BE457094A - éthers-sels basiques d'acides carboxyliques aliphatiques tertiaires et procédé de préparation de cès produits - Google Patents

éthers-sels basiques d'acides carboxyliques aliphatiques tertiaires et procédé de préparation de cès produits

Info

Publication number: BE457094A
Authority: BE; Belgium
Prior art keywords: sep; salts; ether; carboxylic acids; aliphatic carboxylic
Prior art date: 1943-08-04

Application number

BE457094A

Other languages

English (en)

French (fr)

Inventor

Ag J R Geigy

Original Assignee

Ag J R Geigy

Priority date (The priority date 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 date listed.)

1943-08-04

Filing date

1944-08-03

Publication date

1944-09-30

1944-08-03 Application filed by Ag J R Geigy filed Critical Ag J R Geigy

1944-09-30 Publication of BE457094A publication Critical patent/BE457094A/fr

Links

150000007933 aliphatic carboxylic acids Chemical group 0.000 title claims description 10
238000000034 method Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title description 2
239000002253 acid Substances 0.000 claims description 13
150000007513 acids Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
125000004103 aminoalkyl group Chemical group 0.000 claims 1
230000007717 exclusion Effects 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
238000009835 boiling Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
150000003839 salts Chemical class 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
150000002170 ethers Chemical class 0.000 description 4
-1 haloalkyl ether salts Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
RQNOFUZGXHSHOT-UHFFFAOYSA-N 1-(diethylamino)ethanol Chemical compound CCN(CC)C(C)O RQNOFUZGXHSHOT-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
IMHQFVGHBDXALM-UHFFFAOYSA-N 2,2-diethylhexanoic acid Chemical compound CCCCC(CC)(CC)C(O)=O IMHQFVGHBDXALM-UHFFFAOYSA-N 0.000 description 2
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
CUUQJONZHFARFJ-UHFFFAOYSA-N 2-methyl-2-propylhexanoic acid Chemical compound CCCCC(C)(C(O)=O)CCC CUUQJONZHFARFJ-UHFFFAOYSA-N 0.000 description 2
PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
150000001414 amino alcohols Chemical group 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000002921 anti-spasmodic effect Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
230000002276 neurotropic effect Effects 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-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
VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical compound C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 description 1
MADORZDTLHDDEN-UHFFFAOYSA-N 1-piperidin-1-ylethanol Chemical compound CC(O)N1CCCCC1 MADORZDTLHDDEN-UHFFFAOYSA-N 0.000 description 1
YIJAXVWJZJYWPI-UHFFFAOYSA-N 1-piperidin-1-ylpropan-1-ol Chemical compound CCC(O)N1CCCCC1 YIJAXVWJZJYWPI-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
DNUYOWCKBJFOGS-UHFFFAOYSA-N 2-[[10-(2,2-dicarboxyethyl)anthracen-9-yl]methyl]propanedioic acid Chemical compound C1=CC=C2C(CC(C(=O)O)C(O)=O)=C(C=CC=C3)C3=C(CC(C(O)=O)C(O)=O)C2=C1 DNUYOWCKBJFOGS-UHFFFAOYSA-N 0.000 description 1
KQYRYPXQPKPVSP-UHFFFAOYSA-N 2-butylhexanoic acid Chemical compound CCCCC(C(O)=O)CCCC KQYRYPXQPKPVSP-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
BSUKKOMNQGNSGP-UHFFFAOYSA-N 2-ethylidenehexanoic acid Chemical compound CCCCC(=CC)C(O)=O BSUKKOMNQGNSGP-UHFFFAOYSA-N 0.000 description 1
GRYMWKBWWHJCGT-UHFFFAOYSA-N 2-methyl-2-(2-methylpropyl)hexanoic acid Chemical compound CC(C(=O)O)(CC(C)C)CCCC GRYMWKBWWHJCGT-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
YOWSYKCRNIREGL-UHFFFAOYSA-N 3-(diethylamino)-2,2-dimethylpropan-1-ol Chemical compound CCN(CC)CC(C)(C)CO YOWSYKCRNIREGL-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
229930003347 Atropine Natural products 0.000 description 1
YNJOFNGWDAYRAA-UHFFFAOYSA-N Cl.C(C)N(CC)C(CC)O Chemical compound Cl.C(C)N(CC)C(CC)O YNJOFNGWDAYRAA-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
JACRWUWPXAESPB-QMMMGPOBSA-N Tropic acid Natural products OC[C@H](C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-QMMMGPOBSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 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
UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
IJFXRHURBJZNAO-UHFFFAOYSA-N meta--hydroxybenzoic acid Natural products OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 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
150000003335 secondary amines Chemical class 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BE457094A 1943-08-04 1944-08-03 éthers-sels basiques d'acides carboxyliques aliphatiques tertiaires et procédé de préparation de cès produits BE457094A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH245220T		1943-08-04

Publications (1)

Publication Number	Publication Date
BE457094A true BE457094A (fr)	1944-09-30

Family

ID=4464777

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE457094A BE457094A (fr)	1943-08-04	1944-08-03	éthers-sels basiques d'acides carboxyliques aliphatiques tertiaires et procédé de préparation de cès produits

Country Status (4)

Country	Link
US (1)	US2460182A (de)
BE (1)	BE457094A (de)
CH (1)	CH245220A (de)
FR (1)	FR906284A (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
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
US10584083B2 (en)	2017-09-29	2020-03-10	Exxonmobile Chemical Patents Inc.	Neo-alcohol compounds, processes for making same and use thereof
EP3688125B1 (de) *	2017-09-29	2023-10-25	ExxonMobil Chemical Patents Inc.	Esterverbindungen zur verwendung als basisflüssigkeit in schmierölzusammensetzungen
US10683464B2 (en)	2017-09-29	2020-06-16	Exxonmobil Chemical Patents Inc.	Ester compounds, lubricating oil compositions containing same and processes for making same
US10597347B2 (en)	2017-09-29	2020-03-24	Exxonmobil Chemical Patents Inc.	Neo-acids and process for making the same
US10711216B2 (en)	2017-09-29	2020-07-14	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
JP2023506846A (ja)	2019-12-17	2023-02-20	モメンティブパフォーマンスマテリアルズゲーエムベーハー	繊維状アミノ酸ベースの基質、特に毛髪のトリートメントのための高分子脂肪酸化合物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
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 FR FR906284D patent/FR906284A/fr not_active Expired
- 1944-08-03 BE BE457094A patent/BE457094A/fr unknown
- 1944-08-14 US US549492A patent/US2460182A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CH245220A (de)	1946-10-31
US2460182A (en)	1949-01-25
FR906284A (fr)	1945-12-28

Publication	Publication Date	Title
BE457094A (fr)	1944-09-30	éthers-sels basiques d'acides carboxyliques aliphatiques tertiaires et procédé de préparation de cès produits
Winslow et al.	1961	Cyclic Ether Formation by Bis [(1-hydroxyethyl) cyclopentadienyl] iron
US2192840A (en)	1940-03-05	Method of preparing quinuclidine and derivatives thereof
BE457093A (fr)	1944-09-30	éthers-sels basiques d'acides mono-alcoyl-isobutyl-acétiques et procédé de préparation de ces produits
US2336093A (en)	1943-12-07	1-o-hydroxyphenoxy-3-alkoxy-2-propanols and/or-2-propanones and their manufacture
US2501858A (en)	1950-03-28	4'(beta-ethyl)-morpholine ester of nicotinic acid and its production
US2262544A (en)	1941-11-11	Soluble sulphanilamide derivatives and process for making them
JPS59141581A (ja)	1984-08-14	リボフラビンの改良製造法
US957633A (en)	1910-05-10	Ester from chaulmoogra-oil.
US2340268A (en)	1944-01-25	Esters of nitrohydroxy compounds
US2089348A (en)	1937-08-10	Process for the manufacture of amino sulphonic acids
US1336952A (en)	1920-04-13	Chmical
CH341165A (fr)	1959-09-30	Procédé de préparation de N-désacétyl-O-déméthylthiocolchicéines
FR2509309A1 (fr)	1983-01-14	Derives de theophylline substitues en position 7
US1457675A (en)	1923-06-05	Pharmaceutical product
US3074956A (en)	1963-01-22	Oxazoline compounds and method for producing same
Hammick et al.	1922	CCLXXXIII.—Preparation of sodium and potassium phthalimide
US858446A (en)	1907-07-02	Organic iodin preparation.
BE457027A (de)	1944-08-23
CH438271A (fr)	1967-06-30	Procédé de préparation de dérivés de l'acide hydroxycinnamique
Hahn et al.	1932	TYROSINE-N-ACETIC ACID: INTRODUCING A NEW GENERAL METHOD FOR PREPARING SYMMETRICAL AND ASYMMETRICAL IMINO DIBASIC ACIDS
Robinson et al.	1937	243. Experiments on the synthesis of substances related to the sterols. Part XVII. 8-Methylhydrindan-1-one
JPS6225133B2 (de)	1987-06-01
CH333915A (fr)	1958-11-15	Procédé de préparation de sels d'acides dérivés de l'acide thioglycolique
CH200185A (fr)	1938-09-30	Procédé de préparation de l'alpha-phényl-n-valérate du diéthylaminoéthanol.