CN109970583A - A kind of production method of P-butylaminobenzoic acid ethyl ester - Google Patents
A kind of production method of P-butylaminobenzoic acid ethyl ester Download PDFInfo
- Publication number
- CN109970583A CN109970583A CN201811395556.XA CN201811395556A CN109970583A CN 109970583 A CN109970583 A CN 109970583A CN 201811395556 A CN201811395556 A CN 201811395556A CN 109970583 A CN109970583 A CN 109970583A
- Authority
- CN
- China
- Prior art keywords
- production method
- ethyl ester
- acid ethyl
- ethylaminobenzoate
- butanal
- 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
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Classifications
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- 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
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of production methods of chemical products P-butylaminobenzoic acid ethyl ester.It is characterized in that selecting ethylaminobenzoate and n-butanal for raw material, high-activity palladium, the catalyst such as platinum, using hydrogen as reducing agent are selected, single step reaction synthesizes target product, and this method has production method simple, and environmental protection is friendly, high income, it is at low cost, meet mass production requirement.
Description
Technical field
The present invention relates to chemical fields: being related to a kind of production method of P-butylaminobenzoic acid ethyl ester.
Background technique
P-butylaminobenzoic acid ethyl ester is a kind of important chemical products, and there are many important applications.Conventional production methods are
It is anti-up to 12 hours by 100 degree of high temperature under the effect of alkaline matter sodium carbonate using ethylaminobenzoate and bromobutane
It answers, crude product is made, qualified products can just be obtained by repeatedly being refined.And production generates a large amount of alkali waste waters, pollutes environment.And it reacts
In process, has a large amount of two by-product is replaced to generate, need to refine repeatedly, cause product yield low, it is at high cost.
Summary of the invention
Present invention aim to address existing production technology there are the problem of, a kind of new production method, production method are provided
Simple possible, environmental-friendly, yield is high, at low cost.
The present invention uses the method to be: using ethylaminobenzoate and n-butanal as raw material, being dissolved in methanol, alcohol solvent
In, using noble metal catalyst palladium, platinum, ruthenium, rhodium, iridium, rhenium.The form of supported catalyst is active carbon, aluminium oxide, silica.
Under 0-100 kilograms of atmospheric pressure of certain temperature 0-200 degree and certain pressure, hydrogen hydrogenating reduction is carried out, single step reaction obtains most
Finished product.Feature is, environmental-friendly, and no alkali waste water discharge, solvent recovery is applied, zero-emission, and nothing is reused in catalyst recycling
Waste, simple production process, single step reaction obtain product.High production efficiency, product yield are at low cost up to 90% or more.Hydrogen comes
Source is convenient, reliable, feasible.
Its optimal selection are as follows: ethylaminobenzoate and n-butanal use equimolar substance dosage.Methanol is the object that feeds intake
Expect 5 times of weight, be added 5% palladium-carbon catalyst, additional amount is to feed intake the 1.5% of weight of material.Production reaction heating is heated to be 55 degree,
Hydrogen Vapor Pressure is 6 kilograms, the reaction time 12 hours.End of reaction is separated off palladium-carbon catalyst, recycles methanol solvate, obtains white
Color product.
Specific embodiment
Example:
16.5 grams of ethylaminobenzoate and 7.2 grams of n-butanals are put into plus hydrogenated reaction kettle, 118.6 grams of methanol are added,
And 0.36 gram of 5% palladium-carbon catalyst, 55 degree are warming up to, pressure is maintained at 6 kilograms, and inputting hydrogen carries out hydrogenation reaction.Reaction
It 12 hours, finishes, depressurizes, cooling filters to isolate palladium-carbon catalyst, and filtrate decompression recycles methanol, is left to obtain white solid, does
It is dry to obtain product 20g, fusing point mp68-69, product yield 90.49%.
Claims (9)
1. a kind of production method of chemical products P-butylaminobenzoic acid ethyl ester, products C AS is 94-32-6.
2. its production method feature is to use ethylaminobenzoate and n-butanal for raw material, using alcohol as solvent, in certain temperature
Under degree and pressure, using high activity noble metal as catalyst, hydrogenation reduction is carried out, the product is made.
3. according to claim 1: be to use ethylaminobenzoate and n-butanal for raw material, put together, directly into
Row hydrogenation reaction, obtains required product.
4. according to claim 1: reaction temperature selects 0-200 degree.
5. pressure selects 0-100 kilograms of atmospheric pressure.
6. according to claim 1: solvent selection methanol, ethyl alcohol and other alcohols solvents.
7. according to claim 1: reduction reaction selects hydrogen, is reacted.
8. according to claim 1: the high palladium of catalyst choice activity, platinum, ruthenium, rhodium, iridium, rhenium.
9. load form is active carbon, aluminium oxide, silica.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811395556.XA CN109970583A (en) | 2018-11-22 | 2018-11-22 | A kind of production method of P-butylaminobenzoic acid ethyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811395556.XA CN109970583A (en) | 2018-11-22 | 2018-11-22 | A kind of production method of P-butylaminobenzoic acid ethyl ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109970583A true CN109970583A (en) | 2019-07-05 |
Family
ID=67076075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811395556.XA Pending CN109970583A (en) | 2018-11-22 | 2018-11-22 | A kind of production method of P-butylaminobenzoic acid ethyl ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109970583A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113649024A (en) * | 2021-08-10 | 2021-11-16 | 北京旋光普利生物医药科技开发有限公司 | Preparation of catalyst for producing ethyl p-butylaminobenzoate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1289764A (en) * | 2000-09-06 | 2001-04-04 | 胡国宜 | Process for preparing ethyl p-dimethylaminobenzoate |
| CN101007773A (en) * | 2007-01-24 | 2007-08-01 | 吴建龙 | Process for preparing ethyl p-dimethylaminobenzoate |
-
2018
- 2018-11-22 CN CN201811395556.XA patent/CN109970583A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1289764A (en) * | 2000-09-06 | 2001-04-04 | 胡国宜 | Process for preparing ethyl p-dimethylaminobenzoate |
| CN101007773A (en) * | 2007-01-24 | 2007-08-01 | 吴建龙 | Process for preparing ethyl p-dimethylaminobenzoate |
Non-Patent Citations (2)
| Title |
|---|
| EUNYOUNG BYUN等: "One-Pot Reductive Mono-N-alkylation of Aniline and Nitroarene Derivatives Using Aldehydes", 《J. ORG. CHEM.》 * |
| 孙智勇主编: "《制药工艺操作与技术改进》", 31 March 1994 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113649024A (en) * | 2021-08-10 | 2021-11-16 | 北京旋光普利生物医药科技开发有限公司 | Preparation of catalyst for producing ethyl p-butylaminobenzoate |
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