CN109516922B - Post-treatment method of N, N' -dicyclohexylcarbodiimide residue - Google Patents
Post-treatment method of N, N' -dicyclohexylcarbodiimide residue Download PDFInfo
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- CN109516922B CN109516922B CN201811405312.5A CN201811405312A CN109516922B CN 109516922 B CN109516922 B CN 109516922B CN 201811405312 A CN201811405312 A CN 201811405312A CN 109516922 B CN109516922 B CN 109516922B
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- cyclohexylamine
- dcc
- residue
- dicyclohexylcarbodiimide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a post-treatment method of N, N' -dicyclohexylcarbodiimide residue, which takes DCC residue as a starting material, controls the vacuum to be about 0.01Mpa, heats up to about 110 ℃, adds caustic soda flakes, preserves the temperature for 4-5 hours, heats up to 130-150 ℃ and carries out reduced pressure distillation treatment to obtain cyclohexylamine liquid. According to the invention, DCC residues are treated by caustic soda flakes and then subjected to reduced pressure distillation to obtain cyclohexylamine, the content of the synthesized cyclohexylamine is over 90 percent, and the synthesized cyclohexylamine can be directly used as a DCC one-step raw material, so that the cost is saved; after treatment, 70% of hazardous waste can be reduced, and the pollution to the environment is greatly reduced.
Description
Technical Field
The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a post-treatment method of N, N' -dicyclohexylcarbodiimide residue.
Background
N, N' -Dicyclohexylcarbodiimide (DCC) is a good low-temperature biochemical dehydrating agent, is used for synthesizing and dehydrating amikacin and amino acid, is also used for synthesizing acid, anhydride, aldehyde, ketone and the like, and is also used for synthesizing peptide and nucleic acid. DCC dehydration condensation is adopted, the reaction condition is mild, and the synthesis yield is high, so that the DCC dehydration condensation is often used as a dehydrating agent or a carboxyl activating agent for polypeptide synthesis or for coupling of small molecular compounds and polypeptides with carrier proteins.
At present, DCC residues are obtained from DCC mother liquor generated in the production process of the product after treatment. The residue mainly contains DCC, DCU, tricyclohexylguanidine, cyclohexyl isothiocyanate and the like, cannot be treated, can be treated only as dangerous waste, and has high treatment cost and serious environmental pollution.
Disclosure of Invention
The invention aims to provide a post-treatment method of N, N' -dicyclohexylcarbodiimide residues, which reduces the number of hazardous wastes and reduces the cost.
The technical scheme adopted by the invention for solving the technical problems is as follows: a post-treatment method of N, N' -dicyclohexylcarbodiimide residue comprises the following steps: DCC residue is taken as a starting material, the vacuum is controlled to be about 0.01Mpa, the temperature is raised to about 110 ℃, caustic soda flakes are added, the temperature is kept for 4 to 5 hours, the temperature is raised to 130-150 ℃, and the reduced pressure distillation treatment is carried out, so as to obtain the cyclohexylamine liquid.
Specifically, the dosage of the caustic soda flakes is 15-25% of the total mass of the materials, and is preferably 20%.
Specifically, the cyclohexylamine content in the cyclohexylamine liquid is more than 90%, and the cyclohexylamine liquid can be directly used as a DCC product raw material.
The invention has the following beneficial effects: according to the invention, DCC residues are treated by caustic soda flakes and then subjected to reduced pressure distillation to obtain cyclohexylamine, the content of the synthesized cyclohexylamine is over 90 percent, and the synthesized cyclohexylamine can be directly used as a DCC one-step raw material, so that the cost is saved; after treatment, 70% of hazardous waste can be reduced, and the pollution to the environment is greatly reduced.
Detailed Description
The following are specific examples of the present invention and further describe the technical solutions of the present invention, but the scope of the present invention is not limited to these examples. All changes, modifications and equivalents that do not depart from the spirit of the invention are intended to be included within the scope thereof.
Example 1
A post-treatment method of N, N' -dicyclohexylcarbodiimide residue comprises the following steps: DCC residues are used as a starting material, the vacuum is controlled to be about 0.01Mpa, flake caustic soda accounting for 20 percent of the total material mass is added when the temperature is raised to about 110 ℃, the temperature is kept for 5 hours, the temperature is raised to 140 ℃, and reduced pressure distillation treatment is carried out to obtain cyclohexylamine liquid, wherein the cyclohexylamine content in the cyclohexylamine liquid is more than 92.5 percent, and the cyclohexylamine liquid can be directly used as a DCC product raw material.
Example 2
A post-treatment method of N, N' -dicyclohexylcarbodiimide residue comprises the following steps: DCC residues are used as a starting material, the vacuum is controlled to be about 0.01Mpa, the temperature is raised to about 110 ℃, flake caustic soda accounting for 15 percent of the total material mass is added, the temperature is kept for 4 hours, the temperature is raised to 150 ℃, and reduced pressure distillation treatment is carried out, so that cyclohexylamine liquid is obtained, the cyclohexylamine content in the cyclohexylamine liquid is more than 91.7 percent, and the liquid can be directly used as a DCC product raw material.
Example 3
A post-treatment method of N, N' -dicyclohexylcarbodiimide residue comprises the following steps: DCC residues are used as starting materials, the vacuum is controlled to be about 0.01Mpa, flake caustic soda accounting for 25% of the total material mass is added when the temperature is raised to about 110 ℃, the temperature is kept for 4.5 hours, then the temperature is raised to 130 ℃, and reduced pressure distillation treatment is carried out, so that cyclohexylamine liquid is obtained, the cyclohexylamine content in the cyclohexylamine liquid is more than 92.5%, and the cyclohexylamine liquid can be directly used as DCC product raw materials.
Example 4
A post-treatment method of N, N' -dicyclohexylcarbodiimide residue comprises the following steps: DCC residues are used as a starting material, the vacuum is controlled to be about 0.01Mpa, flake caustic soda accounting for 18 percent of the total material mass is added when the temperature is raised to about 110 ℃, the temperature is kept for 4.5 hours, the temperature is raised to 145 ℃, and reduced pressure distillation treatment is carried out to obtain cyclohexylamine liquid, wherein the cyclohexylamine content in the cyclohexylamine liquid is more than 92.1 percent, and the cyclohexylamine liquid can be directly used as a DCC product raw material.
Claims (2)
1. A method for post-treating N, N' -dicyclohexylcarbodiimide residue is characterized by comprising the following steps:
taking DCC residues as a starting material, controlling the vacuum to be about 0.01Mpa, heating to about 110 ℃, adding caustic soda flakes, keeping the temperature for 4-5 hours, heating to 130-150 ℃, and carrying out reduced pressure distillation treatment to obtain cyclohexylamine liquid; the dosage of the flake caustic soda is 15-25% of the total mass of the materials; the cyclohexylamine content in the cyclohexylamine liquid is more than 90 percent, and the cyclohexylamine liquid can be directly used as a DCC product raw material.
2. The method for post-treating an N, N' -dicyclohexylcarbodiimide residue according to claim 1, wherein the amount of the caustic soda flakes is 20% by mass of the total mass of the material.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811405312.5A CN109516922B (en) | 2018-11-23 | 2018-11-23 | Post-treatment method of N, N' -dicyclohexylcarbodiimide residue |
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| CN201811405312.5A CN109516922B (en) | 2018-11-23 | 2018-11-23 | Post-treatment method of N, N' -dicyclohexylcarbodiimide residue |
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| CN109516922A CN109516922A (en) | 2019-03-26 |
| CN109516922B true CN109516922B (en) | 2021-09-21 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1424676A (en) * | 1972-08-21 | 1976-02-11 | Kodak Ltd | Process for the preparation of di-secondary-amino-benzenes |
| CN1139649A (en) * | 1995-07-05 | 1997-01-08 | 冯豫川 | Treatment method for the Waste liquid in production of dicyclohexyl diimide carhide (DDC) |
| CN1878744A (en) * | 2004-03-09 | 2006-12-13 | 德古萨公司 | Method for the production of amines from compounds comprising carbodiimide groups, by hydrolysis with water |
| CN105439870A (en) * | 2015-12-05 | 2016-03-30 | 山东汇海医药化工有限公司 | Method for recycling recycled N,N'-dicyclohexylurea |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01165578A (en) * | 1987-12-23 | 1989-06-29 | Chisso Corp | Optically active-2-phenyl-5-alkanoyloxypyrimidine |
| CN100467444C (en) * | 2006-11-29 | 2009-03-11 | 山西医科大学 | 4-azo salicylic acid derivative and process for producing the same and uses |
| US20100221809A1 (en) * | 2008-12-23 | 2010-09-02 | The Regents Of The University Of California | Compositions and Methods for the Isolation of Biologically Active Proteins |
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2018
- 2018-11-23 CN CN201811405312.5A patent/CN109516922B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1424676A (en) * | 1972-08-21 | 1976-02-11 | Kodak Ltd | Process for the preparation of di-secondary-amino-benzenes |
| CN1139649A (en) * | 1995-07-05 | 1997-01-08 | 冯豫川 | Treatment method for the Waste liquid in production of dicyclohexyl diimide carhide (DDC) |
| CN1878744A (en) * | 2004-03-09 | 2006-12-13 | 德古萨公司 | Method for the production of amines from compounds comprising carbodiimide groups, by hydrolysis with water |
| CN105439870A (en) * | 2015-12-05 | 2016-03-30 | 山东汇海医药化工有限公司 | Method for recycling recycled N,N'-dicyclohexylurea |
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| CN109516922A (en) | 2019-03-26 |
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