CN112479878B - Method for preparing 6, 8-dichloro ethyl caprylate - Google Patents
Method for preparing 6, 8-dichloro ethyl caprylate Download PDFInfo
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
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- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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Abstract
The present invention provides aA process for preparing ethyl 6, 8-dichlorooctanoate. As shown in the following reaction formula, the method comprises the following reactions: the compound 1 is oxidized and esterified to obtain a compound 2, then dehydrated to generate a compound 3, and then subjected to Prins condensation reaction to obtain a compound 4, and then subjected to hydrolysis and hydrogenation to obtain a compound 5, and finally chlorinated to obtain 6, 8-dichloro ethyl caprylate. The method has the characteristics of easily obtained raw materials, simple process, high efficiency and environmental protection.
Description
Technical Field
The invention relates to the field of chemical synthesis, and particularly relates to a method for synthesizing 6, 8-dichloro ethyl caprylate.
Background
Lipoic acid belongs to a class of compounds in B vitamins, plays a coenzyme role in a multienzyme system, is an antioxidant, has better antioxidant effect than vitamins, and can eliminate free radicals for accelerating aging and causing diseases; can improve insulin function and heart rate variability of diabetic; treating hepatitis C; protecting kidney and pancreas; preventing cataract; inhibiting HIV proliferation. The 6, 8-dichloro ethyl caprylate is an important organic intermediate for synthesizing lipoic acid. The existing method for synthesizing 6, 8-dichloro ethyl caprylate mainly comprises an adipic acid route, a cyclohexanone route and the like. Xi Ruo Ming et al introduced the synthesis of methyl 6, 8-dichlorooctanoate from adipic acid by methyl esterification, chlorination, ethylene addition, reductive chlorination (as shown in the following reaction scheme), which resulted in a large amount of solid waste and liquid waste, and the formation of polymer and difficult separation.
In another route, cyclohexanone and vinyl ethyl ether are used as raw materials, and CN 107673972 discloses a method for synthesizing ethyl 6, 8-dichlorooctanoate by using cyclohexanone and vinyl ethyl ether as raw materials (as shown in the following reaction formula). The starting material of the route is easy to obtain, and the route is a synthesis route with industrial potential, but the number of byproducts is relatively large.
In summary, the current method for preparing ethyl 6, 8-dichlorooctanoate has harsh reaction conditions, long steps and low yield, and a large amount of wastewater generated in the reaction process pollutes the environment.
Disclosure of Invention
The invention aims to provide a method for preparing 6, 8-dichloro ethyl caprylate, which has the characteristics of easily obtained raw materials, simple process, high efficiency and environmental protection.
According to one aspect of the present invention, there is provided a process for the preparation of ethyl 6, 8-dichlorooctanoate, said process comprising the steps of:
as shown in the reaction formula, the compound 1 is oxidized and esterified to obtain a compound 2, then dehydrated to generate a compound 3, then subjected to Prins condensation reaction to obtain a compound 4, then subjected to hydrolysis and hydrogenation to obtain a compound 5, and finally chlorinated to obtain 6, 8-dichloro ethyl octanoate.
In a specific embodiment, the method comprises the steps of:
1) Adding the compound 1, a catalyst 1, an oxidant, ethanol and a water-carrying agent into a reaction kettle for reaction, continuously evaporating the water-carrying agent and water, finishing the reaction when no water is generated, and distilling the product to obtain a compound 2;
2) Introducing the compound 2 into a fixed bed reactor filled with the catalyst 2, heating to the reaction temperature in a nitrogen atmosphere, introducing reactants into the reactor by using a plunger pump for reaction, and distilling and purifying the product to obtain a compound 3;
3) Adding a compound 3, a solvent, a formaldehyde source and a catalyst 3 into a reaction kettle for reaction, and distilling and refining a product to obtain a compound 4;
4) Adding a compound 4, water and a catalyst 4 into a reaction kettle, reacting in a hydrogen atmosphere, and distilling a product to obtain a compound 5;
5) Adding the compound 5 into a flask, purging a reaction system with nitrogen, adding a chlorinating agent into the flask, heating for reflux reaction, and distilling to obtain the 6, 8-dichloro ethyl caprylate.
In a specific embodiment, in step 1), the catalyst 1 is a supported metal catalyst, the supported metal catalyst comprises a metal active component and a carrier, the metal active component comprises one or more of Pd, pt, ru, rh, ir, ni and Cu, and the carrier comprises one or more of activated carbon, alumina, silica, titania, niobium pentoxide, sulfated zirconia, zirconia and a molecular sieve; alternatively, the catalyst may be one or more of activated carbon, alumina, silica, titania, niobium pentoxide, sulfated zirconia, molecular sieves, sulfonated macroporous resins, amberlyst-15 or Amberlyst-35.
In a particular embodiment, in step 1), the mass ratio of said catalyst 1 to compound 1 is between 1 and 20 and 20000, preferably between 1 and 500 and 1000.
In a specific embodiment, in step 1), the water-carrying agent is selected from any one or a combination of two or more of benzene, toluene, xylene, chloroform and dichloroethane.
In a specific embodiment, in step 1), the oxidant is selected from any one or a combination of two or more of air, oxygen, hydrogen peroxide, peroxyorganic acid, m-chloroperoxybenzoic acid, dichloroisocyanuric acid and sodium hypochlorite.
In a particular embodiment, in step 1), the molar ratio between compound 1 and ethanol is 1.
In a particular embodiment, in step 1), the reaction temperature is between 50 and 250 ℃, preferably between 90 and 100 ℃.
In a particular embodiment, in step 2), the catalyst 2 comprises one or more of gamma-alumina, silica, niobium pentoxide, sulfonated activated carbon, molecular sieves, zirconia.
In a particular embodiment, in step 2), the reaction temperature is between 250 and 600 ℃.
In a specific embodiment, in step 2), the space velocity of the reactant feeding is 0.01-6h -1 Preferably 0.02-4h -1 。
In a specific embodiment, in step 3), the catalyst 3 comprises ion exchange resin, sulfonated macroporous resin, nafion, activated carbon, carbon nanotubes, γ -Al 2 O 3 、SiO 2 、ZrO 2 、WO 3 、Nb 2 O 5 And zeolite molecular sieve, and the ion exchange resin may be Amberlyst-15 or Amberlyst-35.
In a specific embodiment, in step 3), the mass ratio of the catalyst 3 and the compound 3 is 1
In a specific embodiment, in step 3), the solvent comprises any one of water, methanol, ethanol, tetrahydrofuran, 1, 4-dioxane, and acetonitrile.
In a particular embodiment, in step 3), the formaldehyde source comprises aqueous formaldehyde or paraformaldehyde.
In a particular embodiment, in step 3), the reaction temperature is between 60 and 200 ℃, preferably between 100 and 150 ℃.
In a particular embodiment, in step 3), the reaction time is between 30 minutes and 60 hours, preferably between 10 and 20 hours.
In a specific embodiment, in step 4), the catalyst 4 is a supported metal catalyst, the supported metal catalyst comprises a metal active component and a carrier, and the metal active component comprises one or more of Pd, pt, ru, rh, ir, ni and Cu; the carrier comprises one or more of activated carbon, alumina, silica, titanium oxide and molecular sieve.
In a particular embodiment, in step 4), the mass ratio between said catalyst 4 and said compound 4 is between 1 and 20% and 200%.
In a particular embodiment, in step 4), the mass ratio of compound 4 to water is 1.
In a particular embodiment, in step 4), the reaction temperature is between 60 and 200 ℃, preferably between 100 and 150 ℃.
In a particular embodiment, in step 4), the reaction pressure is between 0.3 and 6MPa.
In a particular embodiment, in step 5), the chlorinating agent comprises HCl, aqueous HCl, PCl 3 、PCl 5 、SOCl 2 、CHCl 3 、ZnCl 2 Or CCl 4 One or more of (a).
In a particular embodiment, in step 5), the reaction temperature is between 50 and 250 ℃.
In a particular embodiment, in step 5), the reaction time is between 30 minutes and 60 hours, preferably between 2 and 3 hours.
The invention has the advantages of
The invention takes 7-hydroxyheptanal as raw material, and adopts a simple, easy and efficient method to synthesize 6, 8-dichloro ethyl caprylate. The method obtains the 6, 8-dichloro ethyl caprylate through the steps of oxidation, esterification, dehydration, prins condensation, hydrolysis and chlorination, in the process, a catalytic reaction method is mostly adopted, the atom utilization rate is high, and less organic chemical reagents are adopted, so that the wastewater pollution is greatly reduced, the process route is clean (only a small amount of wastewater is discharged in the last chlorination step), and compared with the traditional method reported at present, the initial raw materials are cheap and easy to obtain, the final product quality yield exceeds 55% (the prior art reports that the yield is less than 30%), the cost advantage is achieved, and the industrial amplification is easy.
Detailed Description
The present invention is described in detail below by way of specific examples, which, however, are not intended to limit the scope of the present application.
In this application, the use of the terms "catalyst 1", "catalyst 2", "catalyst 3" \8230; \8230, etc. are used only to distinguish one catalyst from another, and have no other meaning.
In examples 1-3 below, the product, ethyl 6, 8-dichlorooctanoate, was prepared by the following reaction scheme:
example 1
Step 1: 104g of the compound 1, 100g of absolute ethyl alcohol, 0.1g of Pd/HZSM-5 catalyst and 100ml of toluene are added into a reaction kettle, air is continuously introduced into the system, the system is heated to 90 ℃, toluene and water are continuously distilled out, the toluene is continuously added into the system again until no water is distilled out, the temperature is reduced, the product is distilled under reduced pressure to obtain 118g of a compound 2 (2.5 mmHg,101-104 ℃), and the molar yield of the compound 2 is 85%.
And 2, step: adding 5g of gamma-alumina into the fixed bed, taking nitrogen as carrier gas, heating to 350 ℃, and reacting the compound 2 for 0.02h -1 Pumping the product into a fixed bed layer, and collecting the product after condensation and gas-liquid separation. The product was distilled under reduced pressure to give 79g of Compound 3 (30mmHg, 69-71 ℃ C.), with a molar yield of 75% of Compound 3.
And step 3: 79g of Compound 3, 35g of paraformaldehyde, 100ml of methanol and 1.0g of Amberlyst-15 resin were charged into the reaction vessel and reacted at 100 ℃ for 10 hours. After completion of the reaction, filtration was carried out, and distillation under reduced pressure was continued after evaporation of methanol to obtain 91g of Compound 4 (0.5mmHg, 121 ℃ C.), the molar yield of Compound 4 being 83%.
And 4, step 4: 91g of compound 4, 20g of water and 1g of Pt/gamma-Al are added to the reaction kettle 2 O 3 Catalyst, sealing the kettle and then using N 2 And (3) maintaining the pressure for 3MPa after 5 times of replacement to ensure that the pressure of the reaction kettle is released after no gas leakage, filling 5MPa hydrogen, heating to 100 ℃ for reaction, supplementing the hydrogen in the reaction process until the pressure is unchanged, cooling, distilling after pressure release to obtain 69g of compound 5 (2mmHg, 149-154 ℃), wherein the molar yield of the compound 5 is 81%.
And 5: 85ml of thionyl chloride was added to the flask, stirred, and 69g of Compound 5 was slowly dropped thereinto over about 2 hours, and the gas generated during the dropping was absorbed with an alkali. After the dropwise addition, the mixture was heated to 80 ℃ and refluxed for 2 hours, and 70g of ethyl 6, 8-dichlorooctanoate (2mmHg, 124-127 ℃) was obtained by distillation, the molar yield being 86%.
Example 2
Step 1: 106g of Compound 1, 100g of ethanol, 0.1g of Pt/Nb 2 O 5 Catalyst and 100ml toluene were continuously introduced into the system and heated to 100 ℃ at which point toluene and water were distilled off, toluene was continuously added back to the system until no more water was distilled off, the temperature was reduced, and the product was distilled to give 114g of Compound 2 (2.5 mmHg,101-104 ℃) in a molar yield of 81%.
Step 2: adding 5g of H-ZSM-5 into the fixed bed, taking nitrogen as carrier gas, heating to 400 ℃, and reacting the compound 2 for 0.02H -1 Pumping the product into a fixed bed layer, and collecting the product after condensation and gas-liquid separation. The product was distilled to give 73g of Compound 3 (30mmHg, 69-71 ℃ C.), with a molar yield of 71% of Compound 3.
And 3, step 3: 73g of compound 3, 40g of paraformaldehyde, 100ml of methanol and 1.0g of H-ZSM-5 were added to a reaction kettle, and the mixture was reacted at 100 ℃ for 10 hours. After the completion of the reaction, the reaction mixture was filtered, methanol was distilled off, and the distillation under reduced pressure was carried out to obtain 83g of Compound 4 (0.5mmHg, 121 ℃ C.), whereby the molar yield of Compound 4 was 82%.
And 4, step 4: 83g of compound 4, 20g of water and 1g of Ni/gamma-Al are added into a reaction kettle 2 O 3 Catalyst, sealing the reactor and then using N 2 And (3) maintaining the pressure for 3MPa after 5 times of replacement to ensure that the pressure of the reaction kettle is released after no gas leakage, filling 5MPa hydrogen, heating to 100 ℃ for reaction, supplementing the hydrogen in the reaction process until the pressure is unchanged, cooling, distilling after pressure release to obtain 65g of a compound 5 (2mmHg, 149-154 ℃), wherein the molar yield of the compound 5 is 83%.
And 5: a flask was charged with 65g of Compound 5, 25g of Zinc chloride and 160ml of concentrated hydrochloric acid, heated to 100 ℃ and refluxed for 3 hours, cooled, and the organic layer was separated. The organic phase was washed with saturated brine, dried over anhydrous calcium chloride and distilled to give 61g of ethyl 6,8-dichlorooctanoate (2mmHg, 124-127 ℃ C.), in a molar yield of 80%.
Example 3
Step 1: adding 100g of compound 1 into a reaction kettle, adding 100g of ethanol and 0.1g of Pt/gamma-A 2 O 3 Catalyst and 100ml toluene, continuously introducing air into the system, and heating to 100 deg.C in the presence of toluene and waterThe toluene was distilled off and added back to the system until no more water was distilled off, the temperature was reduced and the product distilled to give 115g of Compound 2 (2.5 mmHg,101-104 ℃ C.) in a molar yield of 86% of Compound 2.
And 2, step: 5g of gamma-Al are added in a fixed bed 2 O 3 Heating to 400 deg.C with nitrogen as carrier gas, and allowing compound 2 to react for 0.02h -1 Pumping the product into a fixed bed layer, and collecting the product after condensation and gas-liquid separation. The product was distilled to give 75g of Compound 3 (30mmHg, 69-71 deg.C), 73% molar yield of Compound 3.
And step 3: 75g of Compound 3, 40g of paraformaldehyde, 100ml of methanol and 1.0g of Amberlyst-15 were charged into a reaction vessel and reacted at 100 ℃ for 10 hours. After completion of the reaction, the reaction mixture was filtered, methanol was distilled off, and the distillation under reduced pressure was carried out to obtain 90g of Compound 4 (0.5mmHg, 121 ℃ C.), whereby the molar yield of Compound 4 was 87%.
And 4, step 4: 90g of compound 4, 20g of water and 1g of Pd/gamma-Al are added into a reaction kettle 2 O 3 Sealing the kettle and then using N 2 And (3) maintaining the pressure for 3MPa after 5 times of replacement to ensure that the pressure of the reaction kettle is released after no gas leakage, filling 5MPa hydrogen, heating to 100 ℃ for reaction, supplementing the hydrogen in the reaction process until the pressure is unchanged, cooling, distilling after pressure release to obtain 77g of compound 5 (2mmHg, 149-154 ℃), wherein the molar yield of the compound 5 is 89%.
And 5: 85ml of thionyl chloride was added to the flask, stirred, and 77g of Compound 5 was slowly dropped thereinto over about 2 hours, and the gas generated during the dropping was absorbed with an alkali. After the addition, the mixture was heated to 80 ℃ and refluxed for 2 hours, and 78g of ethyl 6, 8-dichlorooctanoate (2mmHg, 124-127 ℃) was obtained by distillation, the molar yield being 87%.
Claims (8)
1. A method for preparing 6, 8-dichloro ethyl caprylate,
according to the reaction formula, the compound 1 is oxidized and esterified to obtain a compound 2, then dehydrated to generate a compound 3, then subjected to Prins condensation reaction to obtain a compound 4, then subjected to hydrolysis and hydrogenation to obtain a compound 5, and finally chlorinated to obtain 6, 8-dichloro ethyl caprylate,
the method comprises the following steps:
1) Adding a compound 1, a catalyst 1, an oxidant, ethanol and a water-carrying agent into a reaction kettle for reaction, distilling the water-carrying agent and water out, ending the reaction when no water is generated, and distilling a product to obtain a compound 2, wherein the oxidant is selected from air and oxygen;
2) Introducing the compound 2 into a fixed bed reactor filled with the catalyst 2, heating to the reaction temperature in a nitrogen atmosphere, introducing reactants into the reactor by using a plunger pump for reaction, and distilling and purifying the product to obtain a compound 3;
3) Adding a compound 3, a solvent, a formaldehyde source and a catalyst 3 into a reaction kettle for reaction, and distilling and refining a product to obtain a compound 4, wherein the formaldehyde source is selected from a formaldehyde aqueous solution and paraformaldehyde;
4) Adding a compound 4, water and a catalyst 4 into a reaction kettle, reacting in a hydrogen atmosphere, and distilling a product to obtain a compound 5; and
5) Adding a compound 5 into a flask, purging a reaction system by nitrogen, adding a chlorinating agent into the flask, heating and refluxing for reaction, and distilling to obtain the 6, 8-dichloro octanoic acid ethyl ester, wherein the chlorinating agent is selected from SOCl 2 、ZnCl 2 One or two of the components (a) and (b),
the catalyst 1 is a supported metal catalyst, the supported metal catalyst is composed of a metal active component and a carrier 1, the metal active component is one or two of Pd and Pt, and the carrier 1 is one or more of alumina, niobium pentoxide and a molecular sieve;
the catalyst 2 is selected from gamma-alumina and molecular sieve;
the catalyst 3 is selected from Amberlyst-15 and zeolite molecular sieve; and
the catalyst 4 is a supported metal catalyst, the supported metal catalyst is composed of a metal active component and a carrier 2, the metal active component is selected from one or more of Pd, pt and Ni, and the carrier 2 is alumina.
2. The method of claim 1, wherein the first and second light sources are selected from the group consisting of,
wherein, in the step 1),
the mass ratio of the catalyst 1 to the compound 1 is 1;
the water-carrying agent is selected from any one or the combination of more than two of benzene, toluene, xylene, chloroform and dichloroethane;
the molar ratio between the compound 1 and ethanol is 1.
3. The method of claim 1, wherein the first and second light sources are selected from the group consisting of,
wherein, in the step 3),
the mass ratio of the catalyst 3 to the compound 3 is 1;
the solvent is selected from any one of water, methanol, ethanol, tetrahydrofuran, 1, 4-dioxane and acetonitrile.
4. The method of claim 1, wherein the first and second light sources are selected from the group consisting of,
wherein, in the step 4),
the mass ratio of the catalyst 4 to the compound 4 is 1; the mass ratio of the compound 4 to water is 1.
5. The method as set forth in claim 1, wherein,
wherein the reaction temperature of the step 1) is 50-250 ℃;
the reaction temperature of the step 2) is 250-600 ℃, and the space velocity of the reactant feeding is 0.01-6h -1 ；
The reaction temperature of the step 3) is 60-200 ℃, and the reaction time is 30 minutes-60 hours;
the reaction temperature of the step 4) is 60-200 ℃, and the reaction pressure is 0.3-6MPa;
the reaction temperature of the step 5) is 50-250 ℃, and the reaction time is 30 minutes-60 hours.
6. The method of claim 1, wherein the first and second light sources are selected from the group consisting of,
wherein the reaction temperature of the step 1) is 90-100 ℃; the reaction temperature of the step 3) is 100-150 ℃; the reaction temperature in the step 4) is 100-150 ℃.
7. The method of claim 1, wherein the first and second light sources are selected from the group consisting of,
wherein the reaction time of the step 3) is 10-20 hours; the reaction time of step 5) is 2-3 hours.
8. The method of claim 1, wherein the first and second light sources are selected from the group consisting of,
wherein, in the step 1), the mass ratio of the catalyst 1 to the compound 1 is 1;
in the step 2), the space velocity of the reactant feeding is 0.02-4h -1 。
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| CN113185494B (en) * | 2021-05-17 | 2022-04-15 | 苏州富士莱医药股份有限公司 | Preparation method of R-lipoic acid |
| CN113429386B (en) * | 2021-07-09 | 2022-03-18 | 苏州富士莱医药股份有限公司 | Synthetic method of R-lipoic acid |
| CN113773182B (en) * | 2021-09-10 | 2024-02-06 | 风火轮(上海)生物科技有限公司 | Method for synthesizing 6, 8-dichloro octanoate |
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