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molecular formula C16H22O4 B582219 Diisobutyl Phthalate-d4 CAS No. 358730-88-8

Diisobutyl Phthalate-d4

Cat. No. B582219
M. Wt: 282.372
InChI Key: MGWAVDBGNNKXQV-KDWZCNHSSA-N
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Patent
US05610244

Procedure details

Into a stirred reactor 28.4 g of MgCl2, 49.5 g of anhydrous ethanol, 10 ml of vaseline oil ROL OB/30, 100 ml of silicone oil having a viscosity of 350 cs were added. The mixture was heated at 120° C. until MgCl2 was dissolved. The hot reaction mixture was then transferred to a 1.5 l reactor equipped with a Ultra Turrax T-45 N stirrer, containing 150 cm3 of vaseline oil and 150 cm3 of silicone oil. The temperature was maintained at 120° C. whilst stirring for 3 minutes at 3000 RPM. The mixture was then discharged in a 2 liter stirred tank containing 1 l of anhydrous n-heptane cooled to 0° C. whilst stirring at a speed of 6 m/sec for about 20 minutes, maintaining the temperature at 0° C. The particles so obtained, after washing with n-hexane, were subjected to a thermal treatment in a nitrogen stream, at temperatures ranging from 50° to 150° C. until spherical particles were obtained having a residual alcohol content of about 35% by weight. 25 g of this product were charged into a stirred reactor containing 625 ml of TlCl4 at 0° C. and under stirring. The mixture was then heated to 100° C. for one hour and then left to cool. When the temperature of 40° C. was reached, diisobutyl phthalate was added in quantities such to give a molar ratio of magnesium to phthalate of 8. The mixture was heated to 100° C. for 2 hours under stirring and then the solid was left to settle. The hot liquid was removed by syphoning. Then 500 ml of TiCl4 was added and the mixture was heated to 120° C. for 1 hour whilst stirring. After settling, the hot liquid was removed by syphoning and the solid was washed with n-hexane.
[Compound]
Name
alcohol
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
product
Quantity
25 g
Type
reactant
Reaction Step Two
[Compound]
Name
TlCl4
Quantity
625 mL
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
1 L
Type
solvent
Reaction Step Five
Name
Quantity
28.4 g
Type
reactant
Reaction Step Six
Quantity
49.5 g
Type
reactant
Reaction Step Six
[Compound]
Name
vaseline oil
Quantity
10 mL
Type
reactant
Reaction Step Six
[Compound]
Name
silicone oil
Quantity
100 mL
Type
reactant
Reaction Step Six
[Compound]
Name
350
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
vaseline oil
Quantity
150 mL
Type
reactant
Reaction Step Eight
[Compound]
Name
silicone oil
Quantity
150 mL
Type
reactant
Reaction Step Eight

Identifiers

REACTION_CXSMILES
[Mg+2:1].[Cl-].[Cl-].C(O)C.[C:7]([O:22]CC(C)C)(=[O:21])[C:8]1[C:9](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:10]([O:12]CC(C)C)=[O:11]>CCCCCCC>[Mg:1].[C:7]([O-:22])(=[O:21])[C:8]1[C:9](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:10]([O-:12])=[O:11] |f:0.1.2|

Inputs

Step One
Name
alcohol
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Two
Name
product
Quantity
25 g
Type
reactant
Smiles
Step Three
Name
TlCl4
Quantity
625 mL
Type
reactant
Smiles
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C=1C(C(=O)OCC(C)C)=CC=CC1)(=O)OCC(C)C
Step Five
Name
Quantity
1 L
Type
solvent
Smiles
CCCCCCC
Step Six
Name
Quantity
28.4 g
Type
reactant
Smiles
[Mg+2].[Cl-].[Cl-]
Name
Quantity
49.5 g
Type
reactant
Smiles
C(C)O
Name
vaseline oil
Quantity
10 mL
Type
reactant
Smiles
Name
silicone oil
Quantity
100 mL
Type
reactant
Smiles
Name
350
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Seven
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[Mg+2].[Cl-].[Cl-]
Step Eight
Name
vaseline oil
Quantity
150 mL
Type
reactant
Smiles
Name
silicone oil
Quantity
150 mL
Type
reactant
Smiles

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
120 °C
Stirring
Type
CUSTOM
Details
whilst stirring for 3 minutes at 3000 RPM
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

DISSOLUTION
Type
DISSOLUTION
Details
was dissolved
CUSTOM
Type
CUSTOM
Details
The hot reaction mixture was then transferred to a 1.5 l reactor
CUSTOM
Type
CUSTOM
Details
equipped with a Ultra Turrax T-45 N stirrer
STIRRING
Type
STIRRING
Details
stirred tank
TEMPERATURE
Type
TEMPERATURE
Details
cooled to 0° C.
STIRRING
Type
STIRRING
Details
whilst stirring at a speed of 6 m/sec for about 20 minutes
Duration
20 min
TEMPERATURE
Type
TEMPERATURE
Details
maintaining the temperature at 0° C
CUSTOM
Type
CUSTOM
Details
The particles so obtained
WASH
Type
WASH
Details
after washing with n-hexane
CUSTOM
Type
CUSTOM
Details
ranging from 50° to 150° C. until spherical particles
CUSTOM
Type
CUSTOM
Details
were obtained
STIRRING
Type
STIRRING
Details
under stirring
TEMPERATURE
Type
TEMPERATURE
Details
The mixture was then heated to 100° C. for one hour
Duration
1 h
WAIT
Type
WAIT
Details
left
TEMPERATURE
Type
TEMPERATURE
Details
to cool
CUSTOM
Type
CUSTOM
Details
the temperature of 40° C.

Outcomes

Product
Details
Reaction Time
3 min
Name
Type
product
Smiles
[Mg]
Name
Type
product
Smiles
C(C=1C(C(=O)[O-])=CC=CC1)(=O)[O-]

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US05610244

Procedure details

Into a stirred reactor 28.4 g of MgCl2, 49.5 g of anhydrous ethanol, 10 ml of vaseline oil ROL OB/30, 100 ml of silicone oil having a viscosity of 350 cs were added. The mixture was heated at 120° C. until MgCl2 was dissolved. The hot reaction mixture was then transferred to a 1.5 l reactor equipped with a Ultra Turrax T-45 N stirrer, containing 150 cm3 of vaseline oil and 150 cm3 of silicone oil. The temperature was maintained at 120° C. whilst stirring for 3 minutes at 3000 RPM. The mixture was then discharged in a 2 liter stirred tank containing 1 l of anhydrous n-heptane cooled to 0° C. whilst stirring at a speed of 6 m/sec for about 20 minutes, maintaining the temperature at 0° C. The particles so obtained, after washing with n-hexane, were subjected to a thermal treatment in a nitrogen stream, at temperatures ranging from 50° to 150° C. until spherical particles were obtained having a residual alcohol content of about 35% by weight. 25 g of this product were charged into a stirred reactor containing 625 ml of TlCl4 at 0° C. and under stirring. The mixture was then heated to 100° C. for one hour and then left to cool. When the temperature of 40° C. was reached, diisobutyl phthalate was added in quantities such to give a molar ratio of magnesium to phthalate of 8. The mixture was heated to 100° C. for 2 hours under stirring and then the solid was left to settle. The hot liquid was removed by syphoning. Then 500 ml of TiCl4 was added and the mixture was heated to 120° C. for 1 hour whilst stirring. After settling, the hot liquid was removed by syphoning and the solid was washed with n-hexane.
[Compound]
Name
alcohol
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
product
Quantity
25 g
Type
reactant
Reaction Step Two
[Compound]
Name
TlCl4
Quantity
625 mL
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
1 L
Type
solvent
Reaction Step Five
Name
Quantity
28.4 g
Type
reactant
Reaction Step Six
Quantity
49.5 g
Type
reactant
Reaction Step Six
[Compound]
Name
vaseline oil
Quantity
10 mL
Type
reactant
Reaction Step Six
[Compound]
Name
silicone oil
Quantity
100 mL
Type
reactant
Reaction Step Six
[Compound]
Name
350
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
vaseline oil
Quantity
150 mL
Type
reactant
Reaction Step Eight
[Compound]
Name
silicone oil
Quantity
150 mL
Type
reactant
Reaction Step Eight

Identifiers

REACTION_CXSMILES
[Mg+2:1].[Cl-].[Cl-].C(O)C.[C:7]([O:22]CC(C)C)(=[O:21])[C:8]1[C:9](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:10]([O:12]CC(C)C)=[O:11]>CCCCCCC>[Mg:1].[C:7]([O-:22])(=[O:21])[C:8]1[C:9](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:10]([O-:12])=[O:11] |f:0.1.2|

Inputs

Step One
Name
alcohol
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Two
Name
product
Quantity
25 g
Type
reactant
Smiles
Step Three
Name
TlCl4
Quantity
625 mL
Type
reactant
Smiles
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C=1C(C(=O)OCC(C)C)=CC=CC1)(=O)OCC(C)C
Step Five
Name
Quantity
1 L
Type
solvent
Smiles
CCCCCCC
Step Six
Name
Quantity
28.4 g
Type
reactant
Smiles
[Mg+2].[Cl-].[Cl-]
Name
Quantity
49.5 g
Type
reactant
Smiles
C(C)O
Name
vaseline oil
Quantity
10 mL
Type
reactant
Smiles
Name
silicone oil
Quantity
100 mL
Type
reactant
Smiles
Name
350
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Seven
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[Mg+2].[Cl-].[Cl-]
Step Eight
Name
vaseline oil
Quantity
150 mL
Type
reactant
Smiles
Name
silicone oil
Quantity
150 mL
Type
reactant
Smiles

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
120 °C
Stirring
Type
CUSTOM
Details
whilst stirring for 3 minutes at 3000 RPM
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

DISSOLUTION
Type
DISSOLUTION
Details
was dissolved
CUSTOM
Type
CUSTOM
Details
The hot reaction mixture was then transferred to a 1.5 l reactor
CUSTOM
Type
CUSTOM
Details
equipped with a Ultra Turrax T-45 N stirrer
STIRRING
Type
STIRRING
Details
stirred tank
TEMPERATURE
Type
TEMPERATURE
Details
cooled to 0° C.
STIRRING
Type
STIRRING
Details
whilst stirring at a speed of 6 m/sec for about 20 minutes
Duration
20 min
TEMPERATURE
Type
TEMPERATURE
Details
maintaining the temperature at 0° C
CUSTOM
Type
CUSTOM
Details
The particles so obtained
WASH
Type
WASH
Details
after washing with n-hexane
CUSTOM
Type
CUSTOM
Details
ranging from 50° to 150° C. until spherical particles
CUSTOM
Type
CUSTOM
Details
were obtained
STIRRING
Type
STIRRING
Details
under stirring
TEMPERATURE
Type
TEMPERATURE
Details
The mixture was then heated to 100° C. for one hour
Duration
1 h
WAIT
Type
WAIT
Details
left
TEMPERATURE
Type
TEMPERATURE
Details
to cool
CUSTOM
Type
CUSTOM
Details
the temperature of 40° C.

Outcomes

Product
Details
Reaction Time
3 min
Name
Type
product
Smiles
[Mg]
Name
Type
product
Smiles
C(C=1C(C(=O)[O-])=CC=CC1)(=O)[O-]

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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