CN101928220A - Preparation method of 1-hydroxyl-2-naphthoate - Google Patents
Preparation method of 1-hydroxyl-2-naphthoate Download PDFInfo
- Publication number
- CN101928220A CN101928220A CN2009102632378A CN200910263237A CN101928220A CN 101928220 A CN101928220 A CN 101928220A CN 2009102632378 A CN2009102632378 A CN 2009102632378A CN 200910263237 A CN200910263237 A CN 200910263237A CN 101928220 A CN101928220 A CN 101928220A
- Authority
- CN
- China
- Prior art keywords
- hydroxyl
- naphthoate
- naphthoic acid
- preparation
- drying
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of 1-hydroxyl-2-naphthoate, comprising the following steps of: carrying out reaction to 1-hydroxyl-2-naphthoic acid as an initial raw material and excessive triphenyl phosphate to form transparent feed liquid, terminating the reaction, cooling and crystallizing to obtain a crude product; decolorizing the crude product by using a decolorizer, and then carrying out recrystallization, centrifugal separation and drying to the decolorized crude product to obtain the 1-hydroxyl-2-naphthoate product. The preparation method has the advantages of simple process and easy industrialization and can improve the yield of the product to above 90% and the purity to above 99%.
Description
Technical field
The present invention relates to a kind of preparation method of compound, is the preparation method of a kind of 1-hydroxyl-2-naphthoate specifically.
Background technology
1-hydroxyl-2-naphthoate, have another name called 1-hydroxyl-2-naphthoic acid phenyl ester, be light yellow crystalline powder, it can be used as pigment, dyestuff or sensitive materials intermediate, but the route complexity of existing synthetic 1-hydroxyl-2-naphthoate, be unfavorable for suitability for industrialized production, and the high energy of product yield reaches 50%.
Summary of the invention
Goal of the invention: the objective of the invention is in order to overcome the deficiencies in the prior art, provide that a kind of technology is simple, easily industrialization, can improve the preparation method of the 1-hydroxyl-2-naphthoate of product yield and purity.
Technical scheme: in order to solve the problems of the technologies described above, the technical solution adopted in the present invention is: the preparation method of a kind of 1-hydroxyl-2-naphthoate, this method comprises the steps:
(1) synthetic: as in the reactor that the reflux distillation condenser is housed, to add triphenyl phosphite, heat temperature raising then, in the time of 90 ± 5 ℃, in reactor, drop into 1-hydroxyl-2-naphthoic acid more in batches, treat reinforced finish the back to continue to be incubated under 90 ± 5 ℃ of conditions to the reactor feed liquid transparent, wherein 1-hydroxyl-2-naphthoic acid: the mol ratio of triphenyl phosphite is 1: 0.2～10;
(2) crystallisation by cooling:, separate out crystal with the transparent feed liquid cooling of step (1);
(3) centrifugation: obtain 1-hydroxyl-2-naphthoate crude product and mother liquor with containing the centrifugation of crystalline feed liquid in the step (2);
(4) recrystallization: the crude product input is taken back in the decolouring still of flow condenser, in the decolouring still, add dehydrated alcohol then, be warming up to alcohol reflux, stop heating then, in this decolouring still, drop into the discoloring agent activated carbon decolorizing again, filter successively again, cooling, crystallization, centrifugation obtain 1-hydroxyl-2-naphthoate wet product, wherein dehydrated alcohol: the mol ratio of 1-hydroxyl-2-naphthoic acid is 1～45: 10;
(5) drying: resulting wet product in the step (4) are carried out drying obtain 1-hydroxyl-2-naphthoate.
In order to make triphenyl phosphite and 1-hydroxyl-2-naphthoic acid sufficient reacting, the feeding intake 0.5 hour at interval of every batch of 1-hydroxyl in the step (1)-2-naphthoic acid.
In order to improve product yield, the mother liquor in the step (3) is handled with sodium bicarbonate, divide oil-yielding stratum, again with the oil reservoir activated carbon decolorizing, the mother liquor that will decolour is back in the step (1) and applies mechanically then.
For the wet product of 1-hydroxyl-2-naphthoate are decomposed in drying process, what the drying in the step (5) adopted is vacuum-drying.
Beneficial effect: compared with prior art, advantage of the present invention is that technology is simple, easily industrialization, product yield can be brought up to more than 80%, purity reaches more than 99%.
Embodiment
The invention will be described in further detail below in conjunction with embodiment, should understand these embodiment and only be used to the present invention is described and be not used in and limit the scope of the invention.
Embodiment 1: add 270 kilograms of triphenyl phosphites in the 500L reactor of reflux distillation condenser is housed, heat temperature raising to 90 ℃, opening dog-house then divides 20 batches to drop into 200 kilograms of 1-hydroxyls-2-naphthoic acid, each 0.5 hour at interval, temperature 1-hydroxyl-2-naphthoic acid remains on 90 ± 5 ℃, and reinforced the end continues this temperature insulation 3 hours, it is transparent that feed liquid is observed in sampling, is reaction end.Cool off material to 5 ℃ then, suction filtration is centrifugal that filter cake be 1-hydroxyl-2-naphthoate crude product, about 250 kilograms.Mother liquor is handled with sodium bicarbonate, divides oil-yielding stratum to be used for applying mechanically next time behind the activated carbon decolorizing again.Afterwards the crude product input is taken back 500 liters of decolouring stills of flow condenser, add 200 kilograms of dehydrated alcohols, be warming up to alcohol reflux, 5 kilograms of gacs of cold slightly then input, decoloured 1 hour, press filtration to 500 rises crystallization kettle, has pressed postcooling to 5 ℃ to separate out mass crystallization, and suction filtration is centrifugal promptly get 1-hydroxyl-about 240 kilograms product that wet of 2-naphthoate product to doing, the vacuum of packing into rotary dryer, dry 225 kilograms of dry products, analyze content more than 99.0%, yield is 83%.
Embodiment 2: the mother liquor that adds treated mistake among the embodiment 1 in the 500L reactor of reflux distillation condenser is housed, add 130 kilograms of triphenyl phosphites again, heat temperature raising to 90 ℃, open dog-house then and divide 20 batches to drop into 200 kilograms of 1-hydroxyls-2-naphthoic acid, each 0.5 hour at interval, temperature 1-hydroxyl-2-naphthoic acid remained on about 90 ± 5 ℃, the reinforced end, continuation was this temperature insulation 3 hours, and it is transparent that feed liquid is observed in sampling, is reaction end.Cool off material to 5 ℃ then, suction filtration is centrifugal that filter cake be 1-hydroxyl-2-naphthoate crude product, about 295 kilograms.Filtrate is removed phenol through underpressure distillation, is used for behind the activated carbon decolorizing applying mechanically next time again.Afterwards the crude product input is taken back 500 liters of decolouring stills of flow condenser, add 220 kilograms of dehydrated alcohols, be warming up to alcohol reflux, 6 kilograms of gacs of cold slightly then input, decoloured 1 hour, press filtration to 500 rises crystallization kettle, has pressed postcooling to 5 ℃ to separate out mass crystallization, and suction filtration is centrifugal promptly get 1-hydroxyl-275 kilograms of product that wet of 2-naphthoate product to doing, the vacuum of packing into rotary dryer, dry 258 kilograms of dry products, analyze content more than 99.0%, yield about 91.4%.
Embodiment 3: add 66 kilograms of triphenyl phosphites in the 500L reactor of reflux distillation condenser is housed, heat temperature raising to 90 ℃, opening dog-house then divides 20 batches to drop into 200 kilograms of 1-hydroxyls-2-naphthoic acid, each 0.5 hour at interval, temperature 1-hydroxyl-2-naphthoic acid remains on 90 ± 5 ℃, the reinforced end, continuation was this temperature insulation 2 hours, it is transparent that feed liquid is observed in sampling, is reaction end, cools off material to 5 ℃ then, suction filtration is centrifugal that filter cake is 1-hydroxyl-2-naphthoate crude product, mother liquor is handled with sodium bicarbonate, divides oil-yielding stratum, again oil reservoir is used for applying mechanically next time after with activated carbon decolorizing.Afterwards the crude product input is taken back 500 liters of decolouring stills of flow condenser, add 40 kilograms of dehydrated alcohols, be warming up to alcohol reflux, 5 kilograms of gacs of cold slightly then input decoloured 1 hour, press filtration to 500 rises crystallization kettle, pressed postcooling to 5 ℃ to separate out mass crystallization, suction filtration is centrifugal promptly get the wet product of 1-hydroxyl-2-naphthoate to doing, and the vacuum of packing into rotary dryer is dried, analyze content more than 99.0%, yield about 80%.
Embodiment 4: the mother liquor that adds treated mistake among the embodiment 3 in the 500L reactor of reflux distillation condenser is housed, add 100 kilograms of triphenyl phosphites again, heat temperature raising to 90 ℃, open dog-house then and divide 20 batches to drop into 200 kilograms of 1-hydroxyls-2-naphthoic acid, each 0.5 hour at interval, temperature 1-hydroxyl-2-naphthoic acid remained on 90 ± 5 ℃, the reinforced end, continuation was this temperature insulation 3 hours, and it is transparent that feed liquid is observed in sampling, is reaction end.Cool off material to 5 ℃ then, suction filtration is centrifugal that filter cake be 1-hydroxyl-2-naphthoate crude product.Filtrate is removed phenol through underpressure distillation, is used for behind the activated carbon decolorizing applying mechanically next time again.Afterwards the crude product input is taken back 500 liters of decolouring stills of flow condenser, add 150 kilograms of dehydrated alcohols, be warming up to alcohol reflux, 5 kilograms of gacs of cold slightly then input decoloured 1 hour, press filtration to 500 rises crystallization kettle, pressed postcooling to 5 ℃ to separate out mass crystallization, suction filtration is centrifugal promptly get the wet product of 1-hydroxyl-2-naphthoate to doing, and the vacuum of packing into rotary dryer is dried, analyze content more than 99.0%, yield is 93%.
Embodiment 5: substantially the same manner as Example 1, different is involved raw material 1-hydroxyl-2-naphthoic acid: triphenyl phosphite: the mol ratio of dehydrated alcohol is 1: 5: 30.
Embodiment 6: substantially the same manner as Example 2, different is involved raw material 1-hydroxyl-2-naphthoic acid: triphenyl phosphite: the mol ratio of dehydrated alcohol is 1: 2: 20.
Embodiment 7: substantially the same manner as Example 3, different is involved raw material 1-hydroxyl-2-naphthoic acid: triphenyl phosphite: the mol ratio of dehydrated alcohol is 1: 7: 40.
Embodiment 8: substantially the same manner as Example 4, different is involved raw material 1-hydroxyl-2-naphthoic acid: triphenyl phosphite: the mol ratio of dehydrated alcohol is 1: 0.8: 10.
Claims (4)
1. the preparation method of 1-hydroxyl-2-naphthoate is characterized in that this method comprises the steps:
(1) synthetic: as in the reactor that the reflux distillation condenser is housed, to add triphenyl phosphite, heat temperature raising then, in the time of 90 ± 5 ℃, in reactor, drop into 1-hydroxyl-2-naphthoic acid more in batches, treat reinforced finish the back to continue to be incubated under 90 ± 5 ℃ of conditions to the reactor feed liquid transparent, wherein 1-hydroxyl-2-naphthoic acid: the mol ratio of triphenyl phosphite is 1: 0.2～10;
(2) crystallisation by cooling:, separate out crystal with the transparent feed liquid cooling of step (1);
(3) centrifugation: obtain 1-hydroxyl-2-naphthoate crude product and mother liquor with containing the centrifugation of crystalline feed liquid in the step (2);
(4) recrystallization: the crude product input is taken back in the decolouring still of flow condenser, in the decolouring still, add dehydrated alcohol then, be warming up to alcohol reflux, stop heating then, in this decolouring still, drop into the discoloring agent activated carbon decolorizing again, filter successively again, cooling, crystallization, centrifugation obtain 1-hydroxyl-2-naphthoate wet product, wherein dehydrated alcohol: the mol ratio of 1-hydroxyl-2-naphthoic acid is 1～45: 10;
(5) drying: resulting wet product in the step (4) are carried out drying obtain 1-hydroxyl-2-naphthoate.
2. the preparation method of a kind of 1-hydroxyl according to claim 1-2-naphthoate is characterized in that: the feeding intake 0.5 hour at interval of every batch of 1-hydroxyl in the step (1)-2-naphthoic acid.
3. the preparation method of a kind of 1-hydroxyl according to claim 1-2-naphthoate, it is characterized in that: the mother liquor in the step (3) is handled with sodium bicarbonate, divide oil-yielding stratum, again with the oil reservoir activated carbon decolorizing, the mother liquor that will decolour is back in the step (1) and applies mechanically then.
4. the preparation method of a kind of 1-hydroxyl according to claim 1-2-naphthoate is characterized in that: what the drying in the step (5) adopted is vacuum-drying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910263237 CN101928220B (en) | 2009-12-17 | 2009-12-17 | Preparation method of 1-hydroxyl-2-naphthoate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910263237 CN101928220B (en) | 2009-12-17 | 2009-12-17 | Preparation method of 1-hydroxyl-2-naphthoate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101928220A true CN101928220A (en) | 2010-12-29 |
| CN101928220B CN101928220B (en) | 2013-04-10 |
Family
ID=43367706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200910263237 Active CN101928220B (en) | 2009-12-17 | 2009-12-17 | Preparation method of 1-hydroxyl-2-naphthoate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101928220B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104478724A (en) * | 2015-01-09 | 2015-04-01 | 郑州盖科科技有限公司 | 6-hydroxy-2-naphthoate series coupling agent and synthetic method thereof |
| CN114014756A (en) * | 2021-12-24 | 2022-02-08 | 青岛科技大学 | Preparation method of 3-hydroxy-2-naphthoic acid phenyl ester |
| CN114181078A (en) * | 2021-12-24 | 2022-03-15 | 青岛科技大学 | Refining method of 3-hydroxy-2-naphthoic acid phenyl ester |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1603075A (en) * | 1977-10-24 | 1981-11-18 | Secr Defence | Liquid crystal esters containing naphthyl groups |
-
2009
- 2009-12-17 CN CN 200910263237 patent/CN101928220B/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104478724A (en) * | 2015-01-09 | 2015-04-01 | 郑州盖科科技有限公司 | 6-hydroxy-2-naphthoate series coupling agent and synthetic method thereof |
| CN114014756A (en) * | 2021-12-24 | 2022-02-08 | 青岛科技大学 | Preparation method of 3-hydroxy-2-naphthoic acid phenyl ester |
| CN114181078A (en) * | 2021-12-24 | 2022-03-15 | 青岛科技大学 | Refining method of 3-hydroxy-2-naphthoic acid phenyl ester |
| CN114014756B (en) * | 2021-12-24 | 2023-09-19 | 青岛科技大学 | Preparation method of 3-hydroxy-2-phenyl naphthoate |
| CN114181078B (en) * | 2021-12-24 | 2023-09-19 | 青岛科技大学 | Refining method of 3-hydroxy-2-phenyl naphthoate |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101928220B (en) | 2013-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101168522B (en) | Method for preparing high purity lutein crystal from marigold oil resin | |
| CN105646440A (en) | Refining and purifying method of lactide | |
| CN102911036A (en) | Method for obtaining high pure dicarboxylic acid | |
| CN101928225A (en) | Method for preparing N,N,N',N'-tetrakis(2-hydroxyethyl)adipamide | |
| CN110002992A (en) | A kind of refining methd of positive long-chain biatomic acid | |
| CN101928220B (en) | Preparation method of 1-hydroxyl-2-naphthoate | |
| CN101863912A (en) | Preparation method of cyclopropylboronic acid | |
| CN104031043B (en) | A kind of Moxifloxacin hydrochloride synthetic method | |
| CN101560188B (en) | Method for separating and purifying 2-methylimidazole crystal impurity | |
| CN101810262B (en) | Xylitol mother liquor crystallization method | |
| CN101928214A (en) | Method for synthesizing dexketoprofen trometamol | |
| CN110818534A (en) | Hydroquinone production process | |
| CN114292203B (en) | Preparation method of DL-panthenol | |
| CN101928278B (en) | (S)-4-[(4-chlorphenyl)(pyridine-2-yl)methoxyl]piperidinehydroxyphenpropionate and application thereof | |
| CN106148454B (en) | Preparation method of baohuoside I | |
| CN101182341A (en) | Method for purifying xylitol crystal | |
| CN107879979A (en) | A kind of preparation method of Dexmedetomidine | |
| CN109134403B (en) | Preparation method of 2-morpholine ethanesulfonic acid | |
| CN114634408B (en) | Purification method of ultraviolet light absorber oxybenzone | |
| CN113264822B (en) | Preparation method of disodium fumarate | |
| CN116199601B (en) | Refining and purifying process of high-content chlorothalonil | |
| CN114014756B (en) | Preparation method of 3-hydroxy-2-phenyl naphthoate | |
| CN114315627B (en) | Method for synthesizing doxycycline dehydrate by catalyzing with normal-temperature ionic liquid and zeolite | |
| CN114195755B (en) | Preparation method of glycolide | |
| CN111574462A (en) | Preparation method of sodium 5-ethyl-5-phenyl barbiturate |
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: TAICANG BIOCHEMICAL ENGINEERING CO., LTD. Free format text: FORMER OWNER: TAICANG YUNTONG CHEMICAL PLANT Effective date: 20130923 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20130923 Address after: 215433 No. 12 Binhai Road, Port Development Zone, Taicang port, Jiangsu, Taicang, China Patentee after: TAICANG YUNTONG BIOCHEMICAL ENGINEERING CO., LTD. Address before: 215433 No. 12 Binhai Road, Port Development Zone, Taicang port, Jiangsu, Taicang, China Patentee before: Taicang Yuntong Chemical Plant |
|
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
Address after: 215433 No. 12 Binhai Road, Petrochemical Development Zone, Taicang port, Taicang, Jiangsu Patentee after: Taicang express new Mstar Technology Ltd Address before: 215433 No. 12 Binhai Road, Port Development Zone, Taicang port, Taicang, Jiangsu Patentee before: TAICANG YUNTONG BIOCHEMICAL ENGINEERING CO., LTD. |