DE2641132A1 - Verfahren zur gewinnung von aethylenglycol oder propylenglycol - Google Patents
Verfahren zur gewinnung von aethylenglycol oder propylenglycolInfo
- Publication number
- DE2641132A1 DE2641132A1 DE19762641132 DE2641132A DE2641132A1 DE 2641132 A1 DE2641132 A1 DE 2641132A1 DE 19762641132 DE19762641132 DE 19762641132 DE 2641132 A DE2641132 A DE 2641132A DE 2641132 A1 DE2641132 A1 DE 2641132A1
- Authority
- DE
- Germany
- Prior art keywords
- glycol
- ethylene glycol
- phase
- mixture
- propylene glycol
- 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.)
- Withdrawn
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 452
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 title claims description 116
- 238000000034 method Methods 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 claims description 57
- 238000004821 distillation Methods 0.000 claims description 54
- -1 carboxylate ester Chemical class 0.000 claims description 52
- 239000003795 chemical substances by application Substances 0.000 claims description 46
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 46
- 150000002148 esters Chemical class 0.000 claims description 23
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 22
- 238000010992 reflux Methods 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 45
- 230000007062 hydrolysis Effects 0.000 description 38
- 239000012071 phase Substances 0.000 description 37
- 239000000047 product Substances 0.000 description 30
- 238000010533 azeotropic distillation Methods 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 18
- 238000000926 separation method Methods 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 150000005690 diesters Chemical class 0.000 description 14
- 150000002334 glycols Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- UKQJDWBNQNAJHB-UHFFFAOYSA-N 2-hydroxyethyl formate Chemical compound OCCOC=O UKQJDWBNQNAJHB-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000004508 fractional distillation Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000007670 refining Methods 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000009928 pasteurization Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 2
- LFGXUAPUBQKJIQ-UHFFFAOYSA-N 2-formyloxyethyl acetate Chemical compound CC(=O)OCCOC=O LFGXUAPUBQKJIQ-UHFFFAOYSA-N 0.000 description 2
- BEKXVQRVZUYDLK-UHFFFAOYSA-N 2-hydroxyethyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCCO BEKXVQRVZUYDLK-UHFFFAOYSA-N 0.000 description 2
- GIOCILWWMFZESP-UHFFFAOYSA-N 2-hydroxyethyl butanoate Chemical compound CCCC(=O)OCCO GIOCILWWMFZESP-UHFFFAOYSA-N 0.000 description 2
- SFAMKDPMPDEXGH-UHFFFAOYSA-N 2-hydroxyethyl propanoate Chemical compound CCC(=O)OCCO SFAMKDPMPDEXGH-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000004675 formic acid derivatives Chemical class 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- JUVBNUWZRZREEE-UHFFFAOYSA-N 2-hydroxyethyl hexanoate Chemical compound CCCCCC(=O)OCCO JUVBNUWZRZREEE-UHFFFAOYSA-N 0.000 description 1
- GFNKWCJODVREDZ-UHFFFAOYSA-N 2-hydroxyethyl pentanoate Chemical compound CCCCC(=O)OCCO GFNKWCJODVREDZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001292396 Cirrhitidae Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical class C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000126 substance Substances 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/612,826 US4021311A (en) | 1975-09-12 | 1975-09-12 | Recovery of alkylene glycols by azeotropic distillation with 1,2,3-trimethyl benzene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2641132A1 true DE2641132A1 (de) | 1977-03-24 |
Family
ID=24454800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762641132 Withdrawn DE2641132A1 (de) | 1975-09-12 | 1976-09-13 | Verfahren zur gewinnung von aethylenglycol oder propylenglycol |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4021311A (enExample) |
| JP (1) | JPS5236611A (enExample) |
| BE (1) | BE846056A (enExample) |
| DE (1) | DE2641132A1 (enExample) |
| FR (1) | FR2323670A1 (enExample) |
| GB (1) | GB1554648A (enExample) |
| IT (1) | IT1066264B (enExample) |
| NL (1) | NL168485C (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4151048A (en) * | 1977-06-06 | 1979-04-24 | Halcon Research And Development Corporation | Recovery of alkylene glycols by azeotropic distillation |
| US4187153A (en) * | 1977-11-14 | 1980-02-05 | Halcon Research & Development Corporation | Production of alkylene glycols |
| US4519875A (en) * | 1984-05-09 | 1985-05-28 | The Halcon Sd Group, Inc. | Purification of ethylene glycol derived from ethylene carbonate |
| US4935102A (en) * | 1989-12-27 | 1990-06-19 | Lloyd Berg | Separation of 2,3-butanediol from propylene glycol by azeotropic distillation |
| US4975158A (en) * | 1989-12-27 | 1990-12-04 | Lloyd Bert | Recovery of glycerine from polyols by azeotropic distillation |
| US4980033A (en) * | 1990-09-04 | 1990-12-25 | Lloyd Berg | Recovery of triethylene glycol from triols by azeotropic distillation |
| FR2698017B1 (fr) * | 1992-11-19 | 1995-03-10 | Inst Francais Du Petrole | Procédé de régénération d'un dessicant liquide. |
| ES2124928T3 (es) | 1994-04-18 | 1999-02-16 | Basf Ag | Recuperacion de glicoles de fluidos industriales que contienen glicol usados. |
| US5972172A (en) * | 1996-12-23 | 1999-10-26 | Berg; Lloyd | Separation of 1,2,4-trimethylbenzene from 1,2,3-trimethylbenzene by extractive distillation |
| US5720857A (en) * | 1997-01-02 | 1998-02-24 | Berg; Lloyd | Separation of 1,2,4-trimethylbenzene from 1,2,3-trimethylbenzene by azeotropic distillation |
| US20140005352A1 (en) * | 2012-06-29 | 2014-01-02 | Invista North America S.A R.L. | Gas scrubber and related processes |
| CN115141081B (zh) * | 2022-07-18 | 2024-01-23 | 常州大学 | 基于共沸精馏方式分离共沸物乙二醇和乙二醇二乙酸酯的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2228431A (en) * | 1938-01-03 | 1941-01-14 | Standard Alcohol Co | Method of purifying glycols |
| US3074962A (en) * | 1958-04-22 | 1963-01-22 | Union Carbide Corp | Separation of ethylene carbonate from admixture with ethylene glycol |
| US3066116A (en) * | 1959-05-26 | 1962-11-27 | American Cyanamid Co | Polyesters using molecular sieve to remove ethylene glycol |
| GB1142057A (en) * | 1966-11-09 | 1969-02-05 | Bp Chem Int Ltd | Separation of formic acid from mixtures with other acids |
| US3809724A (en) * | 1971-09-08 | 1974-05-07 | Halcon International Inc | Preparation and recovery of alkylene glycols |
| JPS581502B2 (ja) * | 1975-03-22 | 1983-01-11 | 株式会社日立製作所 | テレビジヨンサツゾウソウチ |
-
1975
- 1975-09-12 US US05/612,826 patent/US4021311A/en not_active Expired - Lifetime
-
1976
- 1976-09-02 NL NLAANVRAGE7609755,A patent/NL168485C/xx not_active IP Right Cessation
- 1976-09-10 FR FR7627240A patent/FR2323670A1/fr active Granted
- 1976-09-10 IT IT51224/76A patent/IT1066264B/it active
- 1976-09-10 BE BE170507A patent/BE846056A/xx unknown
- 1976-09-13 GB GB37895/76A patent/GB1554648A/en not_active Expired
- 1976-09-13 DE DE19762641132 patent/DE2641132A1/de not_active Withdrawn
- 1976-09-13 JP JP51109718A patent/JPS5236611A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2323670B1 (enExample) | 1980-06-06 |
| BE846056A (fr) | 1977-03-10 |
| NL168485B (nl) | 1981-11-16 |
| NL7609755A (nl) | 1977-03-15 |
| GB1554648A (en) | 1979-10-24 |
| FR2323670A1 (fr) | 1977-04-08 |
| NL168485C (nl) | 1982-04-16 |
| IT1066264B (it) | 1985-03-04 |
| US4021311A (en) | 1977-05-03 |
| JPS5236611A (en) | 1977-03-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69804630T2 (de) | Reindarstellung von propylenoxid | |
| DE2244229C3 (de) | Verfahren zur Gewinnung von Äthylenglycol oder Propylenglycol | |
| DE69804638T2 (de) | Trennung von methanol und propylenoxid aus einem reaktiosgemisch | |
| EP0334154B1 (de) | Verfahren zur kontinuierlichen Veresterung von Fettsäuren | |
| EP0234508B1 (de) | Verfahren zur kontinuierlichen Abtrennung von Wasser aus Gemischen mit organischen Substanzen | |
| DE1903552B2 (de) | Verfahren zur reinigung von gesaettigten aliphatischen alkoholen | |
| DE2834555B2 (de) | Verfahren zur Reinigung von durch Epoxidation mit einem organischen Hydroperoxid erhaltenen Propylenoxid durch extraktive Destillation | |
| DD147664A5 (de) | Verfahren zur gleichzeitigen herstellung von reinem methyl-tert.-butylether | |
| DE60108962T2 (de) | Verfahren zur reinigung und wiedergewinnung von acetonitril | |
| EP0790230A1 (de) | Verfahren zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure | |
| DE2641131C2 (de) | Verfahren zur Gewinnung von Äthylenglycol oder Propylenglycol | |
| EP1242346B1 (de) | Verfahren zur reinigung von durch hydrierung hergestelltem trimethylolpropan durch kontinuierliche destillation | |
| DE2641132A1 (de) | Verfahren zur gewinnung von aethylenglycol oder propylenglycol | |
| DD232483A5 (de) | Verfahren zur reinigung von ethylenglykol | |
| EP0962444B1 (de) | Verfahren zur Aufarbeitung von rohem, flüssigem Vinylacetat | |
| DE69809759T2 (de) | Reinigung von einem methanolstrom | |
| DE2641134A1 (de) | Verfahren zur reinigung von aethylenglycol oder propylenglycol | |
| EP1246785B1 (de) | Verfahren zur zersetzung von bei der synthese mehrwertiger alkohole gebildeter hochsiedender nebenprodukte | |
| DE2244228A1 (de) | Verfahren zur erzeugung von mehrwertigen alkoholen | |
| DE2824859A1 (de) | Verfahren zur gewinnung von ethylenglykol oder propylenglykol | |
| DE69501120T2 (de) | Verfahren zur Gewinnung von Dipropylenglykol-Tert-Butylethern | |
| DE2849249A1 (de) | Verfahren zur reinigung von alkylenglykolen | |
| DE2641133A1 (de) | Verfahren zur gewinnung von aethylenglycol oder propylenglycol | |
| DE2519292C3 (de) | Verfahren zur Auftrennung einer im wesentlichen Propylenoxid, Propylen, eine 1-4 Kohlenstoff atome aufweisende Carbonsäure und Benzol enthaltenden Losung | |
| DE69801783T2 (de) | Methode zur Gewinnung von Alkylvinylethern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8125 | Change of the main classification | ||
| 8178 | Suspension cancelled | ||
| AF | Is addition to no. |
Ref country code: DE Ref document number: 2641131 Format of ref document f/p: P |
|
| 8127 | New person/name/address of the applicant |
Owner name: HALCON RESEARCH AND DEVELOPMENT CORP., 10016 NEW Y |
|
| 8162 | Independent application | ||
| 8136 | Disposal/non-payment of the fee for publication/grant | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |