CN104774560A - Preparation method of rosin glycerin ester - Google Patents
Preparation method of rosin glycerin ester Download PDFInfo
- Publication number
- CN104774560A CN104774560A CN201410020296.3A CN201410020296A CN104774560A CN 104774560 A CN104774560 A CN 104774560A CN 201410020296 A CN201410020296 A CN 201410020296A CN 104774560 A CN104774560 A CN 104774560A
- Authority
- CN
- China
- Prior art keywords
- rosin
- glycerine
- glycerin
- ester
- esterification
- 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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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 100
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 66
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 66
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 235000011187 glycerol Nutrition 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- -1 glycerin ester Chemical class 0.000 title abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 235000010985 glycerol esters of wood rosin Nutrition 0.000 claims description 12
- 150000007524 organic acids Chemical group 0.000 claims description 2
- 230000032050 esterification Effects 0.000 abstract description 17
- 238000005886 esterification reaction Methods 0.000 abstract description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 description 7
- 238000007599 discharging Methods 0.000 description 6
- 125000005908 glyceryl ester group Chemical group 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004831 Hot glue Substances 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- VLTOSDJJTWPWLS-UHFFFAOYSA-N pent-2-ynal Chemical group CCC#CC=O VLTOSDJJTWPWLS-UHFFFAOYSA-N 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of rosin glycerin ester. The preparation method utilizes a reaction of rosin and glycerin. Aiming at preparing high-softening point rosin glycerin ester, rosin is added into a reactor by one step, glycerin is added into the reactor by 2-4 steps and a mole ratio of rosin to glycerin is 3: 1. Aiming at preparing low-softening point rosin glycerin ester, glycerin is added into the reactor by one step, rosin is added into the reactor by 2-4 steps after glycerin addition and a mole ratio of rosin to glycerin is 1.5: 1 to 2.5: 1. The rosin glycerin ester has a controllable softening point and good practicability. The preparation method has simple processes and high generation efficiency. The method for controlling an esterification product softening point is suitable for rosin and glycol esterification (wherein the product is rosin ethylene glycol ester), rosin and pentaerythritol esterification (wherein the product is rosin pentaerythritol ester) and benzene esterification.
Description
Technical field
The invention belongs to technical field of composite materials, be specifically related to a kind of preparation method of ester gum.
Background technology
Obtain ester gum with rosin and glycerine esterification, use rosin derivative (such as: staybelite, polymerized rosin etc.) and glycerine esterification also can obtain the glyceryl ester of derivative equally.China is the rosin production big country in the whole world, and annual production is about 40-50 ten thousand tons, accounts for more than 60% of global rosin output.By rosin and esterification of derivatives thereof, may be used for chewing gum base etc. in hot melt adhesive, ink, road paint, textile auxiliary and foodstuffs industry, become a sizable industry.
And in all application, the softening temperature of glyceryl ester is very important performance index, there is different softening temperature requirements in different use field.At present, typical esterification technique is that the glycerine of molten rosin and molecule proportioning, catalyzer are dropped into esterifying kettle, reaction is carried out at 230-260 DEG C, constantly steam the water of generation, general through 8-12 hour esterification, can obtain product-glyceryl ester, reaction terminates rear mensuration softening temperature, the product obtaining certain softening temperature passive often.If require that softening temperature is high, the rosin of high softening-point or part dimerization colophonium often to be selected to be raw material.If require that the softening temperature of product glyceryl ester is low, need the rosin raw material selecting low softening point, or partial hydrogenation rosin raw material, namely depend on molecular weight and the molecular structure of raw material to a great extent, in esterification process, the controllability of softening temperature is poor.
Summary of the invention
An object of the present invention is to make up the deficiencies in the prior art, provides a kind of preparation method controlling the ester gum of product softening temperature.
The technical scheme that the present invention realizes the employing of its object is:
A preparation method for ester gum, adopt rosin and glycerine reaction, it is characterized in that, reaction formula is as follows:
R is organic acid,
When needing the ester gum obtaining high softening-point, then the mol ratio of rosin and glycerine is 3: 1, and after the disposable input of rosin, glycerine is divided into 2 ~ 4 times and drops into reaction again;
When needing the ester gum of low softening point, then the mol ratio of rosin and glycerine is 1.5: 1 ~ 2.5: 1, and after the disposable input of glycerine, rosin is divided into 2 ~ 4 times and drops into reaction again.
A hydroxyl in glycerine, two hydroxyls, three hydroxyls are esterified, just generate monoglyceryl ester, two glyceryl ester, Witepsol W-S 55 respectively, in the esterification process of reality, regardless of the mol ratio of rosin and glycerine, monoglyceryl ester, two glyceryl ester and Witepsol W-S 55 all exist, and once, two, the number of Witepsol W-S 55 content determines the height of product softening temperature, so core of the present invention is by controlling esterification condition, control to generate one, two, Witepsol W-S 55 ratio, reach the object controlling product softening temperature.
When needs obtain low softening point rosin ester, can adopt disposable input glycerine, gradation drops into the technique of rosin, and more glycerine generates an ester, is conducive to like this obtaining low softening point finished product.If adopt low rosin glycerine ratio, the words of disposable input rosin often have transformation of glycerol partly and become diester and three esters, and partial glycerol no esterification, and steam with water, cause the loss of glycerine, and softening temperature declines not obvious.
When needs obtain high-softening-point rosin ester, adopt rosin: glycerine=3: 1, and glycerol batch drops into, such product overwhelming majority is three esters, can obtain the glyceryl ester that softening temperature is higher.
The beneficial effect that the present invention has:
The softening temperature of product ester gum is controlled, practicality is stronger, process is simple, formation efficiency is high, and this controls the method for esterified prod softening temperature, be also suitable for the esterification (product is rosin ethylene glycol ester) of rosin and ethylene glycol, the esterification (product is pentalyn) of rosin and tetramethylolmethane, benzene esterification process.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but protection scope of the present invention is not only confined to embodiment.
In following embodiment, raw material rosin softening temperature is 78 DEG C.
Embodiment 1:
In a four-hole boiling flask, add rosin 500g, glycerine 62.5g, calcium acetate 0.5g (rosin: mol ratio=2.4 of glycerine: 1), four-hole boiling flask has a bite to connect agitator, another mouth takes back flow condenser, with Electric heating bowl heating, react 4 hours under 250 DEG C of conditions, then 260 DEG C of reactions 2 hours, discharging, finished colophonium glyceryl ester softening temperature 84 DEG C.
Embodiment 2:
Adopt above-mentioned same sampling device and ratio, catalyzer is constant.Rosin first time drops into 250g, then reacts 2 hours under 250 DEG C of conditions, then drops into 250g, and 250 DEG C of reactions 2 hours, be warmed up to 260 DEG C of reactions 2 hours, discharging, the softening temperature of finished colophonium glyceryl ester was 82.5 DEG C.
Real examination example 3:
Identical with catalyzer with the device of embodiment 1, proportioning changes into rosin 500g, glycerine 50.7g, the constant (rosin: mol ratio=3 of glycerine: 1) of catalyzer, 500g rosin and the disposable input of catalyzer, glycerine first drops into 30g, 250 DEG C of reactions 2 hours, then drops into 20.7g glycerine, 250 DEG C are continued reaction 2 hours, be warmed up to 260 DEG C of reactions 2 hours again, discharging, finished product softening temperature is 87 DEG C.
Real examination example 4:
Identical with catalyzer with the device of embodiment 3, proportioning changes into rosin 500g, glycerine 50.7g, constant (the rosin: mol ratio=3 of glycerine: 1) of catalyzer, 500g rosin and the disposable input of catalyzer, 50.7g glycerine first dropped into by property again, 250 DEG C of reactions 4 hours, discharging, finished product softening temperature is 85 DEG C.
Embodiment 5:
Device similarly to Example 1 and catalyzer, rosin 500g, glycerine 72g, (rosin: mol ratio=2.1 of glycerine: 1).First drop into rosin 200g, glycerine 72g, catalyzer is whole, reacts 2 hours under 250 DEG C of conditions, drop into 200g rosin again, 250 DEG C are reacted 1 hour, then drop into residue 100g rosin, react 1 hour, then 260 DEG C are reacted two hours, and discharging, the softening temperature of finished colophonium glyceryl ester is 82.5 DEG C.
Real examination example 6:
Device similarly to Example 1 and catalyzer, rosin 500g, glycerine 51.4g, (rosin: mol ratio=1.5 of glycerine: 1).First drop into rosin 200g, glycerine 51.4g, catalyzer is whole, reacts 2 hours under 250 DEG C of conditions, drop into 200g rosin again, 250 DEG C are reacted 1 hour, then drop into residue 100g rosin, react 1 hour, then 260 DEG C are reacted two hours, and discharging, the softening temperature of finished colophonium glyceryl ester is 80 DEG C.
In sum, by controlling rosin and the esterification condition such as the mol ratio of glycerine and the feed postition of rosin and glycerine, control one of generation, two, Witepsol W-S 55 ratio, the object of control product ester gum softening temperature can be reached.
Last it is noted that above embodiment only in order to illustrate the present invention and and unrestricted technical scheme described in the invention; Therefore, although this specification sheets with reference to each above-mentioned embodiment to present invention has been detailed description, those of ordinary skill in the art should be appreciated that and still can modify to the present invention or equivalent to replace; And all do not depart from technical scheme and the improvement thereof of the spirit and scope of the present invention, it all should be encompassed in right of the present invention.
Claims (1)
1. a preparation method for ester gum, adopt rosin and glycerine reaction, it is characterized in that, reaction formula is as follows:
R is organic acid,
When needing the ester gum obtaining high softening-point, then the mol ratio of rosin and glycerine is 3: 1, and after the disposable input of rosin, glycerine is divided into 2 ~ 4 times and drops into reaction again;
When needing the ester gum of low softening point, then the mol ratio of rosin and glycerine is 1.5: 1 ~ 2.5: 1, and after the disposable input of glycerine, rosin is divided into 2 ~ 4 times and drops into reaction again.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410020296.3A CN104774560A (en) | 2014-01-09 | 2014-01-09 | Preparation method of rosin glycerin ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410020296.3A CN104774560A (en) | 2014-01-09 | 2014-01-09 | Preparation method of rosin glycerin ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104774560A true CN104774560A (en) | 2015-07-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410020296.3A Pending CN104774560A (en) | 2014-01-09 | 2014-01-09 | Preparation method of rosin glycerin ester |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105754485A (en) * | 2016-04-15 | 2016-07-13 | 梧州市飞卓林产品实业有限公司 | Rosin glycerin ester production method |
| CN106085243A (en) * | 2016-06-27 | 2016-11-09 | 梧州市嘉盈树胶有限公司 | The preparation method of pale rosin glyceride |
| CN116178696A (en) * | 2022-12-13 | 2023-05-30 | 山东一诺威新材料有限公司 | Rosin-based polyether polyol, and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4548746A (en) * | 1984-05-14 | 1985-10-22 | Westvaco Corporation | Rosin pentaerythritol ester preparation improvement |
| CN102617350A (en) * | 2012-02-28 | 2012-08-01 | 无锡信达胶脂材料有限公司 | Method for improving conversion rate of poly-glycerin rosin esters |
-
2014
- 2014-01-09 CN CN201410020296.3A patent/CN104774560A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4548746A (en) * | 1984-05-14 | 1985-10-22 | Westvaco Corporation | Rosin pentaerythritol ester preparation improvement |
| CN102617350A (en) * | 2012-02-28 | 2012-08-01 | 无锡信达胶脂材料有限公司 | Method for improving conversion rate of poly-glycerin rosin esters |
Non-Patent Citations (2)
| Title |
|---|
| 韦小杰等: "《氢化松香甘油酯的合成反应研究》", 《林产化工通讯》 * |
| 黄耀东等: "《固体酸催化合成聚合松香甘油酯》", 《广西化工》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105754485A (en) * | 2016-04-15 | 2016-07-13 | 梧州市飞卓林产品实业有限公司 | Rosin glycerin ester production method |
| CN105754485B (en) * | 2016-04-15 | 2018-07-31 | 梧州市飞卓林产品实业有限公司 | The production method of rosin glycerides |
| CN106085243A (en) * | 2016-06-27 | 2016-11-09 | 梧州市嘉盈树胶有限公司 | The preparation method of pale rosin glyceride |
| CN116178696A (en) * | 2022-12-13 | 2023-05-30 | 山东一诺威新材料有限公司 | Rosin-based polyether polyol, and preparation method and application thereof |
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