DE1768656A1 - - Google Patents
Info
- Publication number
- DE1768656A1 DE1768656A1 DE19681768656 DE1768656A DE1768656A1 DE 1768656 A1 DE1768656 A1 DE 1768656A1 DE 19681768656 DE19681768656 DE 19681768656 DE 1768656 A DE1768656 A DE 1768656A DE 1768656 A1 DE1768656 A1 DE 1768656A1
- Authority
- DE
- Germany
- Prior art keywords
- neutral
- oxo
- acid
- diamino
- methyl alcohol
- 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.)
- Granted
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 186
- 230000007935 neutral effect Effects 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- DSSYKIVIOFKYAU-UHFFFAOYSA-N camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 235000005979 Citrus limon Nutrition 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- 244000248349 Citrus limon Species 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000002244 precipitate Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 13
- 238000000354 decomposition reaction Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000005263 alkylenediamine group Chemical group 0.000 description 3
- -1 amine salts Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 102100033070 Histone acetyltransferase KAT6B Human genes 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005700 Putrescine Substances 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-WFVSFCRTSA-N 1-deuteriobutane-1,4-diamine Chemical compound [2H]C(N)CCCN KIDHWZJUCRJVML-WFVSFCRTSA-N 0.000 description 1
- VHRGRCVQAFMJIZ-QYKNYGDISA-N 1-deuteriopentane-1,5-diamine Chemical compound NC(CCCCN)[2H] VHRGRCVQAFMJIZ-QYKNYGDISA-N 0.000 description 1
- XFNJVJPLKCPIBV-VMNATFBRSA-N 1-deuteriopropane-1,3-diamine Chemical compound NC(CCN)[2H] XFNJVJPLKCPIBV-VMNATFBRSA-N 0.000 description 1
- HVCCFMAPGCBCHZ-UHFFFAOYSA-N 2-aminoethylazanium;4-methylbenzenesulfonate Chemical compound NCCN.CC1=CC=C(S(O)(=O)=O)C=C1 HVCCFMAPGCBCHZ-UHFFFAOYSA-N 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 101000944174 Homo sapiens Histone acetyltransferase KAT6B Proteins 0.000 description 1
- 101100019690 Homo sapiens KAT6B gene Proteins 0.000 description 1
- PIICEJLVQHRZGT-JBISRTOLSA-N N,N,N',N'-tetradeuterioethane-1,2-diamine Chemical compound [2H]N([2H])CCN([2H])[2H] PIICEJLVQHRZGT-JBISRTOLSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- XZUAPPXGIFNDRA-UHFFFAOYSA-N ethane-1,2-diamine;hydrate Chemical compound O.NCCN XZUAPPXGIFNDRA-UHFFFAOYSA-N 0.000 description 1
- HODPISPVTPCXIU-UHFFFAOYSA-N ethane-1,2-diamine;nitric acid Chemical compound NCCN.O[N+]([O-])=O HODPISPVTPCXIU-UHFFFAOYSA-N 0.000 description 1
- LBYLJCBBENQUQF-UHFFFAOYSA-N hexane-1,6-diamine;4-methylbenzenesulfonic acid Chemical compound NCCCCCCN.CC1=CC=C(S(O)(=O)=O)C=C1 LBYLJCBBENQUQF-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- PIICEJLVQHRZGT-ZSJDYOACSA-N n,n'-dideuterioethane-1,2-diamine Chemical compound [2H]NCCN[2H] PIICEJLVQHRZGT-ZSJDYOACSA-N 0.000 description 1
- DDLUSQPEQUJVOY-UHFFFAOYSA-N nonane-1,1-diamine Chemical compound CCCCCCCCC(N)N DDLUSQPEQUJVOY-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010792 warming 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/265—Citric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/18—Saturated compounds containing keto groups
- C07C62/24—Saturated compounds containing keto groups the keto group being part of a ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2703067 | 1967-06-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1768656A1 true DE1768656A1 (enrdf_load_stackoverflow) | 1971-12-02 |
| DE1768656B2 DE1768656B2 (enrdf_load_stackoverflow) | 1974-01-24 |
| DE1768656C3 DE1768656C3 (enrdf_load_stackoverflow) | 1974-08-15 |
Family
ID=10253022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768656 Expired DE1768656C3 (enrdf_load_stackoverflow) | 1967-06-12 | 1968-06-12 |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE715739A (enrdf_load_stackoverflow) |
| CH (1) | CH481036A (enrdf_load_stackoverflow) |
| DE (1) | DE1768656C3 (enrdf_load_stackoverflow) |
| ES (1) | ES354887A1 (enrdf_load_stackoverflow) |
| FR (2) | FR1587351A (enrdf_load_stackoverflow) |
| GB (1) | GB1176077A (enrdf_load_stackoverflow) |
| NL (2) | NL6808261A (enrdf_load_stackoverflow) |
-
0
- NL NL131914D patent/NL131914C/xx active
-
1967
- 1967-06-12 GB GB27032/67A patent/GB1176077A/en not_active Expired
-
1968
- 1968-05-27 BE BE715739D patent/BE715739A/xx unknown
- 1968-05-27 CH CH780968A patent/CH481036A/fr not_active IP Right Cessation
- 1968-05-30 FR FR1587351D patent/FR1587351A/fr not_active Expired
- 1968-06-11 ES ES354887A patent/ES354887A1/es not_active Expired
- 1968-06-12 DE DE19681768656 patent/DE1768656C3/de not_active Expired
- 1968-06-12 NL NL6808261A patent/NL6808261A/xx unknown
- 1968-07-24 FR FR160342A patent/FR7959M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR7959M (enrdf_load_stackoverflow) | 1970-06-01 |
| NL6808261A (enrdf_load_stackoverflow) | 1968-12-13 |
| GB1176077A (en) | 1970-01-01 |
| DE1768656B2 (enrdf_load_stackoverflow) | 1974-01-24 |
| CH481036A (fr) | 1969-11-15 |
| FR1587351A (enrdf_load_stackoverflow) | 1970-03-20 |
| NL131914C (enrdf_load_stackoverflow) | |
| DE1768656C3 (enrdf_load_stackoverflow) | 1974-08-15 |
| BE715739A (enrdf_load_stackoverflow) | 1968-10-16 |
| ES354887A1 (es) | 1969-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |