US2058403A - Organic bismuth compounds of hydroaromatic endomethylene benzoic acids - Google Patents
Organic bismuth compounds of hydroaromatic endomethylene benzoic acids Download PDFInfo
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- US2058403A US2058403A US697078A US69707833A US2058403A US 2058403 A US2058403 A US 2058403A US 697078 A US697078 A US 697078A US 69707833 A US69707833 A US 69707833A US 2058403 A US2058403 A US 2058403A
- Authority
- US
- United States
- Prior art keywords
- endomethylene
- acid
- water
- bismuth
- endo
- 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.)
- Expired - Lifetime
Links
- 150000001622 bismuth compounds Chemical class 0.000 title description 5
- 235000010233 benzoic acid Nutrition 0.000 title description 3
- 150000001559 benzoic acids Chemical class 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 11
- 150000001621 bismuth Chemical class 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 239000005711 Benzoic acid Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- ZURRKVIQUKNLHF-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptane-3-carboxylic acid Chemical compound C1CC2(C)C(C(O)=O)CC1C2(C)C ZURRKVIQUKNLHF-UHFFFAOYSA-N 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- -1 methylene-hexahydromethyl-benzoic acid Chemical compound 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- 241000193803 Therea Species 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- CJJMLLCUQDSZIZ-UHFFFAOYSA-N oxobismuth Chemical class [Bi]=O CJJMLLCUQDSZIZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/12—Saturated polycyclic compounds
- C07C61/125—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system
- C07C61/13—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system having two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
Definitions
- the present invention relates to organic bismuth compounds of hydroaromatic endomethylene benzoic acids.
- Suitable acids of the said kind are the endomethylene-benzoic acid obtainable by oxidation of camphene and similar compounds, for instance, the camphenilanic acid of the formula CH: 011C003 or the acid of the following formula CH.COOH i or the homologous acid of the formula
- the unsaturated endo-methylene-carboxylic acids obtained as well as the corresponding saturated endo-methylene-carboxylic acids may be transformed into their bismuth salts.
- the saturated endo-methylene-carboxylic acids are obtainable from the unsaturated acids by bydrogenation.
- CILCOOE there may also be used endo-methylene-benzoic acids, wherein the endo-methylene-hydrogen atoms have been exchanged for alkyl groups, for instance, the camphane-carboxylic acids of the formula Beilstein, 4th edition, volume9, page 74) are dis-
- the monoiodo-endomethylene-hexahydromethyl 1" benzoic acid obtainable by addition'of'hydroge'n iodide to the endo-methylene 2.5 'deltas tetra-' hydro-G-methylbenzoic acid, the corresponding diiodo-endtomethylene-hexahydromethyl-benzoic acid obtainable by addition of iodine to the-same parent acid, the mono-iodo-endomethylene-tetrahydromethyl-benzoic acid obtainable 'by-splitei ting off hydrogen iodide from the diiodo-endo methylene-hexahydro
- the new bismuth compounds can be obtained by causing a bismuth salt to act upon a whollylor partially hydrogenated endo-methylene-benzoic acid.
- the new bismuth compounds are amorphous substances which decompose without melting when heated, and are insoluble in water, soluble in ether, chloroform and oils and have a strong bactericidal action especially against spirilli, but only a comparatively small toxicity.
- H P Bi CH: l 011-000- said salt being an amorphous substance, insoluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
- the bismuth salt of isocamphenilanic acid said salt being an amorphous substance, insoluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
- said salt being an amorphous substance, in- 15 soluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Patented Oct. 27, 1936 UNITED STATES PATENT OFFICE ORGANIC BISMUTH COMPOUNDS OF HY- DROAROMATIC ENDOMETHYLENE BEN- ZOIC ACIDS Max Bockmiihl, Walter Pei-sch, and Gustav Ehrhart, Frankfort-on-the-Main-Hochst, Germany, assignors to Winthrop Chemical Company, Inc., New York, N. Y., a corporation of New York No Drawing. Application November 7, 1933, Serial No. 697,078. In Germany November 8,
7 Claims.
The present invention relates to organic bismuth compounds of hydroaromatic endomethylene benzoic acids.
We have found that the bismuth salts of wholly or partially hydrogenated endo-methylene-benzoic acids possess good chemotherapeutic properties. Suitable acids of the said kind are the endomethylene-benzoic acid obtainable by oxidation of camphene and similar compounds, for instance, the camphenilanic acid of the formula CH: 011C003 or the acid of the following formula CH.COOH i or the homologous acid of the formula In the latter case the unsaturated endo-methylene-carboxylic acids obtained as well as the corresponding saturated endo-methylene-carboxylic acids may be transformed into their bismuth salts. The saturated endo-methylene-carboxylic acids are obtainable from the unsaturated acids by bydrogenation. There may be used for instance, the endo-methylene-hexahydrobenzoic acid of the formula or the endo-methylene-hexahydromethy1benzoic acid of the formula CH on I a \CH CH: CILOO OH or the endo-methylene-hexahydroethylbenzoic acid of the formula 0 Ha OH: I
CILCOOE There may also be used endo-methylene-benzoic acids, wherein the endo-methylene-hydrogen atoms have been exchanged for alkyl groups, for instance, the camphane-carboxylic acids of the formula Beilstein, 4th edition, volume9, page 74) are dis- The monoiodo-endomethylene-hexahydromethyl 1" benzoic acid obtainable by addition'of'hydroge'n iodide to the endo-methylene 2.5 'deltas tetra-' hydro-G-methylbenzoic acid, the corresponding diiodo-endtomethylene-hexahydromethyl-benzoic acid obtainable by addition of iodine to the-same parent acid, the mono-iodo-endomethylene-tetrahydromethyl-benzoic acid obtainable 'by-splitei ting off hydrogen iodide from the diiodo-endo methylene-hexahydromethyl-benzoic acid, finally nitrated, partially or wholly hydrogenated endo-methylene-benzoic acids.
The salts of the formula (R) 313i and those of the formula R.Bi=O, wherein R stands for the radical of a wholly or partially hydrogenated endo-methylene-benzoic acid, are therapeutically valuable compounds. g
They can be obtained by causing a bismuth salt to act upon a whollylor partially hydrogenated endo-methylene-benzoic acid. The new bismuth compounds are amorphous substances which decompose without melting when heated, and are insoluble in water, soluble in ether, chloroform and oils and have a strong bactericidal action especially against spirilli, but only a comparatively small toxicity.
The following examples illustrate the invention: (1) 51 grams of camphenilanic acid (cf.
solved together with 12igrams of caustic soda in 150 cc. of water. The solution is mixed with a solution of 48.5 grams of crystallized bismuth nitrate in 150 ccof glycerine and 300 cc. of water. The white precipitate obtained is washed with water and dried. It is the bismuth salt of the camphenilanic acid, readily soluble in chloro-,
form, benzene, ether and oils, insoluble in water and containing 29.7 per cent. of bismuth (cal culated 29.4 per cent. for (C1oH15O2)3Bi).
(2) 3.5 grams of isocamphenilanic acid (Beilstein, 4th edition, volume 9, page 74) are dissolved in 50 cc. of water together with 22 cc. of N-caustic soda solution.- The. solution is mixed with a solution of 3.5 grams of crystallized bismuth nitrate in cc. of glycerine and. cc. of water. The product is worked up as indicated in Example 1. The colorless bismuth compound has the same physical properties salt of camphenilanic acid.
(3) There are dissolved in 15 cc. of alcohol 152 grams of endo-methylene-2.5-delta3-tetrahydro- G-methylbenzoic acid (obtained from cyclopentadiene and crotonic acid by the method described in Annalen, volume 460, page 117): colorless apparently rhombic tablets melting at 96 C. to 97 (3.). The "solution is neutralized with caustic soda solution and the bismuth salt is precipitated, while stirring and cooling, by adding a solution of 16.2 grams of bismuth nitrate in 46 grams of an aqueous mannite solution of 13 per cent. strength. The resultant white voluminous precipitate is soluble in ether, benzene and olive oil and contains 31.6 per cent. of bismuth; it, therea t e b m t paper. The white precipitate obtained is filtered fore, corresponds with the formula: (Cal-11102) 3181.
(4) 18- grams of camphane-carboxylic acid are dissolved in 100 cc. of N-caustic soda solution. The solution obtained is mixed with a solution of 1'7 grams of bismuth nitrate, 8 grams .of .rnannite and 100 cc. of water. The bismuth salt of camphane-carboxylic acid which is thus precipitated is filtered by suction and washed with .water.
It is readily soluble in ether, chloroform and oils, sparingly soluble in water.
(5). 16.8 grams of camphenilanic acid are dissolvedtogether with 4 grams of caustic soda in 150 cc. of water. Into the solution so obtained ,there are simultaneously introduced, while stirring, a solution of 48.5 grams of crystallized bisrnuth nitrate in 150 cc. of glycerine and 300 cc. of "water .and a solution of 8 grams of caustic soda in 100 cc. of water in such a manner that the liquid always shows an alkaline reaction to litmus by suction, washed with water and then dissolved inbenzene. By evaporating the dried 'filtered benzene solution there is obtained the bismuthoxide salt of camphenilanic acid of the formula CioH15O2.BiO soluble in oil. The product contains 53.3 per cent. of bismuth (theory 53.3 per cent). We claim: V 1. The bismuth salts of acids of the following formula R.COOH in which R. stands for a hydroaromatic hydrocarbon radical of the endomethylene-benzene series, said salts being amorphous substances, insoluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli. 2. The bismuth salts of acids of the following formula R.COOH in which R stands for a wholly hydrogenated hydrocarbon radical of the endomethylene-benzene series, said salts being amorphous substances, insoluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
3. The bismuth salts ofacids of the following formula in which R stands for the radical of a wholly hydrogenated hydrocarbon of the endomethylene-benzenei series substituted by lower alkyl groups, said-salts being amorphous substances, insoluble in water, soluble in: ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
4. The bismuthsalts of the acids of the following formula in which R stands for "the radical of a wholly hydrogenated hydrocarbon 0f the endomethylene-benzene series .substitutedby methyl groups, said compounds being amorphous substances, insoluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
H: P Bi CH: l 011-000- said salt being an amorphous substance, insoluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
6. The bismuth salt of isocamphenilanic acid, said salt being an amorphous substance, insoluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
7. The bismuth salt of camphane-carboxylic acid of the following formula:
said salt being an amorphous substance, in- 15 soluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
MAX BOCKM'UHL. 20 WALTER PERSCH. GUSTAV EHRHAR'I.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE428147X | 1932-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2058403A true US2058403A (en) | 1936-10-27 |
Family
ID=6477416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US697078A Expired - Lifetime US2058403A (en) | 1932-11-08 | 1933-11-07 | Organic bismuth compounds of hydroaromatic endomethylene benzoic acids |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2058403A (en) |
| GB (1) | GB428147A (en) |
| NL (1) | NL37063C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021598A (en) * | 1989-07-24 | 1991-06-04 | Mooney Chemicals, Inc. | Process for making bismuth carboxylates |
| EP2796531A4 (en) * | 2011-12-22 | 2015-08-12 | G C Dental Ind Corp | Agent for imparting fluorescence to ceramic |
-
0
- NL NL37063D patent/NL37063C/xx active
-
1933
- 1933-11-07 US US697078A patent/US2058403A/en not_active Expired - Lifetime
- 1933-11-08 GB GB31142/33A patent/GB428147A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021598A (en) * | 1989-07-24 | 1991-06-04 | Mooney Chemicals, Inc. | Process for making bismuth carboxylates |
| EP2796531A4 (en) * | 2011-12-22 | 2015-08-12 | G C Dental Ind Corp | Agent for imparting fluorescence to ceramic |
Also Published As
| Publication number | Publication date |
|---|---|
| GB428147A (en) | 1935-05-08 |
| NL37063C (en) |
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