A method and a production system for recovering and treating taurine mother liquor, which is used for the process of ethylene oxide taurine production process. As for the treatment of the last mother liquor of taurine, add alkali firstly to the last mother liquor of taurine and then acid to form salt, or add salt directly; then concentrate and crystallize and filter, to remove lots of impurities in taurine mother liquor. This solves the problem of separating impurities, greatly shortening the time of removing impurities. The last mother liquor can also be decolorizes and additional impurities removes by activated carbon, and the removal of salt by mixing ammonia into the mother liquor to obtain the pure taurine mother liquor, thereby recovering the mother liquor and increasing the product yield.

A method and a production system for recovering and treating taurine mother liquor, which is used for the process of ethylene oxide taurine production process. As for the treatment of the last mother liquor of taurine, add alkali firstly to the last mother liquor of taurine and then acid to form salt, or add salt directly; then concentrate and crystallize and filter, to remove lots of impurities in taurine mother liquor. This solves the problem of separating impurities, greatly shortening the time of removing impurities. The last mother liquor can also be decolorizes and additional impurities removes by activated carbon, and the removal of salt by mixing ammonia into the mother liquor to obtain the pure taurine mother liquor, thereby recovering the mother liquor and increasing the product yield.

The present invention provides a method for preparing a compound of Formula C, Formula D, or Formula F:

##STR00001##

wherein each R.sup.1, R.sup.2, and R.sup.3 is independently H, SFs, N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), C(═S)N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), SO.sub.2N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), OSO.sub.2(C.sub.1-C.sub.8 alkyl), OSO.sub.2N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), N(C.sub.1-C.sub.8 alkyl)SO.sub.2(C.sub.1-C.sub.8 alkyl), or C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 haloalkyl, C.sub.2-C.sub.8 alkenyl, C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.10 cycloalkyl, C.sub.3-C.sub.10 halocycloalkyl, C.sub.4-C.sub.10 alkylcycloalkyl, C.sub.4-C.sub.10 cycloalkylalkyl, C.sub.6-C.sub.14 cycloalkylcycloalkyl, C.sub.5-C.sub.10 alkylcycloalkylalkyl, C.sub.3-C.sub.8 cycloalkenyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 haloalkoxy, C.sub.3-C.sub.8 cycloalkoxy, C.sub.3-C.sub.8 halocycloalkoxy, C.sub.4-C.sub.10 cycloalkylalkoxy, C.sub.2-C.sub.8 alkenyloxy, C.sub.2-C.sub.8 alkynyloxy, C.sub.1-C.sub.8 alkylthio, C.sub.1-C.sub.8 alkylsulfinyl, C.sub.1-C.sub.8 alkylsulfonyl, C.sub.3-C.sub.8 cycloalkylthio, C.sub.3-C.sub.8 cycloalkylsulfinyl, C.sub.3-C.sub.8 cycloalkylsulfonyl, C.sub.4-C.sub.10 cycloalkylalkylthio, C.sub.4-C.sub.10 cycloalkylalkylsulfinyl, C.sub.4-C.sub.10 cycloalkylalkylsulfonyl, C.sub.2-C.sub.8 alkenylthio, C.sub.2-C.sub.8 alkenylsulfinyl, C.sub.2-C.sub.8 alkenylsulfonyl, C.sub.2-C.sub.8 alkynylthio, C.sub.2-C.sub.8 alkynylsulfinyl, C.sub.2-C.sub.8 alkynylsulfonyl, or phenyl; or

two of R.sup.1, R.sup.2, and R.sup.3 on adjacent ring atoms may be taken together to form a 5- to 7 -membered carbocyclic or heterocyclic ring, each ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 3 N, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and such ring is optionally substituted with up to 3 substituents independently selected from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.8 alkylcycloalkyl, C.sub.4-C.sub.8 haloalkylcycloalkyl, C.sub.4-C.sub.8 cycloalkylalkyl, C.sub.4-C.sub.8 halocycloalkylalkyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 haloalkoxy, C.sub.2-C.sub.8 alkoxycarbonyl, C.sub.2-C.sub.6 haloalkoxycarbonyl, C.sub.2-C.sub.6 alkylcarbonyl and C.sub.2-C.sub.6 haloalkylcarbonyl; and

M is an inorganic cation or organic cation.

The present invention provides a method for preparing a compound of Formula C, Formula D, or Formula F:

##STR00001##

wherein each R.sup.1, R.sup.2, and R.sup.3 is independently H, SFs, N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), C(═S)N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), SO.sub.2N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), OSO.sub.2(C.sub.1-C.sub.8 alkyl), OSO.sub.2N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), N(C.sub.1-C.sub.8 alkyl)SO.sub.2(C.sub.1-C.sub.8 alkyl), or C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 haloalkyl, C.sub.2-C.sub.8 alkenyl, C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.10 cycloalkyl, C.sub.3-C.sub.10 halocycloalkyl, C.sub.4-C.sub.10 alkylcycloalkyl, C.sub.4-C.sub.10 cycloalkylalkyl, C.sub.6-C.sub.14 cycloalkylcycloalkyl, C.sub.5-C.sub.10 alkylcycloalkylalkyl, C.sub.3-C.sub.8 cycloalkenyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 haloalkoxy, C.sub.3-C.sub.8 cycloalkoxy, C.sub.3-C.sub.8 halocycloalkoxy, C.sub.4-C.sub.10 cycloalkylalkoxy, C.sub.2-C.sub.8 alkenyloxy, C.sub.2-C.sub.8 alkynyloxy, C.sub.1-C.sub.8 alkylthio, C.sub.1-C.sub.8 alkylsulfinyl, C.sub.1-C.sub.8 alkylsulfonyl, C.sub.3-C.sub.8 cycloalkylthio, C.sub.3-C.sub.8 cycloalkylsulfinyl, C.sub.3-C.sub.8 cycloalkylsulfonyl, C.sub.4-C.sub.10 cycloalkylalkylthio, C.sub.4-C.sub.10 cycloalkylalkylsulfinyl, C.sub.4-C.sub.10 cycloalkylalkylsulfonyl, C.sub.2-C.sub.8 alkenylthio, C.sub.2-C.sub.8 alkenylsulfinyl, C.sub.2-C.sub.8 alkenylsulfonyl, C.sub.2-C.sub.8 alkynylthio, C.sub.2-C.sub.8 alkynylsulfinyl, C.sub.2-C.sub.8 alkynylsulfonyl, or phenyl; or

two of R.sup.1, R.sup.2, and R.sup.3 on adjacent ring atoms may be taken together to form a 5- to 7 -membered carbocyclic or heterocyclic ring, each ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 3 N, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and such ring is optionally substituted with up to 3 substituents independently selected from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.8 alkylcycloalkyl, C.sub.4-C.sub.8 haloalkylcycloalkyl, C.sub.4-C.sub.8 cycloalkylalkyl, C.sub.4-C.sub.8 halocycloalkylalkyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 haloalkoxy, C.sub.2-C.sub.8 alkoxycarbonyl, C.sub.2-C.sub.6 haloalkoxycarbonyl, C.sub.2-C.sub.6 alkylcarbonyl and C.sub.2-C.sub.6 haloalkylcarbonyl; and

M is an inorganic cation or organic cation.

The present invention provides a method for preparing a compound of Formula C, Formula D, or Formula F:

##STR00001##

wherein each R.sup.1, R.sup.2, and R.sup.3 is independently H, SFs, N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), C(═S)N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), SO.sub.2N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), OSO.sub.2(C.sub.1-C.sub.8 alkyl), OSO.sub.2N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), N(C.sub.1-C.sub.8 alkyl)SO.sub.2(C.sub.1-C.sub.8 alkyl), or C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 haloalkyl, C.sub.2-C.sub.8 alkenyl, C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.10 cycloalkyl, C.sub.3-C.sub.10 halocycloalkyl, C.sub.4-C.sub.10 alkylcycloalkyl, C.sub.4-C.sub.10 cycloalkylalkyl, C.sub.6-C.sub.14 cycloalkylcycloalkyl, C.sub.5-C.sub.10 alkylcycloalkylalkyl, C.sub.3-C.sub.8 cycloalkenyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 haloalkoxy, C.sub.3-C.sub.8 cycloalkoxy, C.sub.3-C.sub.8 halocycloalkoxy, C.sub.4-C.sub.10 cycloalkylalkoxy, C.sub.2-C.sub.8 alkenyloxy, C.sub.2-C.sub.8 alkynyloxy, C.sub.1-C.sub.8 alkylthio, C.sub.1-C.sub.8 alkylsulfinyl, C.sub.1-C.sub.8 alkylsulfonyl, C.sub.3-C.sub.8 cycloalkylthio, C.sub.3-C.sub.8 cycloalkylsulfinyl, C.sub.3-C.sub.8 cycloalkylsulfonyl, C.sub.4-C.sub.10 cycloalkylalkylthio, C.sub.4-C.sub.10 cycloalkylalkylsulfinyl, C.sub.4-C.sub.10 cycloalkylalkylsulfonyl, C.sub.2-C.sub.8 alkenylthio, C.sub.2-C.sub.8 alkenylsulfinyl, C.sub.2-C.sub.8 alkenylsulfonyl, C.sub.2-C.sub.8 alkynylthio, C.sub.2-C.sub.8 alkynylsulfinyl, C.sub.2-C.sub.8 alkynylsulfonyl, or phenyl; or

two of R.sup.1, R.sup.2, and R.sup.3 on adjacent ring atoms may be taken together to form a 5- to 7 -membered carbocyclic or heterocyclic ring, each ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 3 N, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and such ring is optionally substituted with up to 3 substituents independently selected from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.8 alkylcycloalkyl, C.sub.4-C.sub.8 haloalkylcycloalkyl, C.sub.4-C.sub.8 cycloalkylalkyl, C.sub.4-C.sub.8 halocycloalkylalkyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 haloalkoxy, C.sub.2-C.sub.8 alkoxycarbonyl, C.sub.2-C.sub.6 haloalkoxycarbonyl, C.sub.2-C.sub.6 alkylcarbonyl and C.sub.2-C.sub.6 haloalkylcarbonyl; and

M is an inorganic cation or organic cation.

Improved initiators, solvents, and SO3 mixtures are disclosed herein, which can increase the yields and efficiency of a chemical manufacturing process which uses a radical chain reaction to convert methane (CH4), which is a gas under any normal conditions, into methane-sulfonic acid (MSA), a liquid. MSA is useful and valuable in its own right, and it also can be processed to create desulfured fuels and other valuable chemicals. A preferred initiator combination has been identified, comprising at least two different sulfate peroxide compounds. One type or class of initiator can be called a “primary” (or major, main, principle, dominant, or similar terms) initiator, and the other type or class of initiator can be can be regarded as an “extender” (or secondary, supplemental, enhancing, tuning, tweaking, or similar terms) initiator. “Primary” initiator(s) include (unmethylated) Marshall's acid, mono-methyl-Marshall's acid, and di-methyl-Marshall's acid, while a secondary/extender initiator comprises methyl-Caro's acid, which can oxidize sulfur DI-oxide (an unwanted chain terminator) into sulfur TRI-oxide (an essential reagent). Various other enhancements to the MSA manufacturing process also are described.

Improved initiators, solvents, and SO3 mixtures are disclosed herein, which can increase the yields and efficiency of a chemical manufacturing process which uses a radical chain reaction to convert methane (CH4), which is a gas under any normal conditions, into methane-sulfonic acid (MSA), a liquid. MSA is useful and valuable in its own right, and it also can be processed to create desulfured fuels and other valuable chemicals. A preferred initiator combination has been identified, comprising at least two different sulfate peroxide compounds. One type or class of initiator can be called a “primary” (or major, main, principle, dominant, or similar terms) initiator, and the other type or class of initiator can be can be regarded as an “extender” (or secondary, supplemental, enhancing, tuning, tweaking, or similar terms) initiator. “Primary” initiator(s) include (unmethylated) Marshall's acid, mono-methyl-Marshall's acid, and di-methyl-Marshall's acid, while a secondary/extender initiator comprises methyl-Caro's acid, which can oxidize sulfur DI-oxide (an unwanted chain terminator) into sulfur TRI-oxide (an essential reagent). Various other enhancements to the MSA manufacturing process also are described.

Improved initiators, solvents, and SO3 mixtures are disclosed herein, which can increase the yields and efficiency of a chemical manufacturing process which uses a radical chain reaction to convert methane (CH4), which is a gas under any normal conditions, into methane-sulfonic acid (MSA), a liquid. MSA is useful and valuable in its own right, and it also can be processed to create desulfured fuels and other valuable chemicals. A preferred initiator combination has been identified, comprising at least two different sulfate peroxide compounds. One type or class of initiator can be called a “primary” (or major, main, principle, dominant, or similar terms) initiator, and the other type or class of initiator can be can be regarded as an “extender” (or secondary, supplemental, enhancing, tuning, tweaking, or similar terms) initiator. “Primary” initiator(s) include (unmethylated) Marshall's acid, mono-methyl-Marshall's acid, and di-methyl-Marshall's acid, while a secondary/extender initiator comprises methyl-Caro's acid, which can oxidize sulfur DI-oxide (an unwanted chain terminator) into sulfur TRI-oxide (an essential reagent). Various other enhancements to the MSA manufacturing process also are described.

There is disclosed a cyclic process for producing taurine from monoethanolamine comprising the steps of: (a) recovering monoethanolamine sulfate from an aqueous mother liquor solution; (b) reacting the monoethanolamine sulfate with sulfuric acid to form an aqueous solution comprised of monoethanolamine bisulfate; (c) heating the aqueous solution comprised of the monoethanolamine sulfate and optionally added monoethanolamine sulfate to yield 2-aminoethyl hydrogen sulfate ester; (d) reacting the ester with ammonium sulfite or an alkali sulfite to yield taurine and ammonium or alkali sulfate; (e) separating taurine and ammonium or alkali sulfate to give an aqueous mother liquor solution; and (f) recovering the monoethanolamine sulfate from the aqueous mother liquor solution and recycling to the monoethanolamine sulfate to step (b).

The present invention relates to a compound according to Formula (3), wherein the compound comprises from 28 wt. % to 100 wt. % bio-based carbon content, relative to the total mass of carbon in the compound, measured according to standard ASTM D6866-12, Method B; ##STR00001## and wherein X.sup.+is a proton. The present invention also relates to a polymer obtained by polymerising at least one of compound according to Formula (3), in addition to processes and uses related thereto.