CN106397193A - Preparation method of ethyl paraben - Google Patents
Preparation method of ethyl paraben Download PDFInfo
- Publication number
- CN106397193A CN106397193A CN201610768164.8A CN201610768164A CN106397193A CN 106397193 A CN106397193 A CN 106397193A CN 201610768164 A CN201610768164 A CN 201610768164A CN 106397193 A CN106397193 A CN 106397193A
- Authority
- CN
- China
- Prior art keywords
- preparation
- ethanol
- ethylparaben
- hydroxybenzoic acid
- ethyl paraben
- 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.)
- Pending
Links
- 229960001617 ethyl hydroxybenzoate Drugs 0.000 title claims abstract description 24
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 title claims abstract description 24
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 title claims abstract description 24
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 45
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims abstract description 18
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims abstract description 13
- 229910000342 sodium bisulfate Inorganic materials 0.000 claims abstract description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 239000012153 distilled water Substances 0.000 claims abstract description 6
- 239000012065 filter cake Substances 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 6
- 238000004140 cleaning Methods 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000011010 flushing procedure Methods 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 239000012265 solid product Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- 238000005260 corrosion Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000007797 corrosion Effects 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 239000013078 crystal Substances 0.000 abstract 2
- 238000005406 washing Methods 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000967 suction filtration Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 235000013305 food Nutrition 0.000 description 10
- 235000019249 food preservative Nutrition 0.000 description 8
- 239000005452 food preservative Substances 0.000 description 8
- 239000003755 preservative agent Substances 0.000 description 8
- 230000002335 preservative effect Effects 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 5
- -1 isobutyl ester Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 235000010199 sorbic acid Nutrition 0.000 description 5
- 239000004334 sorbic acid Substances 0.000 description 5
- 229940075582 sorbic acid Drugs 0.000 description 5
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 235000010241 potassium sorbate Nutrition 0.000 description 4
- 239000004302 potassium sorbate Substances 0.000 description 4
- 229940069338 potassium sorbate Drugs 0.000 description 4
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 4
- 235000010234 sodium benzoate Nutrition 0.000 description 4
- 239000004299 sodium benzoate Substances 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 235000013405 beer Nutrition 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000012055 fruits and vegetables Nutrition 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZTJORNVITHUQJA-UHFFFAOYSA-N Heptyl p-hydroxybenzoate Chemical compound CCCCCCCOC(=O)C1=CC=C(O)C=C1 ZTJORNVITHUQJA-UHFFFAOYSA-N 0.000 description 1
- CMHMMKSPYOOVGI-UHFFFAOYSA-N Isopropylparaben Chemical compound CC(C)OC(=O)C1=CC=C(O)C=C1 CMHMMKSPYOOVGI-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019251 heptyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000750 industrial fungicide Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000019991 rice wine Nutrition 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of ethyl paraben. The preparation method comprises the following steps: adding p-hydroxybenzoic acid, a certain amount of ethanol, and sodium hydrogen sulfate into a 3-mouth flask, evenly mixing, adding an electromagnetic stir bar, placing the 3-mouth flask into a microwave oven, starting to stir, carrying out reactions, wherein during the reaction process, the water in the water separator should be discharged in time; after 1 to 2.5 hours, shutting off the power supply, pouring the reaction liquid into a clean 3-mouth flask, removing excess ethanol by using water steam to carry out distillation, cooling and crystallizing the residual liquid after distillation, washing the obtained crystals by a sodium carbonate solution (10%) until the pH value of crystals reaches 7.5-8.0, carrying out suction filtration, and washing the filter cake by distilled water to obtain white ethyl paraben. According to the preparation method, sodium hydrogen sulfate is taken as the catalyst, p-hydroxybenzoic acid and ethanol are taken as the raw materials, ethyl paraben is prepared by a microwave method, the excess ethanol can be recovered and reused; the corrosion on equipment is little, the environment pollution is little, the yield of ethyl paraben is high, the purity is good, and the preparation method is simple and is suitable for industrial production.
Description
Technical field
The present invention relates to chemical technology field, specifically a kind of preparation method of ethylparaben.
Background technology
P-Hydroxybenzoate is class a new generation high-efficiency low-toxicity disinfection preservative, and its antibacterial ability compares benzoic acid
Strong with sorbic acid and its esters, application pH scope is wider than benzoic acid and sorbic acid and its esters, amount ratio benzoic acid and sorbic acid
And its esters is much lower, and use safety, economical convenient, human body is stimulated less.Abroad, have been widely used for food,
The aspects such as beverage, cosmetics and medicine.It is main preservative product in Japan, p-Hydroxybenzoate and sorbic acid.And in
State, the major product of preservative is still sodium benzoate, and the product of potassium sorbate also increases year by year, becomes second master of preservative
Want product.Produce p-Hydroxybenzoate, domestic only have several producers, and small, and product only includes para hydroxybenzene
A few product of methyl formate, ethyl ester and propyl ester, p-Hydroxybenzoic acid isopropyl ester, butyl ester, isobutyl ester, pentyl ester, isopentyl ester,
Ester, heptyl ester and monooctyl ester etc., domestic all do not have production.Therefore, develop the different formate ester of food preservative para hydroxybenzene of new generation, no
Increase only the kind of Chinese food preservative, reduce the difference with foreign foods preservative.More importantly, it is Chinese food
Industry provides the anticorrosion and bactericidal agent of high-efficiency low-toxicity of new generation, promotes developing rapidly of Chinese food industry.
With the reform of China's economic system, the yield of the various agricultural byproducts such as water fruits and vegetables is significantly increased production, for China
The development of food industry, provides wide raw materials market, and this is diversified, flavoured, efficient with regard to an urgent demand food and drink
Change and storage-stable etc..The great variety of this structure be unable to do without the additive of food and drink, such as flavorant, fortification
Agent, food quality modifying agent, food preservative etc..Wherein food preservative is that a class is important, and is the maximum food of consumption
Product additive.The food preservative that countries in the world use at present is planted more than more than 50, as many as existing 25 kinds of Japan, and with to hydroxyl
Based on yl benzoic acid esters and sorbic acid.China is at present still based on sodium benzoate and potassium sorbate.Kind is dull, antiseptic effect
Difference, is China's subject matter that food preservative market exists at present.Therefore, research and development and application scope is wide, favorable anti-corrosion effect,
Small toxicity, the low Novel series preservative of integrated cost, to adapt to the needs of Chinese food industrial development, imperative.
The market demand analysis of project and domestic and international technology trends：Paraben preservative, is a class
The preservative of new and effective low toxicity, China in addition to several producer's small-scale production p-Hydroxybenzoates, ethyl ester and propyl ester,
Other esters still belong to blank at home.In p-Hydroxybenzoate, the carbon atomic number of alkyl is bigger, its production technology difficulty
Bigger, but bactericidal action is stronger, particularly n Heptyl p hydroxybenzoate and monooctyl ester, add in unpasteurized beer its effect of 8-12ppm with
Heat sterilization effect is identical, and freshness date was up to more than 12 months.Parabenses can be used not only as food preservative, also
Can be used for cosmetics, medicine and industrial fungicide.Only cosmetic industry, the annual demand in the whole nation just reaches more than 100 tons.Cause
This, parabenses are the products that a class market prospect is extremely got better.As food preservative, it can be used for beverage,
In the processed goods such as garden stuff processing product, marine products processed goods, poultry processed goods, flavoring agent, medicated beer, rice wine, can be additionally used in water fruits and vegetables
Anti-corrosive fresh-keeping with marine product.It not only can substitute sodium benzoate and potassium sorbate completely, its range than sodium benzoate and
Potassium sorbate is wider.Therefore, parabenses have very big market capacity.
Content of the invention
It is an object of the invention to provide a kind of preparation method of ethylparaben.
The purpose of the present invention can be achieved through the following technical solutions：
A kind of preparation method of ethylparaben is it is characterised in that comprise the following steps：
(1) add P-hydroxybenzoic acid, a certain amount of ethanol and sodium bisulfate, mix homogeneously in there-necked flask, place into
Electromagnetic agitation, is placed in microwave oven, starts stirring, starts to react, and releases the water separating in water knockout drum in course of reaction in time；
(2) close power supply after reaction 1-2.5h, reaction liquid is poured in the there-necked flask of cleaning and was gone out with vapor distillation
The ethanol of amount, still residue is poured in clean beaker, cooling crystallization, and being washed to pH value with 10% sodium carbonate liquor is 7.5-
8.0, sucking filtration, use distilled water flushing filter cake, be dried, obtain white solid product ethylparaben.
Scheme further, in described step (1), P-hydroxybenzoic acid and the mol ratio of ethanol are 1:3-5.
Scheme further, in described step (1), the addition of sodium bisulfate is the 9-10.2% of P-hydroxybenzoic acid quality.
Scheme further, in described step (1), mixing speed is 200-300r/min.
Further scheme, in described step (1) microwave irradiation power of microwave oven be 400-600W, microwave radiation temperature be
120-130 DEG C, microwave irradiation time be 10-60min.
Beneficial effects of the present invention：The present invention with sodium bisulfate as catalyst, with P-hydroxybenzoic acid and ethanol as raw material,
Ethylparaben, the recyclable recycling of ethanol of excess, environmental pollution little to equipment corrosion are prepared using microwave method
Little, catalyst amount is few, ethylparaben high income, and purity is good, and preparation method is simple, suitable industrialized production.
Specific embodiment
With reference to specific embodiment, the present invention is described in further detail.
Embodiment 1
P-hydroxybenzoic acid, a certain amount of ethanol and sodium bisulfate, P-hydroxybenzoic acid and ethanol is added in there-necked flask
Mol ratio be 1:3；The addition of sodium bisulfate is the 9% of P-hydroxybenzoic acid quality, and mouth plug grinding port plug on the left of there-necked flask is right
Side port dress probe pipe (built-in temperature probe), middle port connects air set pipe and is connected on outside by furnace roof mouth, loads onto a point water respectively
Device (built-in appropriate ethanol), water condensing tube, mix homogeneously, place into electromagnetic agitation, be placed in microwave oven, start stirring,
Mixing speed is 300r/min, starts to react, and releases the water separating in water knockout drum, wherein, microwave oven in course of reaction in time
Microwave irradiation power is 400W, microwave radiation temperature is 130 DEG C, microwave irradiation time is 60min；
Power supply is closed, reaction liquid is poured in the there-necked flask of cleaning and goes out excessive second with vapor distillation after reaction 2h
Alcohol, still residue is poured in clean beaker, cooling crystallization, and being washed with 10% sodium carbonate liquor to pH value is 7.5, sucking filtration,
Use distilled water flushing filter cake, be dried, obtain white solid product ethylparaben.
After measured, the yield of ethylparaben is 92.6%.
Embodiment 2
P-hydroxybenzoic acid, a certain amount of ethanol and sodium bisulfate, P-hydroxybenzoic acid and ethanol is added in there-necked flask
Mol ratio be 1:5；The addition of sodium bisulfate is the 9.6% of P-hydroxybenzoic acid quality, mouth plug grinding port plug on the left of there-necked flask,
Right side mouth dress probe pipe (built-in temperature probe), middle port connects air set pipe and passes through outside furnace roof mouth is connected on, and loads onto respectively point
Hydrophone (built-in appropriate ethanol), water condensing tube, mix homogeneously, place into electromagnetic agitation, be placed in microwave oven, start and stir
Mix, mixing speed is 260r/min, start to react, in course of reaction, release the water separating in water knockout drum, wherein, microwave oven in time
Microwave irradiation power be 600W, microwave radiation temperature be 120 DEG C, microwave irradiation time be 10min；
Power supply is closed, reaction liquid is poured in the there-necked flask of cleaning and goes out excessive second with vapor distillation after reaction 1h
Alcohol, still residue is poured in clean beaker, cooling crystallization, and being washed to pH value with 10% sodium carbonate liquor is 7.5-8.0, takes out
Filter, uses distilled water flushing filter cake, is dried, obtains white solid product ethylparaben.
After measured, the yield of ethylparaben is 90.1%.
Embodiment 3
P-hydroxybenzoic acid, a certain amount of ethanol and sodium bisulfate, P-hydroxybenzoic acid and ethanol is added in there-necked flask
Mol ratio be 1:4；The addition of sodium bisulfate is the 10.2% of P-hydroxybenzoic acid quality, mouth plug ground on the left of there-necked flask
Plug, right side mouth dress probe pipe (built-in temperature probe), middle port connects air set pipe and is connected on outside by furnace roof mouth, loads onto respectively
Water knockout drum (built-in appropriate ethanol), water condensing tube, mix homogeneously, place into electromagnetic agitation, be placed in microwave oven, start and stir
Mix, mixing speed is 200r/min, start to react, in course of reaction, release the water separating in water knockout drum, wherein, microwave oven in time
Microwave irradiation power be 500W, microwave radiation temperature be 128 DEG C, microwave irradiation time be 30min；
Power supply is closed, reaction liquid is poured in the there-necked flask of cleaning and goes out excessive second with vapor distillation after reaction 2.5h
Alcohol, still residue is poured in clean beaker, cooling crystallization, and being washed with 10% sodium carbonate liquor to pH value is 8.0, sucking filtration,
Use distilled water flushing filter cake, be dried, obtain white solid product ethylparaben.
After measured, the yield of ethylparaben is 95.3%.
The above-mentioned description to embodiment is to be understood that for ease of those skilled in the art and apply this
Bright.Person skilled in the art obviously easily can make various modifications to case study on implementation, and described herein one
As principle be applied in other embodiment without through performing creative labour.Therefore, the invention is not restricted to enforcement case here
Example, according to the announcement of the present invention, the improvement made without departing from scope and modification all should be for those skilled in the art
Within protection scope of the present invention.
Claims (5)
1. a kind of preparation method of ethylparaben is it is characterised in that comprise the following steps：
(1) add P-hydroxybenzoic acid, a certain amount of ethanol and sodium bisulfate, mix homogeneously in there-necked flask, place into electromagnetism
Stirrer, is placed in microwave oven, starts stirring, starts to react, and releases the water separating in water knockout drum in course of reaction in time；
(2) close power supply after reaction 1-2.5h, reaction liquid is poured in the there-necked flask of cleaning and is gone out with vapor distillation excessive
Ethanol, still residue is poured in clean beaker, cooling crystallization, and being washed to pH value with 10% sodium carbonate liquor is 7.5-8.0,
Sucking filtration, uses distilled water flushing filter cake, is dried, obtains white solid product ethylparaben.
2. the preparation method of ethylparaben according to claim 1 is it is characterised in that in described step (1)
P-hydroxybenzoic acid is 1 with the mol ratio of ethanol:3-5.
3. the preparation method of ethylparaben according to claim 1 is it is characterised in that in described step (1)
The addition of sodium bisulfate is the 9-10.2% of P-hydroxybenzoic acid quality.
4. the preparation method of ethylparaben according to claim 1 is it is characterised in that in described step (1)
Mixing speed is 200-300r/min.
5. the preparation method of ethylparaben according to claim 1 is it is characterised in that in described step (1)
The microwave irradiation power of microwave oven is 400-600W, microwave radiation temperature is 120-130 DEG C, microwave irradiation time is 10-
60min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610768164.8A CN106397193A (en) | 2016-08-30 | 2016-08-30 | Preparation method of ethyl paraben |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610768164.8A CN106397193A (en) | 2016-08-30 | 2016-08-30 | Preparation method of ethyl paraben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106397193A true CN106397193A (en) | 2017-02-15 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610768164.8A Pending CN106397193A (en) | 2016-08-30 | 2016-08-30 | Preparation method of ethyl paraben |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106397193A (en) |
-
2016
- 2016-08-30 CN CN201610768164.8A patent/CN106397193A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| 照那斯图: "硫酸氢钠催化合成对羟基苯甲酸乙酯", 《化学研究》 * |
| 隆金桥等: "高压微波催化合成对羟基苯甲酸乙酯", 《化工技术与开发》 * |
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