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Preparation method of polyalcohol acetal compound

A technology of alcohol acetal and polyol, which is applied in the field of preparation of polyol acetal compounds, can solve the problems of large influence of type and structure, easy production of by-products, poor product selectivity, etc., and achieve wide applicability and route design Novelty and good product purity

Inactive Publication Date: 2018-06-22
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The first method has low yield and poor product selectivity. It is only suitable for the condensation reaction of polyols and some aromatic aldehydes. The reaction conditions are greatly affected by the amount, type and structure of substituted aldehydes, but it is very difficult for the reaction of polyols and aliphatic aldehydes. Less involved; the second method has a higher temperature, requires nitrogen, and constantly replenishes methanol. The operation is troublesome, the post-treatment is more complicated, and by-products are easily produced. The reaction conditions are also greatly affected by the amount, type and structure of substituted aldehydes.

Method used

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  • Preparation method of polyalcohol acetal compound
  • Preparation method of polyalcohol acetal compound
  • Preparation method of polyalcohol acetal compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1,3:2,4-di-o-hydroxyphenylmethylene-D-sorbitol, obtained by condensation of sorbitol and salicylaldehyde, its synthetic route is as follows:

[0029]

[0030] Its preparation method comprises the following steps:

[0031] In a 100mL four-necked flask, add 9.11g (0.05mol) of sorbitol, 10ml of concentrated hydrochloric acid, 0.5g of phosphotungstic acid, 10ml of trimethyl orthoformate, 40ml of DMSO, and stir for 10min, then add 12.1g (0.10mol) of salicylaldehyde ), and react at a temperature of 20-30°C for 12h. Add 30ml of water, stir for 30min, and filter with suction to obtain a solid. The product was washed twice with 50 ml of water, then twice with ice ethanol, and dried to constant weight. The obtained product was 14.4g, yield: 73.8%, melting point: 206.5-207.8°C.

[0032] 1H NMR (400MHz, DMSO-d 6, TMS, 25℃): δ9.20.-9.23(d, J=12.8Hz, 2H, Ar-OH), 7.37-7.39(d, J=7.7Hz, 2H, Ar-H), 6.78-6.80( d,J=7.5Hz,2H,Ar-H),7.46-7.51(s,1H,Ar-H),5.82-5.85(d,J=3.3Hz,2H,OCHO),4....

Embodiment 2

[0037] 1,3:2,4-Di-n-octyl-D-sorbitol, obtained by condensation of sorbitol and n-octylaldehyde, its synthetic route and preparation method are similar to the synthetic route provided in Example 1, see Examples 1, which will not be elaborated here.

[0038] The yield of the resulting product: 82%, melting point: 112.5-114.7°C

[0039] 1H NMR (400MHz, DMSO-d 6 ,TMS,25℃):4.40-4.55(m,2H,OCHO),3.52-3.60(m,8H,OH),3.50-3.31(m,8H,CH)1.58-1.43(m,2H,CH 2 ), 1.40-1.12 (m, 24, CH 2 ),0.83-0.75(t,J=6.7Hz 6H,CH 3 ).

[0040] Two, the synthesis of mannitol bicondensate (compound 6)

[0041] The synthetic route is shown in formula (II):

[0042]

[0043] Wherein, compound 4 is mannitol; Ar 1 To replace the aliphatic aldehyde moiety, compound 5 is an aliphatic aldehyde.

Embodiment 3

[0045] 1,3:2,4-Di-n-octyl-mannitol, obtained by condensation of mannitol and n-octylaldehyde, its synthetic route is shown in formula (II), and its preparation method is similar to the synthetic route provided in Example 1 , can refer to Embodiment 1, and will not be described in detail here.

[0046] Yield of the product obtained: 72%, melting point: 109.3-111.2°C.

[0047] 1H NMR (400MHz, DMSO-d 6 ,TMS,25℃):4.75-4.90(m,2H,OCHO),4.05-3.92(m,2H,OH),3.90-3.31(m,8H,CH)1.56-1.41(m,2H,CH 2 ), 1.40-1.12 (m, 24, CH 2 ),0.82-0.73(t,J=6.7Hz 6H,CH 3 ).

[0048] Three, the synthesis of mannitol tricondensate (compound 8)

[0049] The synthetic route is as shown in formula (Ⅲ):

[0050]

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Abstract

The invention discloses a preparation method of a polyalcohol acetal compound. The preparation method comprises the following steps that polyalcohol, a solvent, a catalyst, a promoter and a water absorbent are added in a reaction vessel and stirred for 10-30 minutes, then substituted aldehyde is added into the mixture to be subjected to a reaction for 2-36 hours at the room temperature, stirring is conducted for 10-30 minutes after water is added, suction filtration, washing and swab-off are conducted, and the polyalcohol acetal compound is obtained, wherein polyalcohol is sorbitol, xylitol ormannitol, the solvent is dimethyl sulfoxide or a compound of dimethyl sulfoxide and methyl alcohol, the catalyst is sulfuric acid, hydrochloric acid, phosphoric acid or nitric acid, the promoter is phosphotungstic acid, the water absorbent is trimethyl orthoformate or triethyl orthoformate, and the substituted aldehyde is aromatic aldehyde or fatty aldehyde. The method is novel in route design, the reaction raw materials are easy to obtain, the product purity is good, post-treatment is simple, the applicability is high, and the method can be widely applied to synthesis of polyalcohol diacetaland polyalcohol triacetal compounds with different structures.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a preparation method of polyol acetal compounds. Background technique [0002] Polyol acetal compounds are products obtained by acetalization reaction of polyalcohols (such as sorbitol, xylitol and mannitol) with aldehydes or substituted aldehydes under the action of acidic catalysts. Among them, reports on sorbitol acetal compounds are more common. Since the 1,3;2,4-dibenzylidene sorbitol (DBS) synthesis patent came out in the 1970s, the production and development of sorbitol acetal compounds have made great progress at home and abroad. Because of its characteristics of forming crystal nuclei and gelling organic solvents, it is used as an additive in industries such as plastics, coatings, adhesives, inks, daily chemicals and medical supplies. There are many preparation methods of polyol acetal compounds, and there are two main categories in summary. [0003] The first type i...

Claims

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Application Information

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IPC IPC(8): C07D493/04C07D493/14C07D319/06
CPCC07D319/06C07D493/04C07D493/14
Inventor 管西栋郭传垒刘克王蕾
Owner TAISHAN MEDICAL UNIV
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