CN102267902A - Preparation method of di-n-butyl sebacate - Google Patents
Preparation method of di-n-butyl sebacate Download PDFInfo
- Publication number
- CN102267902A CN102267902A CN201110223352XA CN201110223352A CN102267902A CN 102267902 A CN102267902 A CN 102267902A CN 201110223352X A CN201110223352X A CN 201110223352XA CN 201110223352 A CN201110223352 A CN 201110223352A CN 102267902 A CN102267902 A CN 102267902A
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- CN
- China
- Prior art keywords
- preparation
- sebacic acid
- butyl
- butyl sebacic
- herbaceous plants
- 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.)
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- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 title abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 238000005406 washing Methods 0.000 claims abstract description 11
- 238000007670 refining Methods 0.000 claims abstract description 7
- KDMAKCTXYYDWPM-UHFFFAOYSA-N 2,2-dibutyldecanedioic acid Chemical compound CCCCC(CCCC)(C(O)=O)CCCCCCCC(O)=O KDMAKCTXYYDWPM-UHFFFAOYSA-N 0.000 claims description 30
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- 238000005886 esterification reaction Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 230000032050 esterification Effects 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 239000012043 crude product Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 239000011259 mixed solution Substances 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000292 calcium oxide Substances 0.000 claims description 9
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 9
- 239000000395 magnesium oxide Substances 0.000 claims description 9
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 9
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- 235000017550 sodium carbonate Nutrition 0.000 claims description 8
- -1 gac Chemical compound 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 14
- 238000001914 filtration Methods 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of di-n-butyl sebacate, and the preparation method comprises the following steps: esterifying, washing with water, removing alcohol, refining and filtering to obtain a di-n-butyl sebacate product. In the preparation method provided by the invention, a refining agent is added during the preparation process of di-n-butyl sebacate, so that the obtained product has lighter color and can be used as the product for sale with no need of high-vacuum refining treatment, and fully meets the technical requirements. By utilizing the preparation method provided by the invention, industrial production can be realized conveniently and the production efficiency is improved; and because a high-vacuum refining step is omitted during production, the investment of high-vacuum equipment is omitted, thus saving the equipment investment, lowering the production cost and improving the market competitiveness of the product.
Description
Technical field
The invention belongs to the organic compound preparation field, especially a kind of preparation method of di-n-butyl sebacic acid.
Background technology
Di-n-butyl sebacic acid, colourless clear liquid.Odorlessness.Can be miscible, water insoluble with ethanol, ether and acetone etc.Zero pour-11 ℃.349 ℃ of boiling points.Refractive index (n20D) 1.4395.176 ℃ of flash-points can be used as softening agent, Rubber Softener, often are used to makeup, in the middle of spices and the seasonings.
In recent years, in plastics industry and war production, di-n-butyl sebacic acid has more and more widely application as a kind of important organic compound and cold resistant plasticizer.The common production method of di-n-butyl sebacic acid is the direct esterification reaction, the color that obtains product is for yellow, be difficult to sell as product, must carry out further refining, the refinement treatment that promptly reduces pressure step, the problem that this type of preparation method exists: (1) is owing to needing to use expensive high-vacuum pump to realize in the decompression refinement treatment step, therefore, there is the problem that production unit is many, expense is high in this method, thereby is difficult to reduce cost; (2) because decompression refinement treatment step is to produce essential and very consuming time production stage in the di-n-butyl sebacic acid process, therefore, there is the problem that the production time is long, production efficiency is low in this method, is unfavorable for the raising of business economic benefit.
By retrieval, do not find the patent documentation relevant with this patent.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art part, the synthetic method of the di-n-butyl sebacic acid that provide a kind of and can save facility investment, reduces cost, production efficiency is high.
The present invention realizes that the technical scheme of purpose is as follows:
A kind of preparation method of di-n-butyl sebacic acid the steps include:
(1) esterification: with the certain herbaceous plants with big flowers diacid, propyl carbinol, the vitriol oil drop in the reactor, under the micro-vacuum condition, stir, and are heated to boiling reaction, keep the boiling reflux state, after not having moisture to generate, stop heating, treat mixed solution naturally cooling in the still;
(2) washing: will add water in the mixture after the esterification, after stirring, standing demix is removed water layer wherein;
(3) dealcoholysis: the mixture after will washing, dealcoholysis obtains the di-n-butyl sebacic acid crude product;
(4) refining: as will to add finishing agent in the crude product after the dealcoholysis, stir 1～3h;
(5) filter: the mixed solution after will making with extra care filters, and obtains the di-n-butyl sebacic acid product,
Described finishing agent is that yellow soda ash, calcium oxide, magnesium oxide, gac, diatomite mix, and its weight ratio is a yellow soda ash: calcium oxide: magnesium oxide: gac: diatomite=0.2: 1: 1: 2: 1.
And the weight ratio of described certain herbaceous plants with big flowers diacid and finishing agent is 1: 0.005～0.01.
And, described certain herbaceous plants with big flowers diacid, propyl carbinol, the weight ratio of the vitriol oil is the certain herbaceous plants with big flowers diacid: propyl carbinol: the vitriol oil=1: 1.15: 0.002～0.005.
And the weight ratio of described certain herbaceous plants with big flowers diacid and water is 2: 1.
And described reactor is the encloses container that has agitator, heating unit and backwater condensing works.
Advantage of the present invention and positively effect are:
1, the present invention adds finishing agent (yellow soda ash, calcium oxide, magnesium oxide, gac, diatomite mixture) in preparation di-n-butyl sebacic acid process, make the product colour that obtains more shallow, do not need the high vacuum refinement treatment promptly to can be used as product and sell, and meet the technical requirements fully.
2, the finishing agent that uses among the present invention is calcium oxide, magnesium oxide, gac, diatomite mixture, have cheap, the characteristics that are easy to purchase, quality product and prolonged storage stability have been guaranteed simultaneously, the preparation method realizes simply, easy to operate, saved investment in production equipment, improved production efficiency.
3, the present invention is convenient to realize suitability for industrialized production, enhance productivity, owing to when producing, saved the high vacuum purification step, and the input of no high-vacuum pump equipment, thus facility investment saved, reduce production costs, improved the competitiveness of product in market.
Embodiment
Below in conjunction with embodiment, the present invention is further described, and following embodiment is illustrative, is not determinate, can not limit protection scope of the present invention with following embodiment.
Embodiment 1
A kind of preparation method of di-n-butyl sebacic acid the steps include:
(1) step of esterification: have heating unit, the electricity stirring to one, drop into certain herbaceous plants with big flowers diacid double centner successively in 300 liters of reactors of thermometer water circulation condenser and vacuum oil water separator, 115 kilograms of propyl carbinols, 0.3 kilogram of the vitriol oil, under agitation, micro-vacuum is heated to boiling reaction simultaneously, keeps the boiling reflux state, constantly from water-and-oil separator, water sepn is gone out, after not having moisture to generate, stop heating, esterification stops.
(2) water-washing step: obtain to such an extent that add 50 kg water in the mixed solution after esterification, after stirring, standing demix is removed water layer wherein.
(3) dealcoholysis step: the mixture after will washing, dealcoholysis obtains the di-n-butyl sebacic acid crude product.
(4) purification step: add 0.5 kilogram of finishing agent (yellow soda ash, calcium oxide, magnesium oxide, gac, diatomite mixture were by 0.2: 1: 1: 2: 1 weight ratio mixes) in the crude product after dealcoholysis, mixed 1 hour.
(5) filtration step: refined mixed solution is filtered, and the liquid that obtains is the di-n-butyl sebacic acid finished product, this di-n-butyl sebacic acid content 99.5%, and color is less than No. 30 (platinum-cobalt colorimetric).
Embodiment 2
A kind of preparation method of di-n-butyl sebacic acid the steps include:
(1) step of esterification: have heating unit, the electricity stirring to one, drop into certain herbaceous plants with big flowers diacid double centner successively in 300 liters of reactors of thermometer water circulation condenser and vacuum oil water separator, 115 kilograms of propyl carbinols, 0.3 kilogram of the vitriol oil, under agitation, micro-vacuum is heated to boiling reaction simultaneously, keeps the boiling reflux state, constantly from water-and-oil separator, water sepn is gone out, after not having moisture to generate, stop heating, esterification stops.
(2) water-washing step: obtain to such an extent that add 50 kg water in the mixed solution after esterification, after stirring, standing demix is removed water layer wherein.
(3) dealcoholysis step: the mixture after will washing, dealcoholysis obtains the di-n-butyl sebacic acid crude product.
(4) purification step: add 0.6 kilogram of finishing agent (yellow soda ash, calcium oxide, magnesium oxide, gac, diatomite mixture were by 0.2: 1: 1: 2: 1 weight ratio mixes) in the crude product after dealcoholysis, mixed 1 hour.
(5) filtration step: refined mixed solution is filtered, and the liquid that obtains is the di-n-butyl sebacic acid finished product, this di-n-butyl sebacic acid content 99.5%, and color is less than No. 30 (platinum-cobalt colorimetric).
Embodiment 3
A kind of preparation method of di-n-butyl sebacic acid the steps include:
(1) step of esterification: have heating unit, the electricity stirring to one, drop into certain herbaceous plants with big flowers diacid double centner successively in 300 liters of reactors of thermometer water circulation condenser and vacuum oil water separator, 115 kilograms of propyl carbinols, 0.3 kilogram of the vitriol oil, under agitation, micro-vacuum is heated to boiling reaction simultaneously, keeps the boiling reflux state, constantly from water-and-oil separator, water sepn is gone out, after not having moisture to generate, stop heating, esterification stops.
(2) water-washing step: obtain to such an extent that add 50 kg water in the mixed solution after esterification, after stirring, standing demix is removed water layer wherein.
(3) dealcoholysis step: the mixture after will washing, dealcoholysis obtains the di-n-butyl sebacic acid crude product.
(4) purification step: add 0.7 kilogram of finishing agent (yellow soda ash, calcium oxide, magnesium oxide, gac, diatomite mixture were by 0.2: 1: 1: 2: 1 weight ratio mixes) in the crude product after dealcoholysis, mixed 1 hour.
(5) filtration step: refined mixed solution is filtered, and the liquid that obtains is the di-n-butyl sebacic acid finished product, this di-n-butyl sebacic acid content 99.5%, and color is less than No. 30 (platinum-cobalt colorimetric).
Claims (5)
1. the preparation method of a di-n-butyl sebacic acid the steps include:
(1) esterification: with the certain herbaceous plants with big flowers diacid, propyl carbinol, the vitriol oil drop in the reactor, under the micro-vacuum condition, stir, and are heated to boiling reaction, keep the boiling reflux state, after not having moisture to generate, stop heating, treat mixed solution naturally cooling in the still;
(2) washing: will add water in the mixture after the esterification, after stirring, standing demix is removed water layer wherein;
(3) dealcoholysis: the mixture after will washing, dealcoholysis obtains the di-n-butyl sebacic acid crude product;
(4) refining: as will to add finishing agent in the crude product after the dealcoholysis, stir 1～3h;
(5) filter: the mixed solution after will making with extra care filters, and obtains the di-n-butyl sebacic acid product.
It is characterized in that: described finishing agent is that yellow soda ash, calcium oxide, magnesium oxide, gac, diatomite mix, and its weight ratio is a yellow soda ash: calcium oxide: magnesium oxide: gac: diatomite=0.2: 1: 1: 2: 1.
2. the preparation method of di-n-butyl sebacic acid according to claim 1, it is characterized in that: the weight ratio of described certain herbaceous plants with big flowers diacid and finishing agent is 1: 0.005～0.01.
3. the preparation method of di-n-butyl sebacic acid according to claim 1 is characterized in that: described certain herbaceous plants with big flowers diacid, and propyl carbinol, the weight ratio of the vitriol oil is the certain herbaceous plants with big flowers diacid: propyl carbinol: the vitriol oil=1: 1.15: 0.002～0.005.
4. the preparation method of di-n-butyl sebacic acid according to claim 1, it is characterized in that: the weight ratio of described certain herbaceous plants with big flowers diacid and water is 2: 1.
5. the preparation method of di-n-butyl sebacic acid according to claim 1, it is characterized in that: described reactor is the encloses container that has agitator, heating unit and backwater condensing works.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110223352XA CN102267902A (en) | 2011-08-05 | 2011-08-05 | Preparation method of di-n-butyl sebacate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110223352XA CN102267902A (en) | 2011-08-05 | 2011-08-05 | Preparation method of di-n-butyl sebacate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102267902A true CN102267902A (en) | 2011-12-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110223352XA Pending CN102267902A (en) | 2011-08-05 | 2011-08-05 | Preparation method of di-n-butyl sebacate |
Country Status (1)
| Country | Link |
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| CN (1) | CN102267902A (en) |
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2011
- 2011-08-05 CN CN201110223352XA patent/CN102267902A/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 |
Application publication date: 20111207 |