EMM-28, a novel synthetic crystalline material, its preparation and use

A method of producing a 1,1′-(1,x-phenylenebis(propane-3,1-diyl))bis(1-methylpyrrolidin-1-ium) compound, where x is 2, 3 or 4, the method comprising:

• reacting 1,x-bis(halomethyl)benzene with a dialkyl malonate to produce a tetraalkyl 2,2′-(1,x-phenylenebis(methylene))dimalonate;
• converting at least part of the tetraalkyl 2,2′-(1,x-phenylenebis(methylene))dimalonate to 3,3′-(1,x-phenylene)dipropanoic acid;
• reducing at least part of the 3,3′-(1,x-phenylene)dipropanoic acid, or an ester thereof, to 3,3′-(1,x-phenylene)bis(propan-1-ol));
• reacting at least part of the 3,3′-(1,x-phenylene)bis(propan-1-ol)) with an alkyl- or aryl-sulfonyl halide to produce the corresponding sulfonate diester;
• reacting at least part of the sulfonate diester with pyrrolidine to produce 1,x-bis(3-(pyrrolidin-1-yl)propyl)benzene;
• and
• reacting at least part of the 1,x-bis(3-(pyrrolidin-1-yl)propyl)benzene with a methyl halide to produce a 1,1′-(1,x-phenylenebis(propane-3,1-diyl))bis(1-methylpyrrolidin-1-ium) halide.

A method of producing a 1,1′-(1,x-phenylenebis(propane-3,1-diyl))bis(1-methylpyrrolidin-1-ium) compound, where x is 2, 3 or 4, the method comprising:

• reacting 1,x-bis(halomethyl)benzene with a dialkyl malonate to produce a tetraalkyl 2,2′-(1,x-phenylenebis(methylene))dimalonate;
• converting at least part of the tetraalkyl 2,2′-(1,x-phenylenebis(methylene))dimalonate to 3,3′-(1,x-phenylene)dipropanoic acid;
• reducing at least part of the 3,3′-(1,x-phenylene)dipropanoic acid, or an ester thereof, to 3,3′-(1,x-phenylene)bis(propan-1-ol));
• reacting at least part of the 3,3′-(1,x-phenylene)bis(propan-1-ol)) with an alkyl- or aryl-sulfonyl halide to produce the corresponding sulfonate diester;
• and
• reacting at least part of the sulfonate diester with 1-methylpyrrolidine to produce a 1,1′-(1,x-phenylenebis(propane-3,1-diyl))bis(1-methylpyrrolidin-1-ium) compound.

A method of producing a 1,1′-(1,x-phenylenebis(propane-3,1-diyl))bis(1-methylpyrrolidin-1-ium) compound, where x is 2, 3 or 4, the method comprising:

• reacting 1-(prop-2-yn-1-yl)pyrrolidine with a 1,x-dihalo-substituted benzene to produce a compound of formula (IVA), (IVB) or (IVC):
• hydrogenating at least part of the compound of formula (IVA), (IVB) or (IVC) to produce a compound of formula (VA), (VB) or (VC):
• and
• reacting at least part of the compound of formula (VA), (VB) or (VC) with a methyl halide to produce a 1,1′-(1,x-phenylenebis(propane-3,1-diyl))bis(1-methylpyrrolidin-1-ium) halide.

A method of producing a 1,1′-(1,x-phenylenebis(propane-3,1-diyl))bis(1-methylpyrrolidin-1-ium) compound, where x is 2, 3 or 4, the method comprising:

• reacting a compound of formula (VI)
• where R1 is a hydroxyl group, with 1,x-dihalo-substituted benzene to produce a compound of formula (VIIA), (VIIB) or (VIIC):
• hydrogenating at least part of the compound of formula (VIIA), (VIIB) or (VIIC) to produce a compound of formula (VIIIA), (VIIIB) or (VIIIC), respectively:
• and
• reacting at least part of the compound of formula (VIIIA), (VIIIB) or (VIIIC) with an alkyl- or aryl-sulfonyl halide such as p-toluenesulfonyl chloride to produce a compound of formula (XA), (XB) or XC, respectively:
• converting at least part of the compound of formula (XA), (XB) or (XC) to a 1,1′-(1,x-phenylenebis(propane-3,1-diyl))bis(1-methylpyrrolidin-1-ium) compound by (i) reaction with 1-methylpyrrolidine or (ii) by reaction with pyrrolidine and then with a methyl halide.