CN102701911A - A method for purification and enhanced stability of alkynol compounds - Google Patents
A method for purification and enhanced stability of alkynol compounds Download PDFInfo
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- CN102701911A CN102701911A CN2011100746776A CN201110074677A CN102701911A CN 102701911 A CN102701911 A CN 102701911A CN 2011100746776 A CN2011100746776 A CN 2011100746776A CN 201110074677 A CN201110074677 A CN 201110074677A CN 102701911 A CN102701911 A CN 102701911A
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- alkynol
- methyl
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- enhanced stability
- stability
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000000746 purification Methods 0.000 title abstract description 7
- 150000002576 ketones Chemical class 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 10
- -1 isobutyl- Chemical group 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 235000010265 sodium sulphite Nutrition 0.000 claims description 5
- 230000002708 enhancing effect Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- XRCRJFOGPCJKPF-UHFFFAOYSA-N 2-butylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=CC=C1O XRCRJFOGPCJKPF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract description 2
- CIHXIRAAMAUYLZ-UHFFFAOYSA-N [K+].[K+].[C-]#[C-] Chemical compound [K+].[K+].[C-]#[C-] CIHXIRAAMAUYLZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003112 inhibitor Substances 0.000 abstract description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 2
- 238000001816 cooling Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QXLPXWSKPNOQLE-UHFFFAOYSA-N methylpentynol Chemical class CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002512 suppressor factor Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for purification and enhanced stability of alkynol compounds. The invention is characterized by including the following steps successively: adding potassium tert-butoxide to tetrahydrofuran, feeding acetylene gas after cooling to obtain potassium acetylide, adding ketone dropwise, pouring the reaction solution into water and getting the alkynol by hydrolyzing, removing the unreacted ketone in the crude alkynol with sodium bisulfite, distilling to obtain a product with purity over 99%, and adding a polymerization inhibitor to the qualified alkynol product to enhance the stability. The method help to solve the problems that the alkynol products produced in the prior art are low in purity, unqualified in appearance, and low in additional value.
Description
Technical field
The present invention relates to a kind of purification of alkynol compounds and the method for enhanced stability.
Background technology
Alkynol compounds with following structure is a series of important fine chemical products in medicine, synthetic materials, field of petrochemical industry widespread use.Its main application has: (1) is used as the stablizer that addition-type silicon rubber stores and produces, addition reaction of silicon with hydrogen suppressor factor as the midbody (2) of synthetic medicine, agricultural chemicals, terpenes spices; (3) as the siccative of printing ink, paint and coating; (4) as the lustering agent of nickel plating or copper; (5) as corrosion inhibitors for acidic media, viscosity stabilizer, viscosity depressant etc.
The alkynol compounds has following several kinds of compound methods usually:
(1) acetylene gas is fed in the tetrahydrofuran solution of potassium tert.-butoxide prepares potassium acetylide, prepare alkynol with reactive ketone afterwards.This method reaction conditions is relatively gentleer, simple to operate, is fit to suitability for industrialized production (Scheme 1).
(2) in liquefied ammonia, add sodium amide or Lithamide (sodium Metal 99.5 or metallic lithium) back feeding acetylene gas, adding ketone wherein afterwards, reaction obtains alkynol.As solvent, the temperature that reaction needed is lower needs the sodium amide (Lithamide) or the sodium Metal 99.5 (lithium) of hazardous to this method simultaneously, and is all higher to operation and equipment requirements, is unfavorable for suitability for industrialized production (Scheme 2) with liquefied ammonia.
(3) obtain alkynol with the acetylene magnesium halide as ethynylation reagent and reactive ketone.This method need at first prepare grignard reagent, obtains the acetylene magnesium halide with acetylene reaction afterwards, the low suitability for industrialized production (Scheme 3) that is not suitable for of this route complex operation, yield.
No matter adopt above-mentioned which kind of compound method, all can have unreacted completely raw ketone be present in the product, cause product purity lower, simultaneously because long-time placement of alkynol has polymkeric substance and produces and make the product jaundice.This alkynol series products purity that just causes selling on present most of market is lower, and color is dark, inferior quality.
Summary of the invention
Problems such as the object of the invention is to provide a kind of the have purification of following general formula alkynol compounds and the method for enhanced stability, and the alkynol compounds purity that has solved present prior art production is lower, and outward appearance is defective, and added value is low.
Wherein, R
1With R
2Be identical or different substituting group: R
1Be methyl, R
2It is methyl; R
1Be methyl, R
2It is ethyl; R
1Be methyl, R
2It is propyl group; R
1Be methyl, R
2It is isobutyl-; R
1Be methyl, R
2It is the tertiary butyl; R
1Be methyl, R
2It is vinyl; R
1Be ethyl, R
2It is ethyl; R
1Be isobutyl-, R
2It is isobutyl-; R
1Be phenyl, R
2It is phenyl.
The compound that also comprises formula:
In order to solve prior art problems, technical scheme provided by the invention is: a kind of purification of alkynol compounds and enhanced stability method.It is characterized in that may further comprise the steps successively:
(1) purifying of alkynol
Contain unreacted completely the bullion alkynol of raw ketone handle with aqueous solution of sodium bisulfite, unreacted ketone is removed, the distillation, obtain the specification product of purity more than 99%.
(2) enhancing of alkynol stability
In qualified alkynol product, add stopper, can strengthen the stability of product.
The consumption of sodium sulfite anhy 96 is confirmed according to the content of alkynol bullion in the said step (1), behind the purifying product purity greater than 99% and purification yield greater than 90%.
Preferred stopper is Resorcinol, MEHQ, toluhydroquinone, p-ten.-butylcatechol, 2-Tert. Butyl Hydroquinone in the said step (2), and add-on is preferably 0.2～0.5 ‰.
Embodiment
Below in conjunction with embodiment the present invention is further specified, embodiment is used to explain the present invention rather than is used to limit scope of the present invention.Simultaneously, after having read content of the present invention, those skilled in the art can do various changes and modification to the present invention, and these equivalent form of values fall within the application's appended claims institute restricted portion equally.
The preparation of embodiment 1:1-ethynyl-1-hexalin
Add the 150L THF in the reaction kettle, stir adding potassium tert.-butoxide 22.4Kg down, be cooled to 0 ℃, feed acetylene gas; Controlled temperature is ventilated after 4 hours below 5 ℃, and logical acetylene gas limit, limit drips pimelinketone 19.8Kg; Finish, stirring reaction 2 hours, controlled temperature is below 0 ℃.Reaction solution is poured in the frozen water, and water layer is used dichloromethane extraction, merges organic layer, and anhydrous sodium sulfate drying concentrates, underpressure distillation, the cut of 52-54 ℃/2mm of collection.Obtain weak yellow liquid 21.7Kg, yield 87.5%, purity 95% (detecting) with the GC method.
The purifying of embodiment 2:1-ethynyl-1-hexalin
Bullion charging capacity and productive rate
In reaction flask, add entry, add sodium sulfite anhy 96 then, after treating to dissolve fully, in reaction solution, add 1-ethynyl-1-hexalin bullion.
Heated and stirred 1 hour, stopped reaction.Static separatory, collected organic layer, water layer is used ethyl acetate extraction, merges organic layer, concentrates, and distillation obtains specification product.
The enhancing of embodiment 3:1-ethynyl-1-hexalin stability
Qualified 1-ethynyl-1-hexalin is investigated in following condition respectively.
Result: add stopper the stability of 1-ethynyl-1-hexalin is strengthened greatly, improve quality.
The preparation of embodiment 4:2-ethynyl-2-butanols
Add the 150L THF in the reaction kettle, stir adding potassium tert.-butoxide 22.4Kg down, be cooled to 0 ℃, feed acetylene gas; Controlled temperature is ventilated after 4 hours below 5 ℃, and logical acetylene gas limit, limit drips butanone 14.5Kg; Finish, stirring reaction 2 hours, controlled temperature is below 0 ℃.Reaction solution is poured in the frozen water, and water layer is used dichloromethane extraction, merges organic layer, and anhydrous sodium sulfate drying concentrates, and 120-122 ℃ cut is collected in distillation.Obtain weak yellow liquid 16.8Kg, yield 85.5%, purity 96% (detecting) with the GC method.
The purifying of embodiment 5:2-ethynyl-2-butanols
Bullion charging capacity and productive rate
In reaction flask, add entry, add sodium sulfite anhy 96 then, after treating to dissolve fully, in reaction solution, add 2-ethynyl-2-butanols bullion.
Heated and stirred 1 hour, stopped reaction.Static separatory, collected organic layer, water layer is used ethyl acetate extraction, merges organic layer, concentrates, and distillation obtains specification product.
The enhancing of embodiment 6:2-ethynyl-2-butanols stability
Qualified 2-ethynyl-2-butanols is investigated in following condition respectively.
Result: add stopper the stability of 2-ethynyl-2-butanols is strengthened greatly, improve quality.
Claims (16)
1. the purifying of the alkynol compounds with following general formula and the method for enhanced stability:
Wherein, R
1With R
2Being identical or different fatty substituting group, aromatic substituent, also can be the part of cyclic substituents.
2. R wherein according to claim 1,
1Be methyl, R
2It is methyl.
3. R wherein according to claim 1,
1Be methyl, R
2It is ethyl.
4. R wherein according to claim 1,
1Be methyl, R
2It is propyl group.
5. R wherein according to claim 1,
1Be methyl, R
2It is isobutyl-.
6. R wherein according to claim 1,
1Be methyl, R
2It is the tertiary butyl.
7. R wherein according to claim 1,
1Be methyl, R
2It is vinyl.
8. R wherein according to claim 1,
1Be ethyl, R
2It is ethyl.
9. R wherein according to claim 1,
1Be isobutyl-, R
2It is isobutyl-.
10. according to claim 1, comprising the compound of formula.
11. according to claim 1, comprising the compound of formula.
12. R wherein according to claim 1,
1Be phenyl, R
2It is phenyl.
13. according to claim 1, the method for the purifying of alkynol compounds and enhanced stability is characterized in that said method comprises the steps:
(1) purifying of alkynol compounds
The bullion alkynol is handled with sodium sulfite anhy 96 unreacted ketone is removed, and distillation obtains the product of purity more than 99%.
(2) enhancing of alkynol compounds stability
In qualified alkynol compounds, add stopper, can enhanced stability.
14., it is characterized in that the consumption of sodium sulfite anhy 96 in the said step (1) is confirmed according to the content of alkynol bullion according to method described in the claim 13.
15., it is characterized in that the stopper in the said step (2) is preferably Resorcinol, MEHQ, toluhydroquinone, p-ten.-butylcatechol, 2-Tert. Butyl Hydroquinone according to method described in the claim 13.
16., it is characterized in that the add-on of stopper is preferably 0.2～0.5 ‰ according to method described in the claim 15.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100746776A CN102701911A (en) | 2011-03-28 | 2011-03-28 | A method for purification and enhanced stability of alkynol compounds |
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| CN2011100746776A CN102701911A (en) | 2011-03-28 | 2011-03-28 | A method for purification and enhanced stability of alkynol compounds |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113188A (en) * | 2011-11-17 | 2013-05-22 | 河北百灵威超精细材料有限公司 | Novel low-cost synthesis method of alkynol compounds |
| CN103896737A (en) * | 2014-03-31 | 2014-07-02 | 南京工业大学 | Method for preparing propargyl alcohol by utilizing microstructure reactor |
| CN104193567A (en) * | 2014-07-07 | 2014-12-10 | 石河子大学 | Method for simply and efficiently preparing efavirenz intermediates |
| CN104744211A (en) * | 2013-12-27 | 2015-07-01 | 上虞新和成生物化工有限公司 | An alkynol preparing method |
| CN110143849A (en) * | 2019-06-05 | 2019-08-20 | 山东新和成维生素有限公司 | A kind of preparation method of acetylenic alcohol |
| CN110467519A (en) * | 2019-09-16 | 2019-11-19 | 万华化学集团股份有限公司 | A kind of acetylation method |
| CN112041353A (en) * | 2018-03-07 | 2020-12-04 | 丸善石油化学株式会社 | Novel difunctional (meth)acrylate compounds and polymers |
| WO2022016317A1 (en) * | 2020-07-20 | 2022-01-27 | 万华化学集团股份有限公司 | Separation method for 2-methyl-3-butyne-2-ol |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113188A (en) * | 2011-11-17 | 2013-05-22 | 河北百灵威超精细材料有限公司 | Novel low-cost synthesis method of alkynol compounds |
| CN104744211A (en) * | 2013-12-27 | 2015-07-01 | 上虞新和成生物化工有限公司 | An alkynol preparing method |
| CN104744211B (en) * | 2013-12-27 | 2017-04-12 | 上虞新和成生物化工有限公司 | An alkynol preparing method |
| CN103896737A (en) * | 2014-03-31 | 2014-07-02 | 南京工业大学 | Method for preparing propargyl alcohol by utilizing microstructure reactor |
| CN104193567A (en) * | 2014-07-07 | 2014-12-10 | 石河子大学 | Method for simply and efficiently preparing efavirenz intermediates |
| CN104193567B (en) * | 2014-07-07 | 2018-01-12 | 石河子大学 | A kind of simple method for efficiently preparing efavirenz intermediate |
| CN112041353A (en) * | 2018-03-07 | 2020-12-04 | 丸善石油化学株式会社 | Novel difunctional (meth)acrylate compounds and polymers |
| CN110143849A (en) * | 2019-06-05 | 2019-08-20 | 山东新和成维生素有限公司 | A kind of preparation method of acetylenic alcohol |
| WO2020244020A1 (en) * | 2019-06-05 | 2020-12-10 | 浙江新和成股份有限公司 | Method for preparing alkynol |
| CN110467519A (en) * | 2019-09-16 | 2019-11-19 | 万华化学集团股份有限公司 | A kind of acetylation method |
| CN110467519B (en) * | 2019-09-16 | 2022-08-05 | 万华化学集团股份有限公司 | Ethynylation method |
| WO2022016317A1 (en) * | 2020-07-20 | 2022-01-27 | 万华化学集团股份有限公司 | Separation method for 2-methyl-3-butyne-2-ol |
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Application publication date: 20121003 |