 230000001172 regenerating effect Effects 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 239000000061 acid fraction Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 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
- 239000003957 anion exchange resin Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- GUPPESBEIQALOS-UHFFFAOYSA-L calcium tartrate Chemical compound [Ca+2].[O-]C(=O)C(O)C(O)C([O-])=O GUPPESBEIQALOS-UHFFFAOYSA-L 0.000 description 3
- 239000001427 calcium tartrate Substances 0.000 description 3
- 235000011035 calcium tartrate Nutrition 0.000 description 3
- 238000005341 cation exchange Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 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 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052602 gypsum Inorganic materials 0.000 description 2
- 239000010440 gypsum Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229910020350 Na2WO4 Inorganic materials 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- HDRTWMBOUSPQON-ODZAUARKSA-L calcium;(z)-but-2-enedioate Chemical compound [Ca+2].[O-]C(=O)\C=C/C([O-])=O HDRTWMBOUSPQON-ODZAUARKSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DCEMCPAKSGRHCN-JCYAYHJZSA-N trans-2,3-epoxysuccinic acid Chemical compound OC(=O)[C@@H]1O[C@H]1C(O)=O DCEMCPAKSGRHCN-JCYAYHJZSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- B01J23/90—Regeneration or reactivation
- B01J23/92—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2508228A DE2508228C3 (de) | 1975-02-26 | 1975-02-26 | Verfahren zur Herstellung von reiner Traubensäure und von Mesoweinsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058634A true CA1058634A (en) | 1979-07-17 |
Family
ID=5939822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA246,655A Expired CA1058634A (en) | 1975-02-26 | 1976-02-26 | Process for producing pure racemic acid and mesotartaric acid |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT334330B (de) |
| BE (1) | BE827604A (de) |
| CA (1) | CA1058634A (de) |
| DE (1) | DE2508228C3 (de) |
| SE (1) | SE426059B (de) |
| ZA (1) | ZA761030B (de) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101759554A (zh) * | 2009-12-31 | 2010-06-30 | 杭州临安金龙化工有限公司 | 一种处理和利用酒石酸氢钾母液的方法 |
| TWI480259B (zh) * | 2009-06-02 | 2015-04-11 | Akzo Nobel Chemicals Int Bv | 包含內消旋酒石酸之組合物的製備方法 |
| CN115253364A (zh) * | 2022-08-10 | 2022-11-01 | 安徽海蓝生物科技有限公司 | 一种酒石酸溶液的离心工艺及离心设备 |
| CN115286498A (zh) * | 2022-08-23 | 2022-11-04 | 佳化化学科技发展(上海)有限公司 | 一种内消旋酒石酸的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2754325A (en) * | 1952-05-27 | 1956-07-10 | Shell Dev | Oxidation with peroxides |
| DE1643891A1 (de) * | 1967-10-05 | 1971-05-19 | Degussa | Verfahren zur Herstellung von Calciumtartrat |
| DE2140055C3 (de) * | 1971-08-10 | 1980-10-02 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen | Verfahren zur Herstellung von Traubensäure |
| JPS5136249B2 (de) * | 1973-01-13 | 1976-10-07 | ||
| DE2542536C3 (de) * | 1975-09-24 | 1982-05-19 | Degussa Ag, 6000 Frankfurt | Abbindeverzögerer für technische Gipsplaster |
-
1975
- 1975-02-26 DE DE2508228A patent/DE2508228C3/de not_active Expired
- 1975-02-28 AT AT155775A patent/AT334330B/de not_active IP Right Cessation
- 1975-04-04 BE BE6044978A patent/BE827604A/xx not_active IP Right Cessation
-
1976
- 1976-02-20 ZA ZA1030A patent/ZA761030B/xx unknown
- 1976-02-25 SE SE7602406A patent/SE426059B/xx not_active IP Right Cessation
- 1976-02-26 CA CA246,655A patent/CA1058634A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI480259B (zh) * | 2009-06-02 | 2015-04-11 | Akzo Nobel Chemicals Int Bv | 包含內消旋酒石酸之組合物的製備方法 |
| CN101759554A (zh) * | 2009-12-31 | 2010-06-30 | 杭州临安金龙化工有限公司 | 一种处理和利用酒石酸氢钾母液的方法 |
| CN101759554B (zh) * | 2009-12-31 | 2013-08-14 | 杭州临安金龙化工有限公司 | 一种处理和利用酒石酸氢钾母液的方法 |
| CN115253364A (zh) * | 2022-08-10 | 2022-11-01 | 安徽海蓝生物科技有限公司 | 一种酒石酸溶液的离心工艺及离心设备 |
| CN115253364B (zh) * | 2022-08-10 | 2023-10-31 | 安徽海蓝生物科技有限公司 | 一种酒石酸溶液的离心工艺及离心设备 |
| CN115286498A (zh) * | 2022-08-23 | 2022-11-04 | 佳化化学科技发展(上海)有限公司 | 一种内消旋酒石酸的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AT334330B (de) | 1976-01-10 |
| ZA761030B (en) | 1977-01-26 |
| SE426059B (sv) | 1982-12-06 |
| BE827604A (fr) | 1975-10-06 |
| ATA155775A (de) | 1976-05-15 |
| SE7602406L (sv) | 1976-08-27 |
| DE2508228C3 (de) | 1987-01-22 |
| DE2508228B2 (de) | 1979-12-13 |
| DE2508228A1 (de) | 1976-09-09 |
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