DE197309C - - Google Patents
Info
- Publication number
- DE197309C DE197309C DENDAT197309D DE197309DA DE197309C DE 197309 C DE197309 C DE 197309C DE NDAT197309 D DENDAT197309 D DE NDAT197309D DE 197309D A DE197309D A DE 197309DA DE 197309 C DE197309 C DE 197309C
- Authority
- DE
- Germany
- Prior art keywords
- hydrochloric acid
- weight
- glycerin
- mono
- glycerol
- 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.)
- Active
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-MCPD Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 claims description 5
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 claims description 4
- RBNPOMFGQQGHHO-UHFFFAOYSA-N Glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N HCl HCl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 235000011187 glycerol Nutrition 0.000 description 9
- 229960000583 Acetic Acid Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229940093915 Gynecological Organic acids Drugs 0.000 description 1
- NJTGANWAUPEOAX-UHFFFAOYSA-N MolPort-023-220-454 Chemical compound OCC(O)CO.OCC(O)CO NJTGANWAUPEOAX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
| - | tvtq O |
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KAISERLICHES
PATENTAMT.
PATENTSCHRIFT
- Λ* 197309 KLASSE 12o. GRUPPE
C. F. BOEHRINGER & SÖHNE in WALDHOF b. MANNHEIM.
Verfahren zur Darstellung von Mono- und Dichlorhydrin aus Glycerin und Salzsäure.
Zusatz zum Patente 197308 vom 20. November 1906.
Patentiert im Deutschen Reiche vom 15. Dezember 1906 ab. Längste Dauer: 19. November 1921.
Das durch Patent 197308 geschützte Verfahren zur Darstellung von Mono- und Dichlorhydrin
besteht darin,.daß man bei Gegenwart organischer Säuren Glycerin mit gasförmiger
Salzsäure behandelt. Es wurde nun gefunden, daß auch die reaktionsbeschleunigende
Wirkung des Säurezusatzes eintritt,
wenn man statt gasförmiger nicht zu verdünnte wäßrige Salzsäure anwendet. Naturgemäß
liegen in diesem Falle die zur Erzielung einer günstigen Ausbeute notwendigen Temperaturen etwas höher als bei dem Verfahren
des Hauptpatentes.
| Eisessig | Salzsäure (1,19) | Temperatur | Dauer in |
Mono- chlor- |
Di chlor |
— | im offenen | |
| Vers. | Gewichtsteilen | in Gewichtsteilen |
Stunden | hydrin in Prc |
hydrin zenten |
—■ | .. Gefäß | |
| Nr. | ι Gewichtsteil Glycerin |
aui ι Gewichtsteil Glycerin |
/95° : | 12 | von angewandtem Glycerin |
— | ||
| I | O | 95° | 12 | 7 | ||||
| 2 | ■ /20 | ^v2 . | 95° | 12 | 5« | |||
| 3 | -1Ao | 1V2 | 95° | 12 | 60 | — | ||
| 4 | 0 | 272 | 95° | 12 | 16 | |||
| 5 | 1Ao | . 2V* | 95° | IS | 70 | |||
| 6 | 0 | 37» | 95° - | 5 | 17 | |||
| 7 | 7xo | 3Vs | 95° | 12 | 70 | |||
| 8 | 1Ao | 372 | 80 | |||||
| Eisessig | Salzsäure (1,19) | Temperatur | Dauer in |
Mono- chlor- |
Di- chlor- |
— | im Druck | |
| Vers. | Gewichtsteilen | m . Gewichtsteilen |
Stunden | hydrin in Prc |
hydrin zenten |
5 | gefäß. | |
| Nr. | ι Gewichtsteil | ι Gewichtsteil | von | ■_ | ||||
| Glycerin | Glycerin | I2O° . ■ | ■15 | angewandtem Glycerin |
—i- | |||
| 9 | O | 1V2 | 120° | 15 ■ | 60 | |||
| IO | VlO | I V2 | I2O° | 15 | 75 | 14 | ||
| II | 3Ao | i'A | 115° | 3 | 73 | 59 | ||
| 12 | O | 11A | '. "5° | 3 | 18 | _ | ||
| *3 | /50 . | 1V2 | 120° | 15 ■ | 58 | 32 | ||
| 14 | O | 3 | I2O° | . 15 | 65 | |||
| 15 | V1O | 3 | 120° | 15 | 81 | |||
| 16 | VlO | 3 | I2O° | 15 | 36 | |||
| 17 | O | 31A | I2O° | 15 | 65 | |||
| 18 | VlO | .31A | 43 | |||||
Ein Gemisch von 200 g Glycerin, 700 g Salzsäure ' (1,19) und' 20 g Eisessig wird
12 Stunden auf dem Wasserbad erhitzt. Durch Destillation im Vakuum werden 178 g Monochlorhydrin
(115 bis 120 ° bei 10 mm) und
26 g unverändertes Glycerin erhalten.
Eine Mischung von 200 g Glycerin, 700 g Salzsäure (1,19) und 20 g Eisessig wird im
geschlossenen Gefäß 6 Stunden auf 120 bis 125° erhitzt. Durch Destillation im Vakuum
werden 95 g Monochlorhydrin und 45 g unverändertes Glycerin erhalten. Aus dem wäßrigen Vorlauf werden nach dem Abstumpfen
der Säure mit Soda durch Ausschütteln mit Benzol 82 g Dichlorhydrin (Kp. 12: 74 bis 750) gewonnen.
Claims (1)
- Patent-Anspruch :Abänderung des durch Patent 197308 geschützten Verfahrens zur Darstellung von Mono- und Dichlorhydrin aus Glycerin und Salzsäure, darin bestehend, daß man statt gasförmiger Salzsäure wäßrige Salzsäure verwendet.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE197309C true DE197309C (de) |
Family
ID=460204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT197309D Active DE197309C (de) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE197309C (de) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE955233C (de) * | 1954-02-19 | 1957-01-03 | Degussa | Verfahren zur Herstellung von Pentaerythrittrichlorhydrin |
| EP0296341A2 (de) * | 1987-06-25 | 1988-12-28 | Deutsche Solvay-Werke Gmbh | Verfahren zur Herstellung von Polyglycerinen |
| WO2006111810A3 (en) * | 2005-04-18 | 2006-11-30 | Aser S R L | Process for the production of alpha, gamma-dichlorohydrin from glycerin and hydrochloric acid |
| EP1760060A1 (de) | 2003-11-20 | 2007-03-07 | SOLVAY (Société Anonyme) | Verfahren zur Herstellung von Dichloropropanol aus Glycerol |
| US7557253B2 (en) | 2005-05-20 | 2009-07-07 | Solvay (Societe Anonyme) | Method for converting polyhydroxylated aliphatic hydrocarbons into chlorohydrins |
| US7930651B2 (en) | 2007-01-18 | 2011-04-19 | Research In Motion Limited | Agenda display in an electronic device |
| US7939696B2 (en) | 2005-11-08 | 2011-05-10 | Solvay Societe Anonyme | Process for the manufacture of dichloropropanol by chlorination of glycerol |
| US8124814B2 (en) | 2006-06-14 | 2012-02-28 | Solvay (Societe Anonyme) | Crude glycerol-based product, process for its purification and its use in the manufacture of dichloropropanol |
| US8197665B2 (en) | 2007-06-12 | 2012-06-12 | Solvay (Societe Anonyme) | Aqueous composition containing a salt, manufacturing process and use |
| US8258350B2 (en) | 2007-03-07 | 2012-09-04 | Solvay (Societe Anonyme) | Process for the manufacture of dichloropropanol |
| US8273923B2 (en) | 2007-06-01 | 2012-09-25 | Solvay (Societe Anonyme) | Process for manufacturing a chlorohydrin |
| US8314205B2 (en) | 2007-12-17 | 2012-11-20 | Solvay (Societe Anonyme) | Glycerol-based product, process for obtaining same and use thereof in the manufacturing of dichloropropanol |
| US8378130B2 (en) | 2007-06-12 | 2013-02-19 | Solvay (Societe Anonyme) | Product containing epichlorohydrin, its preparation and its use in various applications |
| US8471074B2 (en) | 2007-03-14 | 2013-06-25 | Solvay (Societe Anonyme) | Process for the manufacture of dichloropropanol |
| US8507643B2 (en) | 2008-04-03 | 2013-08-13 | Solvay S.A. | Composition comprising glycerol, process for obtaining same and use thereof in the manufacture of dichloropropanol |
| US8536381B2 (en) | 2008-09-12 | 2013-09-17 | Solvay Sa | Process for purifying hydrogen chloride |
| US8715568B2 (en) | 2007-10-02 | 2014-05-06 | Solvay Sa | Use of compositions containing silicon for improving the corrosion resistance of vessels |
| US8795536B2 (en) | 2008-01-31 | 2014-08-05 | Solvay (Societe Anonyme) | Process for degrading organic substances in an aqueous composition |
| US9309209B2 (en) | 2010-09-30 | 2016-04-12 | Solvay Sa | Derivative of epichlorohydrin of natural origin |
| US9663427B2 (en) | 2003-11-20 | 2017-05-30 | Solvay (Société Anonyme) | Process for producing epichlorohydrin |
-
0
- DE DENDAT197309D patent/DE197309C/de active Active
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE955233C (de) * | 1954-02-19 | 1957-01-03 | Degussa | Verfahren zur Herstellung von Pentaerythrittrichlorhydrin |
| EP0296341A2 (de) * | 1987-06-25 | 1988-12-28 | Deutsche Solvay-Werke Gmbh | Verfahren zur Herstellung von Polyglycerinen |
| EP0296341A3 (en) * | 1987-06-25 | 1990-06-13 | Deutsche Solvay-Werke Gmbh | Process for the preparation of polyglycerines |
| US9663427B2 (en) | 2003-11-20 | 2017-05-30 | Solvay (Société Anonyme) | Process for producing epichlorohydrin |
| EP1760060A1 (de) | 2003-11-20 | 2007-03-07 | SOLVAY (Société Anonyme) | Verfahren zur Herstellung von Dichloropropanol aus Glycerol |
| KR100913626B1 (ko) * | 2003-11-20 | 2009-08-24 | 솔베이(소시에떼아노님) | 염소화된 유기 화합물의 제조 방법 |
| KR100917808B1 (ko) * | 2003-11-20 | 2009-09-18 | 솔베이(소시에떼아노님) | 유기 화합물의 제조 방법 |
| WO2006111810A3 (en) * | 2005-04-18 | 2006-11-30 | Aser S R L | Process for the production of alpha, gamma-dichlorohydrin from glycerin and hydrochloric acid |
| CN101184715B (zh) * | 2005-04-18 | 2012-07-04 | 欧洲化学工程有限公司 | 一种由甘油和盐酸生产α，γ-二氯丙醇的生产方法 |
| US7615670B2 (en) | 2005-05-20 | 2009-11-10 | Solvay (Société Anonyme) | Method for making chlorohydrin in liquid phase in the presence of heavy compounds |
| US7906691B2 (en) | 2005-05-20 | 2011-03-15 | Solvay (Societe Anonyme) | Method for making chlorohydrin in corrosion-resistant equipment |
| US7906692B2 (en) | 2005-05-20 | 2011-03-15 | Solvay (Societe Anonyme) | Method for making a chlorohydrin by chlorinating a polyhydroxylated aliphatic hydrocarbon |
| US7557253B2 (en) | 2005-05-20 | 2009-07-07 | Solvay (Societe Anonyme) | Method for converting polyhydroxylated aliphatic hydrocarbons into chlorohydrins |
| US7939696B2 (en) | 2005-11-08 | 2011-05-10 | Solvay Societe Anonyme | Process for the manufacture of dichloropropanol by chlorination of glycerol |
| US8124814B2 (en) | 2006-06-14 | 2012-02-28 | Solvay (Societe Anonyme) | Crude glycerol-based product, process for its purification and its use in the manufacture of dichloropropanol |
| US7930651B2 (en) | 2007-01-18 | 2011-04-19 | Research In Motion Limited | Agenda display in an electronic device |
| US8258350B2 (en) | 2007-03-07 | 2012-09-04 | Solvay (Societe Anonyme) | Process for the manufacture of dichloropropanol |
| US8471074B2 (en) | 2007-03-14 | 2013-06-25 | Solvay (Societe Anonyme) | Process for the manufacture of dichloropropanol |
| US8273923B2 (en) | 2007-06-01 | 2012-09-25 | Solvay (Societe Anonyme) | Process for manufacturing a chlorohydrin |
| US8378130B2 (en) | 2007-06-12 | 2013-02-19 | Solvay (Societe Anonyme) | Product containing epichlorohydrin, its preparation and its use in various applications |
| US8399692B2 (en) | 2007-06-12 | 2013-03-19 | Solvay (Societe Anonyme) | Epichlorohydrin, manufacturing process and use |
| US8197665B2 (en) | 2007-06-12 | 2012-06-12 | Solvay (Societe Anonyme) | Aqueous composition containing a salt, manufacturing process and use |
| US8715568B2 (en) | 2007-10-02 | 2014-05-06 | Solvay Sa | Use of compositions containing silicon for improving the corrosion resistance of vessels |
| US8314205B2 (en) | 2007-12-17 | 2012-11-20 | Solvay (Societe Anonyme) | Glycerol-based product, process for obtaining same and use thereof in the manufacturing of dichloropropanol |
| US8795536B2 (en) | 2008-01-31 | 2014-08-05 | Solvay (Societe Anonyme) | Process for degrading organic substances in an aqueous composition |
| US8507643B2 (en) | 2008-04-03 | 2013-08-13 | Solvay S.A. | Composition comprising glycerol, process for obtaining same and use thereof in the manufacture of dichloropropanol |
| US8536381B2 (en) | 2008-09-12 | 2013-09-17 | Solvay Sa | Process for purifying hydrogen chloride |
| US9309209B2 (en) | 2010-09-30 | 2016-04-12 | Solvay Sa | Derivative of epichlorohydrin of natural origin |
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