HUP0204013A2 - Method for treating a reaction mixture containing a sulphinic acid salt whereof the bearing carbon sulphur is perfluorinated - Google Patents

Method for treating a reaction mixture containing a sulphinic acid salt whereof the bearing carbon sulphur is perfluorinated Download PDF

Info

Publication number: HUP0204013A2
Authority: HU; Hungary
Prior art keywords: acid; organic phase; basic; process according; extracted
Prior art date: 2000-01-04

Application number

HU0204013A

Other languages

English (en)

Hungarian (hu)

Inventor

Virginie Pevere

Original Assignee

Rhodia Chimie Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-01-04

Filing date

2001-01-04

Publication date

2003-04-28

2001-01-04 Application filed by Rhodia Chimie Sa filed Critical Rhodia Chimie Sa

2003-04-28 Publication of HUP0204013A2 publication Critical patent/HUP0204013A2/hu

Links

239000002253 acid Substances 0.000 title claims abstract description 39
150000003839 salts Chemical class 0.000 title claims abstract description 21
238000000034 method Methods 0.000 title claims description 24
239000011541 reaction mixture Substances 0.000 title claims description 12
GJEAMHAFPYZYDE-UHFFFAOYSA-N [C].[S] Chemical compound [C].[S] GJEAMHAFPYZYDE-UHFFFAOYSA-N 0.000 title 1
239000012074 organic phase Substances 0.000 claims abstract description 26
239000007788 liquid Substances 0.000 claims abstract description 7
229910052799 carbon Inorganic materials 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
239000008346 aqueous phase Substances 0.000 claims description 31
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 18
239000000243 solution Substances 0.000 claims description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
238000010828 elution Methods 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 13
238000000605 extraction Methods 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 6
239000012071 phase Substances 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 2
230000020477 pH reduction Effects 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
239000003929 acidic solution Substances 0.000 claims 1
125000002091 cationic group Chemical group 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
238000006351 sulfination reaction Methods 0.000 claims 1
150000003455 sulfinic acids Chemical class 0.000 abstract description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
239000011593 sulfur Substances 0.000 abstract description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
150000007513 acids Chemical class 0.000 description 15
239000002585 base Substances 0.000 description 15
150000001412 amines Chemical class 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
150000007514 bases Chemical class 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
238000004821 distillation Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003880 polar aprotic solvent Substances 0.000 description 6
YJPOHGDCIPEPET-UHFFFAOYSA-M potassium;trifluoromethanesulfinate Chemical compound [K+].[O-]S(=O)C(F)(F)F YJPOHGDCIPEPET-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
150000004820 halides Chemical class 0.000 description 5
238000000622 liquid--liquid extraction Methods 0.000 description 5
150000003222 pyridines Chemical class 0.000 description 5
238000000638 solvent extraction Methods 0.000 description 5
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 4
239000012535 impurity Substances 0.000 description 4
CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
125000001453 quaternary ammonium group Chemical group 0.000 description 4
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
-1 benzene Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002798 polar solvent Substances 0.000 description 3
150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
GJHYPUVOTCXKPR-UHFFFAOYSA-N FC(S(=O)[O-])(F)F.C[NH+](C)C Chemical compound FC(S(=O)[O-])(F)F.C[NH+](C)C GJHYPUVOTCXKPR-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000000356 contaminant Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
150000003017 phosphorus Chemical class 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
230000005588 protonation Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
YKGBNAGNNUEZQC-UHFFFAOYSA-N 6-methyl-n,n-bis(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)CCCCCC(C)C YKGBNAGNNUEZQC-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001768 cations Chemical group 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000009795 derivation Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000005272 metallurgy Methods 0.000 description 1
XETFBTXVGCQYBD-UHFFFAOYSA-N methanamine;2,2,2-trifluoroacetic acid Chemical compound [NH3+]C.[O-]C(=O)C(F)(F)F XETFBTXVGCQYBD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000005185 salting out Methods 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
125000000626 sulfinic acid group Chemical group 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical class FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/04—Sulfinic acids; Esters thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

HU0204013A 2000-01-04 2001-01-04 Method for treating a reaction mixture containing a sulphinic acid salt whereof the bearing carbon sulphur is perfluorinated HUP0204013A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0000051A FR2803295B1 (fr)	2000-01-04	2000-01-04	Procede de traitement d'un melange reactionnel contenant un sel d'acide sulfinique dont le carbone porteur de souffre est perfluore
PCT/FR2001/000025 WO2001049659A1 (fr)	2000-01-04	2001-01-04	Procede de traitement d'un melange reactionnel contenant un sel d'acide sulfinique dont le carbone porteur de soufre est perfluore

Publications (1)

Publication Number	Publication Date
HUP0204013A2 true HUP0204013A2 (en)	2003-04-28

Family

ID=8845608

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU0204013A HUP0204013A2 (en)	2000-01-04	2001-01-04	Method for treating a reaction mixture containing a sulphinic acid salt whereof the bearing carbon sulphur is perfluorinated

Country Status (6)

Country	Link
EP (1)	EP1244618A1 (fr)
AU (1)	AU3382701A (fr)
CA (1)	CA2396433A1 (fr)
FR (1)	FR2803295B1 (fr)
HU (1)	HUP0204013A2 (fr)
WO (1)	WO2001049659A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2924115B1 (fr) *	2007-11-27	2010-02-26	Rhodia Operations	Procede de preparation d'un acide trifluoromethanesulfinique
FR2924116B1 (fr)	2007-11-27	2010-02-26	Rhodia Operations	Procede de preparation d'un sel de l'acide trifluoromethanesulfinique

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2661409A1 (fr) *	1990-04-27	1991-10-31	Rhone Poulenc Chimie	Procede de purification des trifluoromethanesulfinate et sulfonate de sodium.

2000
- 2000-01-04 FR FR0000051A patent/FR2803295B1/fr not_active Expired - Fee Related
2001
- 2001-01-04 WO PCT/FR2001/000025 patent/WO2001049659A1/fr not_active Ceased
- 2001-01-04 AU AU33827/01A patent/AU3382701A/en not_active Abandoned
- 2001-01-04 CA CA002396433A patent/CA2396433A1/fr not_active Abandoned
- 2001-01-04 HU HU0204013A patent/HUP0204013A2/hu unknown
- 2001-01-04 EP EP01905851A patent/EP1244618A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
AU3382701A (en)	2001-07-16
WO2001049659A1 (fr)	2001-07-12
FR2803295B1 (fr)	2002-02-08
FR2803295A1 (fr)	2001-07-06
CA2396433A1 (fr)	2001-07-12
EP1244618A1 (fr)	2002-10-02

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EP1423396B1 (fr)	2011-10-05	Synthese de quinols et quinones de triphenylphosphonium
HU188490B (en)	1986-04-28	Procedure for producing sulfhonated phenylphosphins
JPS6152085B2 (fr)	1986-11-12
CA1192574A (fr)	1985-08-27	Procede de preparation de triarylphosphines
US4661606A (en)	1987-04-28	Extraction of amino acids from aqueous mixtures and quaternary ammonium salt intermediates produced therein
HUP0204013A2 (en)	2003-04-28	Method for treating a reaction mixture containing a sulphinic acid salt whereof the bearing carbon sulphur is perfluorinated
FR2924116A1 (fr)	2009-05-29	Procede de preparation d'un sel de l'acide trifluoromethanesulfinique
US4623490A (en)	1986-11-18	Process for the purification of sulfonated aryl phosphines
Seto et al.	1991	Facile Preparation of Tetrabutylphosphonium Fluoride and Its HF Adducts. New Fluoride Anion Sources for Selective Nucleophilic Fluorination.
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US2588679A (en)	1952-03-11	Purification of gentisic acid
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JPH0210131B2 (fr)	1990-03-06
JPS6354342A (ja)	1988-03-08	（±）−α−エチルベンジルアミンの光学分割方法
JPH10120614A (ja)	1998-05-12	２−メチル−１，４−ナフトキノン亜硫酸水素塩の製造方法
JPH0977783A (ja)	1997-03-25	ジフェニルホスフィノベンゼン−ｍ−モノスルホン酸の精製法