DE1518517C - - Google Patents
Info
- Publication number
- DE1518517C DE1518517C DE19651518517 DE1518517A DE1518517C DE 1518517 C DE1518517 C DE 1518517C DE 19651518517 DE19651518517 DE 19651518517 DE 1518517 A DE1518517 A DE 1518517A DE 1518517 C DE1518517 C DE 1518517C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- parts
- oxadicarboxylic
- hours
- acids
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 150000007513 acids Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 150000001447 alkali salts Chemical class 0.000 claims description 6
- -1 alkali metal salts Chemical class 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 239000004033 plastic Substances 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- 239000004014 plasticizer Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 239000007795 chemical reaction product Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N γ-lactone 4-hydroxy-butyric acid Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 5
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N Nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N δ-Valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000005643 Pelargonic acid Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N Tridecylic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- YFHXGDVQPDDYRI-UHFFFAOYSA-N 2-chlorotridecanoic acid Chemical compound CCCCCCCCCCCC(Cl)C(O)=O YFHXGDVQPDDYRI-UHFFFAOYSA-N 0.000 description 1
- VJESHXJCDSQCMT-UHFFFAOYSA-N 6-(3-carboxypropoxy)hexanoic acid Chemical compound OC(=O)CCCCCOCCCC(O)=O VJESHXJCDSQCMT-UHFFFAOYSA-N 0.000 description 1
- XWWKSLXUVZVGSP-UHFFFAOYSA-N 6-chlorohexanoic acid Chemical compound OC(=O)CCCCCCl XWWKSLXUVZVGSP-UHFFFAOYSA-N 0.000 description 1
- 210000003608 Feces Anatomy 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N Heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 241000282941 Rangifer tarandus Species 0.000 description 1
- 229940035295 Ting Drugs 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001681 protective Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30065 | 1965-01-05 | ||
| JP30065 | 1965-01-05 | ||
| JP566665 | 1965-02-03 | ||
| JP566765 | 1965-02-03 | ||
| JP566665 | 1965-02-03 | ||
| JP566765 | 1965-02-03 | ||
| DEA0050919 | 1965-11-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1518517A1 DE1518517A1 (de) | 1972-04-13 |
| DE1518517C true DE1518517C (he) | 1973-04-19 |
Family
ID=27274400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651518517 Granted DE1518517A1 (de) | 1965-01-05 | 1965-11-30 | Oxadicarbonsaeuren und Verfahren zu ihrer Herstellung |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3431298A (he) |
| DE (1) | DE1518517A1 (he) |
| GB (1) | GB1105819A (he) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870749A (en) * | 1971-03-10 | 1975-03-11 | Andre Danesh | Preparation of salts and complexes of substituted oxyacetate |
| DE2446687A1 (de) * | 1974-09-30 | 1976-04-15 | Henkel & Cie Gmbh | Verfahren zur herstellung von aetherpolycarbonsaeuren |
| DE2446686A1 (de) * | 1974-09-30 | 1976-04-15 | Henkel & Cie Gmbh | Verfahren zur herstellung von aetherpolycarbonsaeuren |
| US3994959A (en) * | 1975-04-18 | 1976-11-30 | Chevron Research Company | Ether acids and ester derivatives thereof |
| US4110371A (en) * | 1975-11-04 | 1978-08-29 | Texaco Development Corporation | Preparation of oxydicarboxylic acid salts |
| US5648387A (en) * | 1995-03-24 | 1997-07-15 | Warner-Lambert Company | Carboxyalkylethers, formulations, and treatment of vascular diseases |
| GB2489722B (en) | 2011-04-06 | 2017-01-18 | Precitec Optronik Gmbh | Apparatus and method for determining a depth of a region having a high aspect ratio that protrudes into a surface of a semiconductor wafer |
| DE102011051146B3 (de) | 2011-06-17 | 2012-10-04 | Precitec Optronik Gmbh | Prüfverfahren zum Prüfen einer Verbindungsschicht zwischen waferförmigen Proben |
| DE102012111008B4 (de) | 2012-11-15 | 2014-05-22 | Precitec Optronik Gmbh | Optisches Messverfahren und optische Messvorrichtung zum Erfassen einer Oberflächentopographie |
| WO2014203161A1 (de) | 2013-06-17 | 2014-12-24 | Precitec Optronik Gmbh | Optische messvorrichtung zum erfassen von abstandsdifferenzen und optisches messverfahren |
| US10234265B2 (en) | 2016-12-12 | 2019-03-19 | Precitec Optronik Gmbh | Distance measuring device and method for measuring distances |
| DE102017126310A1 (de) | 2017-11-09 | 2019-05-09 | Precitec Optronik Gmbh | Abstandsmessvorrichtung |
| DE102018130901A1 (de) | 2018-12-04 | 2020-06-04 | Precitec Optronik Gmbh | Optische Messeinrichtung |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2352641A (en) * | 1941-08-05 | 1944-07-04 | Goodrich Co B F | Preparation of beta-alkoxy monocarboxylic acids |
| US2369640A (en) * | 1943-02-08 | 1945-02-20 | Shell Dev | Anticorrosive |
| DE836936C (de) * | 1945-03-06 | 1952-04-17 | Basf Ag | Verfahren zur Herstellung von AEtherdicarbonsaeuren und deren Salzen |
| US2623033A (en) * | 1950-03-20 | 1952-12-23 | Elastic copolyesters and process | |
| US2623031A (en) * | 1950-03-20 | 1952-12-23 | Du Pont | Elastic linear copolyesters |
| US2725309A (en) * | 1951-06-18 | 1955-11-29 | Du Pont | Coated non-woven fabric and method of making |
| US2963371A (en) * | 1957-10-14 | 1960-12-06 | Swift & Co | Emulsifying agents in shortening and process of producing same |
-
1965
- 1965-10-23 US US504075A patent/US3431298A/en not_active Expired - Lifetime
- 1965-11-02 GB GB46421/65A patent/GB1105819A/en not_active Expired
- 1965-11-30 DE DE19651518517 patent/DE1518517A1/de active Granted
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