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molecular formula C7H10O3 B7887341 [(2R)-oxiran-2-yl]methyl 2-methylprop-2-enoate

[(2R)-oxiran-2-yl]methyl 2-methylprop-2-enoate

Cat. No. B7887341
M. Wt: 142.15 g/mol
InChI Key: VOZRXNHHFUQHIL-ZCFIWIBFSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US05245057

Procedure details

A feed with 3-chloro-2-hydroxypropyl methacrylate (CHPMA), epichlorohydrln, and minor amounts of by-products (GMA and heavies such as polymer by-product materials) flows into an epoxidation reactor to which aqueous alkali metal hydroxides such as sodium hydroxide (NaOH) or potassium hydroxide (KOH) and additional epichlorohydrin are added. KOH reacts with CHPMA to form glycidyl methacrylate to (GMA), water, and potassium chloride (KCl). Sodium hydroxide may be used in place of KOH, but a higher GMA yield is obtained using KOH. Preferable reaction conditions are: starting molar epichlorohydrin/CHPMA ratio of 6.0 or higher (most preferably 9.0), molar KOH/CHPMA ratio of 0.8-1.5 (most preferably 1.1, temperature of 40-80 degrees centigrade (most preferably 60-65 degrees Centigrade), and a pressure of less than atmospheric (typically 150-200 mm Hg absolute). Preferably, KOH is added as a 40-60 weight per cent solution in water. A vapor stream removed from the epoxidation reactor is fractionated and the overhead epichlorohydrin/water stream is condensed and allowed to separate into two liquid phases. The heavier (organic) phase is returned to the fractionation tower as reflux and from the bottom of the fractionation tower to the epoxidation reactor. (See FIG. 7 and previous description thereof). The aqueous phase is sent forward in the process in the same manner as previously described for the epoxy process to serve as wash water which removes the last traces of KCl from the GMA product before the epichlorohydrin is stripped and the product recovered.
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
alkali metal hydroxides
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[C:1]([O:6][CH2:7][CH:8]([OH:11])[CH2:9][Cl:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH-].[Na+].[OH-].[K+:15].C(C1OC1)Cl>O>[C:1]([O:6][CH2:7][CH:8]1[O:11][CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[Cl-:10].[K+:15] |f:1.2,3.4,8.9|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(=C)C)(=O)OCC(CCl)O
Name
alkali metal hydroxides
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(Cl)C1CO1
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(=C)C)(=O)OCC(CCl)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
are added

Outcomes

Product
Name
Type
product
Smiles
C(C(=C)C)(=O)OCC1CO1
Name
Type
product
Smiles
[Cl-].[K+]

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
US05245057

Procedure details

A feed with 3-chloro-2-hydroxypropyl methacrylate (CHPMA), epichlorohydrln, and minor amounts of by-products (GMA and heavies such as polymer by-product materials) flows into an epoxidation reactor to which aqueous alkali metal hydroxides such as sodium hydroxide (NaOH) or potassium hydroxide (KOH) and additional epichlorohydrin are added. KOH reacts with CHPMA to form glycidyl methacrylate to (GMA), water, and potassium chloride (KCl). Sodium hydroxide may be used in place of KOH, but a higher GMA yield is obtained using KOH. Preferable reaction conditions are: starting molar epichlorohydrin/CHPMA ratio of 6.0 or higher (most preferably 9.0), molar KOH/CHPMA ratio of 0.8-1.5 (most preferably 1.1, temperature of 40-80 degrees centigrade (most preferably 60-65 degrees Centigrade), and a pressure of less than atmospheric (typically 150-200 mm Hg absolute). Preferably, KOH is added as a 40-60 weight per cent solution in water. A vapor stream removed from the epoxidation reactor is fractionated and the overhead epichlorohydrin/water stream is condensed and allowed to separate into two liquid phases. The heavier (organic) phase is returned to the fractionation tower as reflux and from the bottom of the fractionation tower to the epoxidation reactor. (See FIG. 7 and previous description thereof). The aqueous phase is sent forward in the process in the same manner as previously described for the epoxy process to serve as wash water which removes the last traces of KCl from the GMA product before the epichlorohydrin is stripped and the product recovered.
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
alkali metal hydroxides
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[C:1]([O:6][CH2:7][CH:8]([OH:11])[CH2:9][Cl:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH-].[Na+].[OH-].[K+:15].C(C1OC1)Cl>O>[C:1]([O:6][CH2:7][CH:8]1[O:11][CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[Cl-:10].[K+:15] |f:1.2,3.4,8.9|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(=C)C)(=O)OCC(CCl)O
Name
alkali metal hydroxides
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(Cl)C1CO1
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(=C)C)(=O)OCC(CCl)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
are added

Outcomes

Product
Name
Type
product
Smiles
C(C(=C)C)(=O)OCC1CO1
Name
Type
product
Smiles
[Cl-].[K+]

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
US05245057

Procedure details

A feed with 3-chloro-2-hydroxypropyl methacrylate (CHPMA), epichlorohydrln, and minor amounts of by-products (GMA and heavies such as polymer by-product materials) flows into an epoxidation reactor to which aqueous alkali metal hydroxides such as sodium hydroxide (NaOH) or potassium hydroxide (KOH) and additional epichlorohydrin are added. KOH reacts with CHPMA to form glycidyl methacrylate to (GMA), water, and potassium chloride (KCl). Sodium hydroxide may be used in place of KOH, but a higher GMA yield is obtained using KOH. Preferable reaction conditions are: starting molar epichlorohydrin/CHPMA ratio of 6.0 or higher (most preferably 9.0), molar KOH/CHPMA ratio of 0.8-1.5 (most preferably 1.1, temperature of 40-80 degrees centigrade (most preferably 60-65 degrees Centigrade), and a pressure of less than atmospheric (typically 150-200 mm Hg absolute). Preferably, KOH is added as a 40-60 weight per cent solution in water. A vapor stream removed from the epoxidation reactor is fractionated and the overhead epichlorohydrin/water stream is condensed and allowed to separate into two liquid phases. The heavier (organic) phase is returned to the fractionation tower as reflux and from the bottom of the fractionation tower to the epoxidation reactor. (See FIG. 7 and previous description thereof). The aqueous phase is sent forward in the process in the same manner as previously described for the epoxy process to serve as wash water which removes the last traces of KCl from the GMA product before the epichlorohydrin is stripped and the product recovered.
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
alkali metal hydroxides
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[C:1]([O:6][CH2:7][CH:8]([OH:11])[CH2:9][Cl:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH-].[Na+].[OH-].[K+:15].C(C1OC1)Cl>O>[C:1]([O:6][CH2:7][CH:8]1[O:11][CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[Cl-:10].[K+:15] |f:1.2,3.4,8.9|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(=C)C)(=O)OCC(CCl)O
Name
alkali metal hydroxides
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(Cl)C1CO1
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(=C)C)(=O)OCC(CCl)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
are added

Outcomes

Product
Name
Type
product
Smiles
C(C(=C)C)(=O)OCC1CO1
Name
Type
product
Smiles
[Cl-].[K+]

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
US05245057

Procedure details

A feed with 3-chloro-2-hydroxypropyl methacrylate (CHPMA), epichlorohydrln, and minor amounts of by-products (GMA and heavies such as polymer by-product materials) flows into an epoxidation reactor to which aqueous alkali metal hydroxides such as sodium hydroxide (NaOH) or potassium hydroxide (KOH) and additional epichlorohydrin are added. KOH reacts with CHPMA to form glycidyl methacrylate to (GMA), water, and potassium chloride (KCl). Sodium hydroxide may be used in place of KOH, but a higher GMA yield is obtained using KOH. Preferable reaction conditions are: starting molar epichlorohydrin/CHPMA ratio of 6.0 or higher (most preferably 9.0), molar KOH/CHPMA ratio of 0.8-1.5 (most preferably 1.1, temperature of 40-80 degrees centigrade (most preferably 60-65 degrees Centigrade), and a pressure of less than atmospheric (typically 150-200 mm Hg absolute). Preferably, KOH is added as a 40-60 weight per cent solution in water. A vapor stream removed from the epoxidation reactor is fractionated and the overhead epichlorohydrin/water stream is condensed and allowed to separate into two liquid phases. The heavier (organic) phase is returned to the fractionation tower as reflux and from the bottom of the fractionation tower to the epoxidation reactor. (See FIG. 7 and previous description thereof). The aqueous phase is sent forward in the process in the same manner as previously described for the epoxy process to serve as wash water which removes the last traces of KCl from the GMA product before the epichlorohydrin is stripped and the product recovered.
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
alkali metal hydroxides
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[C:1]([O:6][CH2:7][CH:8]([OH:11])[CH2:9][Cl:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH-].[Na+].[OH-].[K+:15].C(C1OC1)Cl>O>[C:1]([O:6][CH2:7][CH:8]1[O:11][CH2:9]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[Cl-:10].[K+:15] |f:1.2,3.4,8.9|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(=C)C)(=O)OCC(CCl)O
Name
alkali metal hydroxides
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(Cl)C1CO1
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(=C)C)(=O)OCC(CCl)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
are added

Outcomes

Product
Name
Type
product
Smiles
C(C(=C)C)(=O)OCC1CO1
Name
Type
product
Smiles
[Cl-].[K+]

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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