CN116554045A - Method for preparing 6-aminocaproic acid by cyclohexanone one-step synthesis - Google Patents
Method for preparing 6-aminocaproic acid by cyclohexanone one-step synthesis Download PDFInfo
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- CN116554045A CN116554045A CN202310496729.1A CN202310496729A CN116554045A CN 116554045 A CN116554045 A CN 116554045A CN 202310496729 A CN202310496729 A CN 202310496729A CN 116554045 A CN116554045 A CN 116554045A
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- Prior art keywords
- reaction
- cyclohexanone
- aminocaproic acid
- hydroxylamine
- stirring
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 60
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 229960002684 aminocaproic acid Drugs 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 59
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 238000007789 sealing Methods 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 230000007246 mechanism Effects 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 13
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108010073385 Fibrin Proteins 0.000 description 3
- 102000009123 Fibrin Human genes 0.000 description 3
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229950003499 fibrin Drugs 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 108010088842 Fibrinolysin Proteins 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 102000013566 Plasminogen Human genes 0.000 description 2
- 108010051456 Plasminogen Proteins 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000002439 hemostatic effect Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229940012957 plasmin Drugs 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- AENOKLOQCCSDAZ-UHFFFAOYSA-N 6-aminohexanoic acid;hydrochloride Chemical compound Cl.NCCCCCC(O)=O AENOKLOQCCSDAZ-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 108010058861 Fibrin Fibrinogen Degradation Products Proteins 0.000 description 1
- 108010049003 Fibrinogen Proteins 0.000 description 1
- 102000008946 Fibrinogen Human genes 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- -1 and then the 1 Chemical compound 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000000504 antifibrinolytic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000208 fibrin degradation product Substances 0.000 description 1
- 229940012952 fibrinogen Drugs 0.000 description 1
- 230000020764 fibrinolysis Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/12—Formation of amino and carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
-
- 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
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
The invention belongs to the field of medicine synthesis, and in particular relates to a method for preparing 6-aminocaproic acid by one-step synthesis of cyclohexanone, which takes cyclohexanone and hydroxylamine with rich sources as raw materials to obtain the 6-aminocaproic acid through one-step ring-opening reaction, and the reaction process is simple and the post-treatment is convenient; the cyclohexanone is excessively added, and in the reaction process, the cyclohexanone serves as a reaction raw material and a reaction reagent, so that the forward reaction can be ensured, and the conversion rate is improved; the preparation method has mild reaction conditions, the yield of the prepared 6-aminocaproic acid can reach more than 85 percent, the purity can reach more than 97 percent, and the preparation method is suitable for large-scale production.
Description
Technical Field
The invention belongs to the technical field of medicine synthesis, and particularly relates to a method for preparing 6-aminocaproic acid by cyclohexanone through one-step synthesis.
Background
6-aminocaproic acid is an antifibrinolytic agent. Fibrinogen binds specifically to fibrin through lysine binding sites in its molecular structure and then becomes plasmin under the action of an activator, which cleaves arginine and lysine peptide chains in fibrin to form fibrin degradation products, which solubilizes blood clots. The 6-aminocaproic acid can inhibit the combination of the plasminogen and the fibrin, and prevent the plasminogen from being activated, thereby inhibiting the fibrinolysis, and directly inhibiting the plasmin activity at high concentration, thereby achieving the hemostatic effect.
The 6-aminocaproic acid is generally obtained by hydrolysis and refining of caprolactam or its polymer by direct chemical synthesis. As disclosed in US patent document, publication No. US2453234a, the hydrolysis temperature is up to 250 ℃, and acetic acid is added as a hydrolysis catalyst, the hydrolysis temperature is too high, which is unfavorable for energy saving and consumption reduction, and the safety is low, so that the industrialized popularization is limited.
And as the Chinese patent application, publication No. CN 101125821A, a process for preparing 6-aminocaproic acid as hemostatic is disclosed, which includes dissolving caprolactam in diluted hydrochloric acid, heating for reflux to obtain 6-aminocaproic acid hydrochloride, neutralizing with spherical macroporous styrene weak-base anion exchange resin, and post-treating. The technical proposal of the application is that caprolactam is heated and hydrolyzed in hydrochloric acid aqueous solution to prepare 6-aminocaproic acid, the reaction process is more intense, and meanwhile, the caprolactam is neutralized by ion exchange resin. Because of the limitation of resin exchange amount, the ion exchange resin is excessively large in the industrial application process, the cost and the expense are very high, the reaction time is long, the product yield is low, and the product yield is generally about 80 percent; in addition, the ion exchange resin needs to be regenerated after neutralization, a large amount of salt-containing wastewater can be generated in the regeneration process, the environmental pollution is large, and meanwhile, the cost of wastewater treatment is increased, so that the method is not beneficial to industrial popularization and application.
Disclosure of Invention
In order to overcome the technical problems, the invention provides a method for preparing 6-aminocaproic acid by one-step synthesis of cyclohexanone, which has the advantages of easily obtained raw materials and mild reaction conditions, and the yield of the prepared 6-aminocaproic acid can reach more than 85 percent, the purity can reach more than 97 percent, and the method is suitable for large-scale production.
The technical scheme for solving the technical problems is as follows:
a method for preparing 6-aminocaproic acid by one-step synthesis of cyclohexanone, which takes cyclohexanone and hydroxylamine as raw materials, and obtains the 6-aminocaproic acid through one-step ring-opening reaction;
the synthetic route is as follows:
the method comprises the following steps: the cyclohexanone and hydroxylamine undergo condensation reaction to obtain cyclohexanone oxime, then the cyclohexanone oxime is rearranged in sulfuric acid to obtain 1, 6-caprolactam, and then the 1, 6-aminocaproic acid is obtained by ring opening in fuming sulfuric acid;
the reaction mechanism is as follows:
the method comprises the following steps:
mixing cyclohexanone and hydroxylamine according to a molar ratio of 1:2-3, adding 2/3 cyclohexanone and hydroxylamine into a stirring reaction vessel with a heating device, and controlling the reaction temperature to be 150-155 ℃; sealing a tube, stirring for reaction for at least 1h, naturally cooling to below 60 ℃, adding the rest cyclohexanone, slowly adding water and concentrated sulfuric acid into a reaction container when the temperature of the reaction material is below 40 ℃, then raising the temperature to 110-115 ℃, stirring for reaction for at least 10min, transferring all the materials in the reaction container into water, uniformly stirring, collecting solids, adding fuming sulfuric acid, heating to 100 ℃, sealing a tube, stirring for reaction for at least 30min, performing centrifugal separation after the reaction is completed, obtaining a crude 6-aminocaproic acid product, and recrystallizing with ethanol for at least two times to obtain a pure 6-aminocaproic acid product.
Further, the molar volume ratio of the hydroxylamine to the water is 1 mol:6-8 mL.
Further, the molar weight ratio of the hydroxylamine to the concentrated sulfuric acid is 1 mol:200-230 g.
Further, the molar weight ratio of the hydroxylamine to the fuming sulfuric acid is 1 mol:160-180 g.
The beneficial effects of the invention are as follows:
the synthesis method takes cyclohexanone and hydroxylamine which are rich in sources as raw materials, and the 6-aminocaproic acid is obtained through one-step ring-opening reaction, and the reaction process is simple and the post-treatment is convenient; the cyclohexanone is excessively added, and in the reaction process, the cyclohexanone serves as a reaction raw material and a reaction reagent, so that the forward reaction can be ensured, and the conversion rate is improved; the preparation method has mild reaction conditions, the yield of the prepared 6-aminocaproic acid can reach more than 85 percent, the purity can reach more than 97 percent, and the preparation method is suitable for large-scale production.
Drawings
The invention will be described in further detail with reference to the drawings and the detailed description.
FIG. 1 is a nuclear magnetic resonance spectrum of a pure 6-aminocaproic acid product obtained in example 1 of the invention;
FIG. 2 is a nuclear magnetic resonance spectrum of a pure 6-aminocaproic acid product obtained in example 1 of the invention.
Detailed Description
Reagents and raw materials used in the synthetic steps of the invention are commercially available.
Example 1:
196g of cyclohexanone (2 mol) and 33g of hydroxylamine (1 mol) are mixed and added into a stirring reaction vessel with a heating device, and the reaction temperature is controlled to be 155 ℃; after tube sealing and stirring reaction for 1h, naturally cooling to below 60 ℃, adding 98g of cyclohexanone (1 mol), slowly adding 6mL of water and 200g of concentrated sulfuric acid into a reaction container when the temperature of the reaction material is below 40 ℃, then raising the temperature to 110 ℃, stirring and reacting for 10min, completely transferring the materials in the reaction container into water for facilitating product precipitation, uniformly stirring, collecting solids, adding 180g of fuming sulfuric acid, heating to 100 ℃, tube sealing and stirring for 30min, centrifuging after the reaction is completed, obtaining a crude 6-aminocaproic acid product, recrystallizing with ethanol at least twice to obtain a pure 6-aminocaproic acid product, and obtaining the yield of 89.9%.
The nuclear magnetic spectrum data of the pure 6-aminocaproic acid prepared in this example are as follows:
melting point is 207-208 ℃; MS (m/z): [ M+H ]] + ：132。
1 H NMR(300MHz，H 2 O)δ：2.82(t，J＝6.0Hz，2H)，2.03(t，J＝6.0Hz，2H)，1.65-1.18(m，6H)；
13 C NMR(75MHz，H 2 O)δ：183.53，39.24，37.13，26.36，25.32，25.10；
The purity was 97.8% by HPLC.
Example 2:
128g of cyclohexanone (1.3 mol) and 33g of hydroxylamine (1 mol) are taken and added into a stirring reaction vessel with a heating device, and the reaction temperature is controlled to be 150 ℃; after the reaction is carried out for 1.5 hours by tube sealing and stirring, the temperature is naturally reduced to below 60 ℃, 68g of cyclohexanone (0.7 mol) is added, when the temperature of the reaction material is below 40 ℃, 8mL of water and 230g of concentrated sulfuric acid are slowly added into a reaction container, then the temperature is raised to 115 ℃, after the reaction is carried out for 15 minutes by stirring, the materials in the reaction container are completely transferred into water for facilitating the precipitation of the product, after the uniform stirring, the solid is collected, 160g of fuming sulfuric acid is added, the reaction is carried out by tube sealing and stirring for 45 minutes by heating to 100 ℃, centrifugal separation is carried out after the reaction, the crude 6-aminocaproic acid is obtained, the pure 6-aminocaproic acid is obtained by recrystallisation by ethanol for at least two times, and the yield is 88.1%, and the purity is 98.4% by HPLC measurement.
Example 3:
196g of cyclohexanone (2 mol) and 33g of hydroxylamine (1 mol) are mixed and added into a stirring reaction vessel with a heating device, and the reaction temperature is controlled to be 152 ℃; after tube sealing and stirring reaction for 1h, naturally cooling to below 60 ℃, adding 98g of cyclohexanone (1 mol), slowly adding 7mL of water and 215g of concentrated sulfuric acid into a reaction container when the temperature of the reaction material is below 40 ℃, then raising the temperature to 110 ℃, stirring and reacting for 10min, completely transferring the materials in the reaction container into water for facilitating product precipitation, uniformly stirring, collecting solids, adding 170g of fuming sulfuric acid, heating to 100 ℃, tube sealing and stirring for 30min, centrifuging after the reaction is completed, obtaining a crude 6-aminocaproic acid product, recrystallizing with ethanol at least twice to obtain a pure 6-aminocaproic acid product, wherein the yield is 86.9%, and the purity is 97.2% by HPLC measurement.
Comparative example 1:
according to the procedure of example 1, the sum of the amounts of cyclohexanone was changed to 98g, i.e. 1mol, 64g was added followed by 34g, and the yield of 6-aminocaproic acid obtained was 59.8% and the HPLC purity was 96.6%.
Comparative example 2:
according to the procedure of example 1, the sum of the amounts of cyclohexanone was changed to 147g, i.e. 1.5mol, 98g was added first and then 49g were added, and the yield of 6-aminocaproic acid obtained was 69.1% and the HPLC purity was 97.1%.
Comparative example 3:
by following the procedure of example 1, the amount of water was changed to 3mL only, and the yield of 6-aminocaproic acid obtained was 71.2% and the HPLC purity was 88.3%.
Comparative example 4:
by following the procedure of example 1, the amount of concentrated sulfuric acid was changed to 100g only, and the yield of 6-aminocaproic acid obtained was 68.4% and the HPLC purity was 89.0%.
Comparative example 5:
by following the procedure of example 1, the amount of fuming sulfuric acid was changed to 100g only, and the yield of 6-aminocaproic acid obtained was 78.6% and the HPLC purity was 78.1%.
Comparative example 6:
according to the procedure of example 1, only the recrystallization step was omitted, and the yield of 6-aminocaproic acid obtained was 81.8% and the HPLC purity was 54.6%.
Comparative example 6:
the procedure of example 1 was followed, and the post-treatment was repeated 1 time to obtain 6-aminocaproic acid in a yield of 83.4% and an HPLC purity of 79.6%.
The foregoing description is only a preferred embodiment of the present invention, and is not intended to limit the invention in any way, but any simple modification or equivalent variation of the above embodiment according to the technology of the present invention falls within the scope of the present invention.
Claims (5)
1. A method for preparing 6-aminocaproic acid by one-step synthesis of cyclohexanone is characterized in that the 6-aminocaproic acid is obtained by taking cyclohexanone and hydroxylamine as raw materials through one-step ring-opening reaction;
the synthetic route is as follows:
the method comprises the following steps:
mixing cyclohexanone and hydroxylamine according to a molar ratio of 2-3:1, adding 2/3 cyclohexanone and hydroxylamine into a stirring reaction vessel with a heating device, and controlling the reaction temperature to be 150-155 ℃; sealing a tube, stirring for reaction for at least 1h, naturally cooling to below 60 ℃, adding the rest cyclohexanone, slowly adding water and concentrated sulfuric acid into a reaction container when the temperature of the reaction material is below 40 ℃, then raising the temperature to 110-115 ℃, stirring for reaction for at least 10min, completely transferring the material in the reaction container into water, uniformly stirring, collecting solids, adding fuming sulfuric acid, heating to 100 ℃, sealing the tube, stirring for reaction for at least 30min, and performing centrifugal separation after the reaction is completed to obtain 6-aminocaproic acid;
the reaction mechanism is as follows:
2. the method of claim 1, wherein the molar volume ratio of hydroxylamine to water is 1 mol:6-8 mL.
3. The method of claim 1, wherein the molar weight ratio of hydroxylamine to concentrated sulfuric acid is 1 mol:200-230 g.
4. The method of claim 1 wherein the molar weight ratio of hydroxylamine to oleum is 1 mol:160-180 g.
5. The method according to claim 1, wherein the obtained 6-aminocaproic acid is crude, further comprising the step of purifying by recrystallization from ethanol at least twice to obtain pure 6-aminocaproic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310496729.1A CN116554045A (en) | 2023-05-05 | 2023-05-05 | Method for preparing 6-aminocaproic acid by cyclohexanone one-step synthesis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310496729.1A CN116554045A (en) | 2023-05-05 | 2023-05-05 | Method for preparing 6-aminocaproic acid by cyclohexanone one-step synthesis |
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| Publication Number | Publication Date |
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| CN116554045A true CN116554045A (en) | 2023-08-08 |
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|---|---|---|---|
| CN202310496729.1A Pending CN116554045A (en) | 2023-05-05 | 2023-05-05 | Method for preparing 6-aminocaproic acid by cyclohexanone one-step synthesis |
Country Status (1)
| Country | Link |
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| CN (1) | CN116554045A (en) |
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2023
- 2023-05-05 CN CN202310496729.1A patent/CN116554045A/en active Pending
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