DE1643147B2 - Verfahren zur herstellung von epsilon-caprolacton - Google Patents
Verfahren zur herstellung von epsilon-caprolactonInfo
- Publication number
- DE1643147B2 DE1643147B2 DE19671643147 DE1643147A DE1643147B2 DE 1643147 B2 DE1643147 B2 DE 1643147B2 DE 19671643147 DE19671643147 DE 19671643147 DE 1643147 A DE1643147 A DE 1643147A DE 1643147 B2 DE1643147 B2 DE 1643147B2
- Authority
- DE
- Germany
- Prior art keywords
- caprolactone
- production
- hours
- catalyst
- products
- 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.)
- Granted
Links
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000003054 catalyst Substances 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 6
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 claims description 4
- 150000007514 bases Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000011787 zinc oxide Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- -1 oxides Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000006136 alcoholysis reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910000011 cadmium carbonate Inorganic materials 0.000 description 1
- GKDXQAKPHKQZSC-UHFFFAOYSA-L cadmium(2+);carbonate Chemical compound [Cd+2].[O-]C([O-])=O GKDXQAKPHKQZSC-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR49397A FR1474903A (fr) | 1966-02-12 | 1966-02-12 | Procédé de préparation d'epsiloncaprolactone |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1643147A1 DE1643147A1 (de) | 1972-04-06 |
| DE1643147B2 true DE1643147B2 (de) | 1973-06-14 |
| DE1643147C3 DE1643147C3 (en, 2012) | 1974-01-24 |
Family
ID=8601219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671643147 Granted DE1643147B2 (de) | 1966-02-12 | 1967-01-31 | Verfahren zur herstellung von epsilon-caprolacton |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4819640B1 (en, 2012) |
| AT (1) | AT265231B (en, 2012) |
| BE (1) | BE693971A (en, 2012) |
| CH (1) | CH468374A (en, 2012) |
| DE (1) | DE1643147B2 (en, 2012) |
| ES (1) | ES336114A1 (en, 2012) |
| FR (1) | FR1474903A (en, 2012) |
| GB (1) | GB1153364A (en, 2012) |
| LU (1) | LU52952A1 (en, 2012) |
| NL (1) | NL6702054A (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3546251A (en) * | 1966-05-25 | 1970-12-08 | Chisso Corp | Process for producing caprolactone |
| DE2714564C2 (de) * | 1977-04-01 | 1986-01-02 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von cyclischen Diestern der Undecandisäure |
| GB8621094D0 (en) * | 1986-09-01 | 1986-10-08 | Ici Plc | Loading of polymer additives |
| DE3823213A1 (de) * | 1988-07-08 | 1990-01-11 | Basf Ag | Verfahren zur herstellung von caprolacton |
| JPH0798816B2 (ja) * | 1990-04-25 | 1995-10-25 | 宇部興産株式会社 | ε―カプロラクトンの製造法 |
| US5100435A (en) * | 1990-12-04 | 1992-03-31 | Kimberly-Clark Corporation | Meltblown nonwoven webs made from epoxy/pcl blends |
| DE19808846A1 (de) * | 1998-03-03 | 1999-09-09 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Lactonen |
| CN1202106C (zh) | 2000-08-24 | 2005-05-18 | 联合碳化化学及塑料技术公司 | 内酯的制备方法 |
-
1966
- 1966-02-12 FR FR49397A patent/FR1474903A/fr not_active Expired
-
1967
- 1967-01-24 GB GB361267A patent/GB1153364A/en not_active Expired
- 1967-01-26 ES ES336114A patent/ES336114A1/es not_active Expired
- 1967-01-28 JP JP554967A patent/JPS4819640B1/ja active Pending
- 1967-01-31 DE DE19671643147 patent/DE1643147B2/de active Granted
- 1967-02-08 CH CH185767A patent/CH468374A/fr unknown
- 1967-02-08 LU LU52952D patent/LU52952A1/xx unknown
- 1967-02-10 AT AT128567A patent/AT265231B/de active
- 1967-02-10 NL NL6702054A patent/NL6702054A/xx unknown
- 1967-02-13 BE BE693971D patent/BE693971A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE693971A (en, 2012) | 1967-07-17 |
| ES336114A1 (es) | 1968-01-01 |
| DE1643147A1 (de) | 1972-04-06 |
| JPS4819640B1 (en, 2012) | 1973-06-14 |
| FR1474903A (fr) | 1967-03-31 |
| DE1643147C3 (en, 2012) | 1974-01-24 |
| LU52952A1 (en, 2012) | 1967-04-10 |
| AT265231B (de) | 1968-10-10 |
| CH468374A (fr) | 1969-02-15 |
| NL6702054A (en, 2012) | 1967-08-14 |
| GB1153364A (en) | 1969-05-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |