CN101544382A - Synthesizing method of sodium thiocyanate - Google Patents
Synthesizing method of sodium thiocyanate Download PDFInfo
- Publication number
- CN101544382A CN101544382A CN200910137548A CN200910137548A CN101544382A CN 101544382 A CN101544382 A CN 101544382A CN 200910137548 A CN200910137548 A CN 200910137548A CN 200910137548 A CN200910137548 A CN 200910137548A CN 101544382 A CN101544382 A CN 101544382A
- Authority
- CN
- China
- Prior art keywords
- synthesizing method
- sodium thiocyanate
- sodium
- acid
- sodium cyanide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 title claims abstract description 16
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 13
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 claims abstract description 13
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229940068041 phytic acid Drugs 0.000 claims abstract description 13
- 235000002949 phytic acid Nutrition 0.000 claims abstract description 13
- 239000000467 phytic acid Substances 0.000 claims abstract description 13
- 150000007524 organic acids Chemical class 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 9
- 239000007791 liquid phase Substances 0.000 claims description 8
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 238000003408 phase transfer catalysis Methods 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
- 238000002203 pretreatment Methods 0.000 claims description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- 229960002675 xylitol Drugs 0.000 claims description 2
- 235000010447 xylitol Nutrition 0.000 claims description 2
- 239000000811 xylitol Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 238000007781 pre-processing Methods 0.000 abstract 1
- 230000036632 reaction speed Effects 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 235000017550 sodium carbonate Nutrition 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 239000005864 Sulphur Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 4
- 238000006365 thiocyanation reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- WBBKHUREQLFZGT-UHFFFAOYSA-N N#CC#N.[Na].S(O)(O)(=O)=O Chemical compound N#CC#N.[Na].S(O)(O)(=O)=O WBBKHUREQLFZGT-UHFFFAOYSA-N 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010850 salt effect Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 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 discloses a synthesizing method of sodium thiocyanate. The synthesizing method adopts an organic acid for preprocessing the raw material of sodium cyanide and adopts a two-phase catalyst mixture for executing catalytic reaction to prepare sodium thiocyanate. The invention adopts the phytic acid or polyphosphoric acid as the organic acid for neutralizing the alkali components of NaOH, Na2CO3 contained in the raw material of sodium cyanide for generating the organic salt which is easily eliminated and reducing the alkalinity of sodium cyanide thereby reducing the velocity of hydrolysis. The adoption of two-phase catalyst mixture can reduce the reaction temperature and fastens the reaction speed thereby the product yield can get to 99.7% maximumly.
Description
Technical field
The present invention relates to the synthetic of compound, specifically, the present invention is a kind of synthesizing method of sodium thiocyanate.
Background technology
Sodium Thiocyanate 99 is white rhombic system crystallization or powder, relative density 1.735, fusing point is about 287 ℃, and it is neutral that soluble in water, ethanol, acetone equal solvent, the aqueous solution are, meet molysite and generate sanguine thiocyanation iron, meet ferrous salt and do not react, generate xanchromatic sulfuric acid cyanogen sodium, generate navy blue thiocyanation cobalt with the cobalt salt effect with the vitriol oil, the copper rhodanide that generates white thiocyanation silver or black with silver salt or mantoquita effect precipitates, easy deliquescence in air.This product can be widely used as acrylonitrile fiber axis solvent, chemical analysis reagent, and the colour cinefilm irrigation, certain plants defoliating agent and airport roadway weedkiller also are used for pharmacy, printing and dyeing, rubberized, black nickel plating and manufacturing artificial mustard oil etc.
Existing traditional Sodium Thiocyanate 99 production is synthetic to be raw material with sodium cyanide and sulphur, process using liquid liquid phase transfer catalyst carries out, its synthesis yield is generally between 96%～97%, there is following shortcoming in its technological process: 1, the alkalescence of raw material liq sodium cyanide is high, when initial reaction, sodium cyanide and sulphur all are easier to take place hydrolysis reaction, produce by product; 2, adopt the common process condition, sulphur is under the melting state, carry out the thiocyanation reaction with quaternary ammonium salt two phase catalysts, temperature of reaction reaches about 120 ℃, the hydrolysis reaction of sodium cyanide and sulphur will further be quickened, by product continues to increase, thereby has influenced the quality of product and the difficulty that processing wastewater is handled.
Summary of the invention
In order to overcome above-mentioned technical problem, the invention provides a kind of synthesizing method of sodium thiocyanate.
In order to realize above-mentioned goal of the invention, the present invention by the following technical solutions:
A kind of synthesizing method of sodium thiocyanate adopts organic acid that the raw material sodium cyanide is carried out pre-treatment, and adopts the two-phase mixed catalyst to carry out catalyzed reaction to make.
Described two-phase mixed catalyst is a kind of or its combination in quaternary ammonium salt, hexadecanol, Xylitol or the wooden amylalcohol.
Preferably, described catalyzer is the composition that Tetrabutyl amonium bromide and wooden amylalcohol were formed by weight 1: 1.And, further, solid-liquid phase transfer catalysis agent or liquid-liquid phase transfer catalyst that catalyzer is made up of Tetrabutyl amonium bromide and wooden amylalcohol.
Above-mentioned organic acid adopts polymer acid, normally phytic acid or polyphosphoric acid.The organic acid that is adopted is phytic acid preferably.
Phytic acid (Phytic acid) formal name used at school phytic acid, molecular formula: C
6H
18O
24P
6, molecular weight: 660.08.Phytic acid extensively is present in the plant seed, and present main application is a nutritious prod.The notable attribute of phytic acid is with metal ion extremely strong network and effect and oxidation-resistance to be arranged.
The present invention has following advantage:
The present invention adopts phytic acid or polyphosphoric acid as organic acid, to alkali components of NaOH, the Na that contains in the raw material sodium cyanide
2CO
3Neutralizing generates the organic salt of removing easily, and reduces the basicity of sodium cyanide, thereby reduces the degree of its hydrolysis; Adopt solid-liquid or liquid-liquid mixed catalyst that temperature of reaction is descended, side reaction reduces, and speed of response is accelerated, thereby makes the yield of product can reach 99.7%.
Embodiment
Embodiment 1
During 30% the sodium cyanide liquid of 1mol carried out in advance with phytic acid and reserve use, again with in the disposable input synthesis reactor of the sulphur of 1mol, add an amount of water, be warming up to 100 ℃, add 3 ‰ mixed catalyst (the solid-liquid phase transfer catalysis agent that Tetrabutyl amonium bromide and wooden amylalcohol are formed by weight 1:1), slowly the ready-formed sodium cyanide is added in the synthesis reactor constant temperature 30min in 20min, reaction finishes, sodium sulfocynanate yield 99.6%.
Embodiment 2
During 30% the sodium cyanide liquid of 1mol carried out in advance with phytic acid and reserve use, again with in the disposable input synthesis reactor of the sulphur of 1mol, add an amount of water, be warming up to 70 ℃, add 3 ‰ mixed catalyst (the liquid-liquid phase transfer catalyst that Tetrabutyl amonium bromide and wooden amylalcohol are formed by weight 1:1), slowly in 20min, add the ready-formed sodium cyanide in the synthesis reactor, charge temperature is controlled at below 105 ℃, add material back temperature and rise to 118 ℃ of insulation 30min, reaction finishes, sodium sulfocynanate yield 99.7%.
Embodiment 3
During 30% the sodium cyanide liquid of 1mol carried out in advance with polyphosphoric acid and reserve use, again with in the disposable input synthesis reactor of the sulphur of 1mol, add an amount of water, be warming up to 70 ℃, add 3 ‰ mixed catalyst (the liquid-liquid phase transfer catalyst that Tetrabutyl amonium bromide and wooden amylalcohol are formed by weight 1:1), slowly in 20min, add the ready-formed sodium cyanide in the synthesis reactor, charge temperature is controlled at below 105 ℃, add material back temperature and rise to 118 ℃ of insulation 30min, reaction finishes, sodium sulfocynanate yield 99.6%.
More than synthesizing method of sodium thiocyanate provided by the present invention is described in detail, used specific case herein principle of the present invention and embodiment are set forth, the explanation of above embodiment just is used for helping to understand method of the present invention and core concept thereof; Simultaneously, for one of ordinary skill in the art, according to thought of the present invention, the part that all can change in specific embodiments and applications, in sum, this description should not be construed as limitation of the present invention.
Claims (6)
1. synthesizing method of sodium thiocyanate is characterized in that: adopt organic acid that the raw material sodium cyanide is carried out pre-treatment, and adopt the two-phase mixed catalyst to carry out catalyzed reaction to make.
2. synthesizing method of sodium thiocyanate according to claim 1 is characterized in that: described catalyzer is a kind of or its combination in quaternary ammonium salt, hexadecanol, Xylitol or the wooden amylalcohol.
3. synthesizing method of sodium thiocyanate according to claim 1 is characterized in that: described catalyzer is the composition that Tetrabutyl amonium bromide and wooden amylalcohol are formed by weight 1:1.
4. according to the synthesizing method of sodium thiocyanate described in the claim 3, it is characterized in that: solid-liquid phase transfer catalysis agent or liquid-liquid phase transfer catalyst that described catalyzer is made up of Tetrabutyl amonium bromide and wooden amylalcohol.
5. synthesizing method of sodium thiocyanate according to claim 1 is characterized in that: described organic acid is phytic acid or polyphosphoric acid.
6. phytic acid is in the purposes of preparation in the Sodium Thiocyanate 99.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910137548XA CN101544382B (en) | 2009-05-11 | 2009-05-11 | Synthesizing method of sodium thiocyanate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910137548XA CN101544382B (en) | 2009-05-11 | 2009-05-11 | Synthesizing method of sodium thiocyanate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101544382A true CN101544382A (en) | 2009-09-30 |
| CN101544382B CN101544382B (en) | 2011-01-05 |
Family
ID=41191794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200910137548XA Active CN101544382B (en) | 2009-05-11 | 2009-05-11 | Synthesizing method of sodium thiocyanate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101544382B (en) |
-
2009
- 2009-05-11 CN CN200910137548XA patent/CN101544382B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101544382B (en) | 2011-01-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102911122B (en) | Metronidazole preparation method | |
| CN103739524B (en) | A kind of preparation method of H acid monosodium salt | |
| CN102321028B (en) | Method for synthesizing 2-methyl-5-nitroimidazole-1-ethanol | |
| CN109678727A (en) | A kind of method of microchannel nitration reaction synthesis 2- ethyl -5- nitroaniline | |
| CN103232497A (en) | Alkyl glucoside preparation method | |
| CN105085411A (en) | Preparation method of 6-hydroxy-2,3,5-triamidopyrimidine sulfate | |
| CN102249994A (en) | Preparation method of nicotinic acid | |
| CN102875435B (en) | Organic thiosulfuric acid derivative preparation method | |
| CN102924380A (en) | Preparation method of imidocarb | |
| CN1911907A (en) | Preparation method of dyestuff intermediate H acid | |
| CN109912471B (en) | A kind of method for continuously and rapidly hydrolyzing 2-hydroxy-4-methylthiobutyronitrile to synthesize methionine hydroxyl analog | |
| CN102108063A (en) | Method for preparing maleic hydrazide | |
| CN101544382B (en) | Synthesizing method of sodium thiocyanate | |
| CN102070680B (en) | Preparation method of alkyl polyglucoside sulfate | |
| CN103072950A (en) | Method for extracting high-purity sodium thiocyanate and sodium thiosulfate in gas desulfurization waste salt | |
| CN103466707A (en) | Production method of chromic chloride hexahydrate | |
| CN103145618B (en) | Method for cogeneration of caprolactam and ammonium sulfate | |
| CN102643237A (en) | Method for preparing 1H-imidazole-4-formic acid | |
| CN105268450B (en) | The catalyst that a kind of hydrogenation catalyst synthesizes the method for the disulfonate sodium of 8 amino, 1 naphthols 3,6 and its used | |
| CN108640892A (en) | A kind of synthetic method of 5 hydroxymethyl furfural | |
| CN102558060A (en) | Process for preparing imidazolidine | |
| CN102502570B (en) | Production method of medical sodium metavanadate | |
| CN104689810A (en) | Solid acid catalyst and application of solid acid catalyst in synthesis of reproducible diesel oil or aviation kerosene | |
| CN102432543A (en) | Synthesis method of 4-iodo-1H-imidazole | |
| CN105622518B (en) | A kind of preparation method of 1H- imidazoles -4- formic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: BINHAI MINGHONG FINE CHEMICAL CO., LTD. Free format text: FORMER OWNER: YIXING LIAOYUAN CHEMICAL CO., LTD. Effective date: 20131217 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 214261 WUXI, JIANGSU PROVINCE TO: 224500 YANCHENG, JIANGSU PROVINCE |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20131217 Address after: 224500. Binhai Industrial Park, Binhai Economic Development Zone, Yancheng City, Jiangsu Province Patentee after: Binhai County Minghong Fine Chemical Co., Ltd. Address before: 214261 Jiangsu province Yixing Zhoutie town village of jellyfish Patentee before: Yixing Liao Yuan Chemical Co., Ltd. |
|
| ASS | Succession or assignment of patent right |
Owner name: YIXING LIAOYUAN CHEMICAL CO., LTD. Free format text: FORMER OWNER: BINHAI MINGHONG FINE CHEMICAL CO., LTD. Effective date: 20140603 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 224500 YANCHENG, JIANGSU PROVINCE TO: 224500 WUXI, JIANGSU PROVINCE |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20140603 Address after: 224500 Jiangsu city of Wuxi province Yixing Zhoutie town village of jellyfish Patentee after: Yixing Liao Yuan Chemical Co., Ltd. Address before: 224500. Binhai Industrial Park, Binhai Economic Development Zone, Yancheng City, Jiangsu Province Patentee before: Binhai County Minghong Fine Chemical Co., Ltd. |
|
| C56 | Change in the name or address of the patentee |
Owner name: JIANGSU LIAOYUAN ENVIRONMENTAL TECHNOLOGY CO., LTD Free format text: FORMER NAME: YIXING LIAOYUAN CHEMICAL CO., LTD. |
|
| CP01 | Change in the name or title of a patent holder |
Address after: 224500 Jiangsu city of Wuxi province Yixing Zhoutie town village of jellyfish Patentee after: Jiangsu Liaoyuan Environmental Technology Co., Ltd. Address before: 224500 Jiangsu city of Wuxi province Yixing Zhoutie town village of jellyfish Patentee before: Yixing Liao Yuan Chemical Co., Ltd. |