CN110256268A - A kind of preparation method of aminocaproic acid - Google Patents
A kind of preparation method of aminocaproic acid Download PDFInfo
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- CN110256268A CN110256268A CN201910588353.0A CN201910588353A CN110256268A CN 110256268 A CN110256268 A CN 110256268A CN 201910588353 A CN201910588353 A CN 201910588353A CN 110256268 A CN110256268 A CN 110256268A
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- Prior art keywords
- aminocaproic acid
- preparation
- acid
- caprolactam
- organic solvent
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- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229960002684 aminocaproic acid Drugs 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- 150000007530 organic bases Chemical class 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 12
- 235000019441 ethanol Nutrition 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 238000005292 vacuum distillation Methods 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 13
- 230000035484 reaction time Effects 0.000 abstract description 4
- 238000012805 post-processing Methods 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 238000007789 sealing Methods 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 description 8
- 208000032843 Hemorrhage Diseases 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 208000034158 bleeding Diseases 0.000 description 6
- 231100000319 bleeding Toxicity 0.000 description 6
- 230000000740 bleeding effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 230000006837 decompression Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 2
- 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229960000187 tissue plasminogen activator Drugs 0.000 description 2
- AENOKLOQCCSDAZ-UHFFFAOYSA-N 6-aminohexanoic acid;hydrochloride Chemical compound Cl.NCCCCCC(O)=O AENOKLOQCCSDAZ-UHFFFAOYSA-N 0.000 description 1
- 208000000616 Hemoptysis Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 102000013566 Plasminogen Human genes 0.000 description 1
- 108010051456 Plasminogen Proteins 0.000 description 1
- 206010071229 Procedural haemorrhage Diseases 0.000 description 1
- 108010023197 Streptokinase Proteins 0.000 description 1
- 206010046274 Upper gastrointestinal haemorrhage Diseases 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 206010051373 Wound haemorrhage Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000009098 adjuvant therapy Methods 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940113721 aminocaproate Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000009190 disseminated intravascular coagulation Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000020764 fibrinolysis Effects 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001835 viscera Anatomy 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
- C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of preparation method of aminocaproic acid, in acid condition, then water removal is concentrated under reduced pressure in 1~5h of high pressure tube sealing reaction at 110~130 DEG C to caprolactam；Product is dissolved through organic solvent, adds organic base, is filtered, is drying to obtain.Compared to existing method, the present invention process synthesizing amino caproic acid reaction time is greatly shortened, and postprocessing working procedures are simple, and yield is up to 95%, and purity is 99% or more.
Description
Technical field
The present invention relates to a kind of new processes for preparing aminocaproic acid (6-Aminocaoroic Acid), belong to medical science
Field.
Background technique
Aminocaproic acid is a kind of important fine chemical product and drug.As its injection medicine principal indication are as follows: suitable
For preventing and treating the hyperfunction caused various bleedings of fibrinolysis.
(1) prostate, urethra, lung, liver, pancreas, brain, uterus, adrenal gland, thyroid gland etc. are rich in activator of plasminogen internal organs
Wound or operative hemorrhage, bleeding caused by tissue plasminogen activator (t-PA), streptokinase or urokinase excess.
(2) disseminated intravascular coagulation (DIC) advanced stage, to prevent secondary increased fibrinolytic activity disease.
(3) can be used as haemophiliac get a tooth pulled out or operation on oral cavity after the adjuvant treatment of bleeding or menorrhalgia.
(4) it can be used for the various bleedings such as upper gastrointestinal bleeding, hemoptysis, primary thrombocytopenic purpura and leukaemia
Symptomatic treatment, to general chronic oozing of blood significant effect；It is poor to bleeding caused by dysfunction of blood coagulation；To severe haemorrhage, wound
Mouth is bled profusely and cancerous swelling bleeding etc. is without anastalsis.
Comparative maturity, CN109369430 disclose a kind of preparation method to the route of synthesizing amino caproic acid at this stage: oneself
Then it is complete that dosage form solvent branch solid is added in lactams 80-120 DEG C of reaction in acid system, the white solid of vacuum distillation
Organic amine is added after dissolution and obtains aminocaproic acid crude product, crude yield 85% or so.
A kind of new aminocaproic acid synthesising process research chemical management of Zhao Pengwei, Li Dan, 2019,1 (87) also report
Similar synthetic route is hydrolyzed in acid condition by caprolactam, its aminocaproic acid hydrochloride, amino caproate are obtained
Hydrochlorate is free to obtain aminocaproic acid.
But existing preparation method still remains that the reaction time is longer, the defect of last handling process complexity, and also there are also very for yield
It is big to obtain room for promotion.
Summary of the invention
The technical problem to be solved by the present invention is to short, the yields that in view of the deficiencies of the prior art, provides a kind of reaction time
Height, the method that post-processing simply prepares aminocaproic acid.
In order to achieve the above object, the technical solution adopted by the present invention is as follows:
A kind of preparation method of aminocaproic acid, in acid condition, high pressure tube sealing is anti-at 110~130 DEG C for caprolactam
1~5h (amide occurs hydrolysis and generates carboxylic acid and amino) is answered, water removal is then concentrated under reduced pressure；Product is dissolved through organic solvent,
Organic base is added, filters, be drying to obtain.
Specifically, include the following steps:
(1) caprolactam being dissolved in acidic aqueous solution, is heated to 110~130 DEG C, control reaction pressure is 2~20kg,
React 1~5h；
(2) step (1) carries out vacuum distillation water removal after reaction；
(3) step (2) product is dissolved in organic solvent, and organic base is added or is passed through ammonia, solid is precipitated, filtered, done
It is dry to get aminocaproic acid.
Wherein, in step (1), the acidic aqueous solution is hydrochloric acid, sulfuric acid, nitric acid, any one aqueous solution in phosphoric acid,
Or in which the two or more aqueous solutions for mixing acid, mass concentration are 5~15wt%.
Preferably, in step (1), the mass volume ratio of the caprolactam and acidic aqueous solution is 1kg:4~6L.
In step (3), the organic solvent be methanol, ethyl alcohol, acetone, in DMSO any one or it is two or more mixed
Close object.
Preferably, in step (3), in the organic solvent and step (1) the volume mass ratio of caprolactam be 1~
1.5L:1kg。
Preferably, in step (3), the organic base is triethylamine or ethylenediamine.
The utility model has the advantages that
Compared to existing method, the present invention process synthesizing amino caproic acid reaction time is greatly shortened, and postprocessing working procedures are simple, is received
Rate is up to 95%, and purity is 99% or more.
Detailed description of the invention
The present invention is done with reference to the accompanying drawings and detailed description and is further illustrated, of the invention is above-mentioned
And/or otherwise advantage will become apparent.
Fig. 1 is the infrared spectrogram of aminocaproic acid prepared by embodiment 1.
Fig. 2 is the infrared spectrogram of aminocaproic acid prepared by embodiment 2.
Fig. 3 is the infrared spectrogram of aminocaproic acid prepared by embodiment 3.
Specific embodiment
According to following embodiments, the present invention may be better understood.
Embodiment 1
4kg caprolactam and 20L10% hydrochloric acid are added in 50L high-pressure reaction vessel, is heated to 120 DEG C, reacts 3h, decompression
Distillation water removal.5L ethyl alcohol is added into reaction system, stirring to solid is dissolved, triethylamine is added dropwise at room temperature, after completion of dropwise addition, after
Continuous stirring 5h, filtering, filter cake are dried under reduced pressure to obtain white powdery solids 4.432kg, yield after being beaten washing 3 times with ethyl alcohol
95.6%.
The related substance 99.6% of the aminocaproic acid that embodiment 1 obtains, content 99.8%.
Using the IRAffinity-1S WL infrared tester of SHIMADZU, the infrared spectroscopy of product is measured, as a result sees figure
1, verifying product is aminocaproic acid.
Embodiment 2
4kg caprolactam and 20L5% hydrochloric acid are added in 50L high-pressure reaction vessel, is heated to 110 DEG C, reacts 5h, decompression
Distillation water removal.5L ethyl alcohol is added into reaction system, stirring to solid is dissolved, triethylamine is added dropwise at room temperature, after completion of dropwise addition, after
Continuous stirring 5h, filtering, filter cake are dried under reduced pressure to obtain white powdery solids 4.163kg, yield after being beaten washing 3 times with ethyl alcohol
89.8%.
The related substance 99.0% of the aminocaproic acid that embodiment 2 obtains, content 99.2%.
Fig. 2 is the infrared spectrogram for the aminocaproic acid that embodiment 2 is prepared, and verified product is aminocaproic acid.
Embodiment 3
4kg caprolactam and 20L15% phosphoric acid are added in 50L high-pressure reaction vessel, is heated to 130 DEG C, reacts 1h, decompression
Distillation water removal.5L ethyl alcohol is added into reaction system, stirring to solid is dissolved, triethylamine is added dropwise at room temperature, after completion of dropwise addition, after
Continuous stirring 5h, filtering, filter cake are dried under reduced pressure to obtain white powdery solids 4.270kg, yield after being beaten washing 3 times with ethyl alcohol
92.1%.
The related substance 99.4% of the aminocaproic acid that embodiment 3 obtains, content 99.7%.
Fig. 3 is the infrared spectrogram for the aminocaproic acid that embodiment 3 is prepared, and verified product is aminocaproic acid.
Embodiment 4
4kg caprolactam and 20L5% phosphoric acid are added in 50L high-pressure reaction vessel, is heated to 120 DEG C, reacts 3h, decompression
Distillation water removal.5L ethyl alcohol is added into reaction system, stirring to solid is dissolved, triethylamine is added dropwise at room temperature, after completion of dropwise addition, after
Continuous stirring 5h, filtering, filter cake are dried under reduced pressure to obtain white powdery solids 3.963kg, yield after being beaten washing 3 times with ethyl alcohol
85.5%.
The related substance 99.5% of the aminocaproic acid that embodiment 4 obtains, content 99.6%.
The present invention provides a kind of thinking of the preparation method of aminocaproic acid and methods, implement the side of the technical solution
There are many method and approach, the above is only a preferred embodiment of the present invention, it is noted that for the common skill of the art
For art personnel, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications
Also it should be regarded as protection scope of the present invention.All undefined components in this embodiment can be implemented in the prior art.
Claims (7)
1. a kind of preparation method of aminocaproic acid, which is characterized in that caprolactam is in acid condition, high at 110~130 DEG C
Then water removal is concentrated under reduced pressure in press seal 1~5h of tube reaction；Product is dissolved through organic solvent, adds organic base, and filtering, drying are
?.
2. the preparation method of aminocaproic acid according to claim 1, which comprises the steps of:
(1) caprolactam is dissolved in acidic aqueous solution, is heated to 110~130 DEG C, control reaction pressure is 2~20kg, reaction
1~5h；
(2) step (1) carries out vacuum distillation water removal after reaction；
(3) step (2) product is dissolved in organic solvent, and organic base is added or is passed through ammonia, solid is precipitated, filtered, dried, i.e.,
Obtain aminocaproic acid.
3. the preparation method of aminocaproic acid according to claim 2, which is characterized in that in step (1), the acidity is water-soluble
Liquid is that hydrochloric acid, sulfuric acid, nitric acid, any one aqueous solution in phosphoric acid or in which the two or more aqueous solutions for mixing acid, quality are dense
Degree is 5~15wt%.
4. the preparation method of aminocaproic acid according to claim 2, which is characterized in that in step (1), the caprolactam
Mass volume ratio with acidic aqueous solution is 1kg:4~6L.
5. the preparation method of aminocaproic acid according to claim 2, which is characterized in that in step (3), the organic solvent
For any one or the two or more mixtures in methanol, ethyl alcohol, acetone, DMSO.
6. the preparation method of aminocaproic acid according to claim 2, which is characterized in that in step (3), the organic solvent
Volume mass ratio with caprolactam in step (1) is 1~1.5L:1kg.
7. the preparation method of aminocaproic acid according to claim 2, which is characterized in that in step (3), the organic base is
Triethylamine or ethylenediamine.
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| CN201910588353.0A CN110256268A (en) | 2019-07-02 | 2019-07-02 | A kind of preparation method of aminocaproic acid |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114163344A (en) * | 2021-12-20 | 2022-03-11 | 昌德新材科技股份有限公司 | Method for preparing 6-aminocaproic acid |
| CN114195663A (en) * | 2021-12-20 | 2022-03-18 | 昌德新材科技股份有限公司 | Preparation method of 6-aminocaproic acid |
| CN116574022A (en) * | 2023-05-05 | 2023-08-11 | 常州兰陵制药有限公司 | Preparation method of high-purity 6-aminocaproic acid |
| CN116836073A (en) * | 2023-05-05 | 2023-10-03 | 常州兰陵制药有限公司 | Method for preparing 6-aminocaproic acid by using pimelic acid as raw material |
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| CN114163344A (en) * | 2021-12-20 | 2022-03-11 | 昌德新材科技股份有限公司 | Method for preparing 6-aminocaproic acid |
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| CN116574022A (en) * | 2023-05-05 | 2023-08-11 | 常州兰陵制药有限公司 | Preparation method of high-purity 6-aminocaproic acid |
| CN116836073A (en) * | 2023-05-05 | 2023-10-03 | 常州兰陵制药有限公司 | Method for preparing 6-aminocaproic acid by using pimelic acid as raw material |
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