CN110156744A - A kind of preparation method of hexa-atomic glycerine acetal - Google Patents
A kind of preparation method of hexa-atomic glycerine acetal Download PDFInfo
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- CN110156744A CN110156744A CN201910352925.5A CN201910352925A CN110156744A CN 110156744 A CN110156744 A CN 110156744A CN 201910352925 A CN201910352925 A CN 201910352925A CN 110156744 A CN110156744 A CN 110156744A
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- glycerine acetal
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
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Abstract
The invention belongs to prepare hexa-atomic glycerine acetal technical field, the especially preparation method the invention discloses a kind of hexa-atomic glycerine acetal, include the following steps, S1, the raw material including following molar part: 10-13 parts of glycerol, 4-6 parts of n-octaldehyde, 5-7 parts of catalyst；S2, the glycerol of above-mentioned molar part, n-octaldehyde, lauryl aldehyde, catalyst are put into reaction kettle simultaneously, reaction temperature is 45-55 DEG C, reaction time 5-6h, obtains cis- hexatomic ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring glycerine acetal mixture；S3 separates cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring glycerine acetal mixture with rectifying column to it.Hexatomic ring glycerine acetal and its derivative of the invention is applied on decomposable type surfactant and degradability biology based lubricating oil field, and yield is suitble to promote the use of up to 98.8%.
Description
Technical field
The present invention relates to prepare hexa-atomic glycerine acetal technical field more particularly to a kind of preparation side of hexa-atomic glycerine acetal
Method.
Background technique
Glycerine acetal or ketal compound are one synthesized as raw material by acetal or ketal reaction using glycerol and aldehydes or ketones
The important fine chemicals of class has potential in fields such as fuel additive, surfactant, lube oil additive, solvents
Application value.The fatty aldehyde contracting glycerol that glycerol and aliphatic aldehyde are synthesized by aldolisation is to synthesize decomposable type surfactant
Important hydrophobicity intermediate.The viscosity of glycerol is big, polarity is strong, with aliphatic aldehyde there is polar difference, the mutual not phase of the two
It is molten so that the condensation reaction of glycerol and aliphatic aldehyde has the problems such as reactivity is poor, products collection efficiency is low.
For this purpose, the present invention proposes a kind of preparation method of hexa-atomic glycerine acetal.
Summary of the invention
The purpose of the present invention is to solve disadvantages existing in the prior art, and a kind of hexa-atomic glycerine acetal proposed
Preparation method.
To achieve the goals above, present invention employs following technical solutions:
A kind of preparation method of hexa-atomic glycerine acetal, includes the following steps,
S1, the raw material including following molar part: 10-13 parts of glycerol, 4-6 parts of n-octaldehyde, 4-6 parts of lauryl aldehyde, 5-7 parts of catalyst；
The glycerol of above-mentioned molar part, n-octaldehyde, lauryl aldehyde, catalyst are put into reaction kettle, reaction temperature 45- by S2 simultaneously
55 DEG C, reaction time 5-6h, obtain cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerol
Acetal and trans- five-membered ring glycerine acetal mixture；
S3, by cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring
Glycerine acetal mixture separates it with rectifying column, thus cis- hexatomic ring glycerine acetal after being separated, trans- six
Member ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring glycerine acetal, cis- hexatomic ring required for both obtaining are sweet
Oily acetal and trans- hexatomic ring glycerine acetal.
Preferably, the catalyst is dodecyl benzene sulfonic acid, Amberlyst-36, Amberlyst-15, Nafion-
One of HNR-50, p-methyl benzenesulfonic acid, benzene sulfonic acid, sulfuric acid, nitric acid, hydrochloric acid are two or more.
Preferably, in the S1, the raw material including following molar part: 11-12 parts of glycerol, 4.5-5.5 parts of n-octaldehyde, laurel
4.5-5.5 parts of aldehyde, 5.5-6.5 parts of catalyst.
Preferably, in the S1, the raw material including following molar part: 11.5 parts of glycerol, 5 parts of n-octaldehyde, 5 parts of lauryl aldehyde,
6 parts of catalyst.
Preferably, in the S2, the glycerol of above-mentioned molar part, n-octaldehyde, lauryl aldehyde, catalyst are put into reaction kettle simultaneously
In, reaction temperature is 50 DEG C, reaction time 5.5h, obtains cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, suitable
Formula five-membered ring glycerine acetal and trans- five-membered ring glycerine acetal mixture.
Preferably, the molar ratio of the n-octaldehyde and lauryl aldehyde is 1:1.
Compared with prior art, the beneficial effects of the present invention are: passing through exploitation solvent-free system or green safe solvent body
It is the ideal process that synthesis technology is counted as Search green chemistry, realizes atom economy, hexatomic ring glycerine acetal of the invention
And its derivative is in the application of decomposable type surfactant and degradability biology based lubricating oil field, yield up to 98.8%,
It is suitble to promote the use of.
Specific embodiment
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.
Embodiment one
A kind of preparation method of hexa-atomic glycerine acetal proposed by the present invention, includes the following steps,
S1, the raw material including following molar part: 10 parts of glycerol, 4 parts of n-octaldehyde, 4 parts of lauryl aldehyde, 5 parts of catalyst；
The glycerol of above-mentioned molar part, n-octaldehyde, lauryl aldehyde, catalyst are put into reaction kettle, reaction temperature 45 by S2 simultaneously
DEG C, reaction time 5h obtains cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerine acetal
With trans- five-membered ring glycerine acetal mixture；
S3, by cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring
Glycerine acetal mixture separates it with rectifying column, thus cis- hexatomic ring glycerine acetal after being separated, trans- six
Member ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring glycerine acetal, cis- hexatomic ring required for both obtaining are sweet
Oily acetal and trans- hexatomic ring glycerine acetal.
In the present invention, the catalyst is sulfuric acid.
Embodiment two
A kind of preparation method of hexa-atomic glycerine acetal proposed by the present invention, includes the following steps,
S1, the raw material including following molar part: 11.5 parts of glycerol, 5 parts of n-octaldehyde, 5 parts of lauryl aldehyde, 6 parts of catalyst；
The glycerol of above-mentioned molar part, n-octaldehyde, lauryl aldehyde, catalyst are put into reaction kettle, reaction temperature 50 by S2 simultaneously
DEG C, reaction time 5.5h obtains cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerol acetonide
Aldehyde and trans- five-membered ring glycerine acetal mixture；
S3, by cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring
Glycerine acetal mixture separates it with rectifying column, thus cis- hexatomic ring glycerine acetal after being separated, trans- six
Member ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring glycerine acetal, cis- hexatomic ring required for both obtaining are sweet
Oily acetal and trans- hexatomic ring glycerine acetal.
In the present invention, the catalyst is dodecyl benzene sulfonic acid.
Embodiment three
A kind of preparation method of hexa-atomic glycerine acetal proposed by the present invention, includes the following steps,
S1, the raw material including following molar part: 13 parts of glycerol, 6 parts of n-octaldehyde, 6 parts of lauryl aldehyde, 7 parts of catalyst；
The glycerol of above-mentioned molar part, n-octaldehyde, lauryl aldehyde, catalyst are put into reaction kettle, reaction temperature 55 by S2 simultaneously
DEG C, reaction time 6h obtains cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerine acetal
With trans- five-membered ring glycerine acetal mixture；
S3, by cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring
Glycerine acetal mixture separates it with rectifying column, thus cis- hexatomic ring glycerine acetal after being separated, trans- six
Member ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring glycerine acetal, cis- hexatomic ring required for both obtaining are sweet
Oily acetal and trans- hexatomic ring glycerine acetal.
In the present invention, the catalyst is p-methyl benzenesulfonic acid.
The present invention is counted as developing greenization by exploitation solvent-free system or green safe dicyandiamide solution synthesis technology
The ideal process of atom economy is learned, realizes, hexatomic ring glycerine acetal of the invention and its derivative are in decomposable type surface-active
It is applied on agent and degradability biology based lubricating oil field, yield is suitble to promote the use of up to 98.8%.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Anyone skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.
Claims (6)
1. a kind of preparation method of hexa-atomic glycerine acetal, which is characterized in that include the following steps,
S1, the raw material including following molar part: 10-13 parts of glycerol, 4-6 parts of n-octaldehyde, 4-6 parts of lauryl aldehyde, 5-7 parts of catalyst；
The glycerol of above-mentioned molar part, n-octaldehyde, lauryl aldehyde, catalyst are put into reaction kettle, reaction temperature 45- by S2 simultaneously
55 DEG C, reaction time 5-6h, obtain cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerol
Acetal and trans- five-membered ring glycerine acetal mixture；
S3, by cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring
Glycerine acetal mixture separates it with rectifying column, thus cis- hexatomic ring glycerine acetal after being separated, trans- six
Member ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring glycerine acetal, cis- hexatomic ring required for both obtaining are sweet
Oily acetal and trans- hexatomic ring glycerine acetal.
2. a kind of preparation method of hexa-atomic glycerine acetal according to claim 1, which is characterized in that the catalyst is ten
Dialkyl benzene sulfonic acids, Amberlyst-36, Amberlyst-15, Nafion-HNR-50, p-methyl benzenesulfonic acid, benzene sulfonic acid, sulfuric acid,
One of nitric acid, hydrochloric acid are two or more.
3. a kind of preparation method of hexa-atomic glycerine acetal according to claim 1, which is characterized in that in the S1, including
The raw material of following molar part: 11-12 parts of glycerol, 4.5-5.5 parts of n-octaldehyde, 4.5-5.5 parts of lauryl aldehyde, 5.5-6.5 parts of catalyst.
4. a kind of preparation method of hexa-atomic glycerine acetal according to claim 1, which is characterized in that in the S1, including
The raw material of following molar part: 11.5 parts of glycerol, 5 parts of n-octaldehyde, 5 parts of lauryl aldehyde, 6 parts of catalyst.
5. a kind of preparation method of hexa-atomic glycerine acetal according to claim 1, which is characterized in that, will be upper in the S2
It states the glycerol of molar part, n-octaldehyde, lauryl aldehyde, catalyst while being put into reaction kettle, reaction temperature is 50 DEG C, and the reaction time is
5.5h obtains cis- hexatomic ring glycerine acetal, trans- hexatomic ring glycerine acetal, cis- five-membered ring glycerine acetal and trans- five-membered ring
Glycerine acetal mixture.
6. a kind of preparation method of hexa-atomic glycerine acetal according to claim 1, which is characterized in that the n-octaldehyde and the moon
The molar ratio of cinnamic aldehyde is 1:1.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8901165B2 (en) * | 2009-10-02 | 2014-12-02 | Cognis Ip Management Gmbh | Alkoxylated glycerol acetals and their derivatives |
| WO2015051525A1 (en) * | 2013-10-11 | 2015-04-16 | Rhodia Operations | Synthesis of acetal/ketal |
| CN105218511A (en) * | 2015-10-12 | 2016-01-06 | 太原理工大学 | A kind of alkanoic contracting glycerine Di-sodium Sulfo-succinate Mono Est-er and preparation technology thereof |
| CN106632229A (en) * | 2015-11-04 | 2017-05-10 | 中国科学院大连化学物理研究所 | Preparation method of cyclic acetal |
| CN106946840A (en) * | 2017-04-11 | 2017-07-14 | 太原理工大学 | A kind of two glycerine monoacetals and its preparation method and application |
| CN109641866A (en) * | 2016-12-27 | 2019-04-16 | 花王株式会社 | The manufacturing method of monoglyceride |
-
2019
- 2019-04-29 CN CN201910352925.5A patent/CN110156744A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8901165B2 (en) * | 2009-10-02 | 2014-12-02 | Cognis Ip Management Gmbh | Alkoxylated glycerol acetals and their derivatives |
| WO2015051525A1 (en) * | 2013-10-11 | 2015-04-16 | Rhodia Operations | Synthesis of acetal/ketal |
| CN105218511A (en) * | 2015-10-12 | 2016-01-06 | 太原理工大学 | A kind of alkanoic contracting glycerine Di-sodium Sulfo-succinate Mono Est-er and preparation technology thereof |
| CN106632229A (en) * | 2015-11-04 | 2017-05-10 | 中国科学院大连化学物理研究所 | Preparation method of cyclic acetal |
| CN109641866A (en) * | 2016-12-27 | 2019-04-16 | 花王株式会社 | The manufacturing method of monoglyceride |
| CN106946840A (en) * | 2017-04-11 | 2017-07-14 | 太原理工大学 | A kind of two glycerine monoacetals and its preparation method and application |
Non-Patent Citations (5)
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|---|
| ANDRZEJ PIASECKI等: "An Efficient Method for the Preparation of Pure Long-Chain CIS-and Trans-2-n-Alkyl-5-Hydroxy-1,3-Dioxanes", 《SYNTHETIC COMMUNICATIONS》 * |
| ANDRZEJ PIASECKI等: "Synthesis and Surface Properties of Chemodegradable Anionic Surfactants: Diastereomeric (2-n-alkyl-1,3-dioxan-5-yl) Sulfates with Monovalent Counter-Ions", 《JOURNAL OF SURFACTANTS AND DETERGENTS》 * |
| ANDRZEJ PIASECKI等: "Synthesis and Surface Properties of Chemodegradable Anionic Surfactants: Sodium (2-n-Alkyl-1,3-Dioxan-5-yl)Sulfates", 《JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY 》 * |
| ANDRZEJ PIASECKI等: "Synthesis, Surface Properties, and Hydrolysis of Chemodegradable Anionic Surfactants: Diastereomerically Pure Sodium cis- and trans-(2-n-Alkyl-1,3-dioxan-5-yl) Sulfates", 《LANGMUIR》 * |
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Application publication date: 20190823 |