US2460182A - Basic esters of aliphatic tertiary carboxylic acids - Google Patents
Basic esters of aliphatic tertiary carboxylic acids Download PDFInfo
- Publication number
- US2460182A US2460182A US549492A US54949244A US2460182A US 2460182 A US2460182 A US 2460182A US 549492 A US549492 A US 549492A US 54949244 A US54949244 A US 54949244A US 2460182 A US2460182 A US 2460182A
- Authority
- US
- United States
- Prior art keywords
- acetic acid
- esters
- carboxylic acids
- ester
- aliphatic tertiary
- 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
- 150000002148 esters Chemical class 0.000 title description 20
- 125000001931 aliphatic group Chemical group 0.000 title description 5
- 150000001735 carboxylic acids Chemical group 0.000 title description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- -1 isovaleric acid ester Chemical class 0.000 description 11
- 238000009835 boiling Methods 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000002168 ethanoic acid esters Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KQYRYPXQPKPVSP-UHFFFAOYSA-N 2-butylhexanoic acid Chemical compound CCCCC(C(O)=O)CCCC KQYRYPXQPKPVSP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- JPAMKBKLNCSGRD-UHFFFAOYSA-N 2,4-dimethyl-2-(2-methylpropyl)pentanoic acid Chemical compound CC(C)CC(C)(C(O)=O)CC(C)C JPAMKBKLNCSGRD-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000002276 neurotropic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- VKKTUDKKYOOLGG-UHFFFAOYSA-N 1-(diethylamino)propan-1-ol Chemical compound CCC(O)N(CC)CC VKKTUDKKYOOLGG-UHFFFAOYSA-N 0.000 description 1
- YQLAEHCLRXQXCI-UHFFFAOYSA-N 1-(ethylamino)-3-methylcyclohexan-1-ol Chemical compound CC1CC(CCC1)(O)NCC YQLAEHCLRXQXCI-UHFFFAOYSA-N 0.000 description 1
- GJZGYXVJHDAOAC-UHFFFAOYSA-N 2,2-diethylhexanoyl chloride Chemical compound CCCCC(CC)(CC)C(Cl)=O GJZGYXVJHDAOAC-UHFFFAOYSA-N 0.000 description 1
- HAUCDFONFDGDEM-UHFFFAOYSA-N 2,4-dimethyl-2-(2-methylpropyl)pentanoyl chloride Chemical compound CC(C)CC(C)(C(Cl)=O)CC(C)C HAUCDFONFDGDEM-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- LYIMSMCQBKXQDK-UHFFFAOYSA-N 2-ethyl-2-methylhexanoic acid Chemical compound CCCCC(C)(CC)C(O)=O LYIMSMCQBKXQDK-UHFFFAOYSA-N 0.000 description 1
- KQMKJGXDDZOKPF-UHFFFAOYSA-N 2-ethyl-2-methylhexanoyl chloride Chemical compound CCCCC(C)(CC)C(Cl)=O KQMKJGXDDZOKPF-UHFFFAOYSA-N 0.000 description 1
- JQRPEVZIJUBANB-UHFFFAOYSA-N 2-methyl-2-propylhexanoyl chloride Chemical compound CC(C(=O)Cl)(CCCC)CCC JQRPEVZIJUBANB-UHFFFAOYSA-N 0.000 description 1
- QDMJCNQWHZTJDK-UHFFFAOYSA-N 2-methyl-2-propylpentanoyl chloride Chemical compound CCCC(C)(C(Cl)=O)CCC QDMJCNQWHZTJDK-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000002560 therapeutic 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Definitions
- phenyl acetic acids and of their hydrogenation products have become known as compounds having neurotropic, atropine-like properties.
- R, R and R meaning the same or difierent saturated or unsaturated alkyl radicals.
- the tertiary trialkyl acetic acids which are used as starting material may be obtained by alkylating the nitrilesof monoor dialkyl acetonit'riles in the-presence of sodium amide according toZiegler, Annalen der Chemie, vol. 495, page 84- or German Patent 570,59i and subsequent hydrolysis of the so-obtained nitriles with an alcoholic solution of sodium or potassium hydroxide at temperatures ranging up to 180 C.
- Reactive esters of amino alcohols falling within thescope of the invention are especially esters withv hydrogen halide acids, with aryl sulfonic acids and the like.
- a further object of the invention consists in converting aliphatic tertiary carboxylic acids reactive derivatives of the. aliphatic: tertiary carboxylic acids, i. e. their halides, esters:v or
- halogen alkyl esters it is advantageous to react alkylene halogen hydrines withaliphatic tertiary carboxylic acids or with their halides, esters or anhydrides in the presence or absence of condensation agents or to react alkylene halogen hydrines or alkylene dihalides with salts of the said acids, the hydroxyl groups which may be present in the so-obtained compounds being subsequently replaced by halogen.
- The. basic esters claimed herein are colorless oils which, in form of their salts with inorganic or'organic acids, are soluble in water.
- Example 1 9 parts of methyl-di-n-propyl acetic acid chloride areadded, while stirring, to 6 parts of diethyl-amino ethanol and the mixture is heated, under stirring, for a short time to C.
- Theclear; yellowish-brown solution is treated, advantageously still Warm, with water and the aqueous. solution is extracted several times with.
- solvent is distilled oil. The. residue boils. at.
- the piperidino ethanol ester of methyl-di-npropyl acetic acid forms a hydrochloride of the melting point of 153-155 C.
- Example 2 16 parts of methyl ethyl-n-butyl acetic acid are heated for 24 hours to boiling, while stirring, with 14 parts of ,8-chloroethyl diethylamine and with 20 parts of potassium carbonate in 250 parts by volume of dry acetic acid ester. After cooling the potassium chloride is filtered by suction, the residue is washed with acetic acid ester and the combined acetic acid ester solutions are treated with dilute hydrochloric acid. The resulting acid solution is extracted with ether, then the base is freed by addition of a potassium carbonate solution and extracted with ether. After drying of the etheral solution the solvent is distilled off. The residue boils at 11 mm. pressure at 137-139 C. v
- esters are obtained with the correspond- Example 3 35 parts of diethyl-n-butyl acetic acid chloride are caused to react in the presence of pyridine with 1'7 parts of ethylene chlorohydrine. After complete reaction the mixture is extracted with ether and water, the ethereal solution is dried and the solvent distilled off. The residue is fractionated in vacuo and 20 parts of the so-obtained diethyl-n-butyl acetic acid-c-chloroethyl ester are interacted in the heat with 14 parts of piperidine. The mixture is extracted with ether and water. After having dried the ethereal solution the solvent is distilled off. The residue boils at 11 mm. pressure at 146149 C.
- esters When using the corresponding acid chlorides, there may be obtained for instance the following esters:
- Example 4- 10 parts of methyl-di-isobutyl acetic acid chloride are brought to interaction with 5 parts of dimethylamino propanol and worked up in the manner described in Example 1.
- the dimethylaminopropanol ester of the methyl-di-isobutyl acetic acid is obtained in form of a colorless oil having the boiling point at 13 mm. pressure of 146-149 C.
- a basic ester of an aliphatic tertiary carboxylic acid of the formula wherein A1 and A2 each represents a lower alkyl group and A1 and A2 together contain from 5 to 8 carbon atoms, X represents a divalent radical selected from the group consisting of -CH2.CH2--, CH2.CH2.CH2 and radicals, and Am stands for the radical of a secondary amine selected from the group consisting of lower dialkyl amines and piperidine.
- a basic ester of an aliphatic tertiary carb'oxylic acid of the formula A1 Az-('1OO-OXAni wherein A1 represents an alkyl radical containing at least 3 and at most 5 carbon atoms, A2 represents an alkyl radical containing at least 2 carbon atoms, and A1 and A2 together contain from 5 to 8 carbon atoms, X represents a divalent radical selected from the group consisting of -CH2.CH2, CH2.CH2.CH2 and CHz-CH:
- Am stands for the radical of a secondary amine selected from the group consisting of lower dialkyl amines and piperidine.
- the piperidinoethanol ester of methyl-di-npropyl acetic acid of the formula being a. colorless oil of the boiling point of 157 C. at 11 mm. pressure and forming a hydro- 5 chloride of the melting point of 153-l55 C., possessing valuable therapeutic properties.
- the dimethylaminopropanol ester of methyl-di-isobutyl acetic acid of the formula being a. colorless oil of the boiling point of 146- 149 C. at 13 mm. pressure, possessing valuable therapeutic properties.
- the diethylaminoethanolester of methyl-npropyl-n-butyl acetic acid of the formula being a colorless oil of the boiling point of 147- 148 C. at 12 mm. pressure, possessing valuable therapeutic roperties.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH245220T | 1943-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2460182A true US2460182A (en) | 1949-01-25 |
Family
ID=4464777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US549492A Expired - Lifetime US2460182A (en) | 1943-08-04 | 1944-08-14 | Basic esters of aliphatic tertiary carboxylic acids |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2460182A (fr) |
| BE (1) | BE457094A (fr) |
| CH (1) | CH245220A (fr) |
| FR (1) | FR906284A (fr) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019067060A1 (fr) * | 2017-09-29 | 2019-04-04 | Exxonmobil Chemical Patents Inc. | Composés esters, compositions d'huile lubrifiante les contenant et leurs procédés de fabrication |
| US10584083B2 (en) | 2017-09-29 | 2020-03-10 | Exxonmobile Chemical Patents Inc. | Neo-alcohol compounds, processes for making same and use thereof |
| US10597347B2 (en) | 2017-09-29 | 2020-03-24 | Exxonmobil Chemical Patents Inc. | Neo-acids and process for making the same |
| US10683464B2 (en) | 2017-09-29 | 2020-06-16 | Exxonmobil Chemical Patents Inc. | Ester compounds, lubricating oil compositions containing same and processes for making same |
| CN111344271A (zh) * | 2017-09-29 | 2020-06-26 | 埃克森美孚化学专利公司 | 新醇化合物、其制备方法及其用途 |
| US10711216B2 (en) | 2017-09-29 | 2020-07-14 | Exxonmobil Chemical Patents Inc. | Ester compounds, lubricating oil compositions containing same and processes for making same |
| WO2021123904A1 (fr) | 2019-12-17 | 2021-06-24 | Momentive Performance Materials Gmbh | Composés d'acide gras polymeres pour le traitement de substrats fibreux à base d'acides aminés, en particulier les cheveux |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2088144A2 (en) * | 1970-05-22 | 1972-01-07 | Lespagnol Albert | Aminopropyl esters of t-alkanoic acids - with spasmolytic hypotensive and sedative activity |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2223244A (en) * | 1937-06-23 | 1940-11-26 | Bohm Erich | Manufacture of stabilized animal and vegetable fats and oils |
-
1943
- 1943-08-04 CH CH245220D patent/CH245220A/de unknown
-
1944
- 1944-08-03 BE BE457094A patent/BE457094A/fr unknown
- 1944-08-03 FR FR906284D patent/FR906284A/fr not_active Expired
- 1944-08-14 US US549492A patent/US2460182A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2223244A (en) * | 1937-06-23 | 1940-11-26 | Bohm Erich | Manufacture of stabilized animal and vegetable fats and oils |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019067060A1 (fr) * | 2017-09-29 | 2019-04-04 | Exxonmobil Chemical Patents Inc. | Composés esters, compositions d'huile lubrifiante les contenant et leurs procédés de fabrication |
| US10584083B2 (en) | 2017-09-29 | 2020-03-10 | Exxonmobile Chemical Patents Inc. | Neo-alcohol compounds, processes for making same and use thereof |
| US10597347B2 (en) | 2017-09-29 | 2020-03-24 | Exxonmobil Chemical Patents Inc. | Neo-acids and process for making the same |
| US10683464B2 (en) | 2017-09-29 | 2020-06-16 | Exxonmobil Chemical Patents Inc. | Ester compounds, lubricating oil compositions containing same and processes for making same |
| CN111344271A (zh) * | 2017-09-29 | 2020-06-26 | 埃克森美孚化学专利公司 | 新醇化合物、其制备方法及其用途 |
| US10711216B2 (en) | 2017-09-29 | 2020-07-14 | Exxonmobil Chemical Patents Inc. | Ester compounds, lubricating oil compositions containing same and processes for making same |
| WO2021123904A1 (fr) | 2019-12-17 | 2021-06-24 | Momentive Performance Materials Gmbh | Composés d'acide gras polymeres pour le traitement de substrats fibreux à base d'acides aminés, en particulier les cheveux |
Also Published As
| Publication number | Publication date |
|---|---|
| CH245220A (de) | 1946-10-31 |
| BE457094A (fr) | 1944-09-30 |
| FR906284A (fr) | 1945-12-28 |
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