CN104496806B - A kind of synthetic method of L-dibenzoyl tartaric acid - Google Patents
A kind of synthetic method of L-dibenzoyl tartaric acid Download PDFInfo
- Publication number
- CN104496806B CN104496806B CN201410836840.1A CN201410836840A CN104496806B CN 104496806 B CN104496806 B CN 104496806B CN 201410836840 A CN201410836840 A CN 201410836840A CN 104496806 B CN104496806 B CN 104496806B
- Authority
- CN
- China
- Prior art keywords
- tartaric acid
- dibenzoyl tartaric
- toluene
- synthetic method
- 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.)
- Active
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 48
- 238000010189 synthetic method Methods 0.000 title claims abstract description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 81
- -1 L-dibenzoyl tartaric acid acid anhydride Chemical class 0.000 claims abstract description 17
- 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 14
- 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 13
- 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
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000011790 ferrous sulphate Substances 0.000 claims description 4
- 235000003891 ferrous sulphate Nutrition 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
- 238000013019 agitation Methods 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000002156 mixing 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 21
- 238000011084 recovery Methods 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 8
- 238000000926 separation method Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- 238000007664 blowing Methods 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000010413 mother solution Substances 0.000 description 2
- 239000003960 organic solvent 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
- 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
- 239000007795 chemical reaction product Substances 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
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000000843 powder Substances 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
- 239000000126 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A kind of synthetic method of L-dibenzoyl tartaric acid, with L-TARTARIC ACID, Benzenecarbonyl chloride. for raw material, copper sulfate is catalyst, with toluene for solvent, reaction prepares L-dibenzoyl tartaric acid acid anhydride, add equivalent water and toluene and be hydrolyzed to obtain L-dibenzoyl tartaric acid, wherein water and all repeatable utilization of toluene in solvent toluene and hydrolysing step.The method technique of the present invention is simple, safety easily operation, and process recovery ratio reaches more than 95%, and meanwhile, cost of material is relatively low, and part material is recyclable, and finished product product purity is higher, has the chiral separation performance of excellence.
Description
Technical field
The present invention relates to the chemical synthesis process technical field of a kind of chiral selectors, specifically the synthetic method of a kind of L-dibenzoyl tartaric acid.
Background technology
L-dibenzoyl tartaric acid is a kind of white crystalline powder, and odorless, mildly bitter flavor are slightly soluble in water, and pH value is 3-4, is acidity, dissolves in ethanol and acetone and other organic solvent.It is widely used in chiral separation racemic amines compounds.And because it is cheap, stable in properties, and it is easily recycled and there is good industrial application value.Its molecular formula is as follows:
Common synthetic method has the disadvantage that: 1. raw material has strong and stimulating, severe corrosive, severe toxicity, not easily operates.2. raw material availability is low, it is impossible to recycle, and produces pollution bigger.3. process recovery ratio is low, and about 50%, product purity is relatively low, and production cost is higher.
Summary of the invention
The technical problem to be solved is in that to provide the synthetic method of a kind of L-dibenzoyl tartaric acid, the method technique is simple, safety easily operation, process recovery ratio reaches more than 95%, simultaneously, cost of material is relatively low, and part material is recyclable, finished product product purity is higher, has the chiral separation performance of excellence.
The synthetic method of L-dibenzoyl tartaric acid is: first with L-TARTARIC ACID (CAS:87-69-4), Benzenecarbonyl chloride. (CAS:98-88-4) and thionyl chloride (CAS:7719-09-7) for raw material, with toluene for solvent, reaction prepares L-dibenzoyl tartaric acid acid anhydride, then adds water L-dibenzoyl tartaric acid acid anhydride through being hydrolyzed to obtain L-dibenzoyl tartaric acid.The reaction mechanism mechanism of reaction 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 present invention particularly provides is: the synthetic method of a kind of L-dibenzoyl tartaric acid, and synthesis step is:
(1), take 1 part of L-TARTARIC ACID by weight and appropriate organic solvent is put in reactor, under agitation, in reactor, add 0.1-0.001 part catalyst, afterwards, in reactor, add 1 ~ 3 part of Benzenecarbonyl chloride. with the drop rate of 1-10mL/min, after dropwising, continue reaction 4h, then, the mixture being obtained by reacting is turned and is incorporated in centrifuge and is centrifuged separation, obtain solid L-dibenzoyl tartaric acid acid anhydride, standby；
Described catalyst is copper sulfate or ferrous sulfate；
(2), the L-dibenzoyl tartaric acid acid anhydride that step (1) prepares is put in reactor, and toluene and the water of weight such as it is added thereto to, it is heated to reflux 2-4h under 100 DEG C of conditions, afterwards, it is cooled to room temperature, it is centrifuged the mixture transposition obtained separating in centrifuge, obtains solid L-dibenzoyl tartaric acid.
In step (1) and step (2), the rotating speed of centrifugation is 100-1000r/min.
Solvent in described step (1) is toluene.
In described step (1), the addition 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.
Mixing speed in described step (1) is 500-3000r/min.
Above method of the present invention having the beneficial effect that compared with the method adopting thionyl chloride to be raw material
1, the method technique of this synthesis L-dibenzoyl tartaric acid is simple, manipulation is convenient, mild condition, it is to avoid the application of noxious substance thionyl chloride, improves the safe operability of technique；As the addition of the copper sulfate of catalyst or ferrous sulfate, substantially reduce the response time of technique, improve product yield and the product quality of technique；Meanwhile, low raw-material cost used, the recycling capable of circulation such as solvent used in process, reduce production cost, decrease environmental pollution, be conducive to large-scale production.
2, the L-dibenzoyl tartaric acid end product quality purity of the method synthesis reaches more than 99%, and technique product yield reaches more than 95%, has the chiral separation performance of excellence.
Accompanying drawing explanation
Fig. 1 is the XRD figure of the L-dibenzoyl tartaric acid that embodiment 1 prepares；
Fig. 2 is the XRD figure of the L-dibenzoyl tartaric acid that embodiment 2 prepares；
Fig. 3 is the XRD figure of the L-dibenzoyl tartaric acid that embodiment 3 prepares；
Fig. 4 is the XRD figure of the L-dibenzoyl tartaric acid that embodiment 4 prepares；
Fig. 5 is the XRD figure of the L-dibenzoyl tartaric acid that embodiment 5 prepares.
Detailed description of the invention
The following is specific embodiments of the invention, below example is easy to be more fully understood that the present invention, 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), Benzenecarbonyl chloride. (CAS:98-88-4) for raw material, copper sulfate (CAS:7758-99-8) is catalyst, with toluene for solvent, reaction prepares L-dibenzoyl tartaric acid acid anhydride, add equivalent water and toluene and be hydrolyzed to obtain L-dibenzoyl tartaric acid, wherein water and all repeatable utilization of toluene in solvent toluene and hydrolysing step.
Advantage: 1. various cheaper starting materials are easy to get, safety is operation easily.
2. good product quality, content >=99%, total recovery >=95%.
Its concrete technological process is:
With L-TARTARIC ACID for raw material suction reactor, and in reactor, add a certain amount of solvent toluene, open stirring, copper sulfate is put into from dog-house, start to drip Benzenecarbonyl chloride., after dropwising, continue reaction 4 hours, be discharged to centrifuge, obtain L-dibenzoyl tartaric acid acid anhydride and mother solution (can be recycled) through rejection filter, L-dibenzoyl tartaric acid acid anhydride is put in reactor, adding the water with its equivalent and toluene, heating, to backflow, completes for about 3 hours, it is discharged to centrifuge, obtains L-dibenzoyl tartaric acid and mother solution (can be recycled) through rejection filter.
The detection method of the L-dibenzoyl tartaric acid obtained by this technique is: prepared L-dibenzoyl tartaric acid is loaded enlightening horse c18(2) pillar, with what ammonium acetate of methanol for mobile 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 take L-TARTARIC ACID 150g, toluene 200ml is placed in 1000ml there-necked flask, stirring is lower adds 1g copper sulfate, start to drip Benzenecarbonyl chloride. 300g, within 2 hours, drip off, continue reaction 4 hours, being discharged to centrifuge, rejection filter obtains L-dibenzoyl tartaric acid acid anhydride 442.5g, by input 2000ml there-necked flask, add water 442.5g each with toluene, it is warming up to backflow, keeps 3 hours, be cooled to room 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, as it is 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
12.62089.998619.6590.0166
22.812323.0021264.8860.0339
34.765157.2451160.5000.0311
45.16366.539474.1810.0127
55.552372791.6883716084.00099.4684
66.76050.189556.4880.0149
77.6901519.75915104.9770.4043
89.02542.716472.1000.0126
913.00525.251206.5000.0055
Embodiment 2:
The synthetic method of a kind of L-dibenzoyl tartaric acid, it comprises the steps:
Putting into L-TARTARIC ACID 1.5kg, toluene 2L in 10L there-necked flask, stirring is lower adds 10g copper sulfate, starts to drip Benzenecarbonyl chloride. 3.5kg, within 2.5 hours, drip off, continuing reaction 4 hours, be discharged to centrifuge, rejection filter obtains L-dibenzoyl tartaric acid acid anhydride 4.41kg, by input 20L there-necked flask, add water 4.41kg each with toluene, is warming up to backflow, keeps 3 hours, being cooled to room 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, as in figure 2 it is shown, 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
12.59872.125340.3920.0119
22.795336.1602437.1770.0849
33.005566.2936532.3590.2275
43.207367.9881677.1190.0584
53.79852.142238.1240.0083
63.927204.4401781.8650.0621
74.748172.5131576.1460.0549
85.12374.795524.3000.0183
95.555287285.6562811081.75099.0909
107.6734584.21945214.8010.3745
1111.94728.792146.2000.0051
1216.31531.55496.4000.0034
Embodiment 3:
The synthetic method of a kind of L-dibenzoyl tartaric acid, it comprises the steps:
Putting into L-TARTARIC ACID 7.5kg, toluene 10L in 50L reactor, stirring is lower adds 40g copper sulfate, starts to drip Benzenecarbonyl chloride. 17kg, within 3.5 hours, drip off, continuing reaction 4 hours, be discharged to centrifuge, rejection filter obtains L-dibenzoyl tartaric acid acid anhydride 21.4kg, by input 100L reactor, add water 21.4kg each with toluene, is warming up to backflow, keeps 3 hours, being cooled to room 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, as it is shown on 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
12.40712.54554.2000.0004
22.815734.8404145.9500.0302
33.0651422.65214730.8000.1072
43.89076.667497.5000.0036
54.090127.667798.2340.0058
64.45763.200641.7620.0047
74.757710.1146827.2370.0497
85.732968720.75013657519.00099.3721
98.0574125.97042038.3980.3059
108.798248.5583782.9000.0275
119.78233.750524.9000.0038
1210.11523.66776.6000.0006
1311.26532.032375.6490.0027
1412.03217.86575.7290.0006
1512.23237.690531.2870.0039
Embodiment 4:
The synthetic method of a kind of L-dibenzoyl tartaric acid, it comprises the steps:
Putting into L-TARTARIC ACID 75kg, toluene 100L in 500L reactor, stirring is lower adds 350g ferrous sulfate, starts to drip Benzenecarbonyl chloride. 180kg, within 4 hours, drip off, continuing reaction 4 hours, be discharged to centrifuge, rejection filter obtains L-dibenzoyl tartaric acid acid anhydride 217.3kg, by input 1000L reactor, add water 217.3kg each with toluene, is warming up to backflow, keeps 3 hours, being cooled to room 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
12.807463.4362415.4390.1062
23.02843.076143.6260.0063
34.800120.714782.6000.0344
45.527225309.0782261801.25099.4484
56.46031.62593.5000.0041
67.58737.593174.4120.0077
77.810827.8028543.6140.3757
810.61516.61862.4990.0027
911.76722.09984.6500.0037
1018.18041.315245.3000.0108
Embodiment 5:
The synthetic method of a kind of L-dibenzoyl tartaric acid, it comprises the steps:
Putting into L-TARTARIC ACID 450kg, toluene 600L in 3000L reactor, stirring is lower adds 2kg copper sulfate, starts to drip Benzenecarbonyl chloride. 880kg, within 5 hours, drip off, continuing reaction 4 hours, be discharged to centrifuge, rejection filter obtains L-dibenzoyl tartaric acid acid anhydride 1211.7kg, by input 5000L reactor, add water 1211.7kg each with toluene, is warming up to backflow, keeps 3 hours, being cooled to room 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, as it is 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
10.83030.741120.9500.0021
22.682462.1142494.7000.0433
32.920219.7722372.2500.0412
44.583393.1413235.9000.0562
55.672493603.0005650332.00099.0904
67.9508330.51388294.8050.5328
78.687109.3261328.4500.0231
89.37224.668218.7500.0038
910.37350.176736.7690.0128
1010.83587.8962317.8620.0402
1111.52877.9771789.9970.0311
1212.13063.223536.1570.0093
1314.08384.2352098.1780.0364
1416.28738.457398.9550.0069
1517.22241.859707.4500.0123
1618.07882.7273350.8000.0582。
Claims (4)
1. the synthetic method of a L-dibenzoyl tartaric acid, it is characterised in that synthesis step is:
(1), take 1 part of L-TARTARIC ACID by weight and q. s. toluene is put in reactor, the addition of toluene and the tartaric ratio of D-are 1L/0.75kg, under agitation, add 0.1-0.001 part catalyst in reactor, afterwards, in reactor, add 1 ~ 3 part of Benzenecarbonyl chloride. with the drop rate of 1-10mL/min, after dropwising, continue reaction 4h, then, the mixture being obtained by reacting is turned and is incorporated in centrifuge and is centrifuged separating, obtains solid L-dibenzoyl tartaric acid acid anhydride, standby；
Described catalyst is copper sulfate or ferrous sulfate；
(2), the L-dibenzoyl tartaric acid acid anhydride that step (1) prepares is put in reactor, and toluene and the water of weight such as it is added thereto to, it is heated to reflux 2-4h under 100 DEG C of conditions, afterwards, it is cooled to room temperature, it is centrifuged the mixture transposition obtained separating in centrifuge, obtains solid L-dibenzoyl tartaric acid.
2. the synthetic method of a kind of L-dibenzoyl tartaric acid according to claim 1, it is characterised in that: step (1) and in step (2), the rotating speed of centrifugation is 100-1000r/min.
3. the synthetic method of a kind of L-dibenzoyl tartaric acid according to claim 1, it is characterised in that: the rate of temperature fall in described step (2) is 5-10 DEG C/min.
4. the synthetic method of a kind of L-dibenzoyl tartaric acid according to claim 1, it is characterised in that: the mixing speed 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 CN104496806A (en) | 2015-04-08 |
| CN104496806B true 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) |
Families Citing this family (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 |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4301766B2 (en) * | 2002-05-20 | 2009-07-22 | 日本軽金属株式会社 | Method for producing dibenzoyltartaric acid and acid anhydrides 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 |
| CN101239913B (en) * | 2008-03-17 | 2011-03-16 | 广州辉宏生物医药科技有限公司 | Chiral tartaric acids derivatives preparation method |
| CN103319308B (en) * | 2013-07-08 | 2015-05-06 | 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
Also Published As
| Publication number | Publication date |
|---|---|
| CN104496806A (en) | 2015-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104496806B (en) | A kind of synthetic method of L-dibenzoyl tartaric acid | |
| CN104529779A (en) | Synthesis method of D-dibenzoyl tartaric acid | |
| CN102304074A (en) | Method for preparing rubber peptizing agent, namely 2,2'-dibenzamido diphenyl disulfide compound | |
| CN101735023B (en) | Method for preparing 3-bromo-5-chlorophenol | |
| CN101519411B (en) | Method for preparing phenylboronic acid-2-methyl formate | |
| CN107652294A (en) | A kind of preparation method of Ibrutinib | |
| CN103657732B (en) | Preparation method of SO4<2->/TiO2-ZnO mixed crystal solid acid carrier coordination catalyst | |
| CN104447338B (en) | A kind of D-is to the tartaric synthetic method of methyldiphenyl formyl | |
| CN104370830B (en) | A kind of synthetic method of 5-trifluoromethyl uracil | |
| CN105061232A (en) | Preparation method for red base B | |
| CN106831549A (en) | A kind of method of asymmetric synthesis of Claritin carbinoxamine | |
| CN104151170A (en) | 4-nitrophenethylamine hydrochloride and preparation method thereof | |
| CN103073499A (en) | Method for preparing rhenium ion liquid by extraction method | |
| CN107573301B (en) | Preparation method of tricyclazole intermediate | |
| CN104529776A (en) | Synthesis method of L-p-methyl dibenzoyl tartaric acid | |
| CN108623462A (en) | A kind of new preparation process of 4- hydroxy-betas-nitrostyrolene | |
| CN104496892A (en) | Novel technology for synthesizing 4-dimethylamino-pyridine | |
| CN110746313B (en) | Method for splitting 4-nitro-phenylalanine enantiomer | |
| CN104447345B (en) | The treatment process of Yi Zhong Evil humulone etherificate waste salt dregs recycling | |
| CN110015960A (en) | The preparation method and application of 1,3- bis- (4,4- methyl formate phenyl) acetone | |
| CN109438278A (en) | A kind of occrycetin preparation method | |
| CN108568306B (en) | Preparation method and application of basic copper-zinc carbonate double salt | |
| CN102584720B (en) | Preparation technology o high-purity gefitinib | |
| CN102503753A (en) | Method for synthesizing 2-amino five-membered heterocyclic derivative | |
| CN104370807B (en) | The synthetic method of a kind of 6-hydroxyl-5-nitronicotinic acid and process for separation and purification thereof |
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 | ||
| 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 |
|
| 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: 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 |
|
| PC01 | Cancellation 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 |
|
| TR01 | Transfer 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 |