1,4-Dioxane-2,5-dione,3,6-dimethyl-, (3R,6R)- supplier

Name
D(+)-LACTIDE
EINECS
CAS No. 13076-17-0
Article Data11
CAS DataBase
Density 1.186 g/cm³
Solubility
Melting Point 96.5-97.5 °C
Formula C₆H₈O₄
Boiling Point 285.469 °C at 760 mmHg
Molecular Weight 144.127
Flash Point 150.578 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,4-Dioxane-2,5-dione,3,6-dimethyl-, (3R-cis)-;D,D-Dilactide;1,4-Dioxane-2,5-dione, 3,6-dimethyl-, (3R,5R)-;p-Dioxane-2,5-dione, 3,6-dimethyl-, D- (8CI);D-(+)-Lactide;D-Dilactide;D-Lactide;DD-lactide;
PSA 52.60000
LogP -0.13660

Synthetic route

: stannous lactate

: 13076-17-0
D-lactide

Conditions

Conditions	Yield
With 1-acetylthiosemicarbazide at 110 - 180℃; under 1 Torr; for 2h; Temperature; Reagent/catalyst; Pressure;	95.82%

: 338-69-2
D-Alanine

A: 10326-41-7
D-Lactic acid

B: 13076-17-0
D-lactide

Conditions

Conditions	Yield
With sulfuric acid; sodium nitrite In water at 0 - 20℃; stereoselective reaction;	A 58% B < 3 %Spectr.

: 10326-41-7
D-Lactic acid

: 13076-17-0
D-lactide

Conditions

Conditions	Yield
Stage #1: D-Lactic acid at 160℃; under 50 Torr; for 4h; Inert atmosphere; Industrial scale; Stage #2: With biogenic guanidine creatinine (CR) at 200℃; under 8 Torr; for 2h; Industrial scale;	46.8%

Reaxys ID: 11369848: Reaxys ID: 11369848

A: hexalactide

B: 859046-55-2
trilactide

C: C12H16O8

D: 859046-57-4
C15H20O10

E: C21H28O14

F: 13076-19-2
(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione

G: 4511-42-6
L,L-dilactide

H: 13076-17-0
D-lactide

Conditions

Conditions	Yield
at 60 - 400℃; for 0.566667h; Product distribution / selectivity; Pyrolysis;	A 4.51% B 3.26% C 5.59% D 6.02% E 1.88% F 18.28% G n/a H n/a

...Expand

Reaxys ID: 11369849: Reaxys ID: 11369849

A: hexalactide

B: 859046-55-2
trilactide

C: C12H16O8

D: 859046-57-4
C15H20O10

E: 13076-19-2
(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione

F: 4511-42-6
L,L-dilactide

G: 13076-17-0
D-lactide

Conditions

Conditions	Yield
at 60 - 400℃; for 0.566667h; Product distribution / selectivity; Pyrolysis;	A 0.46% B 0.5% C 1.65% D 0.75% E 12.17% F n/a G n/a

...Expand

Reaxys ID: 11369849: Reaxys ID: 11369849

A: 13076-19-2
(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione

B: 4511-42-6
L,L-dilactide

C: 13076-17-0
D-lactide

Conditions

Conditions	Yield
at 60 - 400℃; for 0.433333 - 0.566667h; Product distribution / selectivity; Pyrolysis;	A 6.08% B n/a C n/a

...Expand

Reaxys ID: 11369849: Reaxys ID: 11369849

A: C12H16O8

B: 859046-57-4
C15H20O10

C: 4511-42-6
L,L-dilactide

D: 13076-17-0
D-lactide

Conditions

Conditions	Yield
at 60 - 300℃; for 0.4h; Product distribution / selectivity; Pyrolysis;	A 0.28% B 0.2% C n/a D n/a

...Expand

poly(L-lactic acid): poly(L-lactic acid)

A: 849585-22-4
LACTIC ACID

B: 13076-19-2
(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione

C: 4511-42-6
L,L-dilactide

D: 13076-17-0
D-lactide

Conditions

Conditions	Yield
tin(II) octanoate at 210 - 230℃; under 22.5023 Torr; for 1 - 2h; Product distribution / selectivity;
zinc stearate at 210 - 230℃; under 22.5023 Torr; for 1 - 2h; Product distribution / selectivity;
tin(II) octanoate at 210 - 230℃; under 22.5023 Torr; for 1 - 2h; Product distribution / selectivity;

...Expand

Reaxys ID: 11363805: Reaxys ID: 11363805

A: 4511-42-6
L,L-dilactide

B: 13076-17-0
D-lactide

Conditions

Conditions	Yield
tin octanoate at 60 - 300℃; for 0.4h; Product distribution / selectivity; Pyrolysis;

Reaxys ID: 11369849: Reaxys ID: 11369849

A: 4511-42-6
L,L-dilactide

B: 13076-17-0
D-lactide

Conditions

Conditions	Yield
at 60 - 320℃; for 0.433333h; Product distribution / selectivity; Pyrolysis;

: 13076-19-2
(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione

A: 4511-42-6
L,L-dilactide

B: 13076-17-0
D-lactide

Conditions

Conditions	Yield
Na-ethylhexanoate at 160℃; for 15h; Product distribution / selectivity; Racemisation; Parr reactor;
Multi-step reaction with 2 steps 1: potassium phosphate / ethyl acetate / 168 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 4 h / 110 °C View Scheme

: 79-33-4
L-Lactic acid

A: 13076-19-2
(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione

B: 4511-42-6
L,L-dilactide

C: 13076-17-0
D-lactide

Conditions

Conditions	Yield
Stage #1: L-Lactic acid In water at 170℃; under 80 Torr; for 3h; Stage #2: tin catalyst at 220℃; under 10 - 15 Torr; Product distribution / selectivity;
With potassium hydroxide; stannous octoate at 150 - 240℃; under 7.50075 Torr; Product distribution / selectivity;

...Expand

: 13076-19-2
(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione

: 13076-17-0
D-lactide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium phosphate / ethyl acetate / 168 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 4 h / 110 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 48 h / 20 °C View Scheme

: 3,6-dimethyl-1,4-dioxane-2,5-dione

A: 13076-19-2
(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione

B: 4511-42-6
L,L-dilactide

C: 13076-17-0
D-lactide

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; for 4h; optical yield given as %ee;

...Expand

: 4511-42-6
L,L-dilactide

A: 13076-19-2
(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione

B: 13076-17-0
D-lactide

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 48h;
With sodium hydride In mineral oil at 200℃; for 6h; Reagent/catalyst; Temperature; stereoselective reaction;

: 13076-19-2
(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione

: 4511-42-6
L,L-dilactide

: 13076-17-0
D-lactide

Conditions

Conditions	Yield
With sodium nitrite at 180℃; for 2h; Reagent/catalyst; Temperature; stereoselective reaction;

: 502-44-3
hexahydro-2H-oxepin-2-one

: 502-97-6
glycolide

: 13076-17-0
D-lactide

polymer, Mn: 48.0 kDa, Mw/Mn: 1.3; monomer(s): L-lactide; ε-caprolactone; glycolide: polymer, Mn: 48.0 kDa, Mw/Mn: 1.3; monomer(s): L-lactide; ε-caprolactone; glycolide

Conditions

Conditions	Yield
With zirconium acetylacetonate at 100℃;	92%

...Expand

: 109-89-7
diethylamine

: 13076-17-0
D-lactide

: (R)-N,N-diethyl-2-hydroxypropanamide

Conditions

Conditions	Yield
Stage #1: diethylamine With aluminum (III) chloride In dichloromethane at 35℃; for 0.5h; Stage #2: D-lactide In dichloromethane at 35℃; for 1h;	82%

: 71-23-8
propan-1-ol

: 13076-17-0
D-lactide

: (2R)-2-hydroxypropanoic acid, 2-propyloxy-(1R)-1-methyl-2-oxoethylester

Conditions

Conditions	Yield
With Pseudomonas fluorescens GK13 medium-chain-length-PHA depolymerase In toluene at 80℃; for 24h; Inert atmosphere; Enzymatic reaction;	80%

: 64-17-5
ethanol

: 13076-17-0
D-lactide

: 7699-00-5
(R)-Ethyl lactate

Conditions

Conditions	Yield
With hydrogenchloride In toluene	76%

: 13076-17-0
D-lactide

polylactide, Mn(GPC) = 13500, Mw/Mn(GPC) = 1.08, isotactic, monomer(s): D-lactide: polylactide, Mn(GPC) = 13500, Mw/Mn(GPC) = 1.08, isotactic, monomer(s): D-lactide

Conditions

Conditions	Yield
With tris(methylene)amine[tris(4,6-di-tBu-phenolate)]-(OiPrZr) In chloroform-d1 at 20℃; Kinetics;	75%

: 13076-17-0
D-lactide

poly-ε-caprolactone: poly-ε-caprolactone

poly(D-lactide-b-ε-caprolactone) diblock copolymer; monomers: D-lactide; poly(ε-caprolactone): poly(D-lactide-b-ε-caprolactone) diblock copolymer; monomers: D-lactide; poly(ε-caprolactone)

: 13076-17-0
D-lactide

poly-(D-lactide), isotactic, spectroscopic Mn=6400, chromatographic Mn=5900, Mw/Mn=1.08; monomer(s): D-lactide: poly-(D-lactide), isotactic, spectroscopic Mn=6400, chromatographic Mn=5900, Mw/Mn=1.08; monomer(s): D-lactide

Conditions

Conditions	Yield
With (R,R)-cyclohexylsalen aluminum isopropoxide In toluene at 70℃; Kinetics;

: 13076-17-0
D-lactide

L-lactide polymer: L-lactide polymer

Conditions

Conditions	Yield
With [C(Htbpoa)2Mg] In toluene at 20℃; for 0.25h;	100 % Turnov.

: 13076-17-0
D-lactide

poly(D-lactide), MW 1.45E4 g/mol; monomer(s): D-lactide: poly(D-lactide), MW 1.45E4 g/mol; monomer(s): D-lactide

Conditions

Conditions	Yield
In toluene

poly(ethylene glycol) 4600: poly(ethylene glycol) 4600

: 13076-17-0
D-lactide

polymer(D-lactide)-block-poly(ethylene glycol), Mn 6400 Da by NMR: polymer(D-lactide)-block-poly(ethylene glycol), Mn 6400 Da by NMR

Conditions

Conditions	Yield
zinc at 140℃; for 168h;

poly(ethylene glycol) 4600: poly(ethylene glycol) 4600

: 13076-17-0
D-lactide

poly(D-lactide)-block-poly(ethylene glycol), Mn 7700 Da by NMR: poly(D-lactide)-block-poly(ethylene glycol), Mn 7700 Da by NMR

Conditions

Conditions	Yield
zinc at 140℃; for 168h;

poly(ethylene glycol) 12000: poly(ethylene glycol) 12000

: 13076-17-0
D-lactide

poly(D-lactide)-block-poly(ethylene glycol), Mn 14700 Da by NMR: poly(D-lactide)-block-poly(ethylene glycol), Mn 14700 Da by NMR

Conditions

Conditions	Yield
zinc at 140℃; for 168h;

: 13076-17-0
D-lactide

polyethylene glycol 20000: polyethylene glycol 20000

poly(D-lactide)-block-poly(ethylene glycol), Mn 23100 Da by NMR: poly(D-lactide)-block-poly(ethylene glycol), Mn 23100 Da by NMR

Conditions

Conditions	Yield
zinc at 140℃; for 168h;

: 13076-17-0
D-lactide

polyethylene glycol 20000: polyethylene glycol 20000

poly(D-lactide)-block-poly(ethylene glycol), Mn 26700 Da by NMR: poly(D-lactide)-block-poly(ethylene glycol), Mn 26700 Da by NMR

Conditions

Conditions	Yield
zinc at 140℃; for 168h;

: 13076-17-0
D-lactide

Polyethylene glycol 10000: Polyethylene glycol 10000

poly(D-lactide)-block-poly(ethylene glycol), Mn 13700 Da by NMR: poly(D-lactide)-block-poly(ethylene glycol), Mn 13700 Da by NMR

Conditions

Conditions	Yield
zinc at 140℃; for 168h;

: 13076-17-0
D-lactide

poly(ethylene glycol) 8000: poly(ethylene glycol) 8000

poly(D-lactide)-block-poly(ethylene glycol), Mn 11000 Da by NMR: poly(D-lactide)-block-poly(ethylene glycol), Mn 11000 Da by NMR

Conditions

Conditions	Yield
zinc at 140℃; for 168h;

: 13076-17-0
D-lactide

monomethoxypolyethylene glycol 5000: monomethoxypolyethylene glycol 5000

poly(D-lactide)-block-monomethoxypoly(ethylene glycol), Mn 6900 Da by NMR: poly(D-lactide)-block-monomethoxypoly(ethylene glycol), Mn 6900 Da by NMR

Conditions

Conditions	Yield
zinc at 140℃; for 168h;

: 13076-17-0
D-lactide

monomethoxypolyethylene glycol 5000: monomethoxypolyethylene glycol 5000

poly(D-lactide)-block-monomethoxypoly(ethylene glycol), Mn 8700 Da by NMR: poly(D-lactide)-block-monomethoxypoly(ethylene glycol), Mn 8700 Da by NMR

Conditions

Conditions	Yield
zinc at 140℃; for 168h;

: 4511-42-6
L,L-dilactide

: 13076-17-0
D-lactide

poly(L-lactide-b-D-lactide), DP: 52 (by 1H NMR), Mn: 7800 (by GPC), Mw/Mn: 1.07; monomer(s): L-lactide, 80 mol percent; D-lactide, 20 mol percent: poly(L-lactide-b-D-lactide), DP: 52 (by 1H NMR), Mn: 7800 (by GPC), Mw/Mn: 1.07; monomer(s): L-lactide, 80 mol percent; D-lactide, 20 mol percent

Conditions

Conditions	Yield
Stage #1: L,L-dilactide With calcium bis{bis(trimethylsilyl)amide} In isopropyl alcohol Stage #2: D-lactide In isopropyl alcohol

: 4511-42-6
L,L-dilactide

: 13076-17-0
D-lactide

poly(L-lactide-b-D-lactide), DP: 49 (by 1H NMR), Mn: 7400 (by GPC), Mw/Mn: 1.05; monomer(s): L-lactide, 66 mol percent; D-lactide, 33 mol percent: poly(L-lactide-b-D-lactide), DP: 49 (by 1H NMR), Mn: 7400 (by GPC), Mw/Mn: 1.05; monomer(s): L-lactide, 66 mol percent; D-lactide, 33 mol percent

Conditions

Conditions	Yield
Stage #1: L,L-dilactide With calcium bis{bis(trimethylsilyl)amide} In isopropyl alcohol Stage #2: D-lactide In isopropyl alcohol

1,4-Dioxane-2,5-dione,3,6-dimethyl-, (3R,6R)- Specification

The 1,4-Dioxane-2,5-dione,3,6-dimethyl-, (3R,6R)-, with CAS registry number 13076-17-0, has the systematic name of (3R,6R)-3,6-dimethyl-1,4-dioxane-2,5-dione. Besides this, it is also called 3β,6β-Dimethyl-1,4-dioxin-2,5(3H,6H)-dione. Its classification code is TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]. And the chemical formula of this chemical is C₆H₈O₄.

Physical properties of 1,4-Dioxane-2,5-dione,3,6-dimethyl-, (3R,6R)-: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 4.003; (5)ACD/KOC (pH 7.4): 4.003; (6)#H bond acceptors: 4; (7)#H bond donors: 0; (8)#Freely Rotating Bonds: 0; (9)Polar Surface Area: 52.6 Å²; (10)Index of Refraction: 1.429; (11)Molar Refractivity: 31.335 cm³; (12)Molar Volume: 121.519 cm³; (13)Polarizability: 12.422×10^-24cm³; (14)Surface Tension: 31.383 dyne/cm; (15)Density: 1.186 g/cm³; (16)Flash Point: 150.578 °C; (17)Enthalpy of Vaporization: 52.452 kJ/mol; (18)Boiling Point: 285.469 °C at 760 mmHg; (19)Vapour Pressure: 0.003 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: C[C@@H]1C(=O)O[C@@H](C(=O)O1)C
(2)InChI: InChI=1/C6H8O4/c1-3-5(7)10-4(2)6(8)9-3/h3-4H,1-2H3/t3-,4-/m1/s1
(3)InChIKey: JJTUDXZGHPGLLC-QWWZWVQMBS
(4)Std. InChI: InChI=1S/C6H8O4/c1-3-5(7)10-4(2)6(8)9-3/h3-4H,1-2H3/t3-,4-/m1/s1
(5)Std. InChIKey: JJTUDXZGHPGLLC-QWWZWVQMSA-N

Product Name

D(+)-LACTIDE

Synthetic route

1,4-Dioxane-2,5-dione,3,6-dimethyl-, (3R,6R)- Specification

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