CN104628711B - Preparation method of diglycerol diacetal - Google Patents

Preparation method of diglycerol diacetal Download PDF

Info

Publication number
CN104628711B
CN104628711B CN201510061941.0A CN201510061941A CN104628711B CN 104628711 B CN104628711 B CN 104628711B CN 201510061941 A CN201510061941 A CN 201510061941A CN 104628711 B CN104628711 B CN 104628711B
Authority
CN
China
Prior art keywords
glycerol
aldehyde
preparation
acetal
positive
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.)
Active
Application number
CN201510061941.0A
Other languages
Chinese (zh)
Other versions
CN104628711A (en
Inventor
董晋湘
李旭
徐红
汤琼
武兰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Taiyuan University of Technology
Original Assignee
Taiyuan University of Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Taiyuan University of Technology filed Critical Taiyuan University of Technology
Priority to CN201510061941.0A priority Critical patent/CN104628711B/en
Publication of CN104628711A publication Critical patent/CN104628711A/en
Application granted granted Critical
Publication of CN104628711B publication Critical patent/CN104628711B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

The invention discloses a preparation method of diglycerol diacetal, and belongs to the technical field of preparation of an acetal compound in organic chemistry. The method comprises the step of based on water as a solvent, catalyzing acetalation reaction of diglycerol and saturated aliphatic aldehyde with a carbon atom number of 8-16 with organic acid as a catalyst to prepare diglycerol diacetal. The product diglycerol diacetal has high yield which reaches more than 85%. The preparation method disclosed by the invention has the advantages of easy operation, low equipment corrosion, environment-friendly synthetic process, low energy consumption, small investment and convenient industrialization implementation.

Description

A kind of preparation method of two glycerol two acetal
Technical field
The present invention relates to a kind of preparation method of two glycerol two acetal, belong to organic synthesis field.
Background technology
During production of biodiesel, often the biodiesel of 10 tons of production just has about 1 ton of glycerin by-product, with The scale of the biodiesel energy as an alternative uses, and glycerin by-product overstock problem becomes increasingly conspicuous, and glycerol is given it up and can be caused The problems such as wasting of resources, environmental pollution, in order to realize sustainable development, with glycerol as plateform molecules, by selective oxidation, ether The method such as change, be esterified, being condensed, by-product glycerin is converted into the extensive concern that useful chemicals receive people.
Glycerol and aldehydes or ketones can occur acetalation or ketal reaction, and the glycerol production acetal of generation or glycerol ketals exist The aspects such as fuel additive, surfactant, lubricant, spice, disinfectant have important purposes.Two glycerol are that two molecules are sweet The polyhydric alcohol containing four hydroxyls that oil is obtained by etherificate, is one of oligomerization product of glycerol.Two glycerol are a kind of sticky Liquid, the physical property of itself imparts its excellent and extensive purposes, and it is in cosmetics, food emulsifying agent and polymer The aspects such as plasticizer all have application.
Two glycerol and aldehydes or ketones can also occur acetalation or ketal reaction synthesizing new, there is potential using value Material two glycerol two acetal or two glycerol two ketal.Acidic catalyst is described as to first in Japan Patent JP 09020772 Benzenesulfonic acid, Loprazolam, sulfuric acid catalysis two glycerol and carbonyl compound (aldehydes or ketones) have in benzene, toluene, hexamethylene, petroleum ether etc. Machine solvent is, under dicyandiamide solution, acetalation or ketal reaction synthetic product two glycerol two acetal or two glycerol two ketal occur, and Product is applied to surfactant and lubricating oil aspect.Satoh H et al. reports two glycerol and furfural (C5H4O2) organic Solvent DMF is solvent, and Amberlyst 15 strong-acid ion exchange resin is catalyst, organic solvent first Benzene is water entrainer, occurs acetalation to synthesize polymer monomer two furfurylidene two glycerol under reduced pressure (difurfurylidene diglycerol, yield is 70.9%) (Satoh H, Mineshima A, Nakamura T, et al.Thermo-reversible Diels–Alder polymerization ofdifurfurylidene diglycerol and bismaleimide[J]Reactive and FunctionalPolymers,2014,76,49-56).Above-mentioned reaction is all Carry out in organic solvent, but inevitably environment is worked the mischief using poisonous organic solvent.
Two glycerol and carbon number are 8～16 two glycerol two contracting that synthesized by acetalation of representative examples of saturated aliphatic aldehyde Aldehyde, has potential application as surfactant, lubricant etc., but few with regard to its green syt and application at present Have been reported that, main cause be the high viscosity of two glycerol and strongly hydrophilic so that its with hydrophobic carbon number be 8～16 full Immiscible with both aliphatic aldehydes it is difficult to react.
It is known that the acetalation of two glycerol and aldehyde is dehydration, the presence of water has to the balance of dehydration Detrimental effect, the water removing reaction generation in time can be so that reaction be carried out to the direction generating product.Although with Water can hinder the carrying out of dehydration for solvent, but has some dehydrations at present, such as esterification, etherificate etc., can be in water Middle realization reaction.
Content of the invention
The present invention is intended to provide a kind of preparation method of two glycerol two acetal, building-up process environmental protection, energy consumption is low, small investment.
The invention provides a kind of preparation method of two glycerol two acetal, with water as solvent, using organic acid as catalysis Agent, there is acetalation preparation two glycerol two acetal in the representative examples of saturated aliphatic aldehyde that catalysis two glycerol are 8～16 with carbon number.
Above-mentioned preparation method, comprises the following steps：(1) aldehyde is mixed in proportion with two glycerol, thing on the basis of aldehyde, adds As catalyst, with water as solvent, stirring is warming up to 70～150 DEG C to organic acid, reacts 2～24 hours；(2) after reaction terminates, Wash through ethyl acetate extraction, saturated sodium bicarbonate solution, anhydrous sodium sulfate drying, two glycerol two acetal product concentrated in vacuo.
In above-mentioned preparation method, the mol ratio of described aldehyde and two glycerol is 1：(0.5～10).
In above-mentioned preparation method, described aldehyde is 1 with the mol ratio of organic acid catalyst：(0.003～0.2).
In above-mentioned preparation method, described aldehyde is 1 with the mol ratio of aqueous solvent：(5～50).
In above-mentioned preparation method, described organic acid catalyst is p-methyl benzenesulfonic acid, ethyl phenenyl azochlorosulfonate acid, octyl benzene sulfonic acid or ten Any one in dialkyl benzene sulfonic acids.
In above-mentioned preparation method, described aldehyde be n-octaldehyde, n-nonyl aldehyde, n-capric aldehyde, n-undecylic aldehyde, positive lauric aldehyde, positive 13 Any one in aldehyde, positive Tetradecanal, positive 15 aldehyde, positive hexadecanoyl.
In above-mentioned preparation method, the yield of described product two glycerol two acetal is more than 85%.
Above-mentioned preparation method products therefrom two glycerol two acetal is：Have lower formula (I), (II), (III) shown three kinds with point The mixture of isomer structure：
Wherein R1、R2It is respectively hydrogen or C7～C15Saturated hydrocarbyl.
In above-mentioned preparation method, described acetalation equation is：
Representative examples of saturated aliphatic aldehyde and two glycerine reaction substrates are assembled by hydrophobic interaction with organic acid under water is for dicyandiamide solution Form microemulsion, microemulsion droplets constitute microreactor, its inner hydrophobic, and the hydrone exclusion that can generate reaction, thus have Carry out to the direction generating product beneficial to acetalation dehydration.
Beneficial effects of the present invention：
The present invention is that to be catalyzed two glycerol and carbon number by organic acid catalyst under green solvent aqueous systems be 8～16 Representative examples of saturated aliphatic aldehyde prepares two glycerol two acetal by acetalation, and product yield is high, up to more than 85%；The present invention has Simple to operate, equipment corrosion is little, building-up process environmental protection, energy consumption are low, small investment, the advantage being easy to industrializing implementation.
Specific embodiment
To further illustrate the present invention below by embodiment, but to be not limited to following examples.
Embodiment 1：
Add two glycerol in equipped with motor stirrer, water knockout drum, condensing tube, the three neck round bottom flask of nitrogen ingress pipe 8.31g, then presses positive lauric aldehyde：Two glycerol=1:0.5 (mol ratio, similarly hereinafter) adds positive lauric aldehyde 18.43g, according to positive 12 Aldehyde：DBSA=1:0.006 (mol ratio, similarly hereinafter) adds dodecylbenzene sulfonic acid catalyst 0.20g, according to positive ten Dialdehyde：Water=1:10 (mol ratio, similarly hereinafter) adds water 18.00g, and under nitrogen atmosphere, stirring is warming up to 120 DEG C, reacts 4 hours After be cooled to room temperature, gained reactant liquor through ethyl acetate extract, saturated sodium bicarbonate solution wash, anhydrous sodium sulfate drying, vacuum It is concentrated to give two glycerol two acetal product 22.08g, yield is 88.67%.
Infrared spectrum characterization is carried out to product：
FTIR (KBr, cm-1)：2924.8,2854.4,1466.8,1457.2,1436.9,1405.2,1377.9, 1339.1,1143.5,1125.9,1085.4,1044.9,962.1,721.6.
It is 498 that mass spectrum records molecular weight of product.
Embodiment 2
Add two glycerol in equipped with motor stirrer, water knockout drum, condensing tube, the three neck round bottom flask of nitrogen ingress pipe 8.31g, then presses positive lauric aldehyde：Two glycerol=1:The 1 positive lauric aldehyde 9.22g of addition, according to positive lauric aldehyde：DBSA =1:0.003 addition dodecylbenzene sulfonic acid catalyst 0.05g, according to positive lauric aldehyde：Water=1:5 addition water 9.00g, in nitrogen Under atmosphere, stirring is warming up to 130 DEG C, and reaction was cooled to room temperature after 2 hours, and gained reactant liquor extracts through ethyl acetate, saturated carbon Sour hydrogen sodium solution is washed, anhydrous sodium sulfate drying, two glycerol two acetal product 10.91g concentrated in vacuo, and yield is 87.63%.
Infrared spectrum characterization is carried out to product：
FTIR (KBr, cm-1)：2924.8,2854.4,1466.8,1457.2,1436.9,1405.2,1377.9, 1339.1,1143.5,1125.9,1085.4,1044.9,962.1,721.6.
It is 498 that mass spectrum records molecular weight of product.
Embodiment 3
Add two glycerol in equipped with motor stirrer, water knockout drum, condensing tube, the three neck round bottom flask of nitrogen ingress pipe 13.29g, then presses n-octaldehyde：Two glycerol=1:4 addition n-octaldehyde 2.56g, according to n-octaldehyde：P-methyl benzenesulfonic acid=1:0.05 Add Catalyzed by p-Toluenesulfonic Acid agent 0.17g, according to n-octaldehyde：Water=1:20 addition water 7.2g, under nitrogen atmosphere, stirring heats up To 70 DEG C, reaction was cooled to room temperature after 24 hours, and gained reactant liquor extracts through ethyl acetate, saturated sodium bicarbonate solution is washed, no Aqueous sodium persulfate is dried, two glycerol two acetal product 3.31g concentrated in vacuo, and yield is 85.75%.
Infrared spectrum characterization is carried out to product：
FTIR (KBr, cm-1)：2920.6,2858.4,1463.1,1446.8,1415.6,1398.7,1337.1, 1148.5,1121.8,1086.8,1046.3,962.7,727.1.
It is 386 that mass spectrum records molecular weight of product.
Embodiment 4
Add two glycerol in equipped with motor stirrer, water knockout drum, condensing tube, the three neck round bottom flask of nitrogen ingress pipe 24.93g, then presses n-nonyl aldehyde：Two glycerol=1:3 addition n-nonyl aldehyde 7.11g, according to n-nonyl aldehyde：DBSA=1: 0.008 addition dodecylbenzene sulfonic acid catalyst 0.13g, according to n-nonyl aldehyde：Water=1:25 addition water 22.50g, in nitrogen atmosphere Under, stirring is warming up to 90 DEG C, and reaction was cooled to room temperature after 10 hours, and gained reactant liquor extracts through ethyl acetate, unsaturated carbonate hydrogen Sodium solution is washed, anhydrous sodium sulfate drying, two glycerol two acetal product 9.12g concentrated in vacuo, and yield is 88.12%.
Infrared spectrum characterization is carried out to product：
FTIR (KBr, cm-1)：2922.8,2856.3,1464.7,1461.1,1427.8,1414.5,1397.9, 1335.2,1147.8,1126.9,1088.4,1045.1,960.4,725.6.
It is 414 that mass spectrum records molecular weight of product.
Embodiment 5
Add two glycerol in equipped with motor stirrer, water knockout drum, condensing tube, the three neck round bottom flask of nitrogen ingress pipe 16.62g, then presses n-capric aldehyde：Two glycerol=1:2 addition n-capric aldehyde 7.81g, according to n-capric aldehyde：Ethyl phenenyl azochlorosulfonate acid=1:0.1 adds Enter ethyl phenenyl azochlorosulfonate acid catalyst 0.93g, according to n-capric aldehyde：Water=1:10 addition water 9.00g, under nitrogen atmosphere, stirring heats up To 100 DEG C, reaction was cooled to room temperature after 12 hours, and gained reactant liquor extracts through ethyl acetate, saturated sodium bicarbonate solution is washed, no Aqueous sodium persulfate is dried, two glycerol two acetal product 9.57g concentrated in vacuo, and yield is 86.61%.
Infrared spectrum characterization is carried out to product：
FTIR (KBr, cm-1)：2921.7,2854.6,1464.5,1455.3,1436.9,1410.5,1368.9, 1335.1,1143.8,1127.9,1088.4,1054.5,958.1,726.6.
It is 442 that mass spectrum records molecular weight of product.
Embodiment 6
Add two glycerol in equipped with motor stirrer, water knockout drum, condensing tube, the three neck round bottom flask of nitrogen ingress pipe 33.23g, then presses n-undecylic aldehyde：Two glycerol=1:10 addition n-undecylic aldehyde 3.41g, according to n-undecylic aldehyde：Octyl benzene sulfonic acid= 1:0.2 addition octyl benzene sulfonic acid catalyst 1.09g, according to n-undecylic aldehyde：Water=1:50 addition water 18.00g, in nitrogen atmosphere Under, stirring is warming up to 110 DEG C, and reaction was cooled to room temperature after 8 hours, and gained reactant liquor extracts through ethyl acetate, unsaturated carbonate hydrogen Sodium solution is washed, anhydrous sodium sulfate drying, two glycerol two acetal product 4.06g concentrated in vacuo, and yield is 86.38%.
Infrared spectrum characterization is carried out to product：
FTIR (KBr, cm-1)：2923.5,2855.2,1467.3,1456.7,1435.6,1407.7,1378.5, 1340.1,1143.4,1127.9,1088.4,1054.9,962.1,724.2.
It is 470 that mass spectrum records molecular weight of product.
Embodiment 7
Add two glycerol in equipped with motor stirrer, water knockout drum, condensing tube, the three neck round bottom flask of nitrogen ingress pipe 26.59g, then presses positive tridecylic aldehyde：Two glycerol=1:The 8 positive tridecylic aldehyde 3.97g of addition, according to positive tridecylic aldehyde：P-methyl benzenesulfonic acid= 1:0.15 addition Catalyzed by p-Toluenesulfonic Acid agent 0.52g, according to positive tridecylic aldehyde：Water=1:15 addition water 5.40g, in nitrogen atmosphere Under, stirring is warming up to 150 DEG C, and reaction was cooled to room temperature after 7 hours, and gained reactant liquor extracts through ethyl acetate, unsaturated carbonate hydrogen Sodium solution is washed, anhydrous sodium sulfate drying, two glycerol two acetal product 4.49g concentrated in vacuo, and yield is 85.36%.
Infrared spectrum characterization is carried out to product：
FTIR (KBr, cm-1)：2924.9,2854.1,1467.2,1458.2,1437.3,1406.2,1377.5, 1338.8,1145.5,1126.5,1086.4,1045.3,963.2,722.8.
It is 526 that mass spectrum records molecular weight of product.
Embodiment 8
Add two glycerol in equipped with motor stirrer, water knockout drum, condensing tube, the three neck round bottom flask of nitrogen ingress pipe 4.99g, then presses positive Tetradecanal：Two glycerol=1:The 1.5 positive Tetradecanal 4.25g of addition, according to positive Tetradecanal：Octyl benzene sulfonic acid= 1:0.02 addition octyl benzene sulfonic acid catalyst 0.11g, according to positive Tetradecanal：Water=1:12 addition water 4.32g, in nitrogen atmosphere Under, stirring is warming up to 80 DEG C, and reaction was cooled to room temperature after 18 hours, and gained reactant liquor extracts through ethyl acetate, unsaturated carbonate hydrogen Sodium solution is washed, anhydrous sodium sulfate drying, two glycerol two acetal product 4.78g concentrated in vacuo, and yield is 86.28%.
Infrared spectrum characterization is carried out to product：
FTIR (KBr, cm-1)：2922.6,2853.5,1466.8,1456.5,1437.8,1410.5,1375.1, 1337.3,1145.3,1126.6,1088.3,1045.7,962.1,726.6.
It is 554 that mass spectrum records molecular weight of product.
Embodiment 9
Add two glycerol in equipped with motor stirrer, water knockout drum, condensing tube, the three neck round bottom flask of nitrogen ingress pipe 33.23g, then presses positive 15 aldehyde：Two glycerol=1:The 10 positive 15 aldehyde 4.53g of addition, according to positive 15 aldehyde：Ethyl phenenyl azochlorosulfonate acid= 1:0.12 addition ethyl phenenyl azochlorosulfonate acid catalyst 0.45g, according to positive 15 aldehyde：Water=1:40 addition water 14.40g, in nitrogen atmosphere Under, stirring is warming up to 140 DEG C, and reaction was cooled to room temperature after 15 hours, and gained reactant liquor extracts through ethyl acetate, unsaturated carbonate hydrogen Sodium solution is washed, anhydrous sodium sulfate drying, two glycerol two acetal product 5.01g concentrated in vacuo, and yield is 86.08%.
Infrared spectrum characterization is carried out to product：
FTIR (KBr, cm-1)：2927.5,2858.7,1476.8,1459.6,1437.4,1408.2,1379.7, 1344.2,1146.5,1125.8,1088.5,1054.8,965.5,728.7；
It is 582 that mass spectrum records molecular weight of product.
Embodiment 10
Add two glycerol in equipped with motor stirrer, water knockout drum, condensing tube, the three neck round bottom flask of nitrogen ingress pipe 16.62g, then presses positive hexadecanoyl：Two glycerol=1:The 5 positive hexadecanoyl 4.81g of addition, according to positive hexadecanoyl：Detergent alkylate sulphur Acid=1:0.08 addition dodecylbenzene sulfonic acid catalyst 0.52g, according to positive hexadecanoyl：Water=1:30 addition water 10.80g, Under nitrogen atmosphere, stirring is warming up to 150 DEG C, and reaction was cooled to room temperature after 6 hours, and gained reactant liquor extracts through ethyl acetate, satisfies With sodium bicarbonate solution wash, anhydrous sodium sulfate drying, two glycerol two acetal product 5.32g concentrated in vacuo, yield is 87.21%.
Infrared spectrum characterization is carried out to product：
FTIR (KBr, cm-1)：2927.6,2858.5,1478.8,1459.2,1438.8,1406.5,1381.1, 1342.3,1145.7,1127.6,1089.3,1056.7,966.1,727.6；
It is 610 that mass spectrum records molecular weight of product.

Claims (8)

1. a kind of preparation method of two glycerol two acetal it is characterised in that：With water as solvent, using organic acid as catalyst, It is catalyzed two glycerol, with the representative examples of saturated aliphatic aldehyde that carbon number is 8～16, acetalation preparation two glycerol two acetal can occur；
Comprise the following steps：
(1) aldehyde is mixed with two glycerol, thing on the basis of aldehyde, add organic acid as catalyst, with water as solvent, stirring heats up To 70～150 DEG C, react 2～24 hours；
(2) after reaction terminates, adopt be extracted with ethyl acetate, saturated sodium bicarbonate solution is washed, anhydrous sodium sulfate drying, concentrated in vacuo Obtain two glycerol two acetal product.
2. two glycerol two acetal according to claim 1 preparation method it is characterised in that：Described aldehyde is rubbed with two glycerol That ratio is 1：(0.5～10).
3. two glycerol two acetal according to claim 1 preparation method it is characterised in that：Described aldehyde is rubbed with organic acid That ratio is 1：(0.003～0.2).
4. two glycerol two acetal according to claim 1 preparation method it is characterised in that：Described aldehyde is rubbed with aqueous solvent That ratio is 1：(5～50).
5. two glycerol two acetal according to claim 1 preparation method it is characterised in that：Described organic acid catalyst is Any one in p-methyl benzenesulfonic acid, ethyl phenenyl azochlorosulfonate acid, octyl benzene sulfonic acid or DBSA.
6. two glycerol two acetal according to claim 1 preparation method it is characterised in that：Described aldehyde is n-octaldehyde, just Any one in aldehyde C-9, n-capric aldehyde, n-undecylic aldehyde, positive lauric aldehyde, positive tridecylic aldehyde, positive Tetradecanal, positive 15 aldehyde, positive hexadecanoyl.
7. two glycerol two acetal according to claim 1 preparation method it is characterised in that：Described two glycerol two acetal Yield is more than 85%.
8. two glycerol two acetal according to claim 1 preparation method it is characterised in that：Products therefrom two glycerol two contracts Aldehyde is：There is lower formula (I), (II), the mixture of (III) shown three kinds of isomerss structures：
Wherein R1、R2It is respectively hydrogen or C7～C15Saturated hydrocarbyl.
CN201510061941.0A 2015-02-05 2015-02-05 Preparation method of diglycerol diacetal Active CN104628711B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510061941.0A CN104628711B (en) 2015-02-05 2015-02-05 Preparation method of diglycerol diacetal

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510061941.0A CN104628711B (en) 2015-02-05 2015-02-05 Preparation method of diglycerol diacetal

Publications (2)

Publication Number Publication Date
CN104628711A CN104628711A (en) 2015-05-20
CN104628711B true CN104628711B (en) 2017-02-22

Family

ID=53208001

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201510061941.0A Active CN104628711B (en) 2015-02-05 2015-02-05 Preparation method of diglycerol diacetal

Country Status (1)

Country Link
CN (1) CN104628711B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106946840B (en) * 2017-04-11 2019-05-24 太原理工大学 Two glycerol monoacetals of one kind and its preparation method and application

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101896474A (en) * 2007-10-09 2010-11-24 希凯迪斯股份有限公司 Method of making ketals and acetals

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1246275C (en) * 2004-05-21 2006-03-22 清华大学 Reaction extraction process for extracting lower polybasic alcohol from thin aqueous solution
CN101525329A (en) * 2009-04-03 2009-09-09 武汉工程大学 Synthetic method of glycerin methylal

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101896474A (en) * 2007-10-09 2010-11-24 希凯迪斯股份有限公司 Method of making ketals and acetals

Also Published As

Publication number Publication date
CN104628711A (en) 2015-05-20

Similar Documents

Publication Publication Date Title
Amarasekara et al. Synthesis of levulinic acid–glycerol ketal–ester oligomers and structural characterization using NMR spectroscopy
Zhang et al. Highly efficient catalytic valorization of biomass-derived hexoses and furfuryl alcohol in the presence of polymer-based catalysts
CN106478514A (en) A kind of synthesis γ, the method for δ unsaturated ketone compound
CN102627748B (en) Preparation method of acidic ionic liquid resorcinol formaldehyde resin copolymer material
CN104628711B (en) Preparation method of diglycerol diacetal
CN103497105A (en) Method for preparing ethyl levulinate through ultralow acid catalysis tapioca starch
WO2023226181A1 (en) Method for preparing 2,5-furandicarboxylic acid by using furfural
CN104661998A (en) Method for producing compound containing bis(perfluoroalkylsulfonyl)methyl group and salt thereof, and solid electrolyte membrane produced using same
CN103193753B (en) Method for preparing xanthene amerantrone derivative via catalysis of acidic ionic liquid
CN101838256B (en) Method for synthesizing vinylethylene carbonate
CN102964319B (en) Preparation method of 5-hydroxymethylfurfural
CN104987496A (en) Method for removing acid value during polyester polyol synthesis process
Amarasekara et al. 1-(Alkylsulfonic)-3-methylimidazolium chloride Brönsted acidic ionic liquid catalyzed hydrogen peroxide oxidations of biomass derived furan aldehydes
CN103446944A (en) Non-ionic Gemini surface active agent, and preparation method thereof
CN109293609A (en) A kind of preparation method of 2,5- furandicarboxylic acid diester
CN104817479A (en) Preparation technology optimization method of biomass surfactant for oil displacement
CN102718638A (en) Industrial preparation method of high-yield cinnamaldehyde
CN105924414B (en) A kind of method that 5 hydroxymethyl furfural is produced by carbohydrate
CN103588622A (en) Method for synthesizing 2-methallyl alcohol through continuous hydrolysis reaction
CN106916063A (en) A kind of method that functionalized acidic ionic liquid catalysis prepares geranyl acetate
CN105061164A (en) Method for preparing triarylmethane compounds by utilizing catalysis of [ChCl][ZnCl2]2
CN106946840A (en) A kind of two glycerine monoacetals and its preparation method and application
CN110156581A (en) A kind of method of one step photocatalysis lignin depolymerization and amination synthesis nitrogenous aromatic compound
US20210363095A1 (en) Method capable of realizing preparation and in-situ separation of oligomeric ricinoleate
CN107602516B (en) Method for synthesizing delta-cyclopentanolide under catalysis of amino acid ionic liquid

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant