CN102557894B - Synthesis process of 1, 2, 3-trimethoxy benzene - Google Patents
Synthesis process of 1, 2, 3-trimethoxy benzene Download PDFInfo
- Publication number
- CN102557894B CN102557894B CN201210009907.5A CN201210009907A CN102557894B CN 102557894 B CN102557894 B CN 102557894B CN 201210009907 A CN201210009907 A CN 201210009907A CN 102557894 B CN102557894 B CN 102557894B
- Authority
- CN
- China
- Prior art keywords
- controlled
- temperature
- reaction
- described step
- finished
- 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.)
- Active
Links
- 0 *C1C(*)*=CC1 Chemical compound *C1C(*)*=CC1 0.000 description 3
Abstract
The invention relates to a synthesis process of 1, 2, 3-trimethoxy benzene. The synthesis process comprises the following steps of: (1) putting guaiacol into a reaction kettle and then dripping acetylchloride; (2) after the reaction in the step (1) is finished, adding o-xylene and aluminium chloride into the reaction kettle; (3) after the reaction in the step (2) is finished, dripping process water for hydrolysis; (4) after the reaction in the step (3) is finished, standing for layering, desolventizing an organic layer and obtaining an intermediate, i.e., 2-hydroxyl-methoxyacetophenone; (5) putting the 2-hydroxyl-methoxyacetophenone, alkali and the process water obtained in the step (4) into the reaction kettle, stirring uniformly, then dripping hydrogen peroxide and obtaining 1, 2-dyhydroxyl-3-metoxybenzene; (6) after the reaction in the step (5) is finished, dripping dimethyl sulfate and alkali liquor simultaneously into the reaction kettle; (7) after the reaction in the step (6) is finished, standing for layering, and obtaining a crude product; and (8) putting the crude product into a distillation kettle for distillation and obtaining a product. The synthesis process has the advantages of mild condition, simple operation, low synthesis cost, good product quality and suitability for industrial production.
Description
Technical field
The present invention relates to a kind of synthetic and preparation method of organic compound, particularly one 1,2, the synthesis technique of 3-trimethoxy-benzene.
Background technology
1,2,3-trimethoxy-benzene is widely used in organic synthesis and pharmaceutical industry field, and it is the important intermediate of producing multi-medicament.Producing in the past this product all utilizes traditional Chinese medicine Turkey-galls and import tower to draw powder to produce.Patent application 200510018690.4 discloses a kind of employing pyrogallol and has prepared 1,2, the method of 3-trimethoxy-benzene, patent application 200610030549.0 discloses a kind of employing acer ginnala leaf and has produced 1,2, the method of 3-trimethoxy-benzene, patent application 200810210575.0 discloses a kind of employing ortho vanillin through Dakin oxidation methylated production method again.Current also do not have industrial utilization methyl catechol (2-methoxyl group phenol) through acidylate, Fries reset, Dakin(reaches gold) oxidation methylated production method again.
Summary of the invention
The object of the present invention is to provide that a kind of reaction conditions gentleness, simple to operate, synthetic cost are low, good product quality 1,2, the synthesis technique of 3-trimethoxy-benzene.
For achieving the above object, the technical solution adopted in the present invention is:
One 1,2, the synthesis technique of 3-trimethoxy-benzene, comprises the steps:
1. methyl catechol (2-methoxyl group phenol) is dropped in reactor, then drip Acetyl Chloride 98Min., obtain adjacent acetoxyl group methyl-phenoxide;
2., after 1. step is reacted and finished, in reactor, add o-Xylol, aluminum chloride (AlCl3);
3., after 2. step is reacted and finished, drip process water hydrolysis;
4. after 3. step is reacted and is finished, stratification, organic layer precipitation obtains intermediate 2-hydroxy 3-methoxybenzene ethyl ketone;
5. the 2-hydroxy 3-methoxybenzene ethyl ketone, alkali, the process water that 4. step are obtained drop in reactor, after stirring, then drip hydrogen peroxide, obtain 1,2-dihydroxyl-3-anisole;
6., after 5. step is reacted and finished, in reactor, drip methyl-sulfate and alkali lye simultaneously;
7., after 6. step is reacted and finished, stratification, obtains crude product;
8. crude product is dropped in still kettle and distilled, obtain product.
As the further setting of such scheme, described step 1. in mass ratio between methyl catechol and Acetyl Chloride 98Min. be 1:1.0～1.3; Described step 2., step 3. in mass ratio between adjacent acetoxyl group methyl-phenoxide, o-Xylol, aluminum chloride, process water be 1:1.5～3.0:0.3～0.5:1.0～2.0; The described step 5. mass ratio between middle 2-hydroxy 3-methoxybenzene ethyl ketone, hydrogen peroxide, alkali, process water is 1:3～3.5:0.2～0.5:1.0～1.5; Described step 6. in 1, the mass ratio between 2-dihydroxyl-3-anisole, methyl-sulfate, alkali lye is 1:2～2.5:3～3.5.
Described step is 1. adding in Acetyl Chloride 98Min. process, and reactor temperature is controlled at-5～20 ℃; Drip and finish, holding temperature is controlled at 0～30 ℃, soaking time 2～4 hours.
Described step 2. middle reactor temperature is controlled at 100～150 ℃, insulation return time 2～5 hours.
Described step 3. in when hydrolysis reactor temperature be controlled at 30～50 ℃, hydrolysis time 1～3 hour, step 4. in when stratification, temperature is controlled at 30～50 ℃, time of repose 1～2 hour, precipitation temperature is controlled at 50～90 ℃, be greater than-0.095Mpa of vacuum tightness.
Described step 5. middle reactor temperature is controlled at 10～20 ℃, and system pH is controlled at 9～11.
When described step adds methyl-sulfate, alkali lye in 6. simultaneously, reactor temperature is controlled at 30～45 ℃, and system pH is controlled at 9～10, reaction soaking time 1～2 hour, 70～80 ℃ of heating and heat preservation temperature, 1～2 hour heating and heat preservation time.
Described step 7. middle stratification temperature is controlled at 30～45 ℃, time of repose 1～2 hour.
Described step 8. in the interior temperature control of still kettle at 110～140 ℃, be greater than-0.095Mpa of vacuum tightness.
Described step 2. in determining step 1. reaction end, step 3. in determining step 2. reaction end, step 4. in determining step 3. reaction end, step 6. in determining step 5. reaction end, step 7. in determining step 6. reaction end monitor by tlc (TLC).
One 1,2 of the present invention, the synthesis technique of 3-trimethoxy-benzene, its step is 1. in reaction process, by refrigerated water control temperature of reaction, in case overtemperature will be carried out the absorption of HCl acid mist simultaneously;
Step 2. in determining step 1. reaction end is by tlc (TLC) monitoring, second eyeball/normal hexane that developping agent is 1:1, until the completely dissolve of raw material point is considered as reacting completely.Reaction must have in reflux to be carried out;
Step 3. in determining step 2. reaction end is by tlc (TLC) monitoring, acetonitrile/ethyl acetate that developping agent is 2:3, until the completely dissolve of raw material point is considered as reacting completely.While adding process water, forbid temperature in the kettle overtemperature;
Step 4. in determining step 3. reaction end is by tlc (TLC) monitoring, acetonitrile/ethyl acetate that developping agent is 2:3, until the completely dissolve of raw material point is considered as reacting completely;
The hydrogen peroxide concentration of step described in is 5. 10～35%, preferably 25%.Described alkali is sodium hydroxide or potassium hydroxide, preferably potassium hydroxide, and concentration is 20～60%, preferably 25%;
Step 6. in determining step 5. reaction end by tlc (TLC) monitoring, ethyl acetate/normal hexane that developping agent is 2:3.Until the completely dissolve of raw material point is considered as reacting completely.Described alkali lye is sodium hydroxide or potassium hydroxide, preferably sodium hydroxide, concentration preferably 30%;
Step 7. in determining step 6. reaction end is by tlc (TLC) monitoring, ethyl acetate/normal hexane that developping agent is 2:3, until the completely dissolve of raw material point is considered as reacting completely;
Step 8. in, when distillation, it is cooling that condenser must lead to the hot water of 40～45 ℃, in case blocking pipe.Distillation thermal source can adopt steam or thermal oil.
One 1,2 of the present invention, the synthesis technique of 3-trimethoxy-benzene, involved correlated response formula comprises as follows:
One 1,2 of the present invention, the synthesis technique of 3-trimethoxy-benzene, has that raw material sources are extensive, reaction conditions is gentle, simple to operate, synthetic cost is low, good product quality, is applicable to suitability for industrialized production.
Embodiment
Below in conjunction with embodiment, the present invention is further described.Following embodiment is illustrative, is not determinate, can not limit protection scope of the present invention with following embodiment.
Embodiment 1
In actual production, 150 kilograms of methyl catechol that calculate are dropped in reactor, 100 kilograms of Acetyl Chloride 98Min.s drop into header tank, stir the lower Acetyl Chloride 98Min. that slowly drips, and along with dropping is carried out, note the absorption of tail gas HCl.Meanwhile, in dropping Acetyl Chloride 98Min. process, reactor temperature is controlled at-5 ℃; Drip and finish, holding temperature is controlled at 0 ℃, soaking time 4 hours, and to reacting completely, reaction end is by tlc (TLC) judgement, until the completely dissolve of raw material point is considered as reacting completely.After reacting completely, drop into 400 kilograms of o-Xylols, 160 kilograms, aluminum chloride, the rearrangement reaction that refluxes, insulation return time 5 hours at 100 ℃.Reaction end is by tlc (TLC) judgement, until the completely dissolve of raw material point is considered as reacting completely.After having reacted, drip 250 kilograms of process water hydrolysis, stir, reaction end is by tlc (TLC) judgement, until the completely dissolve of raw material point is considered as reacting completely.While wherein hydrolysis, reactor temperature is controlled at 30 ℃, hydrolysis time 3 hours.After reaction finishes, temperature is controlled to 30 ℃ and carries out stratification, time of repose 2 hours.The organic layer separating carries out precipitation under the condition of temperature 50 C, vacuum tightness-0.095Mpa, obtains intermediate 2-hydroxy 3-methoxybenzene ethyl ketone.190 kilograms of intermediate 2-hydroxy 3-methoxybenzene ethyl ketones are put in reactor, added 200 kilograms of process waters, 52 kilograms of potassium hydroxide simultaneously, after stirring, drip 600 kilograms, 25% hydrogen peroxide.Along with dropping is carried out, exothermic heat of reaction, by 10 ℃ of cooling water control temperature of reaction, the pH of simultaneous reactions system keeps 9～10.Dropwise, insulation is to reacting completely.After having reacted, drip 450 kilograms of methyl-sulfates and 610 kilogram of 30% sodium hydroxide simultaneously, control rate of addition and make system pH keep 9～10, and keep reactor temperature to be controlled at 30 ℃.Dropwise, at this temperature, be incubated 2 hours, then be warming up to 70 ℃ of insulations 2 hours.Reaction finishes, and stratification under the temperature condition of 30 ℃ leaves standstill 2 hours and obtains 182 kilograms of crude products.Crude product is dropped in still kettle, under the condition of 120 ℃ of interior temperature, vacuum tightness-0.095Mpa, obtain 154 kilograms of products (finished product), product appearance white is to faint yellow solid, and content is greater than 99%, and yield 76%(calculates with methyl catechol).
Embodiment 2
In actual production, 150 kilograms of methyl catechol that calculate are dropped in reactor, 96 kilograms of Acetyl Chloride 98Min.s drop into header tank, stir the lower Acetyl Chloride 98Min. that slowly drips, and along with dropping is carried out, note the absorption of tail gas HCl.Meanwhile, in dropping Acetyl Chloride 98Min. process, reactor temperature is controlled at 20 ℃; Drip and finish, holding temperature is controlled at 30 ℃, soaking time 2 hours, and to reacting completely, reaction end is by tlc (TLC) judgement, until the completely dissolve of raw material point is considered as reacting completely.After reacting completely, drop into 380 kilograms of o-Xylols, 155 kilograms, aluminum chloride, the rearrangement reaction that refluxes, insulation return time 2 hours at 150 ℃.Reaction end is by tlc (TLC) judgement, until the completely dissolve of raw material point is considered as reacting completely.After having reacted, drip 220 kilograms of process water hydrolysis, stir, reaction end is by tlc (TLC) judgement, until the completely dissolve of raw material point is considered as reacting completely.While wherein hydrolysis, reactor temperature is controlled at 50 ℃, hydrolysis time 1 hour.After reaction finishes, temperature is controlled to 50 ℃ and carries out stratification, time of repose 1 hour.The organic layer separating carries out precipitation under the condition of 90 ℃ of temperature, vacuum tightness-0.095Mpa, obtains intermediate 2-hydroxy 3-methoxybenzene ethyl ketone.185 kilograms of intermediate 2-hydroxy 3-methoxybenzene ethyl ketones are put in reactor, added 150 kilograms of process waters, 50 kilograms of potassium hydroxide simultaneously, after stirring, drip 550 kilograms, 25% hydrogen peroxide.Along with dropping is carried out, exothermic heat of reaction, by 20 ℃ of cooling water control temperature of reaction, the pH of simultaneous reactions system keeps 9～10.Dropwise, insulation is to reacting completely.After having reacted, drip 430 kilograms of methyl-sulfates and 580 kilogram of 30% sodium hydroxide simultaneously, control rate of addition and make system pH keep 9～10, and keep reactor temperature to be controlled at 45 ℃.Dropwise, at this temperature, be incubated 1 hour, then be warming up to 80 ℃ of insulations 1 hour.Reaction finishes, and stratification under the temperature condition of 45 ℃ leaves standstill 1 hour and obtains 170 kilograms of crude products.Crude product is dropped in still kettle, under the condition of 140 ℃ of interior temperature, vacuum tightness-0.098Mpa, obtain 146 kilograms of products (finished product), product appearance white is to faint yellow solid, and content is greater than 99%, and yield 72%(calculates with methyl catechol).
Embodiment 3
In actual production, 150 kilograms of methyl catechol that calculate are dropped in reactor, 105 kg Acetyl Chloride 98Min. drops into header tank, stirs the lower Acetyl Chloride 98Min. that slowly drips, and along with dropping is carried out, notes the absorption of tail gas HCl.Meanwhile, in dropping Acetyl Chloride 98Min. process, reactor temperature is controlled at 10 ℃; Drip and finish, holding temperature is controlled at 15 ℃, soaking time 3 hours, and to reacting completely, reaction end is by tlc (TLC) judgement, until the completely dissolve of raw material point is considered as reacting completely.After reacting completely, drop into 450 kilograms of o-Xylols, 180 kilograms, aluminum chloride, the rearrangement reaction that refluxes, insulation return time 3 hours at 120 ℃.Reaction end is by tlc (TLC) judgement, until the completely dissolve of raw material point is considered as reacting completely.After having reacted, drip 240 kilograms of process water hydrolysis, stir, reaction end is by tlc (TLC) judgement, until the completely dissolve of raw material point is considered as reacting completely.While wherein hydrolysis, reactor temperature is controlled at 40 ℃, hydrolysis time 2 hours.After reaction finishes, temperature is controlled to 40 ℃ and carries out stratification, time of repose 1.5 hours.The organic layer separating carries out precipitation under the condition of temperature 70 C, vacuum tightness-0.098Mpa, obtains intermediate 2-hydroxy 3-methoxybenzene ethyl ketone.180 kilograms of intermediate 2-hydroxy 3-methoxybenzene ethyl ketones are put in reactor, added 210 kilograms of process waters, 60 kilograms of potassium hydroxide simultaneously, after stirring, drip 750 kilograms, 25% hydrogen peroxide.Along with dropping is carried out, exothermic heat of reaction, by 16 ℃ of cooling water control temperature of reaction, the pH of simultaneous reactions system keeps 9～10.Dropwise, insulation is to reacting completely.After having reacted, drip 480 kilograms of methyl-sulfates and 650 kilogram of 30% sodium hydroxide simultaneously, control rate of addition and make system pH keep 9～10, and keep reactor temperature to be controlled at 40 ℃.Dropwise, at this temperature, be incubated 1.5 hours, then be warming up to 75 ℃ of insulations 1.5 hours.Reaction finishes, and stratification under the temperature condition of 40 ℃ leaves standstill 1.5 hours and obtains 160 kilograms of crude products.Crude product is dropped in still kettle, under the condition of 110 ℃ of interior temperature, vacuum tightness-0.098Mpa, obtain 142 kilograms of products (finished product), product appearance white is to faint yellow solid, and content is greater than 99%, and yield 70%(calculates with methyl catechol).
Above-described embodiment is only for the inventive concept of the present invention of explaining, but not restriction to rights protection of the present invention, allly utilizes this design to carry out the change of unsubstantiality to the present invention, all should fall into protection scope of the present invention.
Claims (2)
1. one kind 1,2, the synthesis technique of 3-trimethoxy-benzene, is characterized in that comprising the steps:
1. methyl catechol is dropped in reactor, then drip Acetyl Chloride 98Min., obtain adjacent acetoxyl group methyl-phenoxide;
2., after 1. step is reacted and finished, in reactor, add o-Xylol, aluminum chloride;
3., after 2. step is reacted and finished, drip process water hydrolysis;
4. after 3. step is reacted and is finished, stratification, organic layer precipitation obtains intermediate 2-hydroxy 3-methoxybenzene ethyl ketone;
5. the 2-hydroxy 3-methoxybenzene ethyl ketone, alkali, the process water that 4. step are obtained drop in reactor, after stirring, then drip hydrogen peroxide, obtain 1,2-dihydroxyl-3-anisole;
6., after 5. step is reacted and finished, in reactor, drip methyl-sulfate and alkali lye simultaneously;
7., after 6. step is reacted and finished, stratification, obtains crude product;
8. crude product is dropped in still kettle and distilled, obtain product;
Described step 1. in mass ratio between methyl catechol and Acetyl Chloride 98Min. be 1:1.0～1.3; Described step 2., step 3. in mass ratio between adjacent acetoxyl group methyl-phenoxide, o-Xylol, aluminum chloride, process water be 1:1.5～3.0:0.3～0.5:1.0～2.0; The described step 5. mass ratio between middle 2-hydroxy 3-methoxybenzene ethyl ketone, hydrogen peroxide, alkali, process water is 1:3～3.5:0.2～0.5:1.0～1.5; Described step 6. in 1, the mass ratio between 2-dihydroxyl-3-anisole, methyl-sulfate, alkali lye is 1:2～2.5:3～3.5;
Described step is 1. in dropping Acetyl Chloride 98Min. process, and reactor temperature is controlled at-5～20 ℃; Drip and finish, holding temperature is controlled at 0～30 ℃, soaking time 2～4 hours;
Described step 2. middle reactor temperature is controlled at 100～150 ℃, insulation return time 2～5 hours;
Described step 3. in when hydrolysis reactor temperature be controlled at 30～50 ℃, hydrolysis time 1～3 hour, step 4. in when stratification, temperature is controlled at 30～50 ℃, time of repose 1～2 hour, precipitation temperature is controlled at 50～90 ℃, be greater than-0.095Mpa of vacuum tightness;
Described step 5. middle reactor temperature is controlled at 10～20 ℃, and system pH is controlled at 9～11;
When described step drips methyl-sulfate, alkali lye in 6. simultaneously, reactor temperature is controlled at 30～45 ℃, and system pH is controlled at 9～10, reaction soaking time 1～2 hour, 70～80 ℃ of heating and heat preservation temperature, 1～2 hour heating and heat preservation time;
Described step 7. middle stratification temperature is controlled at 30～45 ℃, time of repose 1～2 hour;
Described step 8. in the interior temperature control of still kettle at 110～140 ℃, be greater than-0.095Mpa of vacuum tightness.
2. as claimed in claim 1 a kind of 1,2, the synthesis technique of 3-trimethoxy-benzene, is characterized in that: described step 2. in determining step 1. reaction end, step 3. in determining step 2. reaction end, step 4. in determining step 3. reaction end, step 6. in determining step 5. reaction end, step 7. in determining step 6. reaction end monitor by tlc.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210009907.5A CN102557894B (en) | 2012-01-13 | 2012-01-13 | Synthesis process of 1, 2, 3-trimethoxy benzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210009907.5A CN102557894B (en) | 2012-01-13 | 2012-01-13 | Synthesis process of 1, 2, 3-trimethoxy benzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102557894A CN102557894A (en) | 2012-07-11 |
| CN102557894B true CN102557894B (en) | 2014-05-14 |
Family
ID=46404675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210009907.5A Active CN102557894B (en) | 2012-01-13 | 2012-01-13 | Synthesis process of 1, 2, 3-trimethoxy benzene |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102557894B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1340494A (en) * | 2000-08-31 | 2002-03-20 | 科学工业研究院 | Improved method for preparing 1-propyl-2,4,5-trimethoxy benzene |
| US20060035982A1 (en) * | 2004-08-06 | 2006-02-16 | Takasago International Corporation | Method for promoting blood stream |
| CN101665417A (en) * | 2008-09-02 | 2010-03-10 | 中化宁波（集团）有限公司 | One-pot process for synthesizing 1,2,3-trimethoxy-benzene by using o-vanillin |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05148175A (en) * | 1991-11-07 | 1993-06-15 | Eisai Co Ltd | Production of p-dimethoxybenzene derivative |
-
2012
- 2012-01-13 CN CN201210009907.5A patent/CN102557894B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1340494A (en) * | 2000-08-31 | 2002-03-20 | 科学工业研究院 | Improved method for preparing 1-propyl-2,4,5-trimethoxy benzene |
| US20060035982A1 (en) * | 2004-08-06 | 2006-02-16 | Takasago International Corporation | Method for promoting blood stream |
| CN101665417A (en) * | 2008-09-02 | 2010-03-10 | 中化宁波（集团）有限公司 | One-pot process for synthesizing 1,2,3-trimethoxy-benzene by using o-vanillin |
Non-Patent Citations (1)
| Title |
|---|
| JP特开平5-148175A 1993.06.15 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102557894A (en) | 2012-07-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102295541B (en) | Preparation method of 3,3-dimethyl butyraldehyde | |
| CN105254603A (en) | Synthetic technology of furan ammonium salt | |
| CN103159659A (en) | Preparation method of muscarinic receptor antagonist glycopyrronium bromide | |
| CN102557894B (en) | Synthesis process of 1, 2, 3-trimethoxy benzene | |
| CN103073449A (en) | Method for synthesizing N, O-dimethylhydroxylamine hydrochloride | |
| CN103755533B (en) | Method for synthesizing anethole by taking estragole oil as raw material | |
| CN103058984B (en) | Synthesis method of watermelon ketone | |
| CN104910032A (en) | Preparation method of anilino-acetate | |
| CN109503469B (en) | Preparation method of 2-acetylpyridine | |
| CN104693025B (en) | A kind of method preparing 1,3-propanedicarboxylic acid list L-menthyl ester | |
| CN103058868B (en) | Menthyl lactate preparation method | |
| CN103508890A (en) | Method for preparing 3-(2-oxocyclopentyl)-propionic acid and 3-(2-oxocyclopentyl)-propionic ester | |
| CN113582821B (en) | Preparation method of 8-methyldecanal | |
| CN104447369A (en) | Method of producing high-purity disodium tetracetate dehydrate by membrane reactor | |
| CN110452109A (en) | A kind of method that phenol ether goes aromatization to prepare loop coil hexadiene ketone compounds | |
| CN101550118B (en) | Synthetic process for vitamin C sodium salts | |
| CN102675036A (en) | Method for preparing 7-bromine-1-heptylene | |
| CN102304014B (en) | Method for preparing epoxiconazole intermediate | |
| CN102341361A (en) | Chemical process for the production of haloalkenone ethers | |
| CN104402927B (en) | A kind of take 4 chloro pyridine as the method for raw material one pot process Chlorpyrifos 94 and the composite catalyst of use | |
| CN101665417B (en) | One-pot process for synthesizing 1,2,3-trimethoxy-benzene by using o-vanillin | |
| CN102875344A (en) | Method for preparing 2, 3, 4-trimethoxybenzaldehyde | |
| CN104151161B (en) | A kind of 2-(2-allyl group) preparation method of amylene-4-acid methyl esters | |
| CN101898957A (en) | Method for synthesizing 3, 4-dihydroxyl mandelic acid by glyoxylic acid method | |
| CN109836322B (en) | Preparation method of royal jelly 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 | ||
| C53 | Correction of patent for invention or patent application | ||
| CB02 | Change of applicant information |
Address after: 312073 North Branch of Binhai Industrial Area, Shaoxing County, Zhejiang, Shaoxing Applicant after: Zhejiang Longhua Fine Chemical Co.,Ltd. Address before: 312073 North Branch of Binhai Industrial Area, Zhejiang, Shaoxing Applicant before: Zhejiang Longhua Fine Chemical Co.,Ltd. |
|
| ASS | Succession or assignment of patent right |
Owner name: ZHEJIANG UALLOY MATERIAL TECHNOLOGY CO., LTD. Free format text: FORMER OWNER: ZHEJIANG LONGHUA FINE CHEMICAL CO., LTD. Effective date: 20130314 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20130314 Address after: 312073 North Branch of Binhai Industrial Area, Shaoxing County, Zhejiang, Shaoxing Applicant after: Zhejiang Ualloy Material Technology Co., Ltd. Address before: 312073 North Branch of Binhai Industrial Area, Shaoxing County, Zhejiang, Shaoxing Applicant before: Zhejiang Longhua Fine Chemical Co.,Ltd. |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |