CN106467453B - A kind of method of pipeline reactor synthesis P-methoxybenzoic acid - Google Patents
A kind of method of pipeline reactor synthesis P-methoxybenzoic acid Download PDFInfo
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- CN106467453B CN106467453B CN201610775226.8A CN201610775226A CN106467453B CN 106467453 B CN106467453 B CN 106467453B CN 201610775226 A CN201610775226 A CN 201610775226A CN 106467453 B CN106467453 B CN 106467453B
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- pipeline reactor
- hydroxybenzoate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
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- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention is using pipeline reactor as consersion unit, without using catalyst, methyl p-hydroxybenzoate and sodium hydrate aqueous solution are first configured to Sodium Methyl Hydroxybenzoate salting liquid, then again with methylating reagent dimethyl carbonate is etherified, saponification, acid out obtain P-methoxybenzoic acid.High conversion rate of the present invention, purity is high, and process is micro controllable, and safety coefficient is high, and the three wastes are few, and floor space is small, it can be achieved that high production capacity new type of continuous chemical industry production.
Description
Technical field
The invention belongs to field of fine chemical, it is related to the synthesis of common chemicals, and in particular to P-methoxybenzoic acid first
The industry of ester is combined to.
Background technology
P-methoxybenzoic acid is important cosmetic additive agent and medicine intermediate, and traditional handicraft is with para hydroxybenzene first
Acid be raw material under alkaline condition with dimethyl suflfate methylation reaction, then sulfuric acid be acidified to obtain.The disadvantage is that：1, dimethyl sulfate
Ester toxicity is big；2, a large amount of spent acid and waste water be will produce in producing.
Although Huang, Yao-Dong et al.（“Structure-property correlation of benzoyl
thiourea derivatives as organogelators” Journal of Molecular Structure, 1031,
43-48; 2013）It discloses and uses bromomethane as methylating reagent, using methyl p-hydroxybenzoate as starting material synthesis pair
Methoxy benzoic acid, but bromomethane is a kind of substance of ozone layer depletion, according to《It corrects in Montreal Protocol Copenhagen
Case》, developed country eliminated in 2005, and developing country will also eliminate in 2015.And not due to dimethyl carbonate activity
Height, the reaction response time is longer, does not utilize energy saving and cost, not only additionally consumes mass energy, same time delay in this way
The production cycle has been grown, the production efficiency of reaction unit is reduced, and has been easy to cause product jaundice, has influenced product appearance, and receive
Rate is not high.
Pipeline reactor, to adding various coagulant, flocculation aid, ozone, liquid chlorine and acid in plumbing and environment-friendly engineering
Alkali neutralization, mixing wastewater with air etc. are all highly effective, are the ideal equipments for handling the various medicaments in waters and realizing moment mixing, have
The features such as rapidly and efficiently mixing, is simple in structure, saving energy consumption, compact, is being not required to outer power, flow passes through pipeline
Reactor will produce shunting, cross-mixing and the effect of reversed eddy flow three, make that the medicament of addition is rapid, it is entire to be uniformly spread to
In water body, achieve the purpose that moment mixes.
Invention content
To solve the deficiencies in the prior art, the present invention provides a kind of P-methoxybenzoic acid is synthesized using pipeline reactor
System and method, specific technical solution is as follows：
The technical program is using pipeline reactor as consersion unit, without using catalyst, methyl p-hydroxybenzoate and hydrogen
Aqueous solution of sodium oxide is first configured to Sodium Methyl Hydroxybenzoate salting liquid, then again with methylating reagent dimethyl carbonate through ether
Change, saponification, acid out obtain P-methoxybenzoic acid.High conversion rate of the present invention, purity is high, and process is micro controllable, and safety coefficient is high,
The three wastes are few, and floor space is small, it can be achieved that high production capacity new type of continuous chemical industry production.
By the optimization to reaction process, the present inventor has obtained following preferably working condition：
Methyl p-hydroxybenzoate and sodium hydrate aqueous solution are configured to the Sodium Methyl Hydroxybenzoate salt of 25-45%
Solution.
The molar ratio of methyl p-hydroxybenzoate and dimethyl carbonate is 1:（0.5-1）.
Pipeline reactor uses stages cycle water control temperature, and level-one pipeline reactor is controlled at 50 DEG C；Secondary canalization is anti-
It is 90 DEG C to answer device；Three-level pipeline reactor is 50 DEG C.
Material flow selects 0.1~10L/min.
Any inorganic caustic solutions, preferably 20-40% sodium hydrate aqueous solutions can be used in saponification.Any nothing can be used in acid out
Machine acid solution, preferably 40-60% dilute sulfuric acids.
The method of the present invention is specially：
（1）It is molten that methyl p-hydroxybenzoate is first configured to Sodium Methyl Hydroxybenzoate salt with sodium hydrate aqueous solution
The solution is pumped into static mixer by feed inlet, while dimethyl carbonate is pumped into static mixer by feed inlet by liquid,
Level-one pipeline reactor is passed through recirculated water, and material is after static mixer, into level-one pipeline reactor；
（2）Reaction after a certain period of time, after liquid flows through static mixer, into secondary canalization reactor, while from charging
Mouth is pumped into sodium hydrate aqueous solution, and secondary canalization reactor is passed through recirculated water；
（3）Reaction after a certain period of time, after liquid flows through static mixer, into third level pipeline reactor, while from into
Material mouth is pumped into dilution heat of sulfuric acid, and three-level pipeline reactor is passed through recirculated water, and after a certain period of time, material enters through pipe end for reaction
Automatic centrifuge is separated by solid-liquid separation.
Description of the drawings
Fig. 1 pipeline reactors used in the present invention, wherein 1 be methyl p-hydroxybenzoate and sodium hydrate aqueous solution,
The feed inlet of dimethyl carbonate；2 be static mixer；3 be level-one pipeline reactor；4 be sodium hydrate aqueous solution feed inlet；5
For secondary canalization reactor；6 be dilution heat of sulfuric acid feed inlet；7 be three-level pipeline reactor；8 be material outlet；9,10,11
To be passed through the entrance of recirculated water.
Specific embodiment
Embodiment 1 first by the methyl p-hydroxybenzoate of 32.2kg and sodium hydrate aqueous solution prepare 35% to hydroxyl
Methyl benzoate sodium salt solution.By the solution with 0.096m3The speed of/h is pumped into static mixer by feed inlet, simultaneously will
The dimethyl carbonate of 13.3kg is with 0.013m3The speed of/h is pumped into static mixer, methyl p-hydroxybenzoate by feed inlet
It is 1 with dimethyl carbonate molar ratio:0.7.Level-one pipeline reactor is passed through 50oC recirculated waters.After 30min, liquid flows through static mixed
After clutch, 0.023m is pumped into secondary canalization reactor, while from feed inlet330% sodium hydrate aqueous solutions of/h.Diode
Road reactor is passed through 90oC recirculated waters.After 20min, after liquid flows through static mixer, into third level pipeline reactor, together
When from feed inlet be pumped into 0.02m350% dilute sulfuric acids of/h, three-level pipeline reactor are passed through 50oC recirculated waters.After 10min, material warp
Pipe end enters automatic centrifuge and is separated by solid-liquid separation, and single group reactor can obtain white P-methoxybenzoic acid solid per hour
About 36kg（Dry to obtain 30.8kg）, yield is about 95.6%.
Embodiment 2
The methyl p-hydroxybenzoate of 32.2kg and sodium hydrate aqueous solution are first prepared to 30% P-hydroxybenzoic acid first
Ester sodium salt solution.By the solution with 0.096m3The speed of/h is pumped into static mixer by feed inlet, while by the carbon of 15.2kg
Dimethyl phthalate is with 0.013m3The speed of/h is pumped into static mixer, methyl p-hydroxybenzoate and carbonic acid diformazan by feed inlet
Ester molar ratio is 1:0.8.Level-one pipeline reactor is passed through 50oC recirculated waters.After 30min, after liquid flows through static mixer, into
Enter secondary canalization reactor, while 0.023m is pumped into from feed inlet340% sodium hydrate aqueous solutions of/h.Secondary canalization reactor is logical
Enter 90oC recirculated waters.After 20min, after liquid flows through static mixer, into third level pipeline reactor, while from feed inlet
It is pumped into 0.02m345% dilute sulfuric acids of/h, three-level pipeline reactor are passed through 50oC recirculated waters.After 10min, material through pipe end into
Enter automatic centrifuge to be separated by solid-liquid separation, single group reactor can obtain white P-methoxybenzoic acid solid about 35.6kg per hour
（Dry to obtain 30.5kg）, yield is about 94.7%.
Embodiment 3
The methyl p-hydroxybenzoate of 32.2kg and sodium hydrate aqueous solution are first prepared to 45% P-hydroxybenzoic acid first
Ester sodium salt solution.By the solution with 0.096m3The speed of/h is pumped into static mixer by feed inlet, while by the carbon of 10.5kg
Dimethyl phthalate is with 0.013m3The speed of/h is pumped into static mixer, methyl p-hydroxybenzoate and carbonic acid diformazan by feed inlet
Ester molar ratio is 1:0.55.Level-one pipeline reactor is passed through 50oC recirculated waters.After 30min, after liquid flows through static mixer, into
Enter secondary canalization reactor, while 0.023m is pumped into from feed inlet325% sodium hydrate aqueous solutions of/h.Secondary canalization reactor is logical
Enter 90oC recirculated waters.After 20min, after liquid flows through static mixer, into third level pipeline reactor, while from feed inlet
It is pumped into 0.02m355% dilute sulfuric acids of/h, three-level pipeline reactor are passed through 50oC recirculated waters.After 10min, material through pipe end into
Enter automatic centrifuge to be separated by solid-liquid separation, single group reactor can obtain white P-methoxybenzoic acid solid about 359kg per hour（It dries
Obtain 30kg）, yield is about 93.0%.
Claims (7)
1. a kind of method of pipeline reactor synthesis P-methoxybenzoic acid, which is characterized in that be with methyl p-hydroxybenzoate
Raw material obtains P-methoxybenzoic acid with methylating reagent dimethyl carbonate after etherificate, saponification, acid out, and reaction is set
Standby is three-level pipeline reactor, specifically：
(1) methyl p-hydroxybenzoate and sodium hydrate aqueous solution are first configured to Sodium Methyl Hydroxybenzoate salting liquid, it will
The solution is pumped into static mixer by feed inlet, while dimethyl carbonate is pumped into static mixer, level-one by feed inlet
Pipeline reactor is passed through recirculated water, and material is after static mixer, into level-one pipeline reactor；
(2) reaction after a certain period of time, after liquid flows through static mixer, is pumped into secondary canalization reactor, while from feed inlet
Enter sodium hydrate aqueous solution, secondary canalization reactor is passed through recirculated water；
(3) reaction after a certain period of time, after liquid flows through static mixer, into third level pipeline reactor, while from feed inlet
It is pumped into dilution heat of sulfuric acid, three-level pipeline reactor is passed through recirculated water, and after a certain period of time, material enters automatic through pipe end for reaction
Centrifuge is separated by solid-liquid separation；
Level-one pipeline reactor is controlled at 50 DEG C；Secondary canalization reactor is 90 DEG C；Three-level pipeline reactor is 50 DEG C.
2. the method as described in claim 1, which is characterized in that methyl p-hydroxybenzoate and sodium hydrate aqueous solution before reaction
It is configured to the Sodium Methyl Hydroxybenzoate salting liquid of 25-45%.
3. the method as described in claim 1, which is characterized in that methyl p-hydroxybenzoate is 1 with dimethyl carbonate molar ratio:
(0.5-1)。
4. the method as described in claim 1, which is characterized in that material flow is 0.1~10L/min.
5. the method as described in claim 1, which is characterized in that the solution that saponification uses is 20-40% sodium hydrate aqueous solutions.
6. the method as described in claim 1, which is characterized in that the solution that acid out uses is 40-60% dilute sulfuric acids.
7. the method as described in claim 1-6 is any, which is characterized in that this method is：
(1) that methyl p-hydroxybenzoate with sodium hydrate aqueous solution is first configured to 35% Sodium Methyl Hydroxybenzoate salt is molten
Liquid, by the solution with 0.096m3The speed of/h is pumped into static mixer by feed inlet, at the same by dimethyl carbonate with
0.013m3The speed of/h is pumped into static mixer by feed inlet, and level-one pipeline reactor is passed through 50 DEG C of recirculated waters；
(2) reaction after a certain period of time, after liquid flows through static mixer, is pumped into secondary canalization reactor, while from feed inlet
Enter 0.023m330% sodium hydrate aqueous solutions of/h, secondary canalization reactor are passed through 90 DEG C of recirculated waters；
(3) reaction after a certain period of time, after liquid flows through static mixer, into third level pipeline reactor, while from feed inlet
It is pumped into 0.02m350% dilution heat of sulfuric acid of/h, three-level pipeline reactor are passed through 50 DEG C of recirculated waters, react after a certain period of time, material
Enter automatic centrifuge through pipe end to be separated by solid-liquid separation.
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| CN201610775226.8A CN106467453B (en) | 2016-08-31 | 2016-08-31 | A kind of method of pipeline reactor synthesis P-methoxybenzoic acid |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4249015A (en) * | 1976-07-23 | 1981-02-03 | Shell Oil Company | Preparation of organic acids and/or esters |
| CN101143828A (en) * | 2007-04-13 | 2008-03-19 | 青岛银科恒远化工过程信息技术有限公司 | Continuous reaction technique for producing crude MDA |
| CN101781609A (en) * | 2010-03-03 | 2010-07-21 | 北京国力源高分子科技研发中心 | Method for preparing biodiesel from hemp plant oil |
-
2016
- 2016-08-31 CN CN201610775226.8A patent/CN106467453B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4249015A (en) * | 1976-07-23 | 1981-02-03 | Shell Oil Company | Preparation of organic acids and/or esters |
| CN101143828A (en) * | 2007-04-13 | 2008-03-19 | 青岛银科恒远化工过程信息技术有限公司 | Continuous reaction technique for producing crude MDA |
| CN101781609A (en) * | 2010-03-03 | 2010-07-21 | 北京国力源高分子科技研发中心 | Method for preparing biodiesel from hemp plant oil |
Non-Patent Citations (2)
| Title |
|---|
| Alkylation. I. Methylation of the isomeric hydroxybenzoic acids with methyl sulfate;Nozu, Ryuzaburo等;《Nippon Kagaku Kaishi》;19391231;第60卷;第1189-1194页 * |
| 对甲氧基苯甲酸的制备;孟祥军等;《化学世界》;19951231(第2期);第83-84页 * |
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