DE1147229B - Process for the preparation of new acylcyclopentadienyl manganese tricarbonyls - Google Patents
Process for the preparation of new acylcyclopentadienyl manganese tricarbonylsInfo
- Publication number
- DE1147229B DE1147229B DEB50748A DEB0050748A DE1147229B DE 1147229 B DE1147229 B DE 1147229B DE B50748 A DEB50748 A DE B50748A DE B0050748 A DEB0050748 A DE B0050748A DE 1147229 B DE1147229 B DE 1147229B
- Authority
- DE
- Germany
- Prior art keywords
- acylcyclopentadienyl
- new
- preparation
- manganese
- manganese tricarbonyls
- 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
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 title claims description 4
- 229910052748 manganese Inorganic materials 0.000 title claims description 4
- 239000011572 manganese Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- HPYIUKIBUJFXII-UHFFFAOYSA-N Cyclopentadienyl radical Chemical compound [CH]1C=CC=C1 HPYIUKIBUJFXII-UHFFFAOYSA-N 0.000 claims description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 2
- DEIHRWXJCZMTHF-UHFFFAOYSA-N [Mn].[CH]1C=CC=C1 Chemical compound [Mn].[CH]1C=CC=C1 DEIHRWXJCZMTHF-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NFVRUONLKHJOMB-UHFFFAOYSA-N C(C)(=O)[Mn]C1C=CC=C1 Chemical compound C(C)(=O)[Mn]C1C=CC=C1 NFVRUONLKHJOMB-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- -1 chlorides aliphatic carboxylic acids Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- SOSYBZAFWLPACM-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)[Mn]C1C=CC=C1 Chemical compound C(C1=CC=CC=C1)(=O)[Mn]C1C=CC=C1 SOSYBZAFWLPACM-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/30—Organic compounds compounds not mentioned before (complexes)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
Verfahren zur Herstellung von neuen Acylcyclopentadienylmangantricarbonylen Gegenstand der Erfindung ist ein Verfahren zur Herstellung von neuen Acylcyclopentadienylmangantricarbonylen, dadurch gekennzeichnet, daß man Cyclopentadienylmangantricarbonyl, das gegebenenfalls im Cyclopentadienylrest alkylsubstituiert ist, mit Halogeniden oder Anhydriden organischer Säuren mittels der Friedel-Craftsschen Reaktion umsetzt. Process for the preparation of new acylcyclopentadienyl manganese tricarbonyls The invention relates to a process for the preparation of new acylcyclopentadienyl manganese tricarbonyls, characterized in that cyclopentadienyl manganese tricarbonyl, the optionally is alkyl-substituted in the cyclopentadienyl radical, with halides or anhydrides more organic Reacts acids by means of the Friedel-Crafts reaction.
Geeignete Halogenide organischer Säuren sind insbesondere die Säurechloride aliphatischer Carbonsäuren, wie z. B. Acetylchlorid, Propionylchlorid, Butyrylchlorid, Valerylchlorid sowie die höhermolekularen Homologen. Ferner kommen auch in Frage Säurechloride aromatischer Carbonsäuren, wie z. B. Benzoylchlorid oder Phthalylchlorid. Suitable halides of organic acids are in particular the acid chlorides aliphatic carboxylic acids, such as. B. acetyl chloride, propionyl chloride, butyryl chloride, Valeryl chloride and the higher molecular weight homologues. Also come into question Acid chlorides of aromatic carboxylic acids, such as. B. benzoyl chloride or phthalyl chloride.
Als Anhydride organischer Säuren können z. B. As anhydrides of organic acids, for. B.
Essigsäureanhydrid, Propionsäureanhydrid, Buttersäureanhydrid, Benzoesäureanhydrid und Phthalsäureanhydrid verwendet werden.Acetic anhydride, propionic anhydride, butyric anhydride, benzoic anhydride and phthalic anhydride can be used.
Die Acylierungsreaktionen verlaufen z. B. gemäß folgenden Gleichungen: wobei die Acetylgruppe bzw. die Benzoylgruppe in die Cyclopentadienylgruppe eintntt.The acylation reactions take place e.g. B. according to the following equations: whereby the acetyl group or the benzoyl group merges into the cyclopentadienyl group.
Die erfindungsgemäß hergestellten Verbindungen können z. B. als Katalysatoren sowie als Zusätze zu Treibstoffen zwecks Verbesserung der Klopffestigkeit verwendet werden. The compounds prepared according to the invention can, for. B. as catalysts and used as additives to fuels to improve knock resistance will.
Beispiel 1 Benzoylcyclopentadienylmangantricarbonyl In einem 100-ml-Dreihalskolben, der mit Rührer, Rückflußkühler und einer Zuleitung für Stickstoff als Schutzgas versehen ist, löst man 1 g C5H5Mn(CO in 50 ml Schwefelkohlenstoff und gibt zu dieser Lösung 980 mg AlCl3 und 1 g Benzoylchlorid. Das erhaltene Reaktionsgemisch färbt sich nach kurzer Zeit tiefrot, und bei schwachem Erwärmen tritt HCl-Entwicklung ein. Die Reaktion wird durch 2stündiges Kochen am Rückflußkühler vervollständigt. Example 1 Benzoylcyclopentadienylmanganese tricarbonyl In a 100 ml three-necked flask, the one with stirrer, reflux condenser and a feed line for nitrogen as protective gas is provided, dissolve 1 g of C5H5Mn (CO in 50 ml of carbon disulfide and add to this Solution 980 mg AlCl3 and 1 g benzoyl chloride. The reaction mixture obtained is colored After a short time, it turns deep red, and with slight warming there is evolution of HCl a. The reaction is completed by refluxing for 2 hours.
Die Zersetzung des sich im Laufe des Siedens abscheidenden AlCl3-Komplexes erfolgt in schonender Weise am besten mit 30 ml Methanol, das unter Eiskühlung langsam zugetropft wird. Man trennt die CS2-Phase ab, gibt zur Methanolschicht etwa 30 ml 2 n-HCl und schüttelt zweimal mit CS2 aus. Von den vereinigten CS2-Phasen wird das Lösungsmittel entfernt und der kristalline, grüne Rückstand im Hochvakuum abdestilliert. Diese Destillation kann in einem waagerecht angeordneten Schlenkrohr erfolgen, das elektrisch beheizt wird. The decomposition of the AlCl3 complex that separates out during boiling is best done gently with 30 ml of methanol, which is done slowly while cooling with ice is added dropwise. The CS2 phase is separated off and about 30 ml are added to the methanol layer 2 n-HCl and shakes out twice with CS2. From the combined CS2 phases this will be The solvent was removed and the crystalline, green residue was distilled off in a high vacuum. This distillation can take place in a horizontally arranged Schlenk tube, the is electrically heated.
Bei 110 bis 125"C im Hochvakuum sammelt sich eine grüngelbe Flüssigkeit im kälteren Teil des Rohres, die bald zu nadelförmigen Kristallen erstarrt. Die Ausbeute an diesem Rohprodukt beträgt 1,41 g, das entspricht 930/0 der Theorie. A green-yellow liquid collects at 110 to 125 "C in a high vacuum in the colder part of the pipe, which soon solidifies into needle-shaped crystals. the The yield of this crude product is 1.41 g, which corresponds to 930/0 of theory.
Die Substanz kann sehr gut aus n-Hexan umkristallisiert werden und besteht dann aus hellgrünen, feinen Nädelchen vom Fp. 69 bis 70"C. Sie ist völlig licht- und luftbeständig und ist in CS2, Methanol, Benzol und verschiedenen anderen Kohlenwasserstoffen gut löslich. The substance can be recrystallized very well from n-hexane and then consists of light green, fine needles of m.p. 69 to 70 "C. It is complete light and air resistant and is in CS2, methanol, benzene and various others Easily soluble in hydrocarbons.
Beispiel 2 Acetylcyclopentadienylmangantricarbonyl Die Herstellung erfolgt in ganz analoger Weise zu Beispiel 1 aus 1 g C5H5Mn(CO)s, 460 mg Acetylchlorid und 980 mg AlCl3 im gleichen Molverhältnis. Example 2 Acetylcyclopentadienyl Manganese Tricarbonyl The Preparation takes place in a completely analogous manner to Example 1 from 1 g of C5H5Mn (CO) s, 460 mg of acetyl chloride and 980 mg AlCl3 in the same molar ratio.
Besonderheiten ergeben sich lediglich durch die Lichtempfindlichkeit des Rohproduktes. Nach Abdestillieren des Lösungsmittels nach der Zersetzung hinterbleibt eine Flüssigkeit, die der Destillation im Hoch- vakuum unterworfen wird. Bei 75 bis 85"C im Hochvakuum geht eine grüngelbe Flüssigkeit über, die sich am Licht rot färbt. Dieses Zersetzungsprodukt erniedrigt den Schmelzpunkt so weit, daß bei Raumtemperatur kein Erstarren der Substanz eintritt.The only special features are the light sensitivity of the raw product. After the solvent has been distilled off, it remains after the decomposition a liquid that is suitable for distillation in the high- subjected to vacuum will. At 75 to 85 "C in a high vacuum, a green-yellow liquid passes over, which turns red in the light. This decomposition product lowers the melting point so much that the substance does not solidify at room temperature.
Arbeitet man während des Destillierens unter Lichtschutz, so bilden sich stäbchenförmige gelbgrüne Kristalle. Aus den eingesetzten Mengen erhält man 1,05 g (= 880/0 der Theorie) eines Produktes, das sich aus n-Hexan - ebenfalls unter möglichst völligem Lichtschutz - umkristallisieren läßt. Das völlig reine Produkt ist in fester Form lichtunempfindlich.If you work under light protection during distillation, then form rod-shaped yellow-green crystals. The amounts used give 1.05 g (= 880/0 of theory) of a product consisting of n-hexane - also under As complete protection from light as possible - can be recrystallized. The completely pure product is insensitive to light in solid form.
Acetylcyclopentadienylmangantricarbonyl ist in einer Ausbeute von 760/0 auch aus Acetanhydrid, C6HsMn(CO)3 und AlCl3 im Molverhältnis CsHsMn(CO)3 zu AlCl3 zu Acetanhydrid = 1:3:1,2 in analoger Weise darstellbar. Acetylcyclopentadienyl manganese tricarbonyl is in yield of 760/0 also from acetic anhydride, C6HsMn (CO) 3 and AlCl3 in the molar ratio of CsHsMn (CO) 3 to AlCl3 to acetic anhydride = 1: 3: 1.2 can be represented in an analogous manner.
Die Verbindung besteht aus hellgelben, feinen Nädelchen vom Afp. 40 bis 42"C. Sie ist in CS2, Methanol, Benzol und verschiedenen anderen Kohlenwasserstoffen gut löslich. The connection consists of light yellow, fine needles from the Afp. 40 to 42 "C. It's in CS2, methanol, benzene, and various other hydrocarbons easily soluble.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB50748A DE1147229B (en) | 1958-10-16 | 1958-10-16 | Process for the preparation of new acylcyclopentadienyl manganese tricarbonyls |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB50748A DE1147229B (en) | 1958-10-16 | 1958-10-16 | Process for the preparation of new acylcyclopentadienyl manganese tricarbonyls |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1147229B true DE1147229B (en) | 1963-04-18 |
Family
ID=6969305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB50748A Pending DE1147229B (en) | 1958-10-16 | 1958-10-16 | Process for the preparation of new acylcyclopentadienyl manganese tricarbonyls |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1147229B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1003727B (en) * | 1953-11-02 | 1957-03-07 | Bataafsche Petroleum | Process for the preparation of dialkyldicyclopentadienyl iron |
-
1958
- 1958-10-16 DE DEB50748A patent/DE1147229B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1003727B (en) * | 1953-11-02 | 1957-03-07 | Bataafsche Petroleum | Process for the preparation of dialkyldicyclopentadienyl iron |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2943098A1 (en) | METHOD FOR PRODUCING DIESTERS | |
| DE2155495A1 (en) | METHOD FOR PREPARING BENZYLIDENE COMPOUNDS | |
| DE1147229B (en) | Process for the preparation of new acylcyclopentadienyl manganese tricarbonyls | |
| DE1804878C3 (en) | Process for the preparation of 5-isopropylidene-2-norbornene by isomerizing 5-isopropenyl-2-norbornene | |
| DE2049937A1 (en) | Rhodium or ruthenium complexes and metal halides - as isomerisation catalysts for conjugated diene prodn | |
| DE69914520T2 (en) | Production of unsaturated aldehydes from propargyl alcohol and conjugated diolefins | |
| DE947517C (en) | Process for the polycondensation of diol esters of aromatic dicarboxylic acids, in particular those of terephthalic acid | |
| DE935306C (en) | Process for the production of formic acid esters of the 5-oxymethylpyrocucous acid esters | |
| CH324667A (en) | Process for the production of vinyl esters of organic acids | |
| DE919409C (en) | Process for the nuclear chlorination of 1, 3, 3-trimethyl-1-phenyl-indene or 1, 3, 3, 6-tetramethyl-1- (4'-methyl-phenyl) -indene | |
| AT303962B (en) | Process for the preparation of 14-deoxy-14-tosyloxyacetoxymutilin | |
| DE953795C (en) | Process for the preparation of monothionopyrophoric acid tetraalkyl esters | |
| DE749150C (en) | Process for the production of ring-shaped acetals of formaldehyde | |
| AT218509B (en) | Process for the production of basic substituted carbinols, and of their sterically uniform racemates and their optically active components and / or their acid addition salts | |
| DE870698C (en) | Process for the production of hydroquinones | |
| DE965490C (en) | Process for the preparation of aromatic sulfonium compounds | |
| DE1068255B (en) | Process for the preparation of cyclic carboxylic acids and / or their esters from cyclododecatrienes (1,5,9) | |
| AT233530B (en) | Catalytically active solutions and processes for their production | |
| DE931651C (en) | Process for the preparation of d, 1-4-thiazolidone-2-caproic acid or its esters | |
| DE875805C (en) | Process for the preparation of the pentaerythritol dichlorohydrin monosulfuric acid ester | |
| DE2428180A1 (en) | PROCESS FOR THE PREPARATION OF SUBSTITUTED CHLOROBENZENE DERIVATIVES FROM BENZENE SULFOHLORIDE | |
| DE695863C (en) | Process for the production of aromatic hydrocarbons from hydroaromatic hydrocarbons | |
| DE880297C (en) | Process for the production of ketones, ketocarboxylic acids and keto alcohols | |
| DE878642C (en) | Process for the cyclization of geranylacetones to 2, 5, 5, 9-tetramethylhexahydrochromones or 3-oxytetrahydrojonones | |
| DE881039C (en) | Process for the preparation of the pentaerythritol dichlorohydrin monosulfuric acid ester |