Solvent-free amide synthesis method and its use in synthesis of polymer antioxidant stabilizer
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A synthesis method and technology of solvent amides, which are applied in the field of synthesis and preparation of polymer antioxidant stabilizers, can solve the problems of high cost, achieve the effects of strong resistance to environmental degradation, good synergistic antioxidant performance, and overcoming unstable performance
Inactive Publication Date: 2017-07-04
SHAOXING RUIKANG BIOTECHNOLOGES CO INC
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The general operation steps are to prepare and separate the activated ester first, and then react with the amine to obtain the amide. The two-step reaction requires an effective follow-up separation and purification step of by-products, and the cost is high.
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Embodiment 1
[0074] The reaction equation of monoamine and diamine with methyl ester:
[0075]
[0076] n: natural number;
[0077] R: H, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, t-Bu, long chain alkyl
[0078] RCO 2 Na:HCO 2 Na,CH 3 CO 2 Na et al. In this embodiment, heating control is an important factor. The reaction will turn yellow under high temperature for a long time, and the product quality will decline. Please see the following table for the corresponding reaction conditions: Beta-sulfide methyl ester and monobasic and dibasic organic amines Condensation reaction catalyzed by carboxylate
[0079]
[0080] Note: n.a. means not applicable to this (not applicable)
[0081] Synthetic example methyl acrylate as raw material:
[0082] The first step: Methyl acrylate and mercaptan undergo Michael 1,4-addition reaction under solvent-free carboxylate catalyzed conditions to obtain beta-sulfide methyl ester. The reaction needs to control the temperature, and it is better to stir for a...
Embodiment 2
[0087] Reaction equation of methyl 3,3'-thioether dipropionate with monohydric and dihydric organic amines
[0088]
[0089]
[0090] The preparation method of disulfide adipamide:
[0091] Add Beta-12 alkyl (or 8 alkyl) methyl sulfide propionate (1 equivalent) into the reaction flask, then add sodium formate or sodium acetate catalyst, add hexamethylenediamine (0.45-0.49 equivalent) under nitrogen protection , and then heating up, TLC or GC-MS tracking reaction process, until the reaction is complete. Add ethanol aqueous solution or methanol aqueous solution, recrystallize, and cool and filter to obtain a white solid with a yield of 85-99%.
[0092] A. Product di-12 alkyl-beta-disulfide adipamide m.p.: 133-137℃ Product di-12 alkyl beta-sulfide adipamide 1 The HNMR test was completed in NMR instrument Bruker, 400MHz, 1 H NMR in CD 3 OD(δ,ppm):0.87-0.93(m,6H),1.28-1.35(m,40H),1.35-1.46(m,8H),2.47(t,4),2.55(t,4H),2.78( t,4H),3.23(t,4H),3.33(bm,CH 3 OH in CD 3 OD), 4...
Embodiment 3
[0097] The reaction equation between dimethyl dicarboxylate and organic monoamine or thioether monoamine:
[0098]
[0099] The synthetic conditions of this embodiment:
[0100]
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Abstract
The invention discloses a solvent-free amide synthesis method and its use in synthesis of a polymer antioxidant stabilizer. Through eight reaction expressions, different structural amide-linked thioether high-temperature long-term antioxidant stabilizers, sterically hindered phenol thioether hybrid antioxidants and sterically hindered phenol amide-type antioxidants as desired products are synthesized. Compared with the most carboxylate-bonded antioxidants on the market, the different types of multi-functional hybrid structure antioxidants stably bonding to amide have the advantages of structure stability, acid resistance, base resistance, hydrolysis resistance, environmental degeneration resistance and good synergistic antioxidation activity and are novel antioxidant stabilizer products having performances satisfying novel material development requirements. The novel polymer antioxidant stabilizers solve the problem that the same type of the ester-linked antioxidant stabilizer on the market has an ester bond easily decomposed under acid and base conditions and can be easily hydrolyzed and the existing product DSTDP / DLTDP on the market produces a smell in use and processing and the degraded material releases VOCs. The novel polymer antioxidant stabilizers provide a strong support and more choices for development of novel polymers.
Description
technical field [0001] The invention belongs to the field of synthesis and preparation of polymer antioxidant stabilizers, and in particular relates to a solvent-free amide synthesis method and its application in the synthesis of polymer antioxidant stabilizers. Background technique [0002] At present, the most widely used carboxamide synthesis method in industry is to chlorinate carboxylic acid, and then react with organic amine. The two-step chemical reaction synthesizes carboxamide products. Commonly used acid chloride reagents are SOCl 2 and C 2 o 2 Cl 2 , through the catalysis of DMF or DMAP, the conversion of carboxylic acid chloride is accelerated, and the excess SOCl in the reaction 2 or C 2 o 2 Cl 2 Can unavoidable hydrochloric acid gas generation, and unpleasant acid chloride smell; Next step carboxylic acid chloride can effectively produce carboxamide product with the coupling reaction of organic amine in the presence of necessary excessive or at least qua...
Claims
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