Pentanediamine ethanedioate and crystal thereof

A technology of pentamethylenediamine oxalate and oxalic acid, which is applied in the field of monomer crystallization of bio-based materials, which can solve the problems of inconvenient transportation and use, affecting the purity of pentamethylenediamine itself, and unpleasant pungent smell

Active Publication Date: 2019-01-25
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Different from hexamethylenediamine, pentamethylenediamine exists as a colorless viscous fuming liquid at normal temperature and pressure, has an unpleasant pungent odor similar to ammonia, is extremely volatile and easily absorbs carbon dioxide in the air to form pentamethylenediamine Diamine carbonate greatly affects the purity of pentamethylenediamine, and compared with solid raw materials, it is relatively inconvenient in transportation and use

Method used

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  • Pentanediamine ethanedioate and crystal thereof
  • Pentanediamine ethanedioate and crystal thereof
  • Pentanediamine ethanedioate and crystal thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Add 10.00 g of pentamethylenediamine into 100 g of ethanol and stir well to form a pentamethylenediamine ethanol solution. Dissolve 8.81g of oxalic acid in 150g of ethanol, drop it into the ethanol solution of pentamethylenediamine at a flow rate of 0.5mL / min at 35°C, crystallize under stirring, and monitor the pH changes in the process, at pH 10.0 Add 0.2g of seed crystals, suspend feeding, and after 2.5 hours of crystal growth, pump the oxalic acid ethanol solution into the crystallization system at a flow rate of 0.2mL / min. Vacuum suction filtration, and wash the filter cake layer with 50-100mL ethanol, and then vacuum blast drying at 70°C for 12 hours to obtain pentamethylenediamine oxalate crystalline powder, which does not contain crystal water, and its powder X-ray diffraction pattern is as follows: Figure 6 As shown, the specific diffraction data are as Figure 11 shown. When the obtained crystalline salt is formulated into an aqueous solution with a mass fra...

Embodiment 2

[0086] Add 10.00 g of pentamethylenediamine into 60 mL of 90% methanol aqueous solution (methanol volume fraction is 90%), and stir well to form an aqueous solution of pentamethylenediamine methanol. Add 8.81g of oxalic acid solid into 250mL of 80% methanol aqueous solution (methanol volume fraction is 90%), form the methanol aqueous solution of oxalic acid, then the two are mixed in 500mL crystallizer, control temperature at 20 ℃, Stir for 56 hours, a white crystal substance appears, put it into the tank, filter it with suction, wash the solid with 60-80mL of 95% ethanol, then dry the solid under vacuum for 8 hours, and keep the temperature at 45-50°C to obtain crystallization of pentamethylenediamine oxalate Powder, containing 3 waters of crystallization, the water content of the powder is 22wt%, the TG analysis spectrum of the product is as follows Figure 7 , Figure 8 Shown: the product starts to melt at 138.58°C, loses water of crystallization at 159.12°C, loses two wat...

Embodiment 3

[0089] Dissolve 26.00 g of pentamethylenediamine in 300 mL of absolute ethanol to form a uniform pentamethylenediamine ethanol solution. Dissolve 20.10 g of oxalic acid in 450 g of 90% methanol-water binary solvent by volume fraction to form a uniform oxalic acid methanol aqueous solution, and then transfer it into a 1000 mL crystallizer. At 45°C, drop into the pentamethylenediamine ethanol solution at a flow rate of 0.8mL / min, carry out crystallization under stirring, and monitor the pH change during the process. After 1.5 hours of crystallization, drop methanol solution of oxalic acid into the crystallization system at a flow rate of 0.5mL / min. Wash with 100-150mL of acetone, and then vacuum-dry at 50°C for 24 hours to obtain pentamethylenediamine oxalate crystalline powder, which contains 2 crystal waters, and the water content of the powder is 15.5wt%. The powder X-ray diffraction pattern is as follows: Figure 5 As shown, the specific diffraction data are as Figure 10 ...

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Abstract

The invention discloses pentanediamine ethanedioate, a crystal thereof and a preparation method thereof. The pentanediamine ethanedioate is a salt which is formed in the manner of combining the divalent cation of pentanediamine with the divalent anion of ethanedioic acid in a mole ratio of 1 to 1 and presents a solid state at normal temperature. The crystal structure of the pentanediamine ethanedioate is C7H16N2O4, belongs to a triclinic system and has a space group P-1; a is equal to 6.849(5) angstroms; b is equal to 9.484(7) angstroms; c is equal to 10.764(8) angstroms; alpha is equal to 110.712(8) degrees; beta is equal to 97.505(8) degrees; gamma is equal to 91.358(8) degrees; the volume V of a crystal cell is equal to 646.5(8) angstroms; and a minimal asymmetric unit number Z in the crystal cell is equal to 2. The preparation method comprises the following steps of crystallizing out the pentanediamine ethanedioate containing crystalline water from a solution containing dissolved pentanediamine and ethanedioic acid, separating out the crystal from the solution, and drying the separated crystal.

Description

technical field [0001] The invention belongs to the technical field of monomer crystallization of bio-based materials, and in particular relates to monomer pentamethylenediamine oxalate of bio-based nylon 52, its crystal structure, its crystal powder, and its preparation method. Background technique [0002] Polyamide is commonly known as nylon (Nylon), and its English name is Polyamide (referred to as PA). It is a general term for thermoplastic resins containing repeated amide groups - [NHCO] - in the main molecular chain. Polyamide is widely used as a substitute for traditional materials such as metal and wood due to its high mechanical strength, high softening point, low friction coefficient, and good heat resistance, wear resistance, chemical corrosion resistance, and self-lubrication. , as various structural materials. At present, the main varieties of nylon are polyamide 6 and polyamide 66, both of which are produced by chemical methods using petroleum as raw material...

Claims

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Application Information

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IPC IPC(8): C07C209/00C07C211/09C07C51/41C07C55/07
CPCC07C51/412C07C55/07C07C209/00C07C211/09C07B2200/13
Inventor 杨朋朋应汉杰李子涵吴菁岚庄伟王森李晓洁黎青青欧阳平凯
Owner NANJING UNIV OF TECH
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