CH92123A - Process for the production of terpineol. - Google Patents
Process for the production of terpineol.Info
- Publication number
- CH92123A CH92123A CH92123DA CH92123A CH 92123 A CH92123 A CH 92123A CH 92123D A CH92123D A CH 92123DA CH 92123 A CH92123 A CH 92123A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- terpineol
- production
- terpin
- hydrate
- Prior art date
Links
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 title claims description 11
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 title claims description 11
- 229940116411 terpineol Drugs 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- RBNWAMSGVWEHFP-UHFFFAOYSA-N cis-p-Menthan-1,8-diol Natural products CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-N 0.000 claims description 5
- RBNWAMSGVWEHFP-WAAGHKOSSA-N terpin Chemical compound CC(C)(O)[C@H]1CC[C@@](C)(O)CC1 RBNWAMSGVWEHFP-WAAGHKOSSA-N 0.000 claims description 5
- 229950010257 terpin Drugs 0.000 claims description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229930006948 p-menthane-3,8-diol Natural products 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229930006978 terpinene Natural products 0.000 description 1
- 150000003507 terpinene derivatives Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Treatment Of Liquids With Adsorbents In General (AREA)
Description
Verfahren zur Herstellung von Terpineol.
EMI0001.0003
Das <SEP> gewühnliclie <SEP> Verfahren <SEP> 711i# <SEP> Herstel lung <SEP> voll <SEP> Terpineol <SEP> aus <SEP> Terpinhydrat <SEP> besteht
<tb> in <SEP> dem <SEP> Sieden <SEP> des <SEP> letzteren <SEP> mit <SEP> verdünnter
<tb> Pliosphoi@sätire <SEP> oder <SEP> Schwefelsäure. <SEP> Bei <SEP> An wendung <SEP> von <SEP> Schwefelsäure <SEP> wird <SEP> immer <SEP> eitle
<tb> Mischung <SEP> von <SEP> Terpineol <SEP> mit <SEP> Terpinoleit <SEP> und
<tb> Terpinen <SEP> erbalten, <SEP> während <SEP> mit <SEP> Phosphorsäure
<tb> zwar <SEP> ini <SEP> wesentlichen <SEP> Terpineol <SEP> entsteht
<tb> (Schmidt <SEP> II-\?, <SEP> S. <SEP> 1313. <SEP> und <SEP> Beilstein <SEP> III,
<tb> S. <SEP> 520).
<SEP> jedoch <SEP> in <SEP> einer <SEP> Ausbeute, <SEP> die <SEP> hücli stens <SEP> 65 <SEP> ,1o <SEP> beträgt.
<tb>
Es <SEP> hat <SEP> siele <SEP> nun <SEP> herausgestellt, <SEP> dah, <SEP> wenn
<tb> nian <SEP> Terpinhydrat <SEP> statt <SEP> mit <SEP> Pliosphot-siiure
<tb> oder <SEP> Schwefelsäure <SEP> mit <SEP> einer <SEP> witssel igetl <SEP> Ltc sungeinerorganischen <SEP> Sulfosaiure,welciie <SEP> Stick stoff <SEP> enthält, <SEP> erwärmt, <SEP> die <SEP> Ausbeute <SEP> an <SEP> Ter pineol <SEP> wesentlich <SEP> verbessert <SEP> wird. <SEP> Besonders
<tb> gute <SEP> Erfolge <SEP> erzielt <SEP> tnan <SEP> init <SEP> Cliitiolitisiilfo säure. <SEP> Bei <SEP> deren <SEP> Verwendung <SEP> wird <SEP> die <SEP> Aus beute <SEP> nahezu <SEP> quantitativ.
<SEP> Es <SEP> kann <SEP> gleieli zeitig <SEP> eine <SEP> wesentliche <SEP> Vereinfachung <SEP> des <SEP> Ver fahrens <SEP> erzielt <SEP> werden, <SEP> indem <SEP> es <SEP> niiiglicli
<tb> wird, <SEP> Terpinhydrat <SEP> kontinuierlich <SEP> in <SEP> das <SEP> Ii'e aktionsgeniisch <SEP> laufen <SEP> zti <SEP> lasen <SEP> und <SEP> konti-
EMI0001.0004
nuierlich <SEP> eine <SEP> äquivalente <SEP> Menge <SEP> Terpineol
<tb> abzudestillieren.
<tb>
<I>Beispiel</I>
<tb> 5.) <SEP> l#'ranini <SEP> Cliinolin,ulfosäure, <SEP> 800 <SEP> Uramin
<tb> Wasser <SEP> Lind <SEP> 175 <SEP> Gran-im <SEP> Terphilivdrat <SEP> wer den <SEP> bis <SEP> zur <SEP> Destillation <SEP> erhitzt; <SEP> das <SEP> Destillat.
<tb> 140 <SEP> Grainni, <SEP> wird <SEP> fraktioniert <SEP> und <SEP> gibt:
EMI0001.0005
1. <SEP> Fraktion: <SEP> ,Spt. <SEP> 88-94 <SEP> <SEP> C,
<tb> Sp. <SEP> Gew. <SEP> 0,930.
<tb> 19 <SEP> (xramin <SEP> Terpineol <SEP> <B>15</B> <SEP> .
<tb> '?. <SEP> Fraktion: <SEP> Spt. <SEP> 94 <SEP> " <SEP> C, <SEP> Sp. <SEP> (x <SEP> ew. <SEP> 0,937,
<tb> 121 <SEP> Gramm <SEP> Terpineol <SEP> 15 <SEP> .
Process for the production of terpineol.
EMI0001.0003
The <SEP> usual <SEP> method <SEP> 711i # <SEP> production <SEP> full <SEP> terpineol <SEP> consists of <SEP> terpin hydrate <SEP>
<tb> in <SEP> the <SEP> boiling <SEP> the <SEP> the latter <SEP> diluted with <SEP>
<tb> Pliosphoi @ sätire <SEP> or <SEP> sulfuric acid. <SEP> When <SEP> is used <SEP> of <SEP> sulfuric acid <SEP>, <SEP> is always <SEP> vain
<tb> Mixture <SEP> of <SEP> Terpineol <SEP> with <SEP> Terpinoleit <SEP> and
<tb> inherited terpinene <SEP>, <SEP> while <SEP> with <SEP> phosphoric acid
<tb> although <SEP> ini <SEP> essential <SEP> terpineol <SEP> arises
<tb> (Schmidt <SEP> II- \ ?, <SEP> S. <SEP> 1313. <SEP> and <SEP> Beilstein <SEP> III,
<tb> S. <SEP> 520).
<SEP> but <SEP> in <SEP> a <SEP> yield, <SEP> the <SEP> hüclist <SEP> 65 <SEP>, 1o <SEP> is.
<tb>
It <SEP> has <SEP> siele <SEP> now <SEP> emphasized, <SEP> there, <SEP> if
<tb> nian <SEP> terpin hydrate <SEP> instead of <SEP> with <SEP> pliosphotic acid
<tb> or <SEP> sulfuric acid <SEP> with <SEP> a <SEP> witssel igetl <SEP> Ltc sung an inorganic <SEP> sulphonic acid, which contains <SEP> nitrogen <SEP>, <SEP> heated, <SEP> the <SEP> yield <SEP> of <SEP> Ter pineol <SEP> is significantly <SEP> improved <SEP>. <SEP> Especially
<tb> good <SEP> successes <SEP> achieved <SEP> tnan <SEP> init <SEP> cliitiolitisiilfo acid. <SEP> With <SEP> their <SEP> use <SEP>, <SEP> the <SEP> yield <SEP> is almost <SEP> quantitative.
<SEP> <SEP> <SEP> at the same time <SEP> a <SEP> substantial <SEP> simplification <SEP> of the <SEP> procedure <SEP> can be achieved <SEP>, <SEP> by <SEP> it <SEP> niiiglicli
<tb> is, <SEP> terpin hydrate <SEP> continuously <SEP> in <SEP> the <SEP> Ii'e action genius <SEP> run <SEP> zti <SEP> read <SEP> and <SEP> continuously
EMI0001.0004
of course <SEP> an <SEP> equivalent <SEP> amount of <SEP> terpineol
<tb> to distill off.
<tb>
<I> Example </I>
<tb> 5.) <SEP> l # 'ranini <SEP> cliinolin, sulfonic acid, <SEP> 800 <SEP> uramine
<tb> Water <SEP> and <SEP> 175 <SEP> Gran-im <SEP> Terphilivdrat <SEP> are heated <SEP> to <SEP> for <SEP> distillation <SEP>; <SEP> the <SEP> distillate.
<tb> 140 <SEP> Grainni, <SEP> is <SEP> fractionated <SEP> and <SEP> gives:
EMI0001.0005
1. <SEP> parliamentary group: <SEP>, Spt. <SEP> 88-94 <SEP> <SEP> C,
<tb> Sp. <SEP> Weight <SEP> 0.930.
<tb> 19 <SEP> (xramin <SEP> Terpineol <SEP> <B> 15 </B> <SEP>.
<tb> '?. <SEP> parliamentary group: <SEP> Spt. <SEP> 94 <SEP> "<SEP> C, <SEP> Sp. <SEP> (x <SEP> ew. <SEP> 0.937,
<tb> 121 <SEP> grams <SEP> terpineol <SEP> 15 <SEP>.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL92123X | 1919-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH92123A true CH92123A (en) | 1921-12-16 |
Family
ID=19759710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH92123D CH92123A (en) | 1919-11-10 | 1920-11-10 | Process for the production of terpineol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH92123A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2467330A (en) * | 1944-06-17 | 1949-04-12 | Union Bay State Chemical Co In | Preparation of derivatives of aliphatic terpenes |
| EP0035703A1 (en) * | 1980-03-10 | 1981-09-16 | Krems-Chemie Gesellschaft m.b.H. | Process for the manufacture of terpineol |
-
1920
- 1920-11-10 CH CH92123D patent/CH92123A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2467330A (en) * | 1944-06-17 | 1949-04-12 | Union Bay State Chemical Co In | Preparation of derivatives of aliphatic terpenes |
| EP0035703A1 (en) * | 1980-03-10 | 1981-09-16 | Krems-Chemie Gesellschaft m.b.H. | Process for the manufacture of terpineol |
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