NO129572B - - Google Patents
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- Publication number
- NO129572B NO129572B NO691670A NO167069A NO129572B NO 129572 B NO129572 B NO 129572B NO 691670 A NO691670 A NO 691670A NO 167069 A NO167069 A NO 167069A NO 129572 B NO129572 B NO 129572B
- Authority
- NO
- Norway
- Prior art keywords
- isophorone
- acid
- mixture
- temperature
- column
- Prior art date
Links
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 88
- 239000000203 mixture Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 8
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 6
- 229950000244 sulfanilic acid Drugs 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000006838 isophorone group Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- -1 sulphanilic acid Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
Description
Fremgangsmåte til avfargning av rått isoforon. Procedure for decolorizing crude isophorone.
Det er kjent at isoforon kan frem-stilles av aceton, f. eks. ved opphetning ved overatmosfærisk trykk i nærvær av en alkalisk katalysator. Det fremstilte isoforon har imidlertid en ikke ønsket sterk ; gul farge. It is known that isophorone can be produced from acetone, e.g. by heating at superatmospheric pressure in the presence of an alkaline catalyst. However, the produced isophorone has an undesirable strength; yellow color.
Formålet med den foreliggende opp-finnelse er å skaffe en fremgangsmåte til avfarging av isoforon. The purpose of the present invention is to provide a method for decolorizing isophorone.
I henhold til oppfinnelsen består fremgangsmåten til avfarging av rått isoforon deri at man blander farget isoforon med en aromatisk sulfonsyre og avdestillerer isoforon fra blandingen, fortrinnsvis ved en temperatur fra 80—160° C. According to the invention, the method for decolorizing raw isophorone consists in mixing colored isophorone with an aromatic sulphonic acid and distilling isophorone from the mixture, preferably at a temperature of 80-160°C.
Det fargede isoforon som behandles i henhold til oppfinnelsen kan være et rått produkt som inneholder ca. 80 vektsprosent isoforon og som er fått ved å opphete aceton ved overatmosfærisk trykk i nærvær av en alkalisk katalysator. Det anvendte isoforon kan inneholde vann. Også fargede isoforoner som er fått fra andre kil-der kan avfarges i henhold til oppfinnelsen. The colored isophorone that is treated according to the invention can be a raw product containing approx. 80% by weight isophorone and which is obtained by heating acetone at superatmospheric pressure in the presence of an alkaline catalyst. The isophorone used may contain water. Colored isophorones obtained from other sources can also be decoloured according to the invention.
Avfargingen kan foregå uavhengig av The decolorization can take place independently of
eller i forbindelse med annen rensing av isoforonet. Behandling av isoforon kan ut-føres på et hvilket som helst egnet trinn av rensingen. Eksempelvis kan syren settes til fuktig isoforon som deretter kan renses og tørkes ved destillasjon. Alternativt kan syren settes til tørt isoforon som deretter blir destillert. or in connection with other purification of the isophorone. Treatment of isophorone can be carried out at any suitable stage of the purification. For example, the acid can be added to moist isophorone, which can then be purified and dried by distillation. Alternatively, the acid can be added to dry isophorone which is then distilled.
Den aromatiske sulfonsyre som anvendes i henhold til oppfinnelsen er fortrinnsvis p-toluol-sulfonsyre, men andre sulfonsyrer, f. eks. sulfanilsyre, kan også anvendes. Mengden av aromatisk syre i blandingen med isoforon bør hensiktsmes-sig være under 1 vektsprosent, fortrinnsvis 0,01—0,5 vektsprosent, beregnet på volumet av isoforonet. The aromatic sulphonic acid used according to the invention is preferably p-toluene sulphonic acid, but other sulphonic acids, e.g. sulphanilic acid, can also be used. The amount of aromatic acid in the mixture with isophorone should ideally be below 1% by weight, preferably 0.01-0.5% by weight, calculated on the volume of the isophorone.
Isoforonet kan destilleres fra blandingen ved anvendelse av hvilken som helst egnet type av destillasjonskolonner; fortrinnsvis anvendes det en fraksjonerings-kolonne. Fortrinnsvis blir blandingen av isoforon og den aromatiske sulfonsyre opp-hetet til en temperatur på 80—160° C for utførelse av destillasjonen. The isophorone can be distilled from the mixture using any suitable type of distillation column; preferably a fractionation column is used. Preferably, the mixture of isophorone and the aromatic sulphonic acid is heated to a temperature of 80-160° C to carry out the distillation.
Avfarging av isoforon i henhold til oppfinnelsen kan utføres helt til fullsten-dig avfarging, men prosessen kan også le-des slik at isoforonet blir bare delvis av-farget. Decolorization of isophorone according to the invention can be carried out until complete decolorization, but the process can also be directed so that the isophorone is only partially decolorized.
Fremgangsmåten i henhold til oppfinnelsen kan utføres porsjonsvis, men den kan også utføres på en delvis kontinuerlig måte, f. eks. ved kontinuerlig destillering av blandingen av isoforon og den aromatiske sulfonsyre. The method according to the invention can be carried out in portions, but it can also be carried out in a partially continuous manner, e.g. by continuous distillation of the mixture of isophorone and the aromatic sulphonic acid.
Isoforon har som kjent verdifulle egen-skaper som oppløsningsmiddel; det anvendes f. eks. som oppløsningsmiddel ved frem-stilling av trykksverte. As is known, isophorone has valuable properties as a solvent; it is used e.g. as a solvent in the production of printing ink.
I følgende eksempler belyses oppfinnelsen nærmere. Fargen av isoforon ble målt i Lovibond tintometer under anvendelse av en 2,5 cm celle. In the following examples, the invention is explained in more detail. The color of isophorone was measured in a Lovibond tintometer using a 2.5 cm cell.
Eksempel 1. Example 1.
Rått, fuktig isoforon, som var fremstilt fra aceton ved overatmosfærisk trykk i nærvær av en alkali-katalysator, ble fri-gjort for vann ved destillering ved et trykk på 15—20 mm kvikksølv. Det således erholdte rå, tørre isoforon ble blandet med p-toluol-sulfonsyre så man fikk en blanding som inneholdt 0,1 vektsprosent syre beregnet på volumet av isoforonet. Denne blanding ble innført i en mengde av 60 volumdeler pr. time ved et sted som be-fant seg i en avstand på 1/3 kolonnelengde fra bunnen av en kolonne som var pakket med Raschig-ringer. Ved bunnen av kolonnen var det anordnet en kjele med et utløp, og kolonnen var også utstyrt med tilbakeløpskjøling. Når kolonnen var, i re-gulær drifttilstand ble kjelens temperatur holdt på 135° C mens toppartiet hadde en temperatur på 87—90° C, tilbakeløpsfor-holdet var 1:1, og trykket ble holdt på 10 mm kvikksølv. Det erholdte isoforons farge var 0,8 enheter (gul). Crude, moist isophorone, which was prepared from acetone at superatmospheric pressure in the presence of an alkali catalyst, was freed from water by distillation at a pressure of 15-20 mm of mercury. The raw, dry isophorone thus obtained was mixed with p-toluenesulfonic acid so that a mixture containing 0.1% by weight of acid calculated on the volume of the isophorone was obtained. This mixture was introduced in an amount of 60 parts by volume per hour at a location located at a distance of 1/3 column length from the bottom of a column packed with Raschig rings. A boiler with an outlet was arranged at the bottom of the column, and the column was also equipped with reflux cooling. When the column was in regular operating condition, the boiler temperature was kept at 135° C while the top part had a temperature of 87-90° C, the reflux ratio was 1:1, and the pressure was kept at 10 mm of mercury. The color of the isophorone obtained was 0.8 units (yellow).
Eksempel 2. Example 2.
Rått, fuktig isoforon ble blandet med p-toluol-sulfonsyre så man fikk en blanding som inneholdt 0,2 vektsprosent syre beregnet på volumet av isoforon. Fra denne blanding ble vann fjernet ved destillasjon ved et trykk på 15—20 mm kvikksølv i 45 minutter. Det tørkede materiale ble destillert i det i eksempel 1 beskrevne destil-lasjonsapparat med en tilførsel på 75 volumdeler pr. time, en kjeletemperatur på 120—140° C, en topptemperatur på 80—85° C, et tilbakeløpsforhold på 1:1 og et trykk på 15—20 mm kvikksølv. Det erholdte isoforons farge var 0,2—0,5 enheter (gul). Raw, moist isophorone was mixed with p-toluenesulfonic acid to obtain a mixture containing 0.2% by weight of acid calculated on the volume of isophorone. From this mixture, water was removed by distillation at a pressure of 15-20 mm of mercury for 45 minutes. The dried material was distilled in the distillation apparatus described in example 1 with a supply of 75 parts by volume per hour, a boiler temperature of 120-140° C, a top temperature of 80-85° C, a reflux ratio of 1:1 and a pressure of 15-20 mm of mercury. The color of the isophorone obtained was 0.2-0.5 units (yellow).
Eksempel 3. Example 3.
Rått, fuktig isoforon ble blandet med p-toluol-sulfonsyre så man fikk en blanding som inneholdt 0,1 vektsprosent syre beregnet på isoforonets volum. Denne blanding ble behandlet ved den i eksempel 2 beskrevne fremgangsmåte idet man anvendte en tilførsel av 85 volumdeler pr. time, en kjeletemperatur på 130—135° C, en topptemperatur på 89—91° C, et til-bakeløpsforhold på 1:1 og et trykk på 10 mm kvikksølv. Det erholdte isoforon hadde en gulfarge på 0,5 enheter. Raw, moist isophorone was mixed with p-toluenesulfonic acid to obtain a mixture containing 0.1% by weight of acid calculated on the volume of the isophorone. This mixture was treated by the method described in example 2 using a supply of 85 parts by volume per hour, a boiler temperature of 130-135° C, a top temperature of 89-91° C, a flow-to-reflux ratio of 1:1 and a pressure of 10 mm of mercury. The isophorone obtained had a yellow color of 0.5 units.
Eksempel 4. Example 4.
Fremgangsmåten i eksempel 3 ble an-vendt på en blanding av isoforon og p-toluol-sulfonsyre som inneholdt 0,05 vektsprosent syre. Tilførselen var .60 volumdeler pr. time, kjeletemperaturen var 135° C, topptemperaturen var 85—88° C, og de øvrige arbeidsbetingelser var de samme. Det erholdte isoforon hadde en gulfarge på 0,7 enheter. The method in example 3 was applied to a mixture of isophorone and p-toluenesulfonic acid which contained 0.05% by weight of acid. The supply was .60 volume parts per hour, the boiler temperature was 135° C, the peak temperature was 85-88° C, and the other working conditions were the same. The isophorone obtained had a yellow color of 0.7 units.
Eksempel 5. Example 5.
Fremgangsmåten i eksempel 3 ble an-vendt med den unntakelse at sulfanilsyre ble blandet med rå, fuktige isoforon så man fikk en blanding som inneholdt 0,2 vektsprosent sulfanilsyre beregnet på volumet av isoforon. Denne blanding ble holdt på 100° C i en time og deretter av-vannet og filtrert. Tilførselen til destilla-sjonskolonnen var 100 volumdeler pr. time, kjeletemperaturen var 140—150° C, topptemperaturen var 82—98° C, tilbakeløps-forholdet var 3:1 og trykket varierte mel-lom 5 og 20 mm kvikksølv. Det erholdte isoforon hadde en gulfarge på 1,6 enheter. The procedure in example 3 was used with the exception that sulfanilic acid was mixed with raw, moist isophorone so that a mixture containing 0.2% by weight of sulfanilic acid calculated on the volume of isophorone was obtained. This mixture was kept at 100°C for one hour and then dewatered and filtered. The supply to the distillation column was 100 parts by volume per hour, the boiler temperature was 140-150° C, the top temperature was 82-98° C, the reflux ratio was 3:1 and the pressure varied between 5 and 20 mm of mercury. The isophorone obtained had a yellow color of 1.6 units.
Til forskjell fra fremgangsmåten i henhold til oppfinnelsen, slik som denne er beskrevet i de ovenstående eksempler 1—5, ble fremgangsmåten i eksempel 3 gjentatt uten tilstedeværelse av en aromatisk sulfonsyre. Tilførselen til kolonnen var 80 volumdeler pr. time, kjeletemperaturen var 140—158° C, tilbakeløpsforholdet var 1:1 og trykket 10 mm kvikksølv. Det erholdte isoforon hadde en gulfarge på 3,3 enheter. I et liknende forsøk hvor man anvendte en tilførsel til kolonnen på 50 volumdeler pr. time og en kjeletemperatur på 115—158° C hadde det erholdte isoforon en gulfarge på 3,9 enheter. In contrast to the method according to the invention, as described in the above examples 1-5, the method in example 3 was repeated without the presence of an aromatic sulphonic acid. The supply to the column was 80 parts by volume per hour, the boiler temperature was 140-158° C, the reflux ratio was 1:1 and the pressure 10 mm of mercury. The isophorone obtained had a yellow color of 3.3 units. In a similar experiment where a supply to the column of 50 volume parts per hour and a boiler temperature of 115-158° C, the isophorone obtained had a yellow color of 3.9 units.
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH637968A CH500189A (en) | 1968-04-29 | 1968-04-29 | Process for the preparation of new, substituted phenylalkanoic acids |
| CH1732968A CH507234A (en) | 1968-04-29 | 1968-11-20 | Process for the production of new, substituted alkanoic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129572B true NO129572B (en) | 1974-04-29 |
Family
ID=25699490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO691670A NO129572B (en) | 1968-04-29 | 1969-04-22 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3651084A (en) |
| JP (2) | JPS4827309B1 (en) |
| AT (5) | AT286976B (en) |
| BE (1) | BE732301A (en) |
| BG (5) | BG15206A3 (en) |
| CH (2) | CH500189A (en) |
| CS (4) | CS161851B2 (en) |
| DE (1) | DE1921651A1 (en) |
| DK (1) | DK125132C (en) |
| ES (4) | ES366545A1 (en) |
| FI (1) | FI50971C (en) |
| FR (1) | FR2007555A1 (en) |
| GB (1) | GB1264367A (en) |
| IE (1) | IE33116B1 (en) |
| IL (1) | IL32089A (en) |
| NL (1) | NL6906209A (en) |
| NO (1) | NO129572B (en) |
| PL (1) | PL69906B1 (en) |
| SE (1) | SE338994B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5834882A (en) * | 1981-08-25 | 1983-03-01 | Nitto Electric Ind Co Ltd | Laminated adhesive tape for double-side bonding |
| JPS6183275A (en) * | 1984-10-01 | 1986-04-26 | Kimurashin Kk | Production of double-sided adhesive tape |
| JPS6183276A (en) * | 1984-10-01 | 1986-04-26 | Kimurashin Kk | Double-sided adhesive tape |
| JPS6198784A (en) * | 1984-10-20 | 1986-05-17 | Kimurashin Kk | Double-coated adhesive tape |
| FI74723C (en) * | 1986-10-24 | 1988-03-10 | Yhtyneet Paperitehtaat Oy | HAEFTPRODUKT. |
-
1968
- 1968-04-29 CH CH637968A patent/CH500189A/en not_active IP Right Cessation
- 1968-11-20 CH CH1732968A patent/CH507234A/en not_active IP Right Cessation
-
1969
- 1969-04-22 SE SE05684/69A patent/SE338994B/xx unknown
- 1969-04-22 DK DK219769AA patent/DK125132C/en active
- 1969-04-22 FI FI691195A patent/FI50971C/en active
- 1969-04-22 US US818393A patent/US3651084A/en not_active Expired - Lifetime
- 1969-04-22 NL NL6906209A patent/NL6906209A/xx unknown
- 1969-04-22 NO NO691670A patent/NO129572B/no unknown
- 1969-04-28 IL IL6932089A patent/IL32089A/en unknown
- 1969-04-28 BG BG012132A patent/BG15206A3/en unknown
- 1969-04-28 GB GB2152369A patent/GB1264367A/en not_active Expired
- 1969-04-28 ES ES366545A patent/ES366545A1/en not_active Expired
- 1969-04-28 AT AT409069A patent/AT286976B/en active
- 1969-04-28 IE IE577/69A patent/IE33116B1/en unknown
- 1969-04-28 BG BG013039A patent/BG15547A3/en unknown
- 1969-04-28 CS CS3005A patent/CS161851B2/cs unknown
- 1969-04-28 AT AT189070A patent/AT290517B/en not_active IP Right Cessation
- 1969-04-28 CS CS7997*A patent/CS161852B2/cs unknown
- 1969-04-28 ES ES366546A patent/ES366546A1/en not_active Expired
- 1969-04-28 CS CS7998*A patent/CS161853B2/cs unknown
- 1969-04-28 DE DE19691921651 patent/DE1921651A1/en active Pending
- 1969-04-28 AT AT189370A patent/AT290520B/en not_active IP Right Cessation
- 1969-04-28 AT AT189270A patent/AT290519B/en not_active IP Right Cessation
- 1969-04-28 ES ES366544A patent/ES366544A1/en not_active Expired
- 1969-04-28 ES ES366547A patent/ES366547A1/en not_active Expired
- 1969-04-28 AT AT189170A patent/AT290518B/en not_active IP Right Cessation
- 1969-04-28 CS CS7999*A patent/CS161854B2/cs unknown
- 1969-04-28 PL PL1969133260A patent/PL69906B1/pl unknown
- 1969-04-29 FR FR6913602A patent/FR2007555A1/fr not_active Withdrawn
- 1969-04-29 BE BE732301D patent/BE732301A/xx unknown
- 1969-09-17 BG BG013037A patent/BG15752A3/en unknown
- 1969-09-17 BG BG013040A patent/BG15548A3/en unknown
- 1969-09-17 BG BG013038A patent/BG15546A3/en unknown
-
1971
- 1971-10-22 JP JP46083856A patent/JPS4827309B1/ja active Pending
- 1971-10-22 JP JP46083858A patent/JPS4813550B1/ja active Pending
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