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Dipropyl phthalic ester hapten derivant and its preparation method

A technology of dipropyl phthalate and nitrodipropyl phthalate, which is applied in the field of dipropyl phthalate hapten derivatives and its preparation, can solve the problems that do not involve dipropyl phthalate Ester hapten derivatives, whole antigens and immunoassays, etc., to achieve the effect of simple synthesis and high purity

Inactive Publication Date: 2006-04-26
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no reports on hapten derivatives, whole antigens and immunoassays of dipropyl phthalate in the literature

Method used

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  • Dipropyl phthalic ester hapten derivant and its preparation method
  • Dipropyl phthalic ester hapten derivant and its preparation method
  • Dipropyl phthalic ester hapten derivant and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis of 4-Nitrodipropylphthalate (Step A)

[0051] Add n-propanol to 4-nitrophthalic acid, the ratio of the two substances is 1:6, add concentrated H under stirring condition 2 SO 4 Catalytic, 4-nitrophthalic acid with concentrated H 2 SO 4 The ratio of the amount of the substance is 1:0.6. After stirring and refluxing at 110° C. for 7 hours, unreacted propanol and generated water are distilled off. Pour into ice water while hot, and use 10% Na 2 CO 3 After washing until the water layer was colorless (pH = 7-8), recrystallization with absolute ethanol gave a yellow oily liquid with a yield of Y = 88%.

[0052] UV: λ 1 =214nm,λ 2 = 258nm.

[0053] IR (KBr, υ): 1529, 1357 (-NO 2 ), 1735 (C=O), 1281, 1128 (C-O-C), 2968 (-CH 3 ), 2875 (-CH 3 ), 1430 (δ-OCH 2 -), 1611 (C=C) cm -1 .

[0054] 1 H NMR (300MHz, CDCl 3 ): δ8.56(d, 1H, ArH), 8.35(dd, 1H, ArH), 7.82(d, 1H, ArH), 4.30(t, 2H, OCH 2 CH 2 CH 3 ), 4.26(t, 2H, OCH 2 CH 2 CH 3 ), 1.82-1.77 (m, 2...

Embodiment 2

[0061] Synthesis of 4-Nitrodipropylphthalate (Step A)

[0062] Add n-propanol to 4-nitrophthalic acid, the ratio of the two substances is 1:3, add dry HCl to catalyze under stirring conditions, the amount of substances between 4-nitrophthalic acid and dry HCl The ratio of the mixture was 1:0.3, and after stirring and refluxing at 100°C for 20 hours, unreacted propanol and generated water were distilled off. Pour it into cold water at 5°C while it is hot, and use 10% Na 2 CO 3 After washing until the water layer was colorless (pH = 7-8), recrystallization with absolute ethanol gave a yellow oily liquid with a yield of Y = 83%. UV: λ 1 =214nm,λ 2 = 258nm. IR (KBr, υ): 1528, 1356 (-NO 2 ), 1735 (C=O), 1281, 1128 (C-O-C), 2968 (-CH 3 ), 2875 (-CH 3 ), 1430 (δ-OCH 2 -), 1612 (C=C) cm -1 ;

[0063] Synthesis of dipropyl 4-aminophthalate (step B)

[0064] 4-Nitrodipropyl phthalate is dissolved in benzene, and pure iron powder is added, and the ratio of substances between ...

Embodiment 3

[0066] Synthesis of 4-Nitrodipropylphthalate (Step A)

[0067] Add n-propanol to 4-nitrophthalic acid, the ratio of the two substances is 1:10, add concentrated H under stirring condition 2 SO 4 Catalytic, 4-nitrophthalic acid with concentrated H 2 SO 4 The ratio of the amount of the substance is 1:0.9. After stirring and refluxing at 180° C. for 5 hours, unreacted propanol and generated water are distilled off. Pour it into cold water at 0°C while it is hot, and use 10% Na 2 CO 3 After washing until the water layer was colorless (pH = 7-8), recrystallization with absolute ethanol gave a yellow oily liquid with a yield of Y = 85%. UV: λ 1 =214nm,λ 2 = 258nm. IR (KBr, υ): 1531, 1358 (-NO 2 ), 1735 (C=O), 1280, 1129 (C-O-C), 2968 (-CH 3 ), 2875 (-CH 3 ), 1430 (δ-OCH 2 -), 1610 (C=C) cm -1 .

[0068] Synthesis of dipropyl 4-aminophthalate (step B)

[0069] 4-Nitrodipropylphthalate is dissolved in petroleum ether, and pure magnesium powder is added, and the ratio of...

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Abstract

The dipropyl phthalate half-antigen derivative has the structure as shown and the preparation process disclosed. The preparation process includes the following steps: A. esterification reaction of 4-nitro phthalic acid and n-propanol under acid condition to obtain one kind of dipropyl phthalate half-antigen derivative; and B. reaction of the dipropyl phthalate half-antigen derivative and reductant under acid condition to obtain one other kind of dipropyl phthalate half-antigen derivative. The preparation process is simple, and the product has high purity and may be used in preparing antigen for animal vaccine.

Description

technical field [0001] The present invention relates to a hapten derivative of dipropyl phthalate and a preparation method thereof, in particular to a 4-nitrophthalic acid derivative obtained by esterification reaction of 4-nitrophthalic acid and n-propanol. A method in which dipropyl phthalate and 4-nitrophthalate dipropyl are obtained through reduction reaction to obtain 4-aminodipropyl phthalate. Background technique [0002] Since March 1996, with the preface written by American Vice President Al Gore, the book "Our Stolen Future" written by American scholar Dr. Theo Colborn (Theo Colborn) first proposed environmental hormones (Environmental endocrine disruptors) and Since its impact on the environment, the types of environmental endocrine disrupting substances and their hazards to human health and their mechanism of action have attracted great attention from the academic circles and the public, as well as the governments of developed countries, WHO and other institution...

Claims

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Application Information

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IPC IPC(8): C07C229/62C07C227/04
Inventor 庄惠生张明翠
Owner DONGHUA UNIV
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