CN109956881A - A kind of benzoyl pentanediamine and its preparation and application - Google Patents
A kind of benzoyl pentanediamine and its preparation and application Download PDFInfo
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- CN109956881A CN109956881A CN201711426167.4A CN201711426167A CN109956881A CN 109956881 A CN109956881 A CN 109956881A CN 201711426167 A CN201711426167 A CN 201711426167A CN 109956881 A CN109956881 A CN 109956881A
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- Prior art keywords
- pentanediamine
- benzoyl
- preparation
- solid
- terephthalate
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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
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/90—Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/09—Diamines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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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 provides a kind of acylates of pentanediamine; pentanediamine is passed through into simple chemical change; acylation reaction occurs with acylating agent, the solid acylate property of generation is stablized, storage and transport convenience; simultaneously; the solid acylate can decompose rapidly in heating, release pentanediamine again, fundamentally prevent the safety problem in the long term storage spoilage problems and storage transport of pentanediamine; method simple economy disclosed in the present invention, is with a wide range of applications.
Description
Technical field
The present invention relates to a kind of acylates of pentanediamine, and in particular to a kind of benzoyl pentanediamine.
Background technique
1,5- pentanediamine (hereinafter referred to as pentanediamine) is diamines substance present in nature, there is the evil of similar ammonia
Stink, abbreviation cadaverine.The substance is inflammable, high poison, has strong and stimulating.It can be because of larynx, bronchial spasm, inflammation and water after sucking
It is swollen, chemical pneumonia or pulmonary edema and it is lethal.Poisoning manifestations have cough, wheeze, laryngitis, shortness of breath, headache, nausea and vomiting, sternly
It will be dead when weight.Plant-scale pentanediamine production can be carried out using the method for biofermentation at present, in polyamide industry
For important raw materials for production.
In conventional liquid barreled storage and transit link the spoilage problems that change colour, while penta can usually occur for pentanediamine
Diamines is very readily volatilized, is easy explosion and causes biotoxication, endangers Health Status For Workers Exposed safety.Due to the shakiness of pentanediamine
Qualitative and risk, there is an urgent need to provide safe and effective, the low-cost storage of one kind and transportation resources in the industrial production.
Summary of the invention
It is mentioned for pentanediamine existing in the prior art unstable, perishable, easy leakage drawbacks, the present invention such as cause danger
By simple chemical change and acylating agent acylation reaction is occurred for pentanediamine by the acylate for having supplied a kind of pentanediamine, generation
Solid acylate property is stablized, storage and transport convenience, meanwhile, which can decompose rapidly in heating, again
Release pentanediamine.
The present invention is achieved through the following technical solutions:
On the one hand, the present invention provides a kind of benzoyl pentanediamine.
The benzoyl pentanediamine contains following structural formula:
Wherein, R is carbonylic alkoxy, i.e. COO (CH2)n-1CH3, n=1-4
On the other hand, the present invention provides a kind of preparation method of above-mentioned benzoyl pentanediamine, specifically includes the following steps:
Pentanediamine and acylating agent terephthalate are dissolved in solvent, under the action of catalyst, temperature rising reflux reaction,
Generate solid phase benzoyl pentanediamine, filtering, washing.
Heretofore described terephthalate is dimethyl terephthalate (DMT), diethyl terephthalate, terephthaldehyde
Any one or a few in sour dipropyl, dibutyl terephthalate.
Heretofore described solvent is the mixed solvent of paraxylene, toluene, any one and methanol in ortho-xylene,
Mixed volume ratio is 20~40:1, preferably 20~25:1.
Heretofore described catalyst is lithium methoxide, sodium methoxide, any one or a few in sodium ethoxide, and additional amount is
The 0.05%-0.1% of the quality of pentanediamine.
Heretofore described heating is temperature programming, is heated to 65 DEG C from room temperature, then with 5-10 DEG C/be heated to per hour
80-100℃。
The molar ratio of heretofore described pentanediamine and terephthalate is 1:2, and the mass fraction of solution is after mixing
30%-60%.
By taking dimethyl terephthalate (DMT) as an example, chemical reaction process involved in heretofore described pentanediamine acylation reaction
It is as shown below:
On the other hand, the present invention provides a kind of application of above-mentioned benzoyl pentanediamine.
The application of heretofore described benzoyl pentanediamine is that pentanediamine progress acylation reaction is converted into solid benzoyl
Pentanediamine is stored and/or is transported.
Further, the application of heretofore described benzoyl pentanediamine is by solid benzoyl when using pentanediamine
Pentanediamine heat resolve, releases pentanediamine.
The heat resolve temperature of heretofore described solid benzoyl pentanediamine be 100~200 DEG C, preferably 150~180
℃。
The hygroscopicity that heretofore described benzoyl pentanediamine has had, under normal temperature conditions, benzoyl pentanediamine can
To absorb the moisture in air.Solid benzoyl pentanediamine is heated, the inverse of acylation reaction can occur under water existence condition
Reaction, solid benzoyl pentanediamine resolve into generation pentanediamine.
By taking dimethyl terephthalate (DMT) as an example, chemical reaction process involved in above-mentioned reaction is as shown below:
Dangerous material pentanediamine is transformed into the stable solid compounds of chemical property by chemical reaction in the present invention
Benzoyl pentanediamine, is used as in the storage and transport of pentanediamine, and the long term storage for fundamentally having prevented pentanediamine is rotten
Safety problem in problem and storage transport, since pentanediamine is sufficiently expensive, which can with respect to for its value
To ignore, method simple economy disclosed in the present invention is with a wide range of applications.
Detailed description of the invention
Fig. 1 is the nuclear magnetic spectrogram of the benzoyl pentanediamine generated in embodiment 1.
Specific embodiment
Below by way of specific embodiment, further description of the technical solution of the present invention.
Nuclear magnetic resonance Brooker ultrashield 400plus Nuclear Magnetic Resonance in the present invention, solvent DMSO are differentiated
Rate is 400MHz.
Embodiment 1
2mol dimethyl terephthalate (DMT) and 1mol pentanediamine dissolve in 850ml toluene and 40ml methanol mixed solvent,
0.1g lithium methoxide is added, after being warming up to 65 DEG C, heated up 5 DEG C every 1 hour, stops reaction after keeping the temperature 2 hours to 80 DEG C.Cross drainage
It washes precipitating post package to save, solid can be stablized storage 2 years or more, and there is no Yellowing and weightlessness.Penta need to be used
When diamines, solid is heated at 200 DEG C, pentanediamine will discharge rapidly, and discharge and finish in about 10 minutes, and release gas is with enough
Dilution heat of sulfuric acid absorbs, and it is 99g, pentanediamine release rate 97% that it is of poor quality, which to weigh absorption bottle front and back,.
Embodiment 2
2mol diethyl terephthalate and 1mol pentanediamine are molten in 800ml paraxylene and 29ml methanol mixed solvent
0.1g sodium methoxide is added in solution, after being warming up to 65 DEG C, heats up 7 DEG C every 1 hour, stops reaction after keeping the temperature 1 hour to 90 DEG C.It crosses
It filters water washing and precipitating post package to save, filtrate recycling is reused, and solid can be stabilized 2 years or more, and it is existing that there is no xanthochromias
As and weightlessness.When need to use pentanediamine, solid is heated at 150 DEG C, pentanediamine will discharge rapidly, and release in 10 minutes
Finish.It discharges gas to be absorbed with enough dilution heat of sulfuric acid, it is 90g, pentanediamine release rate 88% that it is of poor quality, which to weigh absorption bottle front and back,.
Embodiment 3
2mol dibutyl terephthalate and 1mol pentanediamine are molten in 850ml paraxylene and 22ml methanol mixed solvent
0.1g sodium ethoxide is added in solution, after being warming up to 65 DEG C, heats up 5 DEG C every 1 hour, stops reaction after keeping the temperature 1.5 hours to 85 DEG C.
It filters water washing and precipitating post package to save, filtrate recycling is reused, and solid can be stabilized 2 two years or more, and there is no Huangs
Cash as and weightlessness.When need to use pentanediamine, solid is heated at 100 DEG C, pentanediamine will discharge rapidly, in 150 minutes
Release finishes.It discharges gas to be absorbed with enough dilution heat of sulfuric acid, it is 51g, pentanediamine release that it is of poor quality, which to weigh absorption bottle front and back,
Rate 50%.
Embodiment 4
2mol dimethyl terephthalate (DMT) and 1mol pentanediamine are molten in 850ml paraxylene and 35ml methanol mixed solvent
0.5g sodium ethoxide is added in solution, after being warming up to 65 DEG C, heats up 5 DEG C every 1 hour, stops reaction after keeping the temperature 2 hours to 80 DEG C.It crosses
It filters water washing and precipitating post package to save, filtrate recycling is reused, and solid can be stabilized 2 years or more, and it is existing that there is no xanthochromias
As and weightlessness.When need to use pentanediamine, solid is heated at 180 DEG C, pentanediamine will discharge rapidly, and release in 10 minutes
Finish.It discharges gas to be absorbed with enough dilution heat of sulfuric acid, it is 99g, pentanediamine release rate 97% that it is of poor quality, which to weigh absorption bottle front and back,.
Embodiment 5
2mol dimethyl terephthalate (DMT) and 1mol pentanediamine are molten in 850ml paraxylene and 42ml methanol mixed solvent
0.1g sodium ethoxide is added in solution, after being warming up to 65 DEG C, heats up 10 DEG C every 1 hour, stops reaction after keeping the temperature 1 hour to 100 DEG C.
It filters water washing and precipitating post package to save, filtrate recycling is reused, and solid can be stabilized 2 years or more, and there is no xanthochromias
Phenomenon and weightlessness.When need to use pentanediamine, solid is heated at 180 DEG C, pentanediamine will discharge rapidly, and discharge in 10 minutes
It finishes.It discharges gas to be absorbed with enough dilution heat of sulfuric acid, it is 100g, pentanediamine release rate that it is of poor quality, which to weigh absorption bottle front and back,
98%.
Claims (10)
1. a kind of benzoyl pentanediamine, which is characterized in that the benzoyl pentanediamine contains following structural formula:
Wherein, R is carbonylic alkoxy, i.e. COO (CH2)n-1CH3, n=1-4.
2. a kind of preparation method of benzoyl pentanediamine as described in claim 1, which is characterized in that the preparation method is specific
The following steps are included:
Pentanediamine and acylating agent terephthalate are dissolved in solvent, under the action of catalyst, temperature rising reflux reaction generates
Solid phase benzoyl pentanediamine, filtering, washing.
3. the preparation method of benzoyl pentanediamine according to claim 2, the terephthalate is terephthalic acid (TPA)
Dimethyl ester, diethyl terephthalate, terephthalic acid (TPA) dipropyl, any one or a few in dibutyl terephthalate.
4. the preparation method of benzoyl pentanediamine according to claim 2 or 3, the solvent is paraxylene, toluene, neighbour
The mixed solvent of any one and methanol in dimethylbenzene, mixed volume ratio are 20~40:1, preferably 20~25:1.
5. the catalyst is lithium methoxide, first according to the preparation method of the described in any item benzoyl pentanediamines of claim 2-4
Any one or a few in sodium alkoxide, sodium ethoxide, additional amount are the 0.05-0.1% of the quality of pentanediamine.
6. according to the preparation method of the described in any item benzoyl pentanediamines of claim 2-5, the heating is temperature programming, from
Room temperature is heated to 65 DEG C, then with 5-10 DEG C/be heated to 80-100 DEG C per hour.
7. according to the preparation method of the described in any item benzoyl pentanediamines of claim 2-6, the pentanediamine and terephthaldehyde
The molar ratio of acid esters is 1:2, and the mass fraction of solution is 30%-60% after mixing.
8. a kind of application of benzoyl pentanediamine as described in claim 1, which is characterized in that benzoyl pentanediamine is used as penta
The storage and/or transport of diamines.
9. pentanediamine progress acylation reaction is converted into solid benzene by the application of benzoyl pentanediamine according to claim 8
Formyl pentanediamine, by solid benzoyl pentanediamine heat resolve, releases pentanediamine when using pentanediamine.
10. the application of benzoyl pentanediamine according to claim 9, the heat resolve temperature of the solid benzoyl pentanediamine
Degree is 100~200 DEG C, preferably 150~180 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711426167.4A CN109956881A (en) | 2017-12-26 | 2017-12-26 | A kind of benzoyl pentanediamine and its preparation and application |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711426167.4A CN109956881A (en) | 2017-12-26 | 2017-12-26 | A kind of benzoyl pentanediamine and its preparation and application |
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| CN109956881A true CN109956881A (en) | 2019-07-02 |
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| CN201711426167.4A Pending CN109956881A (en) | 2017-12-26 | 2017-12-26 | A kind of benzoyl pentanediamine and its preparation and application |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA991199A (en) * | 1970-10-13 | 1976-06-15 | Luigi Ciceri | Process for preparing monomers useful to the synthesis of regular polyester-amides and polyester-amides obtained thereby |
| GB1596376A (en) * | 1976-12-22 | 1981-08-26 | Smith Kline French Lab | 4,5-disubstituted imidazole-2-thiones processes for their preparation and their use as intermediates |
| US4730006A (en) * | 1986-01-27 | 1988-03-08 | Merrell Dow Pharmaceuticals Inc. | Derivatives of 2,6-diamino-3-haloheptanedioic acid |
-
2017
- 2017-12-26 CN CN201711426167.4A patent/CN109956881A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA991199A (en) * | 1970-10-13 | 1976-06-15 | Luigi Ciceri | Process for preparing monomers useful to the synthesis of regular polyester-amides and polyester-amides obtained thereby |
| GB1596376A (en) * | 1976-12-22 | 1981-08-26 | Smith Kline French Lab | 4,5-disubstituted imidazole-2-thiones processes for their preparation and their use as intermediates |
| US4730006A (en) * | 1986-01-27 | 1988-03-08 | Merrell Dow Pharmaceuticals Inc. | Derivatives of 2,6-diamino-3-haloheptanedioic acid |
Non-Patent Citations (1)
| Title |
|---|
| SEIJI SHINKAI等: "Organogels of 8-Quinolinol/Metal(II)–Chelate Derivatives That Show Electron- and Light-Emitting Properties", 《CHEM. EUR. J.》 * |
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Address after: 4 / F, building 5, No. 1690, Cailun Road, free trade zone, Pudong New Area, Shanghai Applicant after: CATHAY R&D CENTER Co.,Ltd. Applicant after: CATHAY INDUSTRIAL BIOTECH Ltd. Address before: 200120 Shanghai Zhangjiang High Tech Park of Pudong New Area Cailun Road No. 5 No. 1690 Applicant before: CATHAY R&D CENTER Co.,Ltd. Applicant before: CATHAY INDUSTRIAL BIOTECH Ltd. |
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Effective date of registration: 20191029 Address after: 4 / F, building 5, No. 1690, Cailun Road, free trade zone, Pudong New Area, Shanghai Applicant after: CATHAY R&D CENTER Co.,Ltd. Applicant after: CIBT USA Address before: 201203 floor 4, building 5, No. 1690, Cailun Road, free trade zone, Pudong New Area, Shanghai Applicant before: CATHAY R&D CENTER Co.,Ltd. Applicant before: CATHAY INDUSTRIAL BIOTECH Ltd. |
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| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190702 |