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Pentamethylenediamine succinate and crystal thereof

A technology of pentamethylenediamine succinate and succinic acid, which is applied in the preparation of carboxylate, carboxylate, and organic compounds, etc., which can solve the problem of easy coalescence of oil precipitation, difficulty in obtaining high-quality crystals, and the impact of Questions about the purity of pentamethylenediamine itself

Active Publication Date: 2019-01-11
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The best monomer for synthesizing nylon 54 is high-quality pentamethylenediamine succinic acid crystal salt. However, during the experiment, it was found that pentamethylenediamine and succinic acid are prone to coalescence and oil precipitation during the reaction crystallization process, making it difficult to obtain High-quality crystals, therefore, the raw materials for the synthesis of nylon 54 are still pentamethylenediamine and succinic acid
In this way, the problems brought are: (1) pentamethylenediamine exists in the form of a colorless viscous liquid at normal temperature and pressure, has a pungent odor, and easily absorbs carbon dioxide and moisture in the air to generate pentamethylenediamine carbonic acid Salt, which affects the purity of pentamethylenediamine itself
It brings great inconvenience to the working environment in the transportation, storage and use process; (2) the purity of raw materials is not enough, and high-quality and high-purity crystalline monomer salt is the key factor for preparing high-performance nylon 54

Method used

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  • Pentamethylenediamine succinate and crystal thereof
  • Pentamethylenediamine succinate and crystal thereof
  • Pentamethylenediamine succinate and crystal thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Add 15.00 g of pentamethylenediamine into 100 mL of ethanol aqueous solution with a volume fraction of 90%, and fully stir to form an aqueous solution of pentamethylenediamine in ethanol. Add 15.00g of succinic acid solid to 350mL of 95% ethanol aqueous solution by volume fraction to form succinic acid ethanol aqueous solution, then mix the two in a 500mL crystallizer, keep stirring at 50°C for 2h, and then rapidly cool down To 10°C, add 0.5g seed crystal, and keep stirring for 48h, a white crystal substance appears, put it into the tank, filter it with suction, wash the solid with 100mL methanol, then dry the solid in vacuum for 10h, and keep the temperature at 45-60°C to get pentamethylenediamine Succinate crystalline powder, the thermogravimetric analysis spectrum of the product is as follows Figure 5 , Figure 6 Shown: The DSC spectrum only has an endothermic peak at 151.69°C, and the TG spectrum shows a weightless step at 151.69°C, indicating that the product beg...

Embodiment 2

[0076] Add 20.00 g of pentamethylenediamine into 100 g of acetone and stir well to form a pentamethylenediamine acetone solution. Dissolve 23.12g of succinic acid in 350g of methanol, drop it into the pentamethylenediamine acetone solution at a flow rate of 1mL / min at 15°C, crystallize while stirring, and monitor the pH changes in the process, and the pH is around 10.3 , add 0.15g of seed crystals, suspend feeding, after growing crystals for 1 hour, drop the remaining succinic acid methanol solution into the crystallization system at a flow rate of 0.2mL / min, and continue stirring for 2 hours after feeding is complete, and put it into the tank. Carry out the solid-liquid separation of the crystal paddle by suction filtration, then wash with 80-100mL of methanol, and then vacuum blow dry at 55°C for 8 hours to obtain pentamethylenediamine succinate crystalline powder, and its powder X-ray pattern is basically as follows: Figure 4 shown. When it is prepared as an aqueous solut...

Embodiment 3

[0078] Dissolve 45.00g of succinic acid in 500g of isopropanol to form a uniform solution of succinic acid in isopropanol, and then transfer it to a 1000mL crystallizer. 30.00 g of pentamethylenediamine was dissolved in 200 mL of 95% acetone-water (acetone accounted for 95% by volume) solution to form an aqueous solution of pentamethylenediamine-acetone. Then the aqueous solution of pentamethylenediamine acetone is dripped in the mode of 2mL / min in the isopropanol solution of succinic acid with pump, when the amount of the substance of pentamethylenediamine added is 20% of the amount of succinic acid substance, Add 0.8g seed crystals, add the remaining pentamethylenediamine acetone aqueous solution at 0.3mL / min, the whole process is carried out under stirring, the temperature is controlled at 30°C, and when the feeding is complete, the temperature is lowered to 5°C at a rate of 2°C / h. ℃, the crystallization is completed, and the tank is used for solid-liquid separation, and th...

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Abstract

The invention discloses a pentamethylenediamine succinate, a crystal thereof, and a preparation method of the crystal. The pentamethylenediamine succinate is a salt, being a solid at normal temperature, formed by combining pentanediamine divalent cations with succinate divalent anions according to a molar ratio of 1:1. The structure of the crystal is C9H20N2O4, the crystal belongs to a monoclinicsystem and has a P2(1) / c space group, a = 1.06508(9) nm, b = 1.45943(13) nm, c = 0.79248(6) nm, alpha = 90.00 DEG, beta = 107.384(3) DEG, gamma = 90.00 DEG, the unit cell volume V is 1.17557(17) nm<3>, and the minimum number Z of asymmetric units in a crystal cell is 4. The preparation method comprises the following steps: crystallizing the pentamethylenediamine succinate from a solution containing dissolved pentanediamine and succinic acid, separating the crystal from the solution, and drying the separated crystal.

Description

technical field [0001] The invention belongs to the technical field of crystallization, and in particular relates to monomer pentamethylenediamine succinate of bio-based nylon 54, its crystal structure, its crystal powder, and its preparation method. Background technique [0002] Nylon (polyamide, PA) is an important textile chemical fiber material. The global PA production is about 6 million tons, and it is growing at a rate of 5.4% per year. It is estimated that the global nylon market will reach 43.7 billion US dollars by 2020. Currently, the monomers used to produce nylon are mainly obtained through chemical processing and are derivatives of fossil resources. With the depletion of fossil resources and the strengthening of people's awareness of environmental protection, bio-based environmentally friendly materials have begun to receive more attention. Ajinomoto Company ferments lysine from plant raw materials through fermentation technology, and uses it as a raw material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/00C07C211/09C07C51/41C07C55/10
CPCC07C51/412C07C55/10C07C209/00C07C211/09C07B2200/13
Inventor 应汉杰李子涵杨朋朋吴菁岚庄伟朱晨杰柳东李明唐成伦陈勇
Owner NANJING TECH UNIV
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