DE111297C - - Google Patents
Info
- Publication number
- DE111297C DE111297C DENDAT111297D DE111297DA DE111297C DE 111297 C DE111297 C DE 111297C DE NDAT111297 D DENDAT111297 D DE NDAT111297D DE 111297D A DE111297D A DE 111297DA DE 111297 C DE111297 C DE 111297C
- Authority
- DE
- Germany
- Prior art keywords
- sodium
- acid
- xylene
- camphoric
- anhydride
- 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.)
- Active
Links
- 159000000000 sodium salts Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 20
- 230000002378 acidificating Effects 0.000 claims description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
- 150000008064 anhydrides Chemical class 0.000 claims description 13
- 150000002989 phenols Chemical class 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 230000001264 neutralization Effects 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 21
- 239000008096 xylene Substances 0.000 description 21
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 17
- 229910052708 sodium Inorganic materials 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- -1 aliphatic alcohols Chemical class 0.000 description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- VFZDNKRDYPTSTP-UHFFFAOYSA-N 5,8,8-trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione Chemical compound O=C1OC(=O)C2(C)CCC1C2(C)C VFZDNKRDYPTSTP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- LHGVFZTZFXWLCP-UHFFFAOYSA-N Guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- MGSRCZKZVOBKFT-UHFFFAOYSA-N Thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 5
- 239000005844 Thymol Substances 0.000 description 5
- 229930007823 thymol Natural products 0.000 description 5
- 229960000790 thymol Drugs 0.000 description 5
- SMLYHFLJQMKHQU-UHFFFAOYSA-N C(CCC(=O)O)(=O)O.C1=C(C)C=CC(C(C)C)=C1O Chemical compound C(CCC(=O)O)(=O)O.C1=C(C)C=CC(C(C)C)=C1O SMLYHFLJQMKHQU-UHFFFAOYSA-N 0.000 description 4
- RECUKUPTGUEGMW-UHFFFAOYSA-N Carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LSPHULWDVZXLIL-LDWIPMOCSA-N (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid Chemical compound CC1(C)[C@@H](C(O)=O)CC[C@@]1(C)C(O)=O LSPHULWDVZXLIL-LDWIPMOCSA-N 0.000 description 3
- 229960001867 Guaiacol Drugs 0.000 description 3
- RINCXYDBBGOEEQ-UHFFFAOYSA-N Succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- CLLRCVSRBJWSNZ-UHFFFAOYSA-N phenol;1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid Chemical compound OC1=CC=CC=C1.CC1(C)C(C(O)=O)CCC1(C)C(O)=O CLLRCVSRBJWSNZ-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 150000003388 sodium compounds Chemical class 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-Tribromophenol Chemical class OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical class OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- URZYOHKNDSYKEQ-UHFFFAOYSA-N butanedioic acid;2-methoxyphenol Chemical compound OC(=O)CCC(O)=O.COC1=CC=CC=C1O URZYOHKNDSYKEQ-UHFFFAOYSA-N 0.000 description 2
- 235000007746 carvacrol Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 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
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- SSIZLKDLDKIHEV-UHFFFAOYSA-N 2,6-dibromophenol Chemical class OC1=C(Br)C=CC=C1Br SSIZLKDLDKIHEV-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical class OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-Nitrophenol Chemical class OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- WYMJZZIWGKJZJD-UHFFFAOYSA-N 4-bromophenol;sodium Chemical compound [Na].OC1=CC=C(Br)C=C1 WYMJZZIWGKJZJD-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 101710026821 agnogene Proteins 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- FCPGLSSNBUVLLD-UHFFFAOYSA-N naphthalen-1-ol;sodium Chemical compound [Na].C1=CC=C2C(O)=CC=CC2=C1 FCPGLSSNBUVLLD-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000003639 thymyl group Chemical class C1(=CC(C)=CC=C1C(C)C)* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE111297C true DE111297C (fr) |
Family
ID=381046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT111297D Active DE111297C (fr) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE111297C (fr) |
-
0
- DE DENDAT111297D patent/DE111297C/de active Active
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