CN1169979A - Preparation method of glycerol triacetate - Google Patents
Preparation method of glycerol triacetate Download PDFInfo
- Publication number
- CN1169979A CN1169979A CN 96102341 CN96102341A CN1169979A CN 1169979 A CN1169979 A CN 1169979A CN 96102341 CN96102341 CN 96102341 CN 96102341 A CN96102341 A CN 96102341A CN 1169979 A CN1169979 A CN 1169979A
- Authority
- CN
- China
- Prior art keywords
- acetic acid
- reaction
- acetate
- sodium
- trichloropropane
- 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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- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 238000002360 preparation method Methods 0.000 title claims description 4
- 235000013773 glyceryl triacetate Nutrition 0.000 title abstract 4
- 229960002622 triacetin Drugs 0.000 title abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 113
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims abstract description 45
- 239000001632 sodium acetate Substances 0.000 claims abstract description 43
- 235000017281 sodium acetate Nutrition 0.000 claims abstract description 43
- 229960000583 acetic acid Drugs 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 14
- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 43
- 229960004249 sodium acetate Drugs 0.000 claims description 40
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 abstract description 11
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052719 titanium Inorganic materials 0.000 abstract description 6
- 239000010936 titanium Substances 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- 239000002131 composite material Substances 0.000 abstract description 3
- 239000013067 intermediate product Substances 0.000 abstract description 3
- 239000012429 reaction media Substances 0.000 abstract description 3
- 238000005260 corrosion Methods 0.000 abstract description 2
- 230000007797 corrosion Effects 0.000 abstract description 2
- 239000001087 glyceryl triacetate Substances 0.000 abstract 2
- GTFUGSXMTMYKRG-UHFFFAOYSA-N (2-acetyloxy-3-chloropropyl) acetate Chemical compound CC(=O)OCC(CCl)OC(C)=O GTFUGSXMTMYKRG-UHFFFAOYSA-N 0.000 abstract 1
- BVXPMFQVOWRQKD-UHFFFAOYSA-N 2,3-dichloropropyl acetate Chemical compound CC(=O)OCC(Cl)CCl BVXPMFQVOWRQKD-UHFFFAOYSA-N 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 230000009466 transformation Effects 0.000 description 8
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- -1 Dichlorodiphenyl Acetate Chemical compound 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- 229920001747 Cellulose diacetate Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- XYAUIVRRMJYYHR-UHFFFAOYSA-N acetic acid;propane-1,2,3-triol Chemical compound CC(O)=O.OCC(O)CO XYAUIVRRMJYYHR-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing glycerol triacetate. Trichloropropane and sodium acetate are used as raw materials, the trichloropropane and the sodium acetate react in a water-containing acetic acid or glacial acetic acid medium to generate triacetin, and an intermediate product 1, 2-dichloro-3-propanol acetate and 1-chloro-2, 3-propanediol diacetate are returned to a reaction system to be continuously reacted with the sodium acetate to generate the triacetin. Trichloropropane and acetic acid are recovered as a light component (mixture). Acetic acid (or trichloropropane) is added into the mixture according to the requirement of the ingredients, so that the energy and material loss caused by independently recovering trichloropropane and acetic acid can be avoided, and the acetic acid used as a reaction medium can be recycled for a long time. The reaction is carried out in a reaction kettle made of titanium (or composite titanium material) or a glass lining reaction kettle, so that the corrosion of reaction materials to reaction equipment is greatly reduced.
Description
The present invention relates to a kind of method for preparing glycerine triacetate, particularly relating to a kind of is raw material with trichloropropane and sodium-acetate, is the method that reaction medium prepares glycerine triacetate with water-containing acetic acid or Glacial acetic acid.
Glycerine triacetate is a kind of good solvent and softening agent, can be used for food, spices and printing and dyeing industry.Because the intermiscibility of its Dichlorodiphenyl Acetate Mierocrystalline cellulose, Nitrocellulose, ethyl cellulose is good, thereby be specially adapted to do the jelling agent of cigarette filter Cellulose diacetate.As everyone knows, be raw material with glycerine and acetic acid, be the classical way of preparation glycerine triacetate.But this method produces a large amount of water in building-up process, causes the glycerine triacetate yield to reduce, and is raw material with glycerine, because market shortages causes product cost higher.Deutsches Reichs-Patent DE3,545,583 to disclose a kind of be the method for the synthetic glycerine triacetate of raw material with trichloropropane and sodium-acetate.This method requires the water content of reaction system must be below 0.5%, otherwise the yield of glycerine triacetate sharply reduces, and in fact, in actually operating, this condition is difficult to reach, even if can, also to expend sizable energy, thereby reduce this method feasibility economically.Secondly, this method requires must be with Glacial acetic acid as reaction medium, because the Glacial acetic acid water in the absorbing environmental very easily, thereby must manage to stop contacting of Glacial acetic acid and air, this also gives accumulating and uses Glacial acetic acid to bring inconvenience.
The objective of the invention is to overcome the weak point that exists in the prior art, a kind of novel method for preparing glycerine triacetate is provided, prepare glycerine triacetate with method of the present invention, can improve the yield of glycerine triacetate, reduce production costs, and make the by-product of epoxy chloropropane device be able to reasonable utilization.
In order to achieve the above object, the technical solution used in the present invention is summarized as follows:
The trichloropropane, sodium-acetate, acetic acid (be not limited only to Glacial acetic acid, but to use Glacial acetic acid for well) and the aceticanhydride that in titanium material (or titanium composite material) reactor (or glassed steel reaction vessels), add metering, sealed reactor.After reacting certain hour at a certain temperature, reactant is emitted in the reactive system cooling, centrifugation goes out the by product sodium-chlor of reaction, then with mother liquor rectifying so that reclaim acetic acid, trichloropropane, 1,2-two chloro-3-propanol acetate ester and 1-chloro-2, ammediol two acetic acid vinegar (this mixture is called light constituent) carry out rectifying to the heavy constituent that are stored in the tower still, get final product the product glycerine triacetate.The light constituent mixture is analyzed, and required to replenish an amount of trichloropropane, acetic acid and aceticanhydride, this mixture can be recycled with reference to the reaction batching.
The molar ratio range of sodium-acetate of the present invention and glyceryl trichloride is 0.8: 1~1.5: 1, is advisable with 1.0: 1~1.4: 1, on this proportioning basis, then causes the transformation efficiency of sodium-acetate to reduce if increase the consumption of sodium-acetate; And reduce the consumption of sodium-acetate, though the transformation efficiency that can guarantee sodium-acetate near 100%, but the efficient of whole synthesizer reduces.The molar ratio range of acetic acid and sodium-acetate is 1.5: 1~4.5: 1, and is comparatively suitable with 1.5: 1~4.0: 1.The water content of complete reaction mixture should be controlled at below 10%, is controlled at below 5% better.The usage quantity of aceticanhydride can determine that every mol water is added aceticanhydride 0.99~1.76mol according to the water content of reaction mixture.Temperature of reaction remains in 160~290 ℃ of scopes, with 190~220 ℃ for well, the reaction times is 2~8 hours, with 3~6 hours for well.Reaction pressure is 0.58~2.0MPa, and is comparatively suitable with 0.58~0.75MPa, and under the lower situation of temperature of reaction, reaction pressure can be regulated by nitrogen.Reaction is isolated byproduct sodium chloride after finishing from reaction mass, filtrate is carried out rectifying, reclaim acetic acid, glyceryl trichloride and a spot of 1-chloro-2, the mixture of ammediol diacetate esters is left and taken synthetic use next time, and rectifying goes out the product glycerine triacetate then.
Characteristics of the present invention are:
1. the by-product trichloropropane that utilizes chloropropane-epoxy chloropropane device has changed the synthetic route of traditional glycerine-acetic acid (aceticanhydride) as raw material, has reduced production cost.
2. by adding an amount of aceticanhydride to remove the water in the reaction system in reaction system, can avoid reducing because of the yield of the too high glycerine triacetate that causes of raw material water content, compare with the Deutsches Reichs-Patent technology, product yield has improved tens percentage points.
3. trichloropropane, acetic acid and intermediate product are reclaimed together conserve energy.
4. the reaction intermediate Returning reacting system reacts again, with the yield of raising glycerine triacetate, and can avoid because of handling the intermediate product pollution on the environment.
5. can avoid reaction mass corrosion to equipment under reaction conditions with titanium (or composite titanium material) system conversion unit.
In order to describe technical characterstic of the present invention better, be described further below in conjunction with embodiment, but the present invention is not limited to following embodiment.
Embodiment 1
Proportioning raw materials:
Sodium-acetate: glyceryl trichloride=1.2: 1 (mol/mol)
Acetic acid: sodium-acetate=3: 1 (mol/mol)
In being furnished with the 1000ml reactor of magnetic agitation, add sodium-acetate 1.8mol, glyceryl trichloride 1.5mol, Glacial acetic acid 5.4mol.Learn that by analysis the water content of this mixture is 0.4%, therefore do not add aceticanhydride, sealed reactor stirs, in the cooling after 3 hours of reaction under 195 ℃ the temperature condition, reaction mixture.Collect acetic acid, glyceryl trichloride and 3-chloro-2, the mixture of ammediol diacetate esters and product glycerine triacetate by rectifying.The sodium-acetate transformation efficiency is 99.3%, and the yield of glycerine triacetate is 76.6% (in sodium-acetate), and purity is 99.2%.
Embodiment 2
Proportioning raw materials:
Sodium-acetate: glyceryl trichloride=1.2: 1 (mol/mol)
Acetic acid: sodium-acetate=3: 1 (mol/mol)
Get acetic acid, glyceryl trichloride and the 3-chloro-2 collected among the embodiment 1, the mixture of ammediol diacetate esters adds reactor, adds acetic acid 0.16mol after the calculating, and glyceryl trichloride 0.65mol adds sodium-acetate 1.8mol then to formula ratio.The water content of assaying reaction mixture is 2%, adds aceticanhydride 1.23mol.Reaction conditions is with embodiment 1.Reaction finishes the back and collects acetic acid and glyceryl trichloride 0.85mol and 3-chloro-2, and ammediol diacetate esters 0.04mol collects glycerine triacetate 0.437mol.Reaction result sodium-acetate transformation efficiency is 99.1%, and glycerine triacetate yield (in sodium-acetate) is 77.8%.
Embodiment 3
Proportioning raw materials:
Sodium-acetate: glyceryl trichloride=0.8: 1 (mol/mol)
Acetic acid: sodium-acetate=1.5: 1 (mol/mol)
Add Glacial acetic acid 3.0mol, glyceryl trichloride 2.5mol, sodium acetate, anhydrous 2.0mol.Assaying reaction mixture water content is 1.4%, adds aceticanhydride 0.55mol.Temperature of reaction is 210 ℃, and the reaction times is 2.5 hours.Reaction finishes the back and collects glycerine triacetate 0.509mol, and the sodium-acetate transformation efficiency is 99.6%, and glycerine triacetate yield (in sodium-acetate) is 76.3%.
Embodiment 4
Proportioning raw materials:
Sodium-acetate: glyceryl trichloride=1.5: 1 (mol/mol)
Acetic acid: sodium-acetate=4.0: 1 (mol/mol)
Get acetic acid, glyceryl trichloride and the 3-chloro-2 collected among the embodiment 2, the mixture of ammediol diacetate esters adds reactor, adds acetic acid 1.96mol and glyceryl trichloride 0.35mol after the calculating to formula ratio, adds sodium-acetate 1.80mol then.Assaying reaction mixture water content is 0.7%, adds aceticanhydride 0.29mol.210 ℃ of temperature of reaction, 2.5 hours reaction times.Reaction finishes the back and collects glycerine triacetate 0.43mol, and the sodium-acetate transformation efficiency is 99.0%, and glycerine triacetate yield (in sodium-acetate) is 71.7%.
Embodiment 5
Proportioning raw materials:
Sodium-acetate: glyceryl trichloride=1.2: 1 (mol/mol)
Acetic acid: sodium-acetate=4.5: 1
Get acetic acid, glyceryl trichloride and the 3-chloro-2 collected among the embodiment 2, the mixture of ammediol diacetate esters adds reactor, adds acetic acid 2.86mol and glyceryl trichloride 0.65mol after the calculating to formula ratio, adds sodium-acetate 1.80mol then.Assaying reaction mixture water content is 4.7%, therefore adds aceticanhydride 1.83mol.200 ℃ of temperature of reaction, the reaction times is 3.5 hours, and reaction finishes the back and collects glycerine triacetate 0.45mol, and the sodium-acetate transformation efficiency is 99.3%, and glycerine triacetate yield (in sodium-acetate) is 78.2%.
Embodiment 6
Proportioning raw materials:
Sodium-acetate: l, 2,3-trichloropropane=1.5: 1 (mol/mol)
Acetic acid: sodium-acetate=2.5: 1 (mol/mol)
Add Glacial acetic acid 4.5mol, glyceryl trichloride 1.2mol, sodium acetate, anhydrous 1.8mol.Assaying reaction mixture water content is 3.1%, adds aceticanhydride 1.0mol.Temperature of reaction is 185 ℃, and the reaction times is 5 hours.Reaction finishes the back and collects glycerine triacetate 0.47mol, and the sodium-acetate transformation efficiency is 99.5%, and glycerine triacetate yield (in sodium-acetate) is 78.1%.
Claims (5)
1, a kind of preparation method of glycerine triacetate, comprise that with trichloropropane and sodium-acetate be raw material, reaction generates glycerine triacetate in water-containing acetic acid or Glacial acetic acid medium, it is characterized in that adding an amount of aceticanhydride in reaction system, is lower than 0.5% with the water content of controlling reaction mixture.
2, method according to claim 1 is characterized in that the water content according to reaction mixture, whenever contains 1mol water and preferably adds aceticanhydride 0.99~1.76mol.
3, method according to claim 1, the batching mol ratio that it is characterized in that sodium-acetate and glyceryl trichloride is 0.8: 1~1.5: 1, and is comparatively suitable with 1.0: 1~1.4: 1.
4, method according to claim 1, the batching mol ratio that it is characterized in that acetic acid and sodium-acetate is 1.5: 1~4.5: 1, and is comparatively suitable with 1.5: 1~4.0: 1.
5, method according to claim 1 is characterized in that the reaction times is 2~8 hours, with 3~6 hours for well.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN96102341A CN1049425C (en) | 1996-07-09 | 1996-07-09 | Preparation method of glycerol triacetate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN96102341A CN1049425C (en) | 1996-07-09 | 1996-07-09 | Preparation method of glycerol triacetate |
Publications (2)
Publication Number | Publication Date |
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CN1169979A true CN1169979A (en) | 1998-01-14 |
CN1049425C CN1049425C (en) | 2000-02-16 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN96102341A Expired - Fee Related CN1049425C (en) | 1996-07-09 | 1996-07-09 | Preparation method of glycerol triacetate |
Country Status (1)
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CN (1) | CN1049425C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101450897B (en) * | 2007-11-28 | 2013-06-05 | 中国石油化工股份有限公司 | Method for producing triacetin |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3004660A1 (en) * | 1980-02-08 | 1981-08-13 | Henkel KGaA, 4000 Düsseldorf | METHOD FOR THE CONTINUOUS PRODUCTION OF TRIACETINE |
DE3545583A1 (en) * | 1985-12-21 | 1987-06-25 | Dow Chemical Gmbh | METHOD FOR PRODUCING ORGANIC ESTERS FROM HALOGEN CARBON COMPOUNDS |
CN1124244A (en) * | 1994-12-06 | 1996-06-12 | 上海申贝办公机械总公司 | Glycerol triacetate |
-
1996
- 1996-07-09 CN CN96102341A patent/CN1049425C/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101450897B (en) * | 2007-11-28 | 2013-06-05 | 中国石油化工股份有限公司 | Method for producing triacetin |
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Publication number | Publication date |
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CN1049425C (en) | 2000-02-16 |
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