CN102746119A - Method for preparing dichlorohydrin from glycerol - Google Patents
Method for preparing dichlorohydrin from glycerol Download PDFInfo
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- CN102746119A CN102746119A CN2011101001440A CN201110100144A CN102746119A CN 102746119 A CN102746119 A CN 102746119A CN 2011101001440 A CN2011101001440 A CN 2011101001440A CN 201110100144 A CN201110100144 A CN 201110100144A CN 102746119 A CN102746119 A CN 102746119A
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- glycerine
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- dichlorohydrine
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 107
- 238000000034 method Methods 0.000 title claims abstract description 23
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 title abstract 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 238000009835 boiling Methods 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 235000011187 glycerol Nutrition 0.000 claims description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 16
- 239000007789 gas Substances 0.000 claims description 15
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 12
- 150000001735 carboxylic acids Chemical class 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 8
- 235000005074 zinc chloride Nutrition 0.000 claims description 8
- 239000011592 zinc chloride Substances 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000001384 succinic acid Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229960003280 cupric chloride Drugs 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000009776 industrial production Methods 0.000 abstract description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- 239000012320 chlorinating reagent Substances 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
- 239000002131 composite material Substances 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- 239000008240 homogeneous mixture Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000009423 ventilation Methods 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000004513 sizing Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MPSXZBZUSOMAQW-UHFFFAOYSA-N acetic acid;prop-1-ene Chemical group CC=C.CC(O)=O MPSXZBZUSOMAQW-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 235000019940 salatrim Nutrition 0.000 description 2
- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 description 1
- CSVFWMMPUJDVKH-UHFFFAOYSA-N 1,1-dichloropropan-2-one Chemical compound CC(=O)C(Cl)Cl CSVFWMMPUJDVKH-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- -1 carboxylate salt Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a method for preparing dichlorohydrin from glycerol, and mainly solves the problems of great catalyst consumption, high production cost, and low dichlorohydrin yield in the prior art. The method of the invention consists of: adopting glycerol and a chlorinating agent as raw materials, and under the conditions of a normal pressure, a reaction temperature of 80-180DEG C, a chlorinating agent dosage of 1-40% of that of the glycerol, and a catalyst dosage of 0.5-20% of that of the glycerol, contacting the raw materials with a catalyst for reaction for 10-50 hours, thus obtaining dichlorohydrin. Specifically, the catalyst comprises the following components by weight: a) 1-95 parts of carboxylic acid with a boiling point higher than or equal to 100DEG C under normal pressure; and b) 5-95 parts of a chloride. The technical scheme adopted in the invention well solves the problem, and can be used in the industrial production of dichlorohydrin from glycerol.
Description
Technical field
The present invention relates to the method that a kind of glycerine prepares dichlorohydrine.
Background technology
Dichlorohydrine DCH is the raw material of multiple Chemicals such as synthetic Dichloro acetone, acetate fiber, water conditioner, also is the midbody of materials such as synthesizing epoxy chloropropane, epoxy resin, ion exchange resin.DCH mainly is as midbody in large-scale industrial application, utilizes alkali lye such as liming that it is carried out saponification, sloughs an one's share of expenses for a joint undertaking HCl, and cyclisation generates epoxy chloropropane (being called for short ECH).ECH is a kind of important Organic Chemicals and fine chemical product, and purposes very extensively.It is strong to be with it that epoxy resin that raw material makes has cohesiveness; Characteristics such as resistant to chemical media burn into shrinking percentage is low, chemicalstability good, excellent in cushion effect and dielectric properties excellence have widely in industries such as coating, sizing agent, strongthener, cast material and electronic shell stampings and to use.In addition, ECH can also be used for multiple products such as synthetic glycerine, nitroglycerine explosive, glass reinforced plastic, electrical isolation article, tensio-active agent, medicine, coating, sizing material, ion exchange resin, softening agent, glycidyl derivatives, chlorohydrin rubber, be used to produce chemical stabilizer, chemical dyestuff and water conditioner etc.The market requirement of DCH is inseparable with ECH.In the consumption of ECH increased, major part was to be applied to synthetic epoxy resin.After getting into 21 century, along with the further increase of industries such as electronics, sizing agent, coating, building to the epoxy resin demand, the epoxy resin demand increases fast, has greatly promoted the development of global ECH.The market requirement of ECH is very vigorous, and tangible ever-increasing trend is arranged, and conventional production methods receives certain limitation again, so the synthetic ECH of exploitation novel process becomes very urgent problem.
The method of dichlorohydrine production at present mainly contains propylene high-temperature chlorination, acetate propylene method and glycerine method.Because facility investment is big when propylene high-temperature chlorination, acetate propylene method suitability for industrialized production; Complex process; Wastewater discharge is big, affects to environment, and especially the propylene high-temperature chlorination obtains trichloropropane and chlorination aliphatic ether and polymkeric substance; Make industrial production cause cost rising and sub product to increase, brought certain limitation to industrial production.
At present many pieces of patent reports are arranged glycerine in the presence of catalyzer such as carboxylic acid, acid anhydrides, sour chlorine, carboxylate salt, generate the method for dichlorohydrine through the hydrogenchloride addition reaction, like document WO2006/020234 and WO2005/054167.The catalyzer that existing bibliographical information is adopted all adopts the bigger organic acid of carboxylic acid, carboxylic acid derivative or volatility, because these catalyzer boiling points are low, catalyst levels is big in the reaction process, and production cost is high; In addition, these catalyzer are water-soluble strong, and are acid strong, and the final product that generates tar has easily perhaps finally become the higher carboxylic acid product of boiling point and has been difficult to evaporation, has reduced the yield of dichlorohydrine.
Summary of the invention
Technical problem to be solved by this invention is that prior art exists catalyst levels big, and production cost is high, and the problem that the dichlorohydrine yield is low provides a kind of new glycerine to prepare the method for dichlorohydrine.This method has that catalyst levels is little, and production cost is low, the characteristics that the dichlorohydrine yield is high.
In order to solve the problems of the technologies described above; The technical scheme that the present invention adopts is following: a kind of glycerine prepares the method for dichlorohydrine, is raw material with glycerine and chlorizating agent, under normal pressure; Temperature of reaction is 80～180 ℃; The chlorizating agent consumption is 1～40% of a glycerine consumption, and catalyst levels is under 0.5～20% condition of glycerine consumption, and raw material and catalyzer contact reacts obtained dichlorohydrine in 10～50 hours; Wherein, said catalyzer comprises following component in parts by weight: a) boiling point is greater than or equal to 100 ℃ carboxylic acid under 1～95 part the normal pressure; B) 5～95 parts muriate.
In the technique scheme, said chlorizating agent is an anhydrous hydrogen chloride gas.Said carboxylic acid preferred version is to be selected from least a in sad, propanedioic acid, Succinic Acid or the hexanodioic acid; Said muriate preferred version is to be selected from least a in zinc chloride, aluminum chloride or the cupric chloride.In parts by weight, the consumption preferable range of carboxylic acid is 30～75 parts, and muriatic consumption preferable range is 25～70 parts.The temperature of reaction preferable range is 90～140 ℃, and chlorizating agent consumption preferable range is 1.5～35% of a glycerine consumption, and the catalyst levels preferable range is 1～12% of a glycerine consumption, and the reaction times preferable range is 15～30 hours.Preferred version is for constantly shifting out the water that reaction generates in the reaction process, makes that the content of water is less than or equal to 15 weight % in the reaction mixture.
Glycerine and hydrogen chloride gas react under the composite catalyst effect, and after its chlorination reaction finished, filtering catalyst was reused, the more refining dichlorohydrine that steams from the reaction gains.
The inventive method is Primary Catalysts through using composite catalyst with the carboxylic acid, is promotor with the muriate; Prepare the reaction mechanism of dichlorohydrine from glycerine, glycerine and carboxylic acid at first carry out esterification, generate short and long-chain acyl triglyceride molecules; Cl ions combines with short and long-chain acyl triglyceride molecules then; Generate glycerine monochlorohydrin, discharge carboxylic acid simultaneously, need a large amount of cl ionss in the reaction process.So the muriatic adding of promotor will promote the substitution reaction of cl ions, the carrying out of accelerated reaction improved the yield of dichlorohydrine, and yield can reach 92%; Simultaneously, can reduce catalyst consumption, reduce production cost, obtain better technical effect.
Through embodiment the present invention is done further elaboration below.
Embodiment
[embodiment 1]
In the four-hole boiling flask that 500 milliliters of bands stir, add 126 gram glycerine and 50 gram catalyzer, under the normal pressure, temperature of reaction is 110 ℃, anhydrous hydrogen chloride gas is fed continuously in the homogeneous mixture solotion of glycerine and catalyzer, carries out blistering reaction.For guaranteeing that gas-liquid two-phase fully contacts, glycerine can transform as much as possible fully, hydrogenchloride ventilation speed is 300 ml/min, under the condition that refluxes, reacts 15 hours, and the HCl gas that reaction is overflowed reclaims with alkali lye.Hexanodioic acid and zinc chloride are composite as catalyzer, and wherein in parts by weight, hexanodioic acid is 70 parts, and zinc chloride is 30 parts.
Reaction result: the yield of dichlorohydrine is 92%.
[embodiment 2]
In the four-hole boiling flask that 500 milliliters of bands stir, add 126 gram glycerine and 25 gram catalyzer, under the normal pressure, temperature of reaction is 90 ℃, anhydrous hydrogen chloride gas is fed continuously in the homogeneous mixture solotion of glycerine and catalyzer, carries out blistering reaction.For guaranteeing that gas-liquid two-phase fully contacts, glycerine can transform as much as possible fully, hydrogenchloride ventilation speed is 300 ml/min, under the condition that refluxes, reacts 15 hours, and the HCl gas that reaction is overflowed reclaims with alkali lye.Hexanodioic acid and aluminum chloride are composite as catalyzer, and wherein in parts by weight, hexanodioic acid is 50 parts, and aluminum chloride is 50 parts.
Reaction result: the yield of dichlorohydrine is 87%.
[comparative example 1]
With [embodiment 1], just catalyst system therefor is merely hexanodioic acid.Reaction result: the yield of dichlorohydrine is 80%.
[embodiment 3]
In the four-hole boiling flask that 500 milliliters of bands stir, add 126 gram glycerine and 75 gram catalyzer, under the normal pressure, temperature of reaction is 140 ℃, anhydrous hydrogen chloride gas is fed continuously in the homogeneous mixture solotion of glycerine and catalyzer, carries out blistering reaction.For guaranteeing that gas-liquid two-phase fully contacts, glycerine can transform as much as possible fully, hydrogenchloride ventilation speed is 300 ml/min, under the condition that refluxes, reacts 30 hours, and the HCl gas that reaction is overflowed reclaims with alkali lye.Propanedioic acid and zinc chloride composite as catalyzer, wherein in parts by weight, propanedioic acid is 30 parts, zinc chloride is 70 parts.
Reaction result: the yield of dichlorohydrine is 86%.
[embodiment 4]
In the four-hole boiling flask that 500 milliliters of bands stir, add 126 gram glycerine and 10 gram catalyzer, under the normal pressure, temperature of reaction is 120 ℃, anhydrous hydrogen chloride gas is fed continuously in the homogeneous mixture solotion of glycerine and catalyzer, carries out blistering reaction.For guaranteeing that gas-liquid two-phase fully contacts, glycerine can transform as much as possible fully, hydrogenchloride ventilation speed is about 300 ml/min, under the condition that refluxes, reacts 20 hours, and the HCl gas that reaction is overflowed reclaims with alkali lye.Propanedioic acid and cupric chloride are composite as catalyzer, and wherein in parts by weight, propanedioic acid is 65 parts, and cupric chloride is 35 parts.
Reaction result: the yield of dichlorohydrine is 82%.
[comparative example 2]
With [embodiment 3], just catalyst system therefor is merely propanedioic acid.Reaction result: the yield of dichlorohydrine is 78%.
[embodiment 5]
In the four-hole boiling flask that 500 milliliters of bands stir, add 1000 gram glycerine and 75 gram catalyzer, under the normal pressure, temperature of reaction is 120 ℃, anhydrous hydrogen chloride gas is fed continuously in the homogeneous mixture solotion of glycerine and catalyzer, carries out blistering reaction.For guaranteeing that gas-liquid two-phase fully contacts, glycerine can transform as much as possible fully, hydrogenchloride ventilation speed is 300 ml/min, under the condition that refluxes, reacts 25 hours, and the HCl gas that reaction is overflowed reclaims with alkali lye.Succinic Acid and zinc chloride are composite as catalyzer, and wherein in parts by weight, Succinic Acid is 55 parts, and zinc chloride is 45 parts.
Reaction result: the yield of dichlorohydrine is 85%.
[embodiment 6]
In the four-hole boiling flask that 500 milliliters of bands stir, add 1000 gram glycerine and 20 gram catalyzer, under the normal pressure, temperature of reaction is 140 ℃, anhydrous hydrogen chloride gas is fed continuously in the homogeneous mixture solotion of glycerine and catalyzer, carries out blistering reaction.For guaranteeing that gas-liquid two-phase fully contacts, glycerine can transform as much as possible fully, hydrogenchloride ventilation speed is 300 ml/min, under the condition that refluxes, reacts 20 hours, and the HCl gas that reaction is overflowed reclaims with alkali lye.Succinic Acid and aluminum chloride are composite as catalyzer, and wherein in parts by weight, Succinic Acid is 45 parts, and aluminum chloride is 65 parts.
Reaction result: the yield of dichlorohydrine is 83%.
[comparative example 3]
With [embodiment 5], just catalyst system therefor is merely Succinic Acid.Reaction result: the yield of dichlorohydrine is 80%.
Claims (6)
1. a glycerine prepares the method for dichlorohydrine; With glycerine and chlorizating agent is raw material; Under normal pressure, temperature of reaction is 80～180 ℃, and the chlorizating agent consumption is 1～40% of a glycerine consumption; Catalyst levels is under 0.5～20% condition of glycerine consumption, and raw material and catalyzer contact reacts obtained dichlorohydrine in 10～50 hours; Wherein, said catalyzer comprises following component in parts by weight: a) boiling point is greater than or equal to 100 ℃ carboxylic acid under 1～95 part the normal pressure; B) 5～95 parts muriate.
2. the method for preparing dichlorohydrine according to the said glycerine of claim 1 is characterized in that said carboxylic acid is selected from least a in sad, propanedioic acid, Succinic Acid or the hexanodioic acid; Said muriate is selected from least a in zinc chloride, aluminum chloride or the cupric chloride.
3. prepare the method for dichlorohydrine according to the said glycerine of claim 1, it is characterized in that said catalyzer in parts by weight, the consumption of carboxylic acid is 30～75 parts, and muriatic consumption is 25～70 parts.
4. the method for preparing dichlorohydrine according to the said glycerine of claim 1 is characterized in that temperature of reaction is 90～140 ℃, and the chlorizating agent consumption is 1.5～35% of a glycerine consumption, and catalyst levels is 1～12% of a glycerine consumption, and the reaction times is 15～30 hours.
5. the method for preparing dichlorohydrine according to the said glycerine of claim 1 is characterized in that said chlorizating agent is an anhydrous hydrogen chloride gas.
6. the method for preparing dichlorohydrine according to the said glycerine of claim 1 is characterized in that constantly shifting out in the reaction process water that reaction generates, and makes that the content of water is less than or equal to 15 weight % in the reaction mixture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101001440A CN102746119A (en) | 2011-04-20 | 2011-04-20 | Method for preparing dichlorohydrin from glycerol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101001440A CN102746119A (en) | 2011-04-20 | 2011-04-20 | Method for preparing dichlorohydrin from glycerol |
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| Publication Number | Publication Date |
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| CN102746119A true CN102746119A (en) | 2012-10-24 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2011101001440A Pending CN102746119A (en) | 2011-04-20 | 2011-04-20 | Method for preparing dichlorohydrin from glycerol |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109516901A (en) * | 2018-12-28 | 2019-03-26 | 山东泰和水处理科技股份有限公司 | A kind of synthetic method of 2,2 '-dichloroether |
| CN114181040A (en) * | 2021-12-14 | 2022-03-15 | 山东鲁泰控股集团有限公司石墨烯高分子复合材料研发中心 | Preparation method of dichloropropanol |
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| CN1976886A (en) * | 2004-07-21 | 2007-06-06 | 陶氏环球技术公司 | Conversion of polyhydroxylated aliphatic hydrocarbons or their esters to chlorohydrins |
| CN101184715A (en) * | 2005-04-18 | 2008-05-21 | 阿塞尔有限责任公司 | A kind of production method of producing α, γ-dichlorohydrin by glycerol and hydrochloric acid |
| CN101773851A (en) * | 2009-01-13 | 2010-07-14 | 德纳（南京）化工有限公司 | Dichloropropanol catalyst prepared by glycerol method |
| CN101921175A (en) * | 2003-11-20 | 2010-12-22 | 索尔维公司 | Process for the production of organic compounds |
-
2011
- 2011-04-20 CN CN2011101001440A patent/CN102746119A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101921175A (en) * | 2003-11-20 | 2010-12-22 | 索尔维公司 | Process for the production of organic compounds |
| CN1976886A (en) * | 2004-07-21 | 2007-06-06 | 陶氏环球技术公司 | Conversion of polyhydroxylated aliphatic hydrocarbons or their esters to chlorohydrins |
| CN101184715A (en) * | 2005-04-18 | 2008-05-21 | 阿塞尔有限责任公司 | A kind of production method of producing α, γ-dichlorohydrin by glycerol and hydrochloric acid |
| CN101773851A (en) * | 2009-01-13 | 2010-07-14 | 德纳（南京）化工有限公司 | Dichloropropanol catalyst prepared by glycerol method |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109516901A (en) * | 2018-12-28 | 2019-03-26 | 山东泰和水处理科技股份有限公司 | A kind of synthetic method of 2,2 '-dichloroether |
| CN114181040A (en) * | 2021-12-14 | 2022-03-15 | 山东鲁泰控股集团有限公司石墨烯高分子复合材料研发中心 | Preparation method of dichloropropanol |
| CN114181040B (en) * | 2021-12-14 | 2023-12-12 | 山东鲁泰控股集团有限公司石墨烯高分子复合材料研发中心 | Preparation method of dichloropropanol |
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Application publication date: 20121024 |