GB749138A - A process for the manufacture of organic electro-neutral salts from onium compounds - Google Patents
A process for the manufacture of organic electro-neutral salts from onium compoundsInfo
- Publication number
- GB749138A GB749138A GB34980/53A GB3498053A GB749138A GB 749138 A GB749138 A GB 749138A GB 34980/53 A GB34980/53 A GB 34980/53A GB 3498053 A GB3498053 A GB 3498053A GB 749138 A GB749138 A GB 749138A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ammonium
- trimethyl
- dimethyl
- pyridinium
- octadecyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000004010 onium ions Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- -1 butyl-hexyl Chemical group 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- OYLOMWZHERUMKP-UHFFFAOYSA-O 1-(2-aminophenyl)-2-(2-octadecylpyridin-1-ium-1-yl)ethanone Chemical compound C(CCCCCCCCCCCCCCCCC)C1=[N+](C=CC=C1)CC(=O)C=1C(N)=CC=CC1 OYLOMWZHERUMKP-UHFFFAOYSA-O 0.000 abstract 1
- FFYRIXSGFSWFAQ-UHFFFAOYSA-N 1-dodecylpyridin-1-ium Chemical class CCCCCCCCCCCC[N+]1=CC=CC=C1 FFYRIXSGFSWFAQ-UHFFFAOYSA-N 0.000 abstract 1
- AMKUSFIBHAUBIJ-UHFFFAOYSA-N 1-hexylpyridin-1-ium Chemical compound CCCCCC[N+]1=CC=CC=C1 AMKUSFIBHAUBIJ-UHFFFAOYSA-N 0.000 abstract 1
- KFCMWHHNUDCAQF-UHFFFAOYSA-N 1-hexylquinolin-1-ium Chemical compound C1=CC=C2[N+](CCCCCC)=CC=CC2=C1 KFCMWHHNUDCAQF-UHFFFAOYSA-N 0.000 abstract 1
- HIWVFNVUJDPDKS-UHFFFAOYSA-N 1-octadecylpyridin-1-ium Chemical compound CCCCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 HIWVFNVUJDPDKS-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- NHGUJZBRCSIJGV-UHFFFAOYSA-N N-(2-dodecylphenyl)sulfonylpropanamide Chemical compound C(CC)(=O)NS(=O)(=O)C1=C(C=CC=C1)CCCCCCCCCCCC NHGUJZBRCSIJGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003047 N-acetyl group Chemical group 0.000 abstract 1
- UMSTUOFEWCIVRZ-UHFFFAOYSA-N N-dodecylsulfonylbenzamide Chemical compound C(C1=CC=CC=C1)(=O)NS(=O)(=O)CCCCCCCCCCCC UMSTUOFEWCIVRZ-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 150000001495 arsenic compounds Chemical class 0.000 abstract 1
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical compound [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 abstract 1
- AHUPPLWJGMHWLU-UHFFFAOYSA-N benzyl-dimethyl-octadecylarsanium Chemical compound C(CCCCCCCCCCCCCCCCC)[As+](C)(C)CC1=CC=CC=C1 AHUPPLWJGMHWLU-UHFFFAOYSA-N 0.000 abstract 1
- VOYGFCXKIQYQOE-UHFFFAOYSA-N bis(2-dodecoxy-2-oxoethyl)-dimethylazanium Chemical compound CCCCCCCCCCCCOC(=O)C[N+](C)(C)CC(=O)OCCCCCCCCCCCC VOYGFCXKIQYQOE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- YYEHSNMITANNSX-UHFFFAOYSA-N cyclohexyl-dimethyl-octadecylazanium Chemical class CCCCCCCCCCCCCCCCCC[N+](C)(C)C1CCCCC1 YYEHSNMITANNSX-UHFFFAOYSA-N 0.000 abstract 1
- UQGUUNSLFLSUHZ-UHFFFAOYSA-N dimethyl(10-methylundecyl)sulfanium Chemical class C[S+](CCCCCCCCCC(C)C)C UQGUUNSLFLSUHZ-UHFFFAOYSA-N 0.000 abstract 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 abstract 1
- 229940073469 dimethyldodecylbenzylammonium Drugs 0.000 abstract 1
- QMQCMZCNAMHJAV-UHFFFAOYSA-N dodecoxymethyl(trimethyl)azanium Chemical compound CCCCCCCCCCCCOC[N+](C)(C)C QMQCMZCNAMHJAV-UHFFFAOYSA-N 0.000 abstract 1
- DSVZSFUFNYBSQL-UHFFFAOYSA-N dodecyl 2-pyridin-1-ium-1-ylacetate Chemical compound CCCCCCCCCCCCOC(=O)C[N+]1=CC=CC=C1 DSVZSFUFNYBSQL-UHFFFAOYSA-N 0.000 abstract 1
- MIQYOHNNWUEBSP-UHFFFAOYSA-N dodecyl(trimethyl)phosphanium Chemical compound CCCCCCCCCCCC[P+](C)(C)C MIQYOHNNWUEBSP-UHFFFAOYSA-N 0.000 abstract 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 abstract 1
- 229940093920 gynecological arsenic compound Drugs 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- XTPRURKTXNFVQT-UHFFFAOYSA-N hexyl(trimethyl)azanium Chemical compound CCCCCC[N+](C)(C)C XTPRURKTXNFVQT-UHFFFAOYSA-N 0.000 abstract 1
- YOTJLHLIQMEBTN-UHFFFAOYSA-N n-(benzenesulfonyl)naphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NS(=O)(=O)C1=CC=CC=C1 YOTJLHLIQMEBTN-UHFFFAOYSA-N 0.000 abstract 1
- NVUBFYYOVIBBBL-UHFFFAOYSA-O n-(pyridin-1-ium-1-ylmethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC[N+]1=CC=CC=C1 NVUBFYYOVIBBBL-UHFFFAOYSA-O 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- ADUYZJVDIRZWHQ-UHFFFAOYSA-O octadecyl N-(1-methylpyridin-1-ium-2-yl)carbamate Chemical compound C(CCCCCCCCCCCCCCCCC)OC(=O)NC1=[N+](C=CC=C1)C ADUYZJVDIRZWHQ-UHFFFAOYSA-O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- AFCCADLGTHSBSJ-UHFFFAOYSA-N triethyl(octadecylsulfanylmethyl)azanium Chemical compound CCCCCCCCCCCCCCCCCCSC[N+](CC)(CC)CC AFCCADLGTHSBSJ-UHFFFAOYSA-N 0.000 abstract 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 abstract 1
- YZRVTWRPCLHSRW-UHFFFAOYSA-N trimethyl-(2-octadecoxy-2-oxoethyl)azanium Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C[N+](C)(C)C YZRVTWRPCLHSRW-UHFFFAOYSA-N 0.000 abstract 1
- GCDMABRJAZAKOP-UHFFFAOYSA-O trimethyl-[2-(octadecylamino)-2-oxoethyl]azanium Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C[N+](C)(C)C GCDMABRJAZAKOP-UHFFFAOYSA-O 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Neutral salts are obtained by reacting water-soluble salts of disulphonimides or N-acyl-sulphonamides with quaternary ammonium, phosphonium or arsonium or ternary sulphonium salts having attached to the central atom a radical or 6 or more carbon atoms. The latter radical may be alkyl, cycloalkyl or aralkyl and the chain may be interrupted by hetero-atoms such as oxygen, sulphur or nitrogen, and may contain substituents. The radicals attached to the sulphonimide or acylsulphonamide groups may be alkyl, cycloalkyl, aralkyl or aryl and may be substituted or interrupted as above. Examples show the preparation of (1) dodecyl-pyridinium salt of dioctadecyl-disulphonimide; (2) dimethyl-cyclohexyl-octadecyl-ammonium salt of ditolyl-disulphonimide; and (3) dimethyl-isododecyl-sulphonium salt of di-p-tolyl-disulphonimide. Other suitable cations are trimethyl - hexyl - ammonium, trimethyl-dodecyl - ammonium, trimethyl - octadecyl-ammonium, dimethyl - dioctadecyl - ammonium, dimethyl - dodecyl - benzyl - ammonium, hexylpyridinium, hexylquinolinium, octadecyl-pyridinium, octadecoxy - carbonylmethyl - trimethyl - ammonium, dodecoxycarbonylmethyl-pyridinium, naphthenoxycarbonylmethyl - quinolinium, abietyloxycarbonylmethyl - quinolinium, di - (dodecoxycarbonylmethyl) - dimethyl - ammonium, octadecylamino - carbonylmethyl - trimethyl - ammonium, octadecylanilino - carbonylmethyl - pyridinium, dodecoxymethyl - trimethyl - ammonium, octadecylthiomethyl - triethyl - ammonium, stearoylaminomethyl - pyridinium, octadecoxy-carbonylamino - methyl - pyridinium and the corresponding phosphorus and arsenic compounds, e.g. dodecyl-trimethyl-phosphonium and octadecyl - benzyl - dimethyl - arsonium; these compounds can contain further oniom groups. Other suitable sulphonamide derivatives are butyl-hexyl, dioctyl, octyl-octadecyl, cyclohexyl - dodecyl, di - alkylphenyl (C6-C18 alkyl) and dinaphthyl disulphonimides, and N-acetyl, N-isobutyryl, N-lauroyl and N-naphthoyl - benzenesulphonamide, N - propionyl-dodecylbenzenesulphonamide and N - benzoyl-laurylsulphonamide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE749138X | 1952-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB749138A true GB749138A (en) | 1956-05-16 |
Family
ID=6649194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34980/53A Expired GB749138A (en) | 1952-12-18 | 1953-12-16 | A process for the manufacture of organic electro-neutral salts from onium compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB749138A (en) |
-
1953
- 1953-12-16 GB GB34980/53A patent/GB749138A/en not_active Expired
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