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Preparation method of 2-MCPD, D5-2-MCPD and 13C3-2-MCPD

A target and intermediate technology, applied in the field of high-purity preparation, can solve the problems of complex production process, complex product, high production cost, etc., and achieve the effect of low process cost and environmental friendliness

Pending Publication Date: 2022-08-05
青岛贞开生物医药技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The object of the present invention is to provide a kind of 2-chloro-1,3-propanediol (2-MCPD), D5-2-chloro-1,3-propanediol (D5-2-MCPD), 13 C3-2-chloro-1,3-propanediol ( 13 C3-2-MCPD) and its esters, the prepared product is used as a food processing pollutant analysis reference substance to solve the problems of complex production process, complex product and production cost in the current methods for preparing 2-MCPD related substances. Technical issues with high, poor overall yield defects

Method used

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  • Preparation method of 2-MCPD, D5-2-MCPD and 13C3-2-MCPD
  • Preparation method of 2-MCPD, D5-2-MCPD and 13C3-2-MCPD
  • Preparation method of 2-MCPD, D5-2-MCPD and 13C3-2-MCPD

Examples

Experimental program
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Effect test

Embodiment 1

[0047] Example 1 Synthesis of 2-chloro-1,3-propanediol (2-MCPD)

[0048]

[0049] Step 1: Add glycerol (15g, 0.16mol, 1.0eq), dichloromethane (300mL), triethylamine (48.5g, 0.48mol, 3.0eq) into the reaction kettle, cool down to -10°C, and dropwise add benzyl Acid chloride (46.1 g, 0.33 mol, 2.05 eq), maintaining the reaction temperature at -10-0 °C. After the dropwise addition was completed, the reaction was continued for 60 minutes. Water (150 mL) was added, and the mixture was fully stirred for 10 minutes, the upper aqueous phase was separated, and the lower organic phase was concentrated to dryness.

[0050] Step 2: Add the concentrated solution of Step 1 and dichloromethane (300mL) into the reactor, slowly add phosphorus pentachloride (50g, 0.24mol, 1.5eq), maintain the reaction temperature at 15-20°C, and stir the reaction for 5 hours . Slowly add water (150 mL), stir well for 10 minutes, separate the upper aqueous phase, and concentrate the lower organic phase to d...

Embodiment 2

[0052] Example 2 Synthesis of 2-chloro-1,3-propanediol stearic acid diester (2-MCPD stearic acid diester)

[0053]

[0054] 2-Chloro-1,3-propanediol (2-MCPD) (5g, 0.045mol, 1.0eq), stearic acid (25.6g, 0.090mol, 2.0eq), 4-dimethylformaldehyde in Step 3 of Example 1 were mixed Aminopyridine (DMAP) (0.55g, 0.0045mol, 0.1 eq), dicyclohexylcarbodiimide (DCC) (22.2g, 0.11mol, 2.4eq), and dichloromethane (150mL) were added to the reaction kettle, at room temperature Stir for 5-6 hours. Water (150 mL) was added, fully stirred for 10 minutes, the upper aqueous phase was separated, the lower organic phase was concentrated to dryness, methanol (100 mL) was added, stirred for 1 hour, and filtered to obtain 2-chloro-1,3-propanediol stearic acid diester ( 2-MCPD stearic acid diester) pure product 26.2g (see NMR spectrum image 3 ), the yield was 90.2%.

Embodiment 3

[0055] Example 3 Synthesis of 2-chloro-1,3-propanediol (2-MCPD)

[0056]

[0057] Step 1: Add glycerol (3g, 0.033mol, 1.0eq), dichloromethane (60mL), triethylamine (9.9g, 0.098mol, 3.0eq) into the reaction kettle, cool down to -10°C, slowly add tert-butyl Diphenylchlorosilane (18.6g, 0.068mol, 2.05eq), maintaining the reaction temperature at -10-0°C. After the addition was completed, the reaction was continued for 60 minutes. Water (50 mL) was added, and the mixture was fully stirred for 10 minutes, the upper aqueous phase was separated, and the lower organic phase was concentrated to dryness.

[0058] Step 2: Add the concentrated solution of step 1 and dichloromethane (60mL) into the reaction kettle, slowly add phosphorus trichloride (6.8g, 0.050mol, 1.5eq), maintain the reaction temperature at 15-20°C, and stir for 5 Hour. Slowly add water (60 mL), stir well for 10 minutes, separate the upper aqueous phase, and concentrate the lower organic phase to dryness.

[0059] ...

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Abstract

The invention provides a preparation method of 2-chloro-1, 3-propylene glycol (2-MCPD), D5-2-chloro-1, 3-propylene glycol (D5-2-MCPD), 13C3-2-chloro-1, 3-propylene glycol (13C3-2-MCPD) and esters of the 2-chloro-1, 3-propylene glycol (2-MCPD), the D5-2-chloro-1, 3-propylene glycol (D5-2-MCPD), the 13C3-2-chloro-1, 3-propylene glycol (13C3-2-MCPD) and the esters of the 2-chloro-1, 3-propylene glycol (2-MCPD) and the esters of the 2-chloro-1 The preparation method comprises the following steps: by taking a large amount of chemical product glycerol as a main raw material, and taking the main raw material and cheap and easily available auxiliary raw materials such as acetyl chloride, benzoyl chloride, benzenesulfonyl chloride, triisopropyl chlorosilane, trimethylchlorosilane and tert-butyl diphenyl chlorosilane, firstly synthesizing a glyceride or ether intermediate A with oxygen at two ends protected by a protecting group R1 under the catalysis of a basic catalyst; the preparation method comprises the following steps: firstly, preparing 2-MCPD from 2-MCPD, then chloridizing through chloridizing reagents such as PCl3 and PCl5 to obtain a chloridized intermediate B, finally removing a protecting group R1 to obtain 2-MCPD, and condensing 2-MCPD and corresponding fatty acid through a condensing agent to obtain 2-MCPD ester. The preparation, separation and purification processes of the whole route are simple, high-purity products are easy to obtain, the used reagents are environment-friendly, the total yield is 70-80%, and the process cost is low.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a kind of 2-chloro-1,3-propanediol (2-MCPD), D5-2-chloro-1,3-propanediol (D5-2-MCPD), 13 C3-2-Chloro-1,3-propanediol( 13 C3-2-MCPD) high purity preparation method. technical background [0002] 2-Chloro-1,3-propanediol (2-MCPD) (Formula I) and its related product 2-chloro-1,3-propanediol ester (2-MCPD ester) (Formula II) are compounds produced during food thermal processing. Contaminants of this type have been detected in soy sauce condiments, semi-solid condiments, cereals, coffee, fish, meat products, potatoes, nuts and heat-processed oil foods based on vegetable oils. Especially in the past one or two years, Detection reports have been reported in infant formula, potato chips, shrimp crackers and other crispy snacks. Due to their reproductive toxicity, nephrotoxicity, immunotoxicity and carcinogenicity, in 2014, the European Union issued resolution 2014 / 661 / EU to con...

Claims

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Application Information

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IPC IPC(8): C07C29/09C07C31/42C07C27/02C07C67/08C07C69/28C07C69/58
CPCC07C29/095C07C67/287C07C67/14C07C67/08C07F7/188C07F7/1892C07B2200/05C07C31/42C07C69/78C07C69/28C07C69/58Y02P20/55
Inventor 吴子文宫斌曹建华
Owner 青岛贞开生物医药技术有限公司
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