DE2145656A1 - - Google Patents
Info
- Publication number
- DE2145656A1 DE2145656A1 DE19712145656 DE2145656A DE2145656A1 DE 2145656 A1 DE2145656 A1 DE 2145656A1 DE 19712145656 DE19712145656 DE 19712145656 DE 2145656 A DE2145656 A DE 2145656A DE 2145656 A1 DE2145656 A1 DE 2145656A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- aminoindane
- weight
- parts
- salts
- 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.)
- Pending
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 238000006277 sulfonation reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- VATQYKDHIHRVIN-UHFFFAOYSA-N 7-amino-2,3-dihydro-1h-indene-4,6-disulfonic acid Chemical class C1=C(S(O)(=O)=O)C(N)=C2CCCC2=C1S(O)(=O)=O VATQYKDHIHRVIN-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- IUOAMLUXPZNOEV-UHFFFAOYSA-N 7-amino-2,3-dihydro-1h-indene-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C2=C1CCC2 IUOAMLUXPZNOEV-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- -1 indane-4-sulfamic acid Chemical compound 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RXTJLDXSGNEJIT-UHFFFAOYSA-N 2,3-dihydro-1h-inden-4-amine Chemical compound NC1=CC=CC2=C1CCC2 RXTJLDXSGNEJIT-UHFFFAOYSA-N 0.000 description 1
- LEWZOBYWGWKNCK-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-amine Chemical compound NC1=CC=C2CCCC2=C1 LEWZOBYWGWKNCK-UHFFFAOYSA-N 0.000 description 1
- FWUGEWKTFZKYDP-UHFFFAOYSA-N 2,3-dihydro-1h-indene-4-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C1CCC2 FWUGEWKTFZKYDP-UHFFFAOYSA-N 0.000 description 1
- QTPUGPGPWPDKDV-UHFFFAOYSA-N 6-amino-2,3-dihydro-1h-indene-5-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC2=C1CCC2 QTPUGPGPWPDKDV-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/25—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton
- C07C309/26—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS714070A CS148603B1 (enrdf_load_stackoverflow) | 1970-10-23 | 1970-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2145656A1 true DE2145656A1 (enrdf_load_stackoverflow) | 1972-04-27 |
Family
ID=5419964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712145656 Pending DE2145656A1 (enrdf_load_stackoverflow) | 1970-10-23 | 1971-09-13 |
Country Status (8)
| Country | Link |
|---|---|
| AR (1) | AR193827A1 (enrdf_load_stackoverflow) |
| BR (1) | BR7106184D0 (enrdf_load_stackoverflow) |
| CH (1) | CH568969A5 (enrdf_load_stackoverflow) |
| CS (1) | CS148603B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2145656A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2113109A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1319230A (enrdf_load_stackoverflow) |
| IT (1) | IT945992B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199529A (en) * | 1977-10-03 | 1980-04-22 | Ciba-Geigy Ag | Process for the production of amino-I-acid |
-
1970
- 1970-10-23 CS CS714070A patent/CS148603B1/cs unknown
-
1971
- 1971-09-13 DE DE19712145656 patent/DE2145656A1/de active Pending
- 1971-09-16 GB GB4311171A patent/GB1319230A/en not_active Expired
- 1971-09-20 BR BR618471A patent/BR7106184D0/pt unknown
- 1971-09-21 AR AR23809271A patent/AR193827A1/es active
- 1971-09-23 CH CH1390171A patent/CH568969A5/xx not_active IP Right Cessation
- 1971-10-12 IT IT2978271A patent/IT945992B/it active
- 1971-10-22 FR FR7137997A patent/FR2113109A5/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199529A (en) * | 1977-10-03 | 1980-04-22 | Ciba-Geigy Ag | Process for the production of amino-I-acid |
Also Published As
| Publication number | Publication date |
|---|---|
| AR193827A1 (es) | 1973-05-31 |
| CH568969A5 (enrdf_load_stackoverflow) | 1975-11-14 |
| BR7106184D0 (pt) | 1973-04-12 |
| CS148603B1 (enrdf_load_stackoverflow) | 1973-03-29 |
| IT945992B (it) | 1973-05-10 |
| GB1319230A (en) | 1973-06-06 |
| FR2113109A5 (enrdf_load_stackoverflow) | 1972-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |