NO162258B - Fremgangsm te for fremstilling av nitrogengass. - Google Patents
Fremgangsm te for fremstilling av nitrogengass. Download PDFInfo
- Publication number
- NO162258B NO162258B NO834422A NO834422A NO162258B NO 162258 B NO162258 B NO 162258B NO 834422 A NO834422 A NO 834422A NO 834422 A NO834422 A NO 834422A NO 162258 B NO162258 B NO 162258B
- Authority
- NO
- Norway
- Prior art keywords
- bis
- parts
- yloxy
- analysis
- carboxychromon
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- 238000002360 preparation method Methods 0.000 title description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title description 3
- 229910001873 dinitrogen Inorganic materials 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 43
- -1 alkali metal salts Chemical class 0.000 claims description 40
- 150000002148 esters Chemical class 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 150000002118 epoxides Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000003944 halohydrins Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 199
- 238000004458 analytical method Methods 0.000 description 94
- 239000000243 solution Substances 0.000 description 55
- 239000000203 mixture Substances 0.000 description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 238000002425 crystallisation Methods 0.000 description 45
- 230000008025 crystallization Effects 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 28
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 26
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- YPTJKHVBDCRKNF-UHFFFAOYSA-N 2',6'-Dihydroxyacetophenone Chemical compound CC(=O)C1=C(O)C=CC=C1O YPTJKHVBDCRKNF-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 239000003921 oil Substances 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- 238000010992 reflux Methods 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 208000006673 asthma Diseases 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 9
- RVMGXWBCQGAWBR-UHFFFAOYSA-N 4-oxo-1-benzopyran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC(=O)C2=C1 RVMGXWBCQGAWBR-UHFFFAOYSA-N 0.000 description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 125000005594 diketone group Chemical class 0.000 description 9
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000000427 antigen Substances 0.000 description 8
- 102000036639 antigens Human genes 0.000 description 8
- 108091007433 antigens Proteins 0.000 description 8
- 150000004682 monohydrates Chemical class 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 229940126062 Compound A Drugs 0.000 description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- MOWNIAOVRQFQEF-UHFFFAOYSA-N 1-[2-[5-(2-acetyl-3-hydroxyphenoxy)pentoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O MOWNIAOVRQFQEF-UHFFFAOYSA-N 0.000 description 4
- WOLDEHWWZNMZJV-UHFFFAOYSA-N 5-[4-(2-carboxy-4-oxochromen-5-yl)oxybutoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 WOLDEHWWZNMZJV-UHFFFAOYSA-N 0.000 description 4
- ILAZSBMAIJXODQ-UHFFFAOYSA-N 5-[5-(2-carboxy-4-oxochromen-5-yl)oxypentoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 ILAZSBMAIJXODQ-UHFFFAOYSA-N 0.000 description 4
- NWTNHOSYXTWRQT-UHFFFAOYSA-N 6-[5-(2-carboxy-4-oxochromen-6-yl)oxypentoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=CC(OCCCCCOC=3C=C4C(=O)C=C(OC4=CC=3)C(=O)O)=CC=C21 NWTNHOSYXTWRQT-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229940124630 bronchodilator Drugs 0.000 description 4
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- UILPJVPSNHJFIK-UHFFFAOYSA-N p-methoxy-o-hydroxyacetophenone Natural products COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- BVFXPYVNONOIOL-UHFFFAOYSA-N 1-[2-[3-(2-acetyl-3-hydroxyphenoxy)propoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O BVFXPYVNONOIOL-UHFFFAOYSA-N 0.000 description 3
- DBHSMAKQPAAGPD-UHFFFAOYSA-N 1-[2-[4-(2-acetyl-3-hydroxyphenoxy)butoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O DBHSMAKQPAAGPD-UHFFFAOYSA-N 0.000 description 3
- YKZNLYQRDOZDKJ-UHFFFAOYSA-N 1-[4-[3-(2-acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]-2-hydroxyphenyl]ethanone Chemical compound CC(=O)C1=C(O)C=C(OCC(O)COC2=C(C(C)=O)C(O)=CC=C2)C=C1 YKZNLYQRDOZDKJ-UHFFFAOYSA-N 0.000 description 3
- XZJQYCIBJLLOEK-UHFFFAOYSA-N 2-methyl-5-[5-(2-methyl-4-oxochromen-5-yl)oxypentoxy]chromen-4-one Chemical compound CC=1OC2=CC=CC(=C2C(C1)=O)OCCCCCOC1=C2C(C=C(OC2=CC=C1)C)=O XZJQYCIBJLLOEK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 201000009961 allergic asthma Diseases 0.000 description 3
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 3
- 150000004683 dihydrates Chemical class 0.000 description 3
- JLIKLEGJFLYMAX-UHFFFAOYSA-N ethyl 7-[3-(2-ethoxycarbonyl-4-oxochromen-7-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylate Chemical compound C(C)OC(=O)C=1OC2=CC(=CC=C2C(C1)=O)OCC(COC1=CC=C2C(C=C(OC2=C1)C(=O)OCC)=O)O JLIKLEGJFLYMAX-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- AHQTYUNPLZYCOL-UHFFFAOYSA-N 1,4-dioxane;ethanol;hydrate Chemical compound O.CCO.C1COCCO1 AHQTYUNPLZYCOL-UHFFFAOYSA-N 0.000 description 2
- KMTLZBUHQPQFAV-UHFFFAOYSA-N 1-(2,4-dihydroxy-3-methylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(O)C(C)=C1O KMTLZBUHQPQFAV-UHFFFAOYSA-N 0.000 description 2
- KTQBMKQANYHTMS-UHFFFAOYSA-N 1-[6-[3-(2-acetyl-4-ethyl-3-hydroxyphenoxy)-2-hydroxypropoxy]-3-ethyl-2-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCC(COC2=C(C(=C(C=C2)CC)O)C(C)=O)O)C=CC(=C1O)CC KTQBMKQANYHTMS-UHFFFAOYSA-N 0.000 description 2
- WLDWSGZHNBANIO-UHFFFAOYSA-N 2',5'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC(O)=CC=C1O WLDWSGZHNBANIO-UHFFFAOYSA-N 0.000 description 2
- CVFFLNSOIOGOFJ-UHFFFAOYSA-N 4-[5-(4-hydroxyphenoxy)pentoxy]phenol Chemical compound C1=CC(O)=CC=C1OCCCCCOC1=CC=C(O)C=C1 CVFFLNSOIOGOFJ-UHFFFAOYSA-N 0.000 description 2
- ZSLZPIBPJOBWGH-UHFFFAOYSA-N 5-[4-(2-carboxy-4-oxochromen-5-yl)oxy-3-hydroxybutoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)CCOC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 ZSLZPIBPJOBWGH-UHFFFAOYSA-N 0.000 description 2
- DWCCSURARIZGPH-UHFFFAOYSA-N 5-[4-(2-carboxy-4-oxochromen-5-yl)oxybut-2-enoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC=CCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 DWCCSURARIZGPH-UHFFFAOYSA-N 0.000 description 2
- JGEDRLGZWQLVNQ-UHFFFAOYSA-N 5-[5-[4-oxo-2-(2-phenylethenyl)chromen-5-yl]oxypentoxy]-2-(2-phenylethenyl)chromen-4-one Chemical compound C(=CC1=CC=CC=C1)C=1OC2=CC=CC(=C2C(C1)=O)OCCCCCOC1=C2C(C=C(OC2=CC=C1)C=CC1=CC=CC=C1)=O JGEDRLGZWQLVNQ-UHFFFAOYSA-N 0.000 description 2
- QGEKJPVUUYFRQV-UHFFFAOYSA-N 5-[6-(2-carboxy-4-oxochromen-5-yl)oxyhexoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 QGEKJPVUUYFRQV-UHFFFAOYSA-N 0.000 description 2
- MWQUUYDICQWXQT-UHFFFAOYSA-N 5-[[5-[(2-carboxy-4-oxochromen-5-yl)oxymethyl]-1,4-dioxan-2-yl]methoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(CO1)OCC1COC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 MWQUUYDICQWXQT-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 208000024711 extrinsic asthma Diseases 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 201000010659 intrinsic asthma Diseases 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004199 lung function Effects 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N (-)-(2R,3R)--2,3-butanediol Natural products CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- RMXLHIUHKIVPAB-OWOJBTEDSA-N (e)-1,4-dibromobut-2-ene Chemical compound BrC\C=C\CBr RMXLHIUHKIVPAB-OWOJBTEDSA-N 0.000 description 1
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- KIHQZLPHVZKELA-UHFFFAOYSA-N 1,3-dibromopropan-2-ol Chemical compound BrCC(O)CBr KIHQZLPHVZKELA-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- YDPZWUMQKMLLHC-UHFFFAOYSA-N 1,5-dibromo-3-methylpentane Chemical compound BrCCC(C)CCBr YDPZWUMQKMLLHC-UHFFFAOYSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- WGAXVZXBFBHLMC-UHFFFAOYSA-N 1,9-dibromononane Chemical compound BrCCCCCCCCCBr WGAXVZXBFBHLMC-UHFFFAOYSA-N 0.000 description 1
- JLKWVASSCBEYTE-UHFFFAOYSA-N 1-(2-hydroxy-6-phenylmethoxyphenyl)ethanone Chemical compound CC(=O)C1=C(O)C=CC=C1OCC1=CC=CC=C1 JLKWVASSCBEYTE-UHFFFAOYSA-N 0.000 description 1
- HZRXQORWKLUXON-UHFFFAOYSA-N 1-[2-[10-(2-acetyl-3-hydroxyphenoxy)decoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCCCCCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O HZRXQORWKLUXON-UHFFFAOYSA-N 0.000 description 1
- NJVPTKGHZHFFNU-UHFFFAOYSA-N 1-[2-[2-[2-(2-acetyl-3-hydroxyphenoxy)ethoxy]ethoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCOCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O NJVPTKGHZHFFNU-UHFFFAOYSA-N 0.000 description 1
- ABODFBBBEONILP-UHFFFAOYSA-N 1-[2-[3-(2-acetyl-3-hydroxy-5-methylphenoxy)-2-hydroxypropoxy]-6-hydroxy-4-methylphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCC(COC2=C(C(=CC(=C2)C)O)C(C)=O)O)C=C(C=C1O)C ABODFBBBEONILP-UHFFFAOYSA-N 0.000 description 1
- RUOPAUDVYRHXDB-UHFFFAOYSA-N 1-[2-[3-(2-acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]-6-hydroxyphenyl]ethanone Chemical compound CC(=O)C1=C(O)C=CC=C1OCC(O)COC1=CC=CC(O)=C1C(C)=O RUOPAUDVYRHXDB-UHFFFAOYSA-N 0.000 description 1
- WODXTRFWFHXFBY-UHFFFAOYSA-N 1-[2-[3-[4-[3-(2-acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]butoxy]-2-hydroxypropoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCC(COCCCCOCC(COC2=C(C(=CC=C2)O)C(C)=O)O)O)C=CC=C1O WODXTRFWFHXFBY-UHFFFAOYSA-N 0.000 description 1
- GFAKTUHTZUEQCW-UHFFFAOYSA-N 1-[2-[4-(2-acetyl-3-hydroxyphenoxy)-2,3-dihydroxybutoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCC(C(COC2=C(C(=CC=C2)O)C(C)=O)O)O)C=CC=C1O GFAKTUHTZUEQCW-UHFFFAOYSA-N 0.000 description 1
- UXFAEGVEUKEWIE-UHFFFAOYSA-N 1-[2-[4-(2-acetyl-3-hydroxyphenoxy)-3-hydroxybutoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCC(CCOC2=C(C(=CC=C2)O)C(C)=O)O)C=CC=C1O UXFAEGVEUKEWIE-UHFFFAOYSA-N 0.000 description 1
- DHUTWEOFUONKPW-UHFFFAOYSA-N 1-[2-[4-(2-acetyl-3-hydroxyphenoxy)but-2-enoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCC=CCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O DHUTWEOFUONKPW-UHFFFAOYSA-N 0.000 description 1
- HYAKHWCGKYFHJH-UHFFFAOYSA-N 1-[2-[6-(2-acetyl-3-hydroxyphenoxy)hexoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O HYAKHWCGKYFHJH-UHFFFAOYSA-N 0.000 description 1
- RETSSCCWYGMQNJ-UHFFFAOYSA-N 1-[2-[8-(2-acetyl-3-hydroxyphenoxy)octoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCCCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O RETSSCCWYGMQNJ-UHFFFAOYSA-N 0.000 description 1
- OJUJWTNLGAHPCS-UHFFFAOYSA-N 1-[2-[9-(2-acetyl-3-hydroxyphenoxy)nonoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCCCCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O OJUJWTNLGAHPCS-UHFFFAOYSA-N 0.000 description 1
- VXIVGWAODZXIGV-UHFFFAOYSA-N 1-[3-[5-(3-acetyl-2-hydroxyphenoxy)pentoxy]-2-hydroxyphenyl]ethanone Chemical compound OC1=C(OCCCCCOC2=C(C(=CC=C2)C(C)=O)O)C=CC=C1C(C)=O VXIVGWAODZXIGV-UHFFFAOYSA-N 0.000 description 1
- RAXQXYOYPVVELW-UHFFFAOYSA-N 1-[4-[3-(4-acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]-2-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(C=C(OCC(COC2=CC(=C(C=C2)C(C)=O)O)O)C=C1)O RAXQXYOYPVVELW-UHFFFAOYSA-N 0.000 description 1
- SDMVIQZFCIDENA-UHFFFAOYSA-N 1-[4-[5-(2-acetyl-3-hydroxyphenoxy)pentoxy]-2-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCCOC2=CC(=C(C=C2)C(C)=O)O)C=CC=C1O SDMVIQZFCIDENA-UHFFFAOYSA-N 0.000 description 1
- FTKNPBOFLURTAB-UHFFFAOYSA-N 1-[4-[5-(4-acetyl-3-hydroxy-2-methylphenoxy)pentoxy]-2-hydroxy-3-methylphenyl]ethanone Chemical compound C(C)(=O)C1=C(C(=C(OCCCCCOC2=C(C(=C(C=C2)C(C)=O)O)C)C=C1)C)O FTKNPBOFLURTAB-UHFFFAOYSA-N 0.000 description 1
- WAGMAFWJACUTOU-UHFFFAOYSA-N 1-[5-[3-(3-acetyl-4-hydroxyphenoxy)-2-hydroxypropoxy]-2-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C=1C=C(OCC(COC2=CC(=C(C=C2)O)C(C)=O)O)C=CC=1O WAGMAFWJACUTOU-UHFFFAOYSA-N 0.000 description 1
- RGIKUBHWNPSGLD-UHFFFAOYSA-N 1-[5-[5-(3-acetyl-4-hydroxyphenoxy)pentoxy]-2-hydroxyphenyl]ethanone Chemical compound C1=C(O)C(C(=O)C)=CC(OCCCCCOC=2C=C(C(O)=CC=2)C(C)=O)=C1 RGIKUBHWNPSGLD-UHFFFAOYSA-N 0.000 description 1
- FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-UHFFFAOYSA-N 0.000 description 1
- HEJLFBLJYFSKCE-UHFFFAOYSA-N 2',3'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1O HEJLFBLJYFSKCE-UHFFFAOYSA-N 0.000 description 1
- UJGCDSJISZRBPO-UHFFFAOYSA-N 2,5-bis(iodomethyl)-1,4-dioxane Chemical compound ICC1COC(CI)CO1 UJGCDSJISZRBPO-UHFFFAOYSA-N 0.000 description 1
- ZKODPGZNBMIZFX-UHFFFAOYSA-N 2-(2-bromoethyl)oxirane Chemical compound BrCCC1CO1 ZKODPGZNBMIZFX-UHFFFAOYSA-N 0.000 description 1
- LSTAHPMLLDYWKN-UHFFFAOYSA-N 2-(2-phenylethenyl)chromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C=C1C=CC1=CC=CC=C1 LSTAHPMLLDYWKN-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- ONHNMNPBYPHXOQ-UHFFFAOYSA-N 2-ethyl-7-hydroxychromen-4-one Chemical compound C1=C(O)C=C2OC(CC)=CC(=O)C2=C1 ONHNMNPBYPHXOQ-UHFFFAOYSA-N 0.000 description 1
- JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 description 1
- PXPNSQMWVPLERM-UHFFFAOYSA-N 2-methylchromen-4-one Chemical compound C1=CC=C2OC(C)=CC(=O)C2=C1 PXPNSQMWVPLERM-UHFFFAOYSA-N 0.000 description 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 1
- HQARDVLSJLCFBA-UHFFFAOYSA-N 4-[(4-aminophenyl)carbamoyl]-1h-imidazole-5-carboxylic acid Chemical compound C1=CC(N)=CC=C1NC(=O)C1=C(C(O)=O)NC=N1 HQARDVLSJLCFBA-UHFFFAOYSA-N 0.000 description 1
- PIYVGPKPVKCJMQ-UHFFFAOYSA-N 4-ethoxybutan-2-ol Chemical compound CCOCCC(C)O PIYVGPKPVKCJMQ-UHFFFAOYSA-N 0.000 description 1
- YWCWFCGAVJLTIG-UHFFFAOYSA-N 4-oxo-7-pentoxychromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C=2C1=CC(OCCCCC)=CC=2 YWCWFCGAVJLTIG-UHFFFAOYSA-N 0.000 description 1
- YIHPBFNJUANWMM-UHFFFAOYSA-N 5-[10-(2-carboxy-4-oxochromen-5-yl)oxydecoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCCCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 YIHPBFNJUANWMM-UHFFFAOYSA-N 0.000 description 1
- LMHNIXHQAJSZRY-UHFFFAOYSA-N 5-[2-(2-carboxy-4-oxochromen-5-yl)oxyethoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 LMHNIXHQAJSZRY-UHFFFAOYSA-N 0.000 description 1
- BOKHYMYGCSEGBS-UHFFFAOYSA-N 5-[2-[(2-carboxy-4-oxochromen-5-yl)oxymethyl]-2-(chloromethyl)-3-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(CCl)(CO)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 BOKHYMYGCSEGBS-UHFFFAOYSA-N 0.000 description 1
- MPAJUPGHFOZQQT-UHFFFAOYSA-N 5-[2-[2-(2-carboxy-4-oxochromen-5-yl)oxyethoxy]ethoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCOCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 MPAJUPGHFOZQQT-UHFFFAOYSA-N 0.000 description 1
- SABHRJWWKKNPBL-UHFFFAOYSA-N 5-[2-[4-[2-(2-carboxy-4-oxochromen-5-yl)oxyethoxy]-4-oxobutanoyl]oxyethoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCOC(=O)CCC(=O)OCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 SABHRJWWKKNPBL-UHFFFAOYSA-N 0.000 description 1
- UFLSTJXYPWYBNW-UHFFFAOYSA-N 5-[3-(2-carboxy-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]-8-ethyl-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(CC)=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 UFLSTJXYPWYBNW-UHFFFAOYSA-N 0.000 description 1
- VCMVCAJFRCBVDQ-UHFFFAOYSA-N 5-[3-(2-carboxy-4-oxochromen-7-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 VCMVCAJFRCBVDQ-UHFFFAOYSA-N 0.000 description 1
- HFLIWEXGJQBGCI-UHFFFAOYSA-N 5-[3-(2-carboxy-7-methyl-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]-7-methyl-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C=2C1=CC(C)=CC=2OCC(O)COC1=CC(C)=CC2=C1C(=O)C=C(C(O)=O)O2 HFLIWEXGJQBGCI-UHFFFAOYSA-N 0.000 description 1
- AXUTXGIRPNCGIH-UHFFFAOYSA-N 5-[3-(2-carboxy-8-ethyl-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]-8-ethyl-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(CC)=CC=C2OCC(O)COC1=CC=C(CC)C2=C1C(=O)C=C(C(O)=O)O2 AXUTXGIRPNCGIH-UHFFFAOYSA-N 0.000 description 1
- ASZBKZRJBISSAR-UHFFFAOYSA-N 5-[3-[3-(2-carboxy-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 ASZBKZRJBISSAR-UHFFFAOYSA-N 0.000 description 1
- NQMCHRKBRSYHAM-UHFFFAOYSA-N 5-[3-[4-[3-(2-carboxy-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]butoxy]-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COCCCCOCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 NQMCHRKBRSYHAM-UHFFFAOYSA-N 0.000 description 1
- UXTDVBFZKFGSIM-UHFFFAOYSA-N 5-[4-(2-carboxy-4-oxochromen-5-yl)oxy-2,3-dihydroxybutoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)C(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 UXTDVBFZKFGSIM-UHFFFAOYSA-N 0.000 description 1
- KLHNFEIYXZFYEF-UHFFFAOYSA-N 5-[5-(2-carboxy-4-oxochromen-7-yl)oxypentoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C=2C1=CC(OCCCCCOC1=C3C(=O)C=C(OC3=CC=C1)C(=O)O)=CC=2 KLHNFEIYXZFYEF-UHFFFAOYSA-N 0.000 description 1
- PWAATCXREMPGJZ-UHFFFAOYSA-N 5-[5-(2-carboxy-8-chloro-4-oxochromen-5-yl)oxypentoxy]-8-chloro-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(Cl)=CC=C2OCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=C(Cl)C=C1 PWAATCXREMPGJZ-UHFFFAOYSA-N 0.000 description 1
- CNBYRSHFEBAGBB-UHFFFAOYSA-N 5-[8-(2-carboxy-4-oxochromen-5-yl)oxyoctoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 CNBYRSHFEBAGBB-UHFFFAOYSA-N 0.000 description 1
- UNIVIWZHQOASHG-UHFFFAOYSA-N 5-[9-(2-carboxy-4-oxochromen-5-yl)oxynonoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 UNIVIWZHQOASHG-UHFFFAOYSA-N 0.000 description 1
- CLKCOOGQYKTQAV-UHFFFAOYSA-N 6-[3-(2-carboxy-4-oxochromen-6-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=CC(OCC(COC=3C=C4C(=O)C=C(OC4=CC=3)C(O)=O)O)=CC=C21 CLKCOOGQYKTQAV-UHFFFAOYSA-N 0.000 description 1
- QFLQVUAJKXUXOF-UHFFFAOYSA-N 7-[3-(2-carboxy-4-oxochromen-7-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C=2C1=CC(OCC(COC=1C=C3C(C(C=C(O3)C(O)=O)=O)=CC=1)O)=CC=2 QFLQVUAJKXUXOF-UHFFFAOYSA-N 0.000 description 1
- OEKDOSRDAIBBJH-UHFFFAOYSA-N 7-[5-(2-carboxy-4-oxochromen-7-yl)oxypentoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C=2C1=CC(OCCCCCOC1=CC=C3C(=O)C=C(OC3=C1)C(=O)O)=CC=2 OEKDOSRDAIBBJH-UHFFFAOYSA-N 0.000 description 1
- VSMFNICCLNJMKD-UHFFFAOYSA-N 7-[5-(2-carboxy-8-methyl-4-oxochromen-7-yl)oxypentoxy]-8-methyl-4-oxochromene-2-carboxylic acid Chemical compound C1=CC(C(C=C(O2)C(O)=O)=O)=C2C(C)=C1OCCCCCOC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1C VSMFNICCLNJMKD-UHFFFAOYSA-N 0.000 description 1
- OEXYRGYCZKWBTL-UHFFFAOYSA-N 8-[5-(2-carboxy-4-oxochromen-8-yl)oxypentoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(OCCCCCOC=1C=CC=C3C(=O)C=C(OC3=1)C(=O)O)=CC=C2 OEXYRGYCZKWBTL-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NHQJPVPSTALWGZ-UHFFFAOYSA-N O.C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCC(COCC(COC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O)O)O Chemical compound O.C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCC(COCC(COC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O)O)O NHQJPVPSTALWGZ-UHFFFAOYSA-N 0.000 description 1
- GIOKFSNYCVNEGL-UHFFFAOYSA-N O.C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCCCCCOC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O Chemical compound O.C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCCCCCOC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O GIOKFSNYCVNEGL-UHFFFAOYSA-N 0.000 description 1
- WVFORMHKBFWUNT-UHFFFAOYSA-N O.O.O.O.[K] Chemical compound O.O.O.O.[K] WVFORMHKBFWUNT-UHFFFAOYSA-N 0.000 description 1
- FJRXGBBVWWBHMW-UHFFFAOYSA-N O.O.O.O.[Na].[Na] Chemical compound O.O.O.O.[Na].[Na] FJRXGBBVWWBHMW-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 208000028004 allergic respiratory disease Diseases 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011340 continuous therapy Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical compound CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 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
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- BCDBJMHHUNQXOF-UHFFFAOYSA-N ethyl 5-[2-(2-ethoxycarbonyl-4-oxochromen-5-yl)oxyethoxy]-4-oxochromene-2-carboxylate Chemical compound C(C)OC(=O)C=1OC2=CC=CC(=C2C(C=1)=O)OCCOC1=C2C(C=C(OC2=CC=C1)C(=O)OCC)=O BCDBJMHHUNQXOF-UHFFFAOYSA-N 0.000 description 1
- NHTQBRYOLDTPHT-UHFFFAOYSA-N ethyl 5-[3-(2-ethoxycarbonyl-4-oxochromen-7-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylate Chemical compound C(C)OC(=O)C=1OC2=CC=CC(=C2C(C1)=O)OCC(COC1=CC=C2C(C=C(OC2=C1)C(=O)OCC)=O)O NHTQBRYOLDTPHT-UHFFFAOYSA-N 0.000 description 1
- ZLAPMSVUFSXCNX-UHFFFAOYSA-N ethyl 6-[5-(2-ethoxycarbonyl-4-oxochromen-6-yl)oxypentoxy]-4-oxochromene-2-carboxylate Chemical compound C(C)OC(=O)C=1OC2=CC=C(C=C2C(C1)=O)OCCCCCOC=1C=C2C(C=C(OC2=CC1)C(=O)OCC)=O ZLAPMSVUFSXCNX-UHFFFAOYSA-N 0.000 description 1
- RKIMFICEWCXBCE-UHFFFAOYSA-N ethyl 7-hydroxy-4-oxochromene-2-carboxylate Chemical compound C1=C(O)C=C2OC(C(=O)OCC)=CC(=O)C2=C1 RKIMFICEWCXBCE-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 231100000037 inhalation toxicity test Toxicity 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical class CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical group [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J3/00—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification
- F25J3/02—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream
- F25J3/04—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air
- F25J3/04248—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion
- F25J3/04284—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion using internal refrigeration by open-loop gas work expansion, e.g. of intermediate or oxygen enriched (waste-)streams
- F25J3/04309—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion using internal refrigeration by open-loop gas work expansion, e.g. of intermediate or oxygen enriched (waste-)streams of nitrogen
- F25J3/04315—Lowest pressure or impure nitrogen, so-called waste nitrogen expansion
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J3/00—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification
- F25J3/02—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream
- F25J3/04—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air
- F25J3/04151—Purification and (pre-)cooling of the feed air; recuperative heat-exchange with product streams
- F25J3/04187—Cooling of the purified feed air by recuperative heat-exchange; Heat-exchange with product streams
- F25J3/04193—Division of the main heat exchange line in consecutive sections having different functions
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J3/00—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification
- F25J3/02—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream
- F25J3/04—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air
- F25J3/04248—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion
- F25J3/04284—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion using internal refrigeration by open-loop gas work expansion, e.g. of intermediate or oxygen enriched (waste-)streams
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J3/00—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification
- F25J3/02—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream
- F25J3/04—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air
- F25J3/04248—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion
- F25J3/04284—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion using internal refrigeration by open-loop gas work expansion, e.g. of intermediate or oxygen enriched (waste-)streams
- F25J3/0429—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion using internal refrigeration by open-loop gas work expansion, e.g. of intermediate or oxygen enriched (waste-)streams of feed air, e.g. used as waste or product air or expanded into an auxiliary column
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J3/00—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification
- F25J3/02—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream
- F25J3/04—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air
- F25J3/04248—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion
- F25J3/04284—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion using internal refrigeration by open-loop gas work expansion, e.g. of intermediate or oxygen enriched (waste-)streams
- F25J3/04321—Generation of cold for compensating heat leaks or liquid production, e.g. by Joule-Thompson expansion using internal refrigeration by open-loop gas work expansion, e.g. of intermediate or oxygen enriched (waste-)streams of oxygen
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J3/00—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification
- F25J3/02—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream
- F25J3/04—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air
- F25J3/04406—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air using a dual pressure main column system
- F25J3/04412—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air using a dual pressure main column system in a classical double column flowsheet, i.e. with thermal coupling by a main reboiler-condenser in the bottom of low pressure respectively top of high pressure column
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J2200/00—Processes or apparatus using separation by rectification
- F25J2200/20—Processes or apparatus using separation by rectification in an elevated pressure multiple column system wherein the lowest pressure column is at a pressure well above the minimum pressure needed to overcome pressure drop to reject the products to atmosphere
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J2200/00—Processes or apparatus using separation by rectification
- F25J2200/50—Processes or apparatus using separation by rectification using multiple (re-)boiler-condensers at different heights of the column
- F25J2200/54—Processes or apparatus using separation by rectification using multiple (re-)boiler-condensers at different heights of the column in the low pressure column of a double pressure main column system
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J2215/00—Processes characterised by the type or other details of the product stream
- F25J2215/40—Air or oxygen enriched air, i.e. generally less than 30mol% of O2
Landscapes
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Mechanical Engineering (AREA)
- Thermal Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Separation By Low-Temperature Treatments (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Ceramic Products (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/446,363 US4453957A (en) | 1982-12-02 | 1982-12-02 | Double column multiple condenser-reboiler high pressure nitrogen process |
Publications (2)
Publication Number | Publication Date |
---|---|
NO834422L NO834422L (no) | 1984-06-04 |
NO162258B true NO162258B (no) | 1989-08-21 |
Family
ID=23772305
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO834422A NO162258B (no) | 1982-12-02 | 1983-12-01 | Fremgangsm te for fremstilling av nitrogengass. |
Country Status (6)
Country | Link |
---|---|
US (1) | US4453957A (nl) |
CA (1) | CA1210315A (nl) |
DK (1) | DK161084C (nl) |
GB (1) | GB2131147B (nl) |
NL (1) | NL8304118A (nl) |
NO (1) | NO162258B (nl) |
Families Citing this family (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4604117A (en) * | 1984-11-15 | 1986-08-05 | Union Carbide Corporation | Hybrid nitrogen generator with auxiliary column drive |
FR2578532B1 (fr) * | 1985-03-11 | 1990-05-04 | Air Liquide | Procede et installation de production d'azote |
GB8512562D0 (en) * | 1985-05-17 | 1985-06-19 | Boc Group Plc | Liquid-vapour contact method |
DE3528374A1 (de) * | 1985-08-07 | 1987-02-12 | Linde Ag | Verfahren und vorrichtung zur erzeugung von stickstoff mit ueberatmosphaerischem druck |
US4617036A (en) * | 1985-10-29 | 1986-10-14 | Air Products And Chemicals, Inc. | Tonnage nitrogen air separation with side reboiler condenser |
AT386279B (de) * | 1986-04-02 | 1988-07-25 | Voest Alpine Ag | Vorrichtung zur zerlegung von gasen mittels koaxial ineinander angeordneter rektifikationskolonnen |
US4715874A (en) * | 1986-09-08 | 1987-12-29 | Erickson Donald C | Retrofittable argon recovery improvement to air separation |
US4775399A (en) * | 1987-11-17 | 1988-10-04 | Erickson Donald C | Air fractionation improvements for nitrogen production |
US4783210A (en) * | 1987-12-14 | 1988-11-08 | Air Products And Chemicals, Inc. | Air separation process with modified single distillation column nitrogen generator |
US4822395A (en) * | 1988-06-02 | 1989-04-18 | Union Carbide Corporation | Air separation process and apparatus for high argon recovery and moderate pressure nitrogen recovery |
US4848996A (en) * | 1988-10-06 | 1989-07-18 | Air Products And Chemicals, Inc. | Nitrogen generator with waste distillation and recycle of waste distillation overhead |
US4869742A (en) * | 1988-10-06 | 1989-09-26 | Air Products And Chemicals, Inc. | Air separation process with waste recycle for nitrogen and oxygen production |
US5116396A (en) * | 1989-05-12 | 1992-05-26 | Union Carbide Industrial Gases Technology Corporation | Hybrid prepurifier for cryogenic air separation plants |
US5004482A (en) * | 1989-05-12 | 1991-04-02 | Union Carbide Corporation | Production of dry, high purity nitrogen |
US4934148A (en) * | 1989-05-12 | 1990-06-19 | Union Carbide Corporation | Dry, high purity nitrogen production process and system |
US4931070A (en) * | 1989-05-12 | 1990-06-05 | Union Carbide Corporation | Process and system for the production of dry, high purity nitrogen |
US4957524A (en) * | 1989-05-15 | 1990-09-18 | Union Carbide Corporation | Air separation process with improved reboiler liquid cleaning circuit |
US5006137A (en) * | 1990-03-09 | 1991-04-09 | Air Products And Chemicals, Inc. | Nitrogen generator with dual reboiler/condensers in the low pressure distillation column |
US5069699A (en) * | 1990-09-20 | 1991-12-03 | Air Products And Chemicals, Inc. | Triple distillation column nitrogen generator with plural reboiler/condensers |
US5098457A (en) * | 1991-01-22 | 1992-03-24 | Union Carbide Industrial Gases Technology Corporation | Method and apparatus for producing elevated pressure nitrogen |
FR2685459B1 (fr) * | 1991-12-18 | 1994-02-11 | Air Liquide | Procede et installation de production d'oxygene impur. |
US5233838A (en) * | 1992-06-01 | 1993-08-10 | Praxair Technology, Inc. | Auxiliary column cryogenic rectification system |
US6205374B1 (en) * | 1993-07-01 | 2001-03-20 | Mazda Motor Corporation | Vehicle characteristic change system and method |
US5402647A (en) * | 1994-03-25 | 1995-04-04 | Praxair Technology, Inc. | Cryogenic rectification system for producing elevated pressure nitrogen |
GB9500120D0 (en) * | 1995-01-05 | 1995-03-01 | Boc Group Plc | Air separation |
US5697229A (en) * | 1996-08-07 | 1997-12-16 | Air Products And Chemicals, Inc. | Process to produce nitrogen using a double column plus an auxiliary low pressure separation zone |
US5682762A (en) * | 1996-10-01 | 1997-11-04 | Air Products And Chemicals, Inc. | Process to produce high pressure nitrogen using a high pressure column and one or more lower pressure columns |
US5682764A (en) * | 1996-10-25 | 1997-11-04 | Air Products And Chemicals, Inc. | Three column cryogenic cycle for the production of impure oxygen and pure nitrogen |
US5761927A (en) * | 1997-04-29 | 1998-06-09 | Air Products And Chemicals, Inc. | Process to produce nitrogen using a double column and three reboiler/condensers |
US6009723A (en) * | 1998-01-22 | 2000-01-04 | Air Products And Chemicals, Inc. | Elevated pressure air separation process with use of waste expansion for compression of a process stream |
US6065306A (en) * | 1998-05-19 | 2000-05-23 | The Boc Group, Inc. | Method and apparatus for purifying ammonia |
US5934104A (en) * | 1998-06-02 | 1999-08-10 | Air Products And Chemicals, Inc. | Multiple column nitrogen generators with oxygen coproduction |
DE19902255A1 (de) * | 1999-01-21 | 2000-07-27 | Linde Tech Gase Gmbh | Verfahren und Vorrichtung zur Gewinnung von Druckstickstoff |
GB0119500D0 (en) * | 2001-08-09 | 2001-10-03 | Boc Group Inc | Nitrogen generation |
US6499312B1 (en) | 2001-12-04 | 2002-12-31 | Praxair Technology, Inc. | Cryogenic rectification system for producing high purity nitrogen |
US7114352B2 (en) * | 2003-12-24 | 2006-10-03 | Praxair Technology, Inc. | Cryogenic air separation system for producing elevated pressure nitrogen |
US8640496B2 (en) * | 2008-08-21 | 2014-02-04 | Praxair Technology, Inc. | Method and apparatus for separating air |
US8820115B2 (en) * | 2009-12-10 | 2014-09-02 | Praxair Technology, Inc. | Oxygen production method and apparatus |
US20110138856A1 (en) * | 2009-12-10 | 2011-06-16 | Henry Edward Howard | Separation method and apparatus |
EP3059536A1 (de) * | 2015-02-19 | 2016-08-24 | Linde Aktiengesellschaft | Verfahren und Vorrichtung zur Gewinnung eines Druckstickstoffprodukts |
EP3290843A3 (de) | 2016-07-12 | 2018-06-13 | Linde Aktiengesellschaft | Verfahren und vorrichtung zur erzeugung von druckstickstoff und flüssigstickstoff durch tieftemperaturzerlegung von luft |
CN110869687B (zh) | 2017-05-16 | 2021-11-09 | 特伦斯·J·埃伯特 | 液化气体用装置和工艺 |
DE102018000842A1 (de) * | 2018-02-02 | 2019-08-08 | Linde Aktiengesellschaft | Verfahren und Vorrichtung zur Gewinnung von Druckstickstoff durch Tieftemperaturzerlegung von Luft |
EP3757493A1 (de) | 2019-06-25 | 2020-12-30 | Linde GmbH | Verfahren und anlage zur gewinnung eines stickstoffreichen und eines sauerstoffreichen luftprodukts unter einsatz einer tieftemperaturzerlegung von luft |
WO2021242308A1 (en) | 2020-05-26 | 2021-12-02 | Praxair Technology, Inc. | Enhancements to a dual column nitrogen producing cryogenic air separation unit |
WO2021242309A1 (en) | 2020-05-26 | 2021-12-02 | Praxair Technology, Inc. | Enhancements to a dual column nitrogen producing cryogenic air separation unit |
WO2021242307A1 (en) | 2020-05-28 | 2021-12-02 | Praxair Technology, Inc. | Enhancements to a dual column nitrogen producing cryogenic air separation unit |
US11674750B2 (en) | 2020-06-04 | 2023-06-13 | Praxair Technology, Inc. | Dual column nitrogen producing air separation unit with split kettle reboil and integrated condenser-reboiler |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2873583A (en) * | 1954-05-04 | 1959-02-17 | Union Carbide Corp | Dual pressure cycle for air separation |
US3210947A (en) * | 1961-04-03 | 1965-10-12 | Union Carbide Corp | Process for purifying gaseous streams by rectification |
US3203193A (en) * | 1963-02-06 | 1965-08-31 | Petrocarbon Dev Ltd | Production of nitrogen |
US3217502A (en) * | 1963-04-22 | 1965-11-16 | Hydrocarbon Research Inc | Liquefaction of air |
US3270514A (en) * | 1963-04-23 | 1966-09-06 | Gas Equipment Engineering Corp | Separation of gas mixtures |
US3348385A (en) * | 1964-12-23 | 1967-10-24 | Gas Equipment Engineering Corp | Separation of gas mixtures |
GB1180904A (en) * | 1966-06-01 | 1970-02-11 | British Oxygen Co Ltd | Air Separation Process. |
US3375673A (en) * | 1966-06-22 | 1968-04-02 | Hydrocarbon Research Inc | Air separation process employing work expansion of high and low pressure nitrogen |
FR2064440B1 (nl) * | 1969-10-20 | 1973-11-23 | Kobe Steel Ltd | |
GB1576910A (en) * | 1978-05-12 | 1980-10-15 | Air Prod & Chem | Process and apparatus for producing gaseous nitrogen |
-
1982
- 1982-12-02 US US06/446,363 patent/US4453957A/en not_active Expired - Lifetime
-
1983
- 1983-10-14 CA CA000439043A patent/CA1210315A/en not_active Expired
- 1983-12-01 DK DK551983A patent/DK161084C/da active
- 1983-12-01 GB GB08332133A patent/GB2131147B/en not_active Expired
- 1983-12-01 NL NL8304118A patent/NL8304118A/nl active Search and Examination
- 1983-12-01 NO NO834422A patent/NO162258B/no unknown
Also Published As
Publication number | Publication date |
---|---|
DK161084C (da) | 1991-11-18 |
US4453957A (en) | 1984-06-12 |
CA1210315A (en) | 1986-08-26 |
GB8332133D0 (en) | 1984-01-11 |
NL8304118A (nl) | 1984-07-02 |
NO834422L (no) | 1984-06-04 |
GB2131147B (en) | 1986-05-08 |
DK161084B (da) | 1991-05-27 |
DK551983D0 (da) | 1983-12-01 |
GB2131147A (en) | 1984-06-13 |
DK551983A (da) | 1984-06-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO162258B (no) | Fremgangsm te for fremstilling av nitrogengass. | |
NO124832B (nl) | ||
Manolov et al. | Synthesis, toxicological and pharmacological assessment of some 4-hydroxycoumarin derivatives | |
Dhawan et al. | Calixarenes. 10. oxacalixarenes | |
US4564686A (en) | Phosphoric acid diesters or their salts and process for producing the same | |
JPS58131936A (ja) | フエニルカルボン酸誘導体、その製造法及び該化合物を含有する、緩慢にアナフイラキシ−作用する物質に対する「あ」抗剤 | |
JPS6033834B2 (ja) | ヘキサヒドロジベンゾピラノン類の製法 | |
SU1072805A3 (ru) | Способ получени производных флавана или их солей | |
US3885038A (en) | Method of using substituted xanthone carboxylic acid | |
Khan et al. | Synthesis and antihepatotoxic activity of some new chalcones containing 1, 4-dioxane ring system | |
US3899513A (en) | 1-(2-substituted-chromonyloxy)-2-hydroxy-3-(substituted-phenoxy)propanes | |
US3686320A (en) | Bis-phenoxy compounds | |
FI95250C (fi) | Menetelmä uusien, terapeuttisesti käyttökelpoisten kromaanijohdannaisten valmistamiseksi | |
US3953604A (en) | 1-(2-Substituted-chromonyloxy)-2-hydroxy-3-(substituted phenoxy)propanes | |
AU623383B2 (en) | Novel alkanophenones | |
US3777033A (en) | Bis-chromonyl pharmaceutical composi-tion and methods | |
US4315862A (en) | Process for preparing cannabichromene | |
DE68907095T2 (de) | Verbindungen zur Verhinderung der Biosynthese von der Lipoxygenase abgeleiteten Metaboliten der Arachidonsäure. | |
SE453493B (sv) | Nya alifatiska fenylkarboxylsyror sett for framstellning derav, anvendning derav som lekemedel och kompositioner innehallande dem | |
SU831074A3 (ru) | Способ получени производных бензимида-зОлА | |
CA1303294C (en) | .alpha.-HYDROXY THIOETHERS | |
IE55377B1 (en) | 1,5-diphenylpyrazolin-3-one compounds,method for preparing them,and pharmaceutical compositions containing these compounds | |
NO124994B (nl) | ||
SE455420B (sv) | Anvendning av 4-fenyl-4-oxo-butensyraderivat for framstellning av ett lekemedel for behandling av magakommor och gastroduodenala akommor i samband med hyperaciditet | |
Holland et al. | Cinnoline-3-propionic acids, a new series of orally active antiallergic substances |