CN103772158A - Benzyl-2-naphthyl ether preparation method - Google Patents
Benzyl-2-naphthyl ether preparation method Download PDFInfo
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- CN103772158A CN103772158A CN201210408414.9A CN201210408414A CN103772158A CN 103772158 A CN103772158 A CN 103772158A CN 201210408414 A CN201210408414 A CN 201210408414A CN 103772158 A CN103772158 A CN 103772158A
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- benzyl
- naphthylether
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- beta naphthal
- naphthyl ether
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
Abstract
The invention relates to a preparation method of a thermosensitive sensitizer, and particularly relates to a benzyl-2-naphthyl ether preparation method. The benzyl-2-naphthyl ether preparation method provided by the invention is simple in operation, high in yield, safe, free of pollution and low in cost, benzyl chloride and 2-naphthol are used as raw materials for reaction under solvent-free conditions to obtain benzyl-2-naphthyl ether. The benzyl-2-naphthyl ether preparation method has the advantages of simple operation, less side reaction products, short reaction time, simple post treatment, high yield, no pollution, low cost, and suitability for industrialized production.
Description
Technical field:
The present invention relates to a kind of preparation method of temperature-sensitive sensitizing agent, more particularly, relate to a kind of preparation method of benzyl-2-naphthylether.
Background technology:
Electrothermal sensitive recording paper, as one of medium of thermal printing, is widely used in the fields such as fax, medical records, electric cash system, and its purposes is increasingly extensive, and market outlook are boundless.
At present electrothermal sensitive recording paper is because the difference aspect the use at novel material and heat sensitive paint formula causes electrothermal sensitive recording paper that different companies produces at color development susceptibility and reflect aspect luminosity having very large difference, in order to improve color development susceptibility and the inverse luminosity of electrothermal sensitive recording paper, and to a kind of chemical composition of adding in heat sensitive paint to realize the high sensitivity of electrothermal sensitive recording paper.This chemical composition of adding is just temperature-sensitive sensitizing agent.
Sensitizing agent has chemical sensitizer and optical sensitizer two classes.Optical sensitizer, because mostly being a kind of special dyestuff, claims again sensitizing dye, adds after this dyestuff, can make to feel color range and be extended to whole visible region.This sensitizing agent consumption is few, but photographic property is produced a very large impact.Heat sensitive dye starts from nineteen fifty, and the knot product violet lactone (CVL) of NCR Corp. of U.S. exploitation is at that time heat sensitive dye the earliest.Particularly facsimile recorder universal of the development of recording system along with information, the said firm in 1969 has developed again the turn black fluoran compound 0DBn of look of heat sensitive dye of new generation].After this heat sensitive dye is developing faster, and existing market prospect is boundless.
Benzyl-2-naphthylether, another name: benzyl-2-naphthalene ether, BON; CAS:613-62-7; Molecular formula; C
17h
14o, molecular weight: 234.3, structural formula is:
The traditional method of preparing benzyl-2-naphthylether is Williamson method, harsh but this synthetic method working condition requires, long reaction time, and complicated operation, product yield is low.Be exactly the phase-transfer catalysis synthetic method of domestic report in addition, although the method is simple to operate, yield is higher, is 80% left and right, needs the phase-transfer catalyst Tetrabutyl amonium bromide that price is higher, and aftertreatment is relatively complicated, and relative cost is higher.
Summary of the invention:
The present invention is exactly for the problems referred to above, provide a kind of simple to operate, yield is high, the preparation method of safety non-pollution, benzyl-2-naphthylether that cost is low.
In order to realize above-mentioned purpose of the present invention, the present invention adopts following technical scheme,
It is take Benzyl Chloride and beta naphthal as raw material, and under condition of no solvent, reaction obtains benzyl-2-naphthylether, and reaction equation is,
Preparation process is, the Benzyl Chloride and the beta naphthal that mole are 1.1～1.5:1 mixed to preferably 1.2:1, at 110-120 ℃, react 3～5 hours, then system temperature is down to 90 ℃, drips organic solvent and carry out crystallization, after filtering, being dried, obtain benzyl-2-naphthylether.
Described organic solvent is methyl alcohol, ethanol or propyl alcohol.
In reaction, add acid binding agent, the mol ratio of its addition and beta naphthal is 1.0～1.5:1.
Described acid binding agent is more than one in sodium carbonate, salt of wormwood, sodium hydroxide, potassium hydroxide.
The benzyl-2-naphthylether obtaining after filtering, being dried is continued to be added in water, and solid-liquid ratio is 1:5～10g/ml, is heated to 40-50 ℃, stirs 1 hour, filters, dry, obtains end product benzyl-2-naphthylether.
The mol ratio of acid binding agent and beta naphthal is 1.0:1.
The solid-liquid ratio of benzyl-2-naphthylether and water is 1:5 g/ml.
Beneficial effect of the present invention:
The present invention is simple to operate, and side reaction thing is few, and the reaction times is short, and aftertreatment is simple, and high yield is free from environmental pollution, and low cost, is suitable for suitability for industrialized production.
Accompanying drawing explanation:
Fig. 1 is the nuclear magnetic spectrogram of the embodiment of the present invention 1.
Embodiment;
Embodiment 1:
In 250 milliliters of three mouthfuls of reaction flasks, add successively 40 grams of beta naphthals, 19.5 grams of Benzyl Chlorides, be warming up to 110 ℃, now reactant is liquid state, then at this temperature, reacts 5 hours, my temperature is down to 90 ℃, drips 200 ml methanol, dropwise, be cooled to room temperature, stir 1 hour, filter to obtain white crystalline solid, 58 grams of dry product benzyl-2-naphthylethers, HPLC detection level 99%, yield 89.2%.
The infrared detection result of benzyl-2-naphthylether is: square ether (=c-o-c) charateristic avsorption band is 1256,1217,1218cm-1, the charateristic avsorption band of naphthalene nucleus is 842,818 cm-1, it is 758 cm-1 that 2-replaces position characteristic peak, the charateristic avsorption band 1628,1595 of Fang Huan (c=c), 1520 cm-1, the charateristic avsorption band of Fang Huan (=c-H) is 765,735 cm-1, the absorption peak completely dissolve of beta naphthal hydroxyl.Consistent with standard spectrogram.Confirmation product is benzyl-2-naphthylether.
Nuclear-magnetism detected result is shown in Fig. 1: 7 hydrogen on naphthalene nucleus between 7.2-7.7,5 hydrogen on phenyl ring on 7.19 position, methylene radical (CH-
2-) 2 hydrogen on 4.8 position.So structure is correct.
Embodiment 2:
In 250 milliliters of three mouthfuls of reaction flasks, add successively 40 grams of beta naphthals, 19.5 grams of Benzyl Chlorides, 29.5 grams of sodium carbonate, be warming up to 100 ℃, react 3 hours, cool the temperature to 90 ℃, drip 200 ml methanol, dropwise, be cooled to room temperature, stir 1 hour, filter to obtain white crystalline solid, be dried to obtain crude product benzyl-2-naphthylether, again this crude product is dissolved in 500 ml waters, is heated to 50 ℃, stir 1 hour, filter, 56 grams of dry white products benzyl-2-naphthylethers, HPLC detection level 99%, yield 86.1%.
Embodiment 3:
In 250 milliliters of three mouthfuls of reaction flasks, add successively 40 grams of beta naphthals, 19.5 grams of Benzyl Chlorides, 29.5 grams of sodium carbonate, be warming up to 100 ℃, react 3 hours, cool the temperature to 90 ℃, drip 200 milliliters of ethanol, dropwise, be cooled to room temperature, stir 1 hour, filter to obtain white crystalline solid, be dried to obtain crude product benzyl-2-naphthylether, again this crude product is dissolved in 500 ml waters, is heated to 50 ℃, stir 1 hour, filter, 54 grams of dry white products benzyl-2-naphthylethers, HPLC detection level 99%, yield 83.1%.
Claims (8)
1. the preparation method of benzyl-2-naphthylether, is characterized in that, it is take Benzyl Chloride and beta naphthal as raw material, and under condition of no solvent, reaction obtains benzyl-2-naphthylether, and reaction equation is,
2. the preparation method of benzyl-2-naphthylether according to claim 1, it is characterized in that, the Benzyl Chloride and the beta naphthal that mole are 1.1～1.5:1 are mixed, preferably 1.2:1, at 110-120 ℃, react 3～5 hours, then system temperature is down to 90 ℃, drips organic solvent and carry out crystallization, after filtering, being dried, obtain benzyl-2-naphthylether.
3. the preparation method of benzyl-2-naphthylether according to claim 2, is characterized in that, described organic solvent is methyl alcohol, ethanol or propyl alcohol.
4. the preparation method of benzyl-2-naphthylether according to claim 2, is characterized in that, adds acid binding agent in reaction, and the mol ratio of its addition and beta naphthal is 1.0～1.5:1.
5. the preparation method of benzyl-2-naphthylether according to claim 4, is characterized in that, described acid binding agent is more than one in sodium carbonate, salt of wormwood, sodium hydroxide, potassium hydroxide.
6. the preparation method of benzyl-2-naphthylether according to claim 4, it is characterized in that, the benzyl-2-naphthylether obtaining after filtering, being dried is continued to be added in water, solid-liquid ratio is 1:5～10g/ml, be heated to 40-50 ℃, stir 1 hour, filter, dry, obtain end product benzyl-2-naphthylether.
7. the preparation method of benzyl-2-naphthylether according to claim 4, is characterized in that, the mol ratio of acid binding agent and beta naphthal is 1.0:1.
8. the preparation method of benzyl-2-naphthylether according to claim 6, is characterized in that, the solid-liquid ratio of benzyl-2-naphthylether and water is 1:5 g/ml.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109970520A (en) * | 2019-04-08 | 2019-07-05 | 衢州学院 | A kind of preparation method of heat-sensitive paper sensitizer benzyl-2-naphthylether |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5352843A (en) * | 1992-06-06 | 1994-10-04 | Basf Aktiengesellschaft | Preparation of β-naphthyl benzyl ether |
| CN102276431A (en) * | 2011-05-17 | 2011-12-14 | 潍坊大有生物化工有限公司 | Synthesis method of benzyl-2-naphthyl ether thermosensitive sensibilized reagent |
-
2012
- 2012-10-23 CN CN201210408414.9A patent/CN103772158A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5352843A (en) * | 1992-06-06 | 1994-10-04 | Basf Aktiengesellschaft | Preparation of β-naphthyl benzyl ether |
| CN102276431A (en) * | 2011-05-17 | 2011-12-14 | 潍坊大有生物化工有限公司 | Synthesis method of benzyl-2-naphthyl ether thermosensitive sensibilized reagent |
Non-Patent Citations (1)
| Title |
|---|
| XIULI BU，ET AL.: "Organic base catalyzed O-alkylation of phenols under solvent-free condition", 《JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL》, vol. 259, 20 July 2006 (2006-07-20), pages 121 - 124 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109970520A (en) * | 2019-04-08 | 2019-07-05 | 衢州学院 | A kind of preparation method of heat-sensitive paper sensitizer benzyl-2-naphthylether |
| CN109970520B (en) * | 2019-04-08 | 2022-02-11 | 衢州学院 | Preparation method of thermosensitive paper sensitizer benzyl-2-naphthyl ether |
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Application publication date: 20140507 |