CN103848742B - The method of High-efficient Production diethylene glycol dibenzoate - Google Patents
The method of High-efficient Production diethylene glycol dibenzoate Download PDFInfo
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- CN103848742B CN103848742B CN201310701995.XA CN201310701995A CN103848742B CN 103848742 B CN103848742 B CN 103848742B CN 201310701995 A CN201310701995 A CN 201310701995A CN 103848742 B CN103848742 B CN 103848742B
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- Prior art keywords
- phenylformic acid
- product
- reactor
- evacuated
- diethylene glycol
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- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 48
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 32
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000005406 washing Methods 0.000 claims abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 15
- 238000001035 drying Methods 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 8
- 239000011734 sodium Substances 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000000047 product Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 5
- 206010013786 Dry skin Diseases 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 3
- 239000004902 Softening Agent Substances 0.000 abstract description 6
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 abstract description 2
- FJRUWRJAJNEIKD-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-6,7-diamine Chemical compound O1CCOC2=C1C=C(N)C(N)=C2 FJRUWRJAJNEIKD-UHFFFAOYSA-N 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 230000001588 bifunctional effect Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
Abstract
The method of High-efficient Production diethylene glycol dibenzoate, its technical process weighs phenylformic acid and glycol ether and catalyst sulfuric acid hydrogen sodium input reactor in proportion to refine, to be evacuated to again in another and still adds the NaOH aqueous solution and neutralizes, treat that layering after washing, again layering rear decoloring are washed again, drying, after filtering, inspection obtains finished product.The invention discloses a kind of take sodium pyrosulfate as catalyzer is in the reactor of 5.5 cubic metres at a volume, produces the softening agent of 4.5 tons of high-quality or claims DEDB.
Description
Technical field
The present invention relates to chemical field, particularly the method for High-efficient Production diethylene glycol dibenzoate.
Background technology
China's softening agent purposes is wide, and output is large, and the softening agent of nearly 80% is o-benzoate class, as DOP, DBP etc.After DOP is had carcinogenesis by american cancer institute (NCI) suspection, the states such as America and Europe start restriction and use.China also specifies, all products relevant with food, medicine, toy etc. can not use adjacent stupid diformic ester softening agent.
DEDB is a kind of new non-toxic plasticizer of China's Development and Production in this year.Raw materials for production are phenylformic acid and glycol ether, and its price is cheap compared with the raw material of DOP.
It for most of emulsion particularly VAE and PVAC have splendid consistency and the reaction of good viscosity and stability can be provided, it can reduce resin glass temperature and provide suitable beginning and bonding time.
The consistency of DEDB and PVC is all better than other a kind of softening agent, and DOP can be replaced to make the primary plasticizer of PVC.
But the domestic and international production about softening agent (DEDB) is at present also not enough with research, and production efficiency and mass difference are very far away.
Summary of the invention
In order to overcome the above-mentioned shortcoming of prior art, the object of this invention is to provide high efficiency, the method for the High-efficient Production diethylene glycol dibenzoate of high yield.
The technical solution adopted for the present invention to solve the technical problems is: the method for High-efficient Production diethylene glycol dibenzoate, and its technical process is as follows:
1) weigh: take phenylformic acid, glycol ether and catalyst sulfuric acid hydrogen sodium and drop in reactor, the mol ratio of phenylformic acid and glycol ether is 2.1:1, and catalyst sulfuric acid hydrogen sodium is 0.3% of total weight of material; Pass into heat-conducting oil heating, after determining that phenylformic acid all dissolves, start stirring;
2) esterification: when being heated to 170 DEG C ~ 180 DEG C, have water and steam with the phenylformic acid distilled, when temperature rises to 200 DEG C ~ 210 DEG C fast, now, reaction completes, and stops heating;
3) neutralize: with cooling thermal oil cooling reaction mass, when reactor temperature is down to 100 DEG C, through pipeline from extraction material bottom reactor is delivered to and still; With in the NaOH aqueous solution of 70 DEG C 5% and the complete phenylformic acid of unreacted, be adjusted to PH=8;
4) wash: in still to be neutralized after reaction mass layering, lower coarse product is evacuated to a washing kettle and washes, now, PH=7.3;
5) decolouring is washed again: lower coarse product after the rear reaction mass layering of a washing kettle washing, then is evacuated to another washing kettle by crude product again, uses H
2o
2decolouring, then wash.
6) dry: after again water washed after reaction mass layering, lower floor's product is evacuated to drying kettle, in 120 DEG C ~ 130 DEG C heat dryings;
7) filter: filter to obtain water white diethylene glycol dibenzoate through dried product.
As a further improvement on the present invention: the esterification of described production method is a kind of reversible reaction, and byproduct of reaction is water, and water byproduct, as removed not in time, is reacted and walked back to reverse.
As a further improvement on the present invention: described glycol ether is bifunctional molecules, and phenylformic acid is monofuntional molecule, take glycol ether and benzoic mol ratio is 1:1, reaction gained be mono-ester product.
As a further improvement on the present invention: described glycol ether is bifunctional molecules, and phenylformic acid is monofuntional molecule, take glycol ether and benzoic mol ratio is 2:1, what be obtained by reacting is dibasic acid esters product.
As a further improvement on the present invention: the catalyzer of selecting of described esterification has: sulfuric acid, phosphoric acid, tosic acid.
As a further improvement on the present invention: reactor is being provided with prolong, prolong end is provided with extraction sector water byproduct can taken away in time.
Compared with prior art, the invention has the beneficial effects as follows: the product that the present invention produces is a kind of new non-toxic plasticizer (DEDB).Raw materials for production are phenylformic acid and glycol ether, and its price is cheap compared with the raw material of DOP.For most of emulsion particularly VAE and PVAC have splendid consistency, and good year can be provided to react extremely stability.Adopt the DEDB output capacity of the present invention's production up to 95%, substantially increase the efficiency of production.
Embodiment
Now the present invention is further described in conjunction with the embodiments:
The method of High-efficient Production diethylene glycol dibenzoate, its technical process is as follows:
1) weigh: take phenylformic acid, glycol ether and catalyst sulfuric acid hydrogen sodium and drop in reactor, the mol ratio of phenylformic acid and glycol ether is 2.1:1, and catalyst sulfuric acid hydrogen sodium is 0.3% of total weight of material; Pass into heat-conducting oil heating, after determining that phenylformic acid all dissolves, start stirring;
2) esterification: when being heated to 170 DEG C ~ 180 DEG C, have water and steam with the phenylformic acid distilled, when temperature rises to 200 DEG C ~ 210 DEG C fast, now, reaction completes, and stops heating;
3) neutralize: with cooling thermal oil cooling reaction mass, when reactor temperature is down to 100 DEG C, through pipeline from extraction material bottom reactor is delivered to and still; With in the NaOH aqueous solution of 70 DEG C 5% and the complete phenylformic acid of unreacted, be adjusted to PH=8;
4) wash: in still to be neutralized after reaction mass layering, lower coarse product is evacuated to a washing kettle and washes, now, PH=7.3;
5) decolouring is washed again: lower coarse product after the rear reaction mass layering of a washing kettle washing, then is evacuated to another washing kettle by crude product again, uses H
2o
2decolouring, then wash.
6) dry: after again water washed after reaction mass layering, lower floor's product is evacuated to drying kettle, in 120 DEG C ~ 130 DEG C heat dryings;
7) filter: filter to obtain water white diethylene glycol dibenzoate through dried product.
The esterification of described production method is a kind of reversible reaction, and byproduct of reaction is water, and water byproduct, as removed not in time, is reacted to reverse and walked back, and reaction formula is as follows:
Described glycol ether is bifunctional molecules, and phenylformic acid is monofuntional molecule, takes glycol ether and benzoic mol ratio is 1:1, reaction gained be mono-ester product.
Described glycol ether is bifunctional molecules, and phenylformic acid is monofuntional molecule, takes glycol ether and benzoic mol ratio is 2:1, and what be obtained by reacting is dibasic acid esters product.
The catalyzer of selecting of described esterification has: sulfuric acid, phosphoric acid, tosic acid.
Reactor is being provided with prolong, and prolong end is provided with extraction sector water byproduct can taken away in time.
Described technical process and reaction principle are applied to the benzoic ether of High-efficient Production di-alcohol dibenzoate or a kind of polyvalent alcohol.
The present invention selects sodium pyrosulfate to make catalysts, Gu it has certain corrodibility, whole production unit all adopts 304 stainless steels to make reactor, with the heating of thermal oil inner coil pipe to prepare control temperature.Suitably bleed at the prolong end going out to arrange close to reactor, so that water byproduct is once namely generation is pumped.When washing, adopt the temperature of hot water better about 70 DEG C effects.
Repeatedly produce and determine that the mol ratio of phenylformic acid and two sweet acid is 2.1:1, i.e. phenylformic acid excessive 5%, to ensure product height double esterification reaction.When temperature of reaction reaches 180 DEG C, start normally have water to steam, when 200 DEG C, reaction completes substantially, finally obtains the output capacity of product up to 95%.
Case study on implementation:
Drop into 3.87 tons, phenylformic acid in a kettle., glycol ether 1.6 tons, catalyst sulfuric acid hydrogen sodium 16kg.Heat pipe passes into heat-conducting oil heating, after determining that phenylformic acid all dissolves, starts stirring.During heating temperatures to 180 DEG C, there is water and steam with the phenylformic acid distilled.When the water flowed out is little, temperature rises to 200 DEG C fast.Now, can think that reaction completes substantially, stop heating.With cooling thermal oil pass into heat pipe cooling reaction mass, when reactor temperature is down to 100 DEG C, through pipeline extract out bottom reactor deliver to and still.With in the NaOH aqueous solution of 70 DEG C 5% and the complete phenylformic acid of unreacted, be adjusted to PH=8.After the layering of question response thing, lower coarse product is evacuated to a washing kettle and washes, now PH=7.3.After layering, lower coarse product is evacuated to another washing kettle again after water washed, uses H
20
2decolouring, then wash.Water washed rear layering show that lower floor's product pumps it to drying kettle again.At drying kettle in about 120 DEG C heat dryings.Dry filter obtains water white diethylene glycol dibenzoate 4.5 tons, and output capacity is 95%, send analysis, and packaging is dispatched from the factory.
The physical parameter of product diethylene glycol dibenzoate (DEDB) must be gone out:
Other case study on implementation produce with different catalyzer, selects catalyzer to have: sulfuric acid, phosphoric acid, tosic acid.
In sum, after those of ordinary skill in the art reads file of the present invention, make other various corresponding conversion scheme according to technical scheme of the present invention and technical conceive without the need to creative brainwork, all belong to the scope that the present invention protects.
Claims (1)
1. the method for High-efficient Production diethylene glycol dibenzoate, its technical process is as follows:
1) weigh: take phenylformic acid, glycol ether and catalyst sulfuric acid hydrogen sodium and drop in reactor, the mol ratio of phenylformic acid and glycol ether is 2.1:1, and catalyst sulfuric acid hydrogen sodium is 0.3% of total weight of material; Pass into heat-conducting oil heating, after determining that phenylformic acid all dissolves, start stirring;
2) esterification: when being heated to 170 DEG C, have water and steam with the phenylformic acid distilled, when temperature rises to 200 DEG C fast, now, reaction completes, and stops heating;
3) neutralize: with cooling thermal oil cooling reaction mass, when reactor temperature is down to 100 DEG C, through pipeline from extraction material bottom reactor is delivered to and still; With in the NaOH aqueous solution of 70 DEG C 5% and the complete phenylformic acid of unreacted, be adjusted to PH=8;
4) wash: in still to be neutralized after reaction mass layering, lower coarse product is evacuated to a washing kettle and washes, now, PH=7.3;
5) decolouring is washed again: lower coarse product after the rear reaction mass layering of a washing kettle washing, then is evacuated to another washing kettle by crude product again, uses H
2o
2decolouring, then wash;
6) dry: after again water washed after reaction mass layering, lower floor's product is evacuated to drying kettle, in 120 DEG C of DEG C of heat dryings;
7) filter: filter to obtain water white diethylene glycol dibenzoate through dried product.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310701995.XA CN103848742B (en) | 2013-12-19 | 2013-12-19 | The method of High-efficient Production diethylene glycol dibenzoate |
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| CN201310701995.XA CN103848742B (en) | 2013-12-19 | 2013-12-19 | The method of High-efficient Production diethylene glycol dibenzoate |
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| Publication Number | Publication Date |
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| CN103848742A CN103848742A (en) | 2014-06-11 |
| CN103848742B true CN103848742B (en) | 2016-04-27 |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101376631A (en) * | 2008-10-07 | 2009-03-04 | 杭州临安商通塑化有限公司 | Environment-protective preparation of diglycol ethylene dibenzoate plasticiser |
| CN101407461A (en) * | 2008-11-03 | 2009-04-15 | 华东师范大学 | Preparation method of diethylene glycol dibenzoate |
| CN101492372A (en) * | 2008-12-01 | 2009-07-29 | 无锡双象化学工业有限公司 | Method for producing elasticizer diethylene glycol dibenzoate |
| CN101987819A (en) * | 2009-08-07 | 2011-03-23 | 成都亚恩科技实业有限公司 | Method for preparing diethylene glycol dibenzoate plasticizer |
| CN103012152A (en) * | 2013-01-17 | 2013-04-03 | 岑溪市祥胜化工有限公司 | Production technique of diethylene glycol dibenzoate |
| CN103086891A (en) * | 2013-02-22 | 2013-05-08 | 厦门大学 | Preparation method of plasticizer diethylene glycol dibenzoate |
-
2013
- 2013-12-19 CN CN201310701995.XA patent/CN103848742B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101376631A (en) * | 2008-10-07 | 2009-03-04 | 杭州临安商通塑化有限公司 | Environment-protective preparation of diglycol ethylene dibenzoate plasticiser |
| CN101407461A (en) * | 2008-11-03 | 2009-04-15 | 华东师范大学 | Preparation method of diethylene glycol dibenzoate |
| CN101492372A (en) * | 2008-12-01 | 2009-07-29 | 无锡双象化学工业有限公司 | Method for producing elasticizer diethylene glycol dibenzoate |
| CN101987819A (en) * | 2009-08-07 | 2011-03-23 | 成都亚恩科技实业有限公司 | Method for preparing diethylene glycol dibenzoate plasticizer |
| CN103012152A (en) * | 2013-01-17 | 2013-04-03 | 岑溪市祥胜化工有限公司 | Production technique of diethylene glycol dibenzoate |
| CN103086891A (en) * | 2013-02-22 | 2013-05-08 | 厦门大学 | Preparation method of plasticizer diethylene glycol dibenzoate |
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| CN103848742A (en) | 2014-06-11 |
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Effective date of registration: 20240125 Address after: 438000 Ditang village, yangyinling, Huangzhou Railway Station Development Zone, Huanggang City, Hubei Province Patentee after: Wuhan yikede Fine Chemical Co.,Ltd. Guo jiahuodiqu after: Zhong Guo Address before: No. 69, Gangtai Road, Gangzaidi, Changgang Village, Jianggao Town, Baiyun District, Guangzhou City, Guangdong Province, 510000 Patentee before: GUANGZHOU ZHENGDAO ENVIRONMENTAL PROTECTION NEW Co.,Ltd. Guo jiahuodiqu before: Zhong Guo |