CN103896771A - Method for preparing benzyl acetate by using waste reaction liquid generated in acetate production - Google Patents
Method for preparing benzyl acetate by using waste reaction liquid generated in acetate production Download PDFInfo
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- CN103896771A CN103896771A CN201410114982.7A CN201410114982A CN103896771A CN 103896771 A CN103896771 A CN 103896771A CN 201410114982 A CN201410114982 A CN 201410114982A CN 103896771 A CN103896771 A CN 103896771A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Abstract
The invention relates to the technical field of benzyl acetate synthesis and in particular relates to a method for preparing benzyl acetate by using waste reaction liquid generated in acetate production. Benzyl acetate is prepared by steps of treating the waste reaction liquid, performing acid-base reaction, performing esterification reaction, desalting and rectifying. According to the method, benzyl acetate is prepared from acetic acid in the waste reaction liquid during the acetate production, so that the waste resources can be fully utilized, the resource waste can be reduced, and the environmental pollution caused by the acetate production can be alleviated; in addition, as a raw material is the waste reaction liquid generated in the acetate production, the production cost of benzyl acetate can be greatly reduced and the development requirements of environment-friendly and low-cost synthetic routes can be met; in a process of converting the waste reaction liquid into a reactant, heat emitted in the reaction between acetic acid and sodium hydroxide is fully utilized, the energy consumed for heating a sodium acetate solution is reduced, and the purposes of energy conservation and environmental protection are reached; benzyl acetate with the purity higher than 98% still can be prepared from the waste reaction liquid, and the product quality is ensured.
Description
Technical field
The present invention relates to the synthesis technical field of jasmal, relate in particular to a kind of method of preparing jasmal with the waste reaction solution of producing acetic ester.
Background technology
Jasmal is a kind of batching for essence, has fragrance of a flower fragrance, both can be applicable to cosmetic field, also can be applicable to foodstuff additive field.In addition the fine solvent of jasmal or Synolac, nitrocellulose, dyestuff, grease and printing-ink etc..Jasmal domestic and abroad market prospect is wide, is the synthetic perfume kind of large usage quantity, and the year sales volume of world market in 2010 has reached tens thousand of tons, and demand is still in rising trend.The suitability for industrialized production of jasmal, mainly contains three kinds at present, and the first is for adopting benzylalcohol and acetic acid or diacetyl oxide preparation, this method product has excellent fragrance, but be reaction raw materials owing to adopting acetic acid or acid anhydrides, larger to equipment and environmental influence, production cost is also higher; The second is to adopt by product benzyl oxide and the diacetyl oxide of benzylalcohol to prepare jasmal, and this method products obtained therefrom is strong and brisk in taste, is a kind of high-quality product, but still has the too high deficiency of production cost; The third is Benzyl Chloride and sodium-acetate method, be most economical production line, but product fragrance is slightly poor.Along with the raising of Economic development and environmental protection requirement, design the synthetic syntheti c route of jasmal of high quality, low cost, less contamination by the direction that is development.
Summary of the invention
The technical problem to be solved in the present invention is to provide one and can reduces production costs and environmental pollution simultaneously, and the waste reaction solution that makes full use of production acetic ester is prepared the method for jasmal.
For achieving the above object, the present invention is by the following technical solutions: a kind of method of preparing jasmal with the waste reaction solution of producing acetic ester, comprises the following steps:
(1) waste reaction solution of acetic ester is produced in distillation, collects acetic acid aqueous solution component; In described acetic acid aqueous solution, the mass percent of acetic acid is 20-30%.
(2) in acetic acid aqueous solution, add sodium hydroxide and stir to obtain sodium acetate solution, the mol ratio of described sodium hydroxide and acetic acid is 1-1.02:1, and preferred, and the pH of described sodium acetate solution is 9-13; Then concentrated sodium acetate solution to the mass percent of water is 45-60%; Preferably, sodium acetate solution is heated to 70-90 DEG C and under the vacuum of 0.5-0.7atm underpressure distillation remove portion water.
(3) in sodium acetate solution, add respectively organic solvent, Benzyl Chloride and catalyzer to obtain esterifying liquid, heating esterifying liquid is to 100-120 DEG C and continue stirring until Benzyl Chloride completely dissolve in esterifying liquid and obtain mixed solution; The mol ratio of described sodium acetate and Benzyl Chloride is 1.05-1.2:1, and the quality of described catalyzer is the 0.5-2% of sodium acetate and Benzyl Chloride total amount.
Preferably, described catalyzer is any in Tetrabutyl amonium bromide, tetramethyl ammonium chloride, benzyl triethyl ammonium bromide and triethylamine; Described organic solvent is 2-butyl acetate or N-BUTYL ACETATE.
(4) mixed solution is carried out to desalting treatment, and then product is collected in rectifying.
Described desalting treatment is: mixeding liquid temperature is down to 25-50 DEG C of backward its and is added water jolting, removes water layer after stratification, retains organic layer; Preferably, be the 60-100% of Benzyl Chloride quality to adding the amount of water in mixed solution.Then use successively saturated sodium carbonate solution, saturated nacl aqueous solution and water washing organic layer.
Described rectifying is: heating organic layer is to 80-100 DEG C, and to add quality be the boric acid of organic layer weight 1-5%, then under the vacuum of 0.2-0.5atm, underpressure distillation 2-5h removes light constituent, then the temperature of organic layer is heated to 100-140 DEG C, and product is collected in underpressure distillation under the vacuum of 0.05-0.3atm.
Compared with prior art, the invention has the beneficial effects as follows: the acetic acid that the present invention produces by utilization in the waste reaction solution of acetic ester is prepared jasmal, can make full use of waste resource, reduce the wasting of resources, reduce and produce the environmental pollution bringing because of acetic ester; And because raw material is to produce the waste reaction solution of acetic ester, can reduce greatly the production cost of jasmal, meet synthetic route environmental protection, demand for development cheaply.Be converted into by waste reaction solution in the process of reactant, take full advantage of acetic acid and react institute's liberated heat with sodium hydroxide, reduced the required energy consumption of heating sodium acetate solution, energy-conserving and environment-protective.By preparation technology of the present invention, even taking waste reaction solution as starting material, still can prepare purity higher than 98% jasmal, quality product is protected.
Embodiment
In order to more fully understand technology contents of the present invention, below in conjunction with specific embodiment, technical scheme of the present invention is described further and is illustrated.
Embodiment 1
The waste reaction solution of ethylene glycol bisthioglycolate acetic acid is produced in air distillation, collects the cut of 99.5-118.5 DEG C, i.e. acetic acid aqueous solution component, and in gained acetic acid aqueous solution, the mass percent of acetic acid is 25%.Get the above acetic acid aqueous solution of 1000g and put into reactor, low whipping speed is under 600r/s, slowly add 170g sodium hydroxide and to pH value of solution=13, obtain sodium acetate solution, then heat sodium acetate solution to 80 DEG C, under 0.6atm, carry out underpressure distillation with remove portion water, in the time that the water content of the sodium acetate solution in reactor is 50%, stop underpressure distillation.
In reactor, add successively 70g 2-butyl acetate, 468g Benzyl Chloride and 10.8g Tetrabutyl amonium bromide, and be warming up to immediately 110 DEG C, continue to stir 8h, in detection reaction liquid, without Benzyl Chloride, stopped reaction, obtains mixed solution.
Stop stirring, mixed solution is cooled to 30 DEG C, and adds 400g water to it, after concussion, leave standstill and make liquid layered, remove lower aqueous layer, retain organic layer.Then with isopyknic saturated aqueous sodium carbonate washing organic layer, wash 2 times; Use again isopyknic saturated common salt water washing organic layer, wash 2 times; Finally obtain organic layer with isopyknic deionized water wash.
Heating organic layer to 80 DEG C, and add 8g boric acid, then between 0.2-0.5atm, carry out underpressure distillation 2h, remove light constituent (being the component of its boiling point lower than the boiling point of jasmal); Then organic layer is warming up between 110-120 DEG C, and carry out underpressure distillation between 0.05-0.3atm, collects cut and obtain jasmal finished product, the productive rate of jasmal is 95%, and purity is 98.5%.
Embodiment 2
The waste reaction solution of ethylene glycol bisthioglycolate acetic acid is produced in air distillation, collects the cut of 99.5-118.5 DEG C, i.e. acetic acid aqueous solution component, and in gained acetic acid aqueous solution, the mass percent of acetic acid is 25%.Get the above acetic acid aqueous solution of 1000g and put into reactor, low whipping speed is under 600r/s, slowly add 170g sodium hydroxide and to pH value of solution=13, obtain sodium acetate solution, then heat sodium acetate solution to 80 DEG C, under 0.6atm, carry out underpressure distillation with remove portion water, in the time that the water content of the sodium acetate solution in reactor is 45%, stop underpressure distillation.
In reactor, add successively 70g N-BUTYL ACETATE, 440g Benzyl Chloride and 13.8g Tetrabutyl amonium bromide, and be warming up to immediately 110 DEG C, continue to stir 7h, in detection reaction liquid, without Benzyl Chloride, stopped reaction, obtains mixed solution.
Stop stirring, mixed solution is cooled to 40 DEG C, and adds 380g water to it, after concussion, leave standstill and make liquid layered, remove lower aqueous layer, retain organic layer.Then with isopyknic saturated aqueous sodium carbonate washing organic layer, wash 2 times; Use again isopyknic saturated common salt water washing organic layer, wash 2 times; Finally obtain organic layer with isopyknic deionized water wash.
Heating organic layer to 80 DEG C, and add 10g boric acid, then between 0.2-0.5atm, carry out underpressure distillation 2h, remove light constituent; Then organic layer is warming up between 110-120 DEG C, and carry out underpressure distillation between 0.05-0.3atm, collects cut and obtain jasmal finished product, the productive rate of jasmal is 97%, and purity is 99.1%.
Embodiment 3
The waste reaction solution of ethylene glycol bisthioglycolate acetic acid is produced in air distillation, collects the cut of 99.5-118.5 DEG C, i.e. acetic acid aqueous solution component, and in gained acetic acid aqueous solution, the mass percent of acetic acid is 20%.Get the above acetic acid aqueous solution of 1000g and put into reactor, low whipping speed is under 800r/s, slowly add 135g sodium hydroxide and to pH value of solution=12, obtain sodium acetate solution, then heat sodium acetate solution to 75 DEG C, under 0.5atm, carry out underpressure distillation with remove portion water, in the time that the water content of the sodium acetate solution in reactor is 45%, stop underpressure distillation.
In reactor, add successively 50g jasmal, 380g Benzyl Chloride and 5.1g Tetrabutyl amonium bromide, and be warming up to immediately 110 DEG C, continue to stir 8h, in detection reaction liquid, without Benzyl Chloride, stopped reaction, obtains mixed solution.
Stop stirring, mixed solution is cooled to 50 DEG C, and adds 350g water to it, after concussion, leave standstill and make liquid layered, remove lower aqueous layer, retain organic layer.Then with isopyknic saturated aqueous sodium carbonate washing organic layer; Use again isopyknic saturated common salt water washing organic layer, wash 2 times; Finally obtain organic layer with isopyknic deionized water wash.
Heating organic layer to 80 DEG C, and add 12g boric acid, then between 0.2-0.5atm, carry out underpressure distillation 2h, remove light constituent; Then organic layer is warming up between 110-120 DEG C, and carry out underpressure distillation between 0.05-0.3atm, collects cut and obtain jasmal finished product, the productive rate of jasmal is 92%, and purity is 98.1%.
Embodiment 4
The waste reaction solution of ethylene glycol bisthioglycolate acetic acid is produced in air distillation, collects the cut of 99.5-118.5 DEG C, i.e. acetic acid aqueous solution component, and in gained acetic acid aqueous solution, the mass percent of acetic acid is 20%.Get the above acetic acid aqueous solution of 1000g and put into reactor, low whipping speed is under 800r/s, slowly add 135g sodium hydroxide and to pH value of solution=12, obtain sodium acetate solution, then heat sodium acetate solution to 75 DEG C, under 0.6atm, carry out underpressure distillation with remove portion water, in the time that the water content of the sodium acetate solution in reactor is 45%, stop underpressure distillation.
In reactor, add successively 50g butylacetate, 350g Benzyl Chloride and 8.2g Tetrabutyl amonium bromide, and be warming up to immediately 110 DEG C, continue to stir 8h, in detection reaction liquid, without Benzyl Chloride, stopped reaction, obtains mixed solution.
Stop stirring, mixed solution is cooled to 50 DEG C, and adds 350g water to it, after concussion, leave standstill and make liquid layered, remove lower aqueous layer, retain organic layer.Then with isopyknic saturated aqueous sodium carbonate washing organic layer; Use again isopyknic saturated common salt water washing organic layer, wash 2 times; Finally obtain organic layer with isopyknic deionized water wash.
Heating organic layer to 80 DEG C, and add 10g boric acid, then between 0.2-0.5atm, carry out underpressure distillation 2h, remove light constituent; Then organic layer is warming up between 110-120 DEG C, and carry out underpressure distillation between 0.05-0.3atm, collects cut and obtain jasmal finished product, the productive rate of jasmal is 93%, and purity is 98.9%.
Embodiment 5
The waste reaction solution of ethylene glycol bisthioglycolate acetic acid is produced in air distillation, collects the cut of 99.5-118.5 DEG C, i.e. acetic acid aqueous solution component, and in gained acetic acid aqueous solution, the mass percent of acetic acid is 30%.Get the above acetic acid aqueous solution of 1000g and put into reactor, low whipping speed is under 700r/s, slowly add 200g sodium hydroxide and to pH value of solution=10, obtain sodium acetate solution, then heat sodium acetate solution to 85 DEG C, under 0.7atm, carry out underpressure distillation with remove portion water, in the time that the water content of the sodium acetate solution in reactor is 55%, stop underpressure distillation.
In reactor, add successively 70g butylacetate, 570g Benzyl Chloride and 17.4g Tetrabutyl amonium bromide, and be warming up to immediately 110 DEG C, continue to stir 6h, in detection reaction liquid, without Benzyl Chloride, stopped reaction, obtains mixed solution.
Stop stirring, mixed solution is cooled to 40 DEG C, and adds 500g water to it, after concussion, leave standstill and make liquid layered, remove lower aqueous layer, retain organic layer.Then with isopyknic saturated aqueous sodium carbonate washing organic layer, wash 2 times; Use again isopyknic saturated common salt water washing organic layer, wash 2 times; Finally obtain organic layer with isopyknic deionized water wash.
Heating organic layer to 80 DEG C, and add 15g boric acid, then between 0.2-0.5atm, carry out underpressure distillation 2h, remove light constituent; Then organic layer is warming up between 110-120 DEG C, and carry out underpressure distillation between 0.05-0.3atm, collects cut and obtain jasmal finished product, the productive rate of jasmal is 91%, and purity is 98.3%.
Embodiment 6
The waste reaction solution of ethylene glycol bisthioglycolate acetic acid is produced in air distillation, collects the cut of 99.5-118.5 DEG C, i.e. acetic acid aqueous solution component, and in gained acetic acid aqueous solution, the mass percent of acetic acid is 30%.Get the above acetic acid aqueous solution of 1000g and put into reactor, low whipping speed is under 700r/s, slowly add 200g sodium hydroxide and to pH value of solution=10, obtain sodium acetate solution, then heat sodium acetate solution to 85 DEG C, under 0.7atm, carry out underpressure distillation with remove portion water, in the time that the water content of the sodium acetate solution in reactor is 55%, stop underpressure distillation.
In reactor, add successively 100g jasmal, 530g Benzyl Chloride and 4.15g Tetrabutyl amonium bromide, and be warming up to immediately 110 DEG C, continue to stir 6h, in detection reaction liquid, without Benzyl Chloride, stopped reaction, obtains mixed solution.
Stop stirring, mixed solution is cooled to 40 DEG C, and adds 450g water to it, after concussion, leave standstill and make liquid layered, remove lower aqueous layer, retain organic layer.Then with isopyknic saturated aqueous sodium carbonate washing organic layer, wash 2 times; Use again isopyknic saturated common salt water washing organic layer, wash 2 times; Finally obtain organic layer with isopyknic deionized water wash.
Heating organic layer to 80 DEG C, and add 15g boric acid, then between 0.2-0.5atm, carry out underpressure distillation 2h, remove light constituent; Then organic layer is warming up between 110-120 DEG C, and carry out underpressure distillation between 0.05-0.3atm, collects cut and obtain jasmal finished product, the productive rate of jasmal is 92%, and purity is 98.8%.
The production of other acetic ester, as 1-Methoxy-2-propyl acetate, Isoamyl Acetate FCC, hexalin acetate and meraneine etc., all can obtain acetic acid aqueous solution by distillation processing reaction waste liquid, and then prepare jasmal according to above technique.In other embodiments, can use tetramethyl ammonium chloride, benzyl triethyl ammonium bromide or triethylamine to substitute Tetrabutyl amonium bromide as catalyzer.
In the present invention, productive rate and the purity of processing condition on end product jasmal has vital impact, especially the consumption of catalyzer in esterification, the consumption of water, saturated sodium carbonate solution and saturated nacl aqueous solution in desalting treatment, and in last rectifying, add the amount of boric acid.Find too much or very few productive rate and the purity that all can affect end product of the consumption of each material in each link through repeated multiple times experiment.As shown in following comparative example 1 and comparative example 2.
Comparative example 1
Taking embodiment 2 as reference, difference is: be 14 to adding sodium hydroxide to make the pH that forms sodium acetate solution and make sodium acetate solution in acetic acid aqueous solution, and sodium acetate solution is concentrated into water-content is 30%; In esterification, in reaction system, add 20g, and react 7h at 130 DEG C.All the other processing parameters are identical with embodiment's 2.The productive rate of jasmal is 87%, and purity is 93%.
Comparative example 2
Taking embodiment 2 as reference, difference is: in esterification, in reaction system, add 27g, and react 10h at 130 DEG C.In desalting treatment and rectifying, use respectively saturated sodium carbonate solution and the saturated nacl aqueous solution washing of 0.5 times of volume of organic layer to mix 1 time, then heat organic layer to 70 DEG C, and add 3g boric acid, under 0.2atm, carry out underpressure distillation 2h, remove light constituent; Then organic layer is warming up to 120 DEG C, and carry out underpressure distillation between 0.3atm, collects cut and obtain jasmal finished product.All the other processing parameters are identical with embodiment's 2.The productive rate of jasmal is 82%, and purity is 90%.
The above only further illustrates technology contents of the present invention with embodiment, so that reader is easier to understand, but does not represent that embodiments of the present invention only limit to this, and any technology of doing according to the present invention is extended or recreation, is all subject to protection of the present invention.
Claims (9)
1. a method of preparing jasmal with the waste reaction solution of producing acetic ester, is characterized in that, comprises the following steps:
The waste reaction solution of acetic ester is produced in S1, distillation, collects acetic acid aqueous solution component;
S2, in acetic acid aqueous solution, add sodium hydroxide and stir to obtain sodium acetate solution, the mol ratio of described sodium hydroxide and acetic acid is 1-1.02:1; Then concentrated sodium acetate solution to the mass percent of water is 45-60%;
S3, in sodium acetate solution, add respectively organic solvent, Benzyl Chloride and catalyzer to obtain esterifying liquid, heating esterifying liquid is to 100-120 DEG C and continue stirring until Benzyl Chloride completely dissolve in esterifying liquid and obtain mixed solution; The mol ratio of described sodium acetate and Benzyl Chloride is 1.05-1.2:1, and the quality of described catalyzer is the 0.5-2% of sodium acetate and Benzyl Chloride total amount;
S4, mixed solution is carried out to desalting treatment, and then product is collected in rectifying.
2. a kind of method with producing the waste reaction solution of acetic ester and prepare jasmal according to claim 1, it is characterized in that, described desalting treatment is: mixeding liquid temperature is down to 25-50 DEG C of backward its and is added water jolting, removes water layer after stratification, retains organic layer; Then use successively saturated sodium carbonate solution, saturated nacl aqueous solution and water washing organic layer.
3. a kind of method with producing the waste reaction solution of acetic ester and prepare jasmal according to claim 2, is characterized in that, is 60-100% the jolting of Benzyl Chloride quality to adding the amount of water in mixed solution.
4. a kind of method with producing the waste reaction solution of acetic ester and prepare jasmal according to claim 2, it is characterized in that, described rectifying is: heating organic layer is to 80-100 DEG C, and to add quality be the boric acid of organic layer weight 1-5%, then under the vacuum of 0.2-0.5atm, underpressure distillation 2-5h removes light constituent, then the temperature of organic layer is heated to 100-140 DEG C, and product is collected in underpressure distillation under the vacuum of 0.05-0.3atm.
5. a kind of method with producing the waste reaction solution of acetic ester and prepare jasmal according to claim 4, is characterized in that: in described step S2, by sodium acetate solution be heated to 70-90 DEG C and under the vacuum of 0.5-0.7atm underpressure distillation remove portion water.
6. a kind of method with producing the waste reaction solution of acetic ester and prepare jasmal according to claim 5, is characterized in that: the pH before described sodium acetate solution is concentrated is 9-13.
7. a kind of method with producing the waste reaction solution of acetic ester and prepare jasmal according to claim 6, is characterized in that: in step S1, in described acetic acid aqueous solution, the mass percent of acetic acid is 20-30%.
8. a kind of method with producing the waste reaction solution of acetic ester and prepare jasmal according to claim 7, is characterized in that: described catalyzer is any in Tetrabutyl amonium bromide, tetramethyl ammonium chloride, benzyl triethyl ammonium bromide and triethylamine.
9. a kind of method with producing the waste reaction solution of acetic ester and prepare jasmal according to claim 8, is characterized in that: described organic solvent is 2-butyl acetate or N-BUTYL ACETATE.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104275195A (en) * | 2014-10-11 | 2015-01-14 | 江苏常州酞青新材料科技有限公司 | Preparation method of benzyl acetate catalyst |
| CN105646212A (en) * | 2016-01-20 | 2016-06-08 | 浙江大学 | Method for treating isobutyrate containing waste water through alkyl halide esterification method |
| CN105712874A (en) * | 2016-01-20 | 2016-06-29 | 宁波永顺精细化工有限公司 | Method for treating isobutyrate-containing wastewater by alcohol etherification |
| CN110903196A (en) * | 2018-09-15 | 2020-03-24 | 天津大加化工有限公司 | Production process of benzyl acetate |
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2014
- 2014-03-25 CN CN201410114982.7A patent/CN103896771A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104275195A (en) * | 2014-10-11 | 2015-01-14 | 江苏常州酞青新材料科技有限公司 | Preparation method of benzyl acetate catalyst |
| CN105646212A (en) * | 2016-01-20 | 2016-06-08 | 浙江大学 | Method for treating isobutyrate containing waste water through alkyl halide esterification method |
| CN105712874A (en) * | 2016-01-20 | 2016-06-29 | 宁波永顺精细化工有限公司 | Method for treating isobutyrate-containing wastewater by alcohol etherification |
| CN105712874B (en) * | 2016-01-20 | 2017-12-22 | 宁波永顺精细化工有限公司 | The method that alcohol esterification method handles the waste water containing isobutyrate |
| CN105646212B (en) * | 2016-01-20 | 2018-04-06 | 浙江大学 | The method that alkyl halide esterification process handles the waste water containing isobutyrate |
| CN110903196A (en) * | 2018-09-15 | 2020-03-24 | 天津大加化工有限公司 | Production process of benzyl acetate |
| CN110903196B (en) * | 2018-09-15 | 2022-05-10 | 天津大加化工有限公司 | Production process of benzyl acetate |
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Effective date of registration: 20160819 Address after: 519000 Guangdong province Zhuhai Gaolan Port Economic Zone Petrochemical Zone five North Road Feiyang chemical plant Applicant after: ZHUHAI FEIYANG NOVEL MATERIALS Corp.,Ltd. Address before: 519000 Guangdong province Zhuhai Gaolan Port Economic Zone Petrochemical Zone five North Road Feiyang chemical plant Applicant before: ZHUHAI FEIYANG NOVEL MATERIALS Corp.,Ltd. Applicant before: SHENZHEN FEIYANG JUNYAN NEW MATERIAL CO.,LTD. |
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