FR2767821A1 - Phosgenation sous pression des alcools pour la production des chloroformiates - Google Patents
Phosgenation sous pression des alcools pour la production des chloroformiates Download PDFInfo
- Publication number
- FR2767821A1 FR2767821A1 FR9711189A FR9711189A FR2767821A1 FR 2767821 A1 FR2767821 A1 FR 2767821A1 FR 9711189 A FR9711189 A FR 9711189A FR 9711189 A FR9711189 A FR 9711189A FR 2767821 A1 FR2767821 A1 FR 2767821A1
- Authority
- FR
- France
- Prior art keywords
- radicals
- phosgene
- substituted
- carbon atoms
- unsubstituted
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 229920005862 polyol Polymers 0.000 claims abstract description 12
- 150000003077 polyols Chemical class 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- -1 aliphatic radical Chemical class 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 13
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 13
- 150000001298 alcohols Chemical class 0.000 claims description 10
- 125000005110 aryl thio group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000007872 degassing Methods 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 8
- 238000000926 separation method Methods 0.000 abstract description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 239000012429 reaction media Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 229950011260 betanaphthol Drugs 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 229910052594 sapphire Inorganic materials 0.000 description 4
- 239000010980 sapphire Substances 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VFXVAXFIFHSGNR-UHFFFAOYSA-N octyl carbonochloridate Chemical compound CCCCCCCCOC(Cl)=O VFXVAXFIFHSGNR-UHFFFAOYSA-N 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UQDUPHDELLQMOV-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctan-1-ol Chemical compound OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UQDUPHDELLQMOV-UHFFFAOYSA-N 0.000 description 1
- OECNTTIMQFCZIR-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl carbonochloridate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(Cl)=O OECNTTIMQFCZIR-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMRTOIJIGPJQX-UHFFFAOYSA-N ClC(=O)O.C(C1=CC=CC=C1)Cl Chemical compound ClC(=O)O.C(C1=CC=CC=C1)Cl ZAMRTOIJIGPJQX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9711189A FR2767821A1 (fr) | 1997-09-04 | 1997-09-04 | Phosgenation sous pression des alcools pour la production des chloroformiates |
| DE69820078T DE69820078T2 (de) | 1997-09-04 | 1998-08-31 | "Phosgenierung von Alkoholen zur Herstellung von Chlorformiaten unter Druck" |
| EP98942799A EP1012132B1 (fr) | 1997-09-04 | 1998-08-31 | Phosgenation sous pression des alcools pour la production des chloroformiates |
| JP2000508640A JP2001514240A (ja) | 1997-09-04 | 1998-08-31 | クロロホルメートを製造するためのアルコールの加圧下でのホスゲン化 |
| HU0004600A HU221125B1 (en) | 1997-09-04 | 1998-08-31 | Phosgenation under pressure of alcohol's for producing chloroformates |
| US09/486,892 US6479690B1 (en) | 1997-09-04 | 1998-08-31 | Phosgenation under pressure of alcohol's for producing chloroformates |
| PCT/FR1998/001867 WO1999011597A1 (fr) | 1997-09-04 | 1998-08-31 | Phosgenation sous pression des alcools pour la production des chloroformiates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9711189A FR2767821A1 (fr) | 1997-09-04 | 1997-09-04 | Phosgenation sous pression des alcools pour la production des chloroformiates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2767821A1 true FR2767821A1 (fr) | 1999-02-26 |
Family
ID=9510893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9711189A Pending FR2767821A1 (fr) | 1997-09-04 | 1997-09-04 | Phosgenation sous pression des alcools pour la production des chloroformiates |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6479690B1 (https=) |
| EP (1) | EP1012132B1 (https=) |
| JP (1) | JP2001514240A (https=) |
| DE (1) | DE69820078T2 (https=) |
| FR (1) | FR2767821A1 (https=) |
| HU (1) | HU221125B1 (https=) |
| WO (1) | WO1999011597A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10260084A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Auftrennung eines Stoffgemisches aus Clorwasserstoff und Phosgen |
| DE102004044592A1 (de) | 2004-09-13 | 2006-03-30 | Basf Ag | Verfahren zur Trennung von Chlorwasserstoff und Phosgen |
| US7504533B2 (en) * | 2006-04-24 | 2009-03-17 | Bayer Materialscience Llc | Process for the production of isocyanates |
| JP2009108016A (ja) * | 2007-11-01 | 2009-05-21 | Sumitomo Chemical Co Ltd | クロロギ酸アリルの製造方法 |
| PL3214066T3 (pl) * | 2009-07-16 | 2024-07-01 | Specialty Operations France | Sposób wytwarzania fluoromrówczanów fluoroalkilu |
| US9119528B2 (en) | 2012-10-30 | 2015-09-01 | Dexcom, Inc. | Systems and methods for providing sensitive and specific alarms |
| HUE048607T2 (hu) * | 2015-03-12 | 2020-08-28 | Basf Se | Eljárás foszgént és sósavat tartalmazó anyagáram szétválasztására |
| US20210300858A1 (en) * | 2018-08-06 | 2021-09-30 | Basf Se | Method for producing carbonic esters |
| CN112441923A (zh) * | 2020-12-08 | 2021-03-05 | 湖南国发精细化工科技有限公司 | 一种光气合成氯甲酸正辛酯的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1213419B (de) * | 1961-08-17 | 1966-03-31 | Union Carbide Corp | Verfahren zur Herstellung von Chlorameisensaeure-alpha-naphthylester |
| FR2484406A1 (fr) * | 1980-06-16 | 1981-12-18 | Ppg Industries Inc | Procede de preparation de chloroformiates facilement decomposables |
| EP0542132A1 (de) * | 1991-11-15 | 1993-05-19 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Chlorameisensäurearylestern |
-
1997
- 1997-09-04 FR FR9711189A patent/FR2767821A1/fr active Pending
-
1998
- 1998-08-31 JP JP2000508640A patent/JP2001514240A/ja active Pending
- 1998-08-31 DE DE69820078T patent/DE69820078T2/de not_active Expired - Lifetime
- 1998-08-31 US US09/486,892 patent/US6479690B1/en not_active Expired - Fee Related
- 1998-08-31 WO PCT/FR1998/001867 patent/WO1999011597A1/fr not_active Ceased
- 1998-08-31 EP EP98942799A patent/EP1012132B1/fr not_active Expired - Lifetime
- 1998-08-31 HU HU0004600A patent/HU221125B1/hu not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1213419B (de) * | 1961-08-17 | 1966-03-31 | Union Carbide Corp | Verfahren zur Herstellung von Chlorameisensaeure-alpha-naphthylester |
| FR2484406A1 (fr) * | 1980-06-16 | 1981-12-18 | Ppg Industries Inc | Procede de preparation de chloroformiates facilement decomposables |
| EP0542132A1 (de) * | 1991-11-15 | 1993-05-19 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Chlorameisensäurearylestern |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001514240A (ja) | 2001-09-11 |
| HU221125B1 (en) | 2002-08-28 |
| HUP0004600A2 (hu) | 2001-04-28 |
| HUP0004600A3 (en) | 2001-06-28 |
| EP1012132B1 (fr) | 2003-11-26 |
| DE69820078T2 (de) | 2005-06-09 |
| US6479690B1 (en) | 2002-11-12 |
| WO1999011597A1 (fr) | 1999-03-11 |
| EP1012132A1 (fr) | 2000-06-28 |
| DE69820078D1 (de) | 2004-01-08 |
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