Bisphenol 2 (m-amino p-hydroxy phenyl) ether hydrochloride and preparation method and application thereof

A technology of nitro-p-hydroxyhalobenzene and nitro-p-hydroxyhalobenzene, which is applied in the field of monomers and preparations of benzoxazole polymers, and can solve problems such as poor practicability and increased cost

Active Publication Date: 2014-03-26
四川东材绝缘技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the price of 1,4-cyclohexanedicarboxylic acid is as high as 50,000 yuan / ton, which is more than 5 times the price of terephthalic acid (8,000-10,000 yuan / ton), which greatly increases the cost and poor practicability

Method used

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  • Bisphenol 2 (m-amino p-hydroxy phenyl) ether hydrochloride and preparation method and application thereof
  • Bisphenol 2 (m-amino p-hydroxy phenyl) ether hydrochloride and preparation method and application thereof
  • Bisphenol 2 (m-amino p-hydroxy phenyl) ether hydrochloride and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0215] Step Ⅰ: Preparation of m-nitro-p-hydroxyhalobenzene (Example 1)

[0216] Embodiment 1: Synthesis of 3-nitro-4-hydroxychlorobenzene

[0217] Put 152.62g (1.188mol) of p-hydroxychlorobenzene in the reaction bottle, add 1500ml of dichloromethane to dissolve, cool to 0°C under stirring, add 126.74g of concentrated nitric acid (65%, 1.308mol) dropwise, and control the temperature below 5°C , after the dropwise addition was completed, the temperature was controlled below 5°C and stirred for 3 hours. 1500ml of water was washed twice, 500ml of methanol was added, dichloromethane was distilled off, and 180.51g of pure 3-nitro-4-hydroxychlorobenzene was obtained by suction filtration, a yellow powder with a yield of 87.6%.

[0218] The structure is characterized as follows: Infrared spectrum (KBr, cm －1 ) 3421, 3064, 1537, 1473, 1335, 1291, 1222, 818; elemental analysis (%): theoretical value: C: 41.52, H: 2.32, N: 8.07; measured value: C: 41.57, H: 2.30, N :8.12; 1 HNMR: (CD...

Embodiment 2

[0220] Embodiment 2: Synthesis of 3-nitro-4-benzyloxychlorobenzene

[0221] 126.34 g (0.726 mol) of 3-nitro-4-hydroxychlorobenzene was placed in a reaction flask, and 1000 ml of acetonitrile was added. After dissolution, 124.58 g (0.903 mol) of potassium carbonate, 92.46 g of benzyl chloride (0.730 mol) and 10.39 g of potassium iodide (0.0626 mol) were added under stirring, and heated to reflux for 2 hours. After cooling, distill off acetonitrile, add 1000ml of water, stir for 45min, filter with suction, and wash twice with 1000ml of water to obtain a crude product. The crude product was recrystallized from ethanol to obtain 178.24 g of pure 3-nitro-4-benzyloxychlorobenzene as yellow crystals, with a yield of 93.0%.

[0222] The structure is characterized as follows: Infrared spectrum (KBr, cm －1 ) 3092, 3029, 2866, 1611, 1567, 1529, 1481, 1454, 1342, 1301, 1264, 1225, 1132, 1018, 859, 814, 747, 706; elemental analysis (%): theoretical value: C: 59.22, H: 3.82, N: 5.31; mea...

Embodiment 3

[0224] Example 3: Synthesis of 2,2-bis(4-(3-nitro-4-benzyloxyphenoxy)phenyl)propane

[0225] 30.90g (0.117mol) of 3-nitro-4-benzyloxychlorobenzene, 13.33g (0.0585mol) of bisphenol A, 17.14g (0.124mol) of potassium carbonate, and 1.17g (0.0118mol) of cuprous chloride Put it in a reaction flask, and add 150ml of N-methylpyrrolidone. Stir under the protection of nitrogen, and heat to 150 ° C for 18 hours. After cooling, pour it into 1200ml of water, stir for 10 minutes, then filter with suction, wash twice with 400ml of water to obtain a crude product. The crude product was recrystallized with a mixed solvent of ethyl acetate and n-hexane to obtain 28.61g of pure 2,2-bis(4-(3-nitro-4-benzyloxyphenoxy)phenyl)propane, yellow powder , yield 71.6%.

[0226] The structure is characterized as follows: Infrared spectrum (KBr, cm －1 ) 3074, 2820, 1568, 1534, 1471, 1361, 1255, 1139, 1016, 852, 803, 759, 714; element analysis (%): theoretical value: C: 72.13, H: 5.02, N: 4.10; measured...

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Abstract

The invention discloses bisphenol 2 (m-amino p-hydroxy phenyl) ether hydrochloride such as 2,2-2(4-(3-amino-4-hydroxy phenoxy)phenyl) propane hydrochloride and a preparation method and an application of the bisphenol 2 (m-amino p-hydroxy phenyl) ether hydrochloride. The preparation method comprises the steps: nitrating p-hydroxy halogen benzene to obtain m-nitro p-hydroxy halogen benzene, protecting hydroxyl by benzyl, coupling the hydroxyl with a bisphenol agent to obtain ether, removing benzyl by means of hydrogenation and reduction and reducing nitryl into amino, and finally using hydrochloric acid to perform salifying to obtain the bisphenol 2 (m-amino p-hydroxy phenyl) ether hydrochloride. The compound provided by the invention is particularly suitable for the preparation of soluble polybenzoxazol, and the prepared polybenzoxazol has the characteristics of high strength and solubility in the common organic solvent, the defects of insolubility and difficulty in processing of the existing polybenzoxazol polymer are overcome, and the bisphenol 2 (m-amino p-hydroxy phenyl) ether hydrochloride can also be used for the preparation of polyamide and polyimide.

Description

technical field [0001] The invention belongs to monomers of benzoxazole polymers and a preparation method thereof, and relates to bisphenol bis(m-amino p-hydroxyphenyl) ether hydrochloride, a preparation method and application thereof. The bisphenol bis(m-amino p-hydroxyphenyl) ether hydrochloride provided by the invention is especially suitable for synthesizing polybenzoxazole, and can also be used for the preparation of polyamide and polyimide. Background technique [0002] Since the 1980s, benzoxazole polymers have attracted extensive attention and research due to their excellent mechanical, thermal properties and chemical stability. Among them, the most representative poly-p-phenylene benzobisoxazole (PBO) is a polymer with high strength and excellent heat resistance and flame retardancy. Its tensile strength can reach 5.8GPa, modulus can reach 300GPa, thermal decomposition temperature can reach 650℃, and LOI can reach 68. However, because PBO molecules are rigid rod-s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/90C07C213/08C07C317/22C07C315/04C08G73/22
Inventor 唐安斌张前锋黄杰杨玉川
Owner 四川东材绝缘技术有限公司
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