CN104844421A - Preparation method for (R)-3-chloro-1,2-propanediol - Google Patents
Preparation method for (R)-3-chloro-1,2-propanediol Download PDFInfo
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- CN104844421A CN104844421A CN201510206172.9A CN201510206172A CN104844421A CN 104844421 A CN104844421 A CN 104844421A CN 201510206172 A CN201510206172 A CN 201510206172A CN 104844421 A CN104844421 A CN 104844421A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
Abstract
The invention discloses a preparation method for (R)-3-chloro-1,2-propanediol. The preparation method comprises the following steps: 1) subjecting (S)-3-chloro-1,2-epoxypropane and water to a ring-opening reaction in the presence of an acidic catalyst so as to obtain a ring-opening mixture; 2) subjecting alkali lye and the ring-opening mixture to a neutralization reaction so as to obtain a neutralization mixture; 3) removing water in the neutralization mixture and carrying out filtering so as to obtain a filtrate; and 4) fractionating the filtrate at a pressure of 30 to 35 pa and a temperature of 125 to 128 DEG C so as to prepare (R)-3-chloro-1,2-propanediol. The preparation method has excellent yield; and prepared (R)-3-chloro-1,2-propanediol has excellent total purity and low water content, and in particular, chiral purity of (R)-3-chloro-1,2-propanediol is as high as 99.5%.
Description
Technical field
The present invention relates to the preparation method of one (R)-3-chlorine-1,2-propylene glycol.
Background technology
(R)-3-chlorine-1,2-propylene glycol is important glycerine chloro thing, of many uses: to can be used as organic synthesis intermediate, is used for synthetic pesticide, dyestuff, medicine, coating, veterinary drug, softening agent, tensio-active agent and dyeing and printing auxiliary etc.; Can be used as solvent, for the production of cellulose acetate etc.; Also can be used as the reagent of medical research, for the research of reproductive medicine; In recent ten years, application in space flight material, non-ionic contrast agent, electronics chemical, catalyzer synthesis and phase-transfer catalyst application etc. is increasingly extensive, increase substantially the requirement of the index such as purity, foreign matter content of glycerin chlorohydrin is also corresponding, therefore more harsh requirement is proposed to the suitability for industrialized production of glycerin chlorohydrin.
In prior art, (R)-3-chloro-1, the preparation of 2-propylene glycol mainly contains following two kinds of methods: one is epoxy chloropropane method, be that epoxy chloropropane is added in reactor, stir, add acid and make reaction solution be acid, heat up, hydrolysis reaction terminates, and after adding NaOH adjustment hydrolyzed solution pH value, products therefrom underpressure distillation is got product; Two is glycerin chlorination methods, glycerine and acetic acid is added reactor, is heated with stirring to specified temperature, logical dry hydrogen chloride gas, and be terminal to reaction solution weightening finish to 150% (theoretical value), distillation reaction product obtains crude product, then underpressure distillation obtains finished product.Wherein, glycerin chlorination method (R)-3-chloro-1 because producing, containing 1 of more amount in 2-propylene glycol, 3-dichlorohydrine and 1,2-dichlorohydrine, if adopt repeatedly distilation, can occur to decompose or polymerization, reaction generates macromolecular cpd or polymkeric substance, cause glycerin chlorohydrin finished product with color and occur that higher-boiling compound content is high, sometimes higher-boiling compound content can more than 0.5% (GC), or more.Therefore, utilizing epoxy chloropropane method to produce is comparatively normal employing and comparatively proven technique both at home and abroad.But when epoxy chloropropane method is produced, due to the selection of catalyzer, the impact of the process aspect such as use and reinforced order, gradient increased temperature, the impact of the factor such as lectotype selection, processing condition of especially last distillation process, obtained product purity is generally lower than 90%, particularly chiral purity is the highest can only reach 95%, also exist in addition and improve purity and can cause degradation problem (current productive rate is between 65.2%-75%) under productive rate, directly affect economic benefit and the market competition of product.Although occurred have employed vacuum scraper thin film evaporation mode in the separation of glycerin chlorohydrin at present, but still do not solve high purity and the problem such as stratographic analysis main peak rear impurity peak is many, foreign matter content is higher.
Summary of the invention
The object of this invention is to provide one (R)-3-chloro-1, the preparation method of 2-propylene glycol, this preparation method has excellent productive rate, (the R)-3-chloro-1 simultaneously prepared, 2-propylene glycol has excellent total purity and low water ratio, and especially chiral purity can up to 99.5%.
To achieve these goals, the invention provides the preparation method of one (R)-3-chlorine-1,2-propylene glycol, this preparation method comprises:
1) under the existence of an acidic catalyst, (S)-epichlorohydrin and water are carried out ring-opening reaction to obtain open loop mixture;
2) alkali lye and open loop mixture are carried out neutralization reaction to obtain neutralise mixt;
3) water in neutralise mixt is removed, then filter to obtain filtrate;
4) filtrate is carried out at 30-35pa and 125-128 DEG C fractionation with obtained (R)-3-chlorine-1,2-propylene glycol.
By technique scheme, in preparation method provided by the invention first under the existence of an acidic catalyst, (S)-epichlorohydrin and water are carried out ring-opening reaction to obtain open loop mixture; Then neutralization reaction is carried out to obtain neutralise mixt by alkali lye and open loop mixture; Then the water in neutralise mixt is removed, then filter to obtain filtrate; Finally filtrate is carried out at 30-35pa and 125-128 DEG C fractionation with obtained (R)-3-chlorine-1,2-propylene glycol.For existing epoxy chloropropane method, water in neutralise mixt is first removed by method provided by the invention, then under given conditions to filtrate fractionation, thus make this preparation method have excellent productive rate, (the R)-3-chloro-1 simultaneously prepared, 2-propylene glycol has excellent total purity and low water ratio, and especially chiral purity can up to 99.5%.
Other features and advantages of the present invention are described in detail in embodiment part subsequently.
Accompanying drawing explanation
Accompanying drawing is used to provide a further understanding of the present invention, and forms a part for specification sheets, is used from explanation the present invention, but is not construed as limiting the invention with embodiment one below.In the accompanying drawings:
Fig. 1 is the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol in embodiment 1;
Fig. 2 is the nuclear-magnetism carbon spectrum of (R)-3-chlorine-1,2-propylene glycol in embodiment 1.
Embodiment
Below the specific embodiment of the present invention is described in detail.Should be understood that, embodiment described herein, only for instruction and explanation of the present invention, is not limited to the present invention.
The invention provides the preparation method of one (R)-3-chlorine-1,2-propylene glycol, this preparation method comprises:
1) under the existence of an acidic catalyst, (S)-epichlorohydrin and water are carried out ring-opening reaction to obtain open loop mixture;
2) alkali lye and open loop mixture are carried out neutralization reaction to obtain neutralise mixt;
3) water in neutralise mixt is removed, then filter to obtain filtrate;
4) filtrate is carried out at 30-35pa and 125-128 DEG C fractionation with obtained (R)-3-chlorine-1,2-propylene glycol.
In the present invention, an acidic catalyst can be an acidic catalyst of any one routine in this area, concrete kind can be selected in wide scope, but in order to make (the R)-3-chloro-1 prepared, 2-propylene glycol has more excellent total purity (especially chiral purity), productive rate and low water ratio, preferably, in step 1) in, an acidic catalyst be selected from sulfuric acid, phosphoric acid and hydrochloric acid one or more.
In step 1 of the present invention) in, the concrete consumption of each material can be selected in wide scope, but in order to make (the R)-3-chloro-1 prepared, 2-propylene glycol has more excellent total purity (especially chiral purity), productive rate and low water ratio, preferably, in step 1) in, relative to (S)-3-chloro-1 of 100 weight parts, 2-propylene oxide, the consumption of water is 40-80 weight part, and the consumption of an acidic catalyst is 0.5-2 weight part.
In step 1 of the present invention) in, the actual conditions of ring-opening reaction can be selected in wide scope, but in order to make (the R)-3-chloro-1 prepared, 2-propylene glycol has more excellent total purity (especially chiral purity), productive rate and low water ratio, preferably, in step 1) in, ring-opening reaction meets the following conditions: temperature of reaction is 105-110 DEG C, and the reaction times is 2-6h.
In step 2 of the present invention) in, the concrete kind of alkali lye can be selected in wide scope, but in order to make (the R)-3-chloro-1 prepared, 2-propylene glycol has more excellent total purity (especially chiral purity), productive rate and low water ratio, preferably, in step 2) in, alkali lye be selected from aqueous sodium hydroxide solution, potassium hydroxide aqueous solution and baryta water one or more.Wherein, in alkali lye, the concrete content of alkali can be selected in wide scope, but has more excellent total purity (especially chiral purity), productive rate and low water ratio in order to (the R)-3-chlorine-1,2-propylene glycol improving preparation further.More preferably, in step 2) in, in alkali lye, the massfraction of alkali is 3-10%.More preferably, relative to the described open loop mixture of 100 weight parts, the consumption of described alkali lye is 12-20 weight part.
In the present invention, select in the scope that the concrete scope of the pH of neutralise mixt can be wide, but in order to make (the R)-3-chloro-1 prepared, 2-propylene glycol has more excellent total purity (especially chiral purity), productive rate and low water ratio, preferably, in step 2) in, the pH of neutralise mixt is 6-8.
In the present invention, select in the scope that the actual conditions of neutralization reaction can be wide, but in order to make (the R)-3-chloro-1 prepared, 2-propylene glycol has more excellent total purity (especially chiral purity), productive rate and low water ratio, preferably, in step 2) in, neutralization reaction meets the following conditions: temperature of reaction is 15-35 DEG C, and the reaction times is 5-15min.
In step 3 of the present invention) in, in order to reduce the moisture in filtrate, preferably, in step 3) in, after being removed by the water in neutralise mixt, in mixture, water content is 0.1-0.5%.
Below will be described the present invention by embodiment.In following examples, total purity (referring to the total content of (R)-3-chlorine-1,2-propylene glycol and (S)-3-chlorine-1,2-propylene glycol in product matter) parameter is recorded by the method for Q/WZY009-2009; Chiral purity (referring to the total content of (R)-3-chlorine-1,2-propylene glycol in product matter) parameter is separated by column chromatography, is then recorded by weighting method; Water ratio parameter is recorded by Karl_Fischer method method.(S)-epichlorohydrin is the commercially available product of Hangzhou Tuo Mu Science and Technology Ltd., and other raw materials are conventional commercially available product.
Embodiment 1
1) at 108 DEG C, (S)-epichlorohydrin 100g, water 60g and sulfuric acid 1.5g are carried out ring-opening reaction 6h with obtained open loop mixture;
2) at 25 DEG C, 15g aqueous sodium hydroxide solution (massfraction of sodium hydroxide is 5%) and 100g open loop mixture are carried out neutralization reaction 15min to obtain neutralise mixt (pH is for 7.0);
3) by underpressure distillation, the water in neutralise mixt is removed (after dewatering, the water ratio of mixture is 0.3%), then filter to obtain filtrate;
4) filtrate is carried out at 33pa and 126 DEG C fractionation with obtained (R)-3-chlorine-1,2-propylene glycol.
The nucleus magnetic hydrogen spectrum being somebody's turn to do (R)-3-chlorine-1,2-propylene glycol is shown in Fig. 1, and nuclear-magnetism carbon spectrum is shown in Fig. 2.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Embodiment 2
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is in step 3) in, after dewatering, the water ratio of mixture is 0.1%.
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Embodiment 3
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is in step 3) in, after dewatering, the water ratio of mixture is 0.5%.
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Embodiment 4
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is in step 4) in, the pressure of fractionation is 30pa.
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Embodiment 5
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is in step 4) in, the pressure of fractionation is 35pa.
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Embodiment 6
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is in step 4) in, the temperature of fractionation is 125 DEG C.
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Embodiment 7
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is in step 4) in, the temperature of fractionation is 128 DEG C.
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Comparative example 1
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is, without step 3).
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Comparative example 2
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is in step 4) in, the pressure of fractionation is 25pa.
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Comparative example 3
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is in step 4) in, the pressure of fractionation is 40pa.
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Comparative example 4
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is in step 4) in, the temperature of fractionation is 120 DEG C.
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Comparative example 5
Carry out obtaining (R)-3-chlorine-1,2-propylene glycol according to the method for embodiment 1, difference is in step 4) in, the temperature of fractionation is 135 DEG C.
Should be consistent by the sign collection of illustrative plates in the data of the nucleus magnetic hydrogen spectrum of (R)-3-chlorine-1,2-propylene glycol and nuclear-magnetism carbon spectrum and embodiment 1.
In the present embodiment, the productive rate of (R)-3-chlorine-1,2-propylene glycol, the parameter of total purity, chiral purity and water ratio ask for an interview table 1.
Table 1
| Total purity (%) | Chiral purity (%) | Water ratio (%) | Productive rate (%) | |
| Embodiment 1 | 99.6 | 99.5 | 0.2 | 98 |
| Embodiment 2 | 99.7 | 99.5 | 0.2 | 99 |
| Embodiment 3 | 99.7 | 99.6 | 0.2 | 98 |
| Embodiment 4 | 99.8 | 99.6 | 0.2 | 97 |
| Embodiment 5 | 99.6 | 99.5 | 0.2 | 98 |
| Embodiment 6 | 99.6 | 99.5 | 0.2 | 98 |
| Embodiment 7 | 99.7 | 99.6 | 0.2 | 97 |
| Comparative example 1 | 85.6 | 63.2 | 1.5 | 78 |
| Comparative example 2 | 78.9 | 59.4 | 0.3 | 64 |
| Comparative example 3 | 76.5 | 70.3 | 0.3 | 75 |
| Comparative example 4 | 81.0 | 71.4 | 0.2 | 72 |
| Comparative example 5 | 82.6 | 72.6 | 0.3 | 68 |
By above-described embodiment and comparative example known, water in neutralise mixt is first removed by method provided by the invention, then under given conditions to filtrate fractionation, thus make this preparation method have excellent productive rate, (the R)-3-chloro-1 simultaneously prepared, 2-propylene glycol has excellent total purity and low water ratio, and especially chiral purity can up to 99.5%.
More than describe the preferred embodiment of the present invention in detail; but the present invention is not limited to the detail in above-mentioned embodiment, within the scope of technical conceive of the present invention; can carry out multiple simple variant to technical scheme of the present invention, these simple variant all belong to protection scope of the present invention.
It should be noted that in addition, each concrete technical characteristic described in above-mentioned embodiment, in reconcilable situation, can be combined by any suitable mode, in order to avoid unnecessary repetition, the present invention illustrates no longer separately to various possible array mode.
In addition, also can carry out arbitrary combination between various different embodiment of the present invention, as long as it is without prejudice to thought of the present invention, it should be considered as content disclosed in this invention equally.
Claims (10)
1. a preparation method for (R)-3-chlorine-1,2-propylene glycol, it is characterized in that, described preparation method comprises:
1) under the existence of an acidic catalyst, (S)-epichlorohydrin and water are carried out ring-opening reaction to obtain open loop mixture;
2) alkali lye and described open loop mixture are carried out neutralization reaction to obtain neutralise mixt;
3) water in described neutralise mixt is removed, then filter to obtain filtrate;
4) described filtrate is carried out at 30-35pa and 125-128 DEG C fractionation with obtained (R)-3-chlorine-1,2-propylene glycol.
2. preparation method according to claim 1, is characterized in that, in step 1) in, described an acidic catalyst be selected from sulfuric acid, phosphoric acid and hydrochloric acid one or more.
3. preparation method according to claim 1 and 2, is characterized in that, in step 1) in, relative to (S)-3-chloro-1 of 100 weight parts, 2-propylene oxide, the consumption of described water is 40-80 weight part, and the consumption of described an acidic catalyst is 0.5-2 weight part.
4. preparation method according to claim 1 and 2, is characterized in that, in step 1) in, described ring-opening reaction meets the following conditions: temperature of reaction is 105-110 DEG C, and the reaction times is 2-6h.
5. preparation method according to claim 1, is characterized in that, in step 2) in, described alkali lye be selected from aqueous sodium hydroxide solution, potassium hydroxide aqueous solution and baryta water one or more.
6. preparation method according to claim 1, is characterized in that, in step 2) in, in described alkali lye, the massfraction of alkali is 3-10%.
7. the preparation method according to claim 1 or 6, is characterized in that, relative to the described open loop mixture of 100 weight parts, the consumption of described alkali lye is 12-20 weight part.
8. preparation method according to claim 1, is characterized in that, in step 2) in, the pH of described neutralise mixt is 6-8.
9. preparation method according to claim 1, is characterized in that, in step 2) in, described neutralization reaction meets the following conditions: temperature of reaction is 15-35 DEG C, and the reaction times is 5-15min.
10. preparation method according to claim 1, is characterized in that, in step 3) in, after being removed by the water in described neutralise mixt, in mixture, water content is 0.1-0.5%.
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| CN106187678A (en) * | 2016-07-07 | 2016-12-07 | 上海科利生物医药有限公司 | A kind of preparation method of (R) 3 chlorine 1,2 propylene glycol |
| CN111943805A (en) * | 2020-09-16 | 2020-11-17 | 安徽工业大学 | Preparation method of (R) -3-chloro-1, 2-propanediol |
| CN113943206A (en) * | 2021-10-25 | 2022-01-18 | 华今(山东)新材料科技有限公司 | Preparation method of high-quality (R) -3-chloro-1, 2-propanediol |
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Cited By (3)
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| CN106187678A (en) * | 2016-07-07 | 2016-12-07 | 上海科利生物医药有限公司 | A kind of preparation method of (R) 3 chlorine 1,2 propylene glycol |
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