DE688083C - Process for the production of capillary-active, betaine-like compounds - Google Patents
Process for the production of capillary-active, betaine-like compoundsInfo
- Publication number
- DE688083C DE688083C DE1937D0074370 DED0074370A DE688083C DE 688083 C DE688083 C DE 688083C DE 1937D0074370 DE1937D0074370 DE 1937D0074370 DE D0074370 A DED0074370 A DE D0074370A DE 688083 C DE688083 C DE 688083C
- Authority
- DE
- Germany
- Prior art keywords
- betaine
- compounds
- production
- capillary
- active
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- -1 heterocyclic Amines Chemical group 0.000 claims description 15
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 229960003237 betaine Drugs 0.000 claims description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 230000008707 rearrangement Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CCOGBEKDJSLMEC-UHFFFAOYSA-N 1-hexadecylpiperidine Chemical compound CCCCCCCCCCCCCCCCN1CCCCC1 CCOGBEKDJSLMEC-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QQWGVQWAEANRTK-UHFFFAOYSA-N bromosuccinic acid Chemical compound OC(=O)CC(Br)C(O)=O QQWGVQWAEANRTK-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- BHDDSIBLLZQKRF-UHFFFAOYSA-N 1-dodecylpiperidine Chemical compound CCCCCCCCCCCCN1CCCCC1 BHDDSIBLLZQKRF-UHFFFAOYSA-N 0.000 description 1
- BBYSGWAYRRMWOW-UHFFFAOYSA-N 1-hexylpiperidine Chemical compound CCCCCCN1CCCCC1 BBYSGWAYRRMWOW-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- DWSGLSZEOZQMSP-UHFFFAOYSA-N potassium;sodium Chemical class [Na+].[K+] DWSGLSZEOZQMSP-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/10—Quaternary compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Hydrogenated Pyridines (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Verfahren zur Herstellung kapillaraktiver, betainartiger Verbindungen Es ist bekannt, daß man saure Salze aus bestimmten reaktionsfähigen, d. h. zur Betainbildung befähigten, ungesättigten- oder monohalogenierten Di- oder Polycarbonsäuren bzw. deren reaktionsfähigenAbkömmlingen und reaktionsfähigen tertiären Aminen zu den entsprechenden Verbindungen vom Betaintypus umlagern kann. Zu dieser Umlagerung sind z. B. Salze befähigt, die einerseits aus Säuren, wie Fumarsäure, Maleinsäure, Brombernsteinsäure, Mäleinsäuremonoäthylester usw., und andererseits aus tertiären Aminen, wie Pyridin, Isochinolin, Picolin, Lutidin, Kollidin usw., gebildet sind (vgl. Ber. d. dtsch. chem. Ges., Bd. 43 [191o], S. 2636, und Bd. 69 [1936], S. 419, sowie Chem. Zentralblatt 1933 11, S. 2823, und 1g16 11, S. 216).Process for the production of capillary-active, betaine-like compounds It is known that acid salts from certain reactive, ie capable of betaine formation, unsaturated or monohalogenated di- or polycarboxylic acids or their reactive derivatives and reactive tertiary amines can be rearranged to the corresponding compounds of the betaine type. For this rearrangement are z. B. enables salts that are formed on the one hand from acids such as fumaric acid, maleic acid, bromosuccinic acid, maleic acid monoethyl ester, etc., and on the other hand from tertiary amines such as pyridine, isoquinoline, picoline, lutidine, collidine, etc. (cf. Ber. D. German Chem. Ges., Vol. 43 [1910], p. 2636, and Vol. 69 [1936], p. 419, as well as Chem. Zentralblatt 1933 11, p. 2823, and 1g16 11, p. 216).
Es wurde nun gefunden, daß man zu neuartigen Stoffen gelangt, die sich gegenüber den bisher bekannten durch kapillaraktive Eigenschaften auszeichnen, wenn man diese Umlagerung an sauren Salzen aus Malein- bzw. Fumarsäure, deren Estern oder diesen Säuren entsprechenden gesättigten Monohalogencarbonsäuren und solchen hydrierten, tertiären, heterocyclischen Aminen vornimmt, die mindestens einen Alkylrest von wenigstens sechs Kohlenstoffatomen im Molekül enthalten, wie beispielsweise N-Hexylpiperidin, N-Hexadecylpiperidin, N-Dodecylisochinolintetrahydrid o. dgl.It has now been found that one arrives at novel substances which distinguish themselves from the previously known by capillary-active properties, if this rearrangement of acidic salts of maleic or fumaric acid, their esters or saturated monohalocarboxylic acids and those corresponding to these acids hydrogenated, tertiary, heterocyclic amines that contain at least one alkyl radical of at least six carbon atoms in the molecule, such as N-hexylpiperidine, N-hexadecylpiperidine, N-dodecylisoquinoline tetrahydride or the like.
Die Umlagerung erfolgt ganz allgemein durch Erwärmen der sauren carbonsauren Salze der tertiären Basen auf Temperaturen über ioo°, am zweckmäßigsten auf 12o bis 16o', für sich allein oder in Gegenwart von die Umsetzung beschleunigenden Lösungsmitteln, wie Alkoholen, z. B. Cyclohexanol, Benzylalkohol, Ketonen, z. B. Cyclohexanon, Cyclopentanon, Acetophenon, Kohlenwasserstoffen u. dgl.The rearrangement takes place quite generally by heating the acidic carboxylic acids Salts of the tertiary bases at temperatures above 100 °, most expediently at 12 ° up to 16o ', on their own or in the presence of solvents that accelerate the reaction, such as alcohols, e.g. B. cyclohexanol, benzyl alcohol, ketones, e.g. B. Cyclohexanone, Cyclopentanone, Acetophenone, hydrocarbons and the like.
Die leichte Zugänglichkeit dieser Betaine, deren Umsetzung praktisch quantitativ verläuft, macht kein langwieriges Aufarbeiten der Umsetzungsgemische notwendig. Die Betaine sind, was besonders wertvoll ist, gegen verdünnte Alkalien beständig und können in saurer wie in alkalischer Lösung als Netz-, M'asch- (insbesondere für Leinenwäsche), Emulgier-, Dispergier-, Egalisier- und Reinigungsmittel, und zwar in Form der anfallenden sauren Verbindungen oder als Salze des Kaliums; Natriums, Ammoniums oder organischer Basen angewendet werden. Gegebenenfalls kann die noch freie Carboxylgruppe auch mit Alkoholen verestert werden. Beispiel i 116,1 g (i Mol) Maleinsäure werden in Äther gelöst und einer Lösung von Sog g (i Mol) N-Hexadecylpiperidin in Äther unter Rühren zugegeben. Der ausfallende weiße Niederschlag wird filtriert und mit Äther gewaschen. Das saure maleinsaure N-Hexadecylpiperidin wird in einem Kolben im Ölbad so lange auf 13o ° erhitzt, bis eine herausgenommene Probe sich klar in Wasser löst und auf Zusatz von fo°/oiger Natronlauge keine. Fällung mehr gibt.The easy accessibility of these betaines, their implementation practical runs quantitatively, does not make a lengthy work-up of the conversion mixtures necessary. The betaines are, what is particularly valuable, against diluted alkalis resistant and can be used in acidic as well as in alkaline solution as mesh, M'asch (especially for Linen), emulsifying, dispersing, leveling and cleaning agents, namely in the form of the resulting acidic compounds or as salts of potassium; Sodium, Ammonium or organic bases are used. If necessary, it can still free carboxyl group can also be esterified with alcohols. Example i 116.1 g (i Mol) maleic acid are dissolved in ether and a solution of suction g (1 mol) N-hexadecylpiperidine added in ether with stirring. The white precipitate which separates out is filtered off and washed with ether. The acidic maleic acid N-Hexadecylpiperidin is in one The flask is heated to 130 ° in an oil bath until a sample is removed Clearly dissolves in water and none on the addition of fo% sodium hydroxide solution. Precipitation more gives.
Das hierbei entstandene Bernsteinsäurecetylpiperidinbetain kann in 2°/oiger wäßriger Lösung zum Waschen von Leinen verwendet werden.The resulting succinic acid cetylpiperidine betaine can be used in 2% aqueous solution can be used for washing linen.
Das saure maleinsaure Hexadecylpiperidin kann auch in Kohlenwasserstoffen, Alkoholen oder Ketonen gelöst am Rückflußkühler oder im Autoklaven erhitzt werden, bis die Umwandlung in das entsprechende Betain vollzogen ist. Beispie12 197 g Brombernsteinsäure werden in Äther gelöst und unter Rühren zu einer ätherischen Lösung von 6o g N-Dodecylisochinolintetrahydrid gegeben. - Der ausfallendeNiederschlagwird wie im Beispiel i aufgearbeitet und durch Erhitzen auf 12o bis 13o ° bis zur Klarlöslichkeit in Wasser in das Bernsteinsäuredodecylisochinolintetrahydridbetain umgewandelt. Dieses Kon-'-densationsprodukt zeigt in wäßriger Lösung jeeSeif eneigenschaften.The acidic maleic acid hexadecylpiperidine can also be found in hydrocarbons, Dissolved alcohols or ketones are heated on the reflux condenser or in an autoclave, until the conversion into the corresponding betaine has been completed. Example 12 197 g bromosuccinic acid are dissolved in ether and stirred into an ethereal solution of 6o g of N-dodecylisoquinoline tetrahydride given. - The precipitate is processed as in example i and through Heat to 12o to 13o ° until clear solubility in water in the succinic acid dodecylisoquinoline tetrahydride betaine converted. This condensation product shows very soap properties in aqueous solution.
Beispie13 144 g Maleinsäuremonoäthylester werden in Äther gelöst. Die Lösung gibt man unter Rühren in eine ätherische Lösung von 253 g N-Dodecylpiperidin. Es bildet sich das entsprechende saure Aminsalz, welches ausgefällt, abfiltriert und mit Äther gewaschen wird. Nunmehr erfolgt die Umlagerung des Aminsalzes zu dem Bernsteinsäureäthylesterdodecylpiperidinbetain durch Erhitzen im Ölbad auf etwa 13o ° *wie im Beispiel i. Das erhaltene Umlagerungsprodukt ist wasserlöslich und zeigt Seifeneigenschaften.Beispie13 144 g of maleic acid monoethyl ester are dissolved in ether. The solution is added with stirring to an ethereal solution of 253 g of N-dodecylpiperidine. The corresponding acidic amine salt is formed, which is precipitated and filtered off and washed with ether. The amine salt is now rearranged to form the Succinic acid ethyl ester dodecylpiperidine betaine by heating in an oil bath to approx 13o ° * as in example i. The rearrangement product obtained is soluble in water and shows soap properties.
Claims (1)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1937D0074370 DE688083C (en) | 1937-01-16 | 1937-01-16 | Process for the production of capillary-active, betaine-like compounds |
| CH204520D CH204520A (en) | 1937-01-16 | 1938-01-15 | Process for the preparation of a capillary active agent. |
| FR832102D FR832102A (en) | 1937-01-16 | 1938-01-15 | Process for the production of hair-acting agents and products obtained by this process |
| GB1553/38A GB509435A (en) | 1937-01-16 | 1938-01-17 | Improvements in or relating to the manufacture and use of compounds of the betaine type |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1937D0074370 DE688083C (en) | 1937-01-16 | 1937-01-16 | Process for the production of capillary-active, betaine-like compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE688083C true DE688083C (en) | 1940-02-12 |
Family
ID=89835936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1937D0074370 Expired DE688083C (en) | 1937-01-16 | 1937-01-16 | Process for the production of capillary-active, betaine-like compounds |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH204520A (en) |
| DE (1) | DE688083C (en) |
| FR (1) | FR832102A (en) |
| GB (1) | GB509435A (en) |
-
1937
- 1937-01-16 DE DE1937D0074370 patent/DE688083C/en not_active Expired
-
1938
- 1938-01-15 FR FR832102D patent/FR832102A/en not_active Expired
- 1938-01-15 CH CH204520D patent/CH204520A/en unknown
- 1938-01-17 GB GB1553/38A patent/GB509435A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB509435A (en) | 1939-07-17 |
| FR832102A (en) | 1938-09-22 |
| CH204520A (en) | 1939-05-15 |
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