IP Library Granted Patent US 10,654,798
Granted Patent B2
US 10,654,798 · App. 16/288,870 · Granted May 19, 2020

Process for continuous industrial synthesis of alkane-suphonicacid

Inventor: Jean-Luc Dubois (Colombes, FR)
Assignee: ARKEMA FRANCE
C07C303/06C07C309/04
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Quick Facts
Patent No.
US 10,654,798
App. No.
16/288,870
Granted
May 19, 2020
Kind
B2
Abstract

A process for the continuous industrial preparation of an alkane-sulphonic acid, from the corresponding alkane and sulphur trioxide, said process being carried out in a solvent which is the alkane-sulphonic acid. The process includes e1) addition of sulphur trioxide in order to maintain an initial molar ratio (alkanesulphonic acid)/(sulphur trioxide), addition of alkane in order to maintain a molar ratio (alkane)/(sulphur trioxide) comprised between 4/1 and 2/1, and continuous withdrawal of the alkanesulphonic acid.

Claims (23)

1. A process for the continuous industrial preparation of alkanesulphonic acid of formula C n H 2n+1 SO 3 H from the alkane of formula C n H 2n+2 , wherein n represents an integer between 1 and 20 inclusive, said process comprising at least the following steps:

a) loading of alkanesulphonic acid C n H 2n+1 SO 3 H, wherein n is as defined above, in a reactor,

b) heating said alkanesulphonic acid at a temperature between 25° C. and 120° C.,

c) introducing a quantity of sulphur trioxide so that the molar ratio (alkanesulphonic acid)/(sulphur trioxide) is between 70/30 and 95/5,

d) introducing the alkane under a pressure between 4 MPa and 15 MPa,

e) introducing a radical initiator,

f) continuous conducting of the reaction, and simultaneously or in any order performing the following three sub-steps f1), f2) and f3):

f1) addition of sulphur trioxide in order to maintain the initial molar ratio (alkanesulphonic acid)/(sulphur trioxide) defined in step c),

f2) addition of alkane in order to maintain a molar ratio (alkane)/(sulphur trioxide) between 4/1 and 2/1, and

f3) continuous withdrawal of the alkanesulphonic acid of formula C n H2 n+1 SO 3 H, and

g) recovery of the alkanesulphonic acid of formula C n H 2n+1 SO 3 H after optional separation of unreacted reagents, and optionally any undesired by-products.

2. The process according to claim 1 , wherein the reaction temperature is between 25° C. and 70° C.

3. The process according to claim 1 wherein the reaction pressure is between 5 MPa and 12 MPa.

4. The process according to claim 1 , wherein the reactor is selected from reactors equipped with a recirculation loop, self-suction turbine reactors, reactors equipped with a venturi system, rotary bed reactors, and tubular reactors.

5. The process according to claim 1 , wherein the radical initiator is selected from azo-bis-iso-butyronitrile, inorganic or organic peroxides, mercury sulphate, palladium sulphate, caesium sulphate, K 2 P 2 O 8 , CaO 2 , halogens, wherein n is as previously defined, the initiators of formula C n H 2n+1 SO 2 —O—O—SO 2 OX, wherein n is as defined above and X is hydrogen, an alkali or alkaline earth metal, zinc or aluminium, Caro acid and its salts with one or more alkali or alkaline earth metals, and Marshall acid and its salts with one or more alkali or alkaline earth metals.

6. The process according to claim 1 , wherein alkane and sulphur trioxide are added as they are consumed and the amount of alkanesulphonic acid withdrawn, while maintaining the molar ratio (alkane of formula C n H 2n+2 )/(sulphur trioxide) between 3.5/1 and 2.5/1, and the molar ratio (alkanesulphonic acid)/(sulphur trioxide) between 70/30 and 95/5.

7. The process according to claim 1 , wherein the solvent is methanesulphonic acid, the alkane is methane, and the continuously withdrawn product is methanesulphonic acid.

8. A reaction medium comprising an alkane sulphonic acid of formula C n H 2n+1 SO 3 H, wherein n is an integer between 1 and 20 inclusive, sulphur trioxide SO 3 , and an alkane of formula C n H 2n+2 , wherein n is as previously defined, said reaction medium, in which:

the molar ratio (alkanesulphonic acid)/(SO 3 ) is between 70/30 and 95/5, and

the molar ratio (alkane)/(SO 3 ) is between 4/1 and 2/1.

9. The reaction medium of claim 8 , comprising methanesulphonic acid (CH 3 SO 3 H), sulphur trioxide SO 3 , and methane (CH 4 ) wherein:

the molar ratio (alkanesulphonic acid)/(SO 3 ) is between 70/30 and 95/5, and

the molar ratio (methane)/(SO 3 ) is between 3.5/1 and 2.5/1.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2019
From: DUBOIS, JEAN-LUC
To: ARKEMA FRANCE
Reel/Frame 049063/0066 →
Priority Claims (1)
FR 18 51230 · Feb 14, 2018 · national
Continuity (1)
Related Publication 20190276394A1 · Sep 12, 2019