CN104496806A - Synthetic method of L-dibenzoyl tartaric acid - Google Patents
Synthetic method of L-dibenzoyl tartaric acid Download PDFInfo
- Publication number
- CN104496806A CN104496806A CN201410836840.1A CN201410836840A CN104496806A CN 104496806 A CN104496806 A CN 104496806A CN 201410836840 A CN201410836840 A CN 201410836840A CN 104496806 A CN104496806 A CN 104496806A
- Authority
- CN
- China
- Prior art keywords
- tartaric acid
- dibenzoyl tartaric
- synthetic method
- toluene
- dibenzoyl
- 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.)
- Granted
Links
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 title claims abstract description 50
- 238000010189 synthetic method Methods 0.000 title claims abstract description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 81
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 229910000365 copper sulfate Inorganic materials 0.000 claims abstract description 10
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 9
- -1 L-dibenzoyl tartaric acid acid anhydride Chemical class 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 8
- 238000005119 centrifugation Methods 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 235000003891 ferrous sulphate Nutrition 0.000 claims description 4
- 239000011790 ferrous sulphate Substances 0.000 claims description 4
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 4
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 230000017105 transposition Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 20
- 239000002994 raw material Substances 0.000 abstract description 11
- 238000011084 recovery Methods 0.000 abstract description 10
- 238000000926 separation method Methods 0.000 abstract description 4
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 12
- 238000007664 blowing Methods 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019636 bitter flavor Nutrition 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
Abstract
The invention discloses a synthetic method of L-dibenzoyl tartaric acid. The synthetic method comprises the following steps: with L-tartaric acid and benzoyl chloride as raw materials, copper sulfate as a catalyst and toluene as a solvent, carrying out reaction to prepare L-dibenzoyl tartaric anhydride, carrying out hydrolysis with an equal amount of water and toluene to obtain the L-dibenzoyl tartaric acid, wherein the toluene serving as the solvent, as well as the water and the toluene in the hydrolysis step can be repeatedly utilized. With the adoption of the synthetic method, the process is simple, the operation is safe and easy, the process recovery ratio achieves above 95 percent, meanwhile, the cost of the raw materials is low, a part of the raw materials can be recovered and recycled, and a finished product is high in purity and excellent in chiral separation performance.
Description
Technical field
The present invention relates to a kind of chemical synthesis process technical field of chiral selectors, specifically a kind of synthetic method of L-dibenzoyl tartaric acid.
Background technology
L-dibenzoyl tartaric acid is a kind of white crystalline powder, and odorless, mildly bitter flavor, be slightly soluble in water, and pH value is 3-4, in acid, dissolves in ethanol and acetone and other organic solvent.Be widely used in chiral separation racemic amines compounds.And because it is cheap, stable in properties, and be easy to recycle and there is good industrial application value.Its molecular formula is as follows:
The defect of common synthetic method is: 1. raw material has strong and stimulating, severe corrosive, severe toxicity, not easy to operate.2. raw material availability is low, can not recycle, and production is polluted larger.3. process recovery ratio is low, and about 50%, product purity is lower, and production cost is higher.
Summary of the invention
Technical problem to be solved by this invention is the synthetic method providing a kind of L-dibenzoyl tartaric acid, the method technique is simple, safety is easy to operate, process recovery ratio reaches more than 95%, simultaneously, raw materials cost is lower, and part material is recyclable, finished product product purity is higher, has excellent chiral separation performance.
The synthetic method of L-dibenzoyl tartaric acid is: first with L-TARTARIC ACID (CAS:87-69-4), Benzoyl chloride (CAS:98-88-4) and sulfur oxychloride (CAS:7719-09-7) for raw material, take toluene as solvent, the obtained L-dibenzoyl tartaric acid acid anhydride of reaction, then L-dibenzoyl tartaric acid acid anhydride is added water through being hydrolyzed to obtain L-dibenzoyl tartaric acid.Reaction mechanism is as follows:
This method process recovery ratio about 50%.
In order to solve the technical problem that the present invention proposes, the technical scheme that the present invention proposes especially is: a kind of synthetic method of L-dibenzoyl tartaric acid, and synthesis step is:
(1) 1 part of L-TARTARIC ACID, is got by weight and appropriate organic solvent puts into reactor, under agitation, in reactor, add 0.1-0.001 part catalyzer, afterwards, in reactor, add 1 ~ 3 part of Benzoyl chloride with the drop rate of 1-10mL/min, after dropwising, continue reaction 4h, then, the mixture be obtained by reacting is turned to be incorporated in whizzer and carries out centrifugation, obtain solid L-dibenzoyl tartaric acid acid anhydride, for subsequent use;
Described catalyzer is copper sulfate or ferrous sulfate;
(2), the L-dibenzoyl tartaric acid acid anhydride that step (1) is obtained is put into reactor, and toluene and the water of weight such as to add wherein, reflux 2-4h under 100 DEG C of conditions, afterwards, be cooled to normal temperature, the mixture transposition obtained is carried out centrifugation in whizzer, obtains solid L-dibenzoyl tartaric acid.
In step (1) and step (2), the rotating speed of centrifugation is 100-1000 r/min.
Solvent in described step (1) is toluene.
In described step (1), the add-on of toluene and the ratio of L-TARTARIC ACID are 1L/0.75kg.
Rate of temperature fall in described step (2) is 5-10 DEG C/min.
Stirring velocity in described step (1) is 500-3000r/min.
Beneficial effect compared with the method that the above method of the present invention and employing sulfur oxychloride are raw material is:
1, the method technique of this synthesis L-dibenzoyl tartaric acid is simple, and manipulation is convenient, and mild condition, avoids the application of toxic substance sulfur oxychloride, improves the safe operability of technique; As the copper sulfate of catalyzer or adding of ferrous sulfate, substantially reduce the reaction times of technique, improve product yield and the quality product of technique; Meanwhile, low raw-material cost used, the recycling capable of circulation such as the solvent used in process, reduces production cost, decreases environmental pollution, be conducive to scale operation.
2, the L-dibenzoyl tartaric acid final product quality purity of the method synthesis reaches more than 99%, and technique product yield reaches more than 95%, has excellent chiral separation performance.
Accompanying drawing explanation
Fig. 1 is the XRD figure of the L-dibenzoyl tartaric acid that embodiment 1 obtains;
Fig. 2 is the XRD figure of the L-dibenzoyl tartaric acid that embodiment 2 obtains;
Fig. 3 is the XRD figure of the L-dibenzoyl tartaric acid that embodiment 3 obtains;
Fig. 4 is the XRD figure of the L-dibenzoyl tartaric acid that embodiment 4 obtains;
Fig. 5 is the XRD figure of the L-dibenzoyl tartaric acid that embodiment 5 obtains.
Embodiment
Be below specific embodiments of the invention, following embodiment is convenient to understand the present invention better, but does not limit the present invention.
A kind of synthetic method of L-dibenzoyl tartaric acid, with L-TARTARIC ACID (CAS:87-69-4), Benzoyl chloride (CAS:98-88-4) for raw material, copper sulfate (CAS:7758-99-8) is catalyzer, take toluene as solvent, the obtained L-dibenzoyl tartaric acid acid anhydride of reaction, the water gaging such as to add and toluene is hydrolyzed to obtain L-dibenzoyl tartaric acid, wherein solvent toluene, all can reuse with water in hydrolysing step and toluene.
Advantage: 1. various cheaper starting materials is easy to get, safety is easy to operate.
2. good product quality, content >=99%, total recovery >=95%.
Its concrete technical process is:
Be in raw material suction reactor with L-TARTARIC ACID, and a certain amount of solvent toluene is added in reactor, open and stir, copper sulfate is dropped into from dog-house, start to drip Benzoyl chloride, after dropwising, continue reaction 4 hours, be discharged to whizzer, obtain L-dibenzoyl tartaric acid acid anhydride and mother liquor (can be recycled) through rejection filter, L-dibenzoyl tartaric acid acid anhydride is dropped in reactor, add and the water of its equivalent and toluene, be heated to backflow, within about 3 hours, complete, be discharged to whizzer, obtain L-dibenzoyl tartaric acid and mother liquor (can be recycled) through rejection filter.
The detection method of the L-dibenzoyl tartaric acid obtained by this technique is: obtained L-dibenzoyl tartaric acid is loaded enlightening horse c18(2) pillar, with what ammonium acetate of methyl alcohol for moving phase, 254 wavelength, flow velocity 1.0,20ul quantitative loop sample introduction.
Embodiment 1:
A kind of synthetic method of L-dibenzoyl tartaric acid, it comprises the steps: to get L-TARTARIC ACID 150g, toluene 200ml is placed in 1000ml there-necked flask, 1g copper sulfate is added under stirring, start to drip Benzoyl chloride 300g, within 2 hours, drip off, continue reaction 4 hours, be discharged to whizzer, rejection filter obtains L-dibenzoyl tartaric acid acid anhydride 442.5g, by it input 2000ml there-necked flask, add water each 442.5g with toluene, be warming up to backflow, keep 3 hours, be cooled to normal temperature blowing, rejection filter obtains L-dibenzoyl tartaric acid 345.3g
The L-dibenzoyl tartaric acid obtained by the present embodiment carries out TEM test, and as shown in Figure 1, as seen from the figure, finished product L-dibenzoyl tartaric acid purity content is 99.47% to test structure, total recovery 95.4%.
Peak, peak name retention time peak height peak area content
1 2.620 89.998 619.659 0.0166
2 2.812 323.002 1264.886 0.0339
3 4.765 157.245 1160.500 0.0311
4 5.163 66.539 474.181 0.0127
5 5.552 372791.688 3716084.000 99.4684
6 6.760 50.189 556.488 0.0149
7 7.690 1519.759 15104.977 0.4043
8 9.025 42.716 472.100 0.0126
9 13.005 25.251 206.500 0.0055
Embodiment 2:
A synthetic method for L-dibenzoyl tartaric acid, it comprises the steps:
In 10L there-necked flask, drop into L-TARTARIC ACID 1.5kg, toluene 2L, under stirring, add 10g copper sulfate, start to drip Benzoyl chloride 3.5kg, within 2.5 hours, drip off, continue reaction 4 hours, be discharged to whizzer, rejection filter obtains L-dibenzoyl tartaric acid acid anhydride 4.41kg, by it input 20L there-necked flask, add water each 4.41kg with toluene, is warming up to backflow, keeps 3 hours, be cooled to normal temperature blowing, rejection filter obtains L-dibenzoyl tartaric acid 3.49kg.
The L-dibenzoyl tartaric acid obtained by the present embodiment carries out TEM test, and as shown in Figure 2, as seen from the figure, finished product L-dibenzoyl tartaric acid purity content is 99.09% to test structure, total recovery 96.1%.
Peak, peak name retention time peak height peak area content
1 2.598 72.125 340.392 0.0119
2 2.795 336.160 2437.177 0.0849
3 3.005 566.293 6532.359 0.2275
4 3.207 367.988 1677.119 0.0584
5 3.798 52.142 238.124 0.0083
6 3.927 204.440 1781.865 0.0621
7 4.748 172.513 1576.146 0.0549
8 5.123 74.795 524.300 0.0183
9 5.555 287285.656 2811081.750 99.0909
10 7.673 4584.219 45214.801 0.3745
11 11.947 28.792 146.200 0.0051
12 16.315 31.554 96.400 0.0034
Embodiment 3:
A synthetic method for L-dibenzoyl tartaric acid, it comprises the steps:
In 50L reactor, drop into L-TARTARIC ACID 7.5kg, toluene 10L, under stirring, add 40g copper sulfate, start to drip Benzoyl chloride 17kg, within 3.5 hours, drip off, continue reaction 4 hours, be discharged to whizzer, rejection filter obtains L-dibenzoyl tartaric acid acid anhydride 21.4kg, by it input 100L reactor, add water each 21.4kg with toluene, is warming up to backflow, keeps 3 hours, be cooled to normal temperature blowing, rejection filter obtains L-dibenzoyl tartaric acid 17.6kg.
The L-dibenzoyl tartaric acid obtained by the present embodiment carries out TEM test, and as shown in Figure 3, as seen from the figure, finished product L-dibenzoyl tartaric acid purity content is 99.37% to test structure, total recovery 97.2%.
Peak, peak name retention time peak height peak area content
1 2.407 12.545 54.200 0.0004
2 2.815 734.840 4145.950 0.0302
3 3.065 1422.652 14730.800 0.1072
4 3.890 76.667 497.500 0.0036
5 4.090 127.667 798.234 0.0058
6 4.457 63.200 641.762 0.0047
7 4.757 710.114 6827.237 0.0497
8 5.732 968720.750 13657519.000 99.3721
9 8.057 4125.970 42038.398 0.3059
10 8.798 248.558 3782.900 0.0275
11 9.782 33.750 524.900 0.0038
12 10.115 23.667 76.600 0.0006
13 11.265 32.032 375.649 0.0027
14 12.032 17.865 75.729 0.0006
15 12.232 37.690 531.287 0.0039
Embodiment 4:
A synthetic method for L-dibenzoyl tartaric acid, it comprises the steps:
In 500L reactor, drop into L-TARTARIC ACID 75kg, toluene 100L, under stirring, add 350g ferrous sulfate, start to drip Benzoyl chloride 180kg, within 4 hours, drip off, continue reaction 4 hours, be discharged to whizzer, rejection filter obtains L-dibenzoyl tartaric acid acid anhydride 217.3kg, by it input 1000L reactor, add water each 217.3kg with toluene, is warming up to backflow, keeps 3 hours, be cooled to normal temperature blowing, rejection filter obtains L-dibenzoyl tartaric acid 172.6kg.
The L-dibenzoyl tartaric acid obtained by the present embodiment carries out TEM test, and as shown in Figure 4, as seen from the figure, finished product L-dibenzoyl tartaric acid purity content is 99.45% to test structure, total recovery 95.3%.
Peak, peak name retention time peak height peak area content
1 2.807 463.436 2415.439 0.1062
2 3.028 43.076 143.626 0.0063
3 4.800 120.714 782.600 0.0344
4 5.527 225309.078 2261801.250 99.4484
5 6.460 31.625 93.500 0.0041
6 7.587 37.593 174.412 0.0077
7 7.810 827.802 8543.614 0.3757
8 10.615 16.618 62.499 0.0027
9 11.767 22.099 84.650 0.0037
10 18.180 41.315 245.300 0.0108
Embodiment 5:
A synthetic method for L-dibenzoyl tartaric acid, it comprises the steps:
In 3000L reactor, drop into L-TARTARIC ACID 450kg, toluene 600L, under stirring, add 2kg copper sulfate, start to drip Benzoyl chloride 880kg, within 5 hours, drip off, continue reaction 4 hours, be discharged to whizzer, rejection filter obtains L-dibenzoyl tartaric acid acid anhydride 1211.7kg, by it input 5000L reactor, add water each 1211.7kg with toluene, is warming up to backflow, keeps 3 hours, be cooled to normal temperature blowing, rejection filter obtains L-dibenzoyl tartaric acid 1059.8kg.
The L-dibenzoyl tartaric acid obtained by the present embodiment carries out TEM test, and as shown in Figure 5, as seen from the figure, finished product L-dibenzoyl tartaric acid purity content is 99.09% to test structure, total recovery 97.2%.
Peak, peak name retention time peak height peak area content
1 0.830 30.741 120.950 0.0021
2 2.682 462.114 2494.700 0.0433
3 2.920 219.772 2372.250 0.0412
4 4.583 393.141 3235.900 0.0562
5 5.672 493603.000 5650332.000 99.0904
6 7.950 8330.513 88294.805 0.5328
7 8.687 109.326 1328.450 0.0231
8 9.372 24.668 218.750 0.0038
9 10.373 50.176 736.769 0.0128
10 10.835 87.896 2317.862 0.0402
11 11.528 77.977 1789.997 0.0311
12 12.130 63.223 536.157 0.0093
13 14.083 84.235 2098.178 0.0364
14 16.287 38.457 398.955 0.0069
15 17.222 41.859 707.450 0.0123
16 18.078 82.727 3350.800 0.0582 。
Claims (6)
1. a synthetic method for L-dibenzoyl tartaric acid, is characterized in that, synthesis step is:
(1) 1 part of L-TARTARIC ACID, is got by weight and appropriate organic solvent puts into reactor, under agitation, in reactor, add 0.1-0.001 part catalyzer, afterwards, in reactor, add 1 ~ 3 part of Benzoyl chloride with the drop rate of 1-10mL/min, after dropwising, continue reaction 4h, then, the mixture be obtained by reacting is turned to be incorporated in whizzer and carries out centrifugation, obtain solid L-dibenzoyl tartaric acid acid anhydride, for subsequent use;
Described catalyzer is copper sulfate or ferrous sulfate;
(2), the L-dibenzoyl tartaric acid acid anhydride that step (1) is obtained is put into reactor, and toluene and the water of weight such as to add wherein, reflux 2-4h under 100 DEG C of conditions, afterwards, be cooled to normal temperature, the mixture transposition obtained is carried out centrifugation in whizzer, obtains solid L-dibenzoyl tartaric acid.
2. the synthetic method of a kind of L-dibenzoyl tartaric acid according to claim 1, is characterized in that: in step (1) and step (2), the rotating speed of centrifugation is 100-1000 r/min.
3. the synthetic method of a kind of L-dibenzoyl tartaric acid according to claim 1, is characterized in that: the solvent in described step (1) is toluene.
4. the synthetic method of a kind of L-dibenzoyl tartaric acid according to claim 3, it is characterized in that: in described step (1), the add-on of toluene and the ratio of L-TARTARIC ACID are 1L/0.75kg.
5. the synthetic method of a kind of L-dibenzoyl tartaric acid according to claim 1, is characterized in that: the rate of temperature fall in described step (2) is 5-10 DEG C/min.
6. the synthetic method of a kind of L-dibenzoyl tartaric acid according to claim 1, is characterized in that: the stirring velocity in described step (1) is 500-3000r/min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410836840.1A CN104496806B (en) | 2014-12-30 | 2014-12-30 | A kind of synthetic method of L-dibenzoyl tartaric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410836840.1A CN104496806B (en) | 2014-12-30 | 2014-12-30 | A kind of synthetic method of L-dibenzoyl tartaric acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104496806A true CN104496806A (en) | 2015-04-08 |
| CN104496806B CN104496806B (en) | 2016-07-06 |
Family
ID=52938281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410836840.1A Active CN104496806B (en) | 2014-12-30 | 2014-12-30 | A kind of synthetic method of L-dibenzoyl tartaric acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104496806B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108802273A (en) * | 2018-05-29 | 2018-11-13 | 濮阳天健生物科技有限公司 | A kind of L-（-）The detection method of dibenzoyl tartaric acid |
| CN109400468A (en) * | 2018-10-30 | 2019-03-01 | 濮阳天健生物科技有限公司 | A kind of preparation method of L- dibenzoyl tartaric acid dimethyl ester |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003335766A (en) * | 2002-05-20 | 2003-11-28 | Nippon Light Metal Co Ltd | Method for producing dibenzoyltartaric acid and acid anhydride thereof |
| CN1900053A (en) * | 2006-07-21 | 2007-01-24 | 张家港市华昌药业有限公司 | Process for preparing D-alpha-amino isovaleric acid |
| CN101239913A (en) * | 2008-03-17 | 2008-08-13 | 广州辉宏生物医药科技有限公司 | Chiral tartaric acids derivatives and preparation method thereof |
| CN103319308A (en) * | 2013-07-08 | 2013-09-25 | 濮阳天健生物科技有限公司 | Synthesis method of 8(Z/E)-dodecylene-1-alcohol |
-
2014
- 2014-12-30 CN CN201410836840.1A patent/CN104496806B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003335766A (en) * | 2002-05-20 | 2003-11-28 | Nippon Light Metal Co Ltd | Method for producing dibenzoyltartaric acid and acid anhydride thereof |
| CN1900053A (en) * | 2006-07-21 | 2007-01-24 | 张家港市华昌药业有限公司 | Process for preparing D-alpha-amino isovaleric acid |
| CN101239913A (en) * | 2008-03-17 | 2008-08-13 | 广州辉宏生物医药科技有限公司 | Chiral tartaric acids derivatives and preparation method thereof |
| CN103319308A (en) * | 2013-07-08 | 2013-09-25 | 濮阳天健生物科技有限公司 | Synthesis method of 8(Z/E)-dodecylene-1-alcohol |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108802273A (en) * | 2018-05-29 | 2018-11-13 | 濮阳天健生物科技有限公司 | A kind of L-（-）The detection method of dibenzoyl tartaric acid |
| CN109400468A (en) * | 2018-10-30 | 2019-03-01 | 濮阳天健生物科技有限公司 | A kind of preparation method of L- dibenzoyl tartaric acid dimethyl ester |
| CN109400468B (en) * | 2018-10-30 | 2021-09-07 | 濮阳天健生物科技有限公司 | Preparation method of L-dibenzoyl dimethyl tartrate |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104496806B (en) | 2016-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104529779A (en) | Synthesis method of D-dibenzoyl tartaric acid | |
| CN109500059B (en) | Transformation and microcapsule curing stabilization method for arsenic sulfide slag | |
| CN103397209B (en) | Method for extracting vanadium from high-calcium and high-phosphorus vanadium slag | |
| CN104496806A (en) | Synthetic method of L-dibenzoyl tartaric acid | |
| CN101735023B (en) | Method for preparing 3-bromo-5-chlorophenol | |
| CN104447338B (en) | A kind of D-is to the tartaric synthetic method of methyldiphenyl formyl | |
| CN103880694A (en) | Preparation method of 2-hydroxy-5-aminobenzoic acid | |
| CN104151198A (en) | Synthetic method for N-nitrosobis(cyanomethyl)amino | |
| CN109851619B (en) | Riboflavin purification process | |
| CN106046077A (en) | Tulathromycin A synthesis method | |
| CN103952534B (en) | A kind of method utilizing nickel-molybdenum ore to prepare Sodium orthomolybdate | |
| CN107200758B (en) | Preparation method of high-purity clindamycin and clindamycin salt | |
| CN107200691B (en) | Preparation method of substituted p-phenylenediamine hydrochloride | |
| CN104370830A (en) | Synthetic method of 5-trifluoromethyl uracil | |
| CN105061232A (en) | Preparation method for red base B | |
| CN104529776A (en) | Synthesis method of L-p-methyl dibenzoyl tartaric acid | |
| CN104402813B (en) | Novel method for synthesizing sorafenib | |
| CN102250173A (en) | Preparation methods of 6-O-methylerythromycin A derivative and clarithromycin | |
| CN102391170B (en) | A kind of preparation method of N, N-diallyl-5-methoxytryptamine hydrochlorides | |
| CN115650870B (en) | Method for preparing high-purity pentetic acid and application thereof | |
| CN108568306B (en) | Preparation method and application of basic copper-zinc carbonate double salt | |
| CN103397187B (en) | Method for vanadium extraction by activating high-calcium high-phosphorus vanadium slag with nitric acid | |
| CN102502777A (en) | Method for preparing silver nitrate with various types of silver-ion-containing waste water as raw materials | |
| CN103396347B (en) | Method for synthesizing p-hydroxyl thiobenzamide | |
| CN102503753A (en) | Method for synthesizing 2-amino five-membered heterocyclic derivative |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Synthetic method of L-dibenzoyl tartaric acid Effective date of registration: 20180802 Granted publication date: 20160706 Pledgee: Bank of China Limited by Share Ltd. Puyang branch Pledgor: PUYANG TIANJIAN BIOTECHNOLOGY Co.,Ltd. Registration number: 2018990000643 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20210112 Granted publication date: 20160706 Pledgee: Bank of China Limited by Share Ltd. Puyang branch Pledgor: PUYANG TIANJIAN BIOTECHNOLOGY Co.,Ltd. Registration number: 2018990000643 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A synthetic method of l-dibenzoyl tartaric acid Effective date of registration: 20210325 Granted publication date: 20160706 Pledgee: Bank of China Limited by Share Ltd. Puyang branch Pledgor: PUYANG TIANJIAN BIOTECHNOLOGY Co.,Ltd. Registration number: Y2021980002101 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20220519 Granted publication date: 20160706 Pledgee: Bank of China Limited by Share Ltd. Puyang branch Pledgor: PUYANG TIANJIAN BIOTECHNOLOGY Co.,Ltd. Registration number: Y2021980002101 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20240410 Address after: 457000 Economic and Technological Industrial Agglomeration Area in Puyang City, Henan Province Patentee after: TIANCHI PHARMACEUTICAL Co.,Ltd. Country or region after: China Address before: 457000 Economic and Technological Industrial Agglomeration Area in Puyang City, Henan Province Patentee before: PUYANG TIANJIAN BIOTECHNOLOGY Co.,Ltd. Country or region before: China |