DE1150671B - Process for the production of pure butenols - Google Patents
Process for the production of pure butenolsInfo
- Publication number
- DE1150671B DE1150671B DEC25872A DEC0025872A DE1150671B DE 1150671 B DE1150671 B DE 1150671B DE C25872 A DEC25872 A DE C25872A DE C0025872 A DEC0025872 A DE C0025872A DE 1150671 B DE1150671 B DE 1150671B
- Authority
- DE
- Germany
- Prior art keywords
- butenols
- pure
- acetates
- butylene glycol
- production
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- MPAGVACEWQNVQO-UHFFFAOYSA-N 3-acetyloxybutyl acetate Chemical compound CC(=O)OC(C)CCOC(C)=O MPAGVACEWQNVQO-UHFFFAOYSA-N 0.000 description 8
- -1 butenol acetates Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- WNHXJHGRIHUOTG-ONEGZZNKSA-N [(e)-but-2-enyl] acetate Chemical compound C\C=C\COC(C)=O WNHXJHGRIHUOTG-ONEGZZNKSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 230000002942 anti-growth Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- LYWCPTCPTWCZSZ-UHFFFAOYSA-N but-3-en-2-yl acetate Chemical compound C=CC(C)OC(C)=O LYWCPTCPTWCZSZ-UHFFFAOYSA-N 0.000 description 1
- IEKXSSZASGLISC-UHFFFAOYSA-N but-3-enyl acetate Chemical compound CC(=O)OCCC=C IEKXSSZASGLISC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung reiner Butenole Bekanntlich lassen sich Butenole durch Wasserabspaltung aus 1,3-Butylenglykol in flüssiger Phase erhalten. Bei diesen Verfahren entstehen, teilweise ganz überwiegend, auch andere Verbindungen mit, beispielsweise Butadien, Propylen oder ungesättigte Äther. Die erhaltenen Butenole sind chemisch nicht einheitlich, sondern stellen isomere Gemische aus Crotylalkohol, Vinylmethylcarbinol und Allylcarbinol dar, die infolge ihrer Instabilität und ihrer Fähigkeit, ineinander überzugehen, in stark wechselndem Mischungsverhältnis vorliegen können.Process for the preparation of pure butenols is known to be Butenols obtained by splitting off water from 1,3-butylene glycol in the liquid phase. In these processes, other connections also arise, in some cases very largely with, for example, butadiene, propylene or unsaturated ethers. The butenols obtained are not chemically uniform, but represent isomeric mixtures of crotyl alcohol, Vinylmethylcarbinol and allylcarbinol, which as a result of their instability and their Ability to merge into one another, to be present in strongly changing mixing proportions can.
Außerdem bilden sie in Anwesenheit von mitentstandenem Wasser azeotrope Gemische, die nicht oder nur unter großen Schwierigkeiten auseinandergetrennt werden können.In addition, they form azeotropes in the presence of the resulting water Mixtures that cannot be separated or separated only with great difficulty can.
Dagegen lassen sich die drei Alkohole in haltbarer und ohne die Gefahr einer Umwandlung destillativ leicht trennbarer Form als Gemisch ihrer Acetate gewinnen. Aus der USA.-Patentschrift 2 251983, insbesondere Beispiel 8, ist es bereits bekannt, 1,3-Butylenglykoldiacetat in Gegenwart oder Abwesenheit von Katalysatoren in dampfförmiger oder flüssiger Phase zu Butenolacetaten und Essigsäure zu zersetzen. In Abwesenheit von Katalysatoren werden nach diesem Verfahren bei 472° C aus 1,3-Butylenglykoldiacetat bei einem Durchsatz von 127 g je Liter Kontaktraum und Stunde unter 86°/o Umsetzung je 35 % Butenolacetate und Butadien erhalten. Bei größerem Durchsatz sollen Temperaturen bis 700° C angewendet werden.On the other hand, the three alcohols can be obtained as a mixture of their acetates in a form that is durable and easily separable by distillation without the risk of conversion. From US Pat. No. 2,251,983, in particular Example 8, it is already known to decompose 1,3-butylene glycol diacetate in the presence or absence of catalysts in the vaporous or liquid phase to give butenol acetates and acetic acid. In the absence of catalysts, this process gives at 472 ° C. from 1,3-butylene glycol diacetate at a throughput of 127 g per liter of contact space and hour with a conversion of 35% butenol acetates and butadiene. With higher throughput, temperatures of up to 700 ° C should be used.
Es muß als unbefriedigend gelten, daß bei diesen Verfahren das 1,3-Butylenglykoldiacetat sich in gleichem Maße einerseits in die wertvollen Butenole, andererseits in das unerwünschte Butadien umwandelt; somit besteht ein erhebliches Interesse an einem Verfahren, das es gestattet, die begehrten Butenole auf dem an sich eleganten Weg über ihre Acetate auf weniger verlustreiche Weise zu erhalten.It must be considered unsatisfactory that in this process the 1,3-butylene glycol diacetate to the same extent on the one hand in the valuable butenols, on the other hand in the converts unwanted butadiene; thus there is considerable interest in one Process that allows the coveted butenole to be produced in an elegant way about getting their acetates in less lossy ways.
Es wurde gefunden, daß man reine Butenole praktisch quantitativ durch thermische Essigsäureabspaltung aus dampfförmigem 1,3-Butylenglykoldiacetat und destillative Trennung und Verseifung der erhaltenen Butenolacetate herstellen kann, indem man 10 000 bis 17 500, vorzugsweise 12 000 bis 14 000 g 1,3-Butylenglykoldiacetat je Liter Reaktionsraum und Stunde bei 500 bis 550° C, vorzugsweise 510 bis 540" C, umsetzt.It has been found that pure butenols can be carried out practically quantitatively thermal elimination of acetic acid from vaporous 1,3-butylene glycol diacetate and can produce distillative separation and saponification of the butenol acetates obtained, by adding 10,000 to 17,500, preferably 12,000 to 14,000 g of 1,3-butylene glycol diacetate per liter of reaction space and hour at 500 to 550 ° C, preferably 510 to 540 " C, implements.
Der Reaktionsraum besteht vorzugsweise aus einem von außen erwärmten Rohr aus nicht rostendem Stahl.The reaction space preferably consists of one that is heated from the outside Stainless steel tube.
Überraschenderweise besteht das nach diesem Verfahren erhaltene Reaktionsprodukt neben etwa 40% nicht umgesetztem 1,3-Butylenglykoldiacetat ausschließlich aus Essigsäure und den gewünschten Butenolacetaten; andere Stoffe, auch solche gasförmiger Natur, sind praktisch abwesend.Surprisingly, the reaction product obtained by this process exists in addition to about 40% unreacted 1,3-butylene glycol diacetate exclusively from acetic acid and the desired butenol acetates; other substances, including those of a gaseous nature, are practically absent.
Das Reaktionsgemisch läßt sich leicht durch Destillation in Essigsäure, welche erneut mit 1,3-Butylenglykol verestert werden kann, in 1,3-Butylenglykoldiacetat, das zurückgeführt wird, und in die Butenolacetate trennen. Das Gemisch der Butenolacetate besteht bei den beanspruchten Reaktionsbedingungen zu 14% aus Vinylmethylcarbinolacetat, 42,9% Allylcarbinolacetat und 42,3% Crotylacetat; es läßt sich bei Normaldruck über eine wirksame Destillationskolonne ohne Schwierigkeit in die Einzelbestandteile trennen.The reaction mixture can easily be purified by distillation in acetic acid, which can be re-esterified with 1,3-butylene glycol, in 1,3-butylene glycol diacetate, that is recycled, and separate into the butenol acetates. The mixture of butenol acetates consists of 14% vinyl methyl carbinol acetate under the claimed reaction conditions, 42.9% allyl carbinol acetate and 42.3% crotyl acetate; it can be over at normal pressure an effective distillation column without difficulty in the individual components separate.
Die Gewinnung der Alkohole aus den reinen Estern kann auf übliche Weise durch alkalische Verseifung erfolgen. Hierbei lassen sich sehr reine und haltbare, keiner Umwandlung in die isomeren Formen unterliegende Butenole gewinnen. Die Butenole sind zwar wasserlöslich, können aber aus dem salzhaltigen, zweckmäßig mit Kohlensäure neutralisierten Verseifungsgemisch, in dem sie praktisch unlöslich sind, leicht quantitativ abgetrennt werden.The extraction of the alcohols from the pure esters can be carried out in the usual way Way done by alkaline saponification. Very pure and durable, win butenols which are not subject to conversion into the isomeric forms. The butenole are water-soluble, but can be made from the salty, appropriately carbonated neutralized saponification mixture, in which they are practically insoluble, easily be separated quantitatively.
' Die auf diese Weise verlustfrei und in völliger Reinheit erhaltenen Butenole sind wertvolle Komponenten und Zwischenprodukte für die Herstellung z. B. von Polymerisationsprodukten und Mischpolymerisaten, für Polyester, ferner für Alkydharze und für wachstumsverhindernde Mittel.'Those obtained in this way without loss and in complete purity Butenols are valuable components and intermediates for the production of e.g. B. of polymerization products and copolymers, for polyester, also for Alkyd resins and for anti-growth agents.
Beispiel 166 g je Stunde reines 1,3-Butylenglykoldiacetat vom Kp.15 94 bis 96°C werden im Dauerversuch dampfförmig durch ein 1 m langes VA-Rohr von 4 mm lichter Weite geleitet. Die zur Spaltung eingestellte Ofentemperatur beträgt 515 bis 540° C, die Verweilzeit 1,0 Sekunde. Das die Apparatur verlassende, durch einfache Wasserkühlung kondensierbare Produkt aus dem Stundendurchsatz von 166 g Diacetat enthält 34,6 g = 20,7% Essigsäure, die durch Waschen mit Wasser leicht entfernt werden kann. Aus dem verbleibenden neutralen Estergemisch läßt sich an einfacher Destillationskolonne bei Übergangstemperaturen bis -134° C unter 760 mm Druck das gesamte Gemisch der erhaltenen Butenolacetate abdestillieren. Der verbleibende Rückstand besteht aus 66,4 g = 40°/o reinem Diacetat, das unter 16 mm Druck bei 90 bis 96° C übergeht.Example 166 g per hour of pure 1,3-butylene glycol diacetate of boiling point 15 94 to 96 ° C are in the endurance test in vapor form through a 1 m long VA tube with a clearance of 4 mm. The oven temperature set for the split is 515 to 540 ° C, the residence time 1.0 second. The one leaving the apparatus product which can be condensed by simple water cooling from the hourly throughput of 166 g of diacetate contains 34.6 g = 20.7% acetic acid, which can be easily removed by washing with water can be removed. From the remaining neutral ester mixture can be simple distillation column with transition temperatures down to -134 ° C below 760 mm Distill off the entire mixture of the butenol acetates obtained under pressure. The remaining one Residue consists of 66.4 g = 40% pure diacetate, which under 16 mm pressure at 90 to 96 ° C passes.
Die Ausbeute an Butenolacetaten beträgt 64,8 g = 99,4 %, bezogen auf umgesetzten Ester. Das Gemisch wird in einer sehr scharf trennenden Kolonne bei folgenden Siedepunkten destillativ zerlegt: 9,2 g Vinylmethylcarbinolacetat, Kp.7BQ 112°C ......... 14,1°/o 27,9 g Allylcarbinolacetat, Kp.780 126 bis 127°C . . 42,9"/o 27,6 g Crotylacetat, KP-760 133 bis 134° C . . 42,3"/0 Die einzelnen Acetate werden jeweils mit der im leichten Überschuß von etwa 1011/o berechneten Menge 2011/oiger wäßriger Natronlauge versetzt. Die sich abscheidenden Alkohole werden durch Einleiten von Kohlensäure neutralisiert. Man erhält: 5,8 g Vinylmethylcarbinol, Kp.,7BO 97,5° C .... nö° 1,4149 17,6 g Allylcarbinol, KP-760 1150 C ...... n2D- 1,4215 17,4 g Crotylalkohol, Kp.76" 121° C ...... n1,0 1,4300 Die OH-Zahl der Butenole beträgt 760 bis 763 (berechnet 777,8). Die Bromzahl beträgt 221 bis 222 (berechnet 222,2).The yield of butenol acetates is 64.8 g = 99.4%, based on the ester reacted. The mixture is broken down by distillation in a very sharply separating column at the following boiling points: 9.2 g vinylmethylcarbinol acetate, boiling point 7BQ 112 ° C ......... 14.1% 27.9 g allyl carbinol acetate, boiling point. 780 126 to 127 ° C. . 42.9 "/ o 27.6 g of crotyl acetate, KP-760 133 to 134 ° C.. 42.3" / o The individual acetates are each with the amount of 2011 / o aqueous sodium hydroxide solution calculated in a slight excess of about 1011 / o offset. The alcohols that separate out are neutralized by introducing carbonic acid. The following is obtained: 5.8 g vinylmethylcarbinol, b.p., 7BO 97.5 ° C ... nö ° 1.4149 17.6 g allyl carbinol, KP-760 115 0 C ...... n2D- 1.4215 17.4 g crotyl alcohol, bp 76 "121 ° C ...... n1.0 1.4300 The OH number of the butenols is 760 to 763 (calculated 777.8). The bromine number is 221 to 222 (calculated 222.2).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC25872A DE1150671B (en) | 1961-12-30 | 1961-12-30 | Process for the production of pure butenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC25872A DE1150671B (en) | 1961-12-30 | 1961-12-30 | Process for the production of pure butenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1150671B true DE1150671B (en) | 1963-06-27 |
Family
ID=7017988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC25872A Pending DE1150671B (en) | 1961-12-30 | 1961-12-30 | Process for the production of pure butenols |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1150671B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015173780A1 (en) | 2014-05-16 | 2015-11-19 | Versalis S.P.A. | Process for the production of alkenols and use thereof for the production of 1,3-butadiene |
| US10173947B2 (en) | 2014-12-12 | 2019-01-08 | Versalis S.P.A. | Process for the production of 1,3-butadiene from 1,3-butanediol |
| IT201900025000A1 (en) | 2019-12-20 | 2021-06-20 | Versalis Spa | PROCEDURE FOR THE PRODUCTION OF DIENES. |
-
1961
- 1961-12-30 DE DEC25872A patent/DE1150671B/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015173780A1 (en) | 2014-05-16 | 2015-11-19 | Versalis S.P.A. | Process for the production of alkenols and use thereof for the production of 1,3-butadiene |
| US9862664B2 (en) | 2014-05-16 | 2018-01-09 | Versalis S.P.A. | Process for the production of alkenols and use thereof for the production of 1,3-butadiene |
| US10173947B2 (en) | 2014-12-12 | 2019-01-08 | Versalis S.P.A. | Process for the production of 1,3-butadiene from 1,3-butanediol |
| IT201900025000A1 (en) | 2019-12-20 | 2021-06-20 | Versalis Spa | PROCEDURE FOR THE PRODUCTION OF DIENES. |
| US11851385B2 (en) | 2019-12-20 | 2023-12-26 | Versalis S.P.A. | Process for producing dienes |
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