126-58-9

Basic information

• Product Name: Dipentaerythritol
• Synonyms: 2,2'[OXYBIS(METHYLEN)]BIS[HYDROXYMETHYL]-1,3-PROPANDIOL;2,2,6,6,-Tetra(hydroxymethyl)-4-oxaheptane-1,7-diol;2,2,2',2'-tetrakis(hydroxymethyl)-3,3'-oxydipropan-1-ol;2-([3-Hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl)-2-(hydroxymethyl)-1,3-propanediol;2,2'-(Oxybis(methylene))bis-((hydroxymethyl)-1,3-propanediol);2,2’-(oxybis(methylene))bis(2-(hydroxymethyl)-3-propanediol;2,2’-[oxybis(methylene)]bis[2-(hydroxymethyl)-3-propanediol;3-Propanediol,2,2’-[oxybis(methylene)]bis[2-(hydroxymethyl)-1
• CAS NO: 126-58-9
• Molecular Formula: C₁₀H₂₂O₇
• Molecular Weight: 254.28
• EINECS: 204-794-1
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Fine Chemical
• Mol File: 126-58-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 215-218 °C(lit.)
• Boiling Point: 356°C
• Flash Point: 282.1 °C
• Appearance: White/Crystalline Powder
• Density: 1.36 g/cm3 (20℃)
• Vapor Pressure: 4.77E-14mmHg at 25°C
• Refractive Index: 1.4455 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 2.4g/l
• PKA: 13.38±0.10(Predicted)
• Water Solubility: 0.29 g/100 mL (20 ºC)
• Sensitive: Hygroscopic
• CAS DataBase Reference: Dipentaerythritol(CAS DataBase Reference)
• NIST Chemistry Reference: Dipentaerythritol(126-58-9)
• EPA Substance Registry System: Dipentaerythritol(126-58-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 126-58-9(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

2,2''-(Oxybis(methylene))bis(2-(hydroxymethyl)-propane-1,3-diol) is used in preparation of new type of explosion-proof and flame-retardant tape material for cables.

Application

Dipentaerythritol (DPE) is an attractive raw material used for the production of polyesters, polyethers, polyurethanes, alkyd resins, photosensitive resin film. DPE is also employed in a wide range synthesis of specialty chemicals such as lubricants, coatings, adhesives, plasticizers and cosmetics.

Preparation

Dipentaerythritol is obtained as a byproduct in the manufacture of pentaerythritol; it is separated by fractional distillation. Dipentaerythritol (DPE) has been prepared from a slurry of Pentaerythritol (PE) in sulfolane catalyzed by a low amount of sulfuric acid and was isolated with 16% yield (72% GPC purity) and 57% isolated selectivity.synthesis of dipentaerythritol from pentaerythritol under acidic conditions

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H22O7/c11-1-9(2-12,3-13)7-17-8-10(4-14,5-15)6-16/h11-16H,1-8H2

Synthetic route

formaldehyd (50-00-0) + formic acid (64-18-6) + acetaldehyde (75-07-0) → Pentaerythritol (115-77-5) + Dipentaerythritol (126-58-9) + sodium formate (141-53-7)

Conditions	Yield
Stage #1: formaldehyd; acetaldehyde With sodium hydroxide at 45 - 65℃; under 1500.15 Torr; for 1.38333h; Inert atmosphere; Stage #2: formic acid pH=6; Product distribution / selectivity;	A 87.4% B 5% C 99.7%

2',2'':6',6''-di-O-benzylidene-2',2'',6',6''-tetra-(hydroxymethyl)-4-oxa-1,7-heptanediol (625092-16-2) → Dipentaerythritol (126-58-9)

Conditions	Yield
With water; acetic acid for 1.5h; Heating;	88%

Pentaerythritol (115-77-5) → Dipentaerythritol (126-58-9)

Conditions	Yield
With [1,3]-dioxolan-2-one; tetrabutoxytitanium; boron trioxide; sodium formate at 140 - 190℃; under 412.541 - 727.573 Torr; for 14h; Reagent/catalyst; Pressure; Temperature; Dean-Stark;	38%

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → Pentaerythritol (115-77-5) + Dipentaerythritol (126-58-9)

Conditions	Yield
With alkali Trennung ueber die Salpersaeureester;
With alkali Trennung von Pentaerythrit ueber die Salpetersaeureester;
With calcium hydroxide; water at 20℃;

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → Dipentaerythritol (126-58-9)

Conditions	Yield
With sodium hydroxide; Pentaerythritol; water at 58℃;

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → Pentaerythritol (115-77-5) + tri(hydroxymethyl)acetaldehyde (3818-32-4) + Dipentaerythritol (126-58-9) + tripentaerythritol (78-24-0) + 3-(3-Hydroxy-2,2-bis-hydroxymethyl-propoxy)-2,2-bis-hydroxymethyl-propionaldehyde + 3-[3-(3-Hydroxy-2,2-bis-hydroxymethyl-propoxy)-2,2-bis-hydroxymethyl-propoxy]-2,2-bis-hydroxymethyl-propionaldehyde

Conditions	Yield
With sodium hydroxide at 30℃; Product distribution; Mechanism; pH=12.5; different initial acetaldehyde concentrations;

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → Pentaerythritol (115-77-5) + acetaldol (107-89-1) + Dipentaerythritol (126-58-9)

Conditions	Yield
With sodium hydroxide at 10℃; for 5h; Product distribution; Mechanism; different initial aldehyde concentrations and reaction times; effect of additional pentaerythritol;

formaldehyd (50-00-0) + acetaldehyde (75-07-0) + Ca(OH)2 → Pentaerythritol (115-77-5) + Dipentaerythritol (126-58-9)

Conditions	Yield
je nach Bedingungen wechselnden Mengen;

formaldehyd (50-00-0) + acetaldehyde (75-07-0) + lime milk → Pentaerythritol (115-77-5) + Dipentaerythritol (126-58-9)

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → Pentaerythritol (115-77-5) + Formaldehyd-bis(pentaerythrityl)acetal (6228-26-8) + Dipentaerythritol (126-58-9) + various other products

Conditions	Yield
In water at 10℃; Rate constant; Mechanism; Product distribution; and equilibrium constants;

bis-(3-formyloxy-2,2-bis-formyloxymethyl-propyl)-ether → Dipentaerythritol (126-58-9) + carbon dioxide (124-38-9) + CO

Conditions	Yield
at 270℃; Thermolysis;

bis-(3-trityloxy-2,2-bis-trityloxymethyl-propyl)-ether + water (7732-18-5) → triphenylmethyl alcohol (76-84-6) + Dipentaerythritol (126-58-9)

Pentaerythritol (115-77-5) + acrolein (107-02-8) → Dipentaerythritol (126-58-9)

Conditions	Yield
With sodium hydroxide; formaldehyd; formic acid In water

Dipentaerythritol (126-58-9) + 3-mercaptopropionic acid (107-96-0) → dipentaerythritol hexakis(3-mercaptopropionate)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃; for 6h;	100%
With sulfuric acid In toluene for 48h; Heating / reflux;	58%
With SO42-/ Al2O3-ZrO2 at 80 - 100℃;	390.5 g

Dipentaerythritol (126-58-9) + cyclohexanone (108-94-1) → 2',2'':6',6''-di-O-cyclohexylidene-2',2'',6',6''-tetra(hydroxymethyl)-4-oxa-1,7-heptanediol

Conditions	Yield
With sulfuric acid at 80℃;	100%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 6h; Heating;	98%

Dipentaerythritol (126-58-9) + hexanoic acid (142-62-1) → dipentaerythritol hexahexanoate (19544-39-9)

Conditions	Yield
With sulfuric acid; toluene-4-sulfonic acid at 128℃; for 0.15h; Neat (no solvent); Microwave irradiation;	98%

2-(hydroxymethyl)-2-methylpropane-1,3-diol (77-85-0) + triethyl phosphate (78-40-0) + Dipentaerythritol (126-58-9) + triethyl phosphite (122-52-1) → C16H34O15P4

Conditions	Yield
Stage #1: 2-(hydroxymethyl)-2-methylpropane-1,3-diol; Dipentaerythritol; triethyl phosphite at 85℃; for 5h; Inert atmosphere; Stage #2: triethyl phosphate With Isobutyl bromide at 185℃; for 16h;	96.1%

Dipentaerythritol (126-58-9) + N,N-diethyl-α,α-difluorobenzylamine (90238-20-3) → 1-phenyl-4-{[(1-phenyl-2,6,7-trioxabicyclo[2.2.2]ocatne-4-yl)methoxy]methyl}-2,6,7-trioxabicyclo[2.2.2]octane (1097648-13-9)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 1h;	96%

oenanthic acid (111-14-8) + Dipentaerythritol (126-58-9) → dipentaerythritol hexaheptanoate (76939-66-7)

Conditions	Yield
With sulfuric acid; toluene-4-sulfonic acid at 135℃; for 0.183333h; Neat (no solvent); Microwave irradiation;	96%

1,1,1-tri(hydroxymethyl)propane (77-99-6) + Dipentaerythritol (126-58-9) + dimethyl methane phosphonate (756-79-6) + phosphorous acid trimethyl ester (121-45-9) → methyl-(5-ethyl-2-methyl-1,3,2-dioxaphosphorinan-5-yl)methyl methyl ester (P-oxide phosphonate)

Conditions	Yield
Stage #1: 1,1,1-tri(hydroxymethyl)propane; Dipentaerythritol; phosphorous acid trimethyl ester With phosphoric acid at 85℃; for 5h; Inert atmosphere; Stage #2: dimethyl methane phosphonate With 1-bromo-butane at 185℃; for 16h;	95.8%

trimethyl phosphite (512-56-1) + 1,1,1-tri(hydroxymethyl)propane (77-99-6) + tri-n-butyl phosphite (102-85-2) + Dipentaerythritol (126-58-9) → C13H25O10P3

Conditions	Yield
Stage #1: 1,1,1-tri(hydroxymethyl)propane; tri-n-butyl phosphite; Dipentaerythritol With sulfuric acid at 85℃; for 5h; Inert atmosphere; Stage #2: trimethyl phosphite With 1-Bromopentane at 185℃; for 16h;	95.6%

2-bromophenylacetic acid (4870-65-9) + Dipentaerythritol (126-58-9) → Bromo-phenyl-acetic acid 3-(2-bromo-2-phenyl-acetoxy)-2-[3-(2-bromo-2-phenyl-acetoxy)-2,2-bis-(2-bromo-2-phenyl-acetoxymethyl)-propoxymethyl]-2-(2-bromo-2-phenyl-acetoxymethyl)-propyl ester

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃; for 16h;	95%

Dipentaerythritol (126-58-9) + p-toluenesulfonyl chloride (98-59-9) → dipentaerythritol hexatosylate (214144-11-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Cooling with ice;	95%
With pyridine at 25℃; for 48h;	85%
With pyridine at 0 - 20℃;	68%

Octanoic acid (124-07-2) + Dipentaerythritol (126-58-9) → dipentaerythritol hexaoctanoate

Conditions	Yield
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride In dichloromethane at 20℃; for 6h;	94%
With sulfuric acid; toluene-4-sulfonic acid at 142℃; for 0.166667h; Neat (no solvent); Microwave irradiation;	90%

Dipentaerythritol (126-58-9) + sulfur trioxide trimethylamine complex (3162-58-1) → C10H22O25S6*6C3H9N

Conditions	Yield
With N,N-dimethyl-formamide In toluene at 80℃; for 0.833333h; Inert atmosphere;	93.8%

1-decanoic acid (334-48-5) + Dipentaerythritol (126-58-9) → dipentaerythritol hexacaprate

Conditions	Yield
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride In dichloromethane at 20℃; for 6h;	93%

Dipentaerythritol (126-58-9) + valeric acid (109-52-4) → dipentaerythritol hexapentanoate (76185-96-1)

Conditions	Yield
With sulfuric acid; toluene-4-sulfonic acid at 115℃; for 0.166667h; Neat (no solvent); Microwave irradiation;	92%

Dipentaerythritol (126-58-9) + 2-propynyl chloride (624-65-7) → 3-(3-(prop-2-yn-1-yloxy)-2-((3-(prop-2-yn-1-yloxy)-2,2-bis((prop-2-yn-1yloxy)methyl)propoxy)methyl)-2-((prop-2-yn-1-yloxy)methyl)propoxy)prop-1-yne

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; toluene at 0 - 20℃; for 5h;	91%

Dipentaerythritol (126-58-9) + acetic anhydride (108-24-7) → 1,2',2'',6',6'',7-hexa-O-acetyl-2',2'',6',6''-tetra-(hydroxymethyl)-4-oxa-heptanediol (67754-23-8)

Conditions	Yield
With pyridine at 20℃; for 12h;	90%
With sodium acetate

Dipentaerythritol (126-58-9) + benzaldehyde (100-52-7) → 2',2'':6',6''-di-O-benzylidene-2',2'',6',6''-tetra-(hydroxymethyl)-4-oxa-1,7-heptanediol (625092-16-2)

Conditions	Yield
With hydrogenchloride In dimethyl sulfoxide; N,N-dimethyl-formamide under 100 Torr; for 3h; Heating;	90%
With toluene-4-sulfonic acid; benzene Entfernen des entstehenden Wassers;

Dipentaerythritol (126-58-9) + cyanoacetic acid (372-09-8) → C28H28N6O13

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 140℃; for 4h;	90%
toluene-4-sulfonic acid In toluene at 140℃; for 3h;

Dipentaerythritol (126-58-9) + 2-diethylamino-5,5-dimethyl-1,3,2-dioxaphosphorinane (21458-75-3) → dipentaerythrite hexa-2,2-dimethyl-1,3-propylene phosphite (1011802-79-1)

Conditions	Yield
With pyridine In 1,4-dioxane at 90 - 100℃; for 2h;	87%

Dipentaerythritol (126-58-9) + 2-chloro-1,3,2-dioxaphosphinane (6362-89-6) → C28H52O19P6 (1011802-78-0)

Conditions	Yield
With pyridine In 1,4-dioxane	85%

Dipentaerythritol (126-58-9) + 3H3N*3H(1+)*MnMo6O18(OH)6(3-) + tetrabutylammomium bromide (1643-19-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2C10H19O7(3-)*3C16H36N(1+)*C3H7NO*MnMo6O18(3+)

Conditions	Yield
Stage #1: 3H3N*3H(1+)*MnMo6O18(OH)6(3-) In water at 100℃; for 12h; Reflux; Stage #2: Dipentaerythritol for 3h; Reflux; Stage #3: tetrabutylammomium bromide; N,N-dimethyl-formamide	84%

(tetrabutylammonium)5[H4P2W15V3O62] + Dipentaerythritol (126-58-9) → 10N(C4H9)4(1+)*2H(1+)*2P2V3W15O59(3-)*[(OCH2)3CCH2]2O(6-)=[N(C4H9)4]10H2[P2V3W15O59(OCH2)3CCH2]2O

Conditions	Yield
In acetonitrile (OCNHC(CH2OH)3)2 added to MeCN soln. of W complex; refluxed for 6 d in dark, soln. added dropwise to Et2O; ppt. isolated by filtration; dried overnight under vac.; elem. anal.;	83.8%

Dipentaerythritol (126-58-9) → bis-(3-chloro-2,2-bis-chloromethyl-propyl) ether (57690-45-6)

Conditions	Yield
With pyridine; thionyl chloride at 50 - 115℃; for 5h;	82%

Dipentaerythritol (126-58-9) + 2-chloro-5,5-dimethyl-[1,3,2]dioxaphosphinane (2428-06-0) → dipentaerythrite hexa-2,2-dimethyl-1,3-propylene phosphite (1011802-79-1)

Conditions	Yield
With pyridine In 1,4-dioxane	80%

Dipentaerythritol (126-58-9) + allyl bromide (106-95-6) → bis-(3-allyloxy-2,2-bis-allyloxymethyl-propyl)-ether (64340-67-6)

Conditions	Yield
Stage #1: Dipentaerythritol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere;	80%

Dipentaerythritol (126-58-9) + Perfluoro pentanoyl fluoride (375-62-2) → C25H19F27O10

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 55 - 80℃; for 5h; Further stages;	80%
With triethylamine In N,N-dimethyl-formamide at 55 - 80℃; for 5h; Temperature;
With triethylamine In N,N-dimethyl-formamide at 55 - 80℃; for 5h; Temperature;

2-bromoisobutyric acid bromide (20769-85-1) + Dipentaerythritol (126-58-9) → dipentaerythritol hexakis(2-bromoisobutyrate)

Conditions	Yield
With triethylamine In 1,4-dioxane at -18 - 20℃; for 21h; Inert atmosphere;	76%
With TEA In tetrahydrofuran
With triethylamine In dimethyl sulfoxide at 5 - 20℃; for 48h;	2.9 g
With triethylamine In dichloromethane at 0 - 30℃; for 52h;

formaldehyd (50-00-0) + Dipentaerythritol (126-58-9) → 2',2'':6',6''-di-O-methylidene-2',2'',6',6''-tetra(hydroxymethyl)-4-oxa-1,7-heptanediol (95260-40-5)

Conditions	Yield
With sulfuric acid In N,N-dimethyl-formamide; benzene at 80℃;	75%
With hydrogenchloride at 85℃; for 14h;	40.6%

Upstream product

• 50-00-0 formaldehyd 
• 75-07-0 acetaldehyde 
• 7732-18-5 water 
• 625092-16-2 2',2'':6',6''-di-O-benzylidene-2',2'',6',6''-tetra-(hydroxymethyl)-4-oxa-1,7-heptanediol 
• 64-18-6 formic acid 
• 2754-18-9 3,3-bis(hydroxymethyl)oxetane 
• 115-77-5 Pentaerythritol 
• 107-02-8 acrolein 

Downstream Products

• 625092-16-2 2',2'':6',6''-di-O-benzylidene-2',2'',6',6''-tetra-(hydroxymethyl)-4-oxa-1,7-heptanediol 
• 29570-58-9 dipentaerythritol hexaacrylate 
• 41203-81-0 methyl-(5-ethyl-2-methyl-1,3,2-dioxaphosphorinan-5-yl)methyl methyl ester (P-oxide phosphonate) 
• 19544-39-9 Dipentaerythrit-hexacapronat 
• 76939-66-7 dipentaerythritol hexaheptanoate 
• 33250-21-4 dipentaerythritol hexakis(mercaptoacetate) 
• 1097648-13-9 1-phenyl-4-{[(1-phenyl-2,6,7-trioxabicyclo[2.2.2]ocatne-4-yl)methoxy]methyl}-2,6,7-trioxabicyclo[2.2.2]octane 
• 7575-23-7 pentaerythritol tetrakis(3-mercaptopropionate) 
• 10193-99-4 3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate 

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The aim of this study was to investigate the acid catalysis of boron phosphate (BP) to model compound dipentaerythritol (DPER) which acted as char source during the thermal degradation and combustion. Various amounts of BP were added in DPER and then the thermal degradation and combustion behavi...detailed

Dipentaerythritol (cas 126-58-9) penta-/hexa-acrylate based-highly cross-linked hybrid monolithic column: Preparation and its applications for ultrahigh efficiency separation of proteins10/01/2019

In this study, multi-acrylate based dipentaerythritol penta-/hexa-acrylate (DPEPA) was exploited for fabrication of highly cross-linked hybrid monolithic column by copolymerization with polyhedral oligomeric silsesquioxane methacryl substituted (POSS-MA) via a “one-pot” method. The new DPEPA-P...detailed

Catalytic dehydration of pentaerythritol to Dipentaerythritol (cas 126-58-9) over heteropoly compounds09/27/2019

Synthesis of dipentaerythritol (DPE) by dehydration of pentaerythritol (PE) has been studied using heteropoly compounds and various solid acids. Heteropoly compounds such as H3PW12O40, H4SiW12O40 and their supported catalysts were found to be effective. The addition of water in the reactant supp...detailed

ArticleMicroencapsulated ammonium polyphosphate by polyurethane with segment of Dipentaerythritol (cas 126-58-9) and its application in flame retardant polypropylene☆09/25/2019

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In this work, an experimental study for the determination of the density of two dipentaerythritol esters, dipentaerythritol hexapentanoate (DiPEC5) and dipentaerythritol hexaheptanoate (DiPEC7) has been performed for temperatures ranging from 283.15 K to 398.15 K and pressures up to 70 MPa. The ...detailed

Relevant articles and documents

Synthesis of dipentaerythritol from pentaerythritol under acidic conditions

The direct synthesis of dipentaerythritol (DPE) from pentaerythritol (PE) was studied under acidic conditions. After optimization of the reaction parameters in a batch reactor, DPE was obtained with 50% selectivity when 50% PE was converted. This process, using PE in suspension in sulfolane (PE/sulfolane ratio = 2333 g/L) at 175 °C for 60 min, required a low amount of sulfuric acid (0.5 mol %). The optimized conditions were transposed to a 140 grams scale process. Finally, DPE was isolated with 16% yield (72% gas chromatography, GC purity) for 28% conversion of PE that corresponds to 57% DPE selectivity.

A method of manufacturing a polyhydric alcohol ether

[Problem] The purpose of the invention is to react pentaerythritol, trimethylolpropane, or another such polyhydric alcohol with a carbonic acid ester to obtain dipentaerythritol, ditrimethylolpropane, or another such polyhydric alcohol ether at a good yield. [Solution] A method for producing a polyhydric alcohol ether characterized by the joint use of the following catalyst A and catalyst B when reacting a polyhydric alcohol and a carbonic acid ester and producing a polyhydric alcohol ether of a structure in which the polyhydric alcohol is dehydrated and condensed between molecules. Catalyst A: one or more compounds selected from the group consisting of compounds containing an alkali metal, compounds containing an alkaline earth metal, amines or salts thereof or complexes thereof, and semicarbazides or salts thereof. Catalyst B: one or more compounds selected from the group consisting of compounds containing boron, compounds containing titanium, and compounds containing zirconium.

METHOD OF PREPARING PENTAERYTHRITOL

A method of preparing monopentaerythritol, dipentaerthritol, and sodium formate through high temperature condensation and cascade recrystallization is disclosed. The method lowers the energy consumption dramatically and improves the cost-effectiveness by carrying out the reaction in a non-low-temperature zone, and thereby avoiding the requirement for refrigeration. The method alleviates the difficulty of separation and improves the product quality by means of cascade separation process, and thereby avoiding the low purity from a single separation. In addition, the mother liquor obtained after each separation step is recycled to the previous step as the recycling liquor, which avoids discharging waste, increases the product yield and lowers raw materials consumption.