CN107868100A - A kind of synthesis compound method of urea propyl-triethoxysilicane methanol solution - Google Patents
A kind of synthesis compound method of urea propyl-triethoxysilicane methanol solution Download PDFInfo
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- CN107868100A CN107868100A CN201610852101.0A CN201610852101A CN107868100A CN 107868100 A CN107868100 A CN 107868100A CN 201610852101 A CN201610852101 A CN 201610852101A CN 107868100 A CN107868100 A CN 107868100A
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- Prior art keywords
- urea
- triethoxysilicane
- urea propyl
- reaction
- propyl
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 239000004202 carbamide Substances 0.000 title claims abstract description 54
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 14
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 title claims description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 239000002994 raw material Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 6
- 230000001681 protective effect Effects 0.000 claims description 6
- 239000003337 fertilizer Substances 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 2
- WTHDKMILWLGDKL-UHFFFAOYSA-N urea;hydrate Chemical compound O.NC(N)=O WTHDKMILWLGDKL-UHFFFAOYSA-N 0.000 claims description 2
- XQGWAPPLBJZCEV-UHFFFAOYSA-N triethoxy(propyl)silane;urea Chemical compound NC(N)=O.CCC[Si](OCC)(OCC)OCC XQGWAPPLBJZCEV-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 8
- 229910021529 ammonia Inorganic materials 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 235000019441 ethanol Nutrition 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000005070 sampling Methods 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- 150000003673 urethanes Chemical class 0.000 description 5
- 238000002479 acid--base titration Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- -1 aminopropyl Chemical group 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000005909 ethyl alcohol group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000021393 food security Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C1/00—Ammonia; Compounds thereof
- C01C1/16—Halides of ammonium
- C01C1/164—Ammonium chloride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
The present invention relates to a kind of synthesis of urea propyl-triethoxysilicane methanol solution preparation, category organic chemical industry field.The present invention is pressed using urea and aminopropyl triethoxysilane and urea propyl-triethoxysilicane and accessory substance ammonia is generated under certain reaction condition；The accessory substance ammonia watery hydrochloric acid generated in course of reaction is absorbed into aqueous ammonium chloride solution；Should after the completion of urea propyl-triethoxysilicane be configured to the solution containing methanol 0% 80%.The invention simple production process, not only production cost is low, and product yield is high, and pollution-free, environmental protection.The present invention relates to a kind of synthesis of urea propyl-triethoxysilicane methanol solution preparation, category organic chemical industry field.The present invention is pressed using urea and aminopropyl triethoxysilane and urea propyl-triethoxysilicane and accessory substance ammonia is generated under certain reaction condition；The accessory substance ammonia watery hydrochloric acid generated in course of reaction is absorbed into aqueous ammonium chloride solution；Urea propyl-triethoxysilicane after the completion of reaction is configured to the solution containing methanol 0% 80%.The invention simple production process, not only production cost is low, and product yield is high, and pollution-free, more environmentally friendly.
Description
Technical field
The present invention relates to a kind of synthesis of urea propyl-triethoxysilicane-methanol solution preparation, category organic chemical industry field.
Background technology
As a kind of special organo silane coupling agent, it is mainly used in polyvinyl chloride, gathered urea propyl-triethoxysilicane
The adhesion promoters of styrene, polyamide；For epoxy resin, phenolic resin, melamine resin adhesive；It is used
In glass fibre as size and surface conditioning agent, the binding agent of mineral wool is also used for；It is exclusively used in foundry resin, is casting
With sand mold and the binding agent of wear-resisting abrasive wheel.Urea propyl-triethoxysilicane is nineteen sixty-eight earliest in United States Patent (USP) US3671562
In put forward, but limited by economic and technique level at that time, the application of urea propyl-triethoxysilicane is also by very big limit
System.With industrial expansion, the appearance successively of various new materials, organo silane coupling agent is widely applied, urea propyl group three
Industrialized production has also been done step-by-step in Ethoxysilane.
It is first to use urethanes and the ethoxy of aminopropyl three to produce and prepare urea propyl-triethoxysilicane method at present
Base silane generates urea propyl-triethoxysilicane and ethanol in solvent and organotin catalyzed lower reaction, then distills out reaction life
Into second alcohol and solvent, obtain urea propyl-triethoxysilicane sterling, the methanol solution of different content finally converted into methanol.Day
This patent Unexamined Patent 8-333375-1996 has similar report.
It is very inconvenient when in use because product urea propyl-triethoxysilicane is solid at normal temperatures, so most producer
Sell and use after urea propyl-triethoxysilicane directly is converted into methanol solution, such as Degussa Dynasylan 2201 and Mai Tu
A-1160 etc..The synthesis technique is simple, and reaction condition is gentle, and product quality and yield are all very high, have industrially used very
Long a period of time.But as the developed countries such as USA and EU increasingly close to environmental protection, food security, health etc.
Note, successively discloses some high attention rate materials that may be had an impact to environment or health etc., wherein there is production urea third
The raw material urethanes of ethyl triethoxy silicane alkane so that the production technology can not increasingly meet environment and the need in market
Ask, following some deficiencies in the synthetic method be present：
1. there is micro carbamic acid in the urea propyl-triethoxysilicane product produced after testing using this production technology
The residual of ethyl ester, micro urethanes may influence health；
2. the catalyst organotin residual added when producing urea propyl-triethoxysilicane is in the product, client is using
When can influence performance, cause the change of the physicochemical properties such as xanthochromia rate, electrical conductivity；
3. the solvent used during the technique productions urea propyl-triethoxysilicane is benzene mostly, first benezene material, such thing
Matter is strong carcinogen, is had a great impact to health；
4. raw material urethanes price is high, dosage is big, makes production cost height.
The content of the invention
The present invention is directed to above-mentioned production technology produced problem, there is provided one kind has product yield high, and environmental pollution is small, raw
Low cost and other advantages are produced, and are adapted to the synthesis compound method of urea propyl-triethoxysilicane-methanol solution of industrialized production.
A kind of synthesis compound method of urea propyl-triethoxysilicane-methanol solution, it is characterised in that：It includes following step
Suddenly：
1) urea, is subjected to azeotropic distillation dewater treatment with absolute ethyl alcohol first, makes the urea water content after dewater treatment
Less than 0.03%, the ethanol water content after distillation is 0.2%, can make other industrial uses；Then by urea and the second of aminopropyl three
TMOS raw material presses 1：3.68 weight ratio, first aminopropyl triethoxysilane raw material is pumped into the reactor with stirring,
And urea raw material is put into reactor in the case where stirring nitrogen protective condition；
2) after the completion of, urea raw material feeds intake, reactor is warming up to 120 DEG C -130 DEG C in the case where stirring nitrogen protective condition,
125 DEG C of optimal reaction temperature；Reacted 4 hours under normal pressure；
3), synthesis under normal pressure opens water circulation vavuum pump and continues reaction 4 hours under -0.09MPa vacuum after 4 hours；
Tail gas in whole course of reaction is absorbed with dilute hydrochloric acid solution, and the aqueous ammonium chloride solution of generation can do agricultural fertilizer use；
4), continue within 4 hours after completion of the reaction, kettle temperature to be dropped into 45 DEG C -50 DEG C under nitrogen protective condition, obtains the second of urea propyl group three
TMOS sterling, then quantitative methanol is pumped into, obtain methanol content 0%-80% urea propyl-triethoxysilicane-methanol solution
Finished product；
The complete ethoxy of raw material aminopropyl three of unreacted in the urea propyl-triethoxysilicane sterling that the synthesis technique is produced
Base silane gas chromatographic detection (GC) content is less than 2%, and amine value is less than 0.2% with acid-base titration detection, uses gel infiltration
Chromatogram (GPC) analysis product purity is more than 97.5%, and polymer content is less than 0.2%.
The beneficial effect of the present invention compared with prior art is：
1) urethanes is instead of with raw material urea when feeding intake, dosage is less, and cost is lower, more environmentally friendly；
2) reaction is not required to add solvent and catalyst in addition, reduces production cost；
3) accessory substance ammonia is absorbed into aqueous ammonium chloride solution with watery hydrochloric acid, is a kind of raw material of agricultural fertilizer, without waste gas
Discharge, will not be polluted to environment；
4) methanol solution of arbitrary proportion can be configured to.
Embodiment
Embodiment 1：
100 grams of urea and 100 grams of absolute ethyl alcohols are added in equipped with churned mechanically 1000ml three-necked flasks, will under stirring
Kettle temperature is raised to 78-83 DEG C, and whole ethanol is distilled out under normal pressure, obtains the recovery ethanol that 99 grams of water content are 0.17%.The second
Alcohol can make other industrial uses.The water content of urea is 0.02% in sampling detection flask.To flask under stirring and nitrogen protection
368 grams of aminopropyl triethoxysilanes of interior addition, are raised to 120 DEG C, tail gas is absorbed with diluted hydrochloric acid aqueous solution by reaction temperature.Reaction
Water circulation vavuum pump is opened after 4 hours, continues reaction 4 hours at 120 DEG C of -0.09MPa vacuums.After completion of the reaction, will be anti-
Kettle nitrogen is answered to cool to 50 DEG C under protecting, sampling detects the aminopropyl triethoxysilane content that unreacted is complete in product and is
1.85% (GC), amine value are 0.19% (acid-base titration), and urea propyl-triethoxysilicane content is 97.7% (GPC), polymerization
Thing content is 0.16% (GPC).The product is urea propyl-triethoxysilicane sterling, methanol content 0%, is at room temperature white
Waxy solid.
Embodiment 2：
100 grams of urea and 100 grams of absolute ethyl alcohols are added in equipped with churned mechanically 1000ml three-necked flasks, will under stirring
Kettle temperature is raised to 78-83 DEG C, and whole ethanol is distilled out under normal pressure, obtains the recovery ethanol that 98 grams of water content are 0.18%.The second
Alcohol can make other industrial uses.The water content of urea is 0.017% in sampling detection flask.To flask under stirring and nitrogen protection
368 grams of aminopropyl triethoxysilanes of interior addition, are raised to 130 DEG C, tail gas is absorbed with diluted hydrochloric acid aqueous solution by reaction temperature.Reaction
Water circulation vavuum pump is opened after 4 hours, continues reaction 4 hours at 130 DEG C of -0.09MPa vacuums.After completion of the reaction, will be anti-
Kettle nitrogen is answered to cool to 45 DEG C under protecting, sampling detects the aminopropyl triethoxysilane content that unreacted is complete in product and is
1.80% (GC), amine value are 0.17% (acid-base titration), and urea propyl-triethoxysilicane content is 97.8% (GPC), polymerization
Thing content is 0.15% (GPC).439 grams of absolute methanols are added thereto, obtain 878 grams of urea propyl-triethoxysilicane-methanol
Solution, it is 50% (baking) to detect its methanol volatile content.
Embodiment 3：
100 grams of urea and 100 grams of absolute ethyl alcohols are added in equipped with churned mechanically 2000ml three-necked flasks, will under stirring
Kettle temperature is raised to 78-83 DEG C, and whole ethanol is distilled out under normal pressure, obtains the recovery ethanol that 98 grams of water content are 0.16%.The second
Alcohol can make other industrial uses.The water content of urea is 0.018% in sampling detection flask.To flask under stirring and nitrogen protection
368 grams of aminopropyl triethoxysilanes of interior addition, are raised to 125 DEG C, tail gas is absorbed with diluted hydrochloric acid aqueous solution by reaction temperature.Reaction
Water circulation vavuum pump is opened after 4 hours, continues reaction 4 hours at 125 DEG C of -0.09MPa vacuums.After completion of the reaction, will be anti-
Kettle nitrogen is answered to cool to 50 DEG C under protecting, sampling detects the aminopropyl triethoxysilane content that unreacted is complete in product and is
1.81% (GC), amine value are 0.16% (acid-base titration), and urea propyl-triethoxysilicane content is 97.8% (GPC), polymerization
Thing content is that 0.16% (GPC) adds 1756 grams of absolute methanols thereto, obtains 2193 grams of urea propyl-triethoxysilicane-first
Alcoholic solution, it is 80% (baking) to detect its methanol volatile content.
Claims (3)
1. a kind of synthesis compound method of urea propyl-triethoxysilicane-methanol solution, it is characterised in that it includes following step
Suddenly：
1) urea, is subjected to azeotropic distillation dewater treatment with absolute ethyl alcohol first, is less than the urea water content after dewater treatment
0.03%, the ethanol water content after distillation is 0.2%, can make other industrial uses；Then by urea and aminopropyl-triethoxy
Silane raw material presses 1：3.68 weight ratio, first aminopropyl triethoxysilane raw material is pumped into the reactor with stirring, and
Urea raw material is put into reactor under stirring nitrogen protective condition；
2) after the completion of, urea raw material feeds intake, reactor is heated up in the case where stirring nitrogen protective condition, reacted 4 hours under normal pressure；
3), synthesis under normal pressure opens water circulation vavuum pump and continues reaction 4 hours under -0.09MPa vacuum after 4 hours；Entirely
Tail gas in course of reaction is absorbed with dilute hydrochloric acid solution, and the aqueous ammonium chloride solution of generation can do agricultural fertilizer use；
4), continue within 4 hours after completion of the reaction, kettle temperature to be dropped into 45 DEG C -50 DEG C under nitrogen protective condition, obtains urea propyl triethoxy
Silane sterling, then be pumped into quantitative methanol, obtain methanol content 0%-80% urea propyl-triethoxysilicane-methanol solution into
Product.
2. a kind of synthesis compound method of urea propyl-triethoxysilicane-methanol solution according to claim 1, its feature
It is, temperature of reaction kettle is 120 DEG C -130 DEG C in step (2).
3. a kind of synthesis compound method of urea propyl-triethoxysilicane-methanol solution according to claim 1, its feature
It is, the vacuum of (3) step water circulation vavuum pump is -0.09MPa.
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| CN201610852101.0A CN107868100A (en) | 2016-09-26 | 2016-09-26 | A kind of synthesis compound method of urea propyl-triethoxysilicane methanol solution |
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| CN201610852101.0A CN107868100A (en) | 2016-09-26 | 2016-09-26 | A kind of synthesis compound method of urea propyl-triethoxysilicane methanol solution |
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| CN107868100A true CN107868100A (en) | 2018-04-03 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109663467A (en) * | 2019-02-25 | 2019-04-23 | 临沂华毅医药股份有限公司 | A kind of aminating reaction object optimization device and method of ortho-aminobenzoic acid |
-
2016
- 2016-09-26 CN CN201610852101.0A patent/CN107868100A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109663467A (en) * | 2019-02-25 | 2019-04-23 | 临沂华毅医药股份有限公司 | A kind of aminating reaction object optimization device and method of ortho-aminobenzoic acid |
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