CN1413993A - Synthetic method of trithioaceton and its homologous compound - Google Patents
Synthetic method of trithioaceton and its homologous compound Download PDFInfo
- Publication number
- CN1413993A CN1413993A CN 01132011 CN01132011A CN1413993A CN 1413993 A CN1413993 A CN 1413993A CN 01132011 CN01132011 CN 01132011 CN 01132011 A CN01132011 A CN 01132011A CN 1413993 A CN1413993 A CN 1413993A
- Authority
- CN
- China
- Prior art keywords
- trithioaceton
- synthetic method
- homologue
- lewis acid
- trithioacetone
- 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.)
- Pending
Links
- NBNWHQAWKFYFKI-UHFFFAOYSA-N 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane Chemical compound CC1(C)SC(C)(C)SC(C)(C)S1 NBNWHQAWKFYFKI-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000010189 synthetic method Methods 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 15
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 14
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000011592 zinc chloride Substances 0.000 claims abstract description 7
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000012805 post-processing Methods 0.000 claims description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 239000011968 lewis acid catalyst Substances 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- 235000013599 spices Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 2
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 2
- 240000001890 Ribes hudsonianum Species 0.000 description 2
- 235000001466 Ribes nigrum Nutrition 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 240000002319 Citrus sinensis Species 0.000 description 1
- 235000005976 Citrus sinensis Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003845 household chemical Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for synthesizing trithioacetone and its homologs features the hydrogen sulfide and aceton solution take part in reaction under the catalysis of Lewis acid to obtain trithioacetone, and its post-treatment includes such steps as adding water to dissolving zinc chloride, adding benzene for extracting to make trithioacetone come in benzene layer, and distilling. Its advantages are simple post-treating, and high output rate.
Description
Technical field:
The present invention relates to the synthetic method of a kind of spices trithioaceton and homologue thereof.
Background technology:
This chemistry of trithioaceton is by name: 2,2,4,4,6, and the 6-vegolysen, 3,5-trithio hexane, it is at first found in the extract of beef and pork at first, is found in the composition analysis of some tropical fruits again afterwards.It has a kind of note of intensive sulphur sample, has the note and the taste of sweet nut sample simultaneously, and it can be applicable to also can be applicable in the spices such as nuts and meat in the fruit type spices such as strawberry, black currant, grape.In spices such as configuration black currant, sweet orange, play an important role.It also is widely used in household chemicals.Be applied to obviously to increase in the daily chemical products such as washing powder shampoo the delicate fragrance of product with the daily chemical essence that contains 2% trithioaceton, fragrance remaining time is prolonged.United States Patent (USP) 3958030 is described its synthetic method, is after reaction finishes to the aftertreatment of reacting, and with the unnecessary solvent acetone of vacuum pump underpressure distillation of 15mm mercury column, have good freezing plant to reclaim acetone.Rectificated remaining liquid is underpressure distillation again, obtains three sections of heating up in a steamer respectively, because there is a large amount of zinc chloride to have relatively difficulty of distillation, the 3rd section of heating up in a steamer second distillation obtain the certified products trithioaceton, but yield is lower.The present invention has done a large amount of improvement to the postprocessing working procedures of above-mentioned preparation on the basis of existing technology, invents a kind of novel synthesis of trithioaceton
Summary of the invention:
The synthetic method of trithioaceton and homologue thereof mainly comprises with the logical acetone soln of hydrogen sulfide synthetic trithioaceton under the lewis acid catalyst effect, it is characterized in that: the postprocessing working procedures of described synthetic method is: add the water dissolution zinc chloride and add benzene and extract, make trithioaceton enter the benzene layer, get trithioaceton through single flash.Wherein: lewis acid catalyst is: zinc dichloride, aluminum chloride, iron trichloride, boron trifluoride.The present invention is effective to the target compound with following structure:
Wherein: R
1, R
2And R
3Can be identical, also can be different.R can be a methyl, also can be hydrogen.The present invention can prepare following all cpds:
Temperature of reaction of the present invention is 0C-30C, and the reaction times is 5 hours-15 hours, and reacting final pH value is PH4-PH7.
The invention has the advantages that: simplified postprocessing working procedures, do not needed to have got rid of the interference of zinc chloride in postprocessing working procedures, improved yield with underpressure distillation, cold and reclaim acetone.
Embodiment:
Further specify embodiments of the invention below:
In Fume Hoods, add sulphur iron ore 500 grams of breaking into pieces (iron sulphide content 〉=70%) in 1000 milliliters of there-necked flasks, add 500 milliliters of concentrated hydrochloric acids in the dropping funnel in batches, drip off in 7 hours, the hydrogen sulfide that takes place imports scrubbing bottle by spherical condensating tube, and (interior dress concentrated hydrochloric acid) feeds reactor then.Reactor is by being equipped with three mouthfuls of reaction flasks that thermometer and spherical condensating tube are formed in mechanical stirrer, the hydrogen sulfide airway, and the prolong air outlet connects the aqueous sodium hydroxide solution tail gas absorber.Add 600 milliliters of acetone in the above-mentioned again reactor, 200 gram anhydrous chlorides of rase zinc powders, be cooled to below 10 ℃ under stirring, begin to feed hydrogen sulfide then, control hydrogen sulfide feeds speed and temperature of reaction is no more than 10 ℃ (water-soluble coolings), beginning reaction solution color pulverize redness, the back disappears, and hydrogen sulfide feeds progressively feculence oyster white of 7 hours afterreaction liquid, restir 1 hour at room temperature then, to going into separating funnel, add 600 ml waters, use twice extraction of 150 milliliters of benzene then, again with 150 ml waters washing benzene layer, normal pressure reclaims benzene (including small amount of acetone can reuse), thick oily underpressure distillation, 104-110/1Kpa, go out crude product 100-105 gram, content 90-95%, the separation column fractionation gets certified products trithioaceton 90-95 gram, content 〉=97% then.
Claims (4)
1, the synthetic method of trithioaceton and homologue thereof, mainly comprise and feed acetone soln with hydrogen sulfide, synthetic trithioaceton under the lewis acid catalyst effect, it is characterized in that: the postprocessing working procedures of described synthetic method is: add the water dissolution zinc chloride, and adding benzene extracts, make trithioaceton enter the benzene layer, get trithioaceton through single flash.
2, the synthetic method of trithioaceton according to claim 1 and homologue thereof is characterized in that: described lewis acid catalyst is: zinc dichloride, aluminum chloride, iron trichloride, boron trifluoride.
3, the synthetic method of trithioaceton according to claim 1 and homologue thereof is characterized in that: temperature of reaction is 0C-30C, and the reaction times is 5 hours-15 hours,
4, the synthetic method of trithioaceton according to claim 1 and homologue thereof is characterized in that: reacting final pH value is PH4-PH7.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01132011 CN1413993A (en) | 2001-10-26 | 2001-10-26 | Synthetic method of trithioaceton and its homologous compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01132011 CN1413993A (en) | 2001-10-26 | 2001-10-26 | Synthetic method of trithioaceton and its homologous compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1413993A true CN1413993A (en) | 2003-04-30 |
Family
ID=4671060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01132011 Pending CN1413993A (en) | 2001-10-26 | 2001-10-26 | Synthetic method of trithioaceton and its homologous compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1413993A (en) |
-
2001
- 2001-10-26 CN CN 01132011 patent/CN1413993A/en active Pending
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| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |