PL84916B1 - - Google Patents
Download PDFInfo
- Publication number
- PL84916B1 PL84916B1 PL1972157013A PL15701372A PL84916B1 PL 84916 B1 PL84916 B1 PL 84916B1 PL 1972157013 A PL1972157013 A PL 1972157013A PL 15701372 A PL15701372 A PL 15701372A PL 84916 B1 PL84916 B1 PL 84916B1
- Authority
- PL
- Poland
- Prior art keywords
- copper
- catalyst
- oxygen
- reactions
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- -1 nitrogen-containing organic bases Chemical class 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001879 copper Chemical class 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 239000005749 Copper compound Substances 0.000 claims 3
- 150000001880 copper compounds Chemical class 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- ORXJJKCQWLBLFE-UHFFFAOYSA-N azane;butyl hydrogen sulfate Chemical compound [NH4+].CCCCOS([O-])(=O)=O ORXJJKCQWLBLFE-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2701371 | 1971-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL84916B1 true PL84916B1 (d) | 1976-04-30 |
Family
ID=11220764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972157013A PL84916B1 (d) | 1971-07-31 | 1972-07-29 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3829457A (d) |
| JP (1) | JPS543854B1 (d) |
| AT (1) | AT318552B (d) |
| BE (1) | BE786618A (d) |
| CA (1) | CA983514A (d) |
| CH (1) | CH551390A (d) |
| CS (1) | CS164781B2 (d) |
| DD (1) | DD100463A5 (d) |
| DE (1) | DE2235916A1 (d) |
| FR (1) | FR2149108A5 (d) |
| GB (1) | GB1382509A (d) |
| LU (1) | LU65794A1 (d) |
| NL (1) | NL7210413A (d) |
| PL (1) | PL84916B1 (d) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4042668A (en) * | 1975-10-15 | 1977-08-16 | E. I. Du Pont De Nemours And Company | SO2 removal process |
| JPS5984314U (ja) * | 1982-11-26 | 1984-06-07 | 東京瓦斯株式会社 | フアンコンベクタ− |
-
0
- BE BE786618D patent/BE786618A/xx unknown
-
1972
- 1972-07-13 CS CS4988A patent/CS164781B2/cs unknown
- 1972-07-19 GB GB3385772A patent/GB1382509A/en not_active Expired
- 1972-07-21 DE DE2235916A patent/DE2235916A1/de not_active Withdrawn
- 1972-07-24 CA CA147,810A patent/CA983514A/en not_active Expired
- 1972-07-24 CH CH1103172A patent/CH551390A/fr not_active IP Right Cessation
- 1972-07-26 DD DD164690A patent/DD100463A5/xx unknown
- 1972-07-26 FR FR7226805A patent/FR2149108A5/fr not_active Expired
- 1972-07-26 LU LU65794D patent/LU65794A1/xx unknown
- 1972-07-28 NL NL7210413A patent/NL7210413A/xx not_active Application Discontinuation
- 1972-07-28 AT AT652472A patent/AT318552B/de not_active IP Right Cessation
- 1972-07-29 PL PL1972157013A patent/PL84916B1/pl unknown
- 1972-07-31 US US00276466A patent/US3829457A/en not_active Expired - Lifetime
- 1972-07-31 JP JP7605172A patent/JPS543854B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3829457A (en) | 1974-08-13 |
| AT318552B (de) | 1974-10-25 |
| CS164781B2 (d) | 1975-11-28 |
| CA983514A (en) | 1976-02-10 |
| DD100463A5 (d) | 1973-09-20 |
| DE2235916A1 (de) | 1973-02-08 |
| CH551390A (fr) | 1974-07-15 |
| LU65794A1 (d) | 1972-11-28 |
| BE786618A (fr) | 1973-01-24 |
| GB1382509A (en) | 1975-02-05 |
| NL7210413A (d) | 1973-02-02 |
| JPS543854B1 (d) | 1979-02-27 |
| FR2149108A5 (d) | 1973-03-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3424694A (en) | Mixture of surface-active compounds and process for preparing same | |
| KR940005651A (ko) | 3,4-디메틸-2,5,6-트리스(p-설포네이토페닐)-1-포스파노르보르나디엔, 이의 제조방법 및 올레핀계 불포화 화합물의 하이드로포닐화 방법 | |
| US2704295A (en) | Aromatic hydrocarbon sulfonation | |
| Huang et al. | Studies on deiodo-sulfination. Part I. Studies on the deiodo-sulfination of perfluoroalkyl iodides | |
| US3029264A (en) | Preparation of a mixture of fattyacyl-oxyalkane sulphonates | |
| PL84916B1 (d) | ||
| GB1012944A (en) | ª‰-hydroxy-alkane-ª‡-sulphonic anhydrides and secondary products thereof, and a process for their manufacture | |
| US2868812A (en) | Manufacture of fatty acid monoesters of glycerol monosulfuric acid and salts thereof | |
| US2854476A (en) | Method of sulfonation with a sulfur trioxide addition product | |
| JPH0128745B2 (d) | ||
| US1475158A (en) | Process of making artificial cryolite | |
| EP0599385B1 (en) | Process for preparing sulfonated paraffins with a larger content of polysulfonated species | |
| CN111717901B (zh) | 一种利用酸酐-水系制备双（氟磺酰）亚胺的方法 | |
| ES407538A1 (es) | Procedimiento para preparar un producto de reaccion organi-co sulfonado soluble en agua. | |
| Saegusa et al. | Synthetic reactions by complex catalysts. XVII. Copper-catalyzed reaction of azide with thiol | |
| US3885024A (en) | Process for the preparation of pyrosulphates | |
| US2098114A (en) | Process for sulphonating alcohols | |
| US3275681A (en) | Catalytic system for the addition of bisulfites to olefins | |
| JPS57109773A (en) | Manufacture of saccharin | |
| US2559585A (en) | Preparation of sulfonic acid compounds | |
| US3829470A (en) | Alkylphenol disulfonation process | |
| US744720A (en) | Process of desulfurizing sulfur-bearing petroleum. | |
| US2742484A (en) | beta-sulfonation of anthraquinone containing mercury | |
| US3636090A (en) | Sulfonation of benzene under superatmospheric pressure | |
| US2697117A (en) | Sulfonation of benzene |