NO129344B - - Google Patents
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- Publication number
- NO129344B NO129344B NO00751/68A NO75168A NO129344B NO 129344 B NO129344 B NO 129344B NO 00751/68 A NO00751/68 A NO 00751/68A NO 75168 A NO75168 A NO 75168A NO 129344 B NO129344 B NO 129344B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- hydrogen peroxide
- reaction medium
- alkanesulfonic
- methanesulfonic acid
- Prior art date
Links
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 82
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 77
- 239000002253 acid Substances 0.000 claims description 46
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 38
- 239000012429 reaction media Substances 0.000 claims description 26
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 150000007513 acids Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 150000004965 peroxy acids Chemical class 0.000 claims description 15
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 claims description 13
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- -1 alkyl mercaptans Chemical class 0.000 claims description 7
- KXEMXOYVVPLGSD-UHFFFAOYSA-N benzene-1,3-dicarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC(C(=O)OO)=C1 KXEMXOYVVPLGSD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 150000004967 organic peroxy acids Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 238000005502 peroxidation Methods 0.000 description 4
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000306 component Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002019 disulfides Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CUDSBWGCGSUXDB-UHFFFAOYSA-N Dibutyl disulfide Chemical class CCCCSSCCCC CUDSBWGCGSUXDB-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical class CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical group CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61957667A | 1967-03-01 | 1967-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129344B true NO129344B (fr) | 1974-04-01 |
Family
ID=24482468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00751/68A NO129344B (fr) | 1967-03-01 | 1968-02-29 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3509206A (fr) |
| CH (1) | CH484041A (fr) |
| DE (1) | DE1668585B2 (fr) |
| DK (1) | DK128605B (fr) |
| FR (1) | FR1556567A (fr) |
| GB (1) | GB1171273A (fr) |
| NL (1) | NL6802005A (fr) |
| NO (1) | NO129344B (fr) |
| SE (1) | SE358150B (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2504235C3 (de) * | 1975-02-01 | 1979-04-19 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von Alkylsulfonsäuren |
| US4035242A (en) * | 1975-09-29 | 1977-07-12 | Ppg Industries, Inc. | Distillative purification of alkane sulfonic acids |
| US4450047A (en) * | 1983-01-28 | 1984-05-22 | Penwalt Corporation | Process for recovering anhydrous alkanesulfonic acids by reduced pressure, falling film evaporation |
| US4938846A (en) * | 1986-12-08 | 1990-07-03 | Atochem, North America, Inc. | Preparation of anhydrous alkanesulfonic acid |
| US4956494A (en) * | 1987-10-26 | 1990-09-11 | Pennwalt Corporation | Oxidation of thiols, disulfides and thiolsulfonates |
| US5127837A (en) * | 1989-06-09 | 1992-07-07 | Labinal Components And Systems, Inc. | Electrical connectors and IC chip tester embodying same |
| US5485351A (en) * | 1989-06-09 | 1996-01-16 | Labinal Components And Systems, Inc. | Socket assembly for integrated circuit chip package |
| DE10297842T5 (de) * | 2002-12-27 | 2005-10-27 | Council Of Scientific And Industrial Research | Verfahren zur Herstellung von Alkansulfonsäure |
| CA3074198A1 (fr) * | 2020-02-28 | 2021-08-28 | Fluid Energy Group Ltd. | Acide methanesulfonique modifie et utilisations connexes |
| CA3074199A1 (fr) | 2020-02-28 | 2021-08-28 | Fluid Energy Group Ltd. | Acide sulfurique modifie et utilisations connexes |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB522840A (en) * | 1937-12-18 | 1940-06-28 | Du Pont | Manufacture of surface-active compounds |
| US2667507A (en) * | 1950-08-31 | 1954-01-26 | Celanese Corp | Preparation of disulfonic acids |
| USB61008I5 (fr) * | 1958-04-03 | |||
| US3143562A (en) * | 1961-03-27 | 1964-08-04 | Leonard S Silbert | Preparation of aromatic peroxy acids |
| US3079411A (en) * | 1961-04-24 | 1963-02-26 | Leonard S Silbert | Preparation of long-chain aliphatic peroxy acids |
-
1967
- 1967-03-01 US US619576A patent/US3509206A/en not_active Expired - Lifetime
-
1968
- 1968-02-13 NL NL6802005A patent/NL6802005A/xx unknown
- 1968-02-17 DE DE1668585A patent/DE1668585B2/de active Granted
- 1968-02-21 CH CH252268A patent/CH484041A/fr not_active IP Right Cessation
- 1968-02-26 FR FR141245A patent/FR1556567A/fr not_active Expired
- 1968-02-28 SE SE02591/68A patent/SE358150B/xx unknown
- 1968-02-29 DK DK80168AA patent/DK128605B/da unknown
- 1968-02-29 NO NO00751/68A patent/NO129344B/no unknown
- 1968-02-29 GB GB9760/68A patent/GB1171273A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1556567A (fr) | 1969-02-07 |
| US3509206A (en) | 1970-04-28 |
| DE1668585A1 (de) | 1971-06-03 |
| NL6802005A (fr) | 1968-09-02 |
| CH484041A (fr) | 1970-01-15 |
| DE1668585B2 (de) | 1975-11-13 |
| SE358150B (fr) | 1973-07-23 |
| DK128605B (da) | 1974-06-04 |
| GB1171273A (en) | 1969-11-19 |
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