CN104829453A - Preparation method of acetylsalicylic acid - Google Patents
Preparation method of acetylsalicylic acid Download PDFInfo
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- CN104829453A CN104829453A CN201510234745.9A CN201510234745A CN104829453A CN 104829453 A CN104829453 A CN 104829453A CN 201510234745 A CN201510234745 A CN 201510234745A CN 104829453 A CN104829453 A CN 104829453A
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- CN
- China
- Prior art keywords
- acetylsalicylic acid
- acid
- whitfield
- ointment
- reaction
- 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.)
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- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229960001138 acetylsalicylic acid Drugs 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000967 suction filtration Methods 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 claims description 13
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 9
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract description 4
- 239000013078 crystal Substances 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract description 2
- 238000005457 optimization Methods 0.000 abstract description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract description 2
- 229960004889 salicylic acid Drugs 0.000 abstract description 2
- 238000001816 cooling Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 13
- 150000008065 acid anhydrides Chemical class 0.000 description 12
- 238000010586 diagram Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- -1 acetyl Whitfield's ointment Chemical compound 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000002612 cardiopulmonary effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000250 revascularization Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of acetylsalicylic acid. The method is characterized by comprising the following steps: mixing salicylic acid, acetic anhydride and citric acid; reacting at a water bath temperature of 70 DEG C for 40 minutes; washing the inner wall of a reaction container with cold water; forming crystal, adding water and cooling in an ice bath for 30 minutes; and carrying out suction filtration, and drying in an oven, so as to obtain the acetylsalicylic acid. The method disclosed by the invention is simple, low in cost, small in damages to equipment and free of environment pollution; through optimization of a catalyst and the conditions such as the reaction temperature and reaction time, the amount of the catalyst is reduced; and the yield of the product can be greatly improved.
Description
Technical field
The present invention relates to a kind of method for preparing acetylsalicylic acid, belong to chemical technology field.
Background technology
Acetylsalicylic acid has another name called acetylsalicylic acid, and acetylsalicylic acid is a kind of time-honored antipyretic and analgesic, is born on March 6th, 1899.For curing cold, generating heat, have a headache, have a toothache, arthrodynia, rheumatosis, can also anticoagulant, for prevention and therapy ischemic heart disease, stenocardia, cardiopulmonary infraction, cerebral thrombosis, be applied to revascularization and bypass graft is also effective.Not only there is purposes medically over 100 years, and also have extensive use at other field.It is that salicylic acid is antipyretic, the representative of anodyne, for clinical T&B.It is white needles or plate crystal or powder, fusing point 135 DEG C, odorlessness, micro-band tart flavour, stable in dry air, Whitfield's ointment and acetic acid is slowly hydrolyzed in damp atmosphere, can ethanol be dissolved in, EC, be slightly soluble in water, can dissolve in sodium hydroxide solution or sodium carbonate solution, but decompose simultaneously.
Classical preparation method obtains Whitfield's ointment acidylate under sulfuric acid catalysis with diacetyl oxide or Acetyl Chloride 98Min., and this technical maturity, productive rate is about 60%, but side reaction is many, and equipment corrosion is serious, serious environment pollution.For exploitation raw catalyst, tosic acid on probation, sodium pyrosulfate etc., but recirculation use properties is poor.Thus the new problem that the new catalytic activity of a class is high, the catalyzer of environment-friendly type is studied to replace Protic Acid Catalyzed synthesis of acetyl Whitfield's ointment to become people is found.Existing a lot of research both at home and abroad, catalyze and synthesize by Acidic Bentonite, catalyst preparing is cumbersome; Microwave irradiation synthesis, though speed of response is fast, theory and practice exists many problems; Lanthanide terchlorides catalysis, effective, but there is the problems such as rare earth price is more expensive.
Summary of the invention
In order to overcome prior art problem, the object of the present invention is to provide the method for preparing acetylsalicylic acid that a kind of productive rate is high.
For solving the problems of the technologies described above, the technical solution used in the present invention is:
A kind of method for preparing acetylsalicylic acid, it is characterized in that, comprise the following steps: after Whitfield's ointment, diacetyl oxide and citric acid are mixed, under the bath temperature condition of 70 DEG C, react 40min, then use cold water washing reaction vessel inwall, after forming crystallization, add water, and with ice bath in cool 30min, suction filtration to be placed in baking oven dry, obtains acetylsalicylic acid.
Further, the amount of substance ratio (the amount of substance ratio hereinafter referred to as acid anhydrides) of described Whitfield's ointment and diacetyl oxide is 1:3.
The quality that adds of described citric acid is that Whitfield's ointment adds 1/3 of quality.
And the add-on of described water and salicylic solid-liquid ratio are: 15ml:1g.
The temperature of drying is then 90 DEG C.
Beneficial effect of the present invention is: the method for the invention is simple, and cost is low, and the little and non-environmental-pollution of equipment nocuity, by optimization of catalysts and the condition such as temperature of reaction, reaction times, makes the consumption of catalyzer few, and greatly can improve the productive rate of product.
Accompanying drawing explanation
Fig. 1 be the amount of substance comparison product yield of acid anhydrides affect schematic diagram;
Fig. 2 is that catalyst levels affects schematic diagram to product yield;
Fig. 3 affects schematic diagram to product yield in the reaction times;
Fig. 4 is that temperature of reaction affects schematic diagram to product yield.
Embodiment
The present invention is described in detail below in conjunction with specific embodiment.
embodiment 1:
Get Whitfield's ointment 3.0g, citric acid 1.0g, 70 DEG C of reaction 30min, change acid anhydrides amount of substance ratio, to rub the impact of comparison product yield, the results are shown in Table 1 and Fig. 1 to investigate acid anhydrides.
The impact of table 1 acid anhydrides amount of substance comparison product yield
。
From Fig. 1 and table 1: along with acid anhydrides amount of substance is than increasing, the abundant acidylate of Whitfield's ointment, product yield is along with increase; Arrive certain than after, along with acid anhydrides amount of substance is than increase, because portioned product is dissolved in diacetyl oxide, cause yield to decline.Best acid anhydrides amount of substance is than being 1:3.
embodiment 2:
Get acid anhydrides amount of substance than being 1:3, wherein, Whitfield's ointment 3.0g, 70 DEG C of reaction 30min, change catalyzer Citric Acid Dosage, investigate catalyzer Citric Acid Dosage to the impact of product yield, the results are shown in Table 2 and Fig. 2.
Table 2 catalyst levels is on the impact of acetylsalicylic acid yield
。
From Fig. 2 and table 2, along with the increase of catalyst levels, product yield is along with increase, and after a certain amount of, reach maximum value, product yield declines on the contrary, and participate in reaction due to citric acid and cause, therefore, citric acid optimum amount is 1.0g.
embodiment 3:
Get acid anhydrides amount of substance than being 1:3, wherein, Whitfield's ointment 3.0g, citric acid gets 1.0g, temperature 75 DEG C, changes the reaction times, to investigate the impact of reaction times on product yield, the results are shown in Table 3 and Fig. 3.
Table 3 reaction times is on the impact of product yield
。
As shown in table 3 and Fig. 3:, the reaction times is too short, and reactant unreacted is complete, and product yield is low; Long reaction time, possible by product increases, therefore product yield is also low, and optimum reacting time is 40min.
embodiment 4:
Get acid anhydrides amount of substance than being 1:3, wherein, Whitfield's ointment 3.0g, citric acid gets 1.0g, and the reaction times is 40min, changes temperature of reaction, to investigate the impact of temperature of reaction on product yield, the results are shown in Table 4 and Fig. 4.
Table 4 temperature of reaction is on the impact of product yield
。
From table 4 and Fig. 4, temperature is too low or too high is all unfavorable for the carrying out that react, and it is many to pay reaction during temperature height, or part acetylsalicylic acid decomposes, and because the productive rate difference of 70 DEG C and 80 DEG C is not quite with the principle of save energy when being catalyzer with citric acid, optimum temps is 70 DEG C.
From above four embodiments: citric acid is optimum catalyst and optimum reaction condition is that acid anhydrides amount of substance is than being 1:3, Citric Acid Dosage is 1.0g, reaction times is 40min, temperature of reaction is 70 DEG C, then uses cold water washing reaction vessel inwall, after forming crystallization, add water, and with ice bath in cool 30min, suction filtration to be placed in baking oven dry, obtains acetylsalicylic acid.Acetylsalicylic acid (acetylsalicylic acid) yield reaches 89.8%, is with a wide range of applications.
The present invention is illustrated according to above-described embodiment and should be appreciated that above-described embodiment does not limit the present invention in any form, and all employings are equal to replacement or the technical scheme that obtains of equivalent transformation mode, all drop within protection scope of the present invention.
Claims (5)
1. a method for preparing acetylsalicylic acid, it is characterized in that, comprise the following steps: after Whitfield's ointment, diacetyl oxide and citric acid are mixed, under the bath temperature condition of 70 DEG C, react 40min, then use cold water washing reaction vessel inwall, after forming crystallization, add water, and with ice bath in cool 30min, suction filtration to be placed in baking oven dry, obtains acetylsalicylic acid.
2. a kind of method for preparing acetylsalicylic acid according to claim 1, is characterized in that, described Whitfield's ointment and the mass ratio of diacetyl oxide are 1:3.
3. a kind of method for preparing acetylsalicylic acid according to claim 1, is characterized in that, the quality that adds of described citric acid is that Whitfield's ointment adds 1/3 of quality.
4. a kind of method for preparing acetylsalicylic acid according to claim 1, is characterized in that, add-on and the salicylic solid-liquid ratio of described water are: 15ml:1g.
5. a kind of method for preparing acetylsalicylic acid according to claim 1, is characterized in that, dry temperature is 90 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510234745.9A CN104829453A (en) | 2015-05-11 | 2015-05-11 | Preparation method of acetylsalicylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510234745.9A CN104829453A (en) | 2015-05-11 | 2015-05-11 | Preparation method of acetylsalicylic acid |
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| Publication Number | Publication Date |
|---|---|
| CN104829453A true CN104829453A (en) | 2015-08-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510234745.9A Pending CN104829453A (en) | 2015-05-11 | 2015-05-11 | Preparation method of acetylsalicylic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104829453A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880663A (en) * | 2012-12-24 | 2014-06-25 | 青岛康地恩动物药业有限公司 | Aspirin preparation method |
-
2015
- 2015-05-11 CN CN201510234745.9A patent/CN104829453A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880663A (en) * | 2012-12-24 | 2014-06-25 | 青岛康地恩动物药业有限公司 | Aspirin preparation method |
Non-Patent Citations (2)
| Title |
|---|
| 隆金桥等: "柠檬酸催化合成阿司匹林", 《云南化工》 * |
| 黄飞: "乙酰水杨酸催化合成条件的研究", 《黄山学院学报》 * |
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| EXSB | Decision made by sipo to initiate substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150812 |