NO120594B - - Google Patents
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- NO120594B NO120594B NO15695465A NO15695465A NO120594B NO 120594 B NO120594 B NO 120594B NO 15695465 A NO15695465 A NO 15695465A NO 15695465 A NO15695465 A NO 15695465A NO 120594 B NO120594 B NO 120594B
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- methylamine
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- phenylmaleic
- temperature
- reaction
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 21
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- -1 phenylmaleic acid monomethylamide Chemical compound 0.000 claims description 8
- QZYCWJVSPFQUQC-UHFFFAOYSA-N 3-phenylfuran-2,5-dione Chemical compound O=C1OC(=O)C(C=2C=CC=CC=2)=C1 QZYCWJVSPFQUQC-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- IDSFKFXFMNGXCK-UHFFFAOYSA-N 1-(4-Methylphenyl)pyrrolidine-2,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)CCC1=O IDSFKFXFMNGXCK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000000250 methylamino group Chemical class [H]N(*)C([H])([H])[H] 0.000 description 6
- CQNPSIAJXGEDQS-VURMDHGXSA-N (z)-2-phenylbut-2-enedioic acid Chemical compound OC(=O)\C=C(/C(O)=O)C1=CC=CC=C1 CQNPSIAJXGEDQS-VURMDHGXSA-N 0.000 description 5
- WLWFNJKHKGIJNW-UHFFFAOYSA-N Phensuximide Chemical compound O=C1N(C)C(=O)CC1C1=CC=CC=C1 WLWFNJKHKGIJNW-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- LVFFZQQWIZURIO-UHFFFAOYSA-N 2-phenylbutanedioic acid Chemical compound OC(=O)CC(C(O)=O)C1=CC=CC=C1 LVFFZQQWIZURIO-UHFFFAOYSA-N 0.000 description 2
- HDFKMLFDDYWABF-UHFFFAOYSA-N 3-phenyloxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1=CC=CC=C1 HDFKMLFDDYWABF-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MYANGMBHBNYNQU-UHFFFAOYSA-N 4-(methylamino)-4-oxo-3-phenylbutanoic acid Chemical compound CNC(=O)C(CC(O)=O)C1=CC=CC=C1 MYANGMBHBNYNQU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010034759 Petit mal epilepsy Diseases 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/22—Tricarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/24—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms containing more than three carboxyl groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
- A61Q1/06—Lipsticks
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q9/00—Preparations for removing hair or for aiding hair removal
- A61Q9/02—Shaving preparations
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- Emergency Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Fremgangsmåte til fremstilling av N-metyl-«-fen<y>lsuccininiid. Process for the preparation of N-methyl-«-phen<y>lsuccininiide.
Foreliggende oppfinnelse angår en fremgangsmåte til fremstilling av N-metyl-a-fenylsuccinimid. The present invention relates to a method for the production of N-methyl-α-phenylsuccinimide.
N-metyl-a-fenylsuccinimid er nylig N-methyl-α-phenylsuccinimide is recent
blitt et meget verdifullt preparat for be-handling av mildere former for epilepsi (petit mal). Ifølge U.S. patent 2 643 528 kan denne forbindelse fremstilles av fe-nylravsyre eller fenylravsyreanhydrid ved reaksjon med metylamin og oppvarmning av den forbindelse man får herved. De utbytter som kan oppnåes ved denne metode er omkring 65 pst. av det teoretiske. En videre ulempe som metoden er beheftet med er at den krever bruken av fenylrav-syre eller fenylravsyreanhydrid som begge er temmelig kostbare utgangsmaterialer. has become a very valuable preparation for the treatment of milder forms of epilepsy (petit mal). According to the U.S. patent 2 643 528, this compound can be prepared from phenylsuccinic acid or phenylsuccinic anhydride by reaction with methylamine and heating the compound obtained thereby. The yields that can be achieved by this method are around 65 per cent of the theoretical. A further disadvantage of the method is that it requires the use of phenylsuccinic acid or phenylsuccinic anhydride, both of which are rather expensive starting materials.
Ved hjelp av foreliggende oppfinnelse By means of the present invention
skaffes der en fremgangsmåte til fremstilling av N-metyl-a-fenylsuccinimid fra lett tilgjengelige og billige utgangsmaterialer og med høyere utbytter enn dem som i alminnelighet fåes ved bruken av den kjente metode for fremstilling av N-metyl-a-fenylsuccinimid. a method for the production of N-methyl-a-phenylsuccinimide from readily available and cheap starting materials and with higher yields than those generally obtained by using the known method for the production of N-methyl-a-phenylsuccinimide is obtained there.
Fremgangsmåten ifølge oppfinnelsen The method according to the invention
er i sine hovedtrekk karakterisert ved at man lar fenylmaleinsyreanhydrid reagere med minst én ekvivalent mengde metylamin ved en temperatur under 45° C hvorved man får fenylmaleinsyrens monometylamid, og at man reduserer den alifatiske dobbeltbinding som er til stede i dette monometylamid og oppvarmer den herved erholdte forbindelse til en temperatur over 100° C. is characterized in its main features by allowing phenylmaleic anhydride to react with at least one equivalent amount of methylamine at a temperature below 45° C, whereby phenylmaleic acid's monomethylamide is obtained, and by reducing the aliphatic double bond present in this monomethylamide and heating the compound thus obtained to a temperature above 100°C.
Ved utførelsen av reaksjonen mellom In carrying out the reaction between
fenylmaleinsyreanhydrid og metylamin phenylmaleic anhydride and methylamine
bruker man som nevnt minst én ekvivalent metylamin. Når der brukes en ekvivalent av metylamin, får man som mellomprodukt fenylmaleinsyrens monometylamid. Bruker man mere enn én ekvivalent metylamin, får man som mellomprodukt enten en blanding av den nevnte syre og metylaminsaltet eller metylaminsaltet av denne syre. Mellomproduktets nøyak-tige natur er ikke av avgjørende betyd-ning da det i de fleste tilfelle ikke isoleres eller renses på noen måte før man ut-fører det neste trin i fremgangsmåten. For enkelhets skyld betegnes her det nevnte mellomprodukt med «fenylmaleinsyrens monometylamid», idet dette uttrykk er slik å forstå at det også omfatter metylaminsaltet og en blanding av metylaminsaltet og den fri syre så vel som den fri syre i seg selv. as mentioned, at least one equivalent of methylamine is used. When an equivalent of methylamine is used, phenylmaleic acid monomethylamide is obtained as an intermediate. If more than one equivalent of methylamine is used, the intermediate product is either a mixture of the aforementioned acid and the methylamine salt or the methylamine salt of this acid. The exact nature of the intermediate product is not of decisive importance as in most cases it is not isolated or purified in any way before carrying out the next step in the process. For the sake of simplicity, the aforementioned intermediate is referred to here as "phenylmaleic acid monomethylamide", as this term is to be understood as including the methylamine salt and a mixture of the methylamine salt and the free acid as well as the free acid itself.
Fortrinsvis brukes der ved reaksjo-nens utførelse minst to ekvivalenter metylamin for hver ekvivalent fenylmalein-syre. Som ovenfor angitt bør reaksjonen utføres ved en temperatur under 45° C. Fra synspunktet høyt utbytte og unngå-else av sidereaksjoner foretrekkes det å bruke temperaturer mellom 0° C og 30° C. Preferably, when carrying out the reaction, at least two equivalents of methylamine are used for each equivalent of phenylmaleic acid. As stated above, the reaction should be carried out at a temperature below 45° C. From the point of view of high yield and avoidance of side reactions, it is preferred to use temperatures between 0° C and 30° C.
Reaksjonen kan utføres i vann, i et organisk oppløsningsmiddel eller i en blanding av vann og et organisk oppløs-ningsmiddel som er blandbart med vann. Blant de oppløsningsmidler som foruten vann kan brukes, er lavere alifatiske alkoholer som metanol, etanol og isopropanol, cykliske etere som dioksan, estere som etylacetat, samt vandige blandinger av de nevnte stoffer. Det foretrukne oppløs-ningsmiddel er, særlig når man bruker to ekvivalenter metylamin, vann fordi det selvfølgelig er det billigste. Reaksjonen foregår raskt og er i alminnelighet full-stendig i løpet av noen få minutter. The reaction can be carried out in water, in an organic solvent or in a mixture of water and an organic solvent which is miscible with water. Among the solvents that can be used in addition to water are lower aliphatic alcohols such as methanol, ethanol and isopropanol, cyclic ethers such as dioxane, esters such as ethyl acetate, and aqueous mixtures of the aforementioned substances. The preferred solvent is, especially when two equivalents of methylamine are used, water because it is of course the cheapest. The reaction takes place quickly and is generally complete within a few minutes.
Det annet trinn av fremgangsmåten, The second step of the procedure,
dvs. reduksjonen av den alifatiske dobbeltbinding i fenylmaleinsyrens monometylamid, utføres fortrinsvis under anven- i.e. the reduction of the aliphatic double bond in the monomethylamide of phenylmaleic acid is preferably carried out using
delse av gassformig hydrogen og en hydreringskatalysator bestående av et metall. splitting gaseous hydrogen and a hydrogenation catalyst consisting of a metal.
I den foretrukne utførelsesform for fremgangsmåten isoleres ikke fenylmaleinsy- In the preferred embodiment of the method, phenylmaleic acid is not isolated
rens nionometylamid etter fullførelsen av det første trinn i fremgangsmåten, men reaksjonsblandingen brukes direkte i re-duksjonstrinnet. Hvis mellomproduktet isoleres, kan reduksjonen utføres i vann, purify nionomethylamide after completion of the first step of the process, but the reaction mixture is used directly in the reduction step. If the intermediate is isolated, the reduction can be carried out in water,
lavere alifatiske alkoholer, estere av lavere alifatiske syrer, cykliske etere eller van- lower aliphatic alcohols, esters of lower aliphatic acids, cyclic ethers or water-
dige blandinger av disse stoffer. Når mellomproduktet er metylaminsaltet, foretrek- rich mixtures of these substances. When the intermediate is the methylamine salt, preferably
kes det å bruke vann som oppløsningsmid- is it possible to use water as a solvent
del, og når mellomproduktet er en fri syre, part, and when the intermediate is a free acid,
er det foretrukne oppløsningsmiddel en blanding av vann og en alkohol. Som hydreringskatalysator gir Raney-nikkel og edelmetallkatalysatorer som platina-oksyd særlig gode resultater. Hydreringen kan utføres ved temperaturer mellom 15 og 100° C. Det gassformige hydrogens trykk er ikke særlig kritisk, og der kan brukes hvilket som helst trykk fra én atmosfære til hundre atmosfærer eller mere. Man får gode resultater med hydrogentrykk på the preferred solvent is a mixture of water and an alcohol. As a hydrogenation catalyst, Raney nickel and noble metal catalysts such as platinum oxide give particularly good results. The hydrogenation can be carried out at temperatures between 15 and 100° C. The pressure of the gaseous hydrogen is not particularly critical, and any pressure from one atmosphere to a hundred atmospheres or more can be used. You get good results with hydrogen pressure on
2,5 til 6 atmosfærer og følgelig er det ikke nødvendig å bruke høyere trykk. 2.5 to 6 atmospheres and consequently it is not necessary to use higher pressures.
Det tredje trinn i fremgangsmåten, The third step in the procedure,
dvs. cykliseringen av det reduserte pro- i.e. the cyclization of the reduced pro-
dukt (fenylravsyrens monometylamid, en blanding av denne syre og metylaminsaltet eller syrens metylaminsalt) til det ønskede N-metyl-a-fenylsuccinimid utføres ved å oppvarme monometylamidforbindelsen til en temperatur over 100° C. Den foretruk- product (phenylsuccinic acid monomethylamide, a mixture of this acid and the methylamine salt or the acid's methylamine salt) to the desired N-methyl-α-phenylsuccinimide is carried out by heating the monomethylamide compound to a temperature above 100° C. The preferred
ne temperatur for denne reaksjon er fra 120 til 190° C. Dette trinn i fremgangsmå- temperature for this reaction is from 120 to 190° C. This step in the procedure
ten utføres bekvemmest ved å fjerne hyd-reringskatalysatoren fra reaksjonsblandin- is most conveniently carried out by removing the hydrogenation catalyst from the reaction mixture
gen som fåes i fremgangsmåtens annet trinn, avdestillere oppløsningsmidlene fra reaksjonsblandingen og oppvarme den mo-nometylamidforbindelse man får som re-siduum. Denne oppvarmning kan utføres i fravær av oppløsningsmidler eller om øn- gene that is obtained in the second step of the method, distill off the solvents from the reaction mixture and heat the monomethylamide compound that is obtained as a residue. This heating can be carried out in the absence of solvents or if desired
skes i et oppløsningsmiddel med koke- is done in a solvent with boiling
punkt over 100° C. point above 100° C.
I det følgende beskrives som eksemp- In the following, it is described as an example
ler to utførelsesformer for oppfinnelsen. shows two embodiments of the invention.
Eksempel 1: Example 1:
4 g fenylmaleinsyreanhydrid oppløses i 75 ml koldt vann inneholdende 8 ml 40 Dissolve 4 g of phenylmaleic anhydride in 75 ml of cold water containing 8 ml of 40
pst. metylamin. Når alt er oppløst, tilset- pst methylamine. When everything is dissolved, add-
tes 0,5 g Raney-nikkel hydreringskatalysa- tes 0.5 g Raney nickel hydrogenation catalysis
tor, og blandingen rystes i et lukket kar med gassformig hydrogen under et trykk på 3,4 kg/cm2 inntil absorpsjonen av hyd- tor, and the mixture is shaken in a closed vessel with gaseous hydrogen under a pressure of 3.4 kg/cm2 until the absorption of hyd-
rogen opphører. Derpå avblåses trykket, roe ceases. The pressure is then blown off,
og hydreringskatalysator en fjernes fra oppløsningen ved filtrering. Det klare fil- and the hydrogenation catalyst is removed from the solution by filtration. The clear file-
trat inndampes til tørrhet og residuet oppvarmes inntil temperaturen i massens indre når omkring 180° C. Residuet av- tray is evaporated to dryness and the residue is heated until the temperature in the interior of the mass reaches around 180° C. The residue
kjøles, tas opp i og krystalliseres fra 80 cooled, taken up in and crystallized from 80
pst.'s etanol hvorved man får 3,7 g N-metyl-a-fenylsuccinimid med smeltepunkt 70—72° C. Utbyttet er 85 pst. av det teo- percent ethanol, whereby 3.7 g of N-methyl-a-phenylsuccinimide with a melting point of 70-72° C is obtained. The yield is 85 percent of the thio-
retiske. rhetic.
Eksempel 2: Example 2:
4 g fenylmaleinsyreanhydrid tilsettes til 60 ml koldt vann inneholdende 7 ml 40 pst.'s vandig metylamin og som er 4 g of phenylmaleic anhydride is added to 60 ml of cold water containing 7 ml of 40% aqueous methylamine and which is
blandet med is. Suspensjonen omrøres inntil alt er oppløst, hvorpå der tilsettes 100 mg platina-oksyd-hydreringskatalysa- mixed with ice. The suspension is stirred until everything is dissolved, after which 100 mg of platinum oxide hydrogenation catalyst is added.
tor. Blandingen rystes i et lukket kar med gassformig hydrogen under et trykk på dare. The mixture is shaken in a closed vessel with gaseous hydrogen under a pressure of
3,15 kg/cm* inntil absorpsjonen av hydro- 3.15 kg/cm* until the absorption of hydro-
gen opphører. Trykket blåses av, og hyd-reringskatalysatoren fjernes ved filtrering. Filtratet inndampes til tørrhet, og residuet oppvarmes inntil massens temperatur blir omkring 180° C. Residuet avkjøles, opp- the gene ceases. The pressure is blown off, and the hydrogenation catalyst is removed by filtration. The filtrate is evaporated to dryness, and the residue is heated until the temperature of the mass is around 180° C. The residue is cooled, heated
løses i 8 ml varm etanol, og oppløsningen avfarves med trekull. Trekullet fjernes, 4 dissolve in 8 ml of hot ethanol, and the solution is decolorized with charcoal. The charcoal is removed, 4
ml varmt vann tilsettes til filtratet, og opp-løsningen avkjøles. Det ønskede N-metyl-a-fenylsuccinimid oppsamles og tørres. Utbyttet er 3,5 g eller 81 pst. av det teoretiske. Produktets smeltepunkt er 70— ml of warm water is added to the filtrate, and the solution is cooled. The desired N-methyl-α-phenylsuccinimide is collected and dried. The yield is 3.5 g or 81 per cent of the theoretical. The product's melting point is 70—
72° C. 72° C.
Fenylmaleinsyreanhydridet som ut- The phenylmaleic anhydride which ex-
gjør et av utgangsmaterialene i fremgangs- makes one of the starting materials in progress
måten ifølge oppfinnelsen kan fremstilles lett og billig ved å la maleinsyreanhydrid, benzen og klor innvirke på hverandre un- the method according to the invention can be produced easily and cheaply by allowing maleic anhydride, benzene and chlorine to act on each other un-
der bestråling med ultrafiolett lys. where irradiation with ultraviolet light.
Claims (5)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB816664A GB1096523A (en) | 1964-02-27 | 1964-02-27 | Cosmetic composition |
Publications (1)
Publication Number | Publication Date |
---|---|
NO120594B true NO120594B (en) | 1970-11-09 |
Family
ID=9847049
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO15695465A NO120594B (en) | 1964-02-27 | 1965-02-26 |
Country Status (13)
Country | Link |
---|---|
AT (1) | AT272523B (en) |
BE (1) | BE660349A (en) |
CH (1) | CH463021A (en) |
DE (1) | DE1286253B (en) |
DK (1) | DK111974B (en) |
FI (1) | FI45205B (en) |
FR (1) | FR1447188A (en) |
GB (1) | GB1096523A (en) |
IT (1) | IT943010B (en) |
LU (1) | LU48083A1 (en) |
NL (1) | NL6502355A (en) |
NO (1) | NO120594B (en) |
SE (1) | SE322019B (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4143160A (en) * | 1974-01-29 | 1979-03-06 | Henkel Kommanditgesellschaft Auf Aktien | Process for moisturing the skin |
DE2404047A1 (en) * | 1974-01-29 | 1975-08-14 | Henkel & Cie Gmbh | SKIN CARE AND SKIN PROTECTION PRODUCTS WITH A CONTENT OF SKIN MOISTURIZERS |
JPS5520716A (en) * | 1978-07-31 | 1980-02-14 | Kao Corp | Hair rinse composition |
CA1144573A (en) * | 1979-04-04 | 1983-04-12 | Edgar R. Rogier | High molecular weight bis(hydroxymethyl) alcohols |
US4582946A (en) * | 1979-10-04 | 1986-04-15 | Henkel Corporation | Polyhydric alcohols |
DE3315469A1 (en) * | 1983-04-28 | 1984-10-31 | Hoechst Ag, 6230 Frankfurt | HARDENING COMPONENT FOR SYNTHETIC RESINS CONTAINING GROUPS APPROPRIATE FOR AMID OR ESTER FORMATION WITH CARBONIC ACIDS |
DE3417441A1 (en) * | 1984-05-11 | 1985-11-14 | Hoechst Ag, 6230 Frankfurt | HARDENING COMPONENT FOR SYNTHETIC RESINS CONTAINING GROUPS APPROPRIATE FOR AMID OR ESTER FORMATION WITH CARBONIC ACIDS |
DE4234744A1 (en) * | 1992-10-15 | 1994-04-21 | Wella Ag | Hair care products |
JP4210614B2 (en) * | 2004-03-25 | 2009-01-21 | 花王株式会社 | Hair cosmetics |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2182178A (en) * | 1936-03-21 | 1939-12-05 | Ig Farbenindustrie Ag | Derivative of substituted succinic acids |
US2283214A (en) * | 1937-12-24 | 1942-05-19 | Monsanto Chemicals | Washing, wetting, and emulsifying agent |
US2360426A (en) * | 1942-02-12 | 1944-10-17 | Monsanto Chemicals | Production of alkene-succinic acids |
US2380699A (en) * | 1942-03-02 | 1945-07-31 | Monsanto Chemicals | Monoalkenyl-succinic acid mono-ester salts |
-
1964
- 1964-02-27 GB GB816664A patent/GB1096523A/en not_active Expired
-
1965
- 1965-02-25 NL NL6502355A patent/NL6502355A/xx unknown
- 1965-02-25 FI FI46265A patent/FI45205B/fi active
- 1965-02-26 NO NO15695465A patent/NO120594B/no unknown
- 1965-02-26 CH CH265865A patent/CH463021A/en unknown
- 1965-02-26 BE BE660349A patent/BE660349A/xx unknown
- 1965-02-26 DE DE1965U0011483 patent/DE1286253B/en active Pending
- 1965-02-26 SE SE250365A patent/SE322019B/xx unknown
- 1965-02-26 AT AT170465A patent/AT272523B/en active
- 1965-02-26 FR FR7234A patent/FR1447188A/en not_active Expired
- 1965-02-26 DK DK102965A patent/DK111974B/en unknown
- 1965-02-26 LU LU48083D patent/LU48083A1/xx unknown
- 1965-02-26 IT IT80165A patent/IT943010B/en active
Also Published As
Publication number | Publication date |
---|---|
NL6502355A (en) | 1965-08-30 |
IT943010B (en) | 1973-04-02 |
DK111974B (en) | 1968-10-28 |
SE322019B (en) | 1970-03-23 |
LU48083A1 (en) | 1965-08-26 |
CH463021A (en) | 1968-09-30 |
FR1447188A (en) | 1966-07-29 |
DE1286253B (en) | 1969-01-02 |
AT272523B (en) | 1969-07-10 |
GB1096523A (en) | 1967-12-29 |
BE660349A (en) | 1965-08-26 |
FI45205B (en) | 1971-12-31 |
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