US2003105352A1PendingUtilityA1
Arylalkylsulfonic acids and methods for producing same
Priority: Aug 3, 2001Filed: Aug 3, 2001Published: Jun 5, 2003
Est. expiryAug 3, 2021(expired)· nominal 20-yr term from priority
C07C 303/22C11D 1/22
43
PatentIndex Score
0
Cited by
0
References
0
Claims
Abstract
This invention relates new and improved processes for the preparation of arylalkylsulfonic acids derived from aromatic or substituted aromatic molecules and AOS acid (generally a mixture of alkenesulfonic acid and sultones, produced from the sulfonation of alpha olefins). The invention involves the use of a superacid catalyst to effectuate the conversion of AOS acid and aromatic reactants to arylalkylsulfonic acid under substantially anhydrous conditions, whereby a substantial improvement in the rate of conversion of the reactants to arylalkylsulfonic acid and/or improvement in mono-alkylation selectivity is realized, as compared to methods of preparation previously disclosed. Also useful as an alkylation promoter is the arylalkylsulfonic acid reaction product itself, produced in situ or from a previous reaction (i.e., a self-catalyst heel). The new processes generally afford arylalkylsulfonic acids with substantially improved conversion yields, highly desirable lighter color, and reduced odor, as compared to previously known methods. The acids produced by the inventive process may be neutralized to form arylalkylsulfonates (i.e., a neutralized form of the acid) which are useful in a variety of end use applications as surfactants and/or emulsifiers.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A method for preparing an arylalkylsulfonic acid comprising alkylating an aromatic compound with an AOS acid in the presence of a superacid catalyst and at a temperature sufficient to produce an arylalkylsulfonic acid, wherein the alkylation is conducted under substantially anhydrous conditions.
2 . A method according to claim 1 , wherein the aromatic compound is selected from the group consisting of benzene, a mono-substituted aromatic compound, a poly-substituted aromatic compound, alkylbenzene, alkoxylated benzene, a polycyclic aromatic compound, a mono-substituted polycyclic aromatic compound, a poly-substituted polycyclic aromatic compound, naphthalene and alkylnaphthalene, or a mixture thereof.
3 . A method according to claim 1 , wherein the aromatic compound is selected from the group consisting of phenol, alkylphenol, alkoxylated phenol, and alkoxylated alkylphenol, or a mixture thereof.
4 . A method according to claim 2 , wherein the aromatic compound is selected form the group consisting of benzene, toluene, xylene, cumene, ethyl benzene, propylbenzene and naphthalene, or a mixture thereof.
5 . A method according to claim 4 , where in the aromatic compound is benzene or toluene.
6 . A method according to claim 1 , wherein the AOS acid comprises an alkene sulfonic acid, a sultone or a mixture thereof.
7 . A method according to claim 6 , and wherein the sultone is of the formula:
and wherein the alkene sulfonic acid is of the formula:
wherein a is 1, 2 or 3 and b is an integer 1 to 31; wherein c and d are independently integers 0 to 33, provided that c+d=1 to 33.
8 . A method according to claim 1 , wherein the molar ratio of alkene sulfonic acid to sultone is from about 1:1 to about 1:4.
9 . A method according to claim 1 , wherein the molar ratio of aromatic compound to AOS acid is from about 1:1 to about 30:1.
10 . A method according to claim 9 , wherein the molar ratio of aromatic compound to AOS acid is from about 2:1 to about 10:1.
11 . A method according to claim 1 , wherein the superacid catalyst is selected from the group consisting of a solid superacid, a perfluorosulfonic acid resin, a supported perfluorosulfonic acid resin, a metal sulfate, zirconium sulfate, zirconium tungstate, a sulfated metal oxyhydroxyide, a sulfated metal oxysilicate, a superacid metal oxide, CF 3 SO 3 H, or a mixture thereof.
12 . A method according to claim 11 , wherein the superacid catalyst is a perfluorosulfonic acid resin or a supported perfluorosulfonic acid resin.
13 . A method according to claim 12 , wherein the perfluorosulfonic acid resin is a copolymer of sulfonyl fluorovinyl ether and a fluorocarbon.
14 . A method according to claim 1 , wherein the arylalkylsulfonic acid comprises a compound of the formula:
wherein m and n are independently integers 0 to 34, provided that m+n is at least 2 and wherein m+n is equal to or less than 34; wherein R and R′ are independently branched or straight chain C 1-36 alkyl or substituted alkyl.
15 . A method according to claim 14 , wherein the arylalkylsulfonic acid further comprises a compound of the formula:
wherein m and n are independently 0-34, provided that m+n is at least 2 and wherein m+n is equal to or less than 34; wherein o and p are independently 0-34, provided that o+p is at least 2 and wherein o+p is equal to or less than 34; wherein R and R′ are independently branched or straight chain C 1-36 alkyl or substituted alkyl.
16 . A method according to claim 15 , wherein the arylalkylsulfonic acid further comprises an AOS acid dimer compound of the formula:
wherein a and b are independently 0-34, provided that a +b is at least 2 and wherein a +b is equal to or less than 34; wherein c and d are independently 0-34, provided that c+d is at least 2 and wherein c+d is equal to or less than 34.
17 . A method according to claim 1 , wherein the alkylation is conducted at a temperature from about 80° C. to about 200° C.
18 . A method according to claim 17 , wherein the alkylation is conducted at a temperature from about 100° C. to about 150° C.
19 . A method for preparing an arylalkylsulfonic acid, comprising:
a) sulfonating an alpha olefin to form an AOS acid; b) alkylating an aromatic compound with the AOS acid in the presence of a superacid catalyst, wherein the alkylation is conducted under substantially anhydrous conditions and at a temperature sufficient to produce an arylalkylsulfonic acid.
20 . A method according to claim 19 , wherein the aromatic compound is selected from the group consisting of benzene, a mono-substituted aromatic compound, a poly-substituted aromatic compound, alkylbenzene, alkoxylated benzene, a polycyclic aromatic compound, a mono-substituted polycyclic aromatic compound, a poly-substituted polycyclic aromatic compound, naphthalene and alkylnaphthalene, or a mixture thereof.
21 . A method according to claim 19 , wherein the aromatic compound is selected from the group consisting of phenol, alkylphenol, alkoxylated phenol, and alkoxylated alkylphenol, or a mixture thereof.
22 . A method according to claim 20 , wherein the aromatic compound is selected form the group consisting of benzene, toluene, xylene, ethyl benzene, propylbenzene and naphthalene, or a mixture thereof.
23 . A method according to claim 22 , where in the aromatic compound is benzene or toluene.
24 . A method according to claim 20 , wherein the AOS acid comprises an alkene sulfonic acid, a sultone or a mixture thereof.
25 . A method according to claim 24 , wherein the sultone is of the formula:
and wherein the alkene sulfonic acid is of the formula:
wherein a is 1, 2 or 3 and b is an integer 1 to 31; wherein c and d are independently integers 0 to 33, provided that c+d=1 to 33,
26 . A method according to claim 21 , wherein the molar ratio of alkene sulfonic acid to sultone is from about 1:1 to about 1:4.
27 . A method according to claim 19 , wherein the molar ratio of aromatic compound to AOS acid is from about 1:1 to about 30:1.
28 . A method according to claim 27 , wherein the molar ratio of aromatic compound to AOS acid is from about 2:1 to about 10:1.
29 . A method according to claim 19 , wherein the superacid catalyst is selected from the group consisting of a solid super-acid, a perfluorosulfonic acid resin, a supported perfluorosulfonic acid resin, a metal sulfate, zirconium sulfate, zirconium tungstate, a sulfated metal oxyhydroxyide, a sulfated metal oxysilicate, a superacid metal oxide, CF 3 SO 3 H, or a mixture thereof.
30 . A method according to claim 29 , wherein the superacid catalyst is a perfluorosulfonic acid resin or a supported perfluorosulfonic acid resin.
31 . A method according to claim 30 , wherein the perfluorosulfonic acid resin is a copolymer of sulfonyl fluorovinyl ether and a fluorocarbon.
32 . A method according to claim 19 , wherein the arylalkylsulfonic acid comprises a compound of the formula:
wherein m and n are independently integers 0 to 34, provided that m+n is at least 2 and wherein m+n is equal to or less than 34; wherein R and R′ are independently branched or straight chain C 1-36 alkyl or substituted alkyl.
33 . A method according to claim 32 , wherein the arylalkylsulfonic acid further comprises a compound of the formula:
wherein m and n are independently 0-34, provided that m+n is at least 2 and wherein m+n is equal to or less than 34; wherein o and p are independently 0-34, provided that o+p is at least 2 and wherein o+p is equal to or less than 34; wherein R and R′ are independently branched or straight chain C 1-36 alkyl or substituted alkyl.
34 . A method according to claim 33 , wherein the arylalkylsulfonic acid further comprises an AOS acid dimer compound of the formula:
wherein a and b are independently 0-34, provided that a +b is at least 2 and wherein a +b is equal to or less than 34; wherein c and d are independently 0-34, provided that c+d is at least 2 and wherein c+d is equal to or less than 34.
35 . A method according to claim 19 , wherein the alpha olefin is of the formula
wherein n=1-33.
36 . A method according to claim 19 , wherein the alkylation is conducted at a temperature of about 80° C. to about 200° C.
37 . A method according to claim 36 , wherein the alkylation is conducted at a temperature of about 100° C. to about 150° C.
38 . A method for preparing an arylalkylsulfonic acid comprising alkylating an aromatic compound with an AOS acid in the presence of an alkylation promoter comprising a compound of the formula:
wherein m and n are independently integers 0 to 34, provided that m+n is at least 2 and wherein m+n is equal to or less than 34; wherein R and R′ are independently branched or straight chain C 1-36 alkyl or substituted alkyl, wherein the alkylation is conducted at a temperature sufficient to produce an arylalkylsulfonic acid; and wherein the alkylation is conducted under substantially anhydrous conditions; and wherein the alkylation promoter is present in at least 25% by weight, based on the weight of the AOS acid.
39 . A method for preparing an arylalkylsulfonic acid according to claim 38 , wherein the alkylation promoter further comprises a compound of the formula:
wherein m and n are independently 0-34, provided that m+n is at least 2 and wherein m+n is equal to or less than 34; wherein o and p are independently 0-34, provided that o+p is at least 2 and wherein o+p is equal to or less than 34; wherein R and R′ are independently branched or straight chain C 1-36 alkyl or substituted alkyl.
40 . A method for preparing an arylalkylsulfonic acid according to claim 39 , wherein the alkylation promoter further comprises a compound of the formula:
wherein a and b are independently 0-34, provided that a +b is at least 2 and wherein a +b is equal to or less than 34; wherein c and d are independently 0-34, provided that c+d is at least 2 and wherein c+d is equal to or less than 34.
41 . A method according to claim 38 , wherein the AOS acid comprises an alkene sulfonic acid, a sultone or a mixture thereof.
42 . A method according to claims 38 , wherein the alkylation promotion agent further comprises a superacid catalyst selected from the group consisting of a solid super-acid, a perfluorosulfonic acid resin, a supported perfluorosulfonic acid resin, a metal sulfate, zirconium sulfate, zirconium tungstate, a sulfated metal oxyhydroxyide, a sulfated metal oxysilicate, a superacid metal oxide, CF 3 SO 3 H, or a mixture thereof.
43 . A method for preparing an arylalkylsulfonic acid comprising
a) sulfonating an alpha olefin to form an AOS acid which comprises an alkene sulfonic acid and a sultone; b) alkylating an aromatic compound with the AOS acid in the presence of an alkylation promoter comprising compounds of the formula: wherein m and n are independently integers 0 to 34, provided that m+n is at least 2 and wherein m+n is equal to or less than 34; wherein R and R′ are independently branched or straight chain C 1-36 alkyl or substituted alkyl, wherein the alkylation is conducted at a temperature sufficient to produce an arylalkylsulfonic acid, and wherein the alkylation is conducted under substantially anhydrous conditions.
44 . An arylalkylsulfonic acid produced by the process of claims 1 .
45 . An arylalkylsulfonic acid produced by the process of claims 19 .
46 . An arylalkylsulfonic acid produced by the process of claims 38 .
47 . An arylalkylsulfonic acid produced by the process of claims 43 .Join the waitlist — get patent alerts
Track US2003105352A1 — get alerts on status changes and closely related new filings.
We store only your email — no account needed. See our privacy policy.